Leaving the C-Suite for Freelancing and Freedom
Kevin Nakao had it all. Harvard MBA, large Marketing teams, but he yearned to get his hands dirty and to do the work. So he left it behind to start RevGTM in his 50's.
I’ve known Kevin Nakao as a tech operator, startup whisperer, and one of the sharpest marketers in my circle. But what struck me most in my conversation with him was not his résume but the reasons behind relentless reinvention. Kevin didn’t have one lost cause. He’s had many.
Top 5 Takeaways from My Conversation with Kevin:
Education for learning’s sake:
Kevin grew up in a household where education was valued—but not for prestige or paychecks. His parents celebrated curiosity. When he switched to studying philosophy, they said, “That’s great! What’s it like?” That mindset of unconditional encouragement stayed with him.Informational Interviews Can Be Life-Changing:
This was one of my favorite parts of the interview. After graduating from Harvard Business School, Kevin eschewed high paying management consulting and investment banking jobs. In fact, he was the last person in his ENTIRE class to find a job.Kevin hustled. And he got his first dream job in the music industry by showing up relentlessly—and being kind to an executive assistant who ultimately unlocked the door. “Always be nice to the gatekeepers,” he said. “They often hold the keys.”
In fact, he was hired ON THE SPOT when he got past the gatekeeper and met with the executive. You’ll certainly be inspired when listening to how this all came together for him.
Reinvention is a Mindset, Not a Moment:
From launching a Grammy-nominated record label to joining startups to founding his consultancy RevGTM, Kevin doesn’t define success by scale or title. He defines it by agency and learning. “I didn’t want to be a CEO again. I wanted to do the work I love.”
Being a Company of One = Autonomy + Accountability:
With RevGTM, Kevin makes lunches for his kids, skips soul-draining meetings, and still runs sophisticated marketing campaigns. He’s more hands-on than ever—and more fulfilled. “I don’t need prestige. I just need impact.” We both read “Company of One,” and it’s certainly counterintuitive and thought provoking.Chase Learning When Things Get Hard:
When business slows, Kevin reinvests in himself. “That gives me hope,” he said. “Learning something new is how I claw back momentum.” Whether it’s mastering Meta Ads or diving into AI SQL tools like Blaze, Kevin stays sharp by staying curious. As a result, Kevin isn’t scared of the AI wave because he’ll be leaning in and surfing it versus fighting it.
Closing Thoughts:
Kevin reminded me that reinvention doesn’t always look like a leap. Sometimes, it’s a pivot. Sometimes, it’s letting go of prestige and returning to joy. If you’re over 40 and wondering, “Is it too late?”—Kevin’s story is your proof that it’s not.
👉 What did you take away from Kevin’s journey? Hit reply or share your reflections.