EPISODE · Mar 4, 2026 · 1H 2M
RS356: When to Pivot, When to Push w/ Jesse Hanley
from Rogue Startups · host RogueStartups
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] 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
What this episode covers
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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RS356: When to Pivot, When to Push w/ Jesse Hanley
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