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In this episode Craig talks with Aaron, who built DocsBot, an AI customer support agent that's almost four years old, about what AI is really doing to SaaS. Aaron shares DocsBot's numbers: slower growth and fewer new customers, but more revenue per customer and lower churn after narrowing in on the right customers. They also get into what it costs to run an AI product, how to choose and switch models, and the AI tools Aaron is excited about next. Topics discussed Growth in the AI era: new customer acquisition is down year over year, but revenue per customer is up 20% from last year Finding the ideal customer: talking to customers, cancellation surveys, and pointing AI agents at all of the product and Stripe data, after reading Jason Cohen's book Hidden Multipliers Signal density: why founders with only a handful of customers struggle to draw conclusions Where customers come from now: organic search, AI search, referrals, conferences like WordCamp, and an agency partner program Why big companies move slowly: and why that makes larger customers stickier Churn to DIY: churned customers citing AI or their own custom solution went from 1.6% to 13%, and most weren't a good fit anyway Pricing around token costs: from bring-your-own-key to included usage to AI credits Evaluating new models: why letting customers edit their system prompt makes evals hard, and a classifier that behaved differently on GPT-5.4 Choosing models: balancing cost, speed and quality instead of reaching for the newest model Local and specialised models: embedding models, Cohere for other languages, and Mistral for PDF extraction Privacy: a tiny model in the chat widget that redacts personal information before it leaves the user's browser What's next: using a new model to re-rank search results at a fraction of the cost Key takeaways The biggest cheat code for finding your ideal customer, in Aaron's words, is to "talk to your customers". Don't pick your ideal customer by revenue alone: DocsBot's biggest enterprise customer uses the product completely differently from almost everyone else. Customers who leave to build their own alternative are often not best-fit customers: too price sensitive, a tiny team, or not enough support tickets. Bring-your-own-key let a fully bootstrapped company launch an AI product without paying for inference for about the first two years. For an AI support agent, speed matters, so the newest model on its highest reasoning setting isn't always the right choice. Model upgrades can cause regressions that evals don't necessarily show. Chapters (00:00:00) - Intro: Is the SaaS apocalypse here?(00:00:59) - Growth metrics and MRR trends over 12 months(00:02:08) - Focusing on ICP to boost revenue per customer(00:03:11) - Churn rates and pricing restructuring(00:04:49) - Talking to customers to define the ideal customer profile(00:07:32) - Signal density and sample size in customer data(00:09:13) - Customer acquisition channels and what's working now(00:10:47) - Events, conferences, and agency partnerships(00:13:05) - Enterprise inertia vs. consumer switching risk(00:15:19) - Enterprise adoption pace and pilot deployment friction(00:17:03) - How AI changes customer support buying behavior(00:19:07) - DIY/AI churn: are customers building their own solutions?(00:20:45) - Price increases and churn reasons breakdown(00:21:55) - Token costs, pricing strategy, and bring-your-own-key history(00:26:06) - Evaluating and switching AI models internally(00:29:24) - Personal model stack and balancing cost, speed, quality(00:34:00) - Local models, embeddings, and specialized extraction tools(00:36:25) - Small/local models and future of specialized AI(00:38:56) - PII redaction with tiny on-device models(00:40:16) - What's exciting next: re-ranking, Gemini, and new paradigms(00:43:19) - Wrap-up and where to find DocSpot

