How a poker player turns into a tech entrepreneur
This is my first crack at writing and starting a blog. I’ve thought about it for a while as I’ve attempted to navigate the roller coaster that is my life. I’ve often thought documenting my crazy journey might be worthwhile and maybe someone out there will get some value from it. Well if that’s you — welcome and beware :).
This post is the beginning of what I hope will be somewhat of a journal of my thoughts, progress, and random insights as I navigate through building a tech startup while transitioning from life as a professional poker player.
Let’s start off with some of the obligatory stats:
Age: 32
Location: Currently Las Vegas, NV
Occupation: Founder and CEO of Documo
The beginning:
I was raised the second of 4 brothers by a single Mom in a small town in northeastern New Mexico (coincidentally also called Las Vegas). My Mom worked multiple jobs while putting herself through school. So by pure necessity, I grew up very independent. I had to solve things on my own and there wasn’t much in the form of any real support system for most of my childhood. Luckily, I was given strong genetics and a strong, analytical mind.
I went through grade school as a straight-A student. I had my sights set on some illustrious corporate career after of course going to some prestigious Ivy League school. Fate however, had other plans. I dropped out of school at 17 and my brother left at 16. Our family situation was very unstable and unhealthy and we decided to get an apartment together. This meant I needed to work full-time and working at the mall for $7.50 an hour wasn’t going to cut it.
I decided to try my hand at sales after learning that salespeople earned commission which could amount to much more than any hourly job I could get as a 17 year-old high school dropout. This proved to be true. After starting in a call center making 300 cold calls a day, I quickly excelled and moved up the ranks. At 19, I found myself originating loans for a mortgage broker. My 3rd month on the job, I earned a commission check for something like $20,000. This was in 2004. That same year, I met a guy at work who invited me to his home poker game. I’d never really played poker before, but sounded like a good time so figured why not?
So this is a good time to mention that I’m a very competitive person by nature. Put in a competitive situation, I become obsessive about being the best and winning. I had a blast playing that $20 home game for the first time. Poker had so many elements that spoke to me — math, psychology, mental stimulation, competition — all things that I enjoyed and was good at. I started playing pretty regularly and I started getting better.
Fast forward a couple years and I decided to get my series 7 and 63 (stockbrokers licenses) to pursue a high-paying career in financial services. A couple years later I moved to Colorado (I’d been living in Arizona). During this time, I was playing poker online regularly and now being of legal age, I was also playing at local casinos on weekends mostly but sometimes also during the week, sometimes foregoing sleep and going straight from poker to work.
Finally the day came. I came to a point where I was going through the motions at work, but I was always just counting down the time to get out of the office. It had been this way for some time. I was so focused on picking a career that made the most money, I forgot to consider if I’d actually enjoy what I’d be doing every day. Well I found the answer and it was a resounding NO.
So I quit my job with absolutely no plan for the future. I started playing poker online full time and next thing I knew 3 years had passed. I was making very good money. I took a very meticulous approach to the game and figured out how to use my skill set to my advantage and turn it into profit. I learned how to manage risk, manage money, and dig into analytics that helped me find holes in my game and improve as a player. It felt like everything was just the way it should be. Fate however, intervened again.
In April of 2011, Black Friday rocked the online poker industry. Basically, some of the online poker sites were doing some not-so-legal things in the background and the federal government got involved and effectively shut down online poker access to players in the US. So in a nutshell, I woke up without a source of income and also found out that I had no access to the considerable funds I had on some of these sites.
At this time I was living in New York. So I decided to invest some money into a tech startup with someone I had met only once and then headed out west to (you guessed it) Las Vegas so I could continue playing poker while also helping out with this tech venture.
Well I learned 2 things fairly quickly-
1. Online poker and live poker are NOT the same thing and
2. Starting a new company is hard. Like really hard.
Still, I’ve always prided myself on being a fast learner and adaptable. So I spent the next year learning how to adjust to playing live poker and learning what building a tech product is all about. I leaned heavily on my partner at the time to make decisions and build the product (I had zero technical background). It was a very part-time effort for me. Basically, I wanted to be an investor but also wanted to learn about tech as I’ve always had an interest. Of course my expectations were well out of line as building a company is a ton of work and real success requires more than a part time effort. When the opportunity arose to sell my shares of the business, I gladly accepted.
Although the investment didn’t end up making the millions that I had dreamed about, I learned some very important things. I learned the basics about running a business and some of the challenges and decisions that get made in the process, and more importantly, I learned that I wanted to be involved in tech in some capacity. I love technology and solving problems and working in tech kept me close to both things.
So over the next few years I ended up moving to San Diego to work for a small family-owned tech firm. I continued to play poker on a part-time basis and I continued to learn about technology and how to run a tech business. I got to work closely with the owners of this small company and was involved in many key decisions related to the business. When the business was acquired 2 years ago, I had a decision to make. I was offered a role with the new company that paid really well but would become more of a “corporate” role with a larger company. I would lose that smaller, family environment as well as a lot of the freedom and responsibility that I enjoyed.
I chose to decline the offer (as well as the stock options that came with it) and start a new business. I was on my own this time but I felt more educated and more importantly, I had identified a problem and market opportunity that I was passionate about solving.
I knew absolutely nothing about fundraising and the thought never even crossed my mind. So I self-funded my project and moved back to playing poker full time while I built the first version of the product, website and figured out how I was going to turn my ideas into an actual business. Somehow, this actually worked out ok as I had an income but also freedom to create my own schedule and work on my project. I played mostly out of the LA card rooms while also traveling to Vegas and other places occasionally to play certain tournaments and cash games.
During this time I met another full-time poker player (also named Matt) with a family (wife and 2 small kids) who lived in San Diego. We played some of the same cash games and it became obvious he was sharp and one of the better players in the mixed games I played. We ended up getting to know each other and even carpooling up to LA to play tournaments (ya poker players can be economical too!). He was also a long time poker player who, although profitable, was interested in doing something more with his life than playing poker. We became friends and after I shared details about my business and vision with him, we decided to work together and we became 50/50 partners.
So that brings us to today. We are just finishing up raising an investment round to help us get to the next level (more on this in future post). We’re 2 poker players with totally non-traditional backgrounds who are focused on building a technology company. We’re self taught in everything we’ve done and we are both passionate about the problems we are solving and delighting our customers.
I started this blog to help document our journey and maybe give others who are interested insight into what it’s really like to start, fund, and grow a business. Perhaps it will serve as a good manual for what not to do or just material for laughs. Either way, I hope it adds some value :)
Matt H