Startups For the Rest of Us

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Episodes

Date Title & Description Contributors
2024-11-19

  Episode 740 | My New Book! The Entrepreneur's Guide to Selling Your Business Without Regret

In episode 740, Rob Walling speaks with Dr. Sherry Walling about their new book, "Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret." They explore the emotional, psychological, and practical aspects of selling a business, ...
  Rob Walling author
2024-11-12

  Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

In episode 739, Rob Walling interviews Andy Kim, co-founder of Trotto, about his unique journey into SaaS. Andy shares how “go links” work, and why they are so valuable for internal, enterprise use despite their relative obscurity. They also explore th...
  Rob Walling author
2024-11-05

  Episode 738 | Encouraging Word of Mouth, Educating a Market, and More Listener Questions (A Rob Solo Adventure)

In episode 738, join Rob Walling for a solo adventure as he answers listener questions. He explores how to target larger, enterprise deals after achieving product-market fit, and why word of mouth marketing can be great, yet is tricky to control. Rob a...
  Rob Walling author
2024-10-29

  Episode 737 | Key Takeaways from MicroConf Europe 2024 (With Derrick Reimer)

In episode 737, Rob Walling is joined by Derrick Reimer to recap the experience from MicroConf Europe 2024 in Dubrovnik. They discuss the differences between MicroConf US and MicroConf Europe, some small programming tweaks over the years, and they revi...
  Rob Walling author
2024-10-22

  Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

In episode 736, join Rob Walling as he answers some later-stage listener questions in another solo adventure. He discusses common pitfalls in delegation, transitioning from one-time transactions to SaaS models, and when it makes sense to target multipl...
  Rob Walling author
2024-10-15

  Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)

In episode 735, join Rob Walling for a solo adventure where he categorizes the different levels of SaaS platform risk. He introduces a framework with three key factors: Replacement, Customer Concentration, and Lead Flow. Rob then defines eight levels o...
  Rob Walling author
2024-10-08

  Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

In episode 734, Rob Walling interviews Ian Landsman, founder of HelpSpot, about his 20-year bootstrapper journey. They discuss Ian's transition from on-prem software to SaaS, the challenges and benefits of each, and the early days of building the busin...
  Rob Walling author
2024-10-01

  Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)

In episode 733, join Rob Walling for a solo adventure where he covers several topics. In this episode he differentiates between good and bad distractions, weaknesses versus blind spots, and shares personal experiences of struggle. He concludes with act...
  Rob Walling author
2024-09-24

  Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

In episode 732, Rob Walling interviews Jeff, a mostly anonymous and retired founder, about his mostly bootstrapped business and subsequent exits. Jeff shares how he started the company in 2003 and how he persevered in the early, lonely years to achieve...
  Rob Walling author
2024-09-17

  Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)

In episode 731, join Rob Walling and Derrick Reimer as they tackle some more advanced listener questions. They discuss delegation and giving up areas of control as a founder, including examples from their time together at Drip. Derrick describes how he...
  Rob Walling author