Rogue Startups

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

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. Highlights from Craig and Colin’s conversation: How AI is making software dramatically easier to build - and why that creates a new challenge for SaaS founders Why AI tools become much more powerful when they're customized to your specific workflows Is "anyone can build this" becoming a real problem for SaaS companies? Why the hardest part of building software may no longer be writing the code The biggest risk of AI-built software: building something nobody actually wants How Craig and Colin are using AI agents to reduce cognitive load and manage their work Why your AI assistant may need access to your entire digital life to be genuinely useful Turning conversations and existing content into a repeatable publishing workflow Why sometimes a solo founder just needs an AI boss Why more features aren't always the answer for a growing SaaS business What should an AI assistant actually remember about you? How AI agents could change the way founders work, prioritize, and make decisions 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) - What's the Risk of Building a SaaS in Claude Code(00:00:28) - Rogue Startups: Updates on AI(00:05:07) - How to Build a Podcast on YouTube(00:10:12) - How to hire a non-technical developer(00:15:19) - Cursor Cloud vs. Grokbot: What's The Difference(00:19:46) - Grokbot and OpenCluster: The One Place for Everything(00:25:00) - How Do You Keep Yourself Organized?(00:30:50) - Working on a 6 week plan(00:34:27) - Pushing the pace of product development(00:36:58) - Ideas on Grokbot: The Knowledge Librarian(00:42:47) - Your Bots: Do Your Job(00:43:29) - How to Organize Your Brain in 2019(00:45:11) - OpenClaw vs. Codex: Which is better?(00:47:34) - Colin Gray on Social Media

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.  Highlights from Craig and Colin’s conversation: AI can't coach you. It can only answer you. The "how-to" business is dying, and courses are the first casualty. Why one podcaster treats Claude like a co-founder (and where that backfires). Coach or mentor? The real spectrum nobody talks about. Selling a podcast editing app for millions, then figuring out what's next. "Personal brand" is a dirty word. Here's the better way to think about it. The one B2B industry everyone assumes content can't touch (it can). Coaching's new job: not answers, accountability. One-on-one vs. group coaching: which one actually makes people feel heard. Turning client call transcripts into an AI memory system that spots patterns humans miss. Mining your own coaching sessions to find your most original ideas. Resources and Links from This Episode: Produced by Castos 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) - A Coach's Role in Your Business(00:00:32) - Colin Gray Training for His First Half Marathon(00:02:35) - Meet Alitu(00:04:55) - Craig on His Exit(00:05:28) - Interviewing Silicon Valley's Rich People(00:05:57) - AI for Coaching and Business(00:09:38) - What Kind of Coaches Should You Work With?(00:11:35) - How to grow a creator business in 2019(00:13:31) - Are Businesses Ready to Be a Media Company?(00:16:01) - Podcasting: The Best Use Case for Content(00:16:40) - Colin Gray on His Personal Brand(00:19:29) - Group Coaching vs One-on-One(00:23:30) - How AI is helping me with my coaching(00:28:07) - The AI Product Hype Cycle