The Startup Life

It’s 9:17PM and tomorrow is my 38th birthday.

Right now — I’m reflecting over the past year and all can I say to myself is, it’s been a doozy. Calling it a doozy is a drastic understatement. It’s been a whirlwind of emotions.

This time last year I was…gimme a sec, let me check my Facebook feed since I can’t remember. (5 mins later) Oh yeah, I was at my mom’s house hanging out with my nephew. I believe I just went out with family for dinner. After you hit 30, most birthdays are pretty non-eventful.

1 Year Ago Today

Fast forward one year later and I’ve travelled to: Barcelona, Majorca, Paris, Loire Valley, Tulum, Baja Mexico, San Francisco (2x), Sonoma County, Boston (8x), New York (3x), Palm Springs (4x), Maui, San Diego, London (for 1 month). Wow — actually counting makes it seem a little nuts.

Things that have happened over the course of a year: divorced (after 5 years of marriage and 13 years together), quit a dream job, spoke about entrepreneurship to a high school, spoke also at General Assembly, competed at TechCrunch Disrupt, started my second tech company, and oh yeah — I’m dating a reality personality.

So I guess on the surface, everything looks fuckin’ fantastic right? I mean, between the traveling and the career, it looks pretty successful.

Also not peppered into there are all the movie-like surreal moments of the highs and lows of entrepreneurship, dating and traveling.

I cannot explain into words the feeling of standing in Tulum at dawn with the sand beneath your toes on a deserted beach, 80 degree water washing up to your ankles.

I cannot begin to explain the sinking heartache of returning from a business trip and finding all your furniture, everything — gone from your apartment. Someone you love dearly not willing to speak with you in person let alone over the phone.

I cannot explain the humility I find in working with kids (oh yeah — I also own a kids acting studio) or watching my nephew grow up. He himself brings me so much joy. His innocence is astoundingly powerful.

I cannot explain the taste of eating a 7 course meal in the middle of a tiny town in the Loire Valley being served to you by a 2 star Michelin chef.

I cannot describe the surreal moments shared with your twin flame on a rooftop where the silence can pierce your heart and her eyes can cut you like a knife. Or jumping a fence to watch the cityscape below while cuddled in a sleeping bag. Or spending a month living together, ordering room service, getting on each others nerves, being shuttled around by chauffeurs. Or just being able to hold each other and calm the loneliness that fills our souls.

I cannot even begin to explain the loneliness. Truth is, I think most people — 99% of people — oscillate between a normal set of highs and lows. You can stomach it. Then there are the 1% that oscillate between extremes. You hit amazing highs, but as everything must go up, it must also come down. And so you hit these amazing lows. You definitely see it in artists, creatives, innovators. I have a saying:

“Genius is only genius in hindsight. The road to genius is often viewed as crazy.”

In that craziness, you experience these surreal, movie-like moments. But then you also experience insurmountable loneliness, depression even. The more success I gain, the more lonely I feel. Yet that loneliness is also what fuels me, or so I keep telling myself.

In the end, I feel like I’ve gone too far down a road that if I do not see it all the way through, I will regret it for the rest of my life. I’ve sacrificed way too much to not see it all the way through. Problem is I don’t know if this path will yield happiness. Truly I don’t. I know at one point this is what I wanted. I know I have a vision in my head that I won’t rest until I see it come to fruition. But once that vision is realized, I honestly have no idea where I will be emotionally.

Maybe I will find something of more meaning to throw myself into. Maybe I will have a kid and throw my extreme self into being a father. I know I’ll be a great father. But I also know that I have no idea how to balance the existing activities of my life with fatherhood. And yes — tomorrow I turn 38. I see my friends, my peers — most with their families, their children and I can’t help but wonder. Did I choose the wrong path?

And then I snap out of it. Or maybe I just buckle back in. Who knows. Truth is, right now I’m living every man’s dream. But dreams are vastly different when realized. In reality, emotions, feelings, insecurities — they all come into play.

So we’ll see I guess. Tomorrow is my 38th birthday. I wonder what I’ll be saying a year from today on the eve of my 39th. I really do wonder. Things happen so fast in my world. All I know for certain is that the future is uncertain, no matter how safe anyone plays it — so why not be a little foolish.

Aug 2016 — Surfs Up in Baja, Mexico
Sep 2016 — Majorca, Spain & Loire Valley, France
Oct 2016 — Returning to an Empty Apartment
Nov 2016 — Tulum, Mexico
Dec 2016 — Christmas in Maui
May 2017 — Pitching at TechCrunch Disrupt NYC
May 2017 — Speaking at General Assembly
Jul 2017 — Coworth Park in Ascot, UK