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

Mar 4, 2026

Ask episode

Chapters

Transcript

Episode notes

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: podcast@roguestartups.com
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: