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
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Chapters
- (00:00:00) - Testing New Ideas
- (00:00:54) - Bento on Testing in AI Software
- (00:09:18) - How to Start a Startup: Plan Your Startup's Future
- (00:11:06) - Flows: Things are moving fast
- (00:16:18) - Reveal: Learning To Optimize Your Website With Nano Banana
- (00:21:45) - "It'll be hard to get a job in 2021."
- (00:22:12) - How's your team adapting to the AI revolution?
- (00:24:16) - Podcaster on the Future of Podcasting
- (00:27:23) - Shopify's AI Announcement
- (00:34:43) - Bento CEO on His Strategic Plan
- (00:38:12) - Gemini 3.8: Using AI to Make Better Design
- (00:43:08) - Cursor: We're Not Using a CMS
- (00:48:51) - What is the bottleneck in the WordPress vs. Blog?
- (00:50:57) - Have You Got Time for Side Projects?
- (00:54:34) - Custos vs. Riverside: How Big Is the Podcast Market
- (00:59:38) - How Castos is changing the way we edit videos
- (01:01:15) - Bob Dylan on His New Direction
