Shopify

E03 w/ Craig Hewitt: Restarting growth after stuck at €16k/mo

Aug 23, 2026 · 2:30:43

On Smart Bear Live, Jason Cohen and Castos founder Craig Hewitt tell Podsqueeze founders Tiago Ferreira and João Amaro that their two-year plateau at €16K/mo is the self-serve podcaster market, not the product: shows fade, while agencies and media companies barely churn. The tool hit €14K in six months with 15–20% monthly churn; SEO and features didn't move the curve. Cohen says 'too expensive' is never the real churn reason; their Portuguese clients accepted a 5x increase without blinking—far from the ceiling. He advises pricing to value, positioning it as an all-in-one pipeline, and selling to agencies—clients paying €400–500/month stayed a year. Abroad, deals died for lack of priority; financially a sideways business is worth little—maybe 1x revenue—unless an agency buys it strategically.

E02 w/ Rob Walling: $1M ARR, how to expand into a new market

Aug 16, 2026 · 2:14:17

Jesse Schoberg's DropInBlog has 2,000 customers, 2% monthly churn, and a plateaued growth curve; hosts Jason Cohen and Rob Walling argue DropInBlog should deliberately push into BigCommerce businesses and agencies serving them. Schoberg says enterprise visitors were 5% of traffic but converting zero; after adding invoicing, audit logs, and white-glove migrations, $399/$499 plans began selling. They tell him to market engineers and marketers separately, pitch marketers on AI/LLM visibility as job security, use ads to learn messaging not just ROI, and build an agency channel because one agency can bring multiple clients. They also challenge his Laravel focus, argue BigCommerce is where the fish are, and advise giving each initiative an owner, separate metrics, and company-wide alignment.