I couldn’t be happier for him, as he’s been one of my closest friends since high school. We went to college in two different states, and now live halfway across the country from each other. We’re both in the dog days of our lives. Building our careers, trying to see what sticks, and now he’s building a family. So being able to just sit and talk is a rarity these days. So when we did get a chance to talk, we had so much to catch each other up on.

Along the conversation, he was finally able to get something off his chest that he’d been keeping in for months. A topic that effects nearly everyone at some point:

Credit card debt.

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He walked me through how he got there, and that before the wedding, this needs to go away ASAP.

You see, on paper, my friend is doing all the right things.

A year after college, he bought a duplex with another friend. They each took a bedroom upstairs and rented out the lower half of the house. They both have good jobs that cover their share of the mortgage pretty easily. But the house wasn’t in game-time shape when they bought it so some cash for renovations went out. The walls needed a paint job. Carpet torn out and replaced with vinyl hardwood flooring. And decent furniture, as they’re renting it pre-furnished.

It was supposed to be the first steps toward building real money.

However, as time went on, he still found himself in a hole.

Ok… let me rephrase that. If you’re caught up on Season 3 of Euphoria, I’m not talking about a full blown Nate and Cassie situation, but clearly something needed to be done.

So how does the buildup start?

I’ll tell you how it starts. It starts with one or two, or like four unexpected costs come up. Your car gets towed because of the worst snowstorm the east coast had in years (twice), you switched to an HSA and doctor visits now come out of your pocket. You rescue a kitten, and now that “free” cat turned out to be the world’s most expensive cat. I don’t know, I’m just spitballing here.

Maybe your HVAC system blows up just as it starts getting nice outside. All work and no play is a recipe for disaster, so you treat yourself to a nice vacation overseas. Concert tickets. Pick your poison.

But that’s not what does you in.

It’s when normal life continues around it.

Gas to get back and forth from work. Food for the week. Date nights. Rent and all the other household bills.

It doesn’t replace the spending that you would normally do. It piles on top of it. And when it’s put on your credit card, those numbers start to stack up.

To my surprise, I found that food prices in this country have increased more than 34% since pre-covid. Sure, that’s been behind us for 7 years now. Yet more recently, food at home, or grocery prices, rose as much as 11.8 percent in 2022 alone! According to the USDA, food prices were 2.7% higher in March than the same period last year, and increased another 3.2% YoY for April.

But that’s just food, an expense we largely can’t get around—whether on credit or not. And don’t even get me started on gas prices.

Actually, I will get started. We’re starting to see and feel the effects of this war dragging on. We got confirmation that last month, the average consumer’s disposable income lagged consumer spending. Which is a fancy way of saying, on average, we’re spending more than we’re making. So when you’re already financial living on the edge, and non-discretionary costs keep rising, you may have no choice but to get by by borrowing from your future self.

To add to that, Axios makes a good point that despite sentiment, what we’re feeling on the ground, consumer spending continues to hold strong. Which is likely why haven’t seen the market really react at all to the latest CPI and PPI reports the way I would have expected. However, “aggregate spending is still being supported by the wealth effect and the upper end of the K-shaped economy, but that support is doing more of the heavy lifting—making the overall spending backdrop look increasingly uneven and fragile,” Fitch Ratings’ head of U.S. economics writes.

Going into credit card debt doesn’t necessarily mean you’re bad with money or that you’re fiscally irresponsible.

It comes for us all at some point.

The average cardholder holds a balance somewhere between $6,500–$6,800. And for households earning over $100,000, it’s often closer to $7,000 or more. Unless we’re in some sort of economic contraction, as a nation, it feels like we’re consistently hitting a new record in credit card debt.

Again, going into credit card debt doesn’t mean you’re bad with money. But it does mean that a pivot needs to be made before this manageable problem becomes a much bigger problem.

The last point I’ll make before explaining to what do about it is: the problem with high-interest debt is that it’s regressive in two ways.

The first way is that it pulls money for the future into the past.

You’re paying for things you already consumed instead of putting that money toward things that will help you get ahead—building a solid emergency fund to avoid these problems in the first place and investing to pay for the things you want to spend on in the distant future.

Second is what it does to your mental state. My friend sees himself as a provider and a hard worker, so if he just put his head down, he should be able to tough it out. Yet this weight sat on his mind for a long time before he even shared with anyone, let alone his future wife. That’s not a knock on his communication skills; these conversations are simply not that easy. High interest debt can build up fast, but take much longer to fully pay off. It can feel like your not making progress even when you are. That kind of pressure on yourself can eventually make you your own worst enemy.

With all that said, what do you do to get this monkey off your back and move on with your life?

If you have the cash flow and a decent savings already built up, that’s great.

I wouldn’t recommend you completely wipe out your savings just to close out your outstanding balance(s). While it might feel great in the short-term, if it’s not what got you there in the first place, living on the edge will certainly bring you back to where you were—like a dog chasing his own tail.

Your emergency bucket is there to act as a cushion for the expected-but-untimely, and unexpected expenses that come up.

At the onset, there are two ways I like to go about it:

1. If it’s spread across a couple of credit cards, start with the lowest balance first.
   
   This is going to help you feel like you’re making progress. Pay it off it in full and keep reading for what you’ll do next.

2. Consolidate the balances.
   
   This is not a debt consolidation loan. You’re simply pulling the balance from one card and combining it with another. And before you spaz out on me and say what about the interest on this one large balance, stay with me.
   

   Check your credit card app/website to see if you have access to 0% APR on balance transfers.
   
   A 0% balance transfer allows you to essentially wipe out the total interest you would have paid on the transfer. But you do need to pay off most, if not all, of your transferred balance during the 0% term for this strategy to work. This has worked for me and every since then, I swear by it. Be aware, this strategy isn’t “free”—there’s typically an upfront transfer charge to do so. The price of admission.

Obviously paying it off in full is ideal, but what if that’s not possible?

With your next paycheck, here’s what you’re going to do…

If you’re really tight on cashflow, it’s ok to reduce your retirement savings for a short while.

While this advice might be controversial, to me, it’s better than telling you to drastically cut your spending and reprioritize your life. (1) you know changes need to be made, and (2) you probably didn’t wish for everything to be so expensive. That’s just the way things are.

This means you temporarily pull back on 401k/IRA contributions to stabilize cash flow. Which is fine for a short amount of time. But understand the cost. One or two months is a decision. Five or six months is a trend. And trends tend to have inertia. If you wait too long, your new paycheck will become your new standard of living, and that defeats the purpose/point of what we’re ultimately trying to do here: get out of debt and back on track to securing your financial future.

Next, take your card out of your wallet - let air out for a while.

I do that mean literally and figuratively.

If you don’t actually want take it out of wallet: lock your card.

This a no harm, no foul way to put yourself on ice and really be cognizant of what you’re spending money on. “Normal life”—things like subscriptions and billpay—will resume in the background, but your card will get declined if you physically (or Apple Pay) try to use it out in the wild. This abrupt cue should make you assess whether this transaction is really worth it, and if so, to just use cash.

Finally, reassess your spending and optimize the things you’re already going to spend on.

If travel is important to you—and for a lot of people it is—learn how to do it more efficiently.

There’s a right way and a lazy way to spend on experiences. Same outcome, but very different cost. Look into travel-hack content that gives you legit and actionable advice how on where and how to save on your next trip. Not just affiliate links that helps them more than it helps you.

If you’ve already pinpointed your next destination, I guarantee you some influencer has already been there. Don’t try to reinvent the wheel. Look into their itinerary. Where and with who they booked their stay, and if it’s still out of our price range, MOVE ON.

To that end, find a card with benefits that actually benefit you. It does you no good to pay $600 a year for an AMEX card just for the flex. I’ve said before, I prefer cash back programs—it’s like I’m getting a 2-6% discount on what I was already going to spend on—but I’ve seen many people make the most out of points. Do what makes the most sense for your situation.

That’s all for me.

Until next time.

First and foremost, I want to thank new and long-time subscribers for reading my work over the years and sending me a note if one of my articles resonated with you. That has meant the world to me. It’s given me the push I needed to keep writing, especially when I felt like no one was listening.

I decided to move to Substack for a few reasons:

For one, we’re all busy people. As a content creator (if you want to call me that), I know that attention is a fleeting commodity. And as AI becomes a more dominant force in content creation, for better or worse, capturing and holding your attention will become exponentially harder. Therefore, friction will be the enemy of discovery.

So the first difference you’ll see is that my articles can be read right in your inbox without navigating to another site. If you’re new here, it will be easier to subscribe and share if you find it insightful and potentially helpful to someone you know.

This also allows me to interact with my subscribers in many more ways.

I want your feedback. Leave a comment below and/or reply to these emails if you vehemently disagree with what’s been said. That only makes me a better writer. And please, please, please keep sending me emails with personal stories if you can relate to one of mine.

Lastly, as I said goodbye to my previous site, which was built on WordPress, I skimmed through many of my earliest posts, deciding which ones I would keep or toss. My stomach turned as I forced myself through to the end of some of these naively written, long, drawn-out essays. I couldn’t believe they let me hit publish. It’s too bad ChatGPT didn’t exist then. Right after confirming that I want to schedule the post to go out on a Wednesday morning, AI would have stopped me and asked one time:

But I suppose everyone feels that way. The internet has a way of putting a timestamp next to what felt like a good idea at the time and cementing it, so you can embellish that glory (or disappointment) over and over again.

The first feeling of reprieve arrived when I found this:

This was the first logo I created in 2019 when I first started writing in college. Boy, did this thing take me back. In fact, while I’ve grown to love it and wouldn’t change a thing, the name Wealth Found Me wasn’t an original idea. As I was building my webpage and ready to hit publish, I needed a custom URL. Apparently, The Wealth Foundation was both taken and not very creative, so SquareSpace, who I was using at the time, came up with a few suggestions—I can’t recall any of the others, but I suppose that’s both the point and trivial now—one of which, www wealthfoundme .com, it had a certain ring to it. The rest, as they say, is history.

The move to Substack is merely another evolution in my writing journey.

While I would love to, I still can’t commit to a new post hitting your inbox the same time every week. I’m still trying to figure out this work/life/writing/boxing balance thing (lol, I know). Despite the new medium, this will still be a collection of my experiences, childhood stories, and money/investing/estate planning topics that I come across in my day job as a financial planner. I write about topics as they present themselves to me and what I find interesting.

Thank you for joining me on this ride.

See you next time.

This post is a recap of my trip to Scottsdale, AZ where my colleague Jonathan Novy and I were invited to speak at an estate planning conference in January.

I hope you enjoy. Thanks for reading.

All great stories must begin with a rocky start. At least, I think that’s how that works.

Let’s start with the flight from hell.

Maybe you already knew this, but within the last couple of years, I learned a little Uber cheat code. Scheduling your ride days in advance saves you time and money. You’re pretty much guaranteed a driver who shows up on time, it’s cheaper than trying to find a ride on the spot, and you’re more likely to make it to your destination on time. Since discovering this hack, I have prescheduled all my rides to and from the airport.

This works 99% of the time, so long as your state is expected to turn into wherever Mike and Sully got banished to.

My original and two other accommodation flights were canceled before I even got to the airport. That was before someone’s misfortune just became my luck. A seat opened up on a flight that was scheduled to take off at 10:57 am—the very last seat on the plane.

Once the plane was finally loaded and everyone was nice and comfortable (well, as much as you can be on a metal tube with 200 strangers)… Ding! The pilot hops on the mic and tells us we’re waiting for the food and beverages to be refilled and loaded onto the service trolley for the flight. Apparently, 55 staff members were supposed to show up that day, but only 14 did. So we sat on the plane for 2 hours before taking off. Needless to say, I was going to miss my connecting flight and day 1 of the conference.

All things considered, I made it one piece and landed in Arizona just in time to make dinner with Graham and Jonathan, who’d probably spent the day flocking in the sun without me.

With that out of the way, I started the new day with a clean slate.

The prompt they gave us goes as follows:

“Your clients spend a lifetime building wealth, but their biggest fear is often ruining their children with it. This session equips advisors with actionable strategies to help clients transfer values alongside valuations. We will explore how to use tools like Letters of Intent and Ethical Wills to humanize estate plans, ensuring that wealth serves as a launchpad for the next generation rather than a blank check that kills ambition.”

As we were running through our agenda and talking points, hands started going up and the crowd started asking questions and sharing experiences from their own practice or personal lives. Now, being extremely Type-A and deviating from the outline I stressed over for days almost gave me a heart attack, this turned our “talk” to a conversation and it couldn’t have gone any better.

Overall, it was a great discussion, and I appreciate everyone who attended and asked such thoughtful questions.

The Future of the Future

Not only was it my first time in Arizona, but it was also my first time seeing and riding in a Waymo.

If you’re not familiar with what a Waymo is, that’s ok. I wasn’t either. Waymo is Alphabet’s (Google’s parent company) first-of-its-kind fully autonomous driverless ride service.

My initial reaction when climbing into the back seat and not verbally confirming with a driver who I am was, this is weird. But once the app confirms you’re in the right car, you take off—and it doesn’t feel much different than being a passenger in someone else’s car.

Except you don’t have to make small talk or explain why you’re in town. You don’t have to listen to a stranger’s life story either (like I said here, a common occurrence for me). Or as Donald G. McNeil Jr. put it: “Waymo doesn’t get drunk, text while driving or turn its head to check out women. It doesn’t come to work in a bad mood, sexually harass passengers or try to whack its rotten kids in the back seat.” All pros, I suppose.

Our Waymo took a left onto a four-lane, two-way street, and shortly after getting up to the speed limit, the car slammed on the brakes seemingly out of nowhere. I couldn’t see anything in front of us that justified the reaction, though its sensors clearly saw something I didn’t. Thankfully, no one was close enough behind us to freak out.

Today, there are reports that Waymo is paying gig workers from companies like DoorDash to help close the doors of their vehicles left open by departing passengers. “Waymo’s reliance on people for simple tasks underscores how even the most advanced autonomous technologies still require costly human intervention for some basic operations.”

I’m excited and curious to see how the adoption of driverless cars progresses. Especially in a place like New York City.

Surely I can’t be the only one from the East Coast who’d never seen, let alone ridden, one before. Knowing NYC is the ride-hailing mecca and has one of the largest taxi fleets in the world, I’m curious how it will compete with the oligopolistic market we currently have.

Uber and Lyft often combine for well over half a million trips a day in the city. To be specific, AutoMarketplace reported a daily average of 690,695 trips for high-volume apps (Uber/Lyft) in February 2025.

That’s an enormous ecosystem of drivers, passengers, and livelihoods.

https://toddwschneider.com/dashboards/nyc-taxi-ridehailing-uber-lyft-data/

Waymo’s robotaxi network is already active across several major metros, including Austin, the San Francisco Bay Area, Phoenix, Atlanta, Los Angeles, and Miami. The company plans to expand further in 2026, targeting cities like Dallas, Denver, Detroit, Houston, Las Vegas, Nashville, Orlando, San Antonio, San Diego, and Washington—along with an international debut in London.

Still, winning NYC would be like winning the Super Bowl for Waymo.

