Nine times out of ten, a solo octogenarian in New York is the most interesting person in the room. Phil was no exception. An inadvertent man of mystery with a drink order more reliable than a Japanese train. Miller High Life. Never more than two. Never fewer.

He’d come in most days. Sit at the bar. Nurse his drink. I watched this routine more than a dozen times before working up the nerve to interrupt and introduce myself. Bought his next beer for the princely happy hour sum of three dollars. Started talking to him about his life.

Artist from the west coast. Sixty years in the same rent-controlled apartment on 6th street. Unbelievably low rent. Works in the MOMA’s permanent collection. New York in a nutshell.

I saw him later that week. Said hello again. Received a quizzical look, void of recognition, and a polite hello back. His short-term memory was not good and I’m not that memorable. Had a similar conversation as last time. Heard many of the same stories.

This pattern repeated itself over and over for months. The retellings never got boring. Slightly varied, they added depth and color. Like continually tracing over the same line.

The bar closed. I’d still frequently spot Phil in Tompkins, sitting on a bench when the weather was nice. One of those comforting New York moments. I hadn’t seen him in months. Not a great sign, but I’ve been traveling a lot and the weather has been awful.

Phillip Van Aver died on January 24th. An important enough part of the community to be memorialized in the hyperlocal news I read obsessively. A somber piece of news to stumble across. A good man who lived a good life.

I don’t remember a lot of grammar rules, but I know I’m supposed to use “fewer” for things that are countable. There’s now one fewer Phil. One fewer artist. One fewer person who was a core part of shaping a neighborhood I love in a city I adore. There are fewer and fewer people like Phil every day. Their absence is felt. I don’t know how to count that. There’s just less.

In 2025, I read 55 books. I mostly chose these based off of recommendations (primarily from in-person conversations), and keep a running list of books that I may want to read next. The recommendations I get are (normally) good, and it’s fun to be able tie a book to how you first heard of it. Given I rely so much on other people’s picks, I thought it’d be helpful for me to share my own.

I mostly read non-fiction. These are books that were new to me in 2025, so plenty of them are years (or even decades) old. I’ve highlighted five books were lesser known to me (e.g no cultural phenomenons or TV/Movie adaptations) that I particularly liked. Beyond that, I’m going to avoid including authors, blurbs, or my own personal thoughts. That’s partially laziness, but partially because it’s fun to pick books just off titles.

My Five Picks

1. Boom Town: The Fantastical Saga of Oklahoma City

2. Baddest Man: The Making of Mike Tyson

3. No More Tears: The Dark Secrets of Johnson & Johnson

4. Blood Aces: The Wild Ride of Benny Binion

5. Paper of Wreckage: The Rogues, Renegades, Wiseguys, Wankers, and Relentless Reporters Who Redefined American Media

The Rest

1. Will You Please Be Quiet, Please?

2. The Last Manager (How Earl Weaver Tricked, Tormented, and Reinvented Baseball)

3. Flagrant Self-Destructive Gestures (A Biography of Denis Johnson)

4. The Tragedy of True Crime: Four Guilty Men and the Stories That Define Us

5. The River of Doubt: Theodore Roosevelt’s Darkest Journey

6. Jesus’ Son: Stories (Picador Modern Classics Book 3)

7. 1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation

8. Bel Canto: A Novel

9. Ladies and Gentlemen, the Bronx Is Burning: 1977, Baseball, Politics, and the Battle for the Soul of a City

10. Searches: Selfhood in the Digital Age

11. Murder in the Dollhouse: The Jennifer Dulos Story

12. Bitter Brew: The Rise and Fall of Anheuser-Busch and America’s Kings of Beer

13. Picking Up: On the Streets and Behind the Trucks with the Sanitation Workers of New York City

14. Beautyland: A Novel

15. Priestdaddy: A Memoir

16. They All Came to Barneys: A Personal History of the World’s Greatest Store

17. Advantage Players: Inside the Winning World of Casino Virtuosos, Master Strategists, and Mathematical Wizards

18. Gomorrah

19. Beautiful Boy

20. Bukowski: A Life

21. Fun Home

22. Save Me a Seat – On the Road with Hello Dolly!

23. Losing Big: America’s Reckless Bet on Sports Gambling

24. Blood in the Water: The Untold Story of a Family Tragedy

25. The Peepshow: The Murders at Rillington Place

26. Waiting for Britney Spears: A True Story, Allegedly

27. The Sympathizer: A Novel (Pulitzer Prize for Fiction)

28. Sister, Sinner: The Miraculous Life and Mysterious Disappearance of Aimee Semple McPherson

29. Little Bosses Everywhere: How the Pyramid Scheme Shaped America

30. What Really Happens in Vegas: True Stories of the People Who Make Vegas, Vegas

31. A Good Walk Spoiled: Days and Nights on the PGA Tour

32. The War for Late Night: When Leno Went Early and Television Went Crazy

33. Care and Feeding: A Memoir – A Candid, Funny, and Devastating Story of the Food World and a Cultural Reckoning

34. The Racket

35. Funny Because It’s True: How The Onion Created Modern American News Satire

36. Meltdown: Greed, Scandal, and the Collapse of Credit Suisse

37. Season on the Brink: A Year with Bob Knight and the Indiana Hoosiers

38. No Limit: The Rise and Fall of Bob Stupak and Las Vegas’ Stratosphere Tower

39. Grandissimo: The First Emperor of Las Vegas

40. The Absinthe Forger: A True Story of Deception, Betrayal, and the World’s Most Dangerous Spirit

41. Answers in the Form of Questions: A Definitive History and Insider’s Guide to Jeopardy!

42. All That Glitters: A Story of Friendship, Fraud, and Fine Art

43. Selling Sexy: Victoria’s Secret and the Unraveling of an American Icon

44. The Money Trap: Lost Illusions Inside the Tech Bubble

45. A Moveable Feast

46. Down and Out in Paris and London

47. The Last Kilo: Willy Falcon and the Cocaine Empire That Seduced America—An Epic Narco Story with Unmatched Intrigue and Corruption, Experience the Rise and Fall of a Drug Empire

48. The Devil at His Elbow: Alex Murdaugh and the Fall of a Southern Dynasty

49. The Siege: A Six-Day Hostage Crisis and the Daring Special-Forces Operation That Shocked the World

50. Box Office Poison: Hollywood’s Story in a Century of Flops

The Knicks imploded at home. They blew a 14 point lead with three minutes left, and then lost in overtime. Their collapse was nasty, brutish, and short.

This year’s Knicks team, more than any other, embodies a New Yorker’s hopes and dreams. It’s a bunch of long-time friends coming together to outperform expectations, to make things happen in a difficult and competitive environment.

When they lose like they did last night, the Knicks suddenly embody all of New York’s collective fears. Your landlord will jack your rent. Your corner bar will close. Your Citibike dock will be empty. Your subway train will be delayed. You are not going to make it here. You are not going to make it anywhere.

Basketball’s just a game, but the Knicks collapsing feels serious. The Knicks become a pincushion, a voodoo doll exerting psychic pain on millions of New Yorkers. Between the bad weather and the bad loss, an angry undercurrent is going to run through New York for the next two days. Pedestrians’ tempers will run shorter, drivers’ horns will sound louder. The city will feel different than it did on Monday. The optimism, and the sun, are gone. Let’s hope that both the sun and the Knicks come back.

