How Homelessness Prepares You For Entrepreneurship

By Jimmy Murray

Every life challenge is an opportunity to grow and succeed in life and business.

The cop was friendly enough. Just a wellness check. I had been snoring for 48 straight hours at the library. My beard was long enough to suggest that something was wrong, but short enough to suggest that I was taking care of myself, even at inconsistent checkpoints. My body odor was that of an engineering major. No. Big. Deal.

I was now on week three of transient housing and summer was rearing its ugly head. Philosophically, I began to debate whether it was better to be homeless in the cold or the warmth. My brain swiftly reminded me it was better not to be homeless at all.

“Turn to friends! Turn to family!” I internally shouted. I had to quietly remind myself that I had ensured those bridges burned so that I was forced to take care of myself. Man, what the mind does and decides in the darkest of times, in the darkest of places.

I began to ruminate on my next move. It’s weird not knowing what’s coming next, having absolutely no direction. How do normal homeless people do this? I needed to do something to get back on my feet and rebuild those smoldering bridges.

I cashed out my last $50 and headed to the bus station. I would return to my mother, and we could collectively mooch off the government together. For eight hours, I wondered when I would be human again. But how did I even get here?

The Cause

Living rent-free is a worthy goal. I highly recommend it. With 30-60 percent of paychecks going for housing that goes unoccupied about 50 percent of the time, it is nice to avoid that cost if at all possible. Just make sure rent-free does not mean roof-free.

The year was 2007, and all of my opportunities seemed to coalesce. I was doing a fantastic job at becoming a local celebrity on campus thanks to my experiences with stand-up, improv, and sketch comedy, and, very soon, I would begin experimenting with the newly updated YouTube and maybe give podcasting a try. My newly minted video game business would surely be bringing in money at any time. On top of everything, I had a wonderfully supportive girlfriend.

Then nearly all of my opportunities seemed to wither. I think most in America had a similar experience, and I certainly do not want to make my story seem as bad or worse than those of people who, you know, lost houses and decades of savings. All I lost was a few years of growth and earning potential. My business failed. Surprise. My business partner and I were unable to capitalize on our market. Luckily, I had bet everything not on savings, but on credit cards. Fantastic. My wonderfully supportive girlfriend left me. Instead of capitalizing on that pain, I wrestled with it on my own.

Things got low; things got dark.

The morning after I purposefully swallowed too many pills, everything was numb. It also tasted like pills. My friends found me, fed me, and took me to school to meet with the college community manager. It was funny. At the time I needed the most help, my university needed to expel me. Awesome. Every moment that I thought my life could not possibly get any lower, it did.

With no one left to support me, I became homeless.

The Duration

The thing to understand about homelessness is that it can (and does) happen to anybody. It is usually due to an institutional failure of about a hundred different support systems that a person has, much like my own. Recurring homelessness is a chicken and egg problem where one is unable to reassimilate into society, due to not having an address, thus no ability to secure employment, to secure an address, etc.

It takes a lot of hard work to find a job and emerge victorious. You have no idea what the business owner really thinks of you. You have no real way of adding value to a business. If you did, you have no ability to maintain the odor of a normal human being. It is debilitating and awful. You really need to bring your A game everyday, which is hard to do without a shower nearby or the ability to cook. You are often beholden to what little scraps you can find.

You are fighting every expense. It’s one of life’s biggest ironies that it’s really expensive to be poor. I was lucky. I looked young enough and my student ID was valid long enough that I could shower on campus. A lot of people in that situation aren’t as lucky. I was beholden to the modicum of food I could find. Most of my caloric intake was in sodas. A lack of habitat makes it hard to save. You can’t buy in bulk. You can’t buy things to cook. Any money you get disappears quickly.

A setback can happen at any moment. You get hurt? That’s a hospital bill that you can’t pay, which then goes to collections and wrecks your credit. You missed the bus? Guess you didn’t need that job after all. Oh, you’re late getting to the shelter? No cot for you.

You have to be resourceful. Every advantage you can get is going to matter. Making friends with the bus driver might get you a free ride one day. The students are moving out? Sweet! Maybe I can get a free backpack for some semblance of storage. Still have an ID? Cool! You can go to the library and learn a skill that can be useful to getting a job.

Every moment matters. When you’re homeless, most of your time is spent looking for opportunity from a business that pities you or a government agency. In either case, you have no leverage, so it’s long lines for you. The only way to mitigate these long lines is to be prepared for every possibility. Every bus ride. Every walk. Every free moment has to be spent mentally preparing for the worst of these situations.

You have to reach out to people. This was hard for me, as I had burned my bridges. Really, the only thing that kept me sane was the thought that at the end of it, I would have gained strength through perseverance.

You have to sell yourself. This was…the hardest pill to swallow. At the end of the day, you have to be your own advocate. That means finding anything that can be of value to people. For me, that came in brute strength and agility. I’ll wash dishes and clean the lobby and do it faster and cheaper than anybody else. From that starting point, a proverbial steady game of chess began, and strategic moves followed. By the way, in addition to those things, I can lead people. I moved from hawking bagels to customer service this way.

The Escape

Sick of the second-class citizenry that comes with homelessness, I made a plan. I moved back in with my mom. I had a rent-free roof and an address. From there, I made myself available at all hours. Day by day, move by move, I found myself in areas with better opportunity. I capitalized on every one of them. When I lived in Pittsburgh, I had a wonderful interview and landed a customer service job. That led to a customer service position in Raleigh. From there, I studied the market and took up coding. That doubled my income. Within two years, my bank account swelled and my skill set grew. By the end, I was helping small- and medium-sized businesses optimize their workflow and increase employee morale. Now I live in Tampa and, after studying AI, I can do whatever I want, whenever I want. That means voice acting—but I’ll always love pushing businesses forward.

The Lessons

There are a ton of parallels between homelessness and entrepreneurship. It takes a lot of hard work to emerge victorious. Be resilient. You are fighting every expense. Prevent what you can and look forward for anything else. A setback can happen at any moment. Be prepared. You have to be resourceful. Every moment matters. You have to reach out to people. You have to sell yourself.

The end goal is to be in a much better life situation. I’ve had nothing and I’ve had more money than I knew what to do with. It felt much better and more rewarding to pull myself out of homelessness than it did to rest on the laurels of my bank account. Every life challenge is an opportunity to grow and succeed in life and business.

Make a plan, put your head down, and execute.

Stay strong, entrepreneurs.

Jimmy Murray studied marketing and film and minored in singing before the economic “Big Fall” of 2007. Since then, he’s taught himself coding and artificial intelligence and gone from bagel jockey to voice over artist in four swift moves. His eye for efficiency constantly adds value to any and all businesses. He’s a beast at content creation on all platforms and enjoys teaching people creativity. Above all else, he enjoys motivating people because nothing is impossible. Follow Jimmy on Twitter: @TheJimmyMurray. Enjoy his “Kid Friendly Joke of the Day” at


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