Reports say Waymo initially began testing in New York with eight autonomous vehicles last September and must apply for an extension at the end of the testing period t0 continue operations.

To get a pulse check on sentiment, I did what any rational person in the 20th century would do… I checked out what the fine people on Reddit think about Waymo coming to NYC.

Jeffislearning (phenomenal name by the way) is right: the union isn’t shy about its feelings about this technological breakthrough hitting their city. They’re making it known that they aren’t going to roll over on this topic.

The Transport Workers Union of America—which represents 160,000 members of our mechanics, car cleaners, baggage handlers, disease control inspectors, bus operators, and more—came to fight.

“The Transport Workers Union strongly opposes the testing of autonomous vehicles from Waymo on New York City streets – the first step of a push from big tech to eliminate hundreds of thousands of jobs without regard for safety – all just to make big tech bros even richer.”

TWU International President John Samuelsen warned New Yorkers that widespread deployment would “turn pedestrians into cannon fodder” and obstruct emergency responders from doing their jobs quickly and effectively. The labor union argues it’s the opening move in a tech-driven push to eliminate large numbers of jobs while putting public safety at risk.

I don’t believe autonomous vehicles will completely demolish the driving industry. But some level of change feels inevitable.

Having a human driver could become a premium feature. I could imagine a future where riders choose preferred drivers the way people stick with their favorite barbers or trainers, while autonomous fleets handle routine A-to-B transport. The pros—the career drivers—would differentiate on service and expertise. They’d know neighborhood rhythms, traffic patterns, and the shortcuts no algorithm fully understands.

Personally, I’d love to see autonomous tech become something you can install directly into your own vehicle at a set price. Owners could pimp out their cars, then rent them out so others can earn income without putting miles on their personal vehicle. If that model takes off, the used car market could get very interesting, very fast.

Beyond this, I’m convinced more and more every day that someday, there will be a low-cost robo option for just about everything.

Robo-taxi services, robo–dating, robo-bartenders, robo-advisors, fully autonomous restaurants.

I’d be shocked if you’re not already using some level of automation and artificial intelligence in your personal and professional life. Personally, I use Chat like a second set of eyes. Review my post for grammatical errors, find gaps in my arguments, play devils advocate on social and political issues that I don’t agree with to understand other perspectives. Professionally, we’re using AI to improve post-meeting notes and suggest follow-up dates, estate planning reviews, private investment tracking, and I’m sure even more ways I’m not thinking of. My use primarily revolves around writing, however, others more ingrained with LLM’s are using it for so many creative ways that I know I haven’t even scratched the surface.

And I don’t see this trend changing anytime soon.

If anything, the tools will get cheaper, faster, and more embedded into the background of daily life. The same way smartphones quickly became extensions of our person, AI will become an extension of our tasks and decision-making. Eventually baked into nearly every product and service you already use.

But just because a robot can do something, maybe even for a lower price, doesn’t necessarily mean it’s better. This will simply put a premium on the human experience. There’s going to be a huge emphasis on creativity and judgement skills.

What are your thoughts on driverless cars coming to a city like New York? I’m genuinely curious how you see this playing out.

Outside of that short stretch between Thanksgiving and Christmas, there’s nothing enjoyable about 20-degree whipping winds (maybe even less, depending on where you are). Or an avoidant attachment style relationship with sunlight, or hazardous driving conditions. It slows down everything.

Seasonal depression—unironically referred to as SAD in the medical field—is real. At least it is for me. I hate this time of year. The decrease in sunlight disrupts your circadian rhythm, your body’s internal clock, with the sun setting around 4 o’clock in the afternoon. Your body is responding to its natural instincts, getting the signal to wind down and rest, yet if you’re like me, you still have so much work and activities to do.

I also feel that this time of the year, more than any other season, we see or hear about others losing loved ones. I have a strange relationship with death. Despite taking on a role where I talk about hypothetical quietus weekly (perhaps to cope with past traumas), I’m not immune to the destructive effects it has on people.

Late last year, my uncle** Stan passed away. We weren’t related by blood, and I didn’t know him all that well. I only met him a handful of times when they came up from Florida to visit for the holidays. I do know that he was a doctor. A cardiothoracic surgeon. And a damn good one, at that.

The only real memory I do have of him was the Thanksgiving around the time I found out I had gotten the job at Ritholtz. I remember saving the news for after the food was prepared, lots of wine had been had, and everyone had their seat at the table, ready to eat. That’s when I told everyone, not just where I’d be working after graduation, but where I’d be working—NYC! No one had ever been so outwardly proud of me before. Needless to say, more wine was had. Stan pulls me to the side and says, when I make it on Wall Street, he wants my stock picks. (Trust me, I haven’t ‘made’ it quite yet, nor would he want them. I’m a walking tax loss harvest.)

So when I got the news that he had passed due to natural causes, this saddened me. That moment will forever be a core memory of mine. However, maybe now that I’m an adult, or “responsible,” or work in finance, I’ve been filled in on the details I was completely oblivious to growing up. I learned that Uncle Stan and Aunt Mary weren’t technically married.

They’d been together for more years than I have been alive, yet they never tied the knot.

And look, there are many reasons why people choose not to get married.

Maybe they’re just not interested in the institution of marriage. Maybe they’ve lost a spouse young, but also don’t want to spend the rest of their time alone, and they just don’t feel the need to go through the hoopla all over again.

Hell, it wasn’t until the Obergefell v. Hodges Supreme Court case in 2015 that same sex marriage officially became federally legal. More and more people are opting out of the traditional path to spend a lifetime together. But even if you do decide to walk down the aisle, the wedding itself and the ways in which we decide to celebrate look increasingly different for my generation. Some—really, most—of my friends who recently did the thing are deciding to pocket their would-be-wedding money and take an extravagant vacation with it. Using what’s left as a down payment on their future home.

Whatever the case may be, a piece of paper does not define the strength of your relationship.

Now, with that being said, unmarried couples will have to accept certain tradeoffs and face hurdles when it comes to estate planning that married couples don’t.

Dying intestate, or without a will or trust, in most states presume that you meant to leave everything to your spouse. However, that’s not a given for non-married couples.

In my home state of New Jersey, if you pass without kids and your parents are no longer around, your assets are split between your siblings. This may be fine, but it also may not be your choice. Especially if you’re in a long-term committed relationship. You can see the chart below for other scenarios. Yet what it doesn’t say is anything about your best friend that you’ve spent the last decade with.

Weiner Law – intestate rules

Estate planning allows you to decide who you want to support if you’re not here to do so. Not the government’s template.

Since Mary and Stan never had kids, they managed to save quite a bit over the years. Also, Uncle Stan was a skilled surgeon, and he left Aunt Mary a sizable Roth 401(k).

He did the easy part, making sure his beneficiaries were (correct and) up to date.

Doing so, alongside TOD designations and a will/revocable trust, can minimize probate as much as possible. These documents are crucial for everyone, but even moreso for unmarried couples because the system is not designed to look at your life and see who’s important to you. To be fair, probate can already drag on longer than anyone would like. They’re dealing with drama from multiple families all day. The preset intestacy templates add some structure and momentum to the probate process.

But all that is worst case scenario. What about life today?

Even while you’re young and healthy, there are considerations to keep in mind. Technically, intrayear gifts still have to be less than the annual gift tax exclusion; $19,000 today. While that’s true, listen, I’m not an accountant or a narc.

And for the rare cases of extremely wealthy couples, the lifetime exemption amount is not portable. While most states disallow any couple to use their spouses’ unused exemption amount anyway, the federal government at least allows the survivor to use their spouse’s unused transfer tax shield for a combined total of $30M. Single filers do not have this added benefit.

I write all this while staring out of my window at the 4 feet of snow the East Coast just got buried under. And I’m sure somewhere in here there’s a metaphor for the four seasons and life.

Maybe I just haven’t found my way of seeing the beauty in the cyclicality of Mother Nature yet. The destruction—frigid temperatures and grey skies—that winter brings, and the rebirth— the fresh start and liquidity—that follows.

Unbeknownst to me, I was having a hard time struggling with this time of year, that was until I saved this absolute beauty. She’s barely 12 weeks old. Knowing the winter storm that would hit us on Sunday was coming, I knew she wouldn’t have survived. Alone, trapped, and scared stiff at a construction site where I found her, I decided to name her Rubble. I brought her home just for the night. Which, of course, is how these things always start.

Death on my mind and a new life sitting right in my hands. Funny how life works sometimes.

Until next time…

On what was supposed to be a great day for SEC football fans, was one of the most horrific events to hit New Orleans—on Bourbon Street, no less— in years.

Despite the senselessness and tragedy, it’s going to take a lot more than that to keep the spirit of New Orleanians down. This is a place that loves to throw a parade for the hell of it!

Knowing this, combined with Mardi Gras parades happening around the same time, I spent my birthday in New Orleans this year. If you know me, and as a boxer who’s typically on a strict diet, you know that my one fatal flaw is that I have a sweet tooth. And boy did New Orleans deliver. I came home with the most New Orleans shot glass following my swamp tour, a dope jacket, and a box of Aunt Sally’s creamy pralines. And I know you’re going to ask… the beignets never stood a chance!

But by far, my favorite experience was the Sazerac House. This part distillery, part museum is filled with history dating back to the Prohibition era as you peruse three floors of trending cocktails from each decade. It’s not often you’ll find a bottle of Sazerac outside of Louisiana, but if you’re a fan of an Old Fashioned cocktail, I seriously recommend trying a Sazerac Old Fashioned.

With that being said, let’s get on to why you’re here. Here is my recap of the top events of 2025.

Tariff-ied

Stumbling out of the gate, the market got tripped up by one little word. “The most beautiful word in the dictionary…” they said. Tariffs.

The overarching idea behind the change in trade policy was that our economy would become more self-sufficient by revitalizing US manufacturing, raising revenue, and negotiating a better trade balance with other nations by using tariffs as leverage: ‘you need us more than we need you,’ economically speaking.

But what really drove markets into the ground was the lack of clarity around implementation and retaliation.

Who would foot the bill for this tax, the importing business or us? Does Foxconn build a factory in the U.S. and allow input costs to drive the price of a new iPhone even higher? Would China retaliate with its own tariffs or non-tariff barriers? At this point, we all had more questions than answers.

And we know how the market feels about uncertainty…

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To date, the word “uncertainty” has been mentioned over 700 times across earnings calls for S&P 500 companies. In the first quarter alone, FactSet recorded that the word “uncertainty” was mentioned 415 times across all calls analyzed.

The start date, so-called “Liberation Day,” was the only piece of certainty we had. Surprisingly enough, it was all uphill from there.

A surprise 90-day pause on the most punitive tariffs calmed markets and gave businesses breathing room to reassess supply chains and pricing strategies.

Volatility left almost as quickly as it arrived.

This was the only real blip of the year. Following that debacle, one could argue AI single-handedly saved the U.S. market this year… not the whole market.

That’s because AI wasn’t the real hero of this story:

The Unlikely Hero

Just when it looked like we were headed for some kind of sustained slowdown in our economy, AI might have saved our stock market.

The Mag7 and hyperscaling alike have held the spotlight for years, driving revenues and earnings higher and higher. We learned this year that AI-related stocks accounted for more than 70% of the S&P returns and nearly all of the capital spending growth since ChatGPT was introduced to the world. It seemed like big tech and large-cap stocks were back on track to be the kings of the playground.

That is, until you look at how international stocks performed this year.

Developed and emerging market stocks benefited from easing inflation, stabilizing currencies, and lower starting valuations relative to U.S. equities. In many cases, investors were simply paid to look elsewhere after years of U.S. dominance.

This chart really highlights the difference in returns between investors who held throughout 2025 compared to folks who sold during April’s market panic.

Courage isn’t the absence of fear. Markets don’t know your motivations, nor do they reward your intentions; they reward patience. Sometimes confronting pain and responsibility is the only way forward.

Diversification isn’t sexy. When the conversation around the dinner table inevitably turns into politics and money, you’re not going to screech diversification. But it works. Diversification across sectors, tax lots, and geographies will protect your hard-earned money and help you avoid all-or-nothing decisions.

Sometimes the best portfolios are the ones that feel a little boring in the moment.

The Fed Reserve’s Independence at Risk

The year began with interest rates sitting at restrictive levels, a deliberate attempt to finish the job on inflation without breaking the economy. Today, rates remain higher than pre-Covid days, but the question has shifted from how high can they go to how long they can realistically stay there.

Sepearately, the Federal Reserve’s independence was put into question after the firing of a Fed governor and the proposed hiring of an industry plant.

In response, all living former Fed chairs urged the Supreme Court to protect central bank independence.

But that’s the side show—why is the Fed’s independence so important?

The Federal Reserve is designed to be shielded from the volatility and pressures of day-to-day politics. Otherwise, what president would want to raise rates during their term? Or at the very least, keep them high when pain starts to ensue. Making it harder and more expensive to borrow money is unpopular, but without that lever, inflation risks becoming a political problem instead of an economic one.

History and research are clear that independent central banks tend to deliver lower inflation and lower long-term interest rates over time. The trade-off is short-term discomfort for long-term stability.

A loss of independence would do more than complicate rate policy. It would undermine confidence in U.S. institutions—and, by extension, in U.S. financial assets.

More of the Same

Are we in an era of deregulation?

Private equity in 401(k)s was pitched as democratizing access to lucrative investments once reserved for the wealthy.

With fewer companies going public due to high barriers to IPOs—often taking 18–24 months and costing tens of millions of dollars in legal and accounting fees—I can respect the thesis that allowing professional allocators to tap into the previously tight guarded retirement plans space to inject resources into smaller, unlisted companies could benefit society as a whole.

SPACs were born from this same impulse: a faster, less burdensome route to public markets when the traditional IPO process became too slow and expensive.

But hold on. Reality has entered the chat.

The middleman always gets his cut. Regardless of how the results of the investments turn out. The always spot-on Downtown Josh Brown writes, “The data-driven conclusion is that investing directly in private equity CORPORATIONS as a shareholder over the last three years would have delivered 151% more than investing in the PE fund strategies themselves, with less fees, more liquidity, and far more dollars in your account.”

Another proposal floated this year was to move from quarterly to semiannual reporting.

Promoters pointed to the steady decline in companies choosing/able to go public and argue that the cumulative burden of compliance, the costs we just outlined, and disclosure and being under the public’s magnifying glass have pushed these firms to stay private longer than ever before.

The counter is that reducing reporting frequency doesn’t eliminate ‘short-termism.’ Focusing solely on short-term results often leads to losing sight of the long-term vision and incentivizing bad behavior. It also reduces transparency. Public markets function best when information flows freely and consistently. Less frequent reporting increases the risk of mispricing and opens the door for bad actors to operate longer before getting caught.

In that sense, fewer disclosures wouldn’t make markets healthier, they would make them less efficient.

Government shutdown

Without pointing a finger, the main holdup was a standoff over budget priorities. While this is certainly not atypical for the opposing sides of the aisle, it still resulted in the longest recorded government shutdown, lasting more than 40 days.

During the shutdown, non-essential roles were furloughed, and essential workers—like TSA agents and air traffic controllers—worked without pay. This led to major airports across the country experiencing severe delays, and more than 1,000 flights were canceled. TikTok showed videos of TSA waitlines basically in the parking lot at George Bush Intercontinental Airport in Houston.

