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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