RS361: Lessons Learned Selling A Business

RS361: Lessons Learned Selling A Business

Author: Craig Hewitt August 4, 2026 Duration: 46:24
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. Highlights from Craig and Colin’s conversation: How to know when it's time to sell your business The stair-step approach to building wealth Founder burnout and losing passion for your company The realities of SaaS valuations today Why building an audience before software matters AI's impact on SaaS and content marketing Why YouTube is still one of the best marketing platforms Life after selling a startup Bootstrapping vs. venture-backed growth Lessons from two experienced SaaS founders Resources and Links from This Episode 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: @TheCraigHewitt  Twitter: @TheCraigHewitt  LinkedIn: Craig Hewitt  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
RS326: 5 Things Most Founders Struggle With [not-audio_url] [/not-audio_url]

Duration: 19:12
Today’s a solo episode with Craig where he’s talking through the 5 common topics and themes that he helps most of his coaching clients through. Whether it’s through his 1:1 coaching with private clients or in serving as…
RS325: Stuck? Ask Yourself These 3 Questions [not-audio_url] [/not-audio_url]

Duration: 10:00
Are you a SaaS founder feeling stuck, unmotivated, or unsure about your next move? In this video, I dive into three powerful questions that can help you break through mental barriers and gain clarity on your business’s d…
RS324: $100 Million Bootstrapped SaaS with Adam Robinson [not-audio_url] [/not-audio_url]

Duration: 41:34
In this episode of the Rogue Startups podcast, Craig sits down with Adam Robinson to explore key topics such as founder psychology, overcoming self-limiting beliefs, and avoiding self-sabotage. They delve into how to ide…
RS323: Breaking Through Plateaus with Josh Ho [not-audio_url] [/not-audio_url]

Duration: 51:33
Today on the Rogue Startups Podcast, Craig chats with Josh Ho from Referral Rock about the peaks and valleys of being a founder. When is the right time to sell? Is there ever a right time? How do you break through a plat…
RS322: Marketing, in 2 hours a week [not-audio_url] [/not-audio_url]

Duration: 16:17
In this episode Craig descirbes his current SaaS marketing approach. Balancing Active and Passive marketing, he’s got his marketing time down to just a few hours a week. Using a video-first, AI-assisted workflow he’s rea…
RS321: B2B Lead Gen on LinkedIn [not-audio_url] [/not-audio_url]

Duration: 47:30
If there’s one thing Craig loves more than podcasting, it’s sales. In this episode, he shares his enthusiasm with tech sales coach Peter Ahn. They discuss everything from bridging the gap between creating content and dri…
RS320: The Psychology of Sales [not-audio_url] [/not-audio_url]

Duration: 43:26
Clearly Design works in every aspect from branding to marketing, from product to promotion. Go to Clearly.Design for a discount on his monthly design subscription service. Tell him that Rogue Startups sent you. What gets…
RS319: Mastering LinkedIn Video Content [not-audio_url] [/not-audio_url]

Duration: 50:21
Clearly Design works in every aspect from branding to marketing, from product to promotion. Go to Clearly.Design for a discount on his monthly design subscription service. Tell him that Rogue Startups sent you. Danny Del…
RS318: LinkedIn Content That Converts [not-audio_url] [/not-audio_url]

Duration: 44:17
Clearly Design works in every aspect from branding to marketing, from product to promotion. Go to Clearly.Design for a discount on his monthly design subscription service. Today Craig is chatting with Nemanja Zivkovic ab…