The shutdown cost roughly $11 billion over that period.

More importantly, key economic data was delayed for weeks, forcing policymakers to make already difficult decisions with less visibility.

Powell summed it up during the October Fed meeting: “What do you do if you’re driving in the fog? You slow down,” he said. “So I’m not committing to that. I’m just saying it’s certainly a possibility that you would say, we really can’t see, so let’s slow down.”

However, the chart below tracks how the S&P has performed during past shutdowns.

8 of the past 11 years with a government shutdown still closed with a positive going back to 1980. Despite the frustration and impact it may have on government employees’ lives, for investors, this is a reminder that these events are just a feature of a two-party system and ultimately, more noise for long-term investors.

Despite how bad the year started, we damn sure finished strong.

The reason I called it this year The NeverEnding Story is because it reminded me of the 1984 Wolfgang Peterson film. Just like the Gremlins, I can’t believe I was once scared of this great movie. But nonetheless, the takeaways from this year are the same ideas I remember (… ok, Googled) from the movie:

“In the beginning, it is always dark.” I know the first quarter certainly seemed like it spelled trouble for the rest of the year.

April’s test reminds me of when Atreyu, the hero of the story, comes face to face with G’mork, a leopard spirit that was sent to kill him. But Atreyu claims he’s a warrior. He won’t back down so easily in the face of death, yet he also knows that it’s either G’mork or the Nothing that’s eating Fantasia alive. When he asks why is this happening, G’Mork snaps: “Foolish boy! Don’t you know anything about Fantasia? Fantasia has no boundaries… it is a piece of the dreams and hopes of mankind. Therefore, it has no boundaries!”

When some of you look at the market, you might see numbers, percentages, or godforbid Bollinger Bands. But I see retire in 20 years. I see college tuition due in 2043, or I just want my family to be okay if I suddenly lose my job. It’s the never-ending story, that’s why it has no boundaries.

The Nothing, the void, or in our case a 20% retreat from peak to trough, only grows when people stop believing. It’s nothing short of a common occurrence, but still, a lack of faith in the system is a virus that eats it from the inside out.

The upside is in staying consistent in the face of fear. Our wise and incredibly optimistic luckdragon assures us, “Never give up and good luck will find you.”

On a personal note, in March I watched the New Jersey Golden Gloves regionals as fighters prepared for the state finals. I went to scope out the competition. I liked some of what I saw, but if winning a state championship is the mission, I’ve got a lot to learn and improve upon. Stay tuned.

I ran the Brooklyn Half Marathon in April. I was supposed to do another, the Rocky Run, this November but I didn’t, which was totally a user error. So I owe you all a race.

I made it to Chicago and stopped by Mr. Beef’s. If you’re a fan of the Hulu show The Bear, you feel like you’re home as soon as you step inside.

Our story doesn’t end here.

Last week was my cheat week, so now I have to spend the rest of the year working it off.

Does anyone else have family or a significant other who puts up the Christmas decorations immediately after Halloween or Thanksgiving? The older I get, the more I realize Thanksgiving gets treated like some second-rate holiday. It barely has a chance to be a holiday before it gets replaced by Big Christmas.

Anyway, I wanted to catch you up on a long-overdue story.

Back in September, Future Proof 2025 was another amazing year, with friends, music, and thought-leaders worth traveling across the country to see. The first Future Proof in 2022 was not only my first time in LA, but my first time in California. Since then, I’ve made it a point to try something new and/or explore different attractions in SoCal.

Looking back at these pictures only makes me miss the summer even more.

Anyway, coming from the East Coast, where your Uber driver is most likely silent and on the phone at the same time, I guess I’m always a little jaded by the chatty bunch I typically get in Cali.

This year, as I’m on my way to the airport, my Uber driver—let’s call him Mark—and I are trading stories about this and that, eventually getting around to what we do on the outside.

If I’m remembering correctly, he owns an audio installation and repair business specializing in high-performance cars. Audis, BMWs, Porsches. And high-end trucks like your Raptors and Rams. As he explains, it’s a premium service, but his customers are high rollers and car enthusiasts who have no problem spending thousands of dollars to upgrade their stereo systems.

But what really stuck out were two things he shared with me.

First, his business partner recently passed away (Complete strangers share these kinds of things with me all the time. Don’t ask me why).

They had an informal agreement that his partner would buy him out, and Mark would retire soon.

Well, that’s not happening anymore.

But he also shared with me that, although he has employees—each playing a specific role on the labor side of the business—none are really equipped to be business owners. At least not yet.

Instead, he would like his son to take over the business. His son… who is 28… and couldn’t care less about his dad’s business.

I can’t confirm that it’s all true. Maybe he was looking to guilt-trip this out-of-towner into leaving a bigger tip. Perhaps. But let’s assume he was telling the truth.

Regardless, it’s all very fascinating and a microcosm of major forces at play here.

The great wealth transfer is well underway, and as a member of my firm’s trust and estate planning team, I have seen a mix of good intentions, some really creative planning, some non-existent planning, and realities many families would rather not talk about until it’s too late. But don’t get seduced by the eye-popping numbers.

The $84 trillion-dollar (or whatever it’s up to now) wealth transfer isn’t going to be as beautiful and majestic as the headlines make it out to be. There’s going to be some serious bumps and bruises along the way.

Here’s how I know…

The Trillion Dollar Wealth Transfer

Between now and 2045, trillions of dollars in assets—think retirement accounts, homes, businesses, investment portfolios, trusts, and insurance proceeds—will move from older generations to their heirs, charities, or the government.

There have been multiple attempts at putting an exact number on this tectonic shift. You may have read $70T, $84T, and now $124T by now.

Of those trillions of dollars exchanging hands every year, Cerulli Associates tries to quantify just how much each generation could inherit over the coming decades, with $18T going to charity.

While trillions with T is a big number, much of it is concentrated among a small subset of families. This is our first fork in the road. When you zoom in, the average person isn’t inheriting millions because the average person doesn’t come from an extremely wealthy family. A disproportionate share of this wealth sits with families already in the top 10%, and increasingly, the top 1%. In other words, the wealth transfer isn’t going to be this great democratizer. It’ll likely carry over the inequality we already see and feel.

But concentration aside, the next crossroad is execution.

If you’re like most American families, a house, a few investment accounts, and an IRA are still at play here. It may not be life-changing, quit your job tomorrow, money, but every little bit helps.

The next challenge will be avoiding burdensome taxes on that wealth.

Yes, actual taxes, but also the time spent unwinding and redistributing an estate. Family feuds, court fees, and attorney fees are just the start… if you let it.

As we continue to become an increasingly opulent nation, for some families, passing wealth won’t be as simple as just writing a Will.

It will require extensive planning. Lifetime gifting, layering different types of trusts/entities, stress-testing liquidity needs, preparing for Fed and state-level death taxes, or some combination of each. As the current holder of this wealth, it will be their responsibility to ensure that their heirs are in the best position to receive it.

But this is where your grip on the wheel can get a little tighter.

Even the best intentions can run into forces bigger than all of us: generational differences.

A Generational Divide

According to the U.S. SBA, there are about 35 million small businesses in this country as of 2024-2025.

Still, only ~19% of family businesses transitioned to the next generation in the last five years. The numbers show that most small businesses don’t survive the founder’s exit. Why is that?

The culprit typically falls into one of two camps: a lack of succession planning on the front end and/or a lack of interest on the back end.

I fear my driver, Mark, is dealing with each issue.

Older generations built wealth through the homes they bought for three pennies and lint in their pockets, pensions and retirement accounts linked to some of the great bull markets, and business ownership. But they also value hard work, loyalty, and the pride of building something with their own two hands.

We grew up in a completely different world.

Broadly speaking, the younger generations value flexibility, autonomy, and speed with less hassle. We tend to opt for experiences over material things because material things don’t have sentimental value like they used to. Most tangible items have become cheap, undifferentiated, and hyper-commoditized. But let’s not confuse the word “cheap” with inexpensive, though.

Let’s face it, today’s definition of success is being young, with social capital, and having as much money as possible. And with that as the baseline, it changes how we view risks.

So what kind of effect will this have on markets?

Lauren Sanfilippo, a senior investment strategist at Bank of America, writes, “Younger investors are more open to new financial vehicles, including alternative investments.” As much as we can warn people that private equity and crypto in 401(k)s may not be the right approach for everyone, some people will still need to learn for themselves.

We’ll see investor preferences shift as these dollars migrate from older, more risk-averse households to younger, digital-native households with longer time horizons and a deeper comfort with tech-driven solutions like direct indexing, tax-loss harvesting, and auto-rebalancing.

But one thing is for certain, human behavior won’t change.

Viral manias will create scorching demand, which will create new bubbles. And new market dynamics won’t always act like the old ones. Will have our own vomit-inducing drawdowns and “is this the top?” headlines, but with time on our side, a rising tide should lift all ships.

The Yellow Brick Road

Now, I know nothing about Mark’s son’s background, if he has siblings, or their family dynamic, for that matter. But another detour that can come up for families—especially when leaving intricate yet less liquid assets like homes and businesses—is to simply leave things to their kids equally.

Inheritances don’t have to be “equal” to be fair.

David Handler, a distinguished trust and estate attorney out of Chicago, writes,

“Take a client with a family business in which two of their children were involved and a third was not. Dividing ownership equally among all three children would likely create unnecessary conflict. Instead, the client could leave the business to the two children who were active and provide the third child with different assets of comparable value, such as cash or life insurance. And the amount left to the third child doesn’t necessarily have to equal the value of the business, which will change over time.”

But, as we’ve seen, what if the kids just don’t want the business?

Some owners end up shutting the business down and liquidating whatever’s left.

Others know they have too much tied into it. Whether it be employees or customers, who rely on the business with or without them. They’ll pursue a sale to a private equity aggregator or strategic buyer who can absorb the costs and keep the lights on.

And more often than you think, they/their kids are hopping on sites like BizBuySell.com. They want a clean exit. The kids have zero interest in running payroll, marketing, and vendor relationships for a business they didn’t start. Services like this are all the more evidence that retirees are looking for liquidity and literally any way out.

Although a trillion dollars of wealth being passed down sounds great—especially when the younger generations are desperately trying to find ways to afford an enjoyable life, buy homes, and fund the education of their own children—the road to the trillion wealth transfer isn’t paved with gold.

It’s going to be a little bumpy, filled with detours, and some wrecks so bad you can’t take your eyes off it.

But it doesn’t have to be.

Above all, I think the biggest fallacy is that the headlines make it sound like it’s finite.

Like this generational occurrence will somehow slow down or stop altogether by a certain time. Passing down wealth and values will always be happening under our noses, whether we hear about it or not. It’s the human condition. This is why this will be a conversation that goes on forever.

So get ahead of it.

The best way to get ahead of all this is to talk to your kids. Have family meetings.

Have the hard conversations about why assets are divided a certain way, why a business goes to one child, or why charitable giving is part of the plan. Better now, while you have a voice, than leaving it to vague writing in documents they don’t understand or have the bandwidth to parse through.

If you’re stuck, bring in a professional. You don’t have to do this alone.

“Some films are completely made by their last scenes, and “Anora” is one of them.” They took the words right out of my mouth.

If you want to see a prime example of wealthy parents’ worst nightmare, watch this movie.

I don’t want to steal the film’s thunder, because words won’t do it justice for how captivating it was from start to finish. It was a beautiful mix of irresponsibility meets enablers, meets the quiet dysfunction that can follow second or third-generation wealth. The movie really starts about 42 minutes in—possibly the happiest day of her life—when Ani quits her job, two middle fingers in the air on the way out, waking up to a life of flying private to Vegas to spend the weekend with Vanya, her new billionaire husband, and his “friends.” The problems only get juicier from there.

The entire story is a great reminder that, whether you come from money or not, problems are problems.

So, if you’re a parent of little ones, this post is especially for you.

Why Worry About This At All?

When it comes to designing your family’s estate plan, don’t sacrifice good for perfect.

What I mean by that is this: the decisions you have to make—who will carry out your wishes, who receives what, and how they receive it; should your heirs receive funds outright or in trust? If in trust, should they have access at certain ages, or should the assets remain protected for life—are all mentally draining.

These are the kinds of questions that keep parents up at night, and one of the main reasons folks keep kicking the can down the road.

Part of the difficulty is that these decisions require you to predict and, to some degree, control the future. On the other hand, you could take a hands-off approach, “they’ll get what they get. Once I’m gone, what they do with it is up to them.”

Fair. I get that. Albeit, parents with that kind of mindset are often those whose children are already grown and (hopefully) wise enough to make sound decisions.

When your kids are still young, your estate plan becomes the stand-in for you. It’s how you continue to guide and provide for them when you’re no longer here.

But that raises the big question: how do you provide financial security and structure without killing their ambition or independence?

You don’t want to leave them unprepared. But you also don’t want to hand them a blank check.

So what do you do?

I’ve seen two effective strategies that strike the right balance.

Strategy One: A Letter of Intent

The first strategy is to include a letter of intent in the document itself.

The first time I saw it in practice, I had to take note. Here is an example of what I believe to be a beautifully written note from a grandma to her two grandchildren:

Dear (grandsons), we created this trust not only to support your future, but to protect it. It’s our hope that this gift serves as a launching pad, not a safety net. You may not always see it, but life brings risks. This trust shields you from some of them: lawsuits, toxic relationships, unwise financial decisions. The rules are here not to limit you, but to give you tools and boundaries to grow your future. You’ll receive guidance, support for your education, and rewards for major life achievements. But you’ll also be challenged to learn, to stay responsible, and to protect what’s been built for you. You’ll be asked to think critically before taking money out. That’s because every withdrawal is a choice, one that could carry long-term consequences. I trust you’ll grow into wise, thoughtful stewards of this gift. This is your legacy, and it comes with our love, trust and confidence in who you’ll become.

It’s short, real, and direct—something a beneficiary can actually feel.

This revocable trust is structured in a way that upon grandma’s passing, two irrevocable trusts are created for the boys, providing both protection and rewards at certain milestones (college graduation, marriage, first home assistance, and a few others). It goes on to request that any distributions over a certain amount, $50,000 in this case, be in writing for the trustee to determine its necessity.

A simple message like this is a bridge between the legal and the personal. It humanizes what can otherwise feel like a sterile, rule-filled document.

It also gives your heirs context: why the plan was built this way, what you hope for them, and how they can make the most of it.

Strategy Two: Your True Legacy

The second, and definitely more cumbersome, strategy is an ethical will.

An ethical will is a personal, not legally binding, document that passes down values, life lessons, and memories to loved ones. It has nothing to do with assets (yet).

Some call this your true legacy.

In the ultra-high-net-worth space, there’s a similar concept to this known as an Investment Policy Statement (IPS). An IPS’s purpose is to be able to be picked up by a remote descendant of yours, and they know exactly how the family’s wealth was created, the purposes of the various Trusts created, key players, and how it all works. Many families opt to include things like their family mission statement or a charter around giving back.

Because let’s be honest, legal estate planning documents aren’t very creative.

