What happens when you're so obsessed with winning that you stop seeing what you're tolerating?
It happened to Pierre. He built a startup he loved, landed in Forbes and CNBC, and raised $2 million. Then, the red flags started piling up. One of them was sitting on his own team.
Pierre's story is a reminder that failure doesn't always start with one big decision. Sometimes, it starts with the things we choose to tolerate.
Want to hear how it all went down? Keep reading…
👤 Who?
Husband, father, and entrepreneur. Pierre Rogers spent 15 years in financial services at Bank of America and Prudential before walking away to start over. After going from Forbes coverage and a thriving startup to losing everything and spending 18 months in federal prison, he rebuilt his life and co-founded a new company.
Today, he speaks about resilience, reinvention, and what failure actually teaches you.
🧭 FuN: What was the context before this story?
Pierre: In 2018, I realized that no matter what wine store or liquor store I walked into, whether it was Portland, Maine, or Portland, Oregon, most of the brands were exactly the same.
And that kind of got me thinking: why?
Well, ultimately I decided to start a wine-selling software business to disrupt the industry positively. We raised about 2 million bucks, and off we went.
We had all the makings of a successful startup, and very quickly we had the largest, or at least one of the largest, inventories online of wine anywhere in the United States.
I poured everything into my startup. All of my savings and all of what I call my reputational capital. I had no backup plan, and that would backfire hard.
💣 FuN: How did your fuckup begin?
Pierre: As we scaled, the pressure grew. My workdays got longer and longer, and the pace got faster and faster.
Ultimately, I hired someone to manage compliance, finances, and growth. Unfortunately, I trusted the wrong person. I hired my best friend and gave him total operational control.
Then most of the staff came to me individually, one by one, and told me he wasn't cutting the mustard.
They were showing up late. They weren't providing the proper support, and they weren't what we needed in a leadership position.
What did I do? I failed to realize it was time to go back to that person, adjust, give feedback, coach them up, and properly supervise them.
💥 FuN: What was the wake-up call?
Pierre: I'll never forget it. It was 3:00 in the morning. I was in a hotel in Honolulu, Hawaii, in the dark, with the air conditioning cranking, and the phone was ringing.
I had my wife's phone in line. Her voice was shaking. She was so incredibly upset. The moment I heard it, I felt afraid that something terrible had happened.
She said they were there to arrest me.
My thoughts spun. I had no idea what was gonna happen to me, my company, my family. It was a pile of rubble made of absolute destruction.
A series of smaller red flags had appeared along the way, and I failed to see every one of them. I failed to manage and supervise that person properly because I let my personal feelings get involved. Ultimately, that led to the company's downfall.
A federal indictment came down because of those illegal activities I failed to supervise. The company failed, I was sentenced to prison, and everything I worked for collapsed overnight.
Serving my sentence, separated from my family, was one of the most devastating things in my entire life.
🔥 FuN: What happened next?
Pierre: After my release, I had a profound realization.
Absolute accountability starts with being completely vulnerable: admitting that I don't know everything, that I screwed up, and that I take 100% ownership of everything that happened.
And I want that to be really clear. There's one person at fault here, and it's me.
I started sharing my story because people need to understand that failure is not the end.
A public failure, a public collapse not accepted by you, is not the end of your story.
While it may close one door, it will force you to go through the door you were always meant to open. That's why you actually have a seat at the table.
📝FuN: What did you learn?
- What you tolerate matters. Don't let favoritism cloud your judgment.
- Character matters more than talent. If someone lacks the work ethic, principles, and character that you have, no amount of talent can compensate for that.
- Slow down. Talk through the second- and third-level consequences of your decisions. Rash actions produce rash results. You have more time than you think. Take it.
- Keep the promises you make to yourself. Once you build a track record of never breaking your own promises, your self-confidence increases, and so does your ability to tell other people to fuck right off.
🔗 Connect with Pierre: Instagram | LinkedIn | Website
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