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.

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

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:

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.

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.

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:

Email: [email protected]

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. 

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:

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.

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. 

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:

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.

Today, Craig chats with Jordan Gal from Rosie about starting a business centered solely on AI. While many of us use AI to help with our work tasks and streamline certain jobs, Jordan’s whole business is AI. They discuss how you and your customers can use AI, what it’s like to start a company right now, and what AI is doing to SaaS.

Rosie creates a new option for small businesses. Previously, the only way to handle phone calls during work hours was through voicemail or an answering service. Rosie offers a new option in that market: an AI can answer the phone for you and handle the tasks needed for these calls, whether it’s taking messages, sending messages out, or talking to clients.

Everything in technology is time-sensitive because tech improves and evolves so fast. Rosie shows us that AI can do much more than just answer questions, run some numbers, and analyze data. Whether you’re using AI to help your business run better, or if you’re creating the next AI tool, now is the time to embrace this technology.

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? Do you have any interesting or unique AI stories or experiences to share? Feel free to reach out to me:

On today’s episode of Rogue Startups, Craig continues his AI series with founder, marketer, and Claude-user Alison French. They discuss the hesitation creators feel when working alongside AI and what Alison did to overcome that hurdle. Since then, she’s taught herself how to use Claude.ai in her creative and professional work. AI is a tool that everyone has to learn how to use. 

Watch on YouTube

If you feel our podcast has benefited you and might benefit someone else, please share it with them. Also, if you have a chance, please give Rogue Startups a review on iTunes. We’ll see you next week!

Takeaways and Vision

Balancing the importance of human connection with the ability to express your individuality and be yourself is even more possible in this AI era. Adopting and embracing technology and AI in your personal and professional lives can help save you time and free up some creative energy for being social, innovative, and expressing yourself. AI will give you the time to do the work to open yourself up to having personal experiences.

Resources and Links from This Episode

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:

In today’s episode of Rogue Startups, Craig sits down with AI expert Dr. Stuart Grey to discuss how AI is transforming both his personal and professional life. Dr. Grey also shares how he educates his students and clients on AI applications. He believes AI will play a pivotal role in all of our futures, and while there may be hesitations, AI can be harnessed to create high-quality content and drive innovation.

Watch on YouTube

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.

Takeaways and Vision

AI is integrating into our daily lives and everyone needs to learn how to leverage this powerful technology to save time and enhance productivity. Whether you’re just starting or an established professional, understanding how to work alongside AI-powered tools is key to staying ahead in your career.

Resources and Links from This Episode

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: