Sunday, November 17th 2024
What I learned this week | Transition
Team,
It’s been a year since I last hit publish here, and I’m excited to be back. Over the past year, my cofounder and I have been writing at Huddle Stories, diving into design, startups, and the future of work. But with a career transition underway, I felt like it was time to start writing here again.
The update: Huddle, the company I’ve spent the past four years building, was recently acquired by a private equity group. While not the outcome I initially imagined, I’m genuinely excited for this next chapter — one where I’m stepping out of the CEO role.
Here’s what I’ve come to terms with: I love inventing, investing, storytelling, turning ideas into products, finding early customers, pitching investors, and coaching. That stuff lights me up. What doesn’t? Operations. HR, accounting, policies, managing teams… it’s just not my zone of genius. And that’s okay. I used to feel like admitting that was some kind of failure. Now I know it’s just about playing to my strengths.
For too long, I stayed in the CEO role out of obligation — to my investors, my team, and honestly, to my own expectations. It took me nearly four years to even Google “Replacing myself as CEO of my startup” only to find Reid Hoffman’s article about his choice to step away two years into building LinkedIn. After a lot of reflection (and some nervous conversations), I finally told my investors how I was really feeling. Their response? “That’s incredibly self-aware. We wish more founders would do the same.”
Turns out, stepping aside wasn’t a failure — it was the most aligned, high-integrity move I could have made. It was true for me, and playing to my strengths is very likely the best thing for the company, too.
I’m now working to find Huddle’s next leader while dipping my toe into what’s next for me. I’ve started a venture investing club and fundraising advisory practice to scratch my itch for variety and help other founders navigate their journey. And I’m pivoting this newsletter to reflect my shift from operator to supporter of operators. Expect the usual personal reflections plus shoutouts to founders and companies worth watching, and, just for fun, a music pick in each post. Call this last bit an ode to Ben’s Blog. (IYKYK)
If there’s one thing I’ve learned in this transition, it’s that listening to your internal compass is everything. It took me longer than I’d like to admit, but I’m glad I finally did. Thanks for sticking around — I’m excited to share this next chapter with you.
-Mike
🔖 My feed this week
Zach Bell is building MyPlace, one of my favorite startups. I’ve been a fan and user since the beginning. I use the app to share my apartment with friends, and it’s the #1 tool that’s allowed me to travel and live in two cities while building a startup. Last weekend, Zach published my favorite piece on the election: “How is this even happening?” It’s about putting yourself in someone else’s shoes and getting curious instead of pinning them as [insert judgment of choice] for voting the way they did or believing what they believe.
🎧 Listen
My first startup was at Ryan Leslie’s at SuperPhone. This Fall marks the 10th anniversary of meeting Ryan and joining his company. Four years before, his album Transition was nominated for Best Contemporary R&B Album at the 53rd Grammys (2011) — an album title fitting for this particular post.