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

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: [e-mail]
• Find me on Twitter: @TheCraigHewitt

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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: [e-mail]

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