Bankrupt at 25, Riding a Bike 15 Miles to Work: What Rock Bottom Taught Me About Decisions

People hear that I built a company from $500 to seven figures and assume I had it figured out early. I didn't.

At 25, I was bankrupt. And I want to tell you how I got there, because the pattern that put me there is the same one I see in business owners all the time.

How did I end up bankrupt at 25?

In my early twenties, I had good credit, and I used it. I took out personal loans and ran up credit cards to bridge one thing to the next.

The problem was that none of that borrowing was meant to grow anything. It wasn't an investment in a skill, a business or a way to earn more. It was just a way to keep going without changing anything.

I traded a car I loved for a bigger one because I thought that's what growing up looked like, and I was underwater on it the moment I drove it off the lot. I made decision after decision for the wrong reasons.

By the time I was waiting tables in Florida, I had around $60,000 in debt, plus the car, which brought it to about $80,000. I was making about $20,000 a year. In 2005, I filed for bankruptcy.

What did rock bottom actually look like?

After the bankruptcy, I gave the car back and started over with nothing. I'd saved about $700, my parents matched it, and I bought a $1,200 car from a sketchy lot.

It lasted about 32 days. One night the catalytic converter blew, and when I finally got it into a shop, the engine timing was off too. The repair was going to cost $1,200, the same as I'd paid for the car. I sold it for scrap and walked away with about $10 in my pocket.

I had to work the next day, and the restaurant was 11 miles away. The only way across the river by bike added a few more miles, so it was closer to 15 miles each way.

So that's what I did. For about two and a half to three months, I rode a bicycle about 15 miles to work, waited tables, and rode 15 miles home.

Eventually a regular at the restaurant heard about my situation and lent me a 50cc scooter that topped out around 30 miles an hour. It cut my commute in half, and I was grateful for every mile of it.

That was rock bottom. I wasn't just sitting on the bottom. I was being dragged across it.

What changed?

One morning in March 2006, I woke up and knew I didn't want to wait tables anymore. It just hit me. There had to be more to life than the struggle I'd been pulling myself through.

So I put my resume on a job site, as weak as it was at the time. An insurance company called and offered me a commission-only sales job. I got licensed and worked there for about six months.

I didn't make much money, and my mindset hadn't changed yet. But it was worth leaving the restaurant, because it got me moving. Through that job I met someone who later told me about a mortgage company that was hiring, and walking through that door changed my life.

None of that would have happened if I'd stayed where I was, waiting for things to get better on their own.

What does this have to do with running a business?

Looking back, the bankruptcy wasn't really about money. It was about how I made decisions.

I chose what felt good right now over what would actually move me forward. I borrowed to avoid change instead of to create it. And I kept making the same kinds of choices while expecting a different result.

I see that same pattern in business owners every day. They spend on tools, hires or marketing to make the discomfort go away, not to solve the real problem. They keep running the same playbook and wonder why the numbers don't move.

Rock bottom is just the most extreme version of a plateau. You can stay there a long time if you keep making decisions for the wrong reasons.

What did I learn that I still use today?

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