Rogue Startups

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: Craig Hewitt Email: podcast@roguestartups.com

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 reflections, this episode delivers both strategic clarity and founder fuel.

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, the world's largest domain marketplace. Since selling the company, he’s been active as an Entrepreneur and/or Investor in various start-ups, such as Eyeo (makers of Adblock Plus), Ecosia, Hitfox, Aklamio, Miomente, PiwikPro, BasicThinking, Home, Zolar, Joblift, SaaS.group, and others.  Highlights from Craig and Tim’s conversation: The future of SaaS keeps founders up at night Using artificial intelligence to analyze feedback and company metrics for smarter decision-making How to make your data, and your customers' data, available across multiple platforms and environments What impact will AI and automation have on the economy and the future of work? Why are some in the SaaS industry still hesitant to adopt AI, and what are their fears? Key factors that drive business growth and longevity. Product-Market Fit vs Founder-Market Fit: Understanding the difference and why both matter. Starting a business at the intersection between climate tech and AI Remote work vs in-office culture: How the workplace dynamic is evolving in the age of digital transformation. Resources and Links Mention in This Episode: Tim on Twitter/X Tim on LinkedIn Email: tim@saas.group Sedo Zenloop  Day.ai  Fyxer 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 

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, what AI does for them, and how it might actually be holding people back. Like the internet, AI is a powerful tool people can use to make their lives better.  They also chat about what it’s like to raise kids as entrepreneurs. Has their influence improved or hindered their children’s lives? Not to mention, how do they balance their work life and personal life and is AI helping them with that balance? Anthony Eden is the creator and founder of DNSimple. He has been developing web applications since the early days of the web (1995) using Ruby, Erlang, Golang, and other languages. He used to publish a podcast called the Strong Businesses Podcast with Steven Bristol. He also published a mostly weekly podcast of progressive dance music over at theministerprime.com. He also produces tracks which can be found on SoundCloud. Highlights from Craig and Anthony’s conversation: What changed Anthony and Craig’s minds about AI How to, as an entrepreneur, leverage AI without just “chasing the trend” The personal and emotional impacts of running a business in this AI world What AI will do for the future of business and SaaS Training AI and what the “mistakes” teach you and your team “I have to have a little bit of fear in everything I do [as a founder].” Keeping customer data safe and secure What data is AI using to aid you with your business? “This kind of stuff is fantastic but, boy, does it make you lazy.” As an entrepreneur, how do you talk to your kids about careers after college? How is generative AI going to make our lives better? Takeaways and Vision: How do you take a non-native AI solution and adapt it to a solution for your customers, your team, and your business? As a founder and entrepreneur, how you use AI in your business is important. Not only do you have to pay attention to what information you are getting from AI, but how it is affecting your productivity overall.  Resources and Links from This Episode: DNSimple Anthony Eden, LinkedIn Anthony Eden, Twitter Anthony Eden, email: anthony@dnsimple.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  

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 your business is becoming essential. Today I'm sitting down with Aaron Francis, who pulls back the curtain on AI in development work. We'll explore the surprising differences between how veterans and newcomers in the field are using these tools, the common pitfalls teams fall into, and the unexpected ways AI is transforming how products get built. Whether you're trying to speak your developer's language or just want to ensure your company is using AI effectively, this conversation will give you the insights you need.   Highlights from this Episode: Are junior developers utilizing AI too much? Creating a balance between overusing AI and being a Luddite How Aaron uses Claude for “discrete” tasks Developers aren’t going away anytime soon Balancing the use of AI without depending too much on it Harnessing the power of AI for your business AI tools are both calming and scary for founders Aaron’s different uses for 01 Pro What AI can do versus what AI should do and undeniably human tasks Where to go to educate yourself about AI The importance of testing and checking AI work   Resources and Links from this Episode: Try Hard Studios: https://tryhardstudios.com/ Aaron Francis: https://x.com/aarondfrancis Reforge: https://www.reforge.com/profiles/brian-balfour SWYX: https://x.com/swyx https://www.youtube.com/@JeffSu https://www.youtube.com/@SkillLeapAI https://www.youtube.com/@MATGpod Email me: podcast@roguestartups.com Find me on Twitter:  https://twitter.com/TheCraigHewitt

Jordan Gal, founder of Rosie, discusses launching an AI-driven service that revolutionizes phone call management for small businesses. He emphasizes the need for non-technical CEOs to understand their customer's perspective. The conversation covers using AI to enhance user experience, strategies to avoid churn, and the importance of clear communication. They also touch on onboarding practices and the dynamics of customer acquisition. Jordan highlights the company's focus on genuine customer needs and the shift towards simplicity in tech solutions.

