Rogue Startups

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

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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 to rethink things
  • Sometimes the ceiling you're hitting is the category, not your effort
  • The best side projects either pay for themselves immediately or swing for the fences
  • Building through AI disruption takes the same stubborn optimism it took to survive COVID
    • Resources and Links from This Episode
      • Jesse Hanley: https://jessehanley.com/ 

        • Connect with Jesse on LinkedIn: https://www.linkedin.com/in/jessehanley/ 

          • Bento:  https://bentonow.com/ 
          • Castos Free Tools: castos.com/tools
          • Email me: [email protected] 
          • Find me on Twitter: @TheCraigHewitt

            • If you feel like Rogue Startups has benefited you, and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. 

            Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me:

            • Twitter: @TheCraigHewitt
            • LinkedIn: Craig Hewitt
            • Email: [email protected] 
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