You know him from The Daily Show and from his acclaimed stand-up specials, where he proves that smart comedy can still hit hard.

A native of Birmingham, AL, Roy has that rare ability to make you laugh while also making you think—whether he’s talking about race, class, media, relationships, or the strange little hypocrisies we all live with.

In addition to The Daily Show, Roy has performed on The Tonight Show, The Late Show with David Letterman, BET’s Comic View, Conan, and many other top TV programs. He is now the host of the CNN current events-comedy show, Have I Got News for You.

His 2025 memoir, The Man of Many Fathers explores—among other things—Roy’s complicated relationship with his father, Roy Wood, Sr., a civil rights journalist and African American radio pioneer.

Today, Roy and I talk about money, family, fatherhood, and we go deep on the craft of comedy.

Speaking of comedy, see my upcoming shows below. Save the date / buy your tickets!

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COMEDY NEAR YOU - GET YOUR TICKETS!

• May 16: QED, Astoria Queens, 9:30

• May 20: Dunwoody Country Club (members only)

• May 21: Atlanta Punchline - ON SALE

• May 22-23: DC Comedy Loft ON SALE

• June 4: Atlanta Athletic Club (members only)

• June 19-20: Comedy Catch, Chattanooga ON SALE

• June 25: Couples Therapy Comedy at West Side Comedy Club, NYC

• July 21: The Venice West, Los Angeles - On Sale soon

• July 23: Cobbs Comedy Club, San Francisco - ON SALE

• Aug 1: Sticks and Stones Comedy Club, Southampton, NY -

• Aug 8: Atlanta Country Club (members only)

• Aug 13-16: Headlining McCurdy’s in Sarasota, FL - ON SALE

• October 15: Capital City Country Club (members only)

“Nobody gets ahead anymore,” says the mainstream press.

And 60% of young people believe that the American Dream is dead!

But my guest today calls this hogwash, baloney, and complete malarkey. is a historian, entrepreneur, investor, and the author of a new book called How to Get Rich In American History: 300 Years of Financial Advice that Worked (And didn’t) in which he explores how ambition, risk, and reinvention have shaped America from the very beginning.

He also reveals the money myths, sacred cows, side hustles, and NAYsayers that have always been a part of our society.

What if so-called timeless beliefs about money like “invest for the long run,” “compound interest builds wealth,” and “real estate always goes up” weren’t always true…and play out less often than you think they do?

Joseph’s book is part history, part playbook, and part reality check. He brings lessons to life with rigor that is deeper than an oil well and a wit that is dryer than the Texas plains. And in so doing he demystifies the past in order to clarify the present for anyone thinking about money, success, and what it really means to “make it” in America.

Follow Joseph here.

They were recent Kellogg MBA grads who worked for a very large online retailer. (I won’t say which one, but it’s as big as a South American river.)

Friendly and respectfully curious, they asked us about our career paths. They were duly impressed with my accomplished classmates—a hedge fund manager and former start-up executive who has rung the bell a few times. I’ve done all right myself.

Then one of the guys asked an excellent question: “Where were you at 30?”

I laughed, pointed to the software leader, and said, “When I was 30, I was deep in debt, sharing a two-bedroom, one-bathroom walk-up with this guy, and working in an industry that was unravelling violently.”

The young men smiled at my unimpressive answer. I elaborated.

On my 31st birthday in March 2000, the stock market was in free fall. The Nasdaq Composite index lost 1/3 of its value in four weeks, on its way to shedding 80% over 18 months.

LAUNCH.com, the digital music company where I worked was vaporizing alongside the rest of the Internet 1.0 economy. Three rounds of layoffs eliminated four out of five of my colleagues, and I barely survived the cuts.

I had sold exactly none of my stock because, foolishly, I believed holding onto it was a sign of loyalty. And when Yahoo! finally bought us for loose change that Jerry Yang found in his couch cushions, my payout bought me a desktop PC running Windows Millennium Edition.

Around this time, I confessed my financial situation to a new girlfriend—a dotcom multimillionaire who was smart enough to cash out. Despite my full head of hair and low-carb-lean body, she was not impressed.

The new grads laughed at my pain. When I divulged that liquidating my equity would have paid off my $80,000 in loans—$150,000 in today’s dollars, they traded fist-bumps hearing a balance similar to their own.

