Ninety minutes until we have to check out. I’ve been meaning to do a lot more writing on this two week journey of the Pacific Northwest. It’s been over a year since my last post and an incredible amount has happened in my life during that time. It’s difficult to know where to start, or whether I’ll like what comes out, but it’s time.

My wife keeps insisting that the best way to start writing again is, to start writing again. She’s probably correct.

The last year or so has been laser-focused on making a dream connect with reality. What a wild journey it’s been.

To get caught up to where we are, it’s helpful to know where we were. Let’s recap the last 15 years or so.


View from the Porch in Montana

Teenager living in Nowhere, Montana, on the Internet. I dreamed of being in the Silicon Valley creating amazing technological things. I often thought to myself: “If I could just get someone to trust that I’m good at what I do, hire me, give me money, and let me go, I could do amazing things.” I had no idea what that actually looked like, but I had a feeling there was something out there like that.

Graduated. Class of 2000. So many expectations on our shoulders. Started at University of Montana, hated the theatre program for its overemphasis, and near obsession, of method acting. Headed out to the East Coast towards Virginia.


Slow down a sec. Software degree first, to fall back on. Theatre degree next.

Me Playing Joseph K in The Trial

I connected with the stage just as much as computers, so I pursued my acting career after securing a software degree. Computers continued to be my favorite pastime when I wasn’t running lines, tending bar, teaching, being a barista, experimenting and learning about life, or doing the other things that filled my twenties.

Secured some amazing roles. Did professional acting work. Life was very full; the opposite of my wallet.

Setting course for San Francisco. Acting works out? Great! I’ll keep going. If not? Well, there’s always that software degree and my 20+ years of computing experience. Should be fine. Pack up the Isuzu Amigo with everything I can fit. Give away the rest. Hit the road for another cross-country trek.

Back to Montana – First Tech Job

Stop back in Montana for a bit to visit the folks. Met a girl. Got a job at a growing web hosting startup to hang out for a bit with said girl.

Modwest was my first big boy technology job.

The 3 most important things I learned from my first job in technology:

1) I didn’t know shit.

2) I was really bad at admitting the fact that I didn’t know shit and even worse at asking questions about the shit I thought I knew, but didn’t.

3) The phrase “I don’t know” is one of the most powerful things you can say to yourself or others.

Modwest and Grupthink

The folks I was working with were lightyears beyond me in terms of system administration, computer knowledge, programming abilities, the Internet, and the web in general. For the first time in my life, I was surrounded by people who made me look and feel dumb about my computing and software knowledge every day.

I started off doing technical support (which is where I recommend lots of folks who have grown up with computers get started). Nothing teaches you empathy for your users like having them cry their eyes out to you at 5:15am because their managed server bit the dust sending their hundreds of customers completely offline.

I was given the opportunity to begin programming. Started increasing my Linux skills. We were one of the largest shared web hosting PHP providers on the planet. 2006 or 2007 murmurs of “The Cloud” were increasing. It would be the death of shared hosting. But, I had moved onto developing one of the first big Q & A platforms for Web 2.0. I started being introduced to entrepreneurship, and the struggles of building a startup and figuring out how to monetize it. Incredibly insightful if not lucrative, it was eventually acquired. The web hosting startup was also later acquired; a survivor attempting to climb up above the clouds discovering how terrible water vapor was for handholds.

Starting Smoke Reports and the Caribbean

During this time, I also got more heavily involved in cannabis. The politics, the science, the people, the plant; my interest grew. I wrote Smoke Reports. Compiled genetics for over 2,500 strains of cannabis, and put them online. Created the first chart to ever map out the cannabinoid biosynthesis process. Absorbed every academic research paper I could get my hands on.

I also got married to that girl I mentioned. Marriage doesn’t always make things better. Got separated. Was offered a job in the Virgin Islands programming for an energy company. Visited the islands to see if I wanted the job. Got divorced. Moved to the islands.

Jumping off a boat into the bathtub that is the Caribbean was the beginning of a new life.

With my time at the energy company, I wrote complex trading algorithms, developed a large internal data exception and reconciliation engine, and more. I got to write queries for hundreds of GB worth of data in MySQL, my programming skills increased and I got the opportunity to experience what being “just a programmer” in a large, non-technical, organization was really like.

It definitely wasn’t for me. I went back to freelancing. Lived “the dream” of writing code while looking at palm trees and drinking a Mai Tai. Wasn’t for me. Maybe 10 or 20 years from now me, but wasn’t for me right then and there.

I needed to go back to my dream: “If I could just get someone to trust that I’m good at what I do, hire me, give me money, and let me go, I could do amazing things.”

Discovering Startups and Entrepreneurship

Passing my mid-twenties was where I began to realize I wasn’t looking for a dream boss to let me loose on projects. I wasn’t looking for the right fit in the right company. What I was looking for, was the opportunity to prove myself. This didn’t come in the form of a boss. This didn’t come from joining a company. This came from becoming an entrepreneur, building something, and getting people to believe in you.

That realization was only possible after stumbling upon Hacker News. Around 5 years ago or so, I came across a place where developers weren’t just programmers, they were business owners. They were in charge of teams consisting of hundreds, if not thousands of people. There were people who worshipped innovation and innovators? There were people getting millions of dollars for their ideas? You didn’t even need to be concretely making money, you just had to “make something people want” and you could prosper? I needed to have more.

I approached entrepreneurship like I approached anything I want to learn about: with an obsessive voraciousness of knowledge. I started idling in #startups on Freenode, started commenting, started learning, started engaging.

Then I started interviewing. Decided on a job as a developer for a YCombinator company (a dream chance at the time). Flew out to Silicon Valley. Landed the job. Became CTO. Built things. Learned what to do. Learned what not to do. Left that job.

Then I started interviewing. Decided on a job as a developer for a startup just getting off the ground, not wanting to be in a CTO-style position for the time being. Fell into a CTO-style position again despite wanting to just write code. Left that job.

Realized it was now or never.

Back to Smoke Reports

Introduced to Laravel. Enjoyed the heck out of it. Spent all of my free time rewriting Smoke Reports in Laravel. Introduced the newly rewritten product to a person connected with fundraising experience.

Now I’ve made something people want. I have employees and millions of hits a month of folks who believe in what we’re doing. We have paying customers. I found people to believe in me. I don’t have a boss, I didn’t get hired at a company. I made one.

I didn’t go to business school. I don’t have MBA fraternity buddies. I don’t have prestigious connections at top Universities in my field.

But I care about cannabis. I care about people. I care about software and technology. And I’m doing something about it.

Wrapping up a two week journey talking to folks about cannabis, people, software, and technology in other states. Lots to share.

For now: time’s up. Back on the road.

Expect more writings from me. Follow me on Twitter @randomdrake to keep up.