Podcast
Rogue Startups
Hosted by Craig Hewitt · EN
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.
24episodes
Episodes
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RS361: Lessons Learned Selling A Business
1w ago00:46:24Tap to summarizeSelling 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
Transcribe →RS360: Kill the Hippo
2w ago00:43:39Tap to summarizeIf 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.
Transcribe →Huge Work (and life) Updates
3w ago00:14:53Tap to summarizeAfter an almost 5 month break from the podcast, I'm Back! In this episode I talk through updates with me, Castos, my coaching business, and where the podcast is headed into the future. Spoiler alert...i'm getting a new cohost. Connect on the socials: x.com/thecraighewitt instagram.com/thecraighewitt https://www.linkedin.com/in/craig-hewitt-78386a66/
Transcribe →RS358: Your Design Sucks
Mar 1800:54:07Tap to summarizeIn 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 does not feel polished. Highlights from Craig and Francois’ conversation: AI-generated design is the new "tell" that your product was built without a designer Picking one mode, light or dark, is almost always better than trying to do both Rounded inputs paired with square buttons is one of the most common and fixable design mistakes Color should guide user action, not decorate the interface UX is how something works; UI is what it looks like, and they require different thinking Cognitive overload kills conversion, especially on feature-rich pages like ideation tools A Design MD file can teach AI your brand system so every output stays consistent Code is cheap now, so the value has shifted to vision, taste, and design thinking Building fast and iterating beats trying to get it perfect the first time If everyone can prompt the same thing, standing out requires taste and a real system Resources and Links from This Episode: Clearly Design: https://www.clearly.design/ Francois on LinkedIn: https://www.linkedin.com/in/fbrill/ Outlier: https://outlier.so/ Castos Free Tools: castos.com/tools Email me: podcast@roguestartups.com Find me on Twitter: @TheCraigHewitt If you feel like Rogue Startups has benefited you, and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com
Transcribe →RS357: I Got Hacked
Mar 1100:44:26Tap to summarizeThis week on the Rogue Startups, Craig gets roasted. He brought in experienced software engineer Brandon Hancock after building the AI-powered SaaS app Outlier largely through “vibe coding,” so Brandon could audit the entire codebase live during the episode. The result? An honest but useful breakdown of what happens when non-technical founders ship fast with AI tools. Brandon digs into real security risks, common architecture mistakes, and the best practices every founder should follow when building AI-driven products. If you’re launching SaaS with tools like Next.js, Supabase, and Claude, or simply adding AI features to your existing product, this episode offers practical lessons on building faster without accidentally breaking everything. Check the episode out on YouTube to see Brandon dig through Craig’s code onscreen. Highlights from Craig and Brandon’s conversation: What “vibe coding” looks like when building a real production startup How a single exposed Supabase key can create major security risks Why row-level security is critical for protecting user data Using AI to audit code and uncover vulnerabilities in minutes Simple fixes that dramatically improve SaaS security Why many AI code review tools miss critical issues The danger of exposing backend clients in frontend code How server actions can replace many API endpoints Best practices for managing database migrations with Drizzle ORM Why staging environments save founders from catastrophic production mistakes The difference between moving fast and building responsibly How to structure AI documentation for better development workflows Using task templates to teach AI your coding standards Practical lessons for founders building SaaS products with AI tools Resources and Links from This Episode Shipkit.ai: https://www.shipkit.ai/ Brandon on LinkedIn: https://www.linkedin.com/in/brandon-hancock-ai Brandon’s website: https://brandonhancock.io/ Brandon on YouTube: https://www.youtube.com/@aiwithbrandon Rogue Startups on YouTube: https://www.youtube.com/@roguestartups Castos Free Tools: castos.com/tools Email me: podcast@roguestartups.com Find me on Twitter: @TheCraigHewitt If you feel like Rogue Startups has benefited you, and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com
Transcribe →RS356: When to Pivot, When to Push w/ Jesse Hanley
Mar 401:02:06Tap to summarizeIn this episode of Rogue Startups, Craig sits down with Jesse Hanley, founder of Bento, for a wide-ranging conversation about building and growing SaaS businesses in the age of AI. From vibe coding and AI-assisted development workflows to product strategy, business ceilings, and the existential shifts happening across the tech landscape, Jesse and Sandy share candid insights from their own experiences as founders navigating a rapidly changing environment. If you're a bootstrapped founder, indie hacker, or SaaS entrepreneur trying to figure out how to stay relevant and move fast, this one's for you. Highlights from Craig and Jesse’s conversation: Testing and QA are still the unglamorous bottleneck nobody talks about enough The founders who stay close to the code sleep better at night Opus 4.5 in Cursor is the closest thing to having a full dev team on speed dial Build your foundation like a brick house, and everything else can be Play-Doh™ AI is making founders fall back in love with parts of their business they used to dread Shopify can now build custom apps on demand, and that should make plugin developers nervous If your whole product is basically one feature, it might be time to rethink things Sometimes the ceiling you're hitting is the category, not your effort The best side projects either pay for themselves immediately or swing for the fences Building through AI disruption takes the same stubborn optimism it took to survive COVID Resources and Links from This Episode Jesse Hanley: https://jessehanley.com/ Connect with Jesse on LinkedIn: https://www.linkedin.com/in/jessehanley/ Bento: https://bentonow.com/ Castos Free Tools: castos.com/tools Email me: podcast@roguestartups.com Find me on Twitter: @TheCraigHewitt If you feel like Rogue Startups has benefited you, and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com
Transcribe →RS355: Code Velocity and the Future of SaaS