After the sessions, many of those same attendees are going to leave the conference center, hit the casino floor, and get hosed. It doesn’t matter whether it is slots, craps, roulette, or blackjack, casinos are designed to take money and they are quite good at it. Meanwhile, Vegas casinos are raising bet minimums, lowering odds via rule changes (Hello triple-zero roulette), and worsening service.

Sure, there are ways to hypothetically make money within a casino’s walls. You could play poker or count cards in Blackjack. Both require a large amount of skill, practice, and concentration (and for card-counting, subterfuge). These can be positive expected value but have immense variance. Even on a good day, they are very hard ways to make an easy living, and not how I want to spend valuable free time after a long conference day.

We can’t beat the house, but what if we could make the house bleed a little bit. Like Rocky, we can’t win against Vegas’s Apollo Creed, but we can make them go twelve rounds. How? Pai Gow Tiles.

Before I dive more into what Pai Gow Tiles is and why it enables this, I want to establish criteria for what getting value from gambling looks like. We’re very likely going to lose money at the table, so what matters is how much entertainment we get for that money. Think about it like going to a movie. If it costs $50 for two tickets, popcorn, and sodas for a ninety-minute movie, it is effectively $1.80 per minute of entertainment. Don’t do calculations here too literally. The amount of entertainment per minute is going to vary a lot based on the movie, and I’d rarely wish that a movie is longer so that I get more “value” for my money. The point is that it is normal to spend money to be entertained, and gambling should be viewed with the same lens.

So, what makes gambling in a Vegas casino entertaining? Personal opinion, but I’d say

1. How fun is the game itself?

2. How is the atmosphere and service?

3. Do you leave with good stories?

Our goal is to maximize those three while losing the least amount of money per hour. No table game comes close to Pai Gow Tiles.

Pai Gow Tiles is a Chinese gambling game allegedly dating from the Song dynasty. In Vegas, it can be found in a small number of casinos on the Strip. Instead of a deck of cards, it uses a “deck” of thirty-two tiles (effectively dominoes). I’ll skip an in-depth description of how it is played, (you can find a video here), but I definitely find it very fun. It is mentally engaging (lots of strategy to memorize, recall, and apply) and tactile (you roll dice and move the tiles). It avoids the robotic right answers of Blackjack or the mindless lack of meaningful choice in Craps. The best part, however, is the pace.

Pai Gow Tiles has, by far, the lowest amount of times an hour where you will win or lose money of any casino game (excluding poker). Half of all rounds lead to a tie, where no money is won or lost. Between each round, the “deck” of tiles needs to be hand-shuffled. Imagine if the dealer had to stop and re-shuffle after every hand of Blackjack. Shuffling tiles is much more involved than shuffling cards, and much more time-intensive. This means you can sit for a lot longer while actually risking a lot less. Your expected value per round is worse than Blackjack (although better than most other casino games), but there’s an order of magnitude less rounds per hour, so, odds are, you’ll end up losing less money.

Now, sitting around is great and all, but only if the atmosphere and service makes doing so enjoyable. Pai Gow Tiles is relatively unpopular in Vegas. Only a few casinos have it, and I’ve never seen more than one table. From talking to pit bosses, the main player base for Pai Gow Tiles in Vegas consists of Asian high-rollers, which is what justifies keeping around a unique, unpopular, and intensive game to run. The singular table, combined with targeting high-rollers, means that the tables are often in the high limit room of the casino. Bet minimums are not low (e.g $100/hand) but are far lower than a Blackjack table in the same room. This, combined with the slow pace, means you can risk a relatively small amount of money to be in the nicest area of the casino.

Vegas may be squeezing most folks, but they know where their bread is buttered, and still treat high rollers well. Just by playing in the high limit room, you’re generally in an ornate area getting the best service from the best dealers, pit bosses, and waitresses the casino has. Cocktail service is much better (both in terms of speed and quality). instead of a plastic cup of club soda or a shot of Jim Beam, you’re getting bottles of Perrier, crystal glasses of Japanese whiskey, cigars, and more. This is all very fun and does also potentially impact your expected value. Getting an $8 sparkling water or an $80 glass of whiskey for “free” meaningfully offsets your expected losses.

So, do you get good stories? I’d say so. I stumbled on Pai Gow Tiles during a holiday weekend in Atlantic City where it was the only table game with empty seats. From there, to Vegas high-limit rooms watching as the person on my right bet $10,000 a hand, to this blog post, it’s led to some memorable stories over these past eighteen months. If you’re gonna gamble, you may was well get your money’s worth, and Pai Gow Tiles is a great way to do so. Check it out the next time you’re in Vegas or Atlantic City.

In 2024, I read 41 books. I mostly chose these based off of recommendations (primarily from in-person conversations), and keep a running list of books that I may want to read next. The recommendations I get are (normally) good, and it’s fun to be able tie a book to how you first heard of it. Given I rely so much on other people’s picks, I thought it’d be helpful for me to share my own.

I mostly read non-fiction. These are books that were new to me in 2024, so plenty of them are years (or even decades) old. I’ve highlighted three books were lesser known to me (e.g no cultural phenomenons or TV/Movie adaptations) that I particularly liked. Beyond that, I’m going to avoid including authors, blurbs, or my own personal thoughts. That’s partially laziness, but partially because it’s fun to pick books just off titles.

My Three Picks

1. In My Time of Dying: How I Came Face to Face with the Idea of an Afterlife

2. Mindf*ck: Cambridge Analytica and the Plot to Break America

3. All the Living and the Dead: From Embalmers to Executioners, an Exploration of the People Who Have Made Death Their Life's Work

The Rest

1. Bandit Heaven: The Hole-in-the-Wall Gangs and the Final Chapter of the Wild West

2. Borstal Boy

3. All the Worst Humans: How I Made News for Dictators, Tycoons, and Politicians

4. The Odds: One Season, Three Gamblers And The Death Of Their Las Vegas

5. The Barn: The Secret History of a Murder in Mississippi

6. My Week at the Blue Angel: And Other Stories from the Storm Drains, Strip Clubs, and Trailer Parks of Las Vegas

7. Beneath the Neon: Life and Death in the Tunnels of Las Vegas (Travel Holiday Guides)

8. There Will Be Fire: Margaret Thatcher, the IRA, and Two Minutes That Changed History

9. The Club: How the English Premier League Became the Wildest, Richest, Most Disruptive Force in Sports

10. Fat Leonard: How One Man Bribed, Bilked, and Seduced the U.S. Navy

11. Rejection: Fiction

12. Never Saw Me Coming: How I Outsmarted the FBI and the Entire Banking System-and Pocketed $40 Million

13. Mississippi Swindle: Brett Favre and the Welfare Scandal that Shocked America

14. McMillions: The Absolutely True Story of How an Unlikely Pair of FBI Agents Brought Down the Most Supersized Fraud in Fast Food History

15. Red Plenty

16. Willie, Waylon, and the Boys: How Nashville Outsiders Changed Country Music Forever

17. Sid Meier's Memoir!: A Life in Computer Games

18. The Talented Mrs. Mandelbaum: The Rise and Fall of an American Organized-Crime Boss

19. Guilty Creatures: Sex, God, and Murder in Tallahassee, Florida

20. Random Family: Love, Drugs, Trouble, and Coming of Age in the Bronx

21. Fuccboi: A Novel

22. Life Sentence: The Brief and Tragic Career of Baltimore's Deadliest Gang Leader

23. Opposable Thumbs: How Siskel & Ebert Changed Movies Forever

24. Where Are Your Boys Tonight?: The Oral History of Emo's Mainstream Explosion 1999-2008

25. Down the Drain

26. Rogues: True Stories of Grifters, Killers, Rebels and Crooks

27. Stung: The Incredible Obsession of Brian Molony

28. Default: The Landmark Court Battle over Argentina's $100 Billion Debt Restructuring

29. Capote's Women: A True Story of Love, Betrayal, and a Swan Song for an Era

30. We Own This City: A True Story of Crime, Cops, and Corruption

31. The Counting House

32. Among the Bros: A Fraternity Crime Story

33. The Fund: Ray Dalio, Bridgewater Associates, and the Unraveling of a Wall Street Legend

34. A Drinking Life: A Memoir

35. The Matter of the Heart: A History of the Heart in Eleven Operations

36. Fire in the Belly: The Life and Times of David Wojnarowicz

37. A Furious Devotion: The Life of Shane MacGowan

38. The Wrong Stuff

Read any of these? Have any more recommendations? Please send thoughts and new book recs my way!