Join Alison French, a founder and marketer who specializes in AI tools like Claude.ai, as she dives into using AI to boost creativity and efficiency. She shares her journey overcoming initial hesitations to embrace AI, emphasizing its role as a collaborative partner. Discover how to fine-tune Claude's tone to fit your projects and transform your content creation process. Alison also discusses the balance between technology and personal connection, highlighting the importance of nurturing creativity while streamlining workflows.

In this engaging discussion, Dr. Stuart Grey, an AI expert and university educator, shares his insights on the transformative power of AI in everyday life and business. He talks about the balance of teaching technical skills with critical thinking in engineering education. The episode dives into practical AI tools for content generation and the importance of ethical considerations. Grey also reveals his AI Rules of Thumb, and emphasizes the need for human oversight in an increasingly automated world.

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 real ways they’re using AI in their businesses. If you’re interested in joining the conversation, hit me up (details below). But for now, here’s a breakdown of how I’m incorporating AI into my own work. Key Ways I’m Using AI in My Business Content Creation for Programmatic SEO Using OpenAI and Claude to create use case pages for Castos. Built a process to programmatically generate 100+ SEO landing pages using Google Sheets and templates. Example use case: Why Startups Should Start a Podcast for Thought Leadership. Custom GPT for YouTube Scripts Created a custom GPT workflow to script our Castos YouTube videos. Process: Provide a topic, feed it examples, and let GPT draft outlines and scripts. Outcome: High-performing, 90%-ready scripts I tweak and personalize. Building Free Marketing Tools Leveraging tools like Replit and Cursor to develop free tools for Castos (e.g., podcast name generator, social post creator). Focus: Engineering as marketing to drive traffic and lead generation. Documenting Internal Processes Using Loom to record workflows (e.g., triaging support tickets). Leveraging AI to convert videos into detailed step-by-step process documentation (aka playbooks). Automating Low-Level Tasks (Future Plans) Exploring tools like Make and Airtable for automating repetitive processes (e.g., email tagging, Slack notifications). Goal: Free up mental energy for high-value activities like sales, marketing, and strategy. Takeaways and Vision AI is transforming the way we work, and I’m all in on finding ways to integrate it into every aspect of my business. It’s not just about saving time; it’s about leveling up and creating systems that make the impossible possible. I’m inspired by the idea of building something like an 8-person, $10M business with AI at its core. That’s where I’m headed—and I want to bring you along. Resources and Links from This Episode Castos Free Tools: castos.com/tools VidIQ (for YouTube insights): vidiq.com Replit (for building free tools): replit.com Cursor (for coding support): cursor.com Loom (for recording processes): loom.com Email me: podcast@roguestartups.com Find me on Twitter: @TheCraigHewitt Want to Share Your AI Story? I’m looking for guests to share how they’re using AI in their businesses. If you’ve got some great examples or unique insights, reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com Let’s level up together!

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 fundamental strength and potential of your business. Episode Highlights Craig grades Castos (podcast hosting platform) across eight key criteria for evaluating SaaS businesses: 1. Pricing (6/10)- Core product (podcast hosting) averages $28/month - below ideal $50+ threshold- Production services start at $1,500/month- Enterprise clients pay tens of thousands annually- Mixed pricing model affects overall score 2. Churn (9/10)- Extremely low churn rate- Attributes success to: - WordPress integration- Premium pricing (no free tier) - Strong technical reliability 3. Payment Processing Integration (4/10)- Offers multiple monetization options: - Castos Ads - Castos Commerce - Donations - Paid subscriptions - Private podcasting- Limited adoption of direct monetization features- Most customers monetize indirectly through business growth 4. Switching Costs (6/10)- Technically easy to switch providers- High retention due to ongoing necessity- Perceived switching cost higher than actual 5. Technical Advantages- WordPress integration provides unique value- Core functionality similar to competitors- Important lesson: Customer needs often simpler than assumed 6. Expansion Revenue (3/10)- Limited expansion opportunities- Most customers stay at $19/month- Working to add upgrade opportunities- Identified as major growth limitation 7. Established Market Need (10/10)- Clear market position- Well-understood service category- Strong product-market fit 8. Customer Acquisition (6/10)- Success with content marketing, SEO, partnerships- Struggling with paid acquisition- Limited by low price point- Working on improving paid channels Key Takeaways - Overall Business Grade: B (maybe 80/100)- Growth Ceiling: Business could potentially double but unlikely to become a $50M/year company- Main Limitations: - Low initial price point ($19/month for most customers) - Limited expansion revenue - Restricted marketing channels due to unit economics Looking Forward Future episodes will mix personal insights about founding and running a business with interviews featuring successful founders.