Her Startup Raised $3 Million, Then It All Started Falling Apart

How 15 Minutes and One Word Prevented a Founder’s Leadership Crash

Joe Procopio
5 min readMay 2, 2022


image by creativeart on freepik

Are you ready to face your own personal leadership crisis?

It’s a question that’s almost impossible to answer until you’re faced with it. Do you run from danger or towards it? A lot of people say “towards it” until the first time they hear the sirens, then “fight” evaporates and “flight” kicks in.

Last week, a first-time founder and CEO reached out to me and asked for 15 minutes of my time. I rarely do that these days, as my own projects continue to kick into high gear, including one that exists just to answer as many entrepreneur and leadership questions as possible.

But all the stars lined up for this request. The startup was legit, having raised $3 million and closing in on $1 million trailing annual revenue. The industry was similar to what I do and the problem was one I had faced frequently over my long career as an entrepreneur.

The problem, in a nutshell, was that even with all that success, the founder/CEO was losing control. Her company was overpromising and under-delivering. Deadlines weren’t being met. Runway was burning. Investors were frustrated. Customers were angry.

She had been doing so well, but was now bordering on her very first leadership crisis. So I hopped on a Zoom for a very fast 15 minutes.

The First 5 Minutes: Who Are You?

Every startup is unique. Every leader is unique. We all have strengths and weaknesses. The trick is leaning into those strengths and understanding those weaknesses. So we spent the first five minutes figuring out who she is and what her strengths and weaknesses were.

Turns out she’s a technical founder, and in fact a technologist by trade. Her product is a high-tech product, and her executive and management team is entirely constructed of technical talent. There is not an experienced business leader in the bunch.

This is a problem, yes, but not an insurmountable one.

Her strengths are in guiding her company’s technical solution. With that much genius talent on board, her product has the…



Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building TeachingStartup.com & GROWERS. Write at Inc.com and BuiltIn.com. More at joeprocopio.com