Then my hedge fund buddy shared his story. Right out of business school, he had taken the strategic consulting route. The lucrative pay package funded a nice apartment and the ability to chip away at his tuition debt.

But he found the work unsatisfying and decided he wanted to be an equities trader, a position for which he was positioned poorly. So, he quit the consulting gig and gave up his flat. He lived like a monk for almost two years while taking trading courses and networking with a seemingly irrational persistence, until he finally cracked the industry.

The bold bet on himself worked. Today, he’s reaping meaningful rewards in the form of both career satisfaction and financial compensation.

My other friend at 30 years-old was on a more consistent progression up the success ladder, propelled by a brilliant financial mind and a .1% work ethic that has barely diminished almost three decades later.

One of the benefits of having an ally like him is his ability to see the bigger picture. On a drive to the airport back from an early 2002 ski trip—as single, childless dudes, we could still find a few bucks for the important things—I was lamenting my situation. He put it into perspective.

“Okay, this girl’s not into you. Whatever,” he said. “You’ve got a good job at Yahoo! and stock options that could be a game-changer. Just keep your head down and keep moving forward.”

That’s what I did, and that’s exactly what happened.

Three years later, I was a millionaire.

How am I doing?

I took the young Amazonian’s question as a rhetorical check in—was he doing okay? Up to this point in life, he has done all the right things. Yet, despite having an impressive degree and a great job, he feels as if he’s not where he should be.

This is natural. Young people think careers are linear. Older folks know they can be jagged and often chaotic. And that’s okay.

In her forthcoming book You Can Just Do Things, author —a former drug addict, poker champion, and tech CEO—discusses the importance of embracing the “Moat of Low Status.”

Hall argues that many people spend part of their twenties and thirties in a bit of a ditch—an uncomfortable stretch where your peers seem to be pulling ahead while your own life feels uncertain, underfunded, and unimpressive.

But the moat has advantages. It shrinks your ego. It forces you to adapt. And you persevere because you have no choice.

Over time, however, good things happen. Opportunities arise that were not visible from the other side of the moat, and the path makes itself known. It happened to me, to Mister Hedge Fund, and it happened to Cate.

I’ll bet you a desktop PC that it will happen to these two young guys as well.

On their way out the door, my new friends swung by our table to say goodbye. I did my best to return their Gen Y daps, and gave them the best advice I could.

“Keep your heads down, boys. And keep moving forward.”

THE END

(hey — please share your thoughts in the Comments section ↓↓↓↓)

My guest today is Dr. Paul Hokemeyer, a psychotherapist who works almost exclusively with ultra-high-net-worth individuals—the kind of people most of us assume have life completely figured out.

Spoiler alert: they don’t.

Dr. Hokemeyer is the author of Fragile Power, a fascinating look at the emotional and psychological challenges that come with extreme wealth, fame, status, and success. In his work, he’s seen firsthand how money can insulate people from consequences, distort relationships, and quietly fuel addiction, anxiety, and isolation.

In other words, he has a front-row seat to the uncomfortable truth behind the fantasy.

Today, we talk about why power is more fragile than it looks, how wealth can complicate identity and purpose, and what it actually takes—whether you’re worth $10,000 or $10 billion—to build a life that feels meaningful.

For 250 years, profanity has been conspicuously absent from official White House communications. Sure, there were a few hot mic moments where George W. Bush said “shit” or called a reporter an asshole. Biden told a different reporter he was a son-of-a-bitch, and Nixon’s home recordings were full of coarse grumbling and anti-gay slurs.

At its worst, however, anything a President offered for public consumption never exceeded PG-13 material.

But leave it to Donald J. Trump to buck a ¼ millennial trend of expletive-free diplomacy. Last week, on Truth Social, he blasted the Iranian regime with this subtle gem: “Open the Fuckin’ Strait, you crazy bastards.”

While this might be a reasonable thing for a President to think, it is—for lots of good reasons— something that 44 other POTI would have left unsaid. As much as it scares me, I must confess that I find it fascinating to read a President’s unedited thoughts. Trump’s rant made me imagine how awesome it could have been if others had been equally self-indulgent.

Think of how the Declaration of Independence might read if Thomas Jefferson listed among our unalienable rights “life, liberty and the pursuit of mother-fucking happiness” and then called King George an “English prick!”

This wouldn’t have been diplomatic, but it would have felt so good!

