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

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

Author: Craig Hewitt March 4, 2026 Duration: 1:02:06
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: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com 

Behind every new company is a story, and Rogue Startups digs into the real ones-the messy, uncertain, and exhilarating paths founders actually walk. This isn't about polished success tales; it's a candid look at the day-to-day grind of building a business from the ground up. You'll hear directly from entrepreneurs in the thick of it, along with seasoned experts who specialize in the crucial engines of growth: sales, marketing, and product development. Conversations focus on practical tactics, particularly around scaling productized services and SaaS offerings, exploring the real "how" behind their growth hacking strategies. The value of this podcast lies in that shared experience-hearing how others navigate the very obstacles you might be staring down, and learning what moves actually led to a win. It’s for anyone who prefers the unvarnished truth of entrepreneurship over theory, offering a sense of camaraderie and a toolbox of ideas drawn from the front lines. Tune in for authentic dialogue that skips the fluff and gets straight to the challenges and victories of building something new.
Author: Language: en-us Episodes: 50

Rogue Startups
Podcast Episodes
RS367: How to Hire in the AI Era [not-audio_url] [/not-audio_url]

Duration: 48:35
Do you need a team to build a successful company these days? On this episode of Rogue Startups, host Craig Hewitt (Castos) and co-host Colin Gray (Alitu and The Podcast Host) tackle one of the biggest questions facing fo…
RS366: When (and how) To Pick a Co-Founder [not-audio_url] [/not-audio_url]

Duration: 41:23
Should you build your next company alone, or find a co-founder? It's a question that has no easy answer, and AI is making it even more complicated. If one person can now build, market, and operate far more of a business…
RS365: Marketing that Actually Works Today [not-audio_url] [/not-audio_url]

Duration: 48:45
What happens to marketing when AI can create almost unlimited content, build software in days, and make it easier than ever for anyone to compete? In this episode of Rogue Startups, Craig Hewitt and co-host Colin Gray di…
RS364: Think Less, Do More [not-audio_url] [/not-audio_url]

Duration: 48:10
AI has made building software dramatically easier. But if everyone can build a product, what happens to SaaS? In this episode of Rogue Startups, Craig Hewitt is joined by co-host Colin Gray for a wide-ranging conversatio…
RS363: Why Talking to AI About Your Business Is Dangerous [not-audio_url] [/not-audio_url]

Duration: 32:53
While we weren’t looking, AI has quietly embedded itself into the coaching world. Today Craig sits down with new cohost Colin Gray, founder of Alitu and The Podcast Host, to unpack the current state of the industry. They…
RS362: Hidden Multipliers with Jason Cohen [not-audio_url] [/not-audio_url]

Duration: 50:43
What happens when AI changes the rules of building a software company? According to Jason Cohen, the answer isn't to predict the future. It's to build around things that remain valuable no matter how technology changes.…
RS361: Lessons Learned Selling A Business [not-audio_url] [/not-audio_url]

Duration: 46:24
Selling a business isn't just about timing the market. It's about knowing yourself. In this episode of Rogue Startups, Craig Hewitt sits down with Colin Gray, founder of Alitu and The Podcast Host, to discuss what it's r…
RS360: Kill the Hippo [not-audio_url] [/not-audio_url]

Duration: 43:39
If you're building a SaaS company, one of the hardest questions you'll face isn't how to build a product. It's what to build next. In this episode of Rogue Startups, Craig Hewitt talks with Steve McLeod, founder of Featu…
Huge Work (and life) Updates [not-audio_url] [/not-audio_url]

Duration: 14:53
After an almost 5 month break from the podcast, I'm Back! In this episode I talk through updates with me, Castos, my coaching business, and where the podcast is headed into the future. Spoiler alert...i'm getting a new c…
RS358: Your Design Sucks [not-audio_url] [/not-audio_url]

Duration: 54:07
In this episode, Craig sits down with Francois Brill, Head of Product at Castos and longtime design collaborator, for an honest and entertaining conversation about what it really takes to build great-looking products in…