Yes, you help design who’s in charge, who gets what, and how they get it; however, the language is written in very specific legalese to be read and interpreted by any practicing attorney. It’s pretty cut and dry.

Your Ethical Will is the color to this black and white procedure.

It’s where you get to share why you made the decisions you made, and how you hope your children will carry them out.What would an ethical will say?

1. What was your childhood like?

   • What is something you learned the hard way?

2. Your experience learning about work

   • How did you obtain this wealth – how do you view “work” / ways to earn a living

3. Your experience learning about money

   • This could be something you learned yourself, your parents taught you, what being married has shown you.

4. Your experience with making mistakes (about money, work, prioritization of family, etc.)

   • First dumb thing you spent money on? Did you regret it? How did you determine it was unnecessary even if you wouldn’t have changed anything?

5. What would you suggest they do to have a meaningful or fulfilling life?

   • This is more philosophical – take money out of the picture – what actions make you feel complete? (ex. Helping people in a tough situation, teaching, coaching, researching a particular topic, building something with your hands, etc.)

6. What would you suggest they do differently, earlier, or later than you did?

7. What would you tell them to avoid?

8. Why did you choose a particular person (or institution) as trustee/executor versus another?

If your family history is especially rich or layered, there are even services that can help you preserve it. Storyworth, for example, can turn those memories into a beautifully bound family book—something your children and grandchildren can literally hold in their hands.

God willing they’re still around, start by asking your own parents or grandparents questions about their lives. Learn their stories before writing your own. You might be surprised by what you find.

Leaving A Legacy, Not A Liability

At the end of the day, it usually comes down to one thing: not wanting to create a monster with wealth.

If I learned (at the very least, confirmed) anything from the movie Anora, it’s that money can act like a drug in the wrong hands. Letting the money make you, and not the other way around.

Spending money is the easy part. Spending it on the right things—things that preserve value and your family’s values—is the hard part.

I’ve talked before about how true Generational Wealth is created. Not just through the assets themselves, but paired with structure, protections, and avenues for guidance along the way. When managed correctly, this is how wealth can pass through multiple generations.

These strategies won’t be for everyone. But they’re worth considering if you want your estate plan to do more than just distribute money.

They’re for people who want their final gift to reflect more than just numbers on a screen.

Ask your financial advisor whether this is something you should be considering.

One could argue that AI has single-handedly saved the market.

Beyond valuations, it was the promise of what AI will do for the American workforce that drove these numbers higher.

As Ben Carlson put it, “Would we have seen an economic contraction if our tech overlords didn’t go on an insane AI spending spree from there?,” following the mental reset markets took from February to early April.

As of September 2025, in addition to Warren Buffett’s Berkshire Hathaway, there are eight tech companies within the S&P 500 that have a market capitalization exceeding $1 trillion. Chart Kid Matt helped bring this to life, showing that the total market cap of the Mag 7 is now 35% of the total market cap of the S&P.

Valuations are high. Breadth is narrow.

According to Howard Silverblatt, through the first half of the year, the information technology sector, led by a handful of big names, accounted for almost 54 percent of the S&P 500’s 8.6 percent total return. Almost 70 percent of the total return of the entire index.

The question, and some investors hang up, is whether we are at or nearing the top?

The question as old as time. Who knows? That kind of data is only known after the fact.

But the cracks are showing.

This tweet / X’d (guys what are we calling these things?)… this X-a-sketch by Augur Infinity highlights how the U.S. has had one of its worst relative runs against the rest of the world since 2009.

Commentators have flagged frothiness in U.S. equities, asking what happens if these mega-caps fail to deliver on their promises, and have started making bold calls about whether the “U.S. exceptionalism” trade is running on fumes.

All fair. If you think we’re near a peak, here’s the answer: diversification.

Diversification of sectors.

Diversification of tax lots.

Diversification of geographies.

Probably not the answer you were looking for, but diversification works. It doesn’t always feel rewarding, but over time, it plays its role.

More Evidence for My Case

For more than a decade, U.S. stocks—powered by a handful of tech giants that we know and love—have overshadowed the rest of the world. More recently, the Mag7 has dominated headlines and portfolios alike, carrying the S&P 500 to new highs.

Michael Cembalest from JP Morgan writes, “AI related stocks have accounted for 75% of S&P 500 returns, 80% of earnings growth, and 90% of capital spending growth since ChatGPT launched in November 2022.”

He highlights the soaring debt-to-equity ratio of these large tech companies, particularly Oracle, suggesting that the time it takes a firm to convert its investments in assets (AI infrastructure) into sales could be ripe for change.

For most of my career, the US large-cap sector has seemed like the only rational place to park your money.

And for years, global allocations, investments outside the US, looked like dead weight in portfolios.

Now, the story has flipped.

International equities haven’t just caught up with U.S. stocks this year—they’re outpacing them by a wide margin.

Take South Korea (EWY), for example. Year-to-date, the country’s index is up 54%! Far exceeding the S&P’s lackluster 12.7%.

The lesson here is that you can make money in other stocks even if they’re not the bold print headlines of today’s stories.

Those of us who stuck with a diversified approach haven’t exactly always felt rewarded. But moments like this remind us why we diversify in the first place.

Because no one market regime wins forever. That goes for businesses, factor strategies, sectors, and geographical regions.

Recency Bias:

Markets move in cycles, not straight lines. No one knows how long international leadership will last.

But diversification remains the closest thing we have to a free lunch.

Diversification isn’t about predicting winners, it’s about owning exposure to multiple potential winners.

Holding international stocks doesn’t just give you exposure to new growth—it can actually reduce overall portfolio volatility. By blending U.S. equities with non-U.S. markets, you’re smoothing out the ups and downs that come with having all your bets in one place, which ultimately helps you stick with your portfolio for longer.

Vanguard, Portfolio Perspectives: International equities: Will the performance continue?

Vanguard research backs this up, showing that a 30–40% allocation to international equities optimally reduced volatility within U.S.-heavy portfolios.

And don’t stress too much over finding the perfect split between U.S. and international stocks, just make sure you have meaningful exposure to each.

The exact numbers will shift over time, but simply keeping a healthy mix is what delivers the benefit.

It also combats the recency bias many of us have.

We tend to assume that what has worked recently will continue to work indefinitely. The past 15 years have reinforced the idea of U.S. exceptionalism—especially in the tech sector.

But history says otherwise.

I love showing off this chart because it really tells the unbiased story.

Going back to 1971, it’s basically a coin flip whether U.S. or international markets outperform in a given cycle.

Leadership shifts depending on which sectors or structural advantages are in favor—tech dominance can lift U.S. equities, while industrial growth, commodity strength, or favorable demographics can drive international outperformance.

This year, international stocks remind us that the world is a lot bigger than just the U.S. market.

Immediately regretted it.

But it did confirm something for me.

Look, I’m not going to tag the video or comment on the guy who was reposted in the video because, one, this kind of misinformation is harmful. And two, this isn’t a slight against him. He was a young guy, likely just regurgitating what he saw in someone else’s video.

But for context, here’s what the video says in a nutshell:

Step 1. Open a Trust

Doesn’t specify what kind of trust. Nor the barriers to entry: finding and affording the attorney, administrative costs, etc.

Step 2. Buy a $1M life insurance policy

Doesn’t specify what kind of policy. But let’s assume he means a whole life policy with a death benefit of $1M based on where this is going.

He also says this insurance will cost you ~$100/m, which he was likely referring to a term policy for a young person, which very well could cost you $100+/- a month. But that’s not what this is.

Step 3. Put the life insurance inside the Trust you just opened

Step 4. “Now the Trust fund is worth $1M”

Now this is where it gets harmful and deviates far from the truth.

Neither the trust or the life insurance policy is “worth” the value of the death benefit. Unless it’s a fully paid-up policy, if you stop paying the premiums on said policy, you’ll quickly find out how much it’s “worth.”

Step 5. Do what the ultra-rich do — borrow against your $1M trust fund

Let me stop you there.

This is why I hate “Generational Wealth.”

Not the idea of parents wanting more for their kids. Not the act of saving, investing, and passing something on. Those things are good—essential even.

I don’t hate generational wealth.

I would argue that most things I do are in the pursuit of financial freedom and being someone my future children can look up to. Not to mention, as young men, we’re often told our value in this world is contingent on our financial success. So I’m not immune to the idea.

It’s not the concept I take issue with.

What I hate is the way the term has been hijacked. It’s morphed into a sort of marketing buzzword used as a tagline to sell you some bullshit strategy.

A slogan used to sell unsuitable financial products, quick-fix strategies, and empty promises—especially to the very communities least equipped to fact-check it.

It’s the manipulation of people’s dreams. The false binary that you’re either “creating wealth” or “stuck in poverty”—as if there’s no progress, growth, or nuanced middle ground in between.

How many know a $10,000 Roth IRA left to your child is generational wealth—but that rarely gets talked about in that way.

As a financial advisor, and as someone who comes from one of these communities, I’ve seen firsthand how this vague, overhyped phrase can do more harm than good. And usually to the exact people it claims to help.

After seeing this trend and cringing every time I saw someone blatantly lie was how I decided to blend my curiosity with my personal experiences to learn how it was actually done.

Who’s In Your Ear Matters

Only ~33% of adults worldwide are financially literate.

That gap matters.

Because when people don’t understand the mechanics, they rely on nontechnical cues like stories and fearmongering.

Jason Zweig writes, “Your feelings blind you to the financial reality of the situation.”

And when your feelings take the driver’s seat, you become an easy target. People from our community are sold unfitting insurance policies, coated with the word “investment” and “be your own bank”, or come across some get-rich-quick courses under the promise of “generational wealth.”

Who we listen to about money makes a huge difference.

Just because your Uncle Mike invests in stocks doesn’t mean he should be giving financial advice.

No offense, but your parents and family members may not always be the best people to give advice about money. To be fair, they likely have your best interests in mind more than anyone. Yet more and more people aren’t just getting advice from their family—they’re getting their information from social media.

If I had to guess, anyone who’s a millennial or younger is primarily getting their information from TikTok, YouTube, and Instagram over the news or even the WSJ, NYT, etc.

The Philadelphia Fed reports that a majority of Gen Z (76%) and 65% of millennials seek financial advice on social media; other surveys peg ~10% of all U.S. adults as active followers of fin-creators. Their publication How Americans Use Social Media for Financial Advice states:

“Surveys indicate that people, especially those in younger generations, are increasingly turning to social media platforms for advice on various financial topics, including budgeting, saving, and investing. For example, TikTok has been rapidly growing as young adults’ go-to source for financial information, with content tagged with the hashtag #FinTok reaching more than 1.4 billion views.”

Will this be harmful going forward?

I once heard that if you want to make money, be really good at selling one of three things: fast weight loss tips, how to make more money, or advice on how to live longer.

It may become more difficult to discern what’s good, effective advice from bad advice based on followers and likes alone. Real-time data on search trends and AI automation tools will allow the ones looking for a quick buck will be able to capitalize on what the people think they want to hear and distributing across multiple platforms with the click of a button.

There are no state troopers on the internet. Generally speaking, registered financial professionals have a ton of compliance and regulatory hoops to jump through. And if we’re being honest, the unfortunate truth is that many of us in this industry who have the credentials are terrible content creators.

It’s a tough question.

I think yes and no. It would be hypocritical for me to say all financial content creators are bad. Some are great, and I look up to them. I think as the RIA industry progresses and regulations around social media use laxes, more and more advisors will tap into posting all forms of media (blogs, podcasts, TikToks) and building a community around it. These nuggets shared will be much more accurate and beneficial for that specific target audience.

We’re experts, not showmen.

Where, on the other hand, unregistered content creators have mastered the art of capturing attention. They have much more control over what they can say.

For me, it goes back to incentives and credentials. What do they stand to gain by giving you this information?

How to Actually Create Generational Wealth

My personal distaste for the term, which was overused and oversold, influenced my decision to marry my personal experiences with understanding how it was actually accomplished.

Which is through effective estate planning.

It looks like:

• Teaching your kids how money works

• Leaving a paid-off car

• Funding a 529 plan

• Modeling healthy financial behaviors

Intergenerational wisdom is just as powerful as intergenerational assets.

In the end, I don’t think #estateplanning is going to blow up on TikTok. It’s just not sexy.

Probably because the words “estate” or “inheritance” are foreign words to the average person.

For those of us striving to leave some sort of inheritance, our goal isn’t just to leave an inheritance and an estate behind. It’s to avoid creating a monster. Because if you hand your kids wealth without wisdom, you’re not setting them up for success—you’re setting them up for self-destruction.

This is where tools like (more on this in a future post) an Ethical Will—passed down values, stories, and lessons about life and financial decision making written for the next gen—matter just as much as the assets themselves.

Generational wealth done right isn’t just about what you own. It’s about education, protection, and intention. That’s the actual blueprint for sustaining wealth across generations.

Everything else? Noise.

These folks typically earn six figures, have solid careers, and still feel like they’re running on the treadmill of life with no financial progress.

The EPI, a non-profit think tank focused on economic equality for all, has a family budget calculator that shows that the typical monthly budget of a family of four in the New York metro area is $12,784! The Bay Area in California is even higher, coming in at $17,621.

If you can relate, just know, it’s not just you. We’re all feeling it.

Being rich and feeling rich are two very different things. Members of the Gen Z generation say you need $1.7 million to be wealthy. Millennials and Gen Xers say $2.1 million. Baby Boomers report $2.8 million. Regardless, on average, this is a 21% increase from 2021.

The point is: feeling “wealthy” or “rich” is a moving goalpost.

This may never change.

Over the last three years, we’ve experienced higher inflation than in the decade preceding it. And while I’ll always defend Jay Powell and the extraordinary work he’s done in his tenure, it’s hard to ignore the toll higher interest rates on high-ticket items have had on the recent economy.

The national average car payment is now $745 for new cars and $521 for used vehicles. And even with the carrot of an interest deduction on auto loans dangled, most won’t benefit from the OBBA provision offering up to a $10,000 deduction on U.S.-made cars. According to Caribou, “only 2.8 million Americans—less than 3% of the 100 million with auto loans, will qualify for the deduction.”

Home prices and mortgage payments? Up nearly 50% since 2017.

In July 2017, the median home price in New Jersey was listed at $330,601. Today, it’s closer to $569,314.

Assuming you put down the same 20% to avoid PMI:

• 2017 mortgage: $1,429/month

• 2025 mortgage: $2,966/month

And this is all before everything else it takes just to stay afloat in this country.

And now, it’s evident that tariffs are slowly trickling into our normal lives. Despite PPI staying unchanged month-over-month, we see that the price of imported goods has eclipsed U.S.-made products.

Prof G Markets, CPI vs. PPI: The Crucial Inflation Detail Everyone’s Missing

And my colleague Callie writes, “According to these daily receipts, tariff collections have jumped from $9 billion to $28 billion per month this year, boosting the effective tariff rate to around 10% – near the highest in a century.”

This may be good in terms of tax receipts—especially considering the corporate tax rate is permanently set at 21% by the OBBA—but not for you and me. Let’s not kid ourselves, higher prices are sticky, and somebody will have to foot the bill.

And it’s typically not corporate America.

Net Zero

When I talk to families who feel this way, I call it operating at “Net 0.”

