Why You Should Make the Jump to Entrepreneurship: Lessons from Real-Life Experiences

When was the last time you felt excited about a Monday? Or any workday for that matter?

Can’t remember? Then perhaps it’s time for a change.

While some people are born entrepreneurs, others just stumble into entrepreneurship like a drunk person slipping into a bar. Some are dragged into it, kicking and screaming. Because when no one creates the solution you want, you’re left with no option but to build it yourself.

This is how I convinced my two older brothers to leave behind the security of their 9–5 jobs and fall in love with entrepreneurship.

Maybe you will, too.

The Early Years

I was born as an entrepreneur, but I’ve never had a “real” job. I dropped out of high school when I realized I’d rather build businesses than listen to lectures.

My brothers? Not so much. They both landed secure 9–5 jobs at large corporations. They’d always tell me, “Entrepreneurship is great for you, but it isn’t for us.”

But I knew that was BS. They had what it took to be amazing founders if they’d just give it a go. But they wouldn’t. They decided they couldn’t be entrepreneurs, and that was that.

One day, I found an opportunity that was too tempting not to try.

The Turning Point: DVD Vending Machines

Remember when DVD kiosks were big? A little over ten years ago, I met a guy who rented out DVD vending machines like Redbox.

At this time, big-box rental places like Blockbuster were on the decline, and Netflix had yet to become the giant it is today.

The opportunity was perfect: All we’d have to do was rent a machine, set it up in a store, and start earning a profit.

It was low-risk, low-investment, low-effort, and high potential. Even better, my brothers could do it while keeping the security of their day jobs.

After years of pitching different opportunities, I’d found the one. They agreed to try it (if I’d finally stop bugging them).

The Payoff

We were up and running shortly afterward and immediately started generating profit.

That was all my brothers needed to see; they were hooked. They wanted to use the money we were making from this machine to invest in a second location.

So we did, and our second machine outperformed the first by 5x. And that got my brother's thinking.

A couple of months later, my brothers, who swore they’d never be entrepreneurs, quit their day jobs and focused 100 percent on this new business.

Today, they run a successful multi-chain store with branding, business models, and employees.

So much for not being entrepreneurs.

The Power of Trying

Why did I keep bugging my brothers to become entrepreneurs? Was it because I was positive they’d succeed?

Of course not. There are no guarantees in Startupland.

I kept at it because I wanted my brothers to try entrepreneurship before ruling it out. If they’d come to me afterward and said, “This isn’t for us,” I’d respect that and wouldn’t ask them again.

But they didn’t. They became some of the best entrepreneurs I know because they were finally willing to try something new.

Entrepreneurship isn’t for everyone. But neither is the 9–5 grind. You can’t know what you’ll love or succeed at until you try.

3 Tips to Become More Entrepreneurial

Do you think you or someone you know has what it takes?

Here are the three most valuable lessons I learned during my 15+ years of trying to convince my brothers to become entrepreneurs.

1. Take Baby Steps

Your first venture in entrepreneurship doesn’t need to be the next Google, Uber, or Facebook. That’s like showing up to a gym for the first time and expecting to deadlift a 400-pound weight.

Test the waters with low-risk, low-investment, low-effort opportunities. And accept the fact that you might not be as lucky as my brothers. Their first business was immediately successful.

That may happen for you, but it may not. So, it’s best to start small in case things don’t go as planned. You can always scale up later.

2. Keep Your Day Job

There are many stories about people who got an idea, quit their jobs, and founded soon-to-be successful businesses in a day.

Those stories are great for inspiration, but people often forget that for every one of those stories, hundreds of people whose businesses failed.

Learn from my brothers and keep your day job as long as possible. Once you start seeing a positive investment return, consider quitting.

Until then, don’t burn bridges until you’re certain you aren’t going back.

3. Don’t Do it Alone

As an entrepreneur, there will be times you want to quit.

My brothers have often cursed me for introducing them to entrepreneurship (though both admit they’d never return to the grind).

In those times, it helps to have a co-founder to keep you accountable, committed, and sane.

The right co-founder will balance your strengths and weaknesses and bring new perspectives and insights you might otherwise overlook.

Take the Leap into Entrepreneurship: Start Small and Find Success

Let me say it again: Entrepreneurship isn’t for everyone.

I know plenty of people who have become terrible entrepreneurs and have sworn off it forever. But the important thing is that they tried.

So here’s my challenge: If you’re thinking of becoming an entrepreneur, do it. If you aren’t, try it. Start small, but start.

You’ll either succeed or you won’t. Either way, you’ll walk away with answers rather than assumptions. And once you have answers, you can start making smart decisions.