I quit my six-figure corporate job for a startup and tanked — but I’d do it again

Renting beach chairs and umbrellas, a vitamin subscription service, curated cigars, an app to pay your restaurant or bar tab, technology to measure the effectiveness of billboards.

All of these are startup ideas that I’ve had over the last 10 years. I even set up LLCs and began development work on some of them, but none ever really got off the ground.

I was starting to think that I had an entrepreneur’s mind with a banker’s risk tolerance.

Then one day I got an email about an opportunity to join a team of three that were attempting to disrupt the healthcare space. The more I learned about the inefficiencies in the healthcare industry, the more convinced and passionate I became about the concept.

And the closer I got to the opportunity, the more nervous I got about leaving my great six-figure job and putting a strain on both my finances and the desire for my wife and I to maintain some sort of work-life balance.

Weeks of hand-wringing ensued and I decided if there was a time in my life to jump in the deep end of the pool, now was it. I took a 50% pay cut and joined Novarus Healthcare in the spring of 2016.

We finalized a capital round of $750,000 and were off to the races. Or so I thought.

As it turns out, “off to the races” at early-stage startups means moving into the cheapest office space you can find with the cheapest furniture you can find. In this case, it was a couple hundred square feet in a dark basement corner of a refurbished sock factory with used furniture that we found on Craigslist.

Staying in AirBnB’s on the wrong side of the tracks while traveling and periodically stealing office supplies from the other tenants in our building wasn’t exactly what Mark Zuckerberg seemed to be doing in The Social Network.

Nonetheless, I embraced the excitement of starting from scratch and we landed a few clients, including one of my former employers.

We had great meetings with investors and large prospects in Nashville. It felt like we were on to something, I started thinking about how big we could be and all the fame and fortune that would bring. It felt like we could be the next Charlotte success story.

And then, like so many other startups, we hit a wall.

No one was telling us no, but no one was telling us yes either. I had grand ideas for marketing campaigns that we weren’t ready for. We needed revenue in the door yesterday.

So I switched gears and focused on sales (although I called it “business development” because I thought it sounded better). I started with friends who I knew would answer my calls, then quickly moved on to professional contacts, then to LinkedIn contacts that I was tangentially connected to at best, and finally to building my own outbound cold-call list from Charlotte Business Journal info.

And yes, I sat in our basement office and called so many names off that list that I lost count.

After several months of restless nights thinking about that one additional feature we needed or that one extra call we should make, our CEO and investors announced we were done.

Just like that.

My jump into the deep end of the pool suddenly felt like a free fall from highest of high dives, and I had no idea if I could swim.

The news came at 10:00am on a cold and rainy Friday, February 3rd. It was devastating. I went home and spent the rest of the day thinking about how to explain to my wife that I’d failed. When she finally did come home every word I’d thought of escaped me.

I cried instead.

The next several weeks were spent frantically trying to recreate the company with my own vision, team, and set of investors. When the realities of what it would take to pull off that monumental task set in, I started looking for other startups to join instead.

And when none of those doors would open I finally found myself applying for “corporate” jobs on company websites, a task that I was positive I would never need to undertake just a few weeks prior.

Everything had gone wrong. I’d taken a massive pay cut to bang my head against a wall, we’d admitted failure in just less than a year and now I was having trouble finding a new job.

And yet, after a year of reflection, I’d gladly do it again.

There is nothing more rewarding than chasing a dream. Accomplishing the dream is great but the real fun is in the chase and that’s what I got to do for a year.

I chased as hard as I could chase and I came up short. And I loved it. And guess what, everything is just fine a year later. It took me about three months to land a job I love at a great company, and now my wife doesn’t have to deal with me getting out of bed at 3 a.m. to update a PowerPoint.

As for the process of returning to the corporate world and explaining my failure to hiring managers — it wasn’t nearly as bad as you’d think.

I focused on the positives like the experience of pitching c-level executives, hiring and managing contractors and having to become an expert on an entirely new industry in a very compressed time frame.

Most hiring managers saw my startup experience as a positive, and, if anything, were worried I wouldn’t stay with their company long and would jump back into the startup world.

So, to all of you out there sitting on the sidelines, wringing your hands about whether or not to jump in the pool, just go ahead and do it.

You’ll be forced to fight harder than you’ve ever fought before and you’ll learn you can handle a lot more stress than you thought you could. And maybe it won’t work out, and maybe you’ll cry, too, but at least you will have tried.

You’ll certainly never know if you can swim if you don’t jump in the pool. And if it turns out swimming isn’t your thing, you’ll still be glad you jumped. I promise.