Net zero means that after all your expenses and savings, you have nearly nothing left over in your checking account.

There are really only two ways to reach net zero:

By choice—You automate savings and investing first, then spend what’s left. Your goal is to make sure every dollar has a purpose.

By force—You get to the end of the month, and everything’s gone. You may not even know where it went, but you know it’s not there, even if it doesn’t feel like frivolous spending. It just disappears.

So what’s going on?

What could be the issue?

I’m not here to spend-shame anyone. But here are the usual suspects:

1. The need to have everything.

We’re living the American Dream! As I mentioned in that post, we’re navigating a world where we can do almost anything or have it delivered to our doorstep—convenience has never been more accessible. But with that accessibility comes expectation from others.

Kids’ sports and activities.
The car (Guilty!)
The house in the best neighborhood.

We convince ourselves that these are baseline needs. But even among those doing well, it still doesn’t feel like enough.

In other words, the middle-class don’t feel rich—not because they aren’t doing well, but because the pressure to keep up (or keep spending) never stops. And when you live in the big metro areas, it’s constantly in your face.

As Nick Maggiulli put it:

“The upper middle class are learning this the hard way. They are finding out that the exclusive wealth they thought they had isn’t so exclusive after all. What was once a marker of distinction has become a victim of popularity.”

(CHECK OUT HIS NEW BOOK)

Maggulli’s post highlights that being Level 3 rich just isn’t that uncommon anymore. And retailers know this. That’s why they don’t have to lower prices to get more sales. They know you’ll spend the money anyway.

My takeaway: adopt the mantra, “all that I have is all that I need.”

2. Budgeting

I know the term “budgeting” makes people want to throw up—but a lack of oversight over spending is a major issue.

Tools like Rocket Money, YNAB, or even just a simple spreadsheet can help. The idea isn’t to nickel-and-dime yourself, it’s to know what’s going where.

Once you can identify what’s left over and even areas you could be more efficient, you can sneak in ways to automate your investing. Even if it’s only small amounts. For me, if that money is not redirected, it will find a way to get spent. This is why I also strive for net zero, but I don’t feel guilty for spending on what I want because I know my monthly savings target has been hit. In theory, it will only go up from here as my income increases.

3. No plan

Even if you’re a disciplined saver, without a financial plan, there’s no way to track progress. You’re just saving… and spending the rest. Net 0 by choice, with no purpose.

A real financial plan gives you:

• A clear view of your assets and income

• Defined goals and priorities

• A roadmap to get there

• Proper asset allocation to match those goals

• Progress tracking along the way

Whether you know it or not,

If this is you, you’re not alone.

Reducing costs isn’t just hard—it might require downgrading your lifestyle, and trust me, no one wants to do that.

You work hard, and I’m a big believer that you deserve to have something that reflects that hard work does eventually pay off.

Everyone says not to buy the new car—because it’s a status symbol, it depreciates fast, and it slows your path to building wealth. And they’re not wrong. But if you can afford it, understand the tradeoffs, and it genuinely brings you joy… why not? Money is a tool. And sometimes, that tool is best used to improve your quality of life—not just your net worth.

But once you get past the tangible things, if you want to start making real progress, you need a few things:

A spending plan and finding any areas where you can automate saving and investing to get you to net zero the right way. A financial plan to know where you were, where you are, and where you’re going. And realize that someone looks up to you. Whether you know it or not, plenty of people wish they were in your position. You should take pride in that.

Finally, do something in your life that fills your cup outside of money. Do something that makes you feel complete.

Maybe that means you reduce your commitments. Josh Brown wrote No More Side Quests. He wrote it in 2021 and it still hasn’t left my brain. Similarly, Blair wrote a great post titled “The Superpower of Saying No.” Make sure you check these out.

Whatever it is, do it for you.

If this all resonates with you, it might be time to work with a professional.

He started teaching English as a second language to students around the world and came to the realization that it was less expensive and made the time zone differences easier to manage. Not to mention more exciting than staying in Georgia. Now, bouncing between Vietnam and Thailand, chasing a version of freedom that didn’t come with a 401(k) or health insurance.

It came with something else: autonomy, making the world a smaller place, and life at a slower pace.

I took the complete opposite path.

I chose the more traditional route—got a job in NYC, chasing financial freedom, and dedicated myself to building a future where my children (his nieces and nephews) won’t have to live the life my brother and I did growing up. For me, the financial industry and writing have become a ticket out.

Two people from the same place. Two completely different paths.

We’re both chasing different versions of the same thing: the new American Dream.

We all know the old version.

The white picket fence. The large suburban home. The luxury car. The big-screen TVs glowing in multiple rooms. The safe, reasonable nine-to-five. The corner office.

Yeah, we threw that script out the window.

Why? Where did that really get us?

Student loan debt that will outlive most of us. A housing market few can afford to enter. A political system that can’t agree whether our country is headed in the right direction or not, while simultaneously hellbent on driving up the federal deficit.

Are we just f*cked?

I don’t think so…

The fantasy of the American Dream didn’t die. It grew up. It expanded. It stopped being one-size-fits-all. Today, it’s about financial freedom and autonomy. And for many of us—especially my generation—that dream only feels achievable through technology, creativity, and influence.

Which brings me to my generation: Gen Z.

Gen Z’s Nightmare

Each generation has lived its own version of the American Dream.

Some ‘made it’ and left them wondering, Isn’t there more to life? And then there’s a growing group who look at all of it—the house, the job, the debt—and think, why would I spend my life chasing someone else’s dream, just to end up burned out and barely getting by?

The Silent Generation and Boomers largely achieved it. They bought homes at affordable prices, enjoyed pensions, and experienced steady wage growth. Many were in their 20s between the 1940s and 1970s—what my colleague Nick Maggiulli describes as one of the greatest times for homeownership.

Of Dollars And Data: Has the American Dream Become Unattainable?

Gen X had a more mixed reality. Some thrived. Others struggled through multiple recessions. Many are now heading into retirement wondering if they saved enough to get them through to the other side.

They were told to keep their heads down, grind, and success would follow. But the numbers tell a different story. According to the Economic Policy Institute:

“Starting in the late 1970s, policymakers began dismantling all the policy bulwarks helping to ensure that typical workers’ wages grew with productivity… From 1979 to 2020, net productivity rose 61.8%, while the hourly pay of typical workers grew far slower—increasing only 17.5% over four decades (after adjusting for inflation).”

We’ve watched the effects of those policies play out for decades, yet the message remains the same: work harder.

Sure, technology and innovation have made work more efficient and increased total output. AI is slowly becoming an integral part of my job, and I’m sure it’s not just in my industry. But what about wages? They’ve flatlined. Meanwhile, the cost of education, housing, and childcare has skyrocketed.

Millennials arguably got hit the hardest. Many entered the workforce during the Great Financial Crisis. They’re now burdened with student loans, flat wages, and a housing market that had already begun to slip out of reach. To no fault of their own, many relied on their parents just to get by.

And then there’s us—Gen Z—the first generation to grow up fully aware that the rules of the game have changed.

Despite being the most educated generation, we’re also one of the most financially strained. Megan Carnegie at the BBC notes that:

“At Gen Z’s age, older people worked 40 hours a week and made enough money to buy a house and have barbecues on the weekend,” says Corey Seemiller, an educator and TEDx speaker on Gen Z. “Gen Z works 50 hours a week at their jobs, and another 20 hours a week side hustling, yet still make barely enough to cover rent.”

Ask someone my age and they’ll tell you this: hard work doesn’t guarantee better pay. That promise has broken down.

The reality is, 74% of Gen Z workers say they would leave a job due to low pay. And when it takes an estimated $138,000 a year just to live comfortably as a single person in NYC, who can blame us?

This is likely why we have the stigma of being lazy. But the reason for this mindset could be that we see generations before us breaking their backs for years, only to scrape by. Combine that with the cost of the basic wishes of life—education, a starter home, or raising a child—rising much faster than our wage trajectory could ever reach.

We’re not lazy, we’re paralyzed by fear.

We’re navigating a world where we can get whatever we want delivered to our door (thank you, Jeff Bezos and Tony Xu)—but real financial freedom feels farther away than ever.

I feel that a lot of the vision has to do with messaging. Influencers are flying to Mykonos while others are working two jobs and still live with their parents. Both are living out different versions of what it means to “make it.” Knowing this, how could you not want it all today?

And that’s exactly why we’ve started building a new path entirely.

The New Path to Success: Wealth & Influence

Many of us truly believe a 9-to-5 paycheck just won’t cut it.

Saving (alone) just isn’t enough.

The new American Dream isn’t about owning a house with a white picket fence. We can’t afford the fence.

Homeownership—a cornerstone of middle-class affluence and a catalyst for building wealth in this country—is out of reach for many of us. And it’s not just about the flex of having a house; the lack of opportunity here has major implications down the road. As Steven Bartlett of The Diary of a CEO put it:

“Your house is an asset you can pass down, borrow against, or sell—but you don’t get those opportunities if you’re priced out.”

So what do we do?

We have to take risks.

Because if we don’t, we’re left behind in a system that wasn’t built for us.

Some of those risks look like starting a social media page to share your voice/talents with the world. Others throw money into meme stocks or crypto, chasing the kind of upside most stable jobs rarely offer. Think back to the 2021 GameStop, Robinhood saga. Some of us are scrapping college, opting out of marriage entirely, jobs, or even the country itself.

As MoneyWise puts it, “the new American dream is to leave.”

A growing number of Americans are choosing to start over abroad—seeking out quiet European towns or beachside villages in Asia where health care isn’t a luxury and food doesn’t feel like poison. My brother made that leap. Only returning to the States in short stints. And honestly, I get it.

But no matter where we are, the new marker of success is the same: attention and influence.

Platforms like YouTube, TikTok, Instagram, and Twitch give everyday people a shot at financial independence. Social media is a wide-open lottery ticket.

If the “Hawk Tuah” girl can do it, so can I… right?

A side hustle can become your main gig. And if you play it right, it becomes a full-blown business.

This shift isn’t just touching entrepreneurs—it’s reshaping politics.

Politicians today aren’t just public servants. They’re influencers. Campaigns are brands. Visibility and engagement matter just as much as policy. Like creators, they harness social media, ride viral moments, and monetize attention.

Ed Elson said it best:

“America has fallen out of love with brands and in love with people. People are the new brands.”

And that’s what this new American Dream is about—building a brand, earning influence, and monetizing both.

There’s one caveat I will add, though. My generation tends to have a flair for the dramatics. Despite all these statistics not being in our favor, only time will tell how this all plays out. The wealth in the hands of the older generations will have to be passed down at some point. Today’s 20-somethings will be the next legislators and employers.

Only time will tell whether the decisions we make today are the right ones or not, or whether they even mattered or not.

Choose Your Own Adventure

The dream used to be simple: get married, pop out a few kids, buy a house, work hard for 40 years, and retire comfortably.

But that doesn’t have to be your dream.

You can choose your own adventure.

Want to be a digital nomad? Try it. Don’t be afraid to leave a job (ok… be a little afraid. Have a plan) that doesn’t serve you—emotionally, financially, or spiritually.

The traditional route isn’t the only—or even the best—path to success. The rise of the creator economy proves that you can carve your own lane with relatively low barriers to entry.

And beyond that, more of us simply want autonomy. If we’re going to be glued to a screen until we’re 90, we should at least get to choose what we’re building, who we’re working with, and how we’re spending our energy.

The new American Dream is about doing work that feels good and does good. Building a life we don’t feel the need to escape from.

My American Dream looks like escaping the paycheck-to-paycheck cycle, being a master of my own time, and building a life where I’m not just getting high to get by. A house with a backyard that I can mow on the weekends and toss a ball with my dog(s). Or toss the football or play basketball with my kids. Enough space to store a grill and pull it out in the summer to cook a good steak and char some corn on the cob. Sitting at the dinner table with my kids, helping them with homework that actually stimulates their little brains.

These are my dreams. Your dream may be different.

It’s on you to go get it.

Despite my profession, some people are shocked to learn that I’m not always a shining example of what to do when it comes to spending money. “Come on Mr. Finance. Aren’t you supposed to be the ‘money guy’?”

Don’t get me wrong, I enjoy saving just as much as the next guy. But who doesn’t like nice stuff? Now, five-figure watches don’t conjure up anything for me. I’ll take three hot, crispy, messy Birria tacos with a side of consommé over a dollop of caviar at a 5-star restaurant. But all that goes out the door when it comes to shoes.

Let me explain.

When I was younger, we didn’t have much money. Hell, most days, we didn’t have any money. My grandmother was 72. Long retired by now, living off social security, disability checks, and money from Connecticut’s DCF program. All while responsible for raising two growing boys. One who, go figure, had a liking for the finer things in life.

One of my first memories of money was when I learned how much money she made a month. ~$900. Almost a $1,000! I couldn’t believe it. We were rich! I was damn near salivating, thinking about everything I could do with all that money in one place. That was until I discovered a more important fact of life. The things I never thought twice about weren’t free.

I later found out our rent alone was $750/m.

So much for being part of the 1%.

There were a lot of emotions that stemmed from that pivotal moment. Guilt for always asking to go to McDonald’s every time we drove past one. Shame for feeling so greedy, knowing Grandma was doing the best she could.

My brother and I were long accustomed to hand-me-downs. But every year before school started, my cousin (I guess he took pity on us) would take my brother and me to the mall to get new shoes.

Looking back at all this taught me a couple of things. First, I need to take care of my things—especially my shoes—and if I want something, I have to get it myself.

I firmly believe that if you want to get better at saving money, you have something you can unapologetically spend money on that makes you happy, then focus all your efforts on your current and future well-being.

Do You Want To Make Your Life Easier?

Know where you need to be. Know what you’re going to wear. Know what you’re going to do and have an idea of what you’re going to say.

Do yourself a favor, make decisions ahead of time, and then get out of your own way.

But if it were that simple, wouldn’t everyone do it?

The truth is, our habits often hold us back. We are habit-forming machines. You know the old phrase, creatures of habit. What did you do as soon as you woke up today? What did you do before you went to bed last night? How did you decide what to wear today?

Chances are, based on your answer, I could have a pretty good guess at what you’ll do in these same scenarios in two weeks.

As Charles Duhigg put it, “The brain is constantly looking for ways to save energy.” This drive for efficiency is why we lean so heavily on automatic routines—they’re easy, familiar, and take less mental effort.

While habits can be helpful, they can also become our biggest hurdles.

Duhigg writes, “The brain’s dependence on automatic routines can be dangerous. Habits are often as much a curse as a benefit.” As much as habits help retirees save during their working years, the same routines can make it painfully difficult for them to spend money later in life.

On the flip side, It’s hard to get into the habit of saving money if you have to do mental gymnastics at every decision point.

As it relates to finances, I call these habits systems because they should be less physical actions—moving money here to there—and more of a structured set of processes designed to achieve a specific goal.

By building systems that prioritize saving and investing, you’ll free up mental energy, eliminate financial stress, and create a lifestyle that works for you.

At its core, we are simply a reflection of our habits and systems.

The Problem Isn’t You. It’s Your System

Most people struggle with saving more money. That’s not earth-shattering news.

