Entrepreneurship is like jumping out of an airplane and building the parachute on the way down. You don't always get it right — and trust me, I missed a few stitches on the way.

As CEO of SetSchedule, I scaled a company from $0 to over $10 million in annual recurring revenue, built a team that grew to over 1,000 employees and lived to tell the tale. But behind every highlight reel were moments that, at the time, felt like disasters.

Looking back, the worst decisions I made weren't just painful — they were necessary. They gave me the tools I needed to become a better leader, operator and investor. Here are the top three terrible choices that (ironically) paved the way for real success.

Related: The 3 Biggest Mistakes That Made Me a Better Entrepreneur

Here's a rookie move: Believe that growth solves everything. Revenue cures all ills, right? Wrong.

Early on at SetSchedule, I drank the same Kool-Aid many venture capitalists pass around: Grow fast, ask questions later. Hire everyone. Open new offices. Light money on fire if it looks impressive enough.

For a while, it worked. We scaled like crazy, celebrated our milestones and popped the champagne. Then came the real estate market shifts. Suddenly, our "invincible" model was exposed. Revenues slowed.

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