Cockroach Companies

Healthie moved offices this week, to the largest space we’ve had since we became remote-first during COVID. It’s a WeWork office with plenty of space, natural light, and most importantly, no cockroaches.

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.”


My 2022 Book List: What I read in 2022, and what I liked the most.

After years of barely reading books, I started again in earnest in 2019, and have read a lot of them in the years since. Even with all the great blog content, tweets, and journalism, I still get a ton out of reading actual books. The biggest thing I did to read more was to switch to e-books (I use a physical Kindle, and the Kindle app on my phone). I find it much easier to read a lot if I can very quickly get through a few pages throughout my day. Being able to buy the next book instantly also helps me keep up the momentum.

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

Grateful – TAVR, Health Issues, and Reflecting on the Past Ten Years

Assuming everything goes smoothly, this scheduled post should be going out around the time I’m getting out of an operating room. 2022 has been a year of ups, downs, and severe aortic stenosis, and I’m excited to get a TAVR procedure done. A TAVR is a minimally invasive way to replace my failing aortic valve, which should restore my normal heart function and let me get back to having an unrestricted day-to-day life for the next few years.

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!

Our React Native Experience

Ben Sandofsky, an iOS developer I have immense respect for, recently tweeted about why React Native is “stuck at its niche 2.6% adoption.” His negative opinion got a lot of traction, so I wanted to share our experience at Healthie.

In 2018, we rebuilt our native iOS and Android apps (which used Swift and Java respectively) in React Native. It was one of the best engineering decisions we’ve made. Here’s why

1) Given our size at the time, it did not make sense for us to have more than one iOS or Android developer. This meant those devs were working in isolation. React Native let us set up a (mostly) shared codebase with multiple people working on it.
2) It allowed our web engineers to understand and give feedback on the mobile app code. We use React for our web front-end, and once we switched, our web devs were able to help mobile out with code reviews and trouble shooting.
3) While you definitely can’t just re-use web React code in React Native, we were able to share libraries and parts of code between our web and mobile applications.
4) 90%+ of the code can be shared between iOS and Android. No more separate git repos per mobile platform.
5) Code push. At the time, we sometimes had to iterate quickly on the mobile app. Code push allowed us to quickly release hot-fixes and improvements without always needing to go through the (at the time slower) App Store review process.
As Ben mentions, 1-5 could all be accomplished via web views, so why not just use that? 95% of our mobile app lends well to React Native. However, parts of our app (Apple Health syncing, video chat, etc), needed to be done in native code. React Native makes it easy to bridge out to native where needed. In addition, there are existing open source libraries for some of those bridges. This is a huge advantage versus a web view approach.
React Native is definitely not right for every type of app or team, but has been a great fit for us given our needs. I don’t think it makes sense to dismiss it out of hand.


Wrestling state finals, senior year of high school. I’m cruising through the match, up 5-0 over someone I had already pinned twice that year. I tilt my opponent onto his back as the ref’s hand hovers over the mat, waiting to call the pin. I’m an inch away from being a state champ. Six years of hard work are about to pay off, and then, my opponent escapes and we’re back on our feet.

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.


What’s Next For Telehealth

It’s been an eventful past few years for Telehealth (to put it lightly). Telehealth usage started at less than 1% of outpatient visits pre-COVID, shot up to 13% percent in the first six months of the pandemic, and has since fallen back down to ~8%. With both COVID and telehealth usage numbers flattening, there has been a lot of conversation about the future and direction of telehealth moving forward. So what comes next?

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.


Stripe turns 10 today, so I figured I’d share my favorite personal Stripe story. It’s an experience that greatly impacted how I think about customer service (and growth) at Healthie. It was Jan 2013. I had recently turned 16, and was building my first product that I wanted to charge people for.

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.

Surgery and Startups

When I had my second open heart surgery in March 2017, the thing I worried about most wasn’t the getting anesthetized and cracked open during the surgery itself, or the mortality risk, or the uncertain recovery. it was the impact that being unreachable for a couple days would have on my startup.

In the lead up to my surgery, Healthie was a year old. We’d raised a million dollars just a few months prior. When you raise, you paint a vision for investors, full of billion-dollar liquidity events and company immortality. You paint a picture of being able to predict and control the future. Going under for surgery is the opposite of all of that. You are giving up all control (and consciousness). You are placing your life and future in the hands of a surgeon you’ve met a couple times and in a care team who are complete and total strangers. It sucks.

It was hard for me to tell my cofounder about it. It was mortifying for me to go from raising money, to our next monthly board meeting, where I felt obligated to tell our new board member (and also lead investor) about my newly scheduled surgery.

I was worried that they’d think I wasn’t pulling my weight, that I wouldn’t deliver on my promises due to a medical event I had no control over. I was concerned about how all my recent direct hires, who I pushed to bring on, and had agreed to manage and lead, would do in my absence. I thought I’d be letting all our customers down, especially the many who I had gotten on sales or success calls with and promised that I’d be there to offer personal support.

