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: Building a creator business without turning a hobby into a chore. Monetizing through sponsorships, brand deals, and fractional roles. Why smaller audiences can still be valuable to sponsors. Turning podcast and YouTube audiences into newsletter subscribers. Using lead magnets, segmentation, and your own products to build more predictable revenue. Finding a coaching niche through a distinctive combination of skills. Asking your team where you can contribute most effectively. Giving each piece of content a clear job: views, subscribers, or revenue. Creating stronger YouTube hooks, titles, thumbnails, and opening minutes. Repurposing podcast conversations into standalone videos with custom intros. Using AI to streamline editing, copywriting, and publishing. How changing customer needs could reshape SaaS and service businesses. Subscribe to Rogue Startups wherever you listen, and subscribe on YouTube for future episodes. Follow Craig @thecraighewitt and Colin @colinmcgray on social media. Let us know what you thought of the AI-edited episode—and which practical AI workflows you’d like us to explore next. Get goodies via email: https://craighewitt.kit.com/a7a6c4b5ef

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. Highlights from Craig and Colin’s conversation: Open vs. closed AI agents for running a business Why Craig chose Hermes as Castos' shared company agent The security challenge of giving AI agents real power Why AI should reduce cognitive load, not create more work How Colin uses AI for CRM, task management, and daily planning Claude Code vs. Codex, Cursor, and other AI development tools Why expensive AI models aren't always the best choice The case for running AI locally or privately How cheap AI access encourages founders to experiment Can an AI chief of staff actually keep you focused? Using AI to overhaul a 15-year-old content site How tiny AI-built tools could replace traditional lead magnets Resources and Links from This Episode: Produced by Castos Productions: https://castos.com/productions/  The Podcast Host: https://www.thepodcasthost.com/  Colin on LinkedIn: linkedin.com/in/colinmcgray?originalSubdomain=uk  Castos Free Tools: castos.com/tools Email me: [email protected]  Find me on Twitter: https://twitter.com/TheCraigHewitt  LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/  Email: [email protected] Chapters (00:00:00) - Intro and topic setup: bots and agents(00:01:23) - Open vs closed agent platforms(00:03:35) - Why choosing Hermes for a shared team agent(00:07:07) - Permissioning and security challenges with Hermes(00:09:08) - Vision for AI teammates across a company(00:10:44) - Personal use: Grokbot vs Claude code workflows(00:12:53) - CRM, task management, and cognitive load reduction(00:16:09) - Mobile workflows, Notion, and GitHub syncing(00:19:06) - App preferences: Claude vs Codex vs Cursor vs Antigravity(00:22:00) - Right-sizing models and cost discipline(00:22:19) - Golf video workflow and downgrading models to save cost(00:25:33) - Local and private AI compute considerations(00:29:35) - Enterprise API costs, subsidies, and sovereignty concerns(00:32:35) - Value of experimentation under usage limits(00:33:56) - Chief of staff model and multi-agent orchestration(00:37:59) - Chief of staff for managing priorities and stale projects(00:41:25) - Old-school business plans teaser(00:42:01) - Renovating lawns4u.com with AI agents(00:45:00) - WordPress vs modern stacks (Astro, Next.js) discussion(00:47:33) - Building tools and lead magnets beyond WordPress(00:50:15) - Wrap up and future topics

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. Highlights from Craig and Colin’s conversation: Why you might still want a team, even if you don't need one What a minimal modern software team looks like What founders should never fully hand off How AI agents are changing customer research The best first hires for growth and partnerships Why every hire should be an AI power user How to spot great candidates beyond the CV Using paid work samples and screen recordings in hiring The hidden costs and risks of hiring overseas Why EORs and Merchant of Record services can simplify global hiring and sales When to hire a human vs. build an AI agent The trade-offs of staying solo with AI vs. building a team Resources and Links from This Episode: Produced by Castos Productions: https://castos.com/productions/  The Podcast Host: https://www.thepodcasthost.com/  Colin on LinkedIn: linkedin.com/in/colinmcgray?originalSubdomain=uk  Castos Free Tools: castos.com/tools Email me: [email protected]  Find me on Twitter: https://twitter.com/TheCraigHewitt  LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/   Email: [email protected]