Hiten Shah has built Crazy Egg, KISSmetrics, and a long list of products — and right now he’s shipping a new batch of AI tools while stepping back into Crazy Egg after nearly 20 years. In this conversation we get into what’s actually real in AI right now versus what’s hype. We start with Noats, Hiten’s local-first meeting recorder, and why “the tech wasn’t there” a year ago. That leads into local models: how much hardware you really need, why open-weight models still have a “flavor” from how they’re trained, and why even the frontier labs don’t fully know what a model will be good at until it’s done. Then we get tactical. Hiten explains how he evaluates new AI tools within minutes of launch, why he treats his work like an “AI factory,” and the big idea of the episode: in the past, go-to-market was a wrapper around the product — today, the product is a wrapper around the go-to-market. He walks through how that plays out across his own products (paid ads, freemium, and a niche community play), and then turns it on my business, Castos, to show what the “obvious future” of a commoditized category looks like. Chapters 0:00 Noats and local-first meeting notes 4:10 What it really takes to run local models 6:28 Why model training is still a black box 10:22 Where are the US open-weight models? 11:55 Local vs. frontier: how Hiten actually works 13:18 “X is where everything breaks” — evaluating new AI tools fast 15:46 Do you really need to switch tools every week? 18:16 Big-company AI vs. startups for personal productivity 20:39 How to think about growth for an AI product 24:24 The product is now a wrapper around go-to-market 26:30 Does every product need a free tier? 29:19 Coming back to Crazy Egg after 20 years 32:16 What’s exciting — and what keeps Hiten up at night 34:47 Finding the “obvious future” of your business (Castos breakdown) 38:22 Why “grow my podcast” is the new job to be done 40:50 What Hiten’s excited about in AI right now 49:17 Wrap-up: pick who you serve Links Noats: https://noats.ai Hiten on X: https://x.com/hnshah Hiten’s weekly Friday calls: https://www.hiten.com/ Castos: https://castos.com Chapters (00:00:00) - Notes app and local model parity with Granola(00:02:08) - Local models, product motion, and go-to-market teaser(00:04:08) - RAM requirements and practical limits of local compute(00:05:50) - Why training is a black box and model 'flavor'(00:09:25) - Chinese-trained models and the search for US open weights(00:11:14) - Personal workflow for testing new models and Twitter as signal(00:15:42) - Setting up systems to experiment like a factory(00:18:03) - Muse vs startups: trust, security, and Meta's advantage(00:20:32) - Notes go-to-market and distribution strategy(00:24:22) - Product as a wrapper around go-to-market(00:28:29) - Flexibility across enterprise vs consumer go-to-market(00:29:10) - Returning to Crazy Egg and AI-driven efficiency(00:32:09) - Obvious futures: websites that change themselves(00:34:49) - Finding your business's obvious future: Castos case study(00:37:43) - Podcast platforms needing to drive growth, not just hosting(00:40:52) - Excitement about agent tools: Muse, Grokbot, Instinct comparisons(00:47:17) - Differentiation, distribution, and closing thoughts

What does it take to turn an audience into a business—and how do you do it without losing the enjoyment that got you started? This week on Rogue Startups, Craig and Colin compare notes on building creator businesses. Colin shares what he’s exploring after selling his business, including his golf content, sponsorship opportunities, and fractional roles. Craig talks about growing his YouTube channel toward 25,000 subscribers and building a second revenue stream through ads and brand partnerships. We dig into the gap between getting views and building a business: growing an email list, creating relevant lead magnets, nurturing subscribers, and developing your own products. We also explore how to find a clear coaching niche by combining your skills and experience—and why honest feedback from your team can help you focus on the work where you add the most value. Then we get practical about YouTube growth and podcast repurposing. We discuss strong premises, titles, thumbnails, and why the first minute deserves so much attention. We wrap up with how AI tools are changing content production and software businesses, including the opportunities—and uncomfortable questions—that come with automating work you once paid people to do. Fittingly, this episode includes an intro reflecting on using Codex and DaVinci Resolve to edit the conversation itself. Talking points: Building a creator business without turning a hobby into a chore. Monetizing through sponsorships, brand deals, and fractional roles. Why smaller audiences can still be valuable to sponsors. Turning podcast and YouTube audiences into newsletter subscribers. Using lead magnets, segmentation, and your own products to build more predictable revenue. Finding a coaching niche through a distinctive combination of skills. Asking your team where you can contribute most effectively. Giving each piece of content a clear job: views, subscribers, or revenue. Creating stronger YouTube hooks, titles, thumbnails, and opening minutes. Repurposing podcast conversations into standalone videos with custom intros. Using AI to streamline editing, copywriting, and publishing. How changing customer needs could reshape SaaS and service businesses. Subscribe to Rogue Startups wherever you listen, and subscribe on YouTube for future episodes. Follow Craig @thecraighewitt and Colin @colinmcgray on social media. Let us know what you thought of the AI-edited episode—and which practical AI workflows you’d like us to explore next. Get goodies via email: https://craighewitt.kit.com/a7a6c4b5ef

