I Founded & Own 50% of a Multi-Million Dollar Company, but 9 Years Ago I was Homeless.

The first night I slept in my car, I couldn’t sleep at all. It was cold, I was in a strange place, I had no money, and I didn’t know what I was going to do. I had never felt so worthless in my life. I wanted to die.

I came to San Francisco on December 31, 2006. I had been inspired by the new Web 2.0 scene in San Francisco. There was a small but growing core of startups in SF doing design-centric apps, using new tools like Ruby on Rails and AJAX, and talking about new methodologies like iterative development. People were meeting up and sharing new ideas and really figuring out what was possible with this new tech. I wanted to be a part of that.

I didn’t expect to get here and find myself 2 years behind everyone in the city, especially after 10 years of making stuff on the web for a living. But, I went to work, making little projects for each skill I was missing. Working night and day to fill knowledge gaps while submitting resumé after resumé and not getting any VC funded startups to even look at me.

Then I was asked to leave the place I was crashing at, and next thing I knew I was homeless. After that first night and all the anxiety that went with it I began sleeping out of my car by day at the beach and working on my laptop at the 24 hour Starbucks on California Street at night instead. I was immensely depressed, dejected, and every waking moment was met with near panic attack levels of anxiety.

I eventually found my way into some contract work with some destined-to-fail companies and got a roof over my head. On December 31, 2007 I got an email saying I no longer had a job, the startup I was contracting at had run out of money. With $20 in my bank account I started to sweat… I didn’t even have a car to sleep in anymore.

I sent out 20 resumes a day for 10 days before I got an email back from someone. It was from Zivity, a controversial but well known VC funded startup. When I got the phone call telling me I got the job as a Junior UI Engineer (just in time to guarantee a rent check for February) I fell to my knees and cried like a baby. I would not be so close to being homeless again as I did on that first anniversary of landing in San Francisco.

Finding myself inside the mainstream startup scene I took complete advantage of every opportunity. I often worked until 3 or 4 in the morning. I was killing myself and hoping people were noticing. They were. I was promoted and befriended members of the founding team. The next founder noticed too, and we became friends. Then, in 2010 I got hired by Yammer as a Senior Web Team member and one of their early (first 75) team members.

In 2012, after grinding, struggling, and killing myself for 5 years I found that I had built a large skill set, compiled a notable network, but I still hadn’t created any net worth to speak of...

That’s when my friend Mike Ihbe and I founded Must Win as 50/50 partners. With $2,000 in capital we created the corporation and dove in doing all the business development, sales, design, engineering, accounting, etc. at our little bootstrapped startup ourselves.

Over the last 4 years there have been months where we couldn’t pay ourselves, multiple relationships destroyed, and moments where we didn’t know how we’d survive. Until last year Mike and I could have been making more money pretty much anywhere else. Looking back, however, we’ve never had a negative earnings month and we’ve never had more than $20k in debt on our single corporate credit card. Over the last two years we’ve grown our revenue over 450% and worked with Cisco, Disney, Intel, Microsoft, and another 30 or so companies.

A decade ago I was homeless. Today I run a company with 10 full time employees, another 10 or so contractors, and millions in billings annually. It has been anything but easy, but I’m grateful. I have an amazing life. I feel lucky for all the breaks I’ve gotten, and more so that I was able to take advantage of as many of them as I did.

I see myself in the homeless of San Francisco every day. It hurts not to be able to help them more than I do. And, sometimes I wonder to myself if they can code, but just couldn’t string enough breaks together or seize upon them to get that job they moved here to find.

I tell you this story not to make you think I’m special, but because I know I’m not.

Everyone struggles. Nothing is as easy as it appears. While the media portrays the SF tech scene as easy money where they’re giving jobs out at the SFO baggage claim, the truth couldn’t be more different. For every tech role filled 100–1000 people get turned down. How many of those are people who just need one break? How many of those people are living in their car or on the streets? I suspect more than you or I know.

For those of you struggling to chase your dreams or losing a game everyone thinks is easy, remember that nothing is easy. Remember that everyone struggles, even those who you think of as having “made it.” Remember that you’re not alone. As long as there is air in your lungs and a fire in your gut there is always hope. Anything can happen with a little talent, enduring patience, relentless effort, and a bit of good luck.

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