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 ….

Once thought to be an arcane pastime for the socially awkward, coding is growing in popularity- among professionals, hobbyists, and increasingly, among educators. Teachers and educational professionals now posit that it’s essential to teach kids about algorithms, programming, and the big boss of all successful human endeavors: logical, sequential thinking. Furthermore, teachers and parents say that girls in particular need to be encouraged and included in STEM fields, where they often face systemic bias.

I’ve been teaching my 6-year-old daughter about coding for a while now, and it’s been super rewarding. Learning to code may not be immediately appealing to kids - it wasn’t to Olivia - but after getting past the feeling that it was uninteresting and/or “work,” she has warmed up to it. Both of us are learning a lot. Of course, at the age of six, she’s not writing “real” code, but rather doing activities that simulate coding.

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I would’ve never imagined that dreaded obligatory rituals and traditions from childhood would become self chosen regular practices in my adulthood. High holiday prayers set me up for meditating and the annual Yom Kippur, or “Day of Atonement,” would be my first introduction into fasting. In Judaism, during the most holy day of the year we ask God for forgiveness and as a way of repenting for our sins, we abstain from food for an entire day. Needless to say, I really did not look forward to the day of “no eating” growing up. I now welcome regular fasting into my life, albeit the reason has nothing to do with soul cleansing or repentance. The day I struggled with for almost four decades of my life has now become something I do regularly with eagerness for the breaks it gives my body and mind from eating or even thinking about food. My fasting practices have evolved over the last couple of years depending on current routines or personal goals and can range from intermittent fasting to water fasts, all for different periods of time. Let me dive into some of their awesome benefits, the drastic ways it has changed my health, and the different types of fasting out there.

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"It’s not whether you win or lose, it's how you play the game" is one of those quintessential expressions we grow up being taught to live our life by from a young age. And that’s true for Little League and most amateur sports, which is in fact who the sports poet Grantland Ricef was addressing when he wrote what would become one of the most famous aphorisms of all time. In all aspects of competition “how you play the game,” should of course always be conducted with good ethics and morals, honor, and integrity. Sportsmanship aside though, winning matters. As you get older and graduate from the minors to big league, winning becomes essential with real situations in your life and career. With big wins you can take care for your family, rise the ranks at work, or accelerate your own company to new heights. Contrary to popular belief however, competition does not mean there is only one winner. Often in business competition is desirable and necessary to drive growth so that everyone wins.

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My struggle with intense back pain led me through a variety of different therapies, some that worked better than others, but all worth sharing with the hope that one may help you too.

Back pain is one of those ailments that unless you experience it yourself, you don’t fully understand how debilitating it is and how much it permeates throughout your daily routine. It quite literally affects your entire life not to mention your mood (constantly being in pain can lead to constantly being pissed off). You’ve heard of ‘hangry’ - the mood you get when you haven’t eaten in a long time? Someone needs to come up with a term for those of us with back pain. It makes ‘hangry’ look like a trip to Disney World. Some people have back pain and it goes away over time. Some people have it and it never goes away; it’s a constant part of their life that they just have to cope with and manage. I don’t yet know which category I'll fall into but it's been ever present for several years now.

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From Animal Flow to the GNC InBody Machine - There’s no boundary I won’t cross

Last week I shared with you the diet that helped optimize my body, energy levels and blood work. Much in the same way people ask me what I eat, I get a lot of questions about my fitness routine. And while I post a lot of stories on Instagram about my peculiar “animal flow” workouts, that’s actually only half my formula.

I’ve always generally been what would be considered “in shape.” I was on the track team in high school. I played sports. I exercised (somewhat) regularly. As fitness culture evolved, so had my repertoire with the likes of Barry's Bootcamp, boxing, pilates, yoga (in all its various forms and temperatures) and other types of classes at least once a week. Cardio was a constant thrown into that mix.

Usually when doing cardio I’d go super intense because I was under the impression that I’d get the best results by dedicating an hour to accelerated running or sprinting intervals. I thought that would get me the physique I wanted and burn calories to lose fat quickly. I was wrong. It definitely got me a great sweat but it didn’t transform my body.