One of the men rifled through his pockets and pulled out a deck of cards. He started shuffling, before launching into twenty minutes of rapid fire card tricks and stage banter. They were magicians. Their showtime for Speakeasy Magick, an accompaniment to the famous Sleep No More, had finished for the night, and Billymark’s was close to the venue. These people clearly loved what they did, and never wanted to stop their act.

I was never able to get tickets to Sleep No More, or Speakeasy Magick, but I got a show that night. An out-of-the-blue show driven by passion, totally devoid of any financial incentives. That was Billymark’s in a nutshell. A bar fueled by passion. A bar owned by the two namesake brothers, who had bought up lots of primo Manhattan real estate in the 70s and 80s, which meant they didn’t need to be running a bar.

And still, they did. They alternated manning the bar, opening it up faithfully at 8am, every day of the week, for decades. Mark’s a (to me, lovable) asshole, Billy is way nicer. Neither of them needed to deal with the mix of drunks, tourists, MSG attendees, magicians, and partiers that they had on a daily basis, but they did.

Until this year. Billymark’s closed. Thankfully, the close was not due to the ever-common rent hikes, but to the brothers’ retirement. It may even come back. The for-rent sign comes and goes, and articles published months before closing give a little bit of hope.

For now, it’s gone. Cynically, it’s likely to stay gone. Even if it comes back, it can’t be the same. You can’t hand off the brother dynamic. You can’t hand off fifty years of manning the bar. You just wait, bemoaning the deaths of places you care about which all replaced the places that other people cared about. It’s the cycle of life. There were few better bars to think about your other favorite bars closing, your day going sideways, or the Knicks losing. Let’s hope, just like those magicians, Billymark’s has a few more tricks left up its sleeve.

(Photo from Lloyd Wise)

Why are some gray-area companies able to reach escape velocity while others crash and burn? I've been mulling this over as I've seen the rapid rise of online sweepstakes-based sports betting sites. I met a sports-book founder in February who was going through the insanely arduous process of getting licensed state-by-state. A few months later, they pivoted and were suddenly able to launch a quasi-legal sports-book in 40+ states, including California, Florida, New York, and Texas. They are not alone. A dozen startups have launched or pivoted, taking advantage of what they see as a goldmine of legislative loopholes. What's going to happen to these companies? Are there generalizable rules to when pushing the regulatory envelope can work?

First, a brief overview of what "sweepstakes" betting is. Remember the McDonald's Monopoly game? You buy something that is not a lottery ticket (food) and they give you a lottery ticket where you can win free fries or some money. Sweepstakes gambling is that taken to the extreme. You buy virtual currency (which has no value and cannot be exchanged) and, alongside, get a different form of virtual currency that can be exchanged back for cash. Birches Health, a gambling addiction treatment company (and Healthie customer!), has an in-depth (albeit opinionated) explanation here. Licensed New York sports-books like FanDuel and MGM pay 51% tax on gross revenue; these sweepstakes betting companies pay 0%. That's clearly not sustainable.

Are these companies going to make it, or are they going to get crushed? I call the determining criteria Hide-Fight-Run 

1. What is the risk of newsworthy direct harm done by the gray-area product? (Hide)

2. What is the size and fragmentation of the gray-area product's competitors? Can the fish eat the whale? (Fight)

3. How differentiated is the gray-area offering from legal alternatives? (Run)

In short, if a company can hide from serious negative public opinion, have a path to fighting back directly against incumbents, and keep distance from its competitors and then shirking regulations can potentially work. Otherwise, it ends in disaster. 

Let's apply hide-fight-run to the early stages of Airbnb.

1. Airbnb has gotten plenty of bad press for things like raising housing prices, creepy hosts, and nuisance party houses, but ultimately Airbnb is insulated. It is too easy to muddy the waters around the discussion on housing prices, and Airbnb can point to their terms of use and safety programs for any sort of host or guest misconduct.

2. There are very large hotel groups like Hilton and Marriott, but ultimately there are a bunch of them. There are also franchisees, independent operators, boutiques, etc. Airbnb had the opportunity to be as large as or larger than any one of them.

3. Airbnb (at least in the early days) was very different from booking a hotel. It added lots of new types of housing options and locations, could be much cheaper, and promised a more local and authentic experience.

Hide-Fight-Run shows that Airbnb was loved by consumers, initially looked over by competitors, had enough potential to be backed by deep pockets, and avoided stories that could have overwhelmingly stoked public opinion against them.

Now, let's look at Napster.

1. Napster's bad press was more centered around the damage to musicians and music, but ultimately limited.

2. In 2000, the music industry was concentrated across the big five record labels, which were large and dominant and had a strong lobbying arm in the Recording Industry Association of America. Napster never made any real money and did not have a clear path to doing so.

3. Napster was great for consumers (it was free), and a very different experience from having to go to a record store to buy CDs.

Or Juul:

1. So much bad press (due to instigating an entire teenage vaping epidemic) led to regulatory crackdowns.

2. The tobacco industry is highly concentrated into a big five but was an industry in decline that needed new innovation. Vaping offered the potential of a "healthier" alternative that could leapfrog existing tobacco products.

3. New, differentiated product. Better user experience than traditional cigarettes.

In these cases, despite beloved products, the companies were either too small to take on entrenched giants or too problematic to survive regulatory scrutiny.

So what about "sweepstakes" sportsbooks?

1. Gambling (especially online) already gets a lot of bad press, including vivid articles about individuals who ruined (and even ended) their lives. Sweepstakes sites have less regulation, less money laundering controls, contribute less to gambling addiction prevention, and do not provide meaningful revenue to the government (which is the largest argument in favor of legalized gambling). They are sitting ducks for damaging articles.

2. The top six U.S. sportsbooks dominate the market (having close to 90% market share). Many have ties to massive multinational casino chains (like Caesars, MGM, or Hard Rock).

3. The products look and function just like legal sportsbooks. The odds offered (effectively the cost to consumers) are very similar to legal sportsbooks. There is currently a large benefit to consumers in states like California, which have no legal online options and otherwise would have to use sketchy overseas sportsbooks or illegal local bookies. Consumers do not get any protections from gaming control boards (as these sweepstakes sites are not regulated by gaming control).

