By Kerry Frank / August 12, 2025
In the early days of Comply365, I had an angel investor who showed up exactly when I needed him.
He had retired from a Fortune 500 finance role and, frankly, was a little bored. He saw me pitch at a local Fast Pitch competition and then showed up again at regionals. And then again at state, where I took 2nd place in all of Illinois.
Eventually, he started volunteering at our office. We affectionately called him our “retired intern.” We used to joke that if we provided recliners and the printed newspaper, we could attract a whole army of them. He was funny, brilliant, and believed in me when very few people did.
When the time came, at a moment when we were scraping every penny to survive, he invested in the company. He helped give us a fighting chance.
But as the company started to grow, things changed.
He became frustrated that he didn’t know everything that was happening inside the company. And when we secured our first major round of venture capital, he became angry and uncooperative. He didn’t want to work with the new investors. He didn’t want to let go.
I still remember where I was when it all came to a head. I was jet lagged, standing in a hotel hallway in Asia, taking a late night call so I wouldn’t wake the teammate I was sharing a room with. I was exhausted. We were on fumes waiting for the funding to come through.
He was yelling. I stayed calm and told him we could buy him out if that’s what he wanted. He said yes. So I mailed him a check.
It was a large one.
He got a massive return on his investment in a very short period of time.
And I never heard from him again. No thank you. No congratulations. No celebration.
Just silence.
I remember saying to someone, “If I got that kind of return, I’d send a thank you note and a bottle of champagne.”
Instead, I was left with a strange sense of grief. I thought we were building something together. I thought we were aligned. I thought he believed in me.
But I learned something important that day:
Not everyone who starts with you will stay with you.
Not everyone is equipped to grow with the thing they once believed in.
And sometimes what feels like betrayal is really just the end of a season.
It wouldn’t be my first betrayal in business… and it certainly wouldn’t be my last.
But I didn’t let it stop me. And you shouldn’t either.
If you’ve ever been hurt by someone you trusted, you’re not alone.
If you’ve ever felt blindsided, abandoned, or misunderstood, you’re not crazy. Just keep going. The people who are meant to build the future with you… will.
With Gratitude,
~Kerry
#PushWeek #GritToLegact #TheRealJourney #EntrepreneurLife #FoundersJourney #Betrayal #KeepGoing #FaithInBusiness #StartupLife #Leadership #Resilience #VulnerabilityIsStrength #flightpathrewritten
I love your betrayal story. I have felt a betrayal many times. But you now are inspiring me to write about those feelings and to to take the learned lesson to another level. 🤔