Rogue Startups

Craig Hewitt
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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.

  1. hace 1 d

    RS361: Lessons Learned Selling A Business

    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?

  2. 29 jul

    RS360: Kill the Hippo

    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

  3. 21 jul

    Huge Work (and life) Updates

    After 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/ Chapters (00:00:00) - Rogue Startups: A Year in the Life(00:00:45) - Q&A: The Future of Podcasting(00:06:10) - Coaching Isn't Dead(00:10:01) - What Would You Do If You Could Do Whatever You Want To Do

  4. 18 mar

    RS358: Your Design Sucks

    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 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  Chapters (00:00:00) - Francois Brill on Design & UX(00:01:26) - How To Design SaaS Companies' User Experience ((00:04:04) - Light and Dark(00:07:08) - Mixed Bag: Round vs. Square On Mobile(00:09:24) - Kanban 2.8: Color(00:13:19) - Taste Design: The Future of AI(00:16:08) - Onboarding to YouTube(00:20:52) - Ideas in the Pipeline(00:27:25) - Ideation: A Chatbot Interface(00:33:56) - How to Build a Ui with a Human Interface(00:38:48) - Design Systems: The Need for Verification(00:40:45) - How To Build a Design System?(00:49:08) - Top AI Tooling Tips(00:53:08) - A Taste of Hard Work

  5. 11 mar

    RS357: I Got Hacked

    This 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: T... Chapters (00:00:00) - Getting Roasted: AI Security Best Practices(00:01:42) - What I Learned From Working On EMS Soap(00:04:40) - loading pandas in C#(00:05:04) - How to hack a Supabase client with a single code(00:06:51) - How to compromise a C# project with a phishing(00:10:17) - Code Reviewing in the Cloud(00:15:10) - Migration workflow in C#(00:20:45) - Creating a second branch in the Supabase project(00:23:31) - Choosing the right API for your app(00:25:59) - Brandon: How do we structure AI Development?(00:32:35) - Seeking Compound Engineering in the Code(00:33:41) - How to max out Claude Code in 2019(00:38:38) - Building a Software Startup With Claude Code(00:44:04) - Shipkit AI Announcement

  6. 4 mar

    RS356: When to Pivot, When to Push w/ Jesse Hanley

    In 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  Chapters (00:00:00) - Testing New Ideas(00:00:54) - Bento on Testing in AI Software(00:09:18) - How to Start a Startup: Plan Your Startup's Future(00:11:06) - Flows: Things are moving fast(00:16:18) - Reveal: Learning To Optimize Your Website With Nano Banana(00:21:45) - "It'll be hard to get a job in 2021."(00:22:12) - How's your team adapting to the AI revolution?(00:24:16) - Podcaster on the Future of Podcasting(00:27:23) - Shopify's AI Announcement(00:34:43) - Bento CEO on His Strategic Plan(00:38:12) - Gemini 3.8: Using AI to Make Better Design(00:43:08) - Cursor: We're Not Using a CMS(00:48:51) - What is the bottleneck in the WordPress vs. Blog?(00:50:57) - Have You Got Time for Side Projects?(00:54:34) - Custos vs. Riverside: How Big Is the Podcast Market(00:59:38) - How Castos is changing the way we edit videos(01:01:15) - Bob Dylan on His New Direction

  7. 25 feb

    RS355: Code Velocity and the Future of SaaS

    What 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  Chapters (00:00:00) - What Does It Mean to Be a SaaS Founder in 20(00:01:04) - What's the Next 3 or 4 Steps in Your Career?(00:10:01) - Building an AI-ready database in minutes(00:17:18) - Code Review: The Need for Continuous Development(00:21:09) - SaaS vs AI: Buy, Integrate, Arbitrage(00:23:45) - Are We Ready for AI in Medical Applications?(00:25:32) - Bill Gates on AI and Growth(00:30:31) - Marketing: The Challenge of Standing Out(00:34:42) - SaaS as a Service(00:38:52) - Agents and the agentic loop(00:42:00) - Will Agents Be Autonomous in the Future?(00:47:19) - Will Salesforce Give Marketing a Full API Access?(00:48:39) - Agile Coding: How to Keep Up with Everything(00:55:24) - An Optimistic View of the Market

  8. 26/11/2025

    RS354: The State Of Podcasting Heading Into 2026

    Craig 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  Chapters (00:00:00) - Rogue Startups: 100 Days of AI(00:00:48) - How Podcasting Is Affecting AI(00:05:14) - How To Integrate Podcasts into Your Business(00:09:18) - Is Podcasting The Most Popular Media Format?(00:14:18) - Steve Bartlett on Spotify and Video(00:18:11) - Podcaster on Separation of Podcasting and Editing(00:22:19) - Podcasts: How Do They Monetize?(00:23:20) - Has Alitud added advertising to our Episode Builder?(00:25:24) - How to Make a Living on Podcast(00:27:45) - How is AI Affecting Your Company's Business?(00:32:24) - How To Make a Chatbot Like a Human Being(00:34:08) - 100 Days of YouTube(00:37:43) - How to Grow a Podcast on YouTube(00:40:53) - PODCAST: A Chat With Craig

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Información

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.

Ficha técnica

  • Creado por
    Craig Hewitt
  • Años en activo
    2014 - 2026
  • Episodios
    50
  • Clasificación
    Explícito
  • Derechos de autor
    © 2026 RogueStartups
  • Sitio web del podcast
    Rogue Startups
  • Proveedor

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