I’m a lucky guy. There’s absolutely no denying it. As a matter of fact, I’m so lucky that I’ve suffered serious guilt about how lucky I am.
I’ve survived things that other people didn’t, I have a family that’s set me up for success, and people have given me chances in my professional life. I’ve experienced adventure that I would never be able to describe in words – from freedive spearfishing over a hundred miles offshore, to engaging in firefights outside of Baghdad, Iraq. From learning to really ride my motorcycle, to sharing some epic diving trips in remote spots with amazing friends.
There’s been no shortage of adrenaline or adventure. But it wasn’t always like this.
I bore you with an endless list of issues I’ve had, but in summary: I’ve lost brothers in battle, had romantic interests violently killed, lost family members (most painfully – my father), and endured a variety of failures both personal and professional.
Honestly I don’t do well with failure and throughout the process there have been periods of serious self-doubt that border on depression. The earth-shattering, soul-crushing kind of self doubt that makes you question every decision you’ve ever made.
Abandoning “my future.”
Early in college a friend died in a Jeep rollover and I stopped caring about college. They ended up kicking me out on academic probation – apparently final exams are meant to be attended (who knew?). That failure lead to a shitty manual labor job, living out of a shitty trailer, in a shitty town in Texas. The level of people I worked with were illegal immigrants (good people) and drug addicts (sometimes good people).
I wasn’t making any money, couldn’t afford my cell phone payments and my student loan payments were beginning to pile up.
Risking my life for a different future.
Eventually I decided to join the military, not really seeing any way out (and it meant I got that adrenaline/adventure fix). I did alright in the military and really enjoyed the camaraderie and the no-bullshit attitude. What I didn’t enjoy was the lack of real leadership (commanding isn’t leading), insistence on rules, and lack of genuinely motivated and ambitious people (nothing against any of my friends – you were the exception). Admittedly, I also have a little bit of a problem with authority.
My career essentially ended when I was offered a promotion, and they resorted to telling me I wouldn’t last “in the real world” (meaning being a private citizen). I declined the promotion. The truth is – I was starting to realize that the war my friends and I were fighting was bullshit. It was ruining our country, drastically increasing our national deficit, and ruining our credibility worldwide. And we weren’t doing any fighting that was satisfying, we essentially drove around waiting to get blown up. Not cool.
I couldn’t bear that level of sacrifice for a cause I didn’t believe in. So I left.
It wasn’t a particularly hard decision, but changing my view of the world was hard. I was coming from a war zone, where everyone was fighting everyday – thousands of miles from their family. Suddenly I was dropped back into a world full of feelings, caring about people, and sensitivity. Political correctness had run rampant and it seemed like even the most innocent jokes offended somebody. I wasn’t a saint nor soft-spoken, but everybody sure did seem overly sensitive.
Betting on me.
I quickly found out that you have to work to be awesome in the private sector – there’s serious competition (scattered amongst complete idiots). So I went back to school – easily made Dean’s list (until I got bored) and worked hard at learning (easy – I love learning). After I finally graduated I found out about Venture Capital, Startups, and Technology Companies and how they can deliver such a staggering amount of wealth to founders and investors.
One of my professors saw a little bit of promise in me and passed my name along to a neat little startup run by some truly passionate people. There I met friends that I have to this day, and there I also learned alot about how to not manage people, how to deal with difficult personalities, and the in-the-trenches truths about startup life. It was an amazing learning experience and I loved it, but couldn’t wait to get out of it.
Some time in Silicon Valley.
Stanford is expensive and really difficult. Really expensive and really difficult. I actually had to study and actually had to do homework. And sometimes, even with a bunch of work I wasn’t excelling – something I really wasn’t used to. And it turns out I really need friends and colleagues to work through difficult problems, something I was noticeably lacking at Stanford. Believe it or not, the people I was in class with weren’t on my level. They weren’t lacking in intelligence, they were all smarter than me – I’m convinced of that. They just couldn’t talk about some of the deeper things I needed – like: philosophy, the difficulties of working inside of an early stage startup, and the underlying philosophies that had defined life and death decisions (like the ones I faced in Iraq or 100 miles offshore – fighting sharks off of recently speared fish).
