If you looked at my investment history with no context, you'd think I have the attention span of a golden retriever at a tennis ball factory. Impossible Foods. Athletic Greens. SandboxAQ. Cirkul (the flavored water bottle that Gen Z can't put down). Flexport. Canyon Bikes. Kraken. A real estate portfolio spanning Santa Monica to Brooklyn. And yes, infant nutrition. 

But here's what I've learned after building two companies, exiting both, writing a book, and deploying capital across more than fifty startups: every single investment decision I make runs through the same pattern recognition engine. And that engine was built, improbably and irreversibly, in the New York City nightlife scene of the late 1990s and early 2000s.

Let me tell you what I mean.

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On New Year’s Eve 1990, I was 14 years old, standing outside a club in Manhattan with a VIP ticket in my hand that might as well have said “this kid does not belong here.” My black-on-black outfit was carefully calculated, sleeves rolled to just the right fold, and my suede Dr. Martens had seen maybe one other party: my friend’s bar mitzvah. I was freezing, faking, and fully convinced that if I didn’t get into that club, my life would be over.

That night, I got in. Barely. And that moment — that freezing, awkward, exhilarating, low-key fraudulent moment — is when I learned something I’ve carried through every business I’ve built and every founder I’ve backed:

Success is just getting past velvet ropes over and over again.

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It was the summer after my sophomore year at New York University College of Arts and Sciences. The year was 1997, and I was looking for something to do over the summer. But it had to be something good–something that would make me stand out later on when I started applying for medical school. Back then, my entire life revolved around my goal to get into a top medical school, so everything I did was geared toward achieving that goal.

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For every successful business I’ve started, or investment I’ve made, there have been multiple failures: businesses that never took off, investments that went to zero, and times when I was super gung-ho about something, only to have it end up in my Bad Idea Hall of Fame. Want to know more? Let’s take an honest trip down memory lane.

The Kickoff

The first one that comes to mind takes me back to my college years, when I was about 20. I was still in school at the time, and really into kickboxing, which was just becoming popular, with studios popping up everywhere. One day, I had a lightbulb moment for how I could monetize the kickboxing trend.  

I bought the domain name Kickboxing.net with the plan of building an online directory of kickboxing studios. To fill out the front end of the site, I put up a bunch of content around the sport, but that was the easy part. The more labor-intensive work was creating the software that would pull information from a database about different locations. During my limited free time, I programmed the whole thing, spending probably about four months on it. 

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Building JoonBug was a fascinating, engrossing experience, and there were all kinds of moving parts, from the tech side, to the finance side, to the social and entertainment aspects of working in nightlife. And peppered throughout those experiences were, of course, celebrity encounters! My team and I met and mingled with some of the true glitterati of that time, many of whom are still famous today. It was almost always a transient, happenstance kind of thing, a fun or exciting or just plain weird moment in time. These are just a few that stand out in my memory.

Biggest Fan

During my college years, but technically before JoonBug, I often went to a lounge called Spy Bar and tried to get in. It was the hotspot, the hardest place to get into, and the best place to be seen. I had a few hits, but mostly misses, trying to get past the velvet ropes. Spy Bar was a celebrity hotspot, so “ordinary” people had a tougher time getting in than they might have at a large mega club, where doormen were looking to pack the giant venue out with an eclectic crowd.

The story of the first (and only) time I ever smoked pot.

Designated Driver

All through my high school years, I had avoided ever doing drugs of any kind. Maybe I drank a little here or there, but never drugs—basically because my parents scared the crap out of me with horror stories of people who did drugs and became homeless, or got addicted, or went crazy, or just straight up died. 

For better or for worse, this approach worked for me, and I never felt the desire to go out on a limb and smoke pot with my friends (that was about the hardest stuff any of them did). I was the reliable designated driver type: clean, sober, and happy to keep it that way.

A lot of people ask me why I wrote my first business book, NightLife Lessons. The answer is simple: it was mostly a bucket list item for me, and not about making money. Sure, I wanted to help myself by looking back and writing down what I’ve learned over the years, in the hopes of helping other startup entrepreneurs on their journeys. But for the most part, I just wanted to see if I could write a book…and then hold it in my hands.  Below, I'll share a bit about the process of writing my book and what it was like for me.

Telling Stories 

I’ve been funding and advising startup founders and entrepreneurs for almost a decade now. As part of that role, I often find myself telling stories from my own experiences building startups, to help founders not only deal with their current struggles, but also avoid pitfalls that might lie ahead of them. 

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Playing to Win in the Game of Love

At the age of thirty, I was starting over in the dating world, and looking for the total package: someone smart, pretty, easy to be around, and definitely someone with whom I would have great chemistry. That’s a tall order, even under the best circumstances. But when you’re running two companies, and have next to no free time? Practically impossible! So I decided it was time to use my aptitude for innovation on a totally new subject: myself.

A Year of Insanity

By the time I hit my early 30’s, I had been living in New York City for my entire life. The years had been full of highs and lows, both personal and in business. There was my father’s passing, when I was only a kid. My mom’s struggle with chronic health conditions and building a business to support us. The typical ups and downs of middle school and high school. Falling in love with nightlife at the very young age of 14, and staying in love with it through high school, college, and beyond. Working like crazy to get into med school, only to realize that it wasn’t for me, and dropping out to join the dot com boom (and bust). And of course, the all-consuming task of building Joonbug into a juggernaut that effectively brought the nightlife industry into the digital age.

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What makes an investment promising, from the perspective of a venture capitalist? As any VC will tell you, it's not so much the idea being invested in; rather, it’s the team behind the idea, and most specifically, the founder.

A Smart Bet

VC investment is very much like gambling. Even having the best team and idea does not guarantee any level of success. That’s why many VCs spread their bets across a number of different companies; the way the math works out, you only need one outsized win to more than make up for all of your losses (or mediocre wins). But how do you optimize your chances of getting that outsized win? How do you know what to look for in a startup?

Well, there are many immeasurable factors that go into the success of a company, and to be honest, luck is probably one of the most important. Other factors, however, are much more concrete. And over the years, I’ve found that finding businesses with great founders significantly increases my odds of success.

Whether it’s a daily fitness log, an all-purpose bullet journal, or a traditional “Dear Diary,” there’s no doubt that journaling is a fashionable habit these days.

Personally, I started journaling in 2013, having read about it on a self-help blog that I can’t now recall (maybe Tim Ferris?) and I haven’t missed a day since then.

When I tell my friends and colleagues about my journaling habit, they usually ask what the point is. Did I want to meet some goal, achieve some benefit, hit some benchmark? Ironically, I didn’t start journaling as a means to any kind of end - I just wanted to see where it would take me.

There are a lot of different approaches to journaling, and different things work well for different people. Over time, I’ve found a method that works perfectly for me. Here’s what I do.

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You’re more likely to be struck by lightning. You’re more likely to be eaten by sharks. You’re more likely to score a royal flush in your first hand of poker. And on and on it goes. Basically, it’s scientifically proven that playing the lottery is a waste of money. So... why do it?

Every week, I play the lottery, and I have for years. I don’t plan on breaking this habit, either, even though I know that it’s essentially statistically impossible for me to win, and so the $2 I spend is a loss from the get-go. I’ve gotten some strange looks from friends and others when they find out I play or notice the tickets in my wallet. People are often surprised, and in some cases, disapproving-- playing the lottery has something of a taboo about it!

But for me, it’s not about the odds that I might not win-- it’s about the fact that I definitely can’t win if I don’t play. Let me explain ….