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

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 value fades with them—and the real money is up-market, with agencies and media companies who barely churn. A candid working session including: - why "too expensive" is never the real churn reason - pricing to value - the 5x price test that proved they're nowhere near the ceiling - enterprise vs. just-big customers - positioning an all-in-one tool - what a plateaued "sideways" business is actually worth when someone offers to buy it ME ME ME!!! Subscribe on YouTube 📘 Get my book 📘 My bio + 20 years of articles Twitter | LinkedIn STARRING TIAGO FERREIRA & JOÃO AMARO Podsqueeze Tiago's podcast, Indie Founder Twitter | LinkedIn Twitter | LinkedIn WITH COHOST CRAIG HEWITT    Castos More About Craig Rogue Startups podcast Twitter | LinkedIn REFERENCED IN THIS EPISODE "Pricing determines your business model" "How repositioning a product allows you to 8x its price" TIMESTAMPS (00:00) - Meet the founders: bootstrapped to 16K, then stuck for two years (03:09) - Riding the GPT wave to 14K, then two flat years (09:03) - Podcast fade: why most customers quit within months (20:26) - Why 'too expensive' is never the real reason they cancel (26:50) - The Portugal B2B win, and why it won't travel abroad (34:35) - Enterprise vs. just a big customer: Joe Rogan isn't enterprise (49:43) - The 5x price test: they raised it and nobody blinked (57:33) - The Shopify model: how brutal churn can still win (01:03:40) - Charge for what grows as the customer grows (01:14:40) - Selling to agencies: why the demos never close (01:20:53) - Why enterprises take the meeting, then never buy (01:37:48) - The all-in-one bet: good enough beats best-in-class (01:52:07) - A homepage that's a mess because it talks to everyone (01:55:45) - The 500K offer they turned down: sell or double down? (02:02:16) - AI should kill the busy work, not make the content (02:18:42) - What your SEO traffic is actually worth (02:26:22) - Stuck in a bad market, and the path to a better one