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5 Secrets of Serial Entrepreneurs

For most entrepreneurs who have made it, the idea of starting over may generate some uncomfortable laughter or flashbacks. For others, the unpredictable route of new victories and roadblocks may be their favourite aspect of entrepreneurship—and they may have welcomed a round 2 or 3 or 4… Here’s how the serial entrepreneurs do it:

1) THEY EMBRACE THEIR CHANGING PASSIONS

Entrepreneurs are passionate people. And those passions usually evolve (whether they admit it or not). In building my last company, Fit Brains, I was inspired by the advancements in neuroscience and how brain training could be fused with gamification to help people. After Fit Brains was acquired by Rosetta Stone, I found inspiration in my family. I realized that family inspires me to work harder and persevere through obstacles. And so I went on to build my next business venture, Picniic, around family and keeping families connected.

Always have a finger on the pulse of your passions. Figure out what gets you out of bed (that may not be the same as it was three years ago!) and build your business around that.

2) THEY DON’T DO IT ALONE

Successful entrepreneurs have a team that supports their weaknesses. They look at what they’re good at and what areas are sufficiently covered. Then they figure out what they’re not so good at. And then they recruit based on that.

Serial entrepreneurs also don’t do it alone in the sense that they let their team take the steering wheel. While it goes against every entrepreneur’s instinct to not do everything from start to finish, it is necessary to delegate for business growth and to show confidence in everyone else. This frees up time that you can reallocate to areas that require your special attention. Often you may find that you’re the best at something, but that doesn’t necessarily mean you should be doing it. Silence your inner control freak, figure out what position your company needs you in the most, and delegate everything else.

3) IT’S MOSTLY ABOUT GRIT

It’s easy to pursue a new business idea. It signals a new beginning, endless possibilities, and newfound motivation. You start to wake up earlier and find a bounce in your step.

It’s really a picture-perfect scenario: an entrepreneur pursuing a new passion project.

But when the dust settles, reality kicks in. Unanswered emails, rejections, 18-hour days, cash flow issues, the list goes on. As the novelty wears off, grit becomes necessary.

Grit is rolling up your sleeves, sacrificing a long weekend because you over-promised on a deadline, or going back to the drawing board because your great idea for a new product line wasn’t so great after all. It’s compromising on your romanticized idea of what should have been and doing whatever it takes to make that a reality.

The hard thing about grit is that it goes against the basic human instinct to avoid pain and quit in the face of it. And here’s the catch: it doesn’t separate those who fail from those who succeed; it only separates those who fail from those who fail and then prevail. So grit is unnatural and therefore takes practice, and it doesn’t guarantee success from the get go. But in the long run, grit is the common denominator among successful entrepreneurs.

4) THEY DON’T REALLY KNOW WHAT’S GOING TO HAPPEN

Entrepreneurship is ambiguous. You’re expected to paint a compelling roadmap, commit to it, and charge ahead—all while looking for evidence that you got it all wrong. Serial entrepreneurs share a willingness to be wrong and switch directions mid-course. They are open to new information that may conflict with their road map right now. In the end, it boils down to trusting your gut and being agile and humble enough to change directions as circumstances change.

Believe it or not, you can actually increase your tolerance for uncertainty by pushing yourself outside of your comfort zone in day-to-day situations. For example, you can order something different off the menu, travel to a foreign country whose language you can’t speak, or turn off the GPS and let your navigational instincts kick in. The key is to start being okay with the possibility of making the wrong decision, getting lost, and being on your own.

5) THEY’RE OPTIMISTIC

It’s almost an entrepreneur’s disease to be unreasonably optimistic. And that’s because the road less travelled is inherently risky. To be willing to take those risks over and over again, and to bounce back when things don’t work out requires a high level of optimism.

Optimism matters because this is a game of ambiguity. It matters because it’s contagious, it feeds your creativity, gets you out of bed every day, and keeps you from becoming paralyzed by failure.

So maybe it isn’t a disease as much as it’s a requirement. Serial entrepreneurs need to be unreasonably optimistic—about the deadlines they can meet, setbacks they can recover from, how little money they can keep running on, etc. What’s behind those superhuman feats is the entrepreneur’s unwavering belief that he/she can do more than what’s humanly possible.

Regardless of how many projects you are looking to pursue, success comes with authenticity, strategic partnerships, willingness to get your hands dirty, knowing when to move on, and being okay with flying by the seat of your pants sometimes. For serial entrepreneurs, this means falling in love with the process of struggling. That’s what entrepreneurship is about, right?

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