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

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