RS366: When (and how) To Pick a Co-Founder

RS366: When (and how) To Pick a Co-Founder

Author: Craig Hewitt September 8, 2026 Duration: 41:23
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: podcast@roguestartups.com  Find me on Twitter: https://twitter.com/TheCraigHewitt LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/  Email: podcast@roguestartups.com

Behind every new company is a story, and Rogue Startups digs into the real ones-the messy, uncertain, and exhilarating paths founders actually walk. This isn't about polished success tales; it's a candid look at the day-to-day grind of building a business from the ground up. You'll hear directly from entrepreneurs in the thick of it, along with seasoned experts who specialize in the crucial engines of growth: sales, marketing, and product development. Conversations focus on practical tactics, particularly around scaling productized services and SaaS offerings, exploring the real "how" behind their growth hacking strategies. The value of this podcast lies in that shared experience-hearing how others navigate the very obstacles you might be staring down, and learning what moves actually led to a win. It’s for anyone who prefers the unvarnished truth of entrepreneurship over theory, offering a sense of camaraderie and a toolbox of ideas drawn from the front lines. Tune in for authentic dialogue that skips the fluff and gets straight to the challenges and victories of building something new.
Author: Language: en-us Episodes: 50

Rogue Startups
Podcast Episodes
RS346: What 11 Years in SaaS Really Looks Like [not-audio_url] [/not-audio_url]

Duration: 48:49
In this episode of the podcast, Craig sits down with longtime entrepreneur Colin Bartlett, cofounder of StatusGator, to explore what it really takes to build, and sustain, a SaaS business over the long haul. With more th…
RS345: The State Of Search 2025 [not-audio_url] [/not-audio_url]

Duration: 18:27
- LLMs.txt article: https://www.quoleady.com/llm-txt-files/ - Craig's YouTube channel: https://youtube.com/@thecraighewitt
RS344: 12 Years to Overnight Success with Amar Ghose [not-audio_url] [/not-audio_url]

Duration: 47:27
What does it really take to lead a company for over a decade—and still be growing? In this episode, Craig chats with Amar Ghose, founder and longtime CEO of ZenMaid, about the challenges, lessons, and evolution that come…
A Caffeine Infused Diatribe [not-audio_url] [/not-audio_url]

Duration: 46:59
Hello, remember me? Sorry that it's been 6 weeks, but I'm back. In this episode I talk through what I've been up to recently, what's going on with Castos, with myself personally, and things I'm learning growing the busin…
RS342: SaaS Survival Mode - AI, Niches & Navigating Chaos [not-audio_url] [/not-audio_url]

Duration: 45:12
In this episode of Rogue Startups, Craig chats with Jesse Hanley, marketer, self-taught developer, and founder of Bento, a powerful email marketing platform for modern teams. With today’s economy in flux and global event…
RS341: Microconf 2025 Recap [not-audio_url] [/not-audio_url]

Duration: 17:48
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…
RS340: Is AI Killing SaaS w/ Tim Schumacher [not-audio_url] [/not-audio_url]

Duration: 43:00
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, th…
RS339: AI Skeptic, or Believer [not-audio_url] [/not-audio_url]

Duration: 47:49
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, wha…
RS338:  Balancing Your Use of AI with Aaron Francis [not-audio_url] [/not-audio_url]

Duration: 52:12
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 yo…
RS337: Building AI Native SaaS w/ Jordan Gal [not-audio_url] [/not-audio_url]

Duration: 48:06
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…