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

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

Author: RogueStartups 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
RS337: Building AI Native SaaS w/ Jordan Gal [not-audio_url] [/not-audio_url]

Duration: 48:06
Today, Craig chats with Jordan Gal from Rosie about starting a business centered solely on AI. While many of us use AI to help with our work tasks and streamline certain jobs, Jordan’s whole business is AI. They discuss…
RS336: Claude Project Deep Dive with Alison French [not-audio_url] [/not-audio_url]

Duration: 47:43
On today’s episode of Rogue Startups, Craig continues his AI series with founder, marketer, and Claude-user Alison French. They discuss the hesitation creators feel when working alongside AI and what Alison did to overco…
RS335: Evaluating AI Model Performance with Stuart Grey [not-audio_url] [/not-audio_url]

Duration: 47:06
In today’s episode of Rogue Startups, Craig sits down with AI expert Dr. Stuart Grey to discuss how AI is transforming both his personal and professional life. Dr. Grey also shares how he educates his students and client…
RS334: How AI Saves Me 10 Hours A Week [not-audio_url] [/not-audio_url]

Duration: 15:51
Today, I’m kicking off a series on AI—how I’m using it personally and professionally to grow my business, make life easier, and operate at a higher level. Over the next few episodes, I’ll be chatting with folks about the…
RS333: Grading My Business (and yours!) [not-audio_url] [/not-audio_url]

Duration: 22:03
In this New Year's Eve 2024 episode, we dive into a framework for evaluating SaaS businesses across eight crucial criteria. Instead of doing a typical year-in-review or making predictions, we explore how to assess the fu…
RS332: Competing with Stripe and Hubspot (ft. Geoff Roberts) [not-audio_url] [/not-audio_url]

Duration: 39:14
Hey everyone! Just had an awesome chat with Geoff Roberts from Outseta (outseta.com). They're doing something pretty wild - basically smashing together Stripe and HubSpot into one platform for subscription businesses. Ho…
RS331: I'm Still Here... [not-audio_url] [/not-audio_url]

Duration: 9:23
After a 2+ month hiatus, we're back! Watch on YouTube Sorry for the pause in episodes, but thank you for tuning in this week. In this episode I talk through why the forever long break in the podcast, what I've learned in…
RS330: Product-Led Playbook with Wes Bush [not-audio_url] [/not-audio_url]

Duration: 47:52
Wes Bush is a leading authority on product-led growth (PLG) and is here to guide Craig through the playbook for implementing product-led strategies in your business. This episode is invaluable for entrepreneurs eager to…
How To Hire For Growth [not-audio_url] [/not-audio_url]

Duration: 14:20
In this episode of Rogue Startups, I dug into several pressing questions from the community. From knowing when to pull the plug on a marketing channel to the debate around hiring for support versus sales, we covered grou…
RS328: Are you Productive or Effective as a founder? [not-audio_url] [/not-audio_url]

Duration: 14:27
Running a business is both incredibly rewarding and exhausting. Over the years, I’ve experienced highs of motivation and productivity, but I’ve also hit those low points, battling burnout and loneliness. In this post, I…