Rogue Startups

Craig talks with Aaron, who built DocsBot, an AI customer support agent that's almost four years old, about what AI is really doing to SaaS. Aaron shares DocsBot's numbers: slower growth and fewer new customers, but more revenue per customer and lower churn after narrowing in on the right customers. They also get into what it costs to run an AI product, how to choose and switch models, and the AI tools Aaron is excited about next.

Hiten Shah has built Crazy Egg, KISSmetrics, and a long list of products — and right now he’s shipping a new batch of AI tools while stepping back into Crazy Egg after nearly 20 years. In this conversation we get into what’s actually real in AI right now versus what’s hype.

We start with Noats, Hiten’s local-first meeting recorder, and why “the tech wasn’t there” a year ago. That leads into local models: how much hardware you really need, why open-weight models still have a “flavor” from how they’re trained, and why even the frontier labs don’t fully know what a model will be good at until it’s done.

Then we get tactical. Hiten explains how he evaluates new AI tools within minutes of launch, why he treats his work like an “AI factory,” and the big idea of the episode: in the past, go-to-market was a wrapper around the product — today, the product is a wrapper around the go-to-market. He walks through how that plays out across his own products (paid ads, freemium, and a niche community play), and then turns it on my business, Castos, to show what the “obvious future” of a commoditized category looks like.

Chapters
0:00 Noats and local-first meeting notes
4:10 What it really takes to run local models
6:28 Why model training is still a black box
10:22 Where are the US open-weight models?
11:55 Local vs. frontier: how Hiten actually works
13:18 “X is where everything breaks” — evaluating new AI tools fast
15:46 Do you really need to switch tools every week?
18:16 Big-company AI vs. startups for personal productivity
20:39 How to think about growth for an AI product
24:24 The product is now a wrapper around go-to-market
26:30 Does every product need a free tier?
29:19 Coming back to Crazy Egg after 20 years
32:16 What’s exciting — and what keeps Hiten up at night
34:47 Finding the “obvious future” of your business (Castos breakdown)
38:22 Why “grow my podcast” is the new job to be done
40:50 What Hiten’s excited about in AI right now
49:17 Wrap-up: pick who you serve

Links
Noats: https://noats.ai
Hiten on X: https://x.com/hnshah
Hiten’s weekly Friday calls: https://www.hiten.com/
Castos: https://castos.com

What does it take to turn an audience into a business—and how do you do it without losing the enjoyment that got you started? This week on Rogue Startups, Craig and Colin compare notes on building creator businesses. Colin shares what he’s exploring after selling his business, including his golf content, sponsorship opportunities, and fractional roles. Craig talks about growing his YouTube channel toward 25,000 subscribers and building a second revenue stream through ads and brand partnerships.

We dig into the gap between getting views and building a business: growing an email list, creating relevant lead magnets, nurturing subscribers, and developing your own products. We also explore how to find a clear coaching niche by combining your skills and experience—and why honest feedback from your team can help you focus on the work where you add the most value.

Then we get practical about YouTube growth and podcast repurposing. We discuss strong premises, titles, thumbnails, and why the first minute deserves so much attention. We wrap up with how AI tools are changing content production and software businesses, including the opportunities—and uncomfortable questions—that come with automating work you once paid people to do. Fittingly, this episode includes an intro reflecting on using Codex and DaVinci Resolve to edit the conversation itself.

Talking points:

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AI agents are getting a lot more capable, but are they actually making work easier yet? 

Craig and Colin compare their latest experiments with GrokBot, Hermes, OpenClaw, Claude Code, Codex, and other AI tools, including what works, what breaks, and where agents are genuinely reducing cognitive load. 

They dig into open vs. closed systems, shared company agents, local AI, model costs, and the idea of an AI chief of staff that keeps founders focused. 

Plus, Colin shares how he's using AI to overhaul a 15-year-old WordPress site, and they explore what the next generation of AI-powered websites and marketing tools might look like.

Do you need a team to build a successful company these days? On this episode of Rogue Startups, host Craig Hewitt (Castos) and co-host Colin Gray (Alitu and The Podcast Host) tackle one of the biggest questions facing founders today: how do you hire in the age of AI agents? 

