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 (youtube.com/@asmartbear)
📘 Get my book (hiddenmultipliers.com) 📘
My bio + 20 years of articles (longform.asmartbear.com)
Twitter (twitter.com/asmartbear) | LinkedIn (linkedin.com/in/jasoncohen)
STARRING TIAGO FERREIRA & JOÃO AMARO
Podsqueeze (podsqueeze.com)
Tiago's podcast, Indie Founder (podcasts.apple.com/us/podcast/indie-founder/id…)
Twitter (twitter.com/wbetiago) | LinkedIn (linkedin.com/in/tiago-ferreira-48562095)
Twitter (twitter.com/JOAOTHA) | LinkedIn (linkedin.com/in/jo%C3%A3o-amaro-62446a4a)
WITH COHOST CRAIG HEWITT
Castos (castos.com)
More About Craig (craighewitt.com)
Rogue Startups podcast (roguestartups.com)
Twitter (twitter.com/thecraighewitt) | LinkedIn (linkedin.com/in/craig-hewitt-78386a66)
REFERENCED IN THIS EPISODE
"Pricing determines your business model" (longform.asmartbear.com/pricing-determines-you…)
"How repositioning a product allows you to 8x its price" (longform.asmartbear.com/more-value-not-save-mo…)
TIMESTAMPS

• () - Meet the founders: bootstrapped to 16K, then stuck for two years

• () - Riding the GPT wave to 14K, then two flat years

• () - Podcast fade: why most customers quit within months

• () - Why 'too expensive' is never the real reason they cancel

• () - The Portugal B2B win, and why it won't travel abroad

• () - Enterprise vs. just a big customer: Joe Rogan isn't enterprise

• () - The 5x price test: they raised it and nobody blinked

• () - The Shopify model: how brutal churn can still win

• () - Charge for what grows as the customer grows

• () - Selling to agencies: why the demos never close

• () - Why enterprises take the meeting, then never buy

• () - The all-in-one bet: good enough beats best-in-class

• () - A homepage that's a mess because it talks to everyone

• () - The 500K offer they turned down: sell or double down?

• () - AI should kill the busy work, not make the content

• () - What your SEO traffic is actually worth

• () - Stuck in a bad market, and the path to a better one

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

Kapitelklicken springt direkt hin

Shownotes