
Episode 839 | The Journey Growing Help Scout to $35M ARR
What happens when a bootstrapper at heart raises $28 million and spends the next decade living with that decision? In this episode, Rob Wall...
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What happens when a bootstrapper at heart raises $28 million and spends the next decade living with that decision? In this episode, Rob Wall...

What do 15 brand-new TinySeed founders have in common? In this solo episode, Rob Walling shares six key takeaways from the most recent TinyS...

How does a founder actually learn the skill of product? In this episode, Rob Walling talks with Ruben Gamez of SignWell and Bidsketch to ans...

Is your SaaS actually protected from AI disruption, or are acquirers walking away without even looking? In this episode, Rob Walling talks w...

Are you using AI in your marketing because it's actually good, or just because it's fast? In this episode, Rob Walling sits down with Taylor...

Is AI actually making your build-measure-learn cycle faster, or just making your work more average? In this episode, Rob Walling talks with...

What do Nobel Prize winners and successful bootstrappers have in common? In this solo episode, Rob Walling shares the story of how a TinySee...

How do you leave a $400K salary to go all in on your business? In this solo episode, Rob Walling cranks through a backlog of listener questi...

Should your first customer pay you, or get your product for free? In this episode, Rob Walling answers listener questions on charging custom...

What were the highlights and takeaways from MicroConf? In this episode, Rob Walling and Derrick Reimer recap MicroConf US 2026 in Portland,...

Can AI really handle product decisions for your SaaS? In this solo adventure, Rob Walling revisits the core four SaaS skills and breaks down...

Is your product actually a SaaS? In this episode, Rob Walling tackles listener questions about what really qualifies as SaaS (and where he d...

What would it mean for you to leave 60 or 70% of your company's value on the table when you sell? In this episode, Rob sits down with Einar...

How do you find someone who thinks like an owner, not just a task-doer? In this episode, Rob digs into a batch of listener questions about t...

What happens when AI starts competing with your open source business? In this episode, Rob Walling sits down with Adam Wathan, co-founder of...

What do you do when a collaborator takes your idea and builds a competing product? In this episode, Rob Walling is joined by fan favorite Jo...

Is AI really killing B2B SaaS, or is it just subscription software by another name? In this Hot Take Tuesday, Rob Walling, Einar Vollset, an...

Should you build your SaaS with no-code tools, or is AI coding the better path forward? In this episode, Rob is joined by fan favorite Derri...

Is founder-led marketing right for your SaaS, or just a distraction? In this episode, Rob Walling sits down with Jay Clouse, founder of Crea...

When do you finally quit your day job and go all-in on your startup? In this solo episode, Rob Walling answers listener questions about when...