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/ 

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Chapters

• (00:00:00) - Interview + Co-Host Chat
• (00:02:34) - Visit Annecy, France
• (00:02:51) - Living in France as an American
• (00:04:39) - Trump on Trade Wars and AI
• (00:05:04) - Bento CEO on Working With Customers
• (00:07:41) - What's the rest of the team like?
• (00:11:02) - How to Hire an AI-Inspired Team
• (00:16:46) - Bento's CEO on How Long Will He Run the Business?
• (00:18:55) - Bento CEO on Cash Exclusion
• (00:23:53) - WSJD: Business Cycle, Uncertain Future
• (00:27:15) - Have We Should Offer a Free tier?
• (00:33:03) - Bento vs. Mailchimp: How To Reach Out to
• (00:38:41) - Bento on Being a Utility Tool
• (00:40:24) - Bento on Collaboration and Its Impact
• (00:43:52) - Community and the AI of Business