That is a grim combination. Without large product differentiation, it is hard to imagine the sweepstakes sites getting bigger than incumbents like FanDuel or DraftKings. These sites have a large target on their back from both governments (which want tax revenue) and legal sports-books (which hate having to pay taxes). They do not provide any social good or meaningful consumer benefit (besides skirting the laws). They will very visibly do harm. They fail the test of where pushing the envelope can work.

The sweepstakes wave is cresting and will crash down. We'll see states move to close loopholes, with some legalizing online sports betting and taxing it heavily. These sweepstakes companies will either ultimately fail, sell for their tech and people, or struggle to go back to a state-by-state framework and compete with dominant incumbents. On a personal level, this is somewhat of a shame as more competition leads to better prices and better products. These upstart companies are doing intelligent and innovative work, and no one should have sympathy for large casino corporations and sportsbooks. For better or worse, it won't matter. When it comes to regulating gambling, if you walk and talk like a duck, you'll get hunted like one.

n.b: You know what’s a lot more fun than stressing about the legalities of your startup? Working at a fast-growing HITRUST-certified health tech company that cares a ton about security and compliance. We’re hiring at Healthie!

Punk Island is a collectively organized, free, all-ages, all-DIY music festival that’s traditionally been held on Randall’s Island (a small island in between Queens and Manhattan). There’s a bunch of stages with simultaneous performances, all organized by different groups, that put on about eight hours of live music. It’s awesome, an amazing example of grassroots execution, but it’s a lot more than that.

The summer of 2019 was a heady time. Healthie had emerged from a tumultuous period and was back on a growth trajectory. I turned 22, wasn’t working 90 hour weeks anymore, and could afford rent. The combination of sticky June weather, Corona 30ozers, and some of my favorite bands felt like a graduation. I’d gone from playing little league baseball on Randall’s as a kid, to what felt like the big leagues, the start of real independence.

The summer ended, and we became a lot more familiar with Coronaviruses than Corona Familiar. Punk Island was cancelled for two years, happened on a very small scale in 2022, and was on a Bay Ridge pier in 2023.

On June 8th, 2024, five years later, Punk Island came back to Randall’s. It felt like a homecoming. The world’s changed. The bands changed. I’ve changed. The circle comes back around.

Traditions serve as a waypoints. They are mile markers to demarcate all that is different, and to celebrate what was sturdy enough to remain. It’s good to be here.

(all photos from Brooklyn Vegan)

Even with the inherent disadvantages, horse racing tips and strategies abound. They have fun names like “Yankee” and “Dutch”. I don’t know if they work (although I strongly doubt it). I don’t know anything about horses or the nuances of horse racing. However, eight years in health tech has taught me a lot about writing software around regulatory intricacies. When I learned about an interesting U.S law, I figured it’d be a fun weekend project to see if it could be used as the base of a provably profitable horse racing strategy. Here’s what I found.

First, some background on horse racing and betting on races. Most importantly, race betting in America is parimutuel. When you place a race bet with FanDuel, DraftKings, or at the track, you are not actually betting against them. Instead, your money is pooled with all other gamblers who placed the same type of bet. The bet taker (e.g the track) removes and keeps a fixed percentage of money from the pool (the “takeout” or “vig”), and the remaining money is paid out to the winning bettors. We’ll dive more into how those payouts are calculated, but this is extremely different then betting on sports. Some of the key differences:

1. Your odds (and thus your potential payout) change after you place your bet. Your payout is based on the pool at the time the race starts, so odds shift based on bets placed after yours.

2. The “takeout” percentage is brutal. It varies, but is incredibly high across the board. Churchill Downs (the host of the Kentucky Derby) takes out 17.5% which is pretty standard. For comparison, betting on an NFL point spread (at -110 odds) has a “vig” of 4.76%. Betting on horses is like if NFL spreads were priced at -140.

3. There is “breakage”. To make things even worse, payouts are rounded down to the nearest dime. 1:9 (the lowest odds you’ll see) is actually paid out at 1:10.

This has some big impacts

1. There’s no such thing as locking in good odds early. Odds change after you bet, so even you had insider info on a horse, you gain no first mover advantage. This uncertainty causes a large rush of bets right before the race starts.

2. To overcome the takeout and breakage, you’d need to be right an incredibly high amount of the time. If you’re betting on a horse that priced at even money (e.g a horse with implied odds of 50% chance of winning), you’d need to be correct more than 57% of the time.

This makes horse betting impossible to win at without inside information, true divine inspiration, or legislative intervention. Let’s explore the last one.

Here’s an example pool for a “show” bet, which is betting on a horse to finish in the top 3.

Let’s assume Homer finishes in the top 3. To calculate winnings, you

1. Take the total pool size ($1,030)

2. Take out the “vig” (17%, leaving you with $854)

3. Subtract the total amount bet on horses that finishes in the top 3 ($854 - $1,020, for -$166)

4. Divide that by the number of winners (-166 by 3, for -$55)

5. Divide that by the amount bet on the horse you bet on (e.g -55 by 1000 for Homer, or -55 by 10 for Marge)

6. Wait a minute, that’s a negative number

In certain situations where there’s an extremely heavy favorite, the calculated payout is negative. If you bet a dollar on Homer, the math has you receiving 95 cents back, even though your bet won. This is called a minus pool.

Losing money on a winning bet doesn’t sound fair. The government agrees. U.S gaming commissions impose minimum payout rules. A $1 bet needs to pay at least $1.05. For tracks in West Virginia, it’s a minimum of $1.10. The difference between the pool and the minimum payout has to be paid by the track.

This side-steps the aforementioned issues that make horse racing so hard to beat. When you bet a favorite in a minus pool, you are getting fixed odds (-1000 in West Virginia, -1900 elsewhere), inverting the “vig”, and forcing the track to take a side. This doesn’t inherently make betting the favorite in a minus pool profitable, but it opens up the potential for it to be.

For this strategy to be profitable and usable, a couple things need to be true.

1. Minus pools need to exist in real life. If they only occur once in a blue moon, then trying to identify and bet on them is impractical and effectively pointless. We need them to happen regularly for us to have enough historical data to calculate expected value, and also to be able to actually have something to bet on.

2. Favorites need to win, and win a lot. In West Virginia races (which have the most favorable laws), your “show” bets need to win more than 90.91% of the time.

So, are those two things true? I had no clue, but the fun is in finding out!

Quick aside, The current state of horse racing is problematic. While this strategy would potentially be taking money from the tracks, race betting is fun but ultimately pointless. There are much more important problems to solve, and we’re tackling some of them at Healthie. Come join our team!

To answer those two questions, we need data, and a lot of it. Does horse racing generate enough data points, and is that data accessible? The answer, surprisingly to me, was a resounding yes.

I was blown away by the breadth, maturity, and openness of race betting is in the U.S. The first surprise was the amount of bettable horse races. There are tracks all over the world, and with the ranges of timezones, races are happening 24/7. No matter what site you bet on, or even if you bet in-person, you are betting into the same pool. You can watch any of these races online, completely for free. There are 2,460 games in the six month NBA season. There are more than 3,000 horse races every week.

Data is powerful, and horse racing generates a ton of data. The data is also surprisingly easy to access. There are big businesses built on buying and selling clean and accurate historical sports datasets. You can write simple code to ingest years of racing data directly from the primary source.

I like writing code, so I did that. I spent a few hours building a data set of tens of thousands of past results. With that, these questions become straight-forward to answer.

