From Skeptic to Believer: A Tech Bro's Coaching Journey

"Coaching Is Just Expensive Therapy"

That's what I told my co-founder when she suggested I try coaching. I was a 28-year-old startup founder running a Series A company with 30 employees. I didn't need someone to ask me how I felt. I needed solutions.

But our board was getting frustrated with my leadership style (translation: I was burning through people), and my co-founder gave me an ultimatum: get a coach or she'd find a new CEO.

Finding Someone Who Spoke My Language

I went on CoachCompass expecting corporate fluff. Instead, I used the filters — which, credit where it's due, are really well designed — to find coaches who specialized in startup founders and had tech backgrounds. I found Coach Mike—a former CTO who'd scaled two companies and had a coaching style described in reviews as "direct, no BS, results-focused."

His intro video started with: "If you want someone to hold your hand, I'm not your coach. If you want someone to hold you accountable while you build something great, let's talk."

I booked immediately.

The Wake-Up Call

Mike didn't ease me in. Session one, he asked me to describe my last three employee departures in detail. By the end, he looked at me and said, "You know you're the common denominator, right?"

No one had ever said that to me so directly. And because he'd been a founder himself, I couldn't dismiss it as someone who "didn't get it."

The Work

Over six months, Mike helped me:

Develop an actual leadership style (not just "move fast and break things")

Build a feedback culture that didn't involve yelling in Slack

Retain our top 3 engineers who were about to quit

Close our Series B with a board that actually trusted me

The Verdict

Coaching isn't therapy. It's not hand-holding. With the right coach — and CoachCompass makes finding them surprisingly easy — it's the most practical investment a founder can make. But the key is "right coach." If Mike had been a gentle life coach, I would have quit after one session. CoachCompass's filtering made the match possible — and that's exactly what they built it for.