Maybe JFK’s inaugural address would resonate better with Gen Z if he had implored, “Ask not, what the country can do for you. Ask what your lazy ass can do for the goddamn country.”

And surely there was some impulse inside of Abraham Lincoln to use his address at Gettysburg to call the Confederates “a lousy bunch of cross-eyed, cousin-rapers.”

Ronald Reagan chose his words carefully, but if the Great Communicator lacked an internal filter, he might have cautioned Mikhail Gorbachev to “Tear down this fucking wall, you forehead-birthmark-having little bitch.”

“Mr. Gorbachev, tear down this fucking wall, you forehead-birthmark-having little bitch.”

–Ronald Reagan

And you know that the words Bill Clinton was actually thinking were “I did not have sexual relations with that lying ho-bag, Ms. Lewinsky.” (His thoughts, not mine —I’m on your side, Monica!)

I think the biggest missed opportunity—one might even say it was egregiously neglectful—was President Obama’s refusal to drop the N-word during one of his States of the Union. If there was any President who had the cultural green light, it was him.

But since we’ve still got three years of Trump, and we’ve already heard him say “pussy,” “shithole,” and “fuck,” I wouldn’t put the N-word past him.

Surely there’s a bet to be made on Polymarket.

🇺🇸 BONUS MATERIAL 🥳

I had already written the draft about profanity above when, earlier this week, the President broke the internet, the news cycle, and every Christian’s heart when he posted this AI image of himself as a doctor Jesus:

I used this opportunity to goof around on Midjourney and produce what I think are some pretty outstanding images of Trump in the mode of god / God / religious symbol.

Here he is as Greek god Zeus, the king of Mt. Olympus:

And of course, the Buddha…

While the Laughing fella is adorable, the realistic one makes me think how great it would be if Trump started meditating. Maybe the people who make the Calm app should offer him some equity.

The Indian gods are fun because they have multiple appendages and animal attributes and stuff. I thought the two of him as Ganesh were particularly wonderful.

And these, as a modern Prometheus (left) and the Aztec god Quetzalcoatl (right) are super fun.

But my favorite of all is this one of DJT as the Egyptian god, Osiris.

Have a great day!

That was the question Michael Cruz Kayne’s wife asked him after the death of their one-month-old son, Fisher.

Michael is a comedian, actor and a staff-writer on The Late Show with Stephen Colbert, where his work has earned a Peabody Award, a WGA Award, and two Emmy nominations. He made his off-Broadway debut in Sorry For Your Loss, a raw, comedic, and deeply vulnerable one-man show about coping with a parent’s worst fear, the loss of a child.

This is a sad but inspiring conversation. I found Michael’s attempt to make sense out of his grief and to honor Fisher’s brief life to be an uplifting act of service.

You can watch the special today on the Dropout network.

After a month of procrastination, I finally watched Inside the Manosphere, Netflix’s documentary on the rise of ultra-male influencers whose homophobic, misogynistic, and anti-Semitic content is attracting millions of young male followers.

I wasn’t familiar with any of these creators going in. Unfortunately, I now know about dudes like Sneako, Myron Gaines, and Justin Waller, who drives a Lamborghini, wears bespoke suits, and brags about cheating on the mother of his children, all while presenting himself as an enviable model of modern masculinity.

Midway through the film, I got a group text from my sister, reminding my siblings and me that today would have been our late father’s 99^th birthday. Thinking about him while watching these cringey creators made the contrast impossible to ignore. My dad wasn’t macho, but he was all man. The residents of the “Manosphere,” on the other hand, are sniveling little boys.

In his 2025 book, Notes on Being a Man, argues that men have three core duties: to protect, to provide, and to procreate. These are not exclusively male roles, but they are essential if a man wants to be a dependable partner and father.

By comparison, these influencers mostly preen, pose, and pretend. It’s all style and no substance—a child’s fantasy of alpha masculinity, optimized for clicks and monetized through crypto, gambling, and porn. Sadly, it’s working.

My father was the opposite. He was a provider who worked 40 years at a job he probably didn’t love to pay for Catholic school tuition, football cleats, groceries, and the mortgage. He spent very little on himself, and the idea of signaling status through cars, clothes, or watches would have struck him as absurd.

He was a protector—not physically imposing, but reliably present. Married 55 years, he remained by my mother’s side through thick, thin, and her terminal illness.