Craig and Colin chat about what an "ideal" team looks like, which roles are still worth hiring for, and which ones AI agents can take over (to save more important tasks for humans). They dig into how their own hiring processes have changed and evolved, from async video interviews to paid work samples and screen-recorded tasks. They also explain why a candidate's CV matters far less than watching them think through a problem.

Should you build your next company alone, or find a co-founder?

It's a question that has no easy answer, and AI is making it even more complicated. If one person can now build, market, and operate far more of a business with the help of AI, does having a co-founder still make sense?

Today, Craig and co-host Colin Gray dig into the realities of being a solo founder versus building a company with a partner. They talk about the benefits of having another person to share the load, challenge your thinking, keep you accountable, and be completely honest about the business - along with the risks that come with tying yourself to someone for years.

If you're a solo founder wondering whether you're missing something by going it alone (or maybe you're considering bringing someone into your business), this episode is for you.

What happens to marketing when AI can create almost unlimited content, build software in days, and make it easier than ever for anyone to compete?

In this episode of Rogue Startups, Craig Hewitt and co-host Colin Gray dig into what actually works in marketing today. They explore founder-led marketing, “personal brands” (and why that term makes Craig cringe), content strategy, YouTube, newsletters, podcasts, and the growing importance of creating content that carries a real human voice.

Craig and Colin debate whether blogging still matters, why YouTube may be the strongest starting point for a new brand, and why podcasts are better at building trust than converting cold audiences. They also discuss the marketing FOMO that causes founders to chase every new platform, the value of in-person events, and how to build a content flywheel where one conversation can become videos, newsletters, blog posts, and social content.

The conversation ultimately comes back to a simple question: when AI can produce endless content, what makes yours worth paying attention to? 

AI has made building software dramatically easier. But if everyone can build a product, what happens to SaaS?

In this episode of Rogue Startups, Craig Hewitt is joined by co-host Colin Gray for a wide-ranging conversation about what they're building, how AI is changing their businesses, and why the biggest challenge for SaaS founders may no longer be writing the code. Colin and Craig dig into AI-assisted development, content repurposing, YouTube strategy, AI agents, memory and context, and the increasingly blurry line between building a product and simply building something for yourself.

The conversation gets especially interesting as they compare tools like Cursor, Claude, Codex, Grok, OpenClaw, and Hermes, and discuss the idea of having an AI "boss" that can remember your priorities, surface old ideas, manage your tasks, and push information to you instead of making you constantly hunt for it.

While we weren’t looking, AI has quietly embedded itself into the coaching world. Today Craig sits down with new cohost Colin Gray, founder of Alitu and The Podcast Host, to unpack the current state of the industry.

They dig into why coaching is shifting from information delivery to accountability and thinking-partner work, how Colin built an AI system using Granola transcripts to track patterns across coaching clients and surface his own best ideas for content, and whether "everyone is a media company" still holds up for B2B, legal, and SaaS businesses that swear they're different. 

It's a candid, practical conversation about personal brand versus business brand, one-on-one versus group coaching, and using tools like Claude not to get answers but to get better questions - a must-listen for coaches, consultants, and any solo founder trying to figure out where human expertise still beats a chatbot. 

What happens when AI changes the rules of building a software company? According to Jason Cohen, the answer isn't to predict the future. It's to build around things that remain valuable no matter how technology changes.

In this episode of Rogue Startups, Craig Hewitt talks with Jason Cohen, founder of WP Engine and SmartBear and author of Hidden Multipliers, about growth, strategy, positioning, and building durable businesses in an age of AI. Jason explains why founders should focus on the transformation customers actually want instead of simply adding AI to their products, why repositioning a product can dramatically increase its value, and how to identify the special combination of strengths, customers, and opportunities where your business can win.

Craig and Jason also dig into what kinds of jobs AI is likely to replace, why human creativity and personality remain incredibly valuable, how Jason develops the ideas behind his writing, and why copying someone else's successful framework rarely works without adapting it to your own company culture.

Whether you're building a bootstrapped SaaS company, leading a growing startup, or trying to figure out where your business fits in an AI-driven world, this conversation is full of practical ways to think more clearly about strategy, growth, and competitive advantage.