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. Highlights from Craig and Colin’s conversation: Why having a co-founder can make the entrepreneurial journey dramatically less lonely How AI is changing the traditional argument for having a co-founder Why another brain in the business may be more valuable than another specific skill set The role of accountability, honest feedback, and staying focused What to consider before choosing a business partner Why personality, communication style, and problem-solving approach matter so much The importance of agreeing on what you actually want from the business How equity splits can create problems when partners join at different stages Options vs. profit sharing as ways to reward employees How to build a leadership team that can eventually operate without the founder The advantages of speed, flexibility, and control as a solo founder Why AI may be making solo-founded companies more viable than ever Resources and Links from This Episode: Produced by Castos Productions: https://castos.com/productions/  Sam Paar blog post: https://joinhampton.com/blog/the-template-that-made-sure-my-co-founder-and-i-were-perfect-partners  The Podcast Host: https://www.thepodcasthost.com/  Colin on LinkedIn: linkedin.com/in/colinmcgray?originalSubdomain=uk  Castos Free Tools: castos.com/tools Email me: [email protected]  Find me on Twitter: https://twitter.com/TheCraigHewitt LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/  Email: [email protected] Chapters (00:00:00) - Rogue Startups: The Search for a Co-Founder(00:00:50) - Getting back in the groove of running(00:03:04) - Talking Business With My Partners(00:04:35) - Does a Co-Founder Need a Partnership in AI?(00:09:00) - Craig Menear: Coaching With Single Founders(00:11:49) - What is a Co-Founder's Decision on Partnering?(00:13:15) - What kind of areas of consideration did I miss besides equity pay,(00:17:46) - Ideas for a Good Co-Founder Relationship(00:19:43) - Have You Ever Shared Options With Your Team?(00:21:44) - How was the, I don't know, the vibe with the(00:23:00) - Is Having a Co-Founder Better Than Being a Solo Founder(00:27:00) - What's The Big Benefit of Starting a Company Solo?(00:30:01) - Does the Company Have a Co-founder Type Role?(00:34:21) - Good Hires vs. Bad Hires(00:36:02) - I love working with a team

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?  Highlights from Craig and Colin’s conversation: Why the best marketing ultimately has to create a return for the customer How founders can avoid getting trapped by marketing FOMO Why founder-led marketing may matter more as AI creates more faceless businesses How to figure out what makes you genuinely different Why YouTube may be the best starting point for building a modern personal brand Whether blogging and SEO still have a place in an AI-generated content world Why real stories, experiences, and opinions can make content stand out from AI-generated material How to turn one podcast conversation into a complete content ecosystem Why podcasts are better at building trust than converting cold audiences The underrated marketing power of in-person events and relationships How to build a YouTube and newsletter flywheel Why paid advertising could become more accessible through AI-powered tools Resources and Links from This Episode: Produced by Castos Productions: https://castos.com/productions/  The Podcast Host: https://www.thepodcasthost.com/  Colin on LinkedIn: linkedin.com/in/colinmcgray?originalSubdomain=uk  Castos Free Tools: castos.com/tools Email me: [email protected]  Find me on Twitter: https://twitter.com/TheCraigHewitt  LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/  Email: [email protected] Chapters (00:00:00) - The Podcast Is Dead(00:00:42) - Rogue Startups: More Money, Stupid(00:02:31) - Podcast Marketing: The Business of Podcasting(00:07:12) - Likely More Personal Brand than Social Marketing(00:09:46) - Developing a Personal Brand(00:13:52) - How to build a personal brand on a platform(00:17:22) - How to Build a Modern Business on the Web(00:23:34) - How Long Form Writing Is Made(00:24:25) - How to Promote Your Podcast and YouTube Videos(00:30:32) - milo on 'Physics'(00:30:50) - How to Promote your YouTube Videos on a Podcast?(00:37:08) - In the World of In-Person Events(00:38:35) - How to Market Your Podcast at Events(00:41:24) - Golf Star on His Next Thing(00:41:41) - How to Build a YouTube Channel and a Podcast(00:45:28) - What's Your First Channel for AI?(00:47:16) - Paid Advertising: The Future of AI(00:48:40) - Episode 1