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
1. Growth at all costs: The great illusion
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. Overhead remained monstrous. And let’s not even get into how some competitors acted like they were throwing a party during tough times.
The ugly truth is that rapid growth without financial discipline is a time bomb. Growth isn’t success if it can’t survive turbulence. And by the way — VCs aren’t always right. Some advice comes with a giant asterisk that says: “Not responsible for when this blows up.”
Today, we focus on healthy, calculated growth. Customer obsession first. Sound financials second. Vanity metrics dead last.
Lesson learned: Growth is amazing — until you realize you need to pay for it.
2. Choosing the wrong partner: The fastest way to burn out
You know how they say business partners are like spouses? They’re wrong. It’s actually worse — because at least in marriage, there’s usually cake.
Over the years, I’ve seen (and lived) what happens when you pick the wrong partner. As an investor today, I watch it unfold all the time: founders trying to quietly jump off the bandwagon of their own companies, citing “health issues,” “new opportunities” or “life pivots.”
Translation? They want out. Fast.
When you tie yourself to someone — whether you’re starting a company or buying into one — you’re betting on their character, not their resume. You need someone who’s ready to crawl through the mud when things get ugly, not someone who checks out at the first bump.
I’ve partnered with the wrong people before. Trust me, no amount of contracts, equity splits or board meetings can fix a partner who’s already mentally gone.
When I look back at SetSchedule and my later investments, the best outcomes were always with partners who had grit. Partners who took the hits and stayed in the fight.
Lesson learned: A bad partner will sink the ship faster than bad revenue.
Related: A Bad Business Partner Could Cost You Millions — Here’s How to Avoid a Toxic Partnership
3. Hiring the wrong people: Resume roulette
Let’s talk about hiring at scale — a brutal art form where it’s far too easy to pick the wrong players.
At SetSchedule, we have hired thousands over the years. Early on, we made the classic mistake: chasing credentials. Fancy degrees, blue-chip company backgrounds, impeccable references — on paper, it all looked amazing.
In reality? Some of the flashiest hires were the first to jump ship when the going got tough — or worse, the first to complain while others were rolling up their sleeves.
The real MVPs were the ones who genuinely bought into the mission. The ones who believed — not because of a six-figure package, but because they wanted to build something bigger than themselves. They didn’t care about corporate politics, title upgrades or catered lunches. They cared about winning together.
Today, when I’m hiring or advising companies, I tell founders: Hire missionaries, not mercenaries. You want people who drink the Kool-Aid (voluntarily), not the ones who negotiate how much Kool-Aid they get before they even show up.
Lesson learned: A great company isn’t built by collecting resumes — it’s built by collecting believers.
Related: The 3 Biggest Hiring Mistakes You Can Make
Mistakes aren’t scars on your entrepreneurial journey — they’re badges.
Chasing growth blindly, picking the wrong partners and hiring based on surface-level shine all could have taken me down. Instead, they forced me to build thicker skin, sharper instincts and better businesses.
SetSchedule’s success wasn’t despite the mistakes — it was because of what the mistakes taught us.
So, if you’re out there right now, staring down a bad decision, remember this: Sometimes the worst moves you make end up pushing you toward the best version of yourself.
You just have to survive them first.
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.
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