Good morning guys. I’ve been on a writing hiatus these last several weeks while I caught up on several other areas of my life.
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.
(Photo taken inside the Waymo)
(Me getting inside the Waymo)
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.
Videos like this certainly don’t help:
@true.wrong Watching Waymo driverless vehicles drive sometimes feels like watching dumb and dumber drive 😂 There needs to be some sort of petition for Waymo’s to not drive on narrow two way streets because they never get it right, ends up glitching, and causes delays. I’m definitely one of the biggest Waymo hater for all the times they’ve delayed me in getting things done by trapping me in a street or a parking spot. This video was sped up 3.7x because this whole ordeal took 3 minutes. @Waymo #waymo #waymosanfrancisco #baddriver #sanfrancisco #waymocar ♬ Welp, Didn’t Expect That – Yu-Peng Chen & HOYO-MiX
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.
