February 17, 2026
Rob Walling tackles when to quit your day job, AI feasibility risk, co-founder equity splits, and managing high-churn pricing plans.
February 10, 2026
Rob Walling discusses QSBS for C-Corps, why SaaS exit multiples favor growth over profit, and how developers can learn marketing effectively.
February 3, 2026
What does it take to succeed? Rob Walling and his brother Russ discuss mindset, overcoming perfectionism, and the "Armageddon beer" principle.
January 27, 2026
Unicorn founder Jason Cohen on bootstrapping, niching to win, building brand through execution, and navigating the AI startup landscape.
January 20, 2026
Develop an 'editorial eye' for quality, be persistent with goals (not methods), and use focus to win. A founder's guide to key traits.
January 13, 2026
Your day job is an entrepreneurial training ground. Learn how roles from courier to developer can teach you vital founder skills.
January 6, 2026
Bootstrapped founder Laura Roeder explains how her lean SaaS, Paperbell, beat a $10M venture-backed competitor by avoiding common VC-funded pitfalls.
December 30, 2025
Rob Walling reviews his (mostly wrong) 2025 tech predictions, discusses key SaaS concepts, and shares bold forecasts for SaaS and AI in 2026.
December 23, 2025
Rob Walling shares insights from TinySeed's 7-year journey, funding 210+ SaaS startups. Key trends: the rise of AI and vertical SaaS.
December 16, 2025
Rob Walling discusses SaaS retention metrics, when to delegate core skills like sales & product, and the founder-market-product success formula.
December 9, 2025
Derrick Reimer on AI coding stacks, balancing speed vs polish, startup risk in the AI era, and practical security tips for founders.
December 2, 2025
Castos founder Craig Hewitt on his 100 Days of AI project, top AI tools beyond ChatGPT, and his pivot to building a new AI-powered product.
November 25, 2025
Navigating founder dilemmas: when to push, sell, or diversify a plateaued biz. Plus, timing compliance, balancing life, & why IP isn't the key.
November 18, 2025
Master the 'Core Four' of SaaS: Sales, Marketing, Product, & Development. Rob Walling answers questions on co-founders and enterprise deals.
November 11, 2025
How Missive bootstrapped to $8M ARR in a crowded market by respecting email, leveraging competitor SEO, and staying horizontal.
November 4, 2025
This episode covers gatekeeping vs. paying dues, refining raw talent with hard work, and why winning founders support others' success.
October 28, 2025
Rob Walling tackles key startup dilemmas: Should you go vertical or horizontal? Can bootstrappers create new categories? Plus, overcoming launch anxiety.
October 21, 2025
Rob Walling and Laura Sprinkle recap MicroConf Europe 2025, sharing 8 key takeaways on AI, growth, and community for bootstrapped founders.
October 14, 2025
This episode covers management buyouts, scaling marketing beyond plateaus, continuous product validation, and why you should own your content platform.
October 7, 2025
Rob Walling & Derrick Reimer tackle listener questions on competing with funded startups, pivoting, finding co-founders, and managing churn.
September 30, 2025
Rob Walling shares his 12 commandments for bootstrapped founders, covering nuance, marketing, decision-making, and founder psychology.
September 25, 2025
OutboundSync founder Harris Kenny on surpassing $500k ARR, delaying a funding round, and aiming for $1M with unconventional marketing.
September 23, 2025
The 10-year journey of StatusGator from a side project to a 7-figure SaaS. Learn how focus, SEO, and product evolution created a category leader.
September 18, 2025
Outbound Sync hits $35k MRR and profitability, but founder Harris Kenny faces a new challenge: to bootstrap or raise funding for the next phase?
September 16, 2025
Rob Walling debunks founder myths: marketing is complex (Dunning-Kruger), you can't just build it, and not all growth paths are viable.
