Podcast Episodes

Episode 806 | Bootstrapping Missive to $8M ARR Over 10 Years

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Can a small team really bootstrap to $8M ARR in a crowded SaaS market?

In this episode, Rob Walling chats with Philippe Lehoux about how…

Published on 9 hours ago

Episode 805 | Gatekeeping vs. Paying Dues, Raw Material, and Surrounding Yourself with the Right People (A Rob Solo Adventure)

How much does your startup idea matter compared to your execution?

In this solo episode, Rob Walling covers several founder-focused topics: the difference between gatekeeping and paying your dues, wh…

Published on 1 week ago

Episode 804 | Positioning, Inventing a Category, Marketing Globally, and More Listener Questions (A Rob Solo Adventure)

Can bootstrapped founders really invent a new category with AI or is it a trap?

In this solo episode, Rob Walling answers a fresh batch of listener questions covering SaaS marketing, global expansion…

Published on 2 weeks ago

Episode 803 | 8 Key Takeaways from MicroConf Europe 2025

What's it really like to attend MicroConf?

In this episode, Rob Walling and Laura Sprinkle, founder of Rootabl, recap MicroConf Europe 2025 in Istanbul. They discuss the MicroConf vibe, standout talk…

Published on 3 weeks ago

Episode 802 | Marketing Not Scaling, Where to Publish Content, and More Listener Questions (A Rob Solo Adventure)

Where’s the best place to publish if you’re starting content from scratch?

In this episode, Rob Walling flies solo, answering your questions on marketing and audience building. He covers what to do w…

Published on 4 weeks ago

Episode 801 | Competing Against Incumbents, Technical Co-Founders, Trademarks, and More Listener Questions with Derrick Reimer

Can churn ever be good in SaaS?

In this episode, Rob Walling is joined by fan favorite Derrick Reimer for a listener Q&A. They break down what it takes to compete with well-funded incumbents, how to …

Published on 1 month ago

Episode 800 | The 12 Commandments of Startups for the Rest of Us

What if you could get all 15 years of this podcast bundled up into one episode? 

In episode 800, Rob Walling goes solo for a special milestone installment of Startups For the Rest of Us. He covers th…

Published on 1 month, 1 week ago

Episode 799 | TinySeed Tales s5e6: $500k ARR!

What's next for OutboundSync?

In the Season 5 finale of TinySeed Tales, Rob Walling talks with Harris Kenny as OutboundSync blows past $500k ARR. Harris shares the wins and struggles of getting here,…

Published on 1 month, 2 weeks ago

Episode 798 | Lessons From 10 Years of SaaS Growth Without a Hockey Stick

How do you bootstrap a SaaS to $1 million+ ARR?

In this episode, Rob Walling chats with Colin Bartlett about how he and his co-founder Andy transformed a side project monitoring tool into a seven-fig…

Published on 1 month, 2 weeks ago

Episode 797 | TinySeed Tales s5e5: Should I Raise More Funding?

OutboundSync just hit $35k MRR—but the decisions are only getting harder. 

In this episode of TinySeed Tales, Rob Walling and Harris Kenny dive into the messy middle of SaaS growth, where every oppor…

Published on 1 month, 3 weeks ago