However, as Desiderius Erasmus once said: “A nail is driven out by another nail. A habit is overcome by another habit.”

Start by tackling the low-hanging fruit: non-housing debt. According to the 2024 Annual Retirement Study from Allianz Life Insurance Company, non-housing debt is limiting retirement savings for 56% of Millennials, 50% of Gen Xers, and 35% of Boomers.

Once those liabilities are moderated or even reconciled, you need to replace unproductive financial systems with better ones. And luckily, in this interconnected, digital world, you don’t even have to do the heavy lifting.

For me, the game changer was automation.

Here’s how I approach it on payday:

• 401(k) (auto-deducted from paycheck)

• Automate savings to a basic savings account (one month’s rent)

• Anything above that goes to a High-Yield Savings Account (HYSA)

• Contribute to my Roth IRA

• “Travel and Vacation” account

What works for you could be totally different. But the goal should be to let the machines do the work.

By automating my savings and investments every time I get paid, I’ve been able to save more consistently and focus my energy on the things that matter most.

My colleague, Nick Maggiulli talks about this in his post about perceived pain.

“Instead of increasing your audience’s current pain you can lower their perceived pain. The Automatic Millionaire by David Bach is one example of this. Bach’s idea to automate your finances through automated transfers is one way to lower your perceived pain when it comes to saving money. Since you don’t notice the money automatically coming out of your paycheck, this method makes it much easier to accumulate wealth.”

That’s why I use Liftoff. Liftoff takes the guesswork out of investing. Let us handle the boring but necessary tasks so you can focus on what’s important.

Investing gets tricky because we tend to overcomplicate it. The more you try to tinker with your investments, the worse you’ll likely perform. The trick is to find the right allocation for you and determine how long you plan to invest. Invest according to that plan, and resist the urge to meddle.

Anything beyond that is speculation, which isn’t inherently bad—but it’s not investing, and you should size it appropriately.

The bottom line: Automate your saving and investing, then spend the rest however you please.

My perspective on money is constantly evolving.

Now that I’m an adult with higher priorities—bills, responsibilities, and long-term goals—I don’t buy shoes often. But if I happen to spot a pair of Jordans—specifically 1-14s—that I don’t already have, or a retro colorway that I like, and I have the discretionary funds, you better believe I’m buying them. It simply reminds me of all the times I couldn’t do that, and that brings me a certain kind of appreciation for how fortunate I am. Although I’m positive if my grandma was still here, she’d be shaking her head, saying, who the hell needs that many shoes?!

For most of you, it’s probably not shoes. Maybe it’s clothes. Maybe it’s wine. Maybe it’s traveling. Whatever it is, there’s probably something you’re passionate about, something that brings you joy and makes the effort of saving worthwhile.

I recognize that my view on this is a simplified and perhaps selfish one—especially compared to someone with kids. But regardless of your circumstances, the key to changing your habits (and your life) lies in understanding how habits work: cue, routine, reward.

Charles Duhigg puts it best: “The brain is constantly looking for ways to save energy.” Once you understand your cue—the trigger for your habit—you can rewrite the routine and build a reward system that motivates you.

It’s about making decisions ahead of time and getting out of your own way.

By designing better systems, you can simplify your life and free up energy for what truly matters. For me, that means having room to enjoy what I love without guilt.

Whether it’s saving for the future, splurging on something meaningful, or finding a balance between the two, we are a reflection of the habits and systems we fall back on.

Instead of entrenching myself in more political rhetoric to get myself all worked up—I know reality will likely not be as bad as we expect it to be—I distracted myself with something slightly off-topic but equally productive. I picked up a new book.

A book about The Most Interesting Man in the World.

Yeah, this guy:

In his memoir Stay Interesting, Jonathan Goldsmith, who once said that true luxury is a life well lived, reminds us that a life that we hope to someday define as a success will rarely follow a straight line.

Looking back on his life—running away from boarding school, getting fired as a busboy for pretending to be a guest, saving a noob hiker from freezing to death on Mount Whitney, losing every acting job he’s ever had before landing the one that meant everything, the role of The Most Interesting Man in the World—he recounts, “My finest moments had not cost a dine, financed instead by a mix of courage, boldness, and stupidity.”

Here’s what the most interesting man in the world taught me.

When you’re first starting out in your career, it’s equally exhilarating as it is exhausting.

On one hand, you’re young and have so many possibilities.

On the other hand, the anxiety you have for the future… I wouldn’t wish this on anyone. You have so many ideas of what you should do and who you should be by a certain age. How you’ll have it alllll figured out by 30. Lol.

This is all to say, this is the perfect time to take some risks professionally.

Try a new role in your company. If you’ve got the right moxie for it, try starting your own business. As Goldsmith said in his book, “The best time to go for broke is when you’re already broke.”

I’ve seen a number of my friends and peers take the ultimate leap of faith, venturing into real estate, working to become an author, buying vending machines to fuel a gambling addiction (more on this another day), all the way to starting a VC fund.

Considering the 2022 economic environment, it was difficult to get hired by a venture capital fund, so my friend Laurent Span was crazy enough to start his own.

Laurent said, “I chose to walk away from all of that—not once, but three times—to chase the path of entrepreneurship.”

And in just a few short years, that leap of faith and unwavering dedication to helping entrepreneurs who look like us has morphed from a growing VC fund to a successful media business, and more importantly, a way to connect with peers and founders willing to trade stories and secrets to help propel you to the next phase of where you want to be.

“Introductions to people who can help you are critical, but knowing how to handle them properly can change your life.” – Goldsmith.

He said to me, to keep yourself sane from leaving the comfort of job safety and income stability you have to have an element of optimistic delusion.

If you fail (which, in some aspects, you inevitably will), you have so much time to bounce back or pivot to something more stable. The older we become and the more responsibilities we begin to accumulate, the less we can afford to leave that stable position in the first place.

“And if you’re in your mid-20s, like I am, I believe it’s one of the least risky times to take the plunge. You have time on your side, fewer family or financial obligations, and the flexibility to bounce back if things don’t go as planned. It’s a time when you can afford to experiment, fail, and try again—less tethered to the constraints that might come later in life,” Laurent tells us.

I know it’s so much easier said than done, but don’t overthink what will happen next.

So many people are afraid of failure or the optics of failing. But the truth is, no one will care or remember your shortcomings as much as you will. The average person is thinking about themselves. I’m thinking about myself thinking about myself just writing this post.

Having a lot of money when you’re young sounds like the dream, right? We crave financial security because when money is low, things get scrappy but can also cause anxiety to compound on itself.

Don’t get me wrong, saving for retirement or financial freedom is important.

However, if you never take career risks and opportunities because you’ve already mapped out how much you’ll need to earn to fit into some preconceived idea of reaching your number, it will only lead you down a one-way road with no outlet.

Burning out, realizing you’re stuck in a place doing something you no longer enjoy, or watching as outsiders get promoted above you because they had experiences in other areas you didn’t. To me, that’s not a way to live and a surefire way to make you quit anyway.

Sam Ro, a great example of this, shares his experience of how his Substack TKer came to exist.

Sam ended the original Tweet with, “Things have not been linear.”

He was really good in his audition, apparently, but Dos Equis was thinking they might want to go younger. [Jonathan] Goldsmith was nearing 70 when he auditioned.

But his agent, upon hearing this objection, said: “How can the most interesting man in the world be young?”

As Goldsmith put it: “Her rationale made sense. To be interesting, you have to have experiences. And to have had experiences, you needed time. And I had spent a lot of time having a hell of a time.”

“Let me call you back,” they said.

He got the part.

Goldsmith writes on his success:

“If I’m being honest, I wish this all hadn’t taken so long. But, then again, maybe if success had come earlier it wouldn’t have meant as much as it does now… The harder knocks, disappointments, and travails one has, the more opportunity one has to gain awareness of who the devil we really are. I’m still trying.”

Cherish those experiences, even the “bad” ones. They taught you something. And they will make the later successes taste all the sweeter.”

If you are in your mid-career, the choice between keeping your mental sanity in check and paying the bills can weigh heavily on you.

The same principles can still apply to you: start sooner rather than later, but now it must be with purpose.

I tell clients facing a fork in the road to seriously weigh the pros and cons. This means making a list of each option’s potential benefits, drawbacks, salaries, time, and expected commitments and considering both the short-term and long-term implications.

Financially, it would be wise to have at least a year’s worth of your core living expenses set aside and a solid business plan for how you expect to make a profit.

Do your due diligence, and be sure you have a floor to stand on so that paying the bills won’t be the number one thing on your mind if the transition takes longer than expected. Having an emotionally and financially supportive spouse could help make the transition that much easier.

I can’t say definitively whether it’s a good idea, whether things will pan out for the better, or whether it will be an expensive lesson learned.

Your heart will pound, and you’ll likely have restless nights of sleep. There’s nothing I could say to calm the nerves.

What I can say is, it’s never too late to reinvent yourself.

If you feel confident that you know what you’re doing—you have a business plan, the safety cushion, and the guts to do it—hold your nose and dive in.

From there, you’ll either sink, swim, or float.

Your unique experiences, even if they don’t follow a straight path, are what make you valuable and can lead to the stories you’ll tell for a lifetime.

Stay thirsty for life my friends.

Of course you do.

What I’m about to tell you can be applied to both the 1994 animated version and the more recent live-action film.

The Disney movies I grew up with always had several subliminal messages and they always involved a tragic loss. Like Bambi or Nemo for example. On the surface (can I use that here?), Nemo is a cute story about a father trying to raise his only son in the great big ocean. But if you dive deeper (there it is), Marlon was a widower who lost everything—his wife and most of their family— and his son, who couldn’t stand his helicopter parent, risk-averse dad, was kidnapped and drug across the ocean. No wonder Marlon wasn’t funny.

You could say the Lion King was about courage, finding yourself, and all that. But at its core, this one is a story about one of the most important financial and life planning decisions any family can make: estate planning.

Yep, you read that right. Think about it, the Circle of Life.

The start of the movie is filled with talks of legacy and responsibility between an all-too-serious father and son who just wants to prove himself. Then, the sudden passing of Mufasa kicks off so many situations that I see on a daily basis in the world of estate planning.

Let me show you.

The Family Business

At the beginning of the movie, we see Mufasa as a powerful and benevolent king, ruling over the Pride Lands.

He was the heir to his own father’s kingdom which is why he so desperately wanted Simba to take this responsibility seriously. Mufasa knew that, at his rank, anything could happen, and he wanted to ensure his only son understood that this heirloom could easily be taken from their bloodlines and squandered.

Imagine the Pride Lands representing a family business.

While the kingdom represents his “estate,” encompassing everything he has grown and preserved. Mufasa knows that one day, this will all be passed down to Simba.

Estate planning 101.

Why do we do this kind of planning in the first place? It’s to ensure the continuity of what you’ve worked hard to build for is there for the next generation.

Mufasa doesn’t just let Simba run wild (pun intended); he educates him on the responsibilities of inheritance. “Everything the light touches is our kingdom,” he tells Simba, making it clear that with great wealth comes great responsibility. He is grooming his son to inherit not just land (assets) but a legacy.

This is the first key lesson: educate your heirs.

Nobody Wins When the Family Feuds

Every great story has an even better antagonist.

Personally, I can’t wait for the new Mufasa movie to drop in December so we can finally see Scar’s villain origin story.

Scar serves as a cautionary tale for so many scenarios. For one, forgetting to change your beneficiary could put what was supposed to be a thoughtful gift in the wrong hands, and it could be very difficult for the intended heir to get it back.

In the movie, Scar feels entitled to the throne and believes he should have been the rightful heir. Scar’s bitterness leads him down a dark path, plotting to take over the Pride Lands through deception and force.

However, the real-life example I will use is, Scar represents how the guardian of an orphaned child and the person who oversees any assets left to them could be two completely separate people.

In this example, Scar was likely the trustee and guardian of the minor’s estate. While, unfortunately, the streets raised Simba.

Hakuna Matata is just another term for f$ck it.

Kidding. Thankfully, Timon and Pumba, his distant relatives, were willing to take him and raise him to be the man Simba came to be. It wasn’t about the money, the family name, or even who he was–a lion amongst herbivores.

During the time they were raising Simba, Scar clearly mismanaged his nephew’s assets. The Pride Lands was a fruitful land where all creatures, from zebras and elephants to lions, could harmoniously live together. That was until Scar took over and turned it into the same baron wasteland Simba had to be saved from.

This is why it’s critical to remember that these are legally binding documents that explicitly outline who will inherit what. This is why we aim to review our client’s documents roughly every five to seven years or when life events happen.

Failing to do so could lead to senseless fighting, reopening old wounds, and costly litigation.

Right time, right age

The time Simba spent away from his homeland is another great lesson.

As a kid, I translated that period of Simba’s life as finding yourself. Like trying new things that you initially wouldn’t expect to, like once a well-fed cub going to an insect diet. Or putting your past behind you. But as many of us know, someday you realize some of your hardest times come with some of your most profound memories and truly shape you as an adult. Especially when it comes to family. Everyone has a story, and when you get to know another’s story, everything you know about their character starts to add up.

When it relates to this lesson, Simba had to essentially grow up a bit before he was privy to the family’s inheritance.

He had to go through his challenges and get a deeper appreciation for what’s his and foresight into what he could build himself.

When you have no reference for how kids will handle financial responsibility—or you do know, and let’s just say you’re not comfortable with what you see—many parents elect for age-based restrictions before they have full access to their inheritance.

It could be a cliff at age 25, then the assets become the heirs. Or a staggered approach: 33% at 30, 35, and 40 or whatever you deem makes sense. Assets will be held in a trust for their benefit until that time, certain milestones are reached, or maybe never. It could stay in trust for their lifetime, which offers several benefits like asset protection or access to government assistance for children with disabilities.

Really what this does is buy your heirs more time to have more experiences around money and develop better financial habits.

In estate planning, this is the ultimate goal: to ensure that your legacy is not only passed down but is also preserved for future generations. This could be in the form of setting up trusts for your grandchildren, establishing charitable donations, or simply ensuring that your children are equipped to manage the inheritance responsibly.

The Circle of Life

The Lion King may be a movie about kings and kingdoms, but it’s lessons on estate planning are just as relevant to anyone building a legacy.

We are the new kings.

Whether you have a sizeable or modest estate, the same principles apply: plan ahead, communicate clearly and often with everyone involved, and ensure your heirs are ready to take on the responsibility if/when the time comes.

The final scene shows Simba presenting his own cub to the kingdom—the circle of life.

Hakuna Matata? Not in estate planning.

Columbus is only a seven hour drive away, and the way flight prices and general airline issues look these days, a road trip was just what the doctor ordered. But, of course, no good deed goes unpunished. 30 minutes into the drive, I got a flat tire.

It turned what was supposed to be a seven hour drive to a total of twelve hours.

Thankfully, I was able to pop on the spare, drive to the closest tire shop, and get the open wound patched without having to fork over the money I “saved” by driving.

Nonetheless, I got there in one piece. It was a beautiful ceremony and it felt great to reconnect with our friend group that we haven’t seen since when we were all young, dumb, and single.