My classmates at Stanford were brilliant kids, with brilliant kid worries, and I was 28 wondering what I was doing there. To complicate things, the classes I was involved in were clearly taught by the B-Team. Don’t get me wrong – the professors were smart, well connected guys. But it quickly become clear that my entrepreneurship professor hadn’t ever built a company (believe it or not) and that my comp-sci teachers were overwhelmed by the amount of student requests.
It turns out that Stanford Summer Intensives aren’t my learning style. Another failure, not in grades, but in real learning.
Home, whatever that means.
So I returned home to find out that there weren’t any developers willing to leave their cushy jobs to work with me on developing the “next big thing.” And it shouldn’t have surprised me – these guys had awesome work environments already, great salaries, and challenging work ahead of them. And I was an unproven guy without easy access to capital or any real mentorship.
So I ended up taking the advice of others and took a job. It turns out I was pretty good at the job and actually had a bunch to contribute. I found that I understood and contributed to sales, sales strategy, and marketing but wasn’t a huge fan of sales as a career. More importantly, I brought an attitude of getting shit done – and it turns out that’s a really rare thing in the business world. The business world is full of meetings, and politics, and hot air. I was able to bypass most of it and operated by being friendly and nice, but frank and proactive.
The banality of home.
Boredom. The only way I could stay engaged was to push hard at my job – not sleeping much, not working out, staying plugged in all the time, and sacrificing everything but the job. If I started to enjoy any other part of my life again – I’d find that my work wasn’t important. That feeling – that what I’m working on isn’t important is something I really, really couldn’t stand. I was craving risk, adrenaline and adventure again.
So I started a company on the side, with an amazing co-founder and we decided we were going to attack the construction space. The chance of failure is remarkably high – something to the tune of 90% or more. But I’ll be goddamned if that’s going to stop me. At the time of me writing this, things are moving but we so early that any prediction would be foolish.
I had it, but it wasn’t wrapped around what I was doing in my day job. As a matter of fact, the stuff that I was working on (in my day job) was boring by any standard and was only really inspiring as it was a source of learning. But when I was offshore, sailing, diving, fishing, spearfishing, exploring – I was really in my element. If I was waiting on a monster wahoo to come in, or fighting off a shark, I was having the time of my life.
And even though I craved adventure, I wasn’t prepared to make the monetary/professional sacrifice to move to something I enjoyed more.
I got a call from my sister, who was working in the Congo. I had a habit of answering like a complete jackass, we had a great relationship – we laughed alot and had so much fun that we were actually pretty embarrassing to be around. This one was different though, she was serious and tense – I picked up on it immediately. Something was really, really wrong. The good news is that she wasn’t crying – so she was relatively composed and her life wasn’t in immediate jeopardy.
I’d prepared for this a million times over, she was in a sketchy situation and I was ready to drop everything, empty a couple of bank accounts, and go over there with the express intent of buying a couple of weapons and finding my sister. I could operate with the best of them and I really didn’t give a shit – it was a lawless place, the kind I liked… But that wasn’t it at all.
My Mom had a heart attack. She was visiting my sister in the Congo when it happened. Immediate grief and a sudden sinking feeling.
I’d already lost my Dad to work, stress, and a generally unhealthy lifestyle. I couldn’t lose another parent that way. The night I received the call, I couldn’t sleep. I couldn’t do anything. Completely helpless, I decided I wasn’t going to let work, other people’s opinions, my projects, my desire for wealth, or anything else stand in my way. I was leaving to go sail and live a pure, simple life and I was taking my Mom with me.
So here I am, ready and (for the first time) willing to give up money and work to practice what I’m going to preach to my Mom – the value of time, following your passions, and experimenting with better ways to live.
If you’ve made it this far, I really appreciate your attention. I hope there was some value in the preceding words, that you’ll subscribe as I share my experience preparing for this transformation, and that you’ll stay with me as I continue to move forward.
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