The show has continually evolved as I learned about radio. One of the earliest adaptations I made was the idea of asking all of our guests a standard list of identical questions. I borrowed the concept from Inside the Actors Studio, who borrowed it from a show in France (though my questions were far less corny). In those 10 final questions, I wanted to ask things that would be subtly revealing of the guest, and at the same time helpful to the audience. It has worked out very nicely.
When I am on other people’s pods, they sometimes like to surprise me with my own 10 standard questions. I politely defer answering them, because a) it requires some thought/recollection, and 2) I want to keep those questions for MIB. But it comes up enough I thought I would short circuit that, using our 5-year anniversary as an opportunity to answer those questions, once and for all:
1. What was the first car you ever owned? Year, Make and Model?
A green 1968 Chrysler 300, sold to me – gifted really – for $100 by my Uncle Artie. That thing could chirp its tires in any gear. I had it less than a month when my mother borrowed (“I don’t have gas in my car”) and promptly totaled it. That was followed by a 1967 white VW bug with a 4 speed manual transmission, which was really handy when the battery died, which was often. Park on a hill, give it push, pop the clutch, and your off! My dad would not let me park that “damned Nazi-mobile” on our driveway.
2. What’s the most important thing people don’t know about your Background?
I had lots of learning disabilities as a kid I had to figure out how to deal with – severe ADHD (this was long before “ADD” became the diagnosis for any behavior problem); Dyslexia — I still cannot tell my left from right (Trick: “Left is the hand that makes the “L”); blindness to social signals (really), toss in some OCD + introversion, and you get a bit of a mess.
I (mostly) learned to manage them via “routines.” Fortunately, they fade somewhat with age. I would like to think I have even turned them into an advantage. It is a soupçon of issues that makes me delightfully oblivious to most of what is going on around me, yet at the same time allows me to see the forests when others seem to be wrapped up in the trees. In many ways, much of what I do is still me overcompensating for these issues.
3. Who were your early mentors?
A few people stand out: Jeff Weitzman, Marty Averbuch, Jan van der Baan were early mentors in school and business. Tim O’Brien tapped me when he was the Editor at the Sunday NYT, then at Bloomberg View. His insight and counsel have been invaluable.
When MIB first launched, Al Mayers would pull me aside each week and give me pointers on what makes for good radio. He patiently corrected my shortcomings and flaws. If I at all improved over 5 years of MIB, it is mostly because of him.
I am still learning from lots of folks — including MIB guests — including from my partners, Josh, Kris and Mike.
4. What are some of your favorite books?
Too many to name, but here are 3 that really influenced me: The Information: A History, A Theory, A Flood by James Gleick was very powerful (So too was his book Chaos: Making a New Science). Daniel Kahneman’s Thinking, Fast and Slow is the definitive work, but it was Thomas Gilovich’s How We Know What Isn’t So: The Fallibility of Human Reason in Everyday Life that sent me down the rabbit hole of behavioral finance in the mid 1990s. That totally altered the trajectory and direction of my career.
I also found William Goldman’s 1989 book Adventures in the Screen Trade: A Personal View of Hollywood and Screenwriting enormously influential in recognizing the role of luck, and why “Nobody knows anything.” Last, anything Michael Lewis writes is must read for me, but Moneyball: The Art of Winning an Unfair Game remains my favorite.
5. What has changed since you joined the industry? (Is this a good or bad thing?)
Two very important things: The rise of Behavioral Economics, and fee compression. Both of these have been driving the industry over the past decade, and I expect will continue to drive finance over the next decade.
6. What are you optimistic about right now? Pessimistic?
Technology has been the driving force of most of human development. Our genius for invention and innovation is why we have progressed as much as we have, and I fully expect technology will solve bigger issues like climate change, health care, and other huge challenges.
I am pessimistic about the species ability to learn from experience and to evolve socially. People believe nonsense, and while that creates an advantage in markets for those who don’t believe nonsense, its a society-wide problem with deep ramifications. Our cognitive deficiencies are highly problematic, we really are nothing more than slightly cleverer, pants-wearing primates.
7. Tell us about a time you failed — what did you learn from the experience?
When I was an attorney, I launched a mediation/arbitration firm. It was a bad business model, ultimately closing after 2 laborious years. It taught me a lot about running a business – namely, hire professionals to do all of the admin tasks (payroll, accounting, taxes, etc.). Also, it taught me about understanding scalability vs. hourly labor. Most important of all, knowing when to admit defeat and pull the plug. We often wait way too long to make difficult decisions, and we are better off ending a losing situation sooner rather than later.
8. What do you do for fun? To keep mentally and/or physically fit? What do you do to relax or for enjoyment outside the office?
Lots of stuff, I am new to the game of Tennis but fell in love with it (I am good enough now to understand how much I suck); My obsession with beautiful and classic cars is not exactly a secret around these parts. I have a few beauties I love to drive (I don’t get onto the track as much as I would like to).
Living around NYC, I regularly go to lots of live shows: Lots of concerts and plays and Stand Up Comedy: We just saw Death Cab for Cutie; Elvis Costello is later this month; Sarah Mclachlan and Mark Knopfler next month. I always see a few of Steely Dan’s shows during their annual residency at the Beacon. Jim Gaffigan, Aziz Ansari, and Jim Jeffries were a few recent comedy shows.
9. What advice would you give to a millennial or someone just beginning their career?
Don’t worry about your first job, it’s a stepping stone. The most important thing is to develop and keep building a skill set that will serve you in any job. Keep improving and learning as you go, become autodidact. Make yourself invaluable to your employer.
10. What do you know today about investing you wish you knew 30 years ago ?
I wish I understood “you are your AUM” when I started in finance. I did not become serious about accepting capital until about 7 years ago. Makes me feel like I am 20 years behind — and that motivates me. Maybe if I was less naïve about compounding 3 decades ago, I would have recognized this… For more on this question, see “Wisdom I Wish I Knew 30 Years Ago.”
Those are my painfully honest answers to the questions I ask everyone else . . .