The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Startups & Founders/Cash Machines
Cash Machines artwork

Rob Walling’s 20 Year Master Plan

Cash Machines · 2025-05-15 · 33 min

0:00--:--

Topics in this episode

B2Btom huntconfessions of a b2b entrepreneurconfessionsb2b marketer

Episode notes

In this episode of Confessions of a B2B Entrepreneur, host Tom Hunt chats with the legendary Rob Walling. A true veteran of the SaaS bootstrapping world, Rob shares insights from his two decades in the game, from building and selling Drip, starting the influential MicroConf community and the TinySeed accelerator, to hosting the 'Startup for the Rest of Us' podcast. They discuss the power of compounding effort, the crucial lesson of following market feedback, iterating your approach based on what the market wants, and the journey of building multiple successful ventures without relying on traditional VC. Rob reflects on the lessons learned over twenty years, offering invaluable perspective for any entrepreneur looking to build sustainable, long-term growth.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • 183: Why Trusted Data is the New AI Moat (w/ Rick Kranz @ AI Marketing Automation Lab)Move The Needle · on B2B91 / 100
  • Pipeline Gives Permission to Invest Big on Brand with Jennifer JohnsonThe B2B CMO Podcast with Jon Miller and Sydney Sloan · on B2B74 / 100
  • Step Zero: What Comes Before Every AI Rollout in B2BB2B Commerce UnCut Podcast · on B2B55 / 100
  • 74: Six inches high and risingOur B2B SaaS Journey · on B2B54 / 100
  • How Marketing Attribution Misses Trade Show LeadsMarketing Analytics with Fexingo · on B2B

More from Cash Machines

All episodes →
  • How to Build a B2B Podcast That Drives Pipeline with Tom Hunt (Growth Activated)82 / 100
  • The "OnlyFans" Cash Machine56 / 100
  • The "Flying V Group" Cash Machine77 / 100
  • $4.5m ARR, $0 Raised: Tom Hunt on Building Fame (Getting to Aha!)74 / 100
  • The "Software Finder" Cash Machine70 / 100
Explore the best B2B Startups & Founders podcasts →
All Cash Machines episodes →