Love and marriage is a beautiful thing that should truly be cherished. But after the honeymoon and the first few weeks of packing/unpacking for your next chapter, the real test begins.

It’s more than just a perpetual sleepover with your best friend. It’s a legal partnership, and building a life with another person comes with the reality of sharing a life with another person and, for better or worse, all the emotions they bring. Much of the deep, dark feelings around specific topics may not come up in the early formative years of the relationship.

One of the first to come up, you guessed it: money.

Decisions around how money is earned, spent, and saved can be a lifelong struggle if the right foundation is not in place.

So, by the power vested in me, here is how I help newlyweds plan for their new life together so they can spend more decades cherishing the love that’s supposed to last a lifetime and less time butting heads over something that will come and go.

When Two Become One

I’ve written about money scripts and the different ways to view money here before. That is a great place to start your conversations about money before coming to someone like me, a financial advisor.

Once we have a base understanding of your fears and hang-ups, I start with the basics.

Where the money is and where it’s coming and going from.

The decision to combine or keep the finances separate will vary from couple to couple. However, if you do decide to combine finances – I love the idea of His and Her (His/His or Her/Her) bank accounts in conjunction with a family joint account for shared expenses.

This way, you’re not looking over each other’s shoulder for why you need yet another pair of shoes or explaining how that $10 three-way parlay wasn’t such a bad idea after all.

You’ll have plenty of other things to build together, but I will always vouche for a healthy amount of separation in this area. The joint account will serve as a place for shared expenses, like the mortgage, household bills, and emergencies.

So many people want to fast forward to investing in hopes of seeing their net worth grow, but trust me, more money isn’t the solution to healthy relationship. One of you may hold more debt than the other. Maybe you racked up some good credit card debt from the honeymoon.

Make sure your cash cushion is in a good spot before investing that money for years and/or decades.

This leads me to our next topic: planning for shared goals.

The Vision is the Mission

Once I have an understanding of how money is earned and spent, the real work begins.

Of course, we don’t know what the future will look like, but you may have an idea of what you want it to look like. Therefore, we don’t have to be precise but we do need to have something to aim at, to know where we’re going. So no matter where the money will ultimately go—your first house, anniversary trip, sending the kids to college, retiring someday—I like to start to with the end in mind and work backward.

For new couples, though, let’s start with what you’re on the same page with.

Kids Education:

Perhaps it’s to grow the family.

Beyond what it costs to simply raise a child these days, saving for their post-high school education requires extensive planning from start to finish.

First, I ask couples individually how they paid for college. Did your parents help you out, or did you pay for it yourself through scholarships or your own money?

It’s important to understand what expectations or beliefs each partner has around paying for education, as that will guide how you prioritize saving for their kids. Once we know the answer to that question, we can start to figure out the best vehicles for saving, whether it’s a 529 plan, a brokerage account, or something else.

Life In Retirement

The next step is discussing one of the most significant and challenging topics: retirement.

One of the most common issues couples face is mismatched expectations about when and how they plan to retire. Do you both want to retire early? How will you spend the first several years?

Do you envision moving to a different state or perhaps downsizing to a smaller home?

I ask couples to paint a picture of what their retirement years look like—everything from daily activities to travel plans. These discussions can be a huge eye-opener, as many couples don’t realize how different their visions may be.

Once we’ve got a clear image, we start working on a roadmap to fund that retirement lifestyle. Whether it’s contributing to IRAs, 401(k)s, or taxable accounts, the earlier we get on the same page, the better.

Life Insurance:

Retirement and education planning are big-ticket goals and a long ways away. There’s a lot of life to live inbewteen.

If you commute to work—by bus, train, or car–you’re taking a risk. If you live in a big city, you’re taking a risk. It’s great to plan for all the things we want in this life, but the unfortunate reality is, unexpected circumstances happen all the time.

Unexpected tragedies do happen. Life insurance ensures that funds are there to potentially replace all the things you’re no longer there for.

Now, life insurance typically gets a bad wrap because of the way its sold to the public, but I can’t say enough how crucial it is to a functional financial foundation.

For young couples, especially those with young children or rely on each other’s income to maintain their lifestyle, it’s a safeguard to ensure that if something happens to one partner, the surviving spouse won’t be left emotionally and financially broken.

The type and amount of coverage you need will depend on your goals, income, assets and debts, and family situation. My friend Cliff at Yield to Maturity, writes, “There are some additional variables when calculating life insurance such as final expenses or if someone would like their death benefit to be enough to cover all expenses until their children reach the age of majority in addition to funding education in full.”

Life insurance is a good place to start, but the next step is ensuring these funds are used for the intended purpose if you’re not there to see it happen.

This leads me to my favorite topic: estate planning.

Estate Planning:

I’ve written about a few different misconceptions people have about estate planning here.

Estate planning is often seen as something for the wealthy or older generations, but it’s actually one of the most critical steps for young couples—especially if you have children or significant assets or debts. Many millennials and Gen Zers are also pet owners. I’m sure you would want to make sure they go to a good home if you weren’t there.

Why do it for young couples with little money? Simple: protection and peace of mind.

Even if you don’t have a large estate, having a basic will and assigning powers of attorney ensures that your wishes are respected and your loved ones aren’t left in legal limbo if something happens.

Estate planning allows you to dictate how your assets will be distributed, who will care for your children (and/or pets), and how your healthcare decisions will be made if you’re unable to make them yourself.

Trust me. No one wants to think about these situations. But the consequences of not thinking it through are much worse. And if you start early, you can adapt your plan as your assets grow and your family situation changes (likely for a lower cost).

I can’t tell you how to handle every financial challenge you’ll face, nor which ones will be the cause of a silent car ride home. But I can help you plan for what’s next. And with the right foundation in place, you’ll be prepared to navigate life’s joys and tears—together.

I’m back with another fascinating celebrity estate plan case. And this one is a stark contrast to what we learned from Aretha Franklin, Amy Winehouse, or Whitney Houston’s estate planning woes. That’s because, reputation aside, I can certainly say that he had his estate plan well-planned.

He may have been one of the most controversial people in recent memory. But you have to admit, Orenthal James Simpson was a Grade A athlete.

If it weren’t for a few incidents that made him one of the most hated men in America, his legacy could have lived on as one of the greatest running backs in NFL history.

Before earning the alias Juice, Simpson was already showing signs of greatness in his first year at USC. By senior year, he had won the Heisman Trophy. Then, the Buffalo Bills selected him as the first overall pick of the 1969 Draft (amongst freak athletes like Mean Joe Green).

O.J. became the first NFL player to rush for more than 2,000 yards in a season, earning him the NFL Most Valuable Player (MVP) award, and became the only NFL player to do so during a 14-game regular season. He was a five-time first-team All-Pro running back and five-time Pro-Bowler. Numerous AFC Offensive Player of the Year awards, rushing yards, and rushing touchdown leader awards.

The list goes on.

In 1985, he was inducted into the NFL Hall of Fame—one of the highest honors an ex-player can achieve.

Of course, all of this was quickly overshadowed in 1994, when 95 million viewers sat in disbelief in front of a TV screen watching a two-hour police chase of a white Ford Bronco.

Which brings us to today, the impetus of this article. On April 10, 2024, OJ Simpson died of prostate cancer, resurfacing several emotions and memories evoked by this bleak day and the subsequent trials that followed.

In this article, I’ll talk about what we know about OJ Simpson’s estate and what we can learn about creditor protection from his well-thought-out estate plan.

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What We Know

As everyone is well aware, following what is likely the most famous police car chase of all time—which brought a whole new meaning to the rallying call, “the Juice is loose”—OJ went through a long trial for the mysterious, gruesome murder of his ex-wife Nicole Brown and her friend Ron Goldman, for which he was acquitted.

Watch the FX special The People Vs. O.J. Simpson if you want more of a dramatized reenactment of the events.

Although he faced plenty more legal battles, we’ll just focus on the financial troubles.

In ‘97, Juice was unanimously found guilty in a criminal lawsuit against him for the wrongful death of Nicole and Ron. “Simpson was ordered to pay $33,500,000 in damages: $8.5 million in compensatory damages to the Goldman family, and $12.5 million in punitive damages to each family,” the Los Angeles Times reported.

Today, that $33.5 million dollar judgment would be worth $66.5 million. And that’s on the low end, not including attorney wage inflation.

Not to mention the $1.44 million in back taxes the state of California claimed he owed.

Perhaps if he just made an effort to pay the resulting suit and his back taxes, that would have been that, and he could have slid into some resemblance of normalcy.

But that just wasn’t the case for OJ.

After yet another long trial for multiple felony counts, including armed robbery, kidnapping, and assault, he was sentenced to 33 years in prison for stealing his own stuff at a Vegas casino in 2009. He was released on parole almost nine years later.

And that really could have been the last time we heard from OJ to this very day if it weren’t for his love for social media.

You could say that it goes to show his work ethic never faded even after all these years. Or you could argue that he never could get past his ego.

Either way—if it weren’t for the combination of his Twitter bio reading “Hello Twitter World, It’s Yours Truly. If you don’t see it here, I didn’t say it” and his kids posting this—many of us would have never would have heard the news.

His Estate

Following his passing a few months ago, his probate estate has been filed and is open to the public.

Although it’s hard to say for sure if it was an original or was just last updated, the condensed Will posted was signed in January of this year.

A 3-4 page Will is not uncommon in estate planning. This condensed version of a Will is what’s called a pour-over Will, which typically accompanies a trust that will be the ultimate beneficiary of the residual estate. Nearly all revocable trust packages will have a pour-over Will.

All Wills must be filed with a probate court. Therefore, we can only see his pour-over Will, which essentially transferred all remaining assets in his name to his Revocable Living Trust.

His Will named Justin, Sydney, Jason, and Arnelle as his four children and nominated his longtime attorney-friend, Malcolm LaVernge, as his executor to carry out the details in his Will. LaVergne is now responsible for managing the estate. And possibly even the details of his Trust, too.

What we don’t have access to is his Revocable Trust—one of the main benefits is sidestepping those nosey people out there from being able to see and write about it—nor any subsequent trusts created from it.

The issue is he still owed a lot of money to the victim’s families even at death. And now his estate does.

The Power of Creditor Protection

So, how did he avoid paying the victims’ families for so long?

Well, most of his assets were placed in retirement plans, and he received most of his income from the NFL and other pensions. This is important because most retirement assets and pensions have some built-in creditor protection by federal law.

To a broader extent, this shines a spotlight on asset protection.

Asset protection could be crucial in an estate plan because it offers protection from creditors, lawsuits, or any judgments against your estate.

If he truly wanted to leave his kids any inheritance, he would likely leave any assets that passed to them in Trust—specifically, an irrevocable trust—to shield them from their own predators and creditors, such as divorces, bankruptcy issues, or lawsuits.

OJ’s choice to establish his trust in Nevada also highlights the significance of considering the trust’s jurisdiction.

Nevada is one of 17 Trust-friendly states that offer domestic asset protection trusts (DAPTs). These trusts are said to “offer the strongest protection you can find from creditors, lawsuits, or any judgments against your estate.”

However, these trusts do have stipulations to be aware of, and regardless, we have no idea if OJ transferred any assets to an irrevocable trust like a DAPT before his death.

Most reports say it is unclear when or how much the Goldman and Brown families will receive assets from the estate, but they will likely get something.

Judgment Day

It’s hard not to think that OJ could have been a very rich man from his days as a superstar from endorsement deals, TV appearances, or OJ merch. Gatorade would have had a field day with “The Juice is Loose.”

However, the reality is that OJ Simpson’s legacy is forever tainted.

It’s still unclear how much of Simpson’s estate will go to the families of Nicole Brown Simpson and Ron Goldman. However, the lesson to be had is that you don’t need to be famous to have creditors trying to get assets from your estate.

Simpson’s situation is a clear reminder that no matter who you are, careful planning could ensure your financial wishes are respected and your family is taken care of. This is especially important if you want to leave something behind for loved ones while keeping it safe from creditors.

“The first $100,000 is a b**ch, but you gotta do it. I don’t care what you have to do… find a way to get your hands on $100,000. After that, you can ease off the gas a little bit.”

This has nothing to do with high-yield savings accounts, Roth or no Roth, or beating the market. It’s about the decisions we make week to week, month to month, that could eventually make for a long list of financial regrets.

These are seven things that could be keeping you from reaching your financial goals.

1. Commitments That You Cannot Keep

Jack Raine put it perfectly when he wrote, “Once you grow accustomed to a high-dollar lifestyle, you can’t afford to step away. Stepping away means falling behind. You get stuck on the treadmill.”

We are all victims of lifestyle creep at one point or another in our lives. However, accumulating more financial obligations (e.g., a better apartment/bigger home, payment plans on new stuff) because your income went up will keep you from progressively saving.

2. Not Expecting the Unexpected

“Saving” money in just your checking account will surely lead to overspending. Second only to this is not having a savings account at all.

Emergency funds aren’t solely for emergencies. They’re also for expenses that you know will come but not when. Not having sufficient emergency savings could lead you to borrow or tap into your investments at unfavorable times.

However, once you have at least 3-6 months of living expenses in your savings account, don’t stop there — invest the excess!

3. Unchecked Spending

Piggybacking on number 1, you don’t need that nice of a car yet. Buying a luxury car because your income went up is a surefire way to lose money. I’m not going to stop you, though. Hell, I get the urge all the time too. But just know that whatever you do, you’re making a tradeoff.

Personally, I try not to spend too much money on things I will always enjoy doing. You can always enjoy driving a nice car. If it brings your net worth to $0 or less, it’s not your friend.

You can’t always go to your best friend’s (first?) wedding. And if you’re extremely lucky, you can’t always go to grandpa’s 90th party. If you know you’re going to drop a bag for whatever it is, know when it’s coming and budget for it.

4. Not Protecting Your Credit Score

Your credit score is an underrated tool that can have a huge compounding effect on your life, for better or worse.

Here are four areas where a good credit score is vital

• When you borrow for the big purchases, your first house, car loans, apartment shopping

• Some employers will actually check your credit history to see if you’re reliable and trustworthy

• Auto insurance rates

• If you start a business later in your career, you may need access to additional capital.

You can’t take advantage of high interest rates if you’re battling them, too.

5. Being Your Own Worst Enemy

The most important relationship you will have is your relationship with yourself. You’re the one person you truly can’t get away from.

Don’t talk yourself out of taking risks. If you are presented with an opportunity that makes you nervous, you should probably take it. And try to remember, no one thinks about you as much as you. If you try and fail, people will move on as fast as they moved on from SPACs.

If your best friend told you they were facing the same opportunity, would you give them the same advice you would give yourself?

6. Not Having a Creative/Expressive Outlet

Have hobbies outside of work and drinking.

Common said it best when he said the richest man ain’t necessarily the one with the money. The point of life is to stack up life dividends, right? Moments in your life that you can always look back and smile when you realize… damn, I did that.

Become interesting, and people will become interested in you. Then, let the chips fall where they may.

7. Not Treating Your Money Like A Business

The final and likely the most severe wealth killer is not taking your wealth-building journey seriously.

For some reason or another, we take so many other things in our lives seriously, but not our money. We say we do, but our bank statement would probably say otherwise.

