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

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

Author: RogueStartups 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
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…
RS357: I Got Hacked [not-audio_url] [/not-audio_url]

Duration: 44:26
This week on the Rogue Startups, Craig gets roasted. He brought in experienced software engineer Brandon Hancock after building the AI-powered SaaS app Outlier largely through “vibe coding,” so Brandon could audit the en…
RS356: When to Pivot, When to Push w/ Jesse Hanley [not-audio_url] [/not-audio_url]

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 develo…
RS355: Code Velocity and the Future of SaaS [not-audio_url] [/not-audio_url]

Duration: 58:05
What does it mean to be a SaaS founder in a world where AI can build features faster than we ever could? In this conversation, Craig sits down with Arvid Kahl to unpack the shifting reality of software, competition, and…
RS354: The State Of Podcasting Heading Into 2026 [not-audio_url] [/not-audio_url]

Duration: 41:22
Craig is back! Today, he welcomes fellow podcaster Colin Gray back to the podcast. They dive into the ever-evolving world of podcasting, reflecting on how much the landscape has shifted over the last decade and what peop…
RS353: Is This the Last Organic Marketing Channel [not-audio_url] [/not-audio_url]

Duration: 50:57
In today’s episode, Craig sits down with SaaS founder and entrepreneur Brian Casel to talk about the future of software and AI. With years of experience building and growing SaaS companies, Brian shares his perspective o…
RS352: AI Killed Traditional Marketing – Here's What's Next [not-audio_url] [/not-audio_url]

Duration: 49:33
Ross Simmonds, founder of Foundation Marketing, has built a reputation for helping ambitious SaaS and B2B brands stand out online with data-driven growth strategies. In this episode, Craig sits down with Ross to dive int…
RS351: Why Brands Fail on Reddit [not-audio_url] [/not-audio_url]

Duration: 45:05
Today on the podcast, Craig sits down with Reddit marketing expert Paul Xue to explore how brands can tap into one of the internet’s most engaged and skeptical communities. Reddit can be a tough nut to crack, but when ap…
RS349: Ranking In ChatGPT with Devesh Khanal [not-audio_url] [/not-audio_url]

Duration: 1:03:42
Today on Rogue Startups, Craig sits with Devesh Khanal from Grow and Convert to talk about how to get your brand showing up at the top of search results in LLMs. They dive deep into the world of AI SEO—covering everythin…