Entrepreneurship: Why you should make the jump

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 stumbling 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 the story of 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 a born entrepreneur. I’ve never had a “real” job. I dropped out of high school when I realized I’d rather be building businesses than listening 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 simply decided they couldn’t be entrepreneurs, and that was that.

Until one day, when I found an opportunity too tempting not to try it.

The turning point: DVD vending machines

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

At this time, big-box rental places like Blockbuster were on the decline and Netflix hadn’t become the giant it is today.

The opportunity was perfect: All we’d have to do is 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 give it a try (if I’d finally stop bugging them).

The payoff

We were up and running shortly after 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 really got my brothers thinking.

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

Today, they’re running a successful multi-chain store complete with branding, business models, and employees.

So much for not being entrepreneurs.

The power of trying

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

Of course not. There’s 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 afterwards and said, “This isn’t for us,” then I’d respect that and wouldn’t ask them again.

But they didn’t. They ended up becoming some of the best entrepreneurs I know, all 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, what you’ll succeed at, until you try. [Tweet this!]

3 tips to become more entrepreneurial

Think you or someone you know has what it takes?

Here are the three most valuable lessons I learned spending 15+ years 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, just in case things don’t go as planned. You can always scale up later.

2. Keep your day job

There are tons of stories about people who got an idea, quit their job, 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, there are hundreds of people whose businesses failed.

Learn from my brothers and keep your day job as long as you can. Once you start seeing a positive return on your investment, then 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 cursed me many times for introducing them to entrepreneurship (though both admit they’d never go back to the grind).

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

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

You know what they say about assumptions

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

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

So here’s my challenge to you: 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.

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