Hacks & Hobbies

From telemarketing to shaping New York Times bestsellers — Tom Freiling’s publishing journey is a lesson in curiosity, grit and human storytelling.  In this episode Tom pulls back the curtain on 30+ years in publishing, the shift from bookstore gatekeepers to Amazon-era discoverability struggles, and why the rise of AI makes the uniquely human elements of a book more valuable than ever. Tom shares hard-won operational lessons (how a bootstrap mindset scales), the mistakes that make self-published books “dead on arrival,” and practical frameworks for coaches, founders and creators who want to turn lived experience into a book that actually sells. Five key takeaways The bookstore era vs. the Amazon era: discoverability changed — best‑seller lists and reviews now act as gatekeepers. Bootstrapping shapes smarter decisions: founders without outside capital often make fewer costly mistakes. Common rookie error: one small oversight in writing, packaging or distribution can make a book DOA. AI is acce