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Smart Bear Live

Jason Cohen 1 Episodes Aug 23, 2026

Smart Bear Live is a business therapy podcast hosted by Jason Cohen, also known as "A Smart Bear" online. He and a rotating co-host provide brutally honest advice to founders of real companies facing genuine puzzles and struggles. The show cuts to the heart of issues and helps rebuild with ideas, options, strategies, and decisions. It's like a therapy session for businesses.

Episodes

E03: Podsqueeze: Stuck at €16K/mo, workshopping how to restart growth Aug 23, 2026 9043 Tiago Ferreira and João Amaro bootstrapped their AI podcast-repurposing tool Podsqueeze from zero to €16K/mo in less than a year, but then watched it sit flat for two years despite more features, better SEO, and free trials.Cohost Craig Hewitt (Castos) and I dig into the real problem: the self-serve podcaster market is structurally brutal—most shows fade within months, so the product's va

E02: DropInBlog: Expanding from $1M ARR, workshopping how to enter a new market Aug 16, 2026 8057 DropInBlog's Jesse Schoberg has 2,000 happy customers, 2% monthly churn, a Bangkok-nomad life—and a growth curve that has plateaued. I and co-host Rob Walling tear into the real problem: a proven new cohort without a go-to-market plan. Two hours on pricing, positioning, AI/LLM visibility, the agency channel, ABM, and how to expand without breaking the business people already love. =======

E01: ScreenshotOne: Restarting growth at $32k/mo using both feelings and metrics Jul 23, 2026 7489 $32K MRR, 9% churn, flat growth, but we figured out a strategy for how to restart growth. The thought process behind the analysis and determining a strategy, not just knee-jerk answers. Subscribe to A Smart Bear on YouTube 📘 Pre-order my book! 📘 Dmytro runs a profitable screenshot-API SaaS: ~1,000 customers, $32K MRR, four years in — and dead flat. He wants to triple it to $100K MRR, so h

Smart Bear Live

Episodes

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