RS356: When to Pivot, When to Push w/ Jesse Hanley

RS356: When to Pivot, When to Push w/ Jesse Hanley

From Rogue Startups by RogueStartups

March 4, 2026 · 1h 2m

About this episode

Craig and Jesse Hanley discuss the challenges and strategies for SaaS entrepreneurs in the evolving tech landscape influenced by AI.

In this episode of Rogue Startups, Craig sits down with Jesse Hanley, founder of Bento, for a wide-ranging conversation about building and growing SaaS businesses in the age of AI. From vibe coding and AI-assisted development workflows to product strategy, business ceilings, and the existential shifts happening across the tech landscape, Jesse and Sandy share candid insights from their own experiences as founders navigating a rapidly changing environment. If you're a bootstrapped founder, indie hacker, or SaaS entrepreneur trying to figure out how to stay relevant and move fast, this one's for you. Highlights from Craig and Jesse’s conversation: Testing and QA are still the unglamorous bottleneck nobody talks about enough The founders who stay close to the code sleep better at night Opus 4.5 in Cursor is the closest thing to having a full dev team on speed dial Build your foundation like a brick house, and everything else can be Play-Doh™ AI is making founders fall back in love with parts of their business they used to dread Shopify can now build custom apps on demand, and that should make plugin developers nervous If your whole product is basically one feature, it might be time…

People in this episode

Host: Craig

Guest: Jesse Hanley

Topics covered

  • SaaS businesses
  • AI development
  • product strategy
  • founder experiences
  • bootstrapped entrepreneurship
  • tech landscape changes

Keywords

  • SaaS
  • AI
  • entrepreneurship
  • product development
  • founder insights
  • bootstrapping
  • tech disruption

Mentioned in this episode

Organizations: Bento, Shopify

Products: Opus 4.5, Cursor, Play-Doh™

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