Rogue Startups

- LLMs.txt article: https://www.quoleady.com/llm-txt-files/ - Craig's YouTube channel: https://youtube.com/@thecraighewitt  

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 from running a SaaS company for 12 years. From market leadership and internal conflict to personal growth and productivity, Amar shares candid insights into the realities of long-term entrepreneurship. Whether you're scaling a startup, feeling stagnant in your leadership role, or just wondering if AI is going to eat your SaaS lunch, this conversation delivers.   Highlights from Craig and Amar's conversation: Transitioning from following trends to becoming a category leader Navigating internal disagreements and managing tough decisions Running a "benevolent dictatorship"—and why that sometimes works How to deal with boredom, complacency, and staying sharp as a CEO The productivity paradox: what being "productive" means at the top Entertainment vs. distraction: protecting your focus How coaching reveals your blind spots (and helps you evolve) Staying out of cruise control—how to keep leveling up, year after year Is AI a threat to SaaS companies, or a tool for growth? Takeaways and Vision Longevity in SaaS isn’t about coasting. It’s about evolving. Amar Ghose proves that staying in the game for 12+ years means embracing discomfort, sharpening your focus, and leading with intention. Whether you're one year in or a decade deep, this episode is a reminder: real leadership isn’t about avoiding boredom, it’s about leveling up through it. Resources and Links from This Episode ZenMaid – Amar’s SaaS for maid service businesses Follow Amar on LinkedIn Rogue Startups Podcast Archive Connect with Craig on Twitter/X: @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  

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 business.  Towards the end, I share the lessons I learned from a recent 2-day Scaling Workshop with Alex and Leila Hormozi.  The event was great, and really reframed how I am thinking about the business, and about being a business owner.   My YouTube channel: https://youtube.com/@thecraighewitt - for sales, marketing, and founder-focused content like this.

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.