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
RS347: How to Rank Any Brand In AI Results [not-audio_url] [/not-audio_url]

Duration: 47:34
This week on Rogue Startups, Craig chats with Mike Buckbee from Knowatoa about how AI is changing the game for brands. With tools like ChatGPT taking over the way we search and discover businesses, Mike breaks down what…
RS346: What 11 Years in SaaS Really Looks Like [not-audio_url] [/not-audio_url]

Duration: 48:49
In this episode of the podcast, Craig sits down with longtime entrepreneur Colin Bartlett, cofounder of StatusGator, to explore what it really takes to build, and sustain, a SaaS business over the long haul. With more th…
RS345: The State Of Search 2025 [not-audio_url] [/not-audio_url]

Duration: 18:27
- LLMs.txt article: https://www.quoleady.com/llm-txt-files/ - Craig's YouTube channel: https://youtube.com/@thecraighewitt
RS344: 12 Years to Overnight Success with Amar Ghose [not-audio_url] [/not-audio_url]

Duration: 47:27
What does it really take to lead a company for over a decade—and still be growing? In this episode, Craig chats with Amar Ghose, founder and longtime CEO of ZenMaid, about the challenges, lessons, and evolution that come…
A Caffeine Infused Diatribe [not-audio_url] [/not-audio_url]

Duration: 46:59
Hello, remember me? Sorry that it's been 6 weeks, but I'm back. In this episode I talk through what I've been up to recently, what's going on with Castos, with myself personally, and things I'm learning growing the busin…
RS342: SaaS Survival Mode - AI, Niches & Navigating Chaos [not-audio_url] [/not-audio_url]

Duration: 45:12
In this episode of Rogue Startups, Craig chats with Jesse Hanley, marketer, self-taught developer, and founder of Bento, a powerful email marketing platform for modern teams. With today’s economy in flux and global event…
RS341: Microconf 2025 Recap [not-audio_url] [/not-audio_url]

Duration: 17:48
Craig recaps his biggest takeaways from MicroConf 2025, reflecting on lessons in positioning, lead generation, conference ROI, and the power of going all in on what’s working. From tactical marketing insights to personal…
RS340: Is AI Killing SaaS w/ Tim Schumacher [not-audio_url] [/not-audio_url]

Duration: 43:00
In this episode of Rogue Startups, Craig sits down with founder and entrepreneur Tim Schumacher to discuss his insights on AI, the future of SaaS, and what makes a company successful. In 2001, Tim co-founded Sedo.com, th…
RS339: AI Skeptic, or Believer [not-audio_url] [/not-audio_url]

Duration: 47:49
In today’s episode, Craig chats with Anthony Eden from DNSimple about how they use AI in their businesses and their personal lives. As early skeptics of AI, they do a deep dive into what made them change their minds, wha…
RS338:  Balancing Your Use of AI with Aaron Francis [not-audio_url] [/not-audio_url]

Duration: 52:12
Ever wonder what's happening behind the scenes when your dev team says they're "leveraging AI"? As a non-technical founder, you don't need to understand every line of code, but knowing how AI is actually being used in yo…