1. Minus pools happen with decent frequency. There have been more than 130 in the past seven days.

2. Favorites win a lot, but not enough. Looking at all minus pools in the data set, the favorite finishes in the top 3 (e.g wins the “Show” bet) about 80% of the time. That’s far below the 90.91% we need to be winners.

The good news is, we have tons of data! That 80% number is across all races. We can further segment the races to try and identify which ones would be profitable. There are a couple key factors that stood out.

1. How many horses are running. The Kentucky Derby has up to 20 horses in the race. That’s a lot! The number of horses varies between races and it is common to have just five or sometimes even four horses in a race. A “show” bet is placing in the top three, which should be much easier to predict in a race with less horses.

2. How much has been bet in the pool. Some races have under $100 bet on them. The efficiency of horse racing markets is a whole separate topic, but while they can be quite inefficient, a ten thousand dollar pool seems like it would a stronger signal that a fifty dollar one.

3. How much of the pool is concentrated on the top three favorites. It feels easier to predict a top three finish in a five horse race with two extreme long-shots.

Playing around with these variables, I determined two situations where betting a favorite minus pool at a West Virginia track is profitable.

The first is when a race only has four horses. This makes sense, since only one horse will finish outside of the top three. Four horse races that offer “Show” bets are rare, and are normally the result of a horse being removed from the race at the last minute. Historically, the minus pool “show” bet wins 93.75% of the time (above the all important 90.91%). This percentage goes up when you only look at races with a pool over $1,000.

The second are five horse races with a large pool (greater than $2,000) where more than 90% is concentrated on the top three favorites. This bet wins 91.08% of the time, which while lower, is still above the break-even point. That’s pretty neat.

There’s almost certainly room to improve those percentages (or find more scenarios) by digging deeper into other variables. Races vary in length, riding style, track surfaces, and horse ages all in ways that could potentially impact outcomes.

At the end of day, researching and writing code to dig into this is a lot more fun than using the strategy would be. This is the definition of picking pennies up in front of a steamroller. You need ten straight wins to offset one loss. Even if executed perfectly, you’d be dealing with immense amount of variance, just to earn less money than you would by keeping a bankroll in a high-yield savings account.

I’ve only been to a horse race once. My granddad took me once when I was sixteen, and I had a lot of fun getting him to place $2 bets based on which horse name I liked the most. This strategy is little more data-driven, but of pretty similar utility. Diving deep here likely won’t lead to any money, but it will make you a great conversationalist on West Virginia gaming regulation. What’s better than that?

New York City has a lot of Irish bars and a lot of bar closings. McQuaids was a great, long-running bar but far from as old as McSorely’s or as acclaimed as The Dead Rabbit. 

What it was, for all but the last few years of its existence, was a single story. That changed, not due to a corporate firm, or a rich real estate investor, but due to the owner of the bar and the building, Tom McQuaid.

Hell’s Kitchen has been a rapidly changing area. New high rises sprout up, a Target opens, the neighborhood shifts. Ultimately, like Manhattan as a whole, the progressive drumbeat pushes buildings ever upwards towards the sky. 

Most of this progression is driven by outsiders. Foreign firms build and bankrupt condos, real estate corporations come in with sophisticated plans and piles of money. They buy out existing owners to enable their grand visions. In the face of outside cash and the air of inevitability, people sell, and rationally so. 

Tom did not do that. Tom borrowed a lot of money against his building, and built five new stories of office space. He had to shut down the bar for construction, and McQuaids was temporarily closed for years as the work was done. 

This is about the time I moved to the neighborhood. Drinking at different places in the area, it was common to run into McQuaids refugees, barflies and bartenders who were biding their time, waiting to return to McQuaids once it reopened. I’d walk by and peer in the windows, to try to get a sense of why these folks loved this place so much. 

The construction finished, and reopening was scheduled, as planned, right before St. Patrick’s day. McQuaids soft re-opened, with both a gleaming bar interior and a large “office space for rent sign”, on March 10th, 2020. 

Then, as we all lived through, the world fell apart. McQuaids did reopen that summer, serving five dollar pints of Guinness (real pints) out of a window. The “for rent” sign remained. It’s hard to imagine a worse time to be involved in both the bar and commercial real estate business. 

New York has recovered in its own scarred way, jagged and lovable. Eleventh Ave office real estate, never a hotspot, has not. Oglivy, the large ad agency whose presence on 11th was worthy of a brass plaque on their building, moved downtown in 2021. The floors above McQuaids remained vacant.

Even as the bar fully reopened, the upper floors have stayed empty. Those floors became an albatross, and without tenants, look to have forced Tom to close and sell the whole building.

The limited news coverage has been pretty rough on Tom. It talk about a “novice developer squeezed”, and “blue collar people who had to keep up coming up with money.” This coverage misses the point.

I am far from knowledgeable on both running bars or owning office space. I have no clue on the veracity of the news coverage. What I do know, is that Tom McQuaid built five stories. 

In doing so, when so many others sold and left, Tom’s become the Man in the Arena personified to me. To paraphrase Teddy Roosevelt, the critics and backseat drivers don’t matter. Tom McQuaid’s plan may have not have worked, but at least it was audacious. It failed, but failed by daring greatly. That is chutzpah. That is heart. What could be more admirable than that? 

(photos from Phil O’Brien at w42st.com)

Given that this anonymity and privacy comes from what seems like complete human-to-human indifference, it’s easy to assume that New York is a cold uncaring place. We are, after all, the home of the Kitty Genovese murder, in which dozens of New Yorkers heard a woman get murdered  and did close to nothing. This incident led to the creation of the bystander effect theory, and has done no favors to New York’s reputation. New York gets an unfairly bad rap here. These notable failings are outweighed by the solidarity and kindness New Yorkers display to each other on an every day basis. The true measure of this is not the outliers, the Kitty Genoveses and subway saviors that hit the news, but the margins. It is the small actions, taken every day by millions of New Yorkers, that make New York what it is. 

When people ask me about living in New York, there’s one story I always tell. I’m walking back home from a deli, with a brown paper bag full of beer, when it starts to pour. The bag gets soaked. Between the sogginess and the weight of the cans, it splits open, sending tall boys careening in all directions on the Tenth Avenue sidewalk. Before I know it, a reusable bag is pressed into my hand, the cans are brought back and packed, and I’m quickly on my way. Four total strangers, with no hesitation, obligation, or words, coming together to make my life a little easier. A NASCAR pit crew could not have done it better. That is solidarity. That is New York. 

In 2023, I read 47 books. I mostly chose these based off of recommendations (primarily from in-person conversations), and keep a running list of books that I may want to read next. The recommendations I get are (normally) good, and it’s fun to be able tie a book to how you first heard of it. Given I rely so much on other people’s picks, I thought it’d be helpful for me to share my own.

I mostly read non-fiction. These are books that were new to me in 2023, so plenty of them are years (or even decades) old. I’ve highlighted five books were lesser known to me (e.g no cultural phenomenons or TV/Movie adaptations) that I particularly liked. Beyond that, I’m going to avoid including authors, blurbs, or my own personal thoughts. That’s partially laziness, but partially because it’s fun to pick books just off titles. It can also lead to happy accidents (like when I read two great books called “Last Call” since that is all I wrote down, and I wasn’t sure which one it was)

My Five Picks

1. Hotel Splendide

2. Brutalities: A Love Story

3. American Roulette: How I Turned the Odds Upside Down---My Wild Twenty-Five-Year Ride Ripping Off the World's Casinos

4. Among the Thugs

5. Up in the Old Hotel: Reportage from "the New Yorker"

The Rest

1. Bullshit Jobs: A Theory

2. To the One I Love the Best

3. How to Murder Your Life: A Memoir

4. Killers of the Flower Moon: The Osage Murders and the Birth of the FBI

5. The Corner: A Year in the Life of an Inner-City Neighborhood

6. Empire of Pain: The Secret History of the Sackler Dynasty

7. A Fever in the Heartland: The Ku Klux Klan's Plot to Take Over America, and the Woman Who Stopped Them

8. Going Infinite: The Rise and Fall of a New Tycoon

9. The Cap: How Larry Fleisher and David Stern Built the Modern NBA

10. Gambler: Secrets from a Life at Risk

11. What Do You Care What Other People Think?: Further Adventures of a Curious Character

12. Destiny of the Republic: A Tale of Madness, Medicine and the Murder of a President

13. Manhattan Cult Story: My Unbelievable True Story of Sex, Crimes, Chaos, and Survival

14. Casino-ology: The Art of Managing Casino Games

15. Heat: An Amateur Cook in a Professional Kitchen

16. The Last Action Heroes: The Triumphs, Flops, and Feuds of Hollywood's Kings of Carnage

17. Billionaires' Row: Tycoons, High Rollers, and the Epic Race to Build the World's Most Exclusive Skyscrapers

18. The Boys on the Bus

19. Stoned: Jewelry, Obsession, and How Desire Shapes the World

20. The White House Plumbers: The Seven Weeks That Led to Watergate and Doomed Nixon's Presidency

21. Whitey's Payback: And Other True Stories: Gangsterism, Murder, Corruption, and Revenge

22. Dealt: Stories from My Life on the Felt

23. The Wager: A Tale of Shipwreck, Mutiny and Murder

24. Eli and the Octopus: The CEO Who Tried to Reform One of the World's Most Notorious Corporations

25. Hood Feminism: Notes from the Women That a Movement Forgot

26. The Snakehead: An Epic Tale of the Chinatown Underworld and the American Dream

27. Happy at Any Cost: The Revolutionary Vision and Fatal Quest of Zappos CEO Tony Hsieh

28. Unscripted: The Epic Battle for a Media Empire and the Redstone Family Legacy

29. The Dispossessed

30. Last Call: The Rise and Fall of Prohibition

31. Last Call: A True Story of Love, Lust, and Murder in Queer New York

32. How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence

33. Say Nothing: A True Story of Murder and Memory in Northern Ireland

34. Endurance: Shackleton's Incredible Voyage

35. Boundless: The Rise, Fall, and Escape of Carlos Ghosn

36. St. Marks Is Dead: The Many Lives of America's Hippest Street

37. Money Men: A Hot Startup, A Billion Dollar Fraud, A Fight for the Truth

38. Then One Year...: History's Craziest Year as Seen by a Las Vegas Bookmaker

39. Low Life: Lures and Snares of Old New York

40. The $12 Million Stuffed Shark: The Curious Economics of Contemporary Art

41. Barnum

42. Freedom

Read any of these? Have any more recommendations? Please send thoughts and new book recs my way!

When you’re stuck in a bedroom, unable to go elsewhere, there’s something comforting about listening to to sometimes unintelligible, always well-written songs about better times. 

The more I played the Pogues during the pandemic, the more the I ended up connecting with their lead singer. 

Like me, Shane MacGowan was Irish, but not born in Ireland. He brought Irish folk music inspirations to generations of kids who felt a little too cool to listen to the The Chieftains. The Pogues served as an emotional bridge between the punk music I love, and my nostalgia-tinged memories of child car rides full of Fields of Athenry and Irish Soldier Laddie.

Since  the 1980s, Shane often seemed six months away from death. In January 2022, I began to feel that way. Seemingly overnight, while in a foreign country for a month, I began having severe health scares. I went from being able to exercise for hours, to my chest seizing up, and my borderline passing out while in the ocean or on a hike. Each time, no matter how dizzy I felt, how blurry my vision got, or how intense the chest pain was, I was convinced it was an isolated anomaly that would not happen again. I don’t know how Shane felt, but to me, at the time, it was clear. It made more sense to ignore everything, without admitting to any health issues, than to directly face whatever the hell was happening to me. I’d climb up to the roof each night with a beer, stare at the ocean, and listen to the Pogues through my tinny phone speakers. 

This is objectively not the way I should have dealt with a situation like that. Clearly, Shane was not a positive influence on my life, much like he did an immense amount of unneeded damage to his own. That said, I know very few geniuses and very few poets. I’m not either. Shane was both. 

 As a young person looking to make connections, your cold outreach is already starting at a large advantage. Execs generally want to help folks just starting off. This can be for moral/personal reasons (e.g. we got a lot of help when we were starting out, and want to continue to pay that forward). It also makes good business sense. The young people taking initiative today will soon be the customer, partner, or employee of tomorrow. It’s also to fun to catch smart people at the beginning of their careers, the sense of opportunity is palpable. 

In an email inbox full of spam, sales pitches, and notifications, it is easy for your email to stand out. You want it to stand out the right way. The below email did not do that, and prompted this post. Read through the below (sender identifying info redacted) and see if you can identify what bothered me so much.

There’s some smaller (albeit important) spelling and grammar stuff like “alma” being misspelled, but one major thing stood out to me. The message is completely unpersonalized (there is no mention of my name or of Healthie) and I am literally bcc’d on the email. This person wrote a generic email, added a bunch of folks in the Healthcare IT space to the BCC list, and then blasted it out. This is something I’d expect out of offshore dev agency spam, not an email asking for a personal favor. An email like this takes away any initial good will, and makes me not want to help.

Ultimately, this email felt lazy. In life, it can be ok to be “lazy” about things. However, shortcuts can be taken only if you’re smart enough to not make the end-result feel like a shortcut. With bulk email, this is actually pretty straight forward. You can use mail merge and a spreadsheet to send out personalized emails to hundreds of people. I never would have known that I was one of many recipients, and honestly, I wouldn’t have cared if I did know. Working efficiently and automating tasks is a feature, not a bug. If you’re not able to automate the task, then it needs to be done manually and correctly, or not at all.

In contrast, here’s a cold email example that I thought was fantastic.

It is personalized, to the point, and has a clear ask. It is ultimately still pretty generic, but that is totally fine. I assume the sender sent similar emails to dozens of other companies. That is in no way a bad thing, and I absolutely would have done the same if I were in their shoes. The level of effort put into this email versus the “bad” email above is likely close to the same, but the output is wildly different. 

You don’t have to be Hemingway to make great connections via cold outreach. You do need to show that you (at least appear to) care. The sender of the “good” email ultimately became Healthie’s first engineering intern since COVID. The sender of the “bad” email did not get a response. Smart work can beat hard work, but both smart and hard work beat sloppy work.

The last one should be a given, but hasn’t always been. Pre-COVID, we were fully in-person, and were subletting an office from a company that moved out after they got acquired. 

The space was huge and pre-furnished, above a sketchy (but lovable) bar. The building was an old Garment District one that was slowly falling apart.

Our employees had mixed feelings. On one hand, the ping pong table was great! On the other, the block felt unsafe.  It was a close race, until the roaches appeared.

Nothing kills employee morale faster than roaches. No creatures are harder to kill. Exterminators came and went. The cockroaches ebbed, flowed, but ultimately always seemed to stick around.