Finally after years of trial and error, I completely transformed my body with one pivotally crucial workout: weight training. Compared to cardio alone or cardio with a mix of “body weight only” activities, weight lifting is far more effective. And while pushups, situps, and lunges are great, if you aren’t using actual weights with those movements, your muscles and overall physique simply aren’t pushed into true transformation. Granted a few years ago I was doing lunges with a ‘spare tire’ around my waist but that’s not the kind of extra mass I’m talking about here!

If you follow me on Instagram, you’ve likely seen some of my out-of-the-box fitness practices (Animal Flow) and over-the-top nutrition habits (green juicing & tons of carbs?!). I practice a way of life that incorporates and prioritizes healthy living into every aspect of my daily routine. But I wasn’t always like this. I didn’t always feel or look healthy; nor did I pay attention to what went into my body (tons of processed junk) and the havoc it was doing to my body.

Everyone I know commits to 30-minute workouts at least a few times a week. We live in a newly health-obsessed culture, and perhaps besides LA, nowhere is that more obvious than here in Miami. But I don’t know many people who take a daily 30 minutes to plan or prep their meals. In fact, NOT planning your meals after a solid workout is like getting a car wash on a day you know it’s going to rain. You simply aren’t reaping the full benefits of your actions. I’ve learned over and over again, that no matter how rigorous my exercise, without the right diet I wont see good health or fitness results. On any given day, presented with the choice to workout vs stick to my healthy food, hands down I skip the workout and choose to feed my body right. Obviously if you can do both the results and gains are optimal!

The experience of building JoonBug from the ground up during my days as a nightlife impresario and before the days of EventBrite and social media provided valuable tools and lessons that have come in handy in all areas of my life.

It’s not that some of the best ideas don’t happen over a few drinks at 2am. Sometimes they do. But what’s unique is the experiences that happen in the places and with the people that associate with the 2am timeframe that produce the best ideas. Nightlife (a place shrouded in mystery) often propels some of the more interesting characters in entrepreneurship into not only stardom but great wealth. Though it’s not necessarily nightlife where that stardom and wealth happens; Sometimes nightlife is just the stepping stone. For me many of my greatest life and business lessons spawned from my experiences in nightlife.

Let’s go back to just around September 11, 2001; a time when many New Yorkers and Americans were not only recovering from a national tragedy, but where businesses and workers were also struggling. The tech bubble had burst and I was out of work after a failed tech startup I had founded went bust.

As sunny South Florida continues to develop into a world-class locale, and a legal tax haven, many New Yorkers are reconsidering whether the city that never sleeps is the right place in which to live and park their assets. But few know how challenging the process can be for those within a certain tax bracket… Lucky for you, I have the scoop.

I’m a New Yorker through and through – born in Brooklyn, an NYU grad, and job-creator for hundreds of locals through three different companies I founded in the city. More than 35 years later, however, I realized that perhaps the concrete jungle wasn’t the best place in which to take the next step in my career, and continue to grow my net worth. The tax burden, and exorbitant costs that come with living in one of the world’s greatest cities are steep. This is common knowledge. A lesser-known fact, however, is that it’s a massive headache to relocate from New York to a new state once you reach a certain rung on the financial food chain. The state of New York doesn’t let its prized residents flee so easily, a fact that is especially salient today as prominent figures and institutions – Icahn Enterprises, U.S. President and Queens native Donald J. Trump – are stealing headlines for relocating to Florida, just as I did in 2014.

My move was prompted by the same factor that promoted Carl Icahn and Trump’s – the math simply was no longer working out. The family I had always wanted had materialized, and as my wife and I began researching elite schools for our daughter, which were practically the same cost as a state University, the siren song of sunny South Florida began calling me. We knew we wanted a bigger family, and the financials were not making sense. While I’ve never looked back on the decision to relocate, I urge anyone considering following in my footsteps to educate themselves on what the process will entail and be both mentally and financially prepared.