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:

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.

Content Creation for Programmatic SEO

Custom GPT for YouTube Scripts

Building Free Marketing Tools

Documenting Internal Processes

Automating Low-Level Tasks (Future Plans)

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.

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:

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.

Hey everyone! Just had an awesome chat with Geoff Roberts from Outseta (outseta.com). They're doing something pretty wild - basically smashing together Stripe and HubSpot into one platform for subscription businesses. How cool is that?

Quick Hits:
- Outseta is an all-in-one platform handling payments, auth, CRM, email, and help desk
- They've got this unique setup where everyone makes $210k/year (pro-rated) and can work 1-5 days a week
- Took them 4 years to really nail the product (hey, good things take time!)

Best Parts of the Convo:
- Jeff got real about marketing struggles (who hasn't been there?)
- Turns out ChatGPT is actually sending them customers now - wild!
- We had a great debate about whether SaaS is still the golden ticket (spoiler: it's way more competitive now)
- Talked about why sometimes it's better to stick with a "pretty good" business than chase the next unicorn

Where They're Headed:
- Aiming for $10M in revenue with a lean team of about 20 people
- Shifting from being super product-focused to really pushing growth
- Geoff's been at it for 8 years and plans to keep going for 7 more

Real talk: This episode is perfect if you're building a SaaS company or thinking about bundling multiple tools together. Geoff drops some serious knowledge about what it's actually like in the trenches.

Check them out at outseta.com if you want to see what they're building!

#SaaS #Startups #Entrepreneurship