At a certain point, a begrudging anthropomorphizing respect began to set in. These things were unkillable! Healthie had just gone through a huge layoff and  a nightmarish crunched product rebuild. We had taken a beating, and in the long hours and late nights, there’s an appreciation of kindred spirits that refuse to die. 

Years later, in late 2020, I was at a bar with a group of founders and a VC. The VC went around the circle asking about company spirit animals. Healthie was doing much much better at this point, and back on a growth trajectory. Still, I took pride in my answer, “cockroach.”

The VC recoiled. These were zero interest rate days. This was the time for explosive growth, not survival. This was not the answer to give if you needed to raise money. 

Thankfully, at Healthie, we didn’t have to. We were profitable and felt self-sufficient and in control of our destiny. 

Today, as we approach 2024, we feel the same way, but I no longer think cockroach was the right answer. Cockroaches are isolated. They survive seemingly anything, but no one wants to be around them. They feel solely focused on survival, and do not take any advantage of the upside of thriving or growing. 

It’s much better to be a company that can survive in the worst of times, but also excel in the best. I feel that’s what Healthie has been these past few years. We’ve grown an incredible amount (both in revenue and employee count), matured as an organization, and became a known name in our space. I don’t know what animal that maps to any longer, but I know it’s not a cockroach.

Survival mindset can turn into a starvation experiment if you’re not careful. Knowing when to bunker down, and when to try to focus on growth is a gut decision that doesn’t have a clear right answer in the moment. It’s a hard decision to make but it is critical, and ultimately a human one. Next time, I get asked the spirit animal question, I think I’ll go with “human.” 

In 2022, I read 49 books. I mostly choose these based off of recommendations (both online lists and from in-person conversations), and keep a running list of books that I may want to read next. Given that I rely so much on word of mouth, I thought it’d be helpful to share my own list and picks for the year.

I mostly read non-fiction. These are books that were new to me in 2022, so plenty of them are years (or even decades) old. I’ve highlighted five books were lesser known to me (e.g no cultural phenomenons or TV/Movie adaptations) that I particularly liked.

My Five Picks

1. The Invisible Hook: The Hidden Economics of Pirates

2. River of the Gods: Genius, Courage, and Betrayal in the Search for the Source of the Nile

3. American Fire: Love, Arson, and Life in a Vanishing Land

4. One of a Kind: The Rise and Fall of Stuey ',The Kid', Ungar, The World's Greatest Poker Player

5. Song of Spider-Man: The Inside Story of the Most Controversial Musical in Broadway History

The Rest

1. Bourdain: The Definitive Oral Biography

2. Tonight We Bombed the U.S. Capitol: The Explosive Story of M19, America's First Female Terrorist Group

3. Lights Out: Pride, Delusion, and the Fall of General Electric

4. Lying for Money: How Legendary Frauds Reveal the Workings of the World

5. Dark Trade: Lost in Boxing

6. The Comedians: Drunks, Thieves, Scoundrels, and the History of American Comedy

7. The Tender Bar: A Memoir

8. At the Sands: The Casino That Shaped Classic Las Vegas, Brought the Rat Pack Together, and Went Out with a Bang

9. Junky: The Definitive Text of "Junk"

10. Press Reset: Ruin and Recovery in the Video Game Industry

11. The Princess of 42nd Street: Surviving My Childhood as the Daughter of Times Square's King of Porn

12. Shantaram: A Novel

13. Attached: The New Science of Adult Attachment and How It Can Help You Find-and Keep-Love: The New Science of Adult Attachment and How It Can Help You Find--and Keep-- Love

14. Boardwalk Playground: The Making, Unmaking, & Remaking of Atlantic City: How the people of a New Jersey resort built a seaside paradise, lost it, rebuilt ... town, mostly lost it, and kept on dre

15. You Thought It Was More: Adventures of the World's Greatest Counterfeiter Louis The Coin - As seen on The History Channel & The BBC

16. Notes of a Dirty Old Man

17. The Logic Of Sports Betting

18. Salem's Lot

19. Showtime: Magic, Kareem, Riley, and the Los Angeles Lakers Dynasty of the 1980s

20. Then One Day ...: 40 Years of Bookmaking in Nevada

21. Tokyo Vice: An American Reporter on the Police Beat in Japan

22. Blood and Fire: The Unbelievable Real-Life Story of Wrestling's Original Sheik

23. Ball Four

24. Billion Dollar Fantasy: The High-Stakes Game Between FanDuel and DraftKings That Upended Sports in America

25. The Hot Hand: The Mystery and Science of Streaks

26. Party Monster: A Fabulous But True Tale of Murder in Clubland

27. The Club King: My Rise, Reign, and Fall in New York Nightlife

28. The Vig: Confessions of an Ivy League Bookie

29. Phil: The Rip-Roaring (and Unauthorized!) Biography of Golf's Most Colorful Superstar

30. Things Are Never So Bad That They Can't Get Worse: Inside the Collapse of Venezuela

31. And the Money Kept Rolling In (and Out) Wall Street, the IMF, and the Bankrupting of Argentina

32. I'm Glad My Mom Died

33. The Westies: Inside New York's Irish Mob

34. Retail Gangster: The Insane, Real-Life Story of Crazy Eddie

35. Born to Kill: The Rise and Fall of America's Bloodiest Asian Gang

36. Addiction by Design: Machine Gambling in Las Vegas

37. The Pyramid of Lies: Lex Greensill and the Billion-Dollar Scandal

38. Gaming the Game: The Story Behind the NBA Betting Scandal and the Gambler Who Made It Happen

39. DisneyWar

40. The Devil's Candy: The Anatomy Of A Hollywood Fiasco

41. Your Movie Sucks

42. Havana Nocturne: How the Mob Owned Cuba...and Then Lost It to the Revolution

43. Your Table Is Ready: Tales of a New York City Maître D'

44. The Lost Bank: The Story of Washington Mutual-The Biggest Bank Failure in American History

Stressful situations have always brought me clarity. As I sit here, on a quiet Sunday in an empty office, I want to use that clarity to take stock of the impact these ten years of heart issues have had on me. 

I was diagnosed with a congenital heart defect in 2012. Since then, I’ve had two open-heart surgeries, a heart attack, and innumerable doctor’s appointments. Frankly, I’ve had a worse-than-expected outcome at basically every step. The congenital defect is extremely rare, the first surgery was supposed to be the only one, that heart attack never really got explained, and the valve I get replaced tomorrow normally lasts much longer. I’m going to be dealing with heart issues for the rest of my life.

That’s all happened in the past ten years, and none of it is good. Yet, the past ten years have also been my best ones. I’ve been surrounded by incredible friends and loved ones. I’ve gotten to build a great company doing work that matters. I’ve had full athletic opportunities, becoming a league-champion wrestler, a (very bad) varsity college athlete, and a gym regular. I truly think those great things have happened because of, and not in spite of, my heart issues. My heart issues have given me drive, focus, and an invaluable sense of perspective. The contradiction I live with every day is that the worst moments of my life, and the outcomes I fear most, are why so many of these amazing things have happened. 

Thinking on that contradiction today, my main takeaway is I’m grateful. Not grateful for being in this position, but grateful for the people around me, and the time I live in. The line between benefitting from adversity versus being dragged down by it is razor thin, and I’m grateful I’m on the right side of it.

