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From Harvard Business School to RevGTM: Kevin Nakao’s Story of Reinventing Joy at Work
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Kevin Nakao’s story is one of serial reinvention. From launching a Grammy-nominated record label to leading marketing in startups and now running his own solo consultancy, Kevin’s career is a testament to lifelong learning, humility, and hustle.
In this episode of UnLost Cause, Kevin shares the lessons of choosing joy over title, getting his hands dirty again in his 50s, and why he’s more fulfilled now as a “company of one” than ever before.
⏱️ CHAPTERS
03:12 – The impact of non-traditional Asian parents
06:45 – First entrepreneurial sparks and childhood role models
11:20 – How hustle got him a job at Universal Music
17:40 – The startup shift: From record label to tech
22:55 – Realizing he didn’t want to be CEO again
27:10 – Why freelancing beat corporate leadership
32:00 – The financial and emotional planning before the leap
37:30 – Pricing lessons as a freelancer
41:10 – Company of One: Pros and cons
45:15 – AI’s impact on marketing and Kevin’s plan to stay ahead
50:40 – Family life, flexibility, and redefining success
54:05 – The emotional tax (and freedom) of freelancing
58:00 – Advice to those over 40 with simmering dreams
1:01:20 – Kevin’s ask to the UnLost Cause community
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🎧 Listen to the full podcast and subscribe on Substack: https://unlostcause.substack.com
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