How I Went From Homeless Teen to Business Owner in 7 Years

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My mother died when I was 15, and my father was in a fatal small-airplane crash when I was 17. Within 30 days of that crash, I was homeless, scared and very angry. But I was lucky. Within a short time, my life turned completely around. Here’s my story, and the lessons I learned along the way — lessons that anyone can use to move their financial life forward, even through seemingly insurmountable difficulties.

My Story

Dad was a real estate speculator who lost it all shortly before my mother died. He had a little life insurance, but not nearly enough. That amplified the pain of losing my parents and added a horrifying dimension to the loss.

I never slept on a park bench, and I didn’t go hungry very often after my parents died. But it’s a very strange feeling not to have a place to call home. And that’s how it was at first. I’ll never forget that feeling and I know it’s part of the reason I became a financial planner. More on that another time. Let’s talk about how that 17-year-old homeless kid became a successful businessman in just a few short years — and how you might apply those lessons to your own situation.

Listen, and Leverage Opportunities

I didn’t have much money, but I did have an opportunity. I qualified for Social Security survivor’s benefits, but in order to keep that support after I graduated high school, I had to go to college. So that’s what I did.

At the same time, I understood that those government benefits would go away when I reached 22, so I had to complete college by that time. And I knew I had to acquire a degree that would help me find work. That’s why I studied accounting.

But I have to level with you. I attended college because the family that took me in encouraged me to do so. I wouldn’t have even thought about it if not for them. I admired these people and looked up to them, so I listened. Bottom line? I was fortunate to receive good advice and I was smart enough to act on it. Here are some questions to ask yourself: Lucky Lessons

I was lucky. I grew up in middle-class neighborhood. I went to decent schools with decent kids. Also, when I was young, my parents explained that if I wanted spending money, I’d have to earn it. As a result, I started working outside the home at 13. This taught me the value of money and the cost of frivolous spending. I also learned that I could take care of myself and that nobody owed me anything.

I was also lucky because the people who took me in were great role models and became my new family. I am still close to my brother and sisters from that family to this day. Here are some questions to ask yourself: Motivated by Fear

People give fear a bad rap, but there are some benefits to that emotion. Because I had almost no money and no one to fall back on, I lived in a lot of fear. That motivated me like nobody’s business.

I studied hard and put all my energy into becoming a person who employers would want to hire.

Even after I entered the workforce, fear continued to drive me. When I first started my business, I regularly worked 14-hour days. That paid off financially but it does have a cost.

I am fortunate to have achieved a level of financial success at this point, but I continue to overdo it a little when it comes to work. It’s been difficult for me to find a balance. Nevertheless, that early motivation focused in the right direction really paid off tremendously. Here are some questions to ask yourself: Embrace Mistakes

Nobody enjoys admitting mistakes, but I’ve made plenty. I can tell you that I’d much rather admit to making a mistake and change direction quickly than to try to save face and allow the problem to fester.

I hated my first accounting job at a large firm, so I left after nine months. I realized that I wasn’t cut out to work for other people. It didn’t feel good to tell people I was quitting so quickly, but it was far better than staying put. I traveled for about a year and a half. Then, I searched for a job in a small company that had an entrepreneurial spirit. The owner told me that if I could achieve the growth he envisioned, he would grant me partial ownership in the firm. The deal helped both of us.

I’ve made some bad investment decisions, and I’ve hired the wrong employees. Who hasn’t made these kinds of mistakes? Rather than prolonging the pain, I like to cut my losses short. I’ve suffered small losses, but my willingness to switch directions has kept my losses to a manageable level. Here are some questions to ask yourself: Father Figure

Looking back, it’s clear that I tried to replace my dad after he died. I constantly looked for father figures to be my business mentors. While a little misguided, that quest for help was nonetheless instrumental in helping me build my business.

I was also smart enough to know I wasn’t that smart. And because the stakes were so high and I was really motivated to succeed, I wanted to get great advice from people who already had what I wanted out of life. I asked for help, listened and implemented. I found a mentor and absorbed his wisdom relentlessly. He was an MBA from Harvard and was only too happy to take me under his wing. As I succeeded, so did he. Here are some questions to ask yourself: Clear Vision

When I was young, I knew exactly what I wanted out of life. Because I lost my family at an early age, I hungered for one of my own. But I wanted them to have a very different experience than I did. I never cared about being rich. It still doesn’t interest me. My vision was simple: I wanted a family and a nice life. And I didn’t want anyone to worry about money all the time — including me. That’s it.

That clarity helped me focus on creating and maintaining an anxiety-free financial life. Because I was clear on the vision, I knew I had to do three things:

1. Make sure our spending stays in line.

2. Maximize income potential.

3. Make sure our investments are structured to create growth and income without taking on undue risk.

Here are some questions to ask yourself: Lots of people survived far worse conditions and did far better that I did. I know that I am a very lucky man and I’m grateful. You might be facing some very difficult challenges right now, and I don’t mean to downplay your situation. But I believe that you can vastly improve your situation no matter what. Here’s a recap of what I suggest you do in order to do that:

1. Look for opportunity. It’s there.

2. Draw on the positive lessons you’ve already learned. You’ve got them.

3. Harness fear in a positive way

4. Admit your mistakes and correct them ASAP.

5. Get the right mentor and take direction.

6. Be clear on where you want to go. Make sure your financial behavior is consistent with your ultimate values and objectives.

Laying it out like that makes it all sound easy, I know. It isn’t. I know that, too. But since we only go around once, isn’t it worthwhile to give it a try?

I can’t rewrite my personal history. But the cool thing is my future doesn’t have to be scripted by the past. That’s the miracle we can all take advantage of. Are you in?

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