Rogue Startups

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.

Selling a business isn't just about timing the market. It's about knowing yourself.

In this episode of Rogue Startups, Craig Hewitt sits down with Colin Gray, founder of Alitu and The Podcast Host, to discuss what it's really like to sell a SaaS company after 15 years. Colin shares why he decided to exit, how founders should think about timing a sale, the emotional side of letting go of a business, and why "stair-stepping" through multiple businesses may be a smarter path than chasing a single life-changing exit. They also explore how AI is reshaping SaaS, content marketing, and YouTube, as well as what comes next after selling a company you've spent years building.

Whether you're thinking about selling a business someday or simply trying to build one that lasts, this conversation is packed with honest advice from two experienced bootstrapped founders.

If you're building a SaaS company, one of the hardest questions you'll face isn't how to build a product. It's what to build next.

In this episode of Rogue Startups, Craig Hewitt talks with Steve McLeod, founder of Feature Upvote and author of Kill the Hippo, about product strategy, customer research, and why the loudest customer isn't always the one you should listen to. Steve shares lessons from interviewing successful bootstrapped SaaS founders, explains why talking directly with customers beats relying on surveys and feature voting alone, and discusses how companies can avoid building the wrong features.

Craig and Steve also explore Steve's journey writing Kill the Hippo, Feature Upvote's successful pivot into the gaming industry, the realities of running a mature SaaS business, and how AI is changing product development and customer acquisition. They close with an honest conversation about the future of bootstrapped SaaS and why today's founders face a very different landscape than they did just a decade ago.

Whether you're launching your first startup or leading an established software company, this episode is full of practical advice on product management, customer feedback, ideal customer profiles (ICP), founder decision-making, and sustainable SaaS growth.

00:00 Why Building the Right Product Matters

01:43 Why Steve Wrote Kill the Hippo

03:09 The Pivot That Changed Feature Upvote

04:36 Why the Most Popular Feature Is Usually Wrong

06:26 Talk to Customers, Not Just Surveys

08:19 Finding Your Real Ideal Customer

13:05 How Kill the Hippo Came Together

16:59 Why Steve Wanted to Write a Book

19:04 The Reality of Being a Solo Founder

21:06 Are Product Prioritization Frameworks Worth It?

23:54 Hiring People Who Think Like Your Customers

27:45 Building for Future Customers Without Losing Today's

29:24 Product Strategy for Mature SaaS Companies

31:26 Avoiding the "Abandoned Product" Trap

34:00 How Mature SaaS Teams Ship New Features

36:19 Build Features That Make Customers Say "Wow"

38:20 Is SaaS Really Dead?

42:35 The Golden Age of Bootstrapped SaaS

- Feature Upvote: https://featureupvote.com/  

- Steve on LinkedIn: https://www.linkedin.com/in/steve-mcleod-fuv/ 

- Castos Free Tools: castos.com/tools

- Email me: [email protected] 

- Find me on Twitter: @TheCraigHewitt

- Craig on LinkedIn: http://linkedin.com/in/craig-hewitt-78386a66  

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