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June 22, 2025 45 mins

In this season finale, Kevin pulls back the curtain on his entire book-writing and self-publishing journey. What started as a collection of blog posts became "It Depends: Writing on Technology Leadership, 2012 to 2022" – but why go the DIY route instead of working with a traditional publisher?

You'll learn:

  • The real reasons tech leaders should (or shouldn't) write books
  • Detailed breakdown of self-publishing vs. traditional publishing
  • Specific tools and workflows: from WordPress to Word, ChatGPT for indexing, and recording audiobooks at home
  • The business side: Amazon KDP vs. Ingram Spark, profit margins, and what actually sells
  • Costly mistakes to avoid (spoiler: don't waste time on fancy tooling)
  • How to promote without feeling like a sleazy self-promoter

Perfect for:

  • Anyone considering writing a book or starting a content business
  • Tech leaders thinking about building their personal brand
  • Entrepreneurs curious about the nuts and bolts of launching a creative venture

Even if you never plan to write a book, Kevin's approach to learning a new business from scratch offers valuable lessons for any side project or career pivot. Plus, you'll get the honest truth about royalties, sales numbers, and whether it's actually worth the effort.

This episode doubles as both a practical how-to guide and a case study in DIY entrepreneurship. Kevin's Gen X, do-it-yourself approach (honed from years running a record label) provides a refreshing alternative to the usual "scale fast or die" startup mentality.

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