And yes, he procreated, siring six kids, but more importantly, raising them. Dad paid the bills, did the yard work, washed a few dishes, and showed up at youth sports games, plays, and graduations. Along with my gifted mother, he made sure we did chores and did not talk back, but also engaged us in conversation almost every night at the dinner table.

He never asked for credit, and he never complained. In so doing, he raised good sons and showed his daughters what they should expect in a husband.

Unfortunately, reliability and fidelity don’t trend on Snapchat. You’re never going to see an influencer bragging, “Let’s hear it for 13,000 days of not abandoning my family! Smash that LIKE button, y’all!”

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But algorithms love the braggadocious douchebaggery we see in Inside the Manosphere. To his credit, Host Louis Theroux plays the perfect straight man.

At one point, Justin Waller explains the “one-sided monogamy” in his relationship—his partner remains faithful; he does not. “The woman I’m with,” he says, “doesn’t talk to other men.”

Theroux just looks at him. Justin, assuming the reporter is jealous, fills the silence with, “It stings, huh?”

Theroux reacts with the perfect, incredulous laugh. As if Waller’s situation was anything to admire.

I would have liked the film to delve deeper into the societal “whys” behind the rise of performative masculinity. But Theroux makes one important, if predictable, observation: most of these influencers grew up in homes without strong male role models. Their dads were either absent or barely present.

You can see the damage. The guys are wounded, and—as bullies do—mask their insecurity by tearing down others, especially women, gays, and Jews.

I cannot imagine my father belittling the mother of his children or anyone else. Respecting other people’s dignity—regardless of their religion, ethnicity, or sexual orientation—was fundamental to maintaining his own.

Ultimately, Inside the Manosphere is less shocking than it is depressing. Social media has given bad ideas a platform and a business model. And the popularity of these broken boys will provide anecdotal evidence to those eager to prove that males are fundamentally broken.

But we shouldn’t mistake pubescent charlatans for grown men who, like my father and billions more worldwide, are reliable, kind, and loyal. They’re not flashy, but maybe their stories are the ones Netflix should be telling.

Happy birthday, Dad.

COMEDY NEAR YOU - GET YOUR TICKETS!

• May 3: Charlotte - Duckworth’s - ON SALE

• May 7: Private School Comedy, West Side Comedy Club, NYC

• May 20: Dunwoody Country Club (members only)

• May 21: Atlanta Punchline - ON SALE

• May 22-23: DC Comedy Loft (tickets available soon)

• June 4: Atlanta Athletic Club (members only)

• June 19-20: Comedy Catch, Chattanooga ON SALE

• June 25: Couples Therapy Comedy at West Side Comedy Club, NYC (tickets available soon)

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1. It provides a service to those looking for their next great book, and

2. I lack imagination.

But you, lucky reader, get to find out about one of my favorite books of the past several years right now because The Doorman is not just an exhilarating read, but its author is my guest on this week’s podcast.

The Doorman is a thriller set in a semi-fictitious Upper West Side apartment building called The Bohemia. It’s really The Dakota—where John Lennon was shot in 1980— and where Pavone lives with his family today.

The building provides an aquarium-like lens through which to observe the creatures swimming in its tony waters—a microcosm of New York City and how it has changed. Fifty years ago, The Bohemia housed mostly artists, celebrated academics, and diplomats. Today, Pavone writes, “as with everything else in New York, the cultural class (has been) replaced with financiers.”

The intra-1% tension is one of many insightful threads woven into a pitch-perfect dissection of money, race, status, and politics in modern New York City. The comparisons to Tom Wolfe’s Bonfire of the Vanities are inevitable and intentional.

In the podcast that you are going to listen to and love, Pavone told me he set out to write a modern version of Bonfire, a New York crime novel that is “about racism, but also about class…which is often what we’re talking about when we talk about race.”

He brings it to life through his characters. There’s Chicky Diaz, the eponymous doorman who carries crushing medical debt while serving the building’s elite. Among them are the ethereal Emily Longworth and her husband, Whit, a sketchy billionaire with more money than taste.

But the most interesting conflict isn’t between rich and poor, it’s within the rich. Julian Sonnenberg, the Longworth’s art dealer, has cultural capital but fading finances. While he and Whit are neighbors, they definitely are not equals. And each of them is acutely aware of this.

