In this episode, Jeremy Toeman sits down with “serial marketer” David Berkowitz: From Teaching to Marketing Entrepreneur. David shares how he went from teaching aspirations to building and selling multiple marketing communities and agencies. You’ll hear how he:

* Tested community ideas on a shoestring budget and how he recruited 100 members overnight with under $100, one LinkedIn post, and a Google Form

* Applied an “MVP first” mindset to career pivots, writing the resume he wanted five years out and reverse-engineering his steps

* Embraced a “controlled fall” approach to uncertainty, leaning into small bets instead of overplanning

* Spun AI Marketers Guild into its own brand and why positioning matters when you scale

Tune in for a candid look at a journey that proves you don’t need a perfect plan to become a marketing entrepreneur, just a willingness to test, learn, and iterate.

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