Feb 2500:58:05Tap to summarizeWhat does it mean to be a SaaS founder in a world where AI can build features faster than we ever could? In this conversation, Craig sits down with Arvid Kahl to unpack the shifting reality of software, competition, and the craft of SaaS in 2026. They talk about code velocity, discernment, marketing in an AI-saturated world, and why SaaS is not dead, even as the software part becomes commoditized. Listen in to find out what actually matters these days, if you want to build something that lasts. Highlights from Craig and Arvid’s conversation: AI is shifting the founder’s role from building to judging quality and making decisions Code velocity now matters more than perfect architecture for most SaaS products Replacing junior developers entirely with AI risks creating a future talent gap Your real competition increasingly includes general AI tools, not just other SaaS companies AI has leveled the marketing baseline, making differentiation and brand more important than ever Standing out requires taste, point of view, and clear positioning, not just tactics Acquiring legacy SaaS and refactoring with AI could be a major opportunity The service part of SaaS still matters most, because AI generates products but not businesses Resources and Links from This Episode Podscan: https://podscan.fm/ Castos Free Tools: castos.com/tools Email me: podcast@roguestartups.com Find me on Twitter: @TheCraigHewitt If you feel like Rogue Startups has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com
Transcribe →RS354: The State Of Podcasting Heading Into 2026
Nov 2600:41:22Tap to summarizeCraig is back! Today, he welcomes fellow podcaster Colin Gray back to the podcast. They dive into the ever-evolving world of podcasting, reflecting on how much the landscape has shifted over the last decade and what people are craving now more than ever: genuine human connection. From the tug-of-war between YouTube and podcast growth, to what it really means to build an AI-first product, they explore the trends shaping creators, customers, and the platforms that connect them. Highlights from Craig and Colin’s conversation: How podcasting has changed over the last 10 years The more we’re pulled toward AI, the more we crave genuine connection Is it easier to grow a YouTube channel or a podcast? Content integration and becoming a centralized hub Spotify’s role in the evolution of podcasting Monetization: ads, donations, subscriptions, and more Balancing and prioritizing feature requests How AI is shaping customer expectations How to make your product AI-first Resources and Links from This Episode: The Podcast Host: https://www.thepodcasthost.com/ Colin on LinkedIn: linkedin.com/in/colinmcgray?originalSubdomain=uk beehiiv: https://www.beehiiv.com/ Kit: https://kit.com/ Creator Hooks: https://creatorhooks.com/ Castos Free Tools: castos.com/tools Email me: podcast@roguestartups.com Find me on Twitter: @TheCraigHewitt If you feel like Rogue Startups has benefited you, and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com
Transcribe →RS353: Is This the Last Organic Marketing Channel
Oct 100:50:57Tap to summarizeIn today’s episode, Craig sits down with SaaS founder and entrepreneur Brian Casel to talk about the future of software and AI. With years of experience building and growing SaaS companies, Brian shares his perspective on how artificial intelligence is reshaping the industry, from launching in niche markets and creating content that resonates to the challenges SaaS businesses will face in the next few years. They also dive into YouTube growth strategies, monetizing AI tools, and whether today’s AI boom is a lasting shift or just another bubble. Highlights from Craig and Brian’s conversation: Craig’s 100 Days of AI Challenge Growing with content: from weekly AI newsletters to scaling YouTube channels Brian’s current projects – Agent OS, Builder Methods, and the difference between live workshops and online courses How to monetize AI tools and content in today’s market The power of the B2B super niche and what it takes to launch a new SaaS business in 2025 AI challenges for SaaS companies over the next few years Behind the scenes of Craig and Brian’s YouTube workflows How to choose the right content for your audience (and avoid wasting time creating the wrong stuff) Where is AI headed? Is this just a bubble, or real long-term change? Will artificial intelligence replace artists, musicians, painters, and writers? Resources and Links from This Episode: Brian Casel: https://briancasel.com/ Builder Methods: https://buildermethods.com/ Brian on YouTube: https://www.youtube.com/@briancasel Find me on Twitter: @TheCraigHewitt If you feel like Rogue Startups has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com
Transcribe →RS352: AI Killed Traditional Marketing – Here's What's Next
Sep 2400:49:33Tap to summarizeRoss Simmonds, founder of Foundation Marketing, has built a reputation for helping ambitious SaaS and B2B brands stand out online with data-driven growth strategies. In this episode, Craig sits down with Ross to dive into the future of marketing, SaaS growth, and social media in the age of AI. Marketing has transformed dramatically over the past decade, and with the rise of AI-powered marketing methods, it feels like the Wild Wild West. But within all that chaos are opportunities that we shouldn’t miss out on.. Ross and Craig explore how founders and marketers can leverage AI to create content, reach the right audience, and scale profitably in today’s fast-changing landscape. Highlights from Craig and Ross’s conversation: Why traditional B2B marketing tactics are failing and what actually drives SaaS growth in 2025 Create exclusive, high-value content that your target market can't find anywhere else AI marketing parallels the mobile revolution We're only at the beginning of the AI marketing cycle, and why the long game matters Which social media platforms actually work for B2B in today's landscape Every platform has your audience, but no one's cracked the code Monetize your existing high-performing pages and don't abandon what's already working Search behavior has evolved beyond Google Stop ignoring Reddit for B2B marketing Elevenlabs and Manus case studies. Plus, why Google will dominate long-term AI marketing Resources and Links from This Episode: Ross Simmonds on X (Twitter): https://x.com/TheCoolestCool Ross Simmonds on LinkedIn: https://www.linkedin.com/in/rosssimmonds/ Foundation Marketing: https://foundationinc.co/ Ross Simmonds online: https://rosssimmonds.com/ Email me: podcast@roguestartups.com Find me on Twitter: @TheCraigHewitt If you feel like Rogue Startups has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com
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