If you’re serious about growing your wealth and reaching a certain number in your bank account, then you have to actually give a sh*t. Not just wish you had more money, more time, or look for a simple hack.

If you’re truly serious about this journey, then you have to start treating your money like a business. You should know when money is coming in and where it’s going. And when it’s not being spent on lifestyle wants and needs, it should be meticulously deployed in assets that improve your life today or will pay back in the future. I can’t tell you how many very wealthy people we see do this because they know they have to. Not because they want to. There’s a difference.

Don’t fault yourself for where you are now. Maybe you weren’t focused on earning more because maybe you were just trying to get your life together. Now that you are, you are completely in control of where you will be from here on out.

Sam poetically describes it as

“massive, multigenerational avalanche of cash and assets sliding down from the Silent Generation and Boomers to GenX, Millennials, and GenZ.”

This is happening behind closed doors to a myriad of sons and daughters, nieces and nephews, and even individuals outside direct bloodlines.

The truth is, many have no idea what to do or even what to think about this bittersweet plight.

There are so many feelings associated with getting an inheritance. Guilt, gratitude, responsibility, and confusion come to mind. Not to mention, your relationship with that person will certainly affect your decisions.

Losing someone you care about is truly hard. I’ve been through it enough times to know that void never truly gets filled. You just get better at finding ways to memorialize them. Despite the initial relief a financial windfall may provide, there are still underlying challenges such as inflation, debt, or stagnant income, which could mean that sudden wealth merely brings some households back to square one, at best. Regardless of dollar amounts, it’s not as simple as hitting the lottery for some families.

Dealing with inheritance can be an emotional and overwhelming experience, and each person’s approach will differ.

If you’re currently in this position or anticipate being so, I’m here to offer some guidance on how to prepare and minimize any potential feelings of regret or uncertainty

First: Don’t Do Anything

My first suggestion is not to rely on the number you anticipate receiving.

Millennials are set to inherit some $30 trillion in assets from their parents and grandparents. According to the New York Life Wealth Watch Survey, respondents expecting to receive an inheritance anticipate getting nearly three-quarters of a million dollars. However, expectations rarely match reality.

That number is much higher than the average, which the Federal Reserve reports is about $46,200

Without a Trust or direct bequest—which typically avoids probate—you must go through an arduous process of settling the estate. Therefore, you should manage your expectations around the timeframe and actual amount you anticipate. The final amount may be significantly reduced by court fees, attorney fees, and taxes. For instance, you could be subject to your state’s inheritance or estate tax, or both. As you can see, these two numbers could substantially deviate.

And if you’re in charge of overseeing this process, you’re already going through a lot. You don’t have to make any decisions immediately.

Take some time to grieve. You might be thinking about what you wish was different about their final stages of life.

You may ask yourself, do you need long-term care insurance? Should you pay off your mortgage so you don’t have to worry about it in retirement? Should you invest more so you can be financially independent sooner?

Just breathe and take your time. You can decide what you want to do when you’re good and ready.

Next: Think About How It Fits into Your Financial Picture

The next step requires some self-reflection. Consider the opportunities this inheritance will allow. How do you think about this money in relation to the assets you already have?

There are three common ways people plan to spend their inheritance. Paying down debt, supplementing retirement savings, or preserving the legacy with the intention of passing it down.

The next piece of the puzzle really depends on what kind of asset you’re expecting to receive and, ultimately, how that will fit into your financial picture today. The NYL survey notes that 58% expect their inheritance to be in cash, 43% expect it to be in property, and 28% expect it to be in investments.

Here are a few thoughts on how to handle the different asset types.

Inheriting Cash and Investments

It’s unlikely that an inheritance will solely consist of cash but rather of a combination of personal items, cash, stocks and bonds, and maybe real estate.

Cash is simple, and there will be no tax implications when parting with it.

Taxable investment accounts are great to inherit because they allow you to liquidate assets easily and give recipients a step-up in cost basis, limiting your tax exposure if you decide to sell.

Retirement accounts have their own rules, and they could get really confusing really fast. Roth IRAs may offer tax-free withdrawals, but traditional IRAs could be subject to income taxes. Regardless of the retirement plan type, there will likely be a required withdrawal window.

From here, you should determine your priorities and rank them—emergency savings and paying down debt, retirement, giving, honoring this person, whatever it may be—and based on that list, determine how to redirect these funds.

It’s worth working with your tax or financial advisor to implement the best strategy to weave these gifts into your life while supporting your goals and tax situation.

Inheriting a House

Another common situation is inheriting Mom and Dad’s house.

You essentially have three options: you could keep it and live/vacation in it, keep it and rent it out, or sell it. And if it’s split among siblings, it’s best to reach a unanimous decision to avoid conflict.

Depending on your current situation, you may not want or be able to afford to carry those costs of a second home.

Despite what TikTok says about real estate and creating generational wealth, maintaining the grounds, paying property taxes and insurance, and being a landlord is not for everyone. Don’t feel bad if that’s not for you.

Having the Conversation

To avoid family conflict and ensure success can continue to be fostered, the heads of the family must be intentional and deliberate in preparing the family.

I know of many families who feel that they don’t need to talk to their kids about these matters. I can understand keeping money and family separate or a fear of talking about death, but not when your actions can impact someone else so greatly.

Don’t be afraid to be the one to bring these discussions to your family.

If you haven’t already, lean on your advisor. They could be the bridge between generations to help everyone feel at ease and understand their responsibilities.

Assembling a competent team of trusted advisors proves invaluable every time. Beyond handling tax and legal affairs, they can offer wisdom, advice, and unwavering support as you walk through the complexities of emotions and opportunities that lie ahead of your newfound wealth.

I’ve spoken here before about how important estate planning is for every generation. Not just the senior generation.

Conversations about financial planning, wealth transfers, and inheritances shouldn’t be reserved for later stages of life. They should be part of family discussions from an early age.

Along with Bill Perkins and his book Die With Zero, many families would rather see this money put to good use while they’re still around than pass down assets to their already financially stable children.

Either way, life is full of surprises, and it’s best that everyone who should know what to do if, knows what to do if.

The decisions we make today regarding our wealth and its eventual distribution shape not only our legacy but also the financial well-being of our loved ones.

Usually, I’m not one to celebrate or make a big hoopla when it’s my birthday. Yet, comfortably settled into my mid-20s, I find myself reflecting on my journey through young adulthood.

It’s funny how and where life imparts its wisdom, and I can’t help but feel I’ve gained a thing or two along the way.

In the midst of these reflections, I’ve been engaging in conversations with soon-to-be college graduates, interns, and aspiring young advisors. It brings me back to my early days at 22, navigating the bustling streets of NYC as a newcomer. While each conversation takes a different path, the underlying sentiment remains constant — what advice would I offer to that wide-eyed, naive version of myself if I were to meet them today?

To any recent graduate entering the workforce, whatever your situation may be, my advice would be these four things:

My four secrets to success:

1. Say “yes” to as many things as possible

When you’re young new opportunities can be bountiful. You’re fresh. Oftentimes, you’re attracted to the big cities where it’s happening. New tech, and new ideas for antiquated systems are flying all around you. All it takes is the right time and right place for your own idea to spark or for someone to ask if you could help with a project they’re working on.

You never know where that one little decision could take you. And if it leads to another fork in the road, take advice number

2.You’re not too good for any task/job

When you’re first starting out, you don’t have many refined skills. You haven’t built the reputation to go all Ricky Bobby on everyone.

Inevitably, you’re going to be asked to do something that you don’t want to do.

Nonetheless, it’s something that needs to be done, and if it helps the team win, you win, too. And if you’ve followed the first piece of advice, you’ll eventually accrue enough skills and expertise that you will have enough responsibilities that you will need to ask for help, too. It’s not wise to make enemies early on.

I’ve worked at Six Flags, a bagel shop for a day, Burger King, Big Lots, Chipotle, a doggy daycare, as an insurance rep, landscaping/construction, and my professor’s financial planning shop.

I say this not to brag or give you my resume. I’m sure you don’t care about that. But where I’m going with this is that you can learn something from every job you’ve ever taken.

I’m not one to believe everything happens for a reason, but I do believe you can take something away from everything that has happened. Even if it wasn’t the most glorious work, there was some skill or trait that was required to do that job.

Remember it and take it with you everywhere you go. As long as you stay motivated. Which leads us to number three.

3. Do what you enjoy, and enjoy what you do

Most Americans spend more time in their lives working than relaxing. If you’re going to allocate that much time of your life doing something, it shouldn’t be something you loathe. You may not start within your particular dream job/field, but it should be a step in the right direction. If you’re type-A like me, then you know there should be a clear path for how you’ll get to where you’d like to be. If not, make one.

Switching gears, but this should also apply to this tenant. As Morgan Housel wrote in his book The Psychology of Money, “no one is as impressed with your stuff as you are,” no one is as impressed with your title as you are.

I could only introduce myself as Cameron Rufus, CFP, on the day I passed the exam before that got old and everyone else moved on. “Welcome to major leagues… now do something with it.” What people really want to hear is that you are passionate and care about what you’re doing.

And lastly, this sounds preachy coming from a financial advisor, but it’s not always about the paycheck.

At the end of the day, only you have to lay your head on your pillow and wrestle with your own thoughts. And only you have to decide if you’re comfortable or satisfied with those thoughts. I’ve worked with several clients to imagine what it would be like if they left their six-figure jobs to do something they really enjoy.

Nothing is more satisfying than seeing them go through with it and thrive in their new life.

4. Find a colleague or group of colleagues who you can ask “dumb” questions

Having a spotter in the gym isn’t crucial because you can’t do it. They’re there to make sure the weight doesn’t come back to crush you when you get to the apex of your set. They are the difference between attempting that last rep and stopping there because you don’t want to embarrass yourself.

You may remember many technical things from your education or self-learning, but you won’t know everything there is to know, especially out in the field.

Having someone you can go to for even the simplest questions, even if it’s just to reaffirm your thoughts, will strengthen those muscles and boost your confidence to rise to the challenge when it comes.

Asking for help can be hard at first because you don’t want to seem like the only person who didn’t get the joke. But Standford social psychologist Xuan Zhao says, “We underestimate just how willing people want to assist others and how positive they feel about doing so.” Think about it. People like feeling trusted, just as you would appreciate if someone came to you with something that couldn’t come to anyone else about (within reason, of course).

These are the four principles that I have followed so far in my career. There is plenty more good advice out there, especially for young people. This isn’t just for folks trying to break into finance; however, my colleague Blair wrote this great post specifically for young advisors trying to make it in this field.

Above all, if none of these resonates with you, I implore you to take the opposite side of these four pieces of advice.

Planting your flag and building an igloo around yourself will slowly drive you crazy as you watch everyone else around move up and out while you’re stuck in the same place you were a year(s) ago.

Refusing to do anything that you feel is beneath you will lead to a strong distaste from everyone around you and, eventually, more than likely, unemployment. I’m not saying you have to be a people pleaser and blindly agree with everything anyone says. But part of being young and employable is being willing and able to do the job.

And lastly, chasing a dollar will lead you to find it only fills a few gaps in your life that only money could solve.

These have been the secrets to the little success that I’ve had so far.

Several weeks ago, cold, exhausted, and ready to erase the day away, I strolled into my local watering hole. It’s a small, aged, dimly lit townie bar, so most of the time, I’m one of only a few patrons inside. I prefer it that way.

On the caddy-cornered TV that sat above the inventory, we watched the news in bewilderment as the war in the Middle East progressed. Not in favor of either side, I just watched with extreme discontent and sadness for the homes lost and families separated as the cameramen panned across the rubble. It’s not an ideal way to unwind, yet that’s not reality. We can’t hide from real life.

Sipping her watered-down vodka soda, me my Yuengling, the older woman next to me, and I began to talk. We must have talked for a while because, by the end of the night, it was just the two of us and the bartender.

We talked about the changes in this world she’s seen over her years. How much things are different now. She told me about her 8-going-on 28-year-old granddaughter who knows everything. The proverbial iPad kid, I presumed.

The conversation lightened and began to wind down as we talked. But out of nowhere, she flipped the script. She leaned back in her chair and said to me, “I can’t imagine how things will get better from here.”

She didn’t know what I do for work or that I would later write about this, so I probed further. I asked her, “so what now? Should we just give up all hope?”

In the midst of uncertainty, it’s easy to succumb to the weight of the world and feel as though hope is a distant memory. But as I sat in that dimly lit bar, sharing stories and thoughts with a stranger, I realized that hope is not only essential; it’s all we have.

I’ve said before that maybe it’s due to the acceptance/realization of our mortality; as we age, our view toward the future gets grimmer.

However, I once read that the secret to happiness lies in always having something to look forward to. Whether in our own lives—starting a family, moving to a bigger home, affording your dream car—or our loved ones’ lives—seeing little ones grow up and discover life for the first time, being a part of your brother’s wedding, or watching your parents retire to enjoy the life they worked so hard to see.

• Or on a bigger scale. Consider the strides in medical science, where tiny robots crafted from human cells hold the potential to repair damaged neural tissue. These “anthrobots” pave the way for personalized medicine, offering hope for those facing neurological challenges.

• And as expected, the realm of artificial intelligence continues to see groundbreaking developments. Even in my own life, I use ChatGPT and Grammarly AI to spot my errors, weaknesses, and propose better ways to say what I’m thinking.

• But that’s old news. Now, an AI model trained on a diverse range of inputs can distinguish between biological and nonbiological origins with impressive accuracy.

• Josh Brown wrote about Google’s Gemini AI technology, embracing multi-modality, marking a paradigm shift, promising a future where AI is not confined to text but seamlessly integrates text, images, audio, and video.

There is an incredible amount of discovery that’s happening right before our eyes, and despite any fears of laziness and complacency from the next generations, I can’t imagine that the progress stops here.

Things always get better—but so do our standards of living. Which may be why it’s so hard to see that things have, in fact, gotten better.

As I unravel these discoveries, it should be evident that we are on the cusp of transformative change. The trajectory of progress is undeniably upward, fueled by human ingenuity and a relentless pursuit of knowledge.

Thinking back to our conversation—of course, she said no. We can’t just give up.

Like her granddaughter, our kids, grandkids, and nieces/nephews have to grow up in this world, too.

They will have their own experiences. Good and bad. They will always have bruises and skinned knees, graduate from school, experience relationships and breakups—all the things we had to go through, too.

Maybe college, but they certainly will need to delve into the working world at some point. And they will be more equipped with tools we could never have dreamed of. But that doesn’t mean they will replace our basic need for a highly skilled workforce.

Things will always evolve and adapt. And those who don’t simply won’t survive.

Despite each evolution, there are aspects of life that will simply never change.

Morgan Housel said in the opening pages of his new book, Same As Ever:

“History is filled with surprises no one could have seen coming. But it’s also filled with so much timeless wisdom… You’d find people seeking the secret to a happy life and try to find certainty when none exists in ways that are entirely relatable.”

So, where am I going with this? The message should be clear: despite the challenges, the uncertainties, and the complexities of this world, hope is all we really have.

Our children will navigate their own journeys, equipped with unprecedented advancements of their time.

Life will evolve, but the essence of hope for a better life for the next generation will always remain.