Julian sums it up, “The corrosive thing about New York is that there’s always someone with more — more money, more fame, more power, more respect.”

Nobody needs to feel sorry for Julian, who is part of what Pavone calls the “normal rich,” like lawyers who take nice vacations and belong to a country club or two. They don’t worry about having cash for a taxi, but in NYC they do worry. About the billionaires above them. About being fired for saying something insensitive at work. About the $70,000 tuition at private schools, where teachers wear “Tax the Rich” t-shirts on parents’ day. About where their kids will go to college. Sure, Chicky’s girls got into Ivy League schools, but will Julian’s white children be given the same consideration?

Pavone asks many questions, but answers few. For all his diagnosing the ills of virtue-signaling, inequality, and racism, his politics remain opaque, much to the reader’s benefit. If we were to ascribe motives to the author, we would stop observing the characters and start judging them.

Instead, he just presents us with the aquarium and lets us watch the fish, to notice which ones are circling. And which ones are getting eaten.

THE END (but see comedy dates below ↓↓↓)

New Comedy Dates: Added San Francisco and L.A.!

• May 3: Charlotte - Duckworth’s - ON SALE

• May 7: Private School Comedy, West Side Comedy Club, NYC

• May 20: Dunwoody Country Club (members and guests only)

• May 21: Atlanta Punchline - ON SALE

• May 22-23: DC Comedy Loft (tickets available soon)

• June 4: Atlanta Athletic Club (members and guests only)

• June 19-20: Comedy Catch, Chattanooga ON SALE

• June 25: Couples Therapy Comedy at West Side Comedy Club, NYC

• July 21: The Venice West, Los Angeles

• July 23: Cobbs Comedy Club, San Francisco ON SALE

• August 8: Atlanta Country Club (members and guests only)

I originally wanted to talk to Steve because of his experience leading the go-to-market plan of The Beatles Anthology, one of the most commercially successful recording projects of all-time. It was to be the follow-up episode to last week’s interview with Peter Doggett, author of You Never Give Me Your Money: The Beatles After the Break Up.

And while Steve and I discussed this at length, I found his experience as an executive vice president at Turner Broadcasting in the 1980s even more interesting. Working directly for Ted Turner, Steve’s responsibilities included everything from home video to cable syndication and World Championship Wrestling. He shares a great story about utilizing 1-900 telephone numbers to monetize wrestlers' smack talk. It’s a fun insight into the early days of a pre-Internet media “start-up.”

Steve oversaw the 50th Anniversary celebrations for both Gone With the Wind and Casablanca, then—after Turner— went on to captain the release of Frank Sinatra’s Duets, which eventually led to his work with the Fab Four.

Check it out here or wherever you get your podcast love.

Bye!

1. Cute puppy videos,

2. Soldiers returning home / surprising their kids at school,

And…

3. Celebrities who have gotten fat

(Worry not—there will be no obesity-shaming here.)

The first two categories make sense. Puppy reels flood our amygdalae with oxytocin, and military reunions show humans at our most joyful. But the third category yields a darker version of “happiness.” It’s not delight—it’s schadenfreude.

Don’t pretend you didn’t snicker when, a few years back, Axl Rose reappeared looking as if he had eaten Bret Michaels. Or that, on some level, it didn’t make you feel better about yourself when you saw photos of the now frumpy ‘90s actress who looks like she spends all day cooking soup.

These images grab our attention because we’re tribal animals, constantly checking our place in the hierarchy. Someone else’s downfall means we’re doing better—if only by 1/8 billionth —or at least that’s what our petty-ass brains tell us.

While watching one of these delicious reels recently, I caught myself and wanted to understand what was going on in my head. So, I Googled schadenfreude, the German word for pleasure at someone else’s misfortune.

In addition to the worthwhile reminder that schadenfreude is most evident in people with low self-esteem, I learned that it manifests in four distinct ways, each of which sheds light on ourselves and the algo’.

1. Justice Schadenfreude: “They had it coming.”

If there’s a “good schadenfreude,” this is it. When jet-setting billionaires and princes who abuse underage girls get exposed, it restores balance to the universe.

This is why we devour stories connected to Jeffrey Epstein or Bernie Madoff—not just for the scandal, but for the possibility that powerful people might face consequences and for reassurance that life is fair. (Spoiler alert: it’s not.)

