I quit high school within a month of my first day as a freshman. I still attended, but participated at absolutely the most minimal level. My grades reflected this participation. High school wasn’t rewarding to me, and every day felt like I was unemotionally going through the movements of being a teenager. In the evenings I worked a job at my fathers print shop. During the nights I learned to program because I had vague ideas for social networking software, and the programming was engrossing to me. Everything outside of school was more engaging than school itself. Two years was enough. I went to the first day of Junior year and dropped out the second. On to the next thing.

After high school I worked full time at my fathers print shop. On nights and weekends I continued to learn programming. We didn’t have good internet in rural Montana, but the meager connection we had, combined with my budget for technical books helped me build enough confidence to call myself respectable web application developer (I wasn’t, at the time). The engineering was fascinating to me, but learning it was also a way for me to stretch my social muscles. I utilized many forums and message boards to find answers to my questions, which led to me joining these communities. Online, I met people with similar interests who didn’t judge me. I liked being friends with these anonymous online personalities. Despite not attending high school, this probably set me out on a better path than otherwise possible. This doesn’t reflect the expectations of someone learning about themselves on the internet. Typically stories of online communities are filled with accounts of toxic humans lashing out from behind anonymity, but at the time I really didn’t notice, but mainly, I think I just got lucky.

While I worked full time and learned to program, I still maintained relationships with a few friends who I did meet in high school. Mostly we just hung out after work/school and smoked pot around a camp fire. I don’t talk to them much any more, but those guys had a pivotal impact on my life. Two of them, in particular, had a school teacher whose creative writing class occasionally assigned them film-making projects. After seeing their first project, a silly mockery of the then-popular cop drama “Crime Scene Investigations,” I was instantly motivated to do something more than anything in my entire life. Together and with the help of some other friends, we made video after video of primarily teenage-level shtick. There were cooking shows, video game reviews, sketch comedy, and we had ambitions of much more. Creatively this is the most developmental period of my entire life.

I decided to go to college. Film making, I decided, was what I wanted to do full time. I never even considered college for computer science, as it just seemed like more protocol, like the school I had dropped out of a year prior. Film schools all promised a more career-driven pragmatic approach: teach the skills and let you do what you want with them. The downside, however, is that film schools are extremely expensive, selective, and many were in places I didn’t much care for: LA, NYC, etc. I stumbled upon Academy of Arts, a for-profit university in San Francisco, with a campus spread throughout the city. Their only entry requirement: a GED and someone to sign on your student loans. I got both. I toured the school and that fall I moved to San Francisco.

My first semester in San Francisco was pure shock. As a seventeen-year-old who had never spent any time outside of Montana, San Francisco was a whirlwind. It didn’t feel like it as the time. I felt like any other 17 year old: invincible, but in retrospect it was an abrupt life changing few months. After the 1st semester I moved into an apartment to save on housing costs, and one of my friends moved from Montana, partly to escape, and partly to be roommates with me and help make films. He went through a similar shock, but we made it work for about a year.

Film school at AAU wasn’t at all what it was sold to me as. AAU is a for-profit machine. It’s a party school for the extremely wealthy with small disbursed cells of serious students. Fortunately, I found them, and a small group of people in my class became friends and started making movies together. With one of my roommates as the writer, and the other as the cinematographer, I was again a film maker. We started getting more serious about our movies, with writing, casting, schedules, sets, lighting, permits, film festivals… the list goes on. We were on the onramp to becoming professional film makers.

Problematically, however, was the environment in which this all started to take place. The school which provided the catalyst for us all to meet and combine our motivation didn’t provide a good framework for growth. Instead, it bogged my spirit down with a myriad of requirements and restrictions. Some of the best work that came out of that school got some of the worst grades for not following the rules. Film school became emotionally disengaging because it seemed the harder I tried the worse I did, and again it seemed like I was just going through motions to please the system in which I didn’t fit.

Two years into my film school experience I dropped out with $55,400 in student debt, owed entirely to various federal student loan programs.

I got lucky. In 2006 when I decided San Francisco was where I was headed, I had no idea it was the tech hub of the world. Within 3 months of dropping out, which I bridged with a job at FedEx, I found a programming gig paying $15/hr. It was a startup with a 2-letter-dot-com that was working on being a competitor to Skype. The founders worked out of a beautiful house in Bernal Heights. Again, I was entrenched in a new and engaging obsession, that actually made me enough money to live off of. It was fascinating and I worked with people who valued my skills and respected me as an adult.

It was at that job that I met a one of their consultants, whom I’m gratified to be able to call my colleague to this day. He was extremely encouraging, and told me I was one of the smartest people he’d ever met, and while I still don’t believe that, it came from someone I respected. When he asked how much I was making, he scoffed and told me he could pay me double out of his pocket if I wanted to do some consulting with him.

We worked on contracts and a few iPhone apps for several years out of our office in Palo Alto. It sat atop a charming art studio which is now under earthquake safety renovations, and the office has been removed. During this time I’d been honing, and broadening, my skills and gaining a reputation for both design and the speed at which I could implement entire iPhone applications.