I’m grateful that my mom thought to ask our family pediatrician about one episode of me feeling dizzy on a treadmill, and that she got the right answer. I’m grateful that medical imaging technology existed to diagnose my defect, and that there was a proven surgical option to address it. 

I’m grateful that we have medical providers that listen to patient’s wishes. More specifically, to the surgeon who spent hours trying to repair my aortic valve during my second surgery before ultimately falling back to having to replace it. The repair didn’t work, and extended the surgery, but I had told the surgeon I wanted him to try it, and greatly value the closure from him having done so.

I’m grateful to the unknown horseback tour guide in Costa Rica this January. He saw me stumbling and dizzy on a hike, put me on his horse, and got me up to the top. I had just started to be symptomatic, thought it was just dehydration, and stubbornly assumed I could just keep on going. I’m grateful I didn’t find out how stubborn I could be. 

I’m grateful that the TAVR procedure is an option. Twenty years ago it didn’t exist. Five years ago, when I had my last surgery, it never would have been considered an option for patients in my position. Now, they can go and replace my heart valve through a small incision. It feels like sci-fi to me, and I’m grateful that I get some more time before getting my ribs cracked open again. I’m amazed everyday by innovation in healthcare technology. I’m optimistic that by the time of my next valve replacement, there will be even more options than we have today.

I think of my life in eras defined by my surgery dates. Since my first surgery, those eras have been in roughly five year increments, and I think each one has corresponded to a new phase of life events, achievements, and personal growth. With the TAVR, I enter a new one. The things that we can’t help but care about make us who we are. Reflecting on the past five years, I feel good about what I’ve cared about, and where I’ve spent my time. I’m excited to build on those in this next phase, and to have more things to be grateful for. 

Update - 9/27/2022: The TAVR went smoothly and I am already out of the hospital. Modern medicine can feel like a miracle sometimes!

The escapes only worth one point, I’m up by four, and with 20/20 hindsight, could have done nothing the rest of the match and still won. Instead, I panicked. I took a flailing attempt at a move I never did, ended up on my back, and thirty seconds later was watching my opponent get his arm raised.

I fucked up. I had a plan, the plan was working, something unexpected and surviveably bad happened, and I started flailing. The panic was worse than the problem. As markets get more volatile, trend down, and doom is spread, I think about this match a lot. For most startups, those who are not burning an immense amount of money to “blitz-scale” or in industries at the epicenter of the downturn, the fundamental facts on the ground have not changed. 

Even though facts stay the same, the pressure to attempt large moves ratchets up. When other competitors are visibly pivoting, doing lay offs, and making sweeping changes, it can seem like a mistake to not follow in those footsteps. The same goes in a bull market. When your competitors are paying 100k over your target salary for a role, there’s pressure to match.

This pressure causes panic, and panic causes reactionary flailing. Whether your company is bootstrapped or venture-funded, it’s your company and no one knows more about it, or has a better plan for it, than you as a founder.  “No one” includes Twitter pundits, your competitors, your investors, and your mother.

This doesn’t mean putting wax in your ears, a blindfold on, and sticking your head in the sand. Plans should always be iterated on. If fundamental facts change, plans should be blown up and rebuilt from the ground up. However, plans should not be re-adjusted in a flailing panic. The opinions and actions of others around you should be just one input, not the main driver, when it comes to adjusting strategy.  To paraphrase “If”, trust yourselves when everyone else doubts you, but make allowance for their doubting too. 

After the season ended, one of the team parents printed large foam board pictures of each wrestler and gave them out. Mine happened to be from that match, showing me in a dominant position to win, about a minute from when I panicked and lost. That picture remains where it has been since the day I got it, on the shelf of my childhood bedroom. Whenever I go visit my parents, it serves as a helpful three-by-two foot reminder. A reminder that panic, and the flailing half-hearted actions it causes, can be much much worse than the initial cause itself. As things get crazy and markets pull back, it’s something that needs to be remembered.

There's a striking range in what people think when they think “telehealth.” To many, their experience with it has been as a 1:1 replacement. They've had the same appointments with the same providers. However, instead of those being in-person, they've happened over video.

Given that, it is no surprise that telehealth visit usage numbers look the way they do. To these patients, telehealth visits quickly went from a non-option, to the only option, to a choice. Many providers now offer both in-person and virtual visit options, and will continue to do so. More choice is good for patients, but those visits remain a virtual copy of what they have traditionally been. 

Telehealth goes from good too great when it stops copying and starts stealing. Telehealth truly succeeds when it takes the good parts of provider visits, but blends them with capabilities that would be impossible without technology. For example, new care models can utilize smart device data, asynchronous communication, and automated interactive educational content (often alongside shorter provider video visits), to deliver care that goes far beyond what could be possible in-person. 

“Automated”, “interactive”, “asynchronous”, and “smart” all sound like buzzwords, but this new type of care is happening. Both startups and large incumbents are launching and scaling care models that are fundamentally different than what could be offered in-person.  The issues these new care models address (addiction, asthma, chronic pain, obesity, etc), and the type of care they provide, are all very different. However, these care models are unified by the common thread of tech-enabled recurring healthcare. Also excitingly, many of these new offerings are proactive. By more effectively addressing patient issues before they require urgent care clinics or hospitals, these models could fundamentally shift the type of care our healthcare system provides.

Before video games, there were mechanical pinball machines. You can (and people do) make video games that copy pinball machines. However, the best video games aren’t pinball machines copies, and we don’t sit here and talk about what percentage of pinball games are played mechanically versus virtually. 

The above sounds a little absurd, but that is where the telehealth discussion is right now! Telehealth replacing traditional in-person medical visits 1:1 is a tiny part of the potential benefits.  Telehealth's future should be forecasted based on the new types of care that it allows for.

That future is bright.

I’m not sure how I found Stripe (probably through a coding tutorial) but decided to use them to add subscriptions to the product. I was (to put it nicely) raw at programming, and had never built something like that. I got stuck for a few hours on adding coupon codes to the checkout. I thought I was experiencing a bug with Stripe and fired off a support email. 

Shortly after, I realized that the issue was completely on my end, fixed it, and moved on, forgetting about my support ticket. Later that day, Stripe Support followed up to confirm I had gotten it resolved, and offered to send me a free t-shirt. A shirt? For free?! Sounds tiny now, but at the time I was over the moon.

I was a high-schooler. I hadn’t taken any payments through Stripe. I didn’t even have access in Stripe to run real credit cards, and they were going to mail clothing across the country to me. Sure enough, a few weeks later the shirt (along with stickers and a handwritten card) arrived. 

Getting that shirt was one of the first times I felt like I could be a real part of the startup ecosystem. It felt like a badge of honor. I wore it in the airport the first time I went to SF. I wore it around Palo Alto the first time I went to Silicon Valley. I wore it for years and years until it gradually ended up full of holes and unwearable. It made me, an awkward teenager, feel like I belonged. 

The product I was building didn’t work out, nor did the next few, but the admiration and respect I had for Stripe never went away. Three years later, when we started Healthie, it was never in doubt what payment processor we would use. 

We’ve since processed over one hundred million in payments using Stripe, and have paid them millions in fees. Shipping that t-shirt, which probably cost them $20, ended up being a pretty decent investment.

It is (relatively) easy to provide personable support to your largest customers. It is hard to do the same for your smallest. However, those tiny customers normally appreciate it a lot more. It feels more unique and special to them, and can give you life-long advocates.