Living on the Edge

Living on the Edge

Through some amazing self discovery, adventures and interesting life and business experiences, one thing has become abundantly clear to me: I thrive in uncertainty.

I am at my best, produce my best work and generally just enjoy life more when there are massive amounts of uncertainty. Problems, obstacles, roadblocks, chaos -- bring it on.

I'm not sure exactly when I developed my love for the unknown, but there is no question that it is where I am most comfortable. I'm certain that I wasn't born with this, but it's more of a muscle that developed over time. It requires complete confidence in your own abilities and an unwavering belief that you will always figure out a way. That happens over time.


I've unintentionally gone out of my way over the last decade to put myself in ridiculous situations and environments exploding with uncertainty. Maybe I was trying to test myself. Maybe I was trying to grow that muscle. Really though, it's where I'm most comfortable so it's obvious why I gravitated towards these situations.

Here's a small sampling of my life of uncertainty:

  • Walking away from a comfortable six-figure job at an international bank with barely a plan for what was next
  • Starting a tech event with no prior event experience and promising hundreds of startups and thousands of attendees would show up
  • Moving to Boulder, Colorado as a contractor for an unfunded tech startup and living in a 3 bedroom house with 5 guys
  • Starting up a web development shop when I barely knew how to code or find projects to pay us
  • Running said web development company into the ground and not being able to band together a group of talented folks (I'm still haunted by how I handled it to this day)
  • Starting a second web development company immediately after the collapse of the first one
  • Getting rejected from a handful I jobs, incubators, accelerators and startups I was in no way qualified for
  • Burning through my entire savings and retirement accounts several times -- ugh!
  • Living in random Airbnb apartments in NYC for an entire summer
  • Traveling to Brazil for 3 weeks during the World Cup without booking a place to stay until I landed in Rio and not knowing one word of Portuguese
  • Teaching myself sales, marketing, product management, UI and UX design, how to start businesses, management, leadership and dozens of other skills that had to be learned on the fly

Just reading this list would be enough to completely stress people out. I stopped worrying my mother with all these uncertain adventures after I left my corporate job. That was about all she could handle, but that was just the beginning for me.


I've been blessed with this ability to be impervious to stress. I don't know if I'm lacking some critical part of my brain or if it's totally psychological, but I don't feel stress. Even when I was laying in a bed in Las Vegas with the world crumbing around me, I didn't feel an ounce of stress. It was one of the lowest points in my life, and I felt excited. Disappointed, but excited for the good things to come.

Today, just as every day for years, I continue to seek out the situations of great uncertainty. It brings out the best of me and that's what really matters at the end of the day.


I'm working on a new side project now that has completely absorbed all of my attention, and yet almost all of the world would think I'm totally nuts. Good. I like it that way. Sometimes, I take a step back and think I'm totally nuts. I just accept that as part of the process and then keep going.

This new side project provides me with all of the uncertainty I need and allows me to do what I do best: live on the edge.

Maseratis and North Stars

Maseratis and North Stars

Product of the Product

Product of the Product