RS342: SaaS Survival Mode - AI, Niches & Navigating Chaos

RS342: SaaS Survival Mode - AI, Niches & Navigating Chaos

Author: Craig Hewitt April 23, 2025 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 events adding more pressure, Craig and Jesse dive into what it really means to run and grow a SaaS business in 2025. They explore how entrepreneurs can protect their businesses and families in turbulent times, why niching down is more important than ever (but only for some), and how AI is transforming both Bento and Craig’s own company, Castos. From global living experiences to making tough decisions about free tiers, this episode is packed with honest insights, practical advice, and a few spicy takes on the future of SaaS. Highlights from Craig and Jesse’s conversation: Living and working in Japan, France, Australia, and the US: cultural and business differences Bento’s vision and how they are navigating economic uncertainty Knowing when to bring in experts (and when to trust your gut) How Bento is integrating AI—and how it’s driving real results for users Behind the scenes at Castos: using AI to boost productivity and creativity Are free plans a growth hack or a trap for SaaS companies? Marketing smarter: finding your ideal customers in a crowded market To niche or not to niche? What to do if your product is a Swiss Army knife If you’re a SaaS founder, bootstrapped entrepreneur, or just love behind-the-scenes looks at real businesses navigating real challenges, this episode is for you. Resources and Links from This Episode Jesse Hanley on Twitter/X: https://x.com/jessethanley  Bento: https://bentonow.com/  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:

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…