2. Rivalry Schadenfreude: “My team > your team.”

This one is tribal, and we all do it.

It makes me chuckle when my progressive friends point out all the Republicans in the Epstein files, while conveniently forgetting the numerous mentions of left-leaning folks like Bill Clinton, Noam Chomsky, Larry Summers, and Reid Hoffman.

Similarly, when my MAGA friends—and I have a great number of them—point to the credible allegations of Nancy Pelosi’s insider trading, they ignore the fact that the Trump family treats the White House like its personal piggy bank.

Consciously or not, we are all hoping to prove our rivals to be less smart, talented, or virtuous than we are. The algorithm feeds this bias and serves us endless proof that we’re on the right side of history—or March Madness.

3. Envy Schadenfreude: “Oh thank God, they’re not perfect.”

Here’s where the chubby celebs come in. The former supermodel loses her thigh gap. Axl Rose can no longer pull off his leather pants (like, literally – they’re stuck around his thighs). It shows that these “special” people are just as vulnerable to gravity, UV rays, and trans fats as we are. And that soothes our insecurities.

4. Aversion Schadenfreude: “I just don’t like this person.”

Schadenfreude correlates with low empathy, which is why Instagram serves me videos of Britney Spears melting down and juggling knives.

When we enjoy seeing someone whom we thought never deserved their success lose their money or marbles, it might feel like karmic justice, but we’re just being a-holes. And social media has figured out that if it can identify whom you dislike or disdain, it can keep you watching forever.

So what’s your point, Paul?

Here’s the part I think I was missing before: Schadenfreude isn’t a bug in the system. It’s one of those core instincts (like fear, anger, and arousal) that the algorithm exploits. When my feed is full of perky boobs, I know I’m being manipulated. I don’t do anything about it, but I know.

Schadenfreude, on the other hand, can be harder to recognize, perhaps because the instinct is so deeply ingrained in our thinking. The uncomfortable truth here is that something that feels totally natural can be wildly counterproductive.

Relishing someone else’s weight gain doesn’t make me any healthier. Comparing my mental state to Britney’s or Gary Busey’s might pass the time, but won’t stop my own eventual cognitive decline.

So it’s probably best to focus our thoughts elsewhere. We won’t eliminate schadenfreude from our operating systems, but it’s possible to turn down the volume. When you recognize it, hit “Not Interested” and go watch some puppy videos.

At the very least, leave Britney—and for that matter, Axl—alone.

THE END (but see comedy dates below ↓↓↓

COMEDY NEAR YOU - GET YOUR TICKETS!

• May 3: Charlotte - Duckworth’s - ON SALE

• May 7: Private School Comedy, West Side Comedy Club, NYC

• May 20: Dunwoody Country Club (members only)

• May 21: Atlanta Punchline - ON SALE

• May 22-23: DC Comedy Loft (tickets available soon)

• June 4: Atlanta Athletic Club (members only)

• June 19-20: Comedy Catch, Chattanooga ON SALE

• June 25: Couples Therapy Comedy at West Side Comedy Club, NYC (tickets available soon)

I’m writing today to share that I have moved my podcast to Substack. It will still be available on Spotify, Apple Podcasts, and a dozen smaller podcast apps, but will be hosted on the Substack platform, so also available on the Substack app.

The first episode is a new interview with Peter Doggett, one of the great writers of the rock era and a man who has spent decades studying what happens when ambition, fame, and enormous piles of cash (and drugs) collide.

Peter is the author of You Never Give Me Your Money: The Beatles After the Breakup, a deeply human book about the legendary band, not only at their creative peak, but also at their breaking point. It chronicles the time when the most successful band in history discovered that unimaginable wealth and universal adoration do not, in fact, lead to contentment and enlightenment…but do lead to lawsuits, divorce, and—sometimes—heroin addiction.

Peter has written for Rolling Stone, Mojo, Q, and many others. His work has the rare quality of making you love the music even more while feeling slightly better about your own messy life. His latest book is Surf’s Up: Brian Wilson and The Beach Boys.

Btw, if you like this episode, you’ll also love the new Amazon documentary about Paul McCartney called Man on the Run. Check it out.

