Rogue Startups

On Rogue Startups we share the journey of startup founders as they're growing their businesses. We feature experts in the fields of sales, marketing, and product development to hear how they're growth hacking their productized services and SaaS products. If you're on the journey of an entrepreneur then tune and hear how we're tackling some of the same obstacles you may be facing, and how we're winning in the game of business. Listeners of Startups for the Rest of Us, My First Million, Mixergy, and Bootstrapped Web will love checking out our show.

Rogue Startups is a business podcast hosted by Craig Hewitt, with 50 episodes on record and a Required Pod Score of 81. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Craig Hewitt hosts Rogue Startups, a business show with 50 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Rogue Startups

  RS363: Why Talking to AI About Your Business Is Dangerous

  Aug 18, 202633 min

  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: podcast@roguestartups.com Find me on Twitter: https://twitter.com/TheCraigHewitt LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/ Email: podcast@roguestartups.com 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

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  Rogue Startups

  RS362: Hidden Multipliers with Jason Cohen

  Aug 11, 202651 min

  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. Highlights from Craig and Jason’s conversation: How to make strategic decisions in an uncertain market What customers will still value in the age of AI Why AI should solve customer problems rather than simply be added to products How positioning can dramatically increase a product's value Why senior developers benefit more from AI than junior developers What chess teaches us about AI and human creativity Why human personalities still matter in content and marketing How Jason Cohen developed the ideas behind Hidden Multipliers Why copying successful business frameworks often fails How founders can find their own strategic advantage The right and wrong ways to use metrics What AI means for the future of SaaS Resources and Links from This Episode: AI Skills which facilitate ideas from the book and Jason’s articles https://longform.asmartbear.com/ Jason on X: https://x.com/asmartbear hiddenmultipliers.com Castos Free Tools : castos.com/tools Email me: podcast@roguestartups.com Find me on X: https://twitter.com/TheCraigHewitt Craig on LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66 / Chapters (00:00:00) - Will Jobs Get Automated? (00:00:37) - Interviewing Jason Cohen on Growth (00:01:41) - The Making of the Smart Beer Live Podcast (00:06:48) - How to Figure Out the Most Important Things in the Business (00:10:15) - Re-positioning Your Business Software (00:11:45) - Costs of AdWords and AI (00:17:23) - "I Never Want to Watch a Computer" (00:20:16) - Behind the Hidden multipliers: How to Grow a Business (00:24:00) - Your Thoughts on Writing (00:29:51) - Reasons for a Startup Framework Fit (00:34:09) - The Common Truth of Metrics (00:37:18) - Do You Need Metrics in Your Company? (00:40:35) - Top 5 Things AI Will Affect in 2030 (00:45:22) - Do Jobs Get Replaced by AI? (00:47:25) - No Unique Advantage? (00:49:51) - Book Review

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  Rogue Startups

  RS361: Lessons Learned Selling A Business

  Aug 4, 202646 min

  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 Chapters (00:00:00) - How to Get Out of Debt in Retirement (00:01:33) - A Chat With Colin on Rogue Startups (00:02:54) - When Should You Sell Your Business? (00:09:18) - Ideas for Buying or Selling Our Company (00:14:57) - Allevi On Falling Out Of Love With the Business (00:16:56) - How to Balance Working and Living (00:21:12) - Getting a Job in the Age of AI (00:23:01) - Ex-CEO on His Exit (00:27:08) - Podcasting: The SaaS Jobs Apocalypse (00:29:23) - SaaS and Content: The Future of Both (00:36:43) - How to Keep Your YouTube Channel Updated (00:39:47) - Under Threat: Podcasts and Video (00:41:21) - Alitu Expands Into Paid Acquisitions (00:43:26) - Exclusives: Colin's Exit (00:44:29) - Co-Hosting: Solo or Team?

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  Episode #360

  RS360: Kill the Hippo

  Jul 29, 202644 min

  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. In this episode: 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 Resources and Links: - Feature Upvote: https://featureupvote.com/ - Steve on LinkedIn: https://www.linkedin.com/in/steve-mcleod-fuv/ - Castos Free Tools: castos.com/tools - Email me: podcast@roguestartups.com - Find me on Twitter: @TheCraigHewitt - Craig on LinkedIn: http://linkedin.com/in/craig-hewitt-78386a66 If you feel Rogue Startups has benefited you and might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. Chapters (00:00:00) - Knowing What Product to Build in the SaaS Age (00:01:45) - Writing a Book About Pivoting (00:04:14) - How to Decide What to Build Next (00:10:27) - Have You Changed Your ICP? (00:12:37) - Writing The Bootstrap Book (00:16:26) - What are you hoping the book does for you? (00:18:08) - In the Elevator With a Co-founder (00:23:10) - The Importance of Talking to Customers (00:27:54) - How Do You Keep Your Product From Getting Stuck? (00:30:04) - A Design for Less Annoying CRM (00:32:24) - How To Evolve a Matured Product (00:34:47) - The Need for a 'Wow' (00:36:25) - SaaS and the future of podcast (00:40:56) - Bootstrapped SaaS: The Golden Age is Over (00:42:40) - Kill the Hippo

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  Rogue Startups

  RS358: Your Design Sucks

  Mar 18, 202654 minS0

  <p>In this episode, Craig sits down with Francois Brill, Head of Product at Castos and longtime design collaborator, for an honest and entertaining conversation about what it really takes to build great-looking products in the age of AI. Using Outlier as a live case study, Francois walks through the marketing site and product UX in real time, calling out the small but costly design mistakes that make AI-built tools look generic. From embarrassing mismatched button styles to cognitive overload on ideation pages, this episode is a must-listen for anyone vibe-coding their next SaaS app and wondering why it just...

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