One and a half years later, I had an idea for an app. It would capture bursts of pictures and play them back as an infinite stop motion movie. One of our clients we hung out with on occasion was an entrepreneur and somewhat connected in Silicon Valley. I took the idea to him and within 2 months I was working full time on my idea, designing and coding. Together we continued evolving the idea. Within a year we raised a seed round to launch. The app gained a social aspect, where your friends and family could add to your infinite movie. My app idea became a company known as Ficture.

Ficture was a beautiful product, and is to this day my biggest achievement. I used the product to bridge the distance between my family in Montana and my life in San Francisco. It combined art and technology. Its usage gave an emotional connection far greater than any social media app at the time. Social media properties like Facebook and Instagram serve only to provide snippets of the most finely curated moments of a persons life between highly targeted advertising. Ficture gave context and humanity to your moments by providing a safe space to communicate. It wasn’t just another channel to broadcast.

Unfortunately it was too much, too soon, and with the wrong group of people. For all of Ficture’s momentum, it failed to deliver any potential of ROI for our investors. Management attempted to pivot and grow in the direction that made ROI a possibility (an acquisition), but it never happened. My inexperience in management left me unequipped to deal with the changes and unable to influence the direction of the company culture and product. I left the company in early 2012. It was the hardest decision I’ve made in my entire life, but it was time to move on.

I picked up consulting again as a way to make a living, this time efficiently designing and developing prototype after prototype of other peoples dreams. I was unentusiastic about the work, but it paid the bills, kept a roof over my head, and provided me with some free time to recuperate and come up with my next thing. During this time a colleague from Ficture was starting a company called Making Friends to build software for the Autism space. He invited me in as co-founder and CTO, my former title at Ficture. Working on problems in the Autism space gave me something that I had been looking for, post-Ficture: it had a potentially positive societal impact. I decided I’d help on this project part time and fund the company with money I was making consulting.

While consulting and moonlighting as a CTO, an acquaintance from a former contract reached out to see if I was available to work on a large project he had been brought into. It was an Angies list-competitor for a wealthy entrepreneur out of Palo Alto. I formed an LLC and hired on a staff of 3 and we worked full time for 5 months to bring this idea to life. I continued to re-invest the money made from this contract into Making Friends.

In early 2014 the Palo Alto entrepreneur disputed his final two bills totaling over $98,500, which primarily belonged to the staff I hired to build his product. It would take me 2 years and over $15,000 in legal costs to recover only $18,000 of that final bill, which was entirely consumed by one of my staff which had sued me for non-payment. Fortunately the other two subcontractors didn’t come after me. I no longer had money for Making Friends and the 2013 tax bill had come due. I did not save enough to pay the taxes without this final payment from the Palo Alto entrepreneur. Two years later I’d finally settle with the IRS and reach a final tax bill of $54,800. I now owed the US government over $110,000.

I moved to Denver, Colorado. It was time to get out of San Francisco, time to downsize. Denver and its mountains are beautiful. I was able to afford a decent house with a yard, for the first time in 8 years. I got a dog. I continued to work on Making Friends while consulting to pay the bills. The momentum on Making Friends eventually dried up and we failed to attract the interest of any investors. I invested over $60,000 in Making Friends. I continued consulting.

One of my friends in Denver, and myself, started a YouTube channel to teach people how to build computers. We used money from consulting to afford some camera equipment and set peaces. This project combined two of my favorite things: computers and film making. I set up a studio in my basement using random parts from Home Depot. We made around 6 videos but momentum on the project dried up. I didn’t have the motivation or money to continue working on it myself, so the project was abandoned.

I kept up my with my friends in San Francisco. My former colleague, now best friend, from my first ever tech job was starting a new company focused on the Bitcoin space. He wanted to revolutionize the world with this new crypto-currency, which promised it couldn’t be censored, and would be a decentralized protocol similar to the internet. It caught my interest in a big way. I had been aware of Bitcoin since 2011 but never took it seriously until now. They raised money and put me back in the CTO chair again, which brings this narrative to today.

My appetite for further simplification has brought me to Bend, OR, where I moved only 4 months ago. I’m closer to the outdoors here, which I value in a living situation more highly than anything. Every time I’ve moved to a new place I’ve faced a period of isolation, where, before I’ve had time to make friends, I have a good few months reflect. I imagine most people go through the same thing. This time, I think I’m beginning to crystallize what I’m looking for. It’s still fuzzy, as these things always are, but it’s important to think about where you’ve come from, who you are, and what you want to be.

That’s what the second act is for: figuring it out. I’m extremely fortunate that I’ve lived a life thus far where I can continually fail at things and keep trying something else. It’s taught me a lot, and to reflect on it makes me realize how lucky I really am, even though at times the failures seem to mount pressure for a big success. I am extremely fortunate, which is the most important insight. I’ll keep that in mind and continue figuring it out. And I’m excited for act three.