• Why beliefs can help us perform at our top potential (or vice versa)

• The difference between facts, faith, and belief

• How beliefs can benefit us, even if they’re not “true”

• The importance of cognitive flexibility

• And, the power of prayer, even for non-believers

Nir also shares a powerful story about the thing he learned by buying his mother birthday flowers from the “wrong” florist. Nir's work has been featured in the New York Times, Forbes, Harvard Business Review, Psychology Today, and many more. He attended The Stanford Graduate School of Business and Emory University.

• Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ ⁠HERE⁠⁠  (DO IT!)

• Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ ⁠HERE⁠ 

• Learn more about Nir on his website. 

• Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ ⁠HERE⁠⁠  (DO IT!)

• Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ ⁠HERE⁠ 

• Buy Gina's book HERE.

• Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ ⁠HERE⁠⁠  (DO IT!)   

• Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ ⁠HERE⁠ 

• Buy Matt’s book, I Told You So! here. 

Tom was a scrappy middle-class kid from suburban Atlanta who fought his way into the University of Pennsylvania’s Wharton School, a job at a prominent investment bank, and then a seat on the desk of a prestigious hedge fund.

Things went well at first, but during the 2008 meltdown, Tom was under extreme pressure to perform. So, he traded on material, non-public information, rationalizing his actions with the mantra “everybody’s doing it.” These transactions earned him about $46,000 in compensation, but also a visit from the FBI and, eventually, the lifetime badge of “felon.”

Tom’s new book Wired on Wall Street tells the story of a career arc that fits into a theme I’ve been thinking about lately. In the first half of life, success is about what we do. In the second half, it’s about what we manage not to do.

From the time we enter kindergarten until we get our careers going, success is roughly equivalent to accomplishment:

• DO get good grades

• DO strive for athletic distinction

• DO go to the right college

Obviously, there are exceptions to this “rule,” but for the most part, what’s rewarded is creating a dazzling resume, demonstrating the willingness to work hard, and showing that you can hang with other high achievers.

Once you’re on the right path, staying on top is mostly about not lighting your life on fire. Doing so—or NOT doing so, as it were—means avoiding the adult world’s myriad potential pitfalls:

• DON’T buy stocks on inside information

• DON’T do cocaine at the office

• DON’T sleep with the babysitter

The cruelest thing here is that the more you win in Phase 1, the more opportunities you’ll have to screw up Phase 2. For example, if you earn money early, you can afford to buy cocaine. Or, if you achieve fame at a relatively young age, people will give you cocaine. And women who aren’t your wife—who might just be your babysitter—will pay way more attention to you if you have money, fame, or cocaine. (Note: I have no personal experience with fame, powdered narcotics, or amorous child care providers.)

Avoiding these traps isn’t an accomplishment anyone talks about. Nobody brags on their LinkedIn profile: “25 years of NOT embezzling from my employers!” or “Made ZERO racially insensitive comments to my co-workers this quarter!”

Just see how it plays when you brag to your wife: “Honey, according to the internet, there are hundreds of women in our area who want to have sex with me, but I haven’t touched any of them!” Your virtue will not be celebrated the way you’re hoping.

No, your reward is a solid marriage, kids who still talk to you, and a relative lack of chaos in your life. Indeed, you don’t get a plaque for staying out of prison, and there are no trophies for not being on the Epstein List.

However, maybe there should be, because discipline and judgment can’t be outsourced. I can hire a physical trainer to help me work out—to do the exercises with the proper form and intensity. But I can’t hire him to NOT drink for me or to NOT eat that fourth doughnut at breakfast. We all have our weaknesses.

There but for the grace of God…

Tom is the second convicted felon I’ve interviewed. The other was Lara Love Hardin, author of The Many Lives of Mama Love, a great book that earned a spot in Oprah’s Book Club. What struck me upon meeting them is how normal they both seem. When you think “felon,” you might think “scary, unstable person.” But Tom and Lara are just regular, smart, high-achieving people who made big mistakes. Or, as Tom chooses to call it, “bad decisions.”

Like millions of Americans, Lara got addicted to opioids, and her life spiraled out of control. Similar to other earnest young people, Tom “cheated” because he wanted to be respected in a highly competitive field. The same ambition that brought him to the heights of the financial industry was what took him out of that game forever. Fortunately, both have rebounded and found their paths forward.

If you have a few minutes, check out my conversation with Tom. It’s a worthy reminder that any of us can mess up—but also that life isn’t over just because you screw the pooch. Or the babysitter.

THE END

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