In all these cases, I’d stammer out a poor explanation about having a problem with my aortic valve, and that I’d need to be out a few days for a surgery. I’d prep myself for the worst responses, and get nothing but understanding and positive reactions. It wasn’t even accommodating or sympathetic (which I appreciated), just people being supportive and treating it as a non-issue.

I was knocked out for the surgery itself, and the immediate recovery is full of blurry memories and dialudid. A day later, after recovering enough, I felt unnecessarily compelled to hop back on email and support tickets from my phone in my hospital bed. This was a bad idea.

A couple of days later doing that, my recovery was progressing well and I was hours from being released. I got an automated email alert that we were having web application availability problems. My blood pressure spiked so much that an alarm went off, and a nurse came rushing in.

The alert ended up being a non-issue, and my blood pressure went back to normal. However the blood pressure spike (despite my explanation) greatly worried my care team, and I came close to not being released from the hospital that day.

In hindsight, I took one of the worst things ever to happen to me, and made it worse. Despite my worries about having surgery, our customers didn’t mind, my cofounder didn’t mind, our investors didn’t mind, and our team performed admirably in my absence. I took a shitty, scary time and made it shittier and scarier.

It’s common to talk about a reality distortion field that comes from a startup’s founders. However, I’ve never seen anyone taking about that field distorting things in reverse. As a founder, you’re supposed to live and breath what your company does. That attachment makes it very easy for founders to overemphasize and fixate on molehills, which quickly turn into personal mountains, and in many cases (including mine), actual quantifiable health issues.

In hindsight, my reaction was incredibly irrational. However, as a founder, it’s normal to seem irrational. The ability to have strongly differing opinions is what allows founders to build big, novel companies. Unfortunately, that same personal conviction can cause trouble.  I know it did for me in this case.

If you’re a founder beating yourself up about personal events that are outside your control, take a deep breath. What’s inflicting more damage to your company? Those events? Or your reaction to them?


For the first time in over a year, I’m resting my elbows on the carved wooden bar at the hole in the wall, only in NYC dive bar underneath our (now former) office.

Undercover cops shot a black security guard on the doorstep in 2000, after the security guard refused to sell them pot. The Grand Jury declined to indict them. Anthony Bourdain,  the Hunter Thompson of our time, drank here. 30,000 New Yorkers have died of COVID since I’ve last sat at this bar.

This bar has five different names — on the sign, on google, inside, etc, including one calling it a “distinguished cocktail lounge.” I recommend buying only bottled beer and paying only in cash.

This bar is a survivor, between a LensCrafters and a Dos Toros. It’s one of three businesses on this block older than 10 years, the others being a hardware store, and a sex shop that has a sign proclaiming its “busines hours.” (sic)

This bar is a survivor, but in between the (mostly) socially distanced bar seats, are ghosts. Of Bourdain, of Patrick Dorismond, the father of two murdered by undercover, unidentified cops, of the 30,000+ New Yorkers killed by “just the flu.”

Much like scars, the ghosts never go away, but they make us who we are as a city. On dark, rainy nights like this, where we can uneasily re-experience something we took for granted for so long, I remember them.

Survival Bias in Startup Advice

Lots of startup advice is told like a war story. Founders of (now) successful, thriving companies talk about the dark days, full of all nighters, personal debt, stalled growth, and low runway.

These war stories generally include advice like “never quit” and “keep on pushing.” The storytellers talk about taking huge personal risks, working themselves to the bone, and approaching their mental breaking point.

These stories all have the same ending. The efforts paid off, the company turned around, and the founders did (more than) well. They look at these dark days almost nostalgically, and talk about how they overcame them on Twitter or over drinks.

These stories all have happy endings because the companies (and their founders) survived. Very few people look to advice and stories from unsuccessful founders of failed companies.

Companies that ultimately fail have plenty of dark days as well. Their founders, in many cases, work just as hard and take on just as much personal risk as founders of companies that work out. However, their stories end in a range of begrudging acceptance to soul-crushing sadness. It’s not pretty.

3 years ago, in April 2018, we went through one of our darkest days at Healthie. Our sales and marketing strategy was not working, and we had to lay off 20 people (85% of the company) in a single day. What followed was three months of little sleep and crunching the team, trying to rebuild our product from basically the ground up. It was an absolutely miserable time, but ended up turning our company around, and put us on a sustainable path to fast growth, profitability, and success.

We survived those dark days, but a lot of companies don’t. There were times where it looked like we wouldn’t, and I still have mixed feelings about how close myself and other employees came to burning out. Our decisions were the right ones, but I definitely made them with a great deal of naive optimism.

If you’re struggling and thinking about the best path forward, it’s important to be mindful of survivorship bias in startup advice. Before taking on immense risk and emotional burden, get a clearer picture of your expected outcome, not just stories told through rose-tinted glasses.