AI agents are getting a lot more capable, but are they actually making work easier yet?  Craig and Colin compare their latest experiments with GrokBot, Hermes, OpenClaw, Claude Code, Codex, and other AI tools, including what works, what breaks, and where agents are genuinely reducing cognitive load.  They dig into open vs. closed systems, shared company agents, local AI, model costs, and the idea of an AI chief of staff that keeps founders focused.  Plus, Colin shares how he's using AI to overhaul a 15-year-old WordPress site, and they explore what the next generation of AI-powered websites and marketing tools might look like. Highlights from Craig and Colin’s conversation: Open vs. closed AI agents for running a business Why Craig chose Hermes as Castos' shared company agent The security challenge of giving AI agents real power Why AI should reduce cognitive load, not create more work How Colin uses AI for CRM, task management, and daily planning Claude Code vs. Codex, Cursor, and other AI development tools Why expensive AI models aren't always the best choice The case for running AI locally or privately How cheap AI access encourages founders to experiment Can an AI chief of staff actually keep you focused? Using AI to overhaul a 15-year-old content site How tiny AI-built tools could replace traditional lead magnets Resources and Links from This Episode: Produced by Castos Productions: https://castos.com/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: [email protected]  Find me on Twitter: https://twitter.com/TheCraigHewitt  LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/  Email: [email protected] Chapters (00:00:00) - Intro and topic setup: bots and agents(00:01:23) - Open vs closed agent platforms(00:03:35) - Why choosing Hermes for a shared team agent(00:07:07) - Permissioning and security challenges with Hermes(00:09:08) - Vision for AI teammates across a company(00:10:44) - Personal use: Grokbot vs Claude code workflows(00:12:53) - CRM, task management, and cognitive load reduction(00:16:09) - Mobile workflows, Notion, and GitHub syncing(00:19:06) - App preferences: Claude vs Codex vs Cursor vs Antigravity(00:22:00) - Right-sizing models and cost discipline(00:22:19) - Golf video workflow and downgrading models to save cost(00:25:33) - Local and private AI compute considerations(00:29:35) - Enterprise API costs, subsidies, and sovereignty concerns(00:32:35) - Value of experimentation under usage limits(00:33:56) - Chief of staff model and multi-agent orchestration(00:37:59) - Chief of staff for managing priorities and stale projects(00:41:25) - Old-school business plans teaser(00:42:01) - Renovating lawns4u.com with AI agents(00:45:00) - WordPress vs modern stacks (Astro, Next.js) discussion(00:47:33) - Building tools and lead magnets beyond WordPress(00:50:15) - Wrap up and future topics

Do you need a team to build a successful company these days? On this episode of Rogue Startups, host Craig Hewitt (Castos) and co-host Colin Gray (Alitu and The Podcast Host) tackle one of the biggest questions facing founders today: how do you hire in the age of AI agents?  Craig and Colin chat about what an "ideal" team looks like, which roles are still worth hiring for, and which ones AI agents can take over (to save more important tasks for humans). They dig into how their own hiring processes have changed and evolved, from async video interviews to paid work samples and screen-recorded tasks. They also explain why a candidate's CV matters far less than watching them think through a problem. Highlights from Craig and Colin’s conversation: Why you might still want a team, even if you don't need one What a minimal modern software team looks like What founders should never fully hand off How AI agents are changing customer research The best first hires for growth and partnerships Why every hire should be an AI power user How to spot great candidates beyond the CV Using paid work samples and screen recordings in hiring The hidden costs and risks of hiring overseas Why EORs and Merchant of Record services can simplify global hiring and sales When to hire a human vs. build an AI agent The trade-offs of staying solo with AI vs. building a team Resources and Links from This Episode: Produced by Castos Productions: https://castos.com/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: [email protected]  Find me on Twitter: https://twitter.com/TheCraigHewitt  LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/   Email: [email protected]

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: [email protected]  Find me on Twitter: https://twitter.com/TheCraigHewitt LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/  Email: [email protected] Chapters (00:00:00) - Rogue Startups: The Search for a Co-Founder(00:00:50) - Getting back in the groove of running(00:03:04) - Talking Business With My Partners(00:04:35) - Does a Co-Founder Need a Partnership in AI?(00:09:00) - Craig Menear: Coaching With Single Founders(00:11:49) - What is a Co-Founder's Decision on Partnering?(00:13:15) - What kind of areas of consideration did I miss besides equity pay,(00:17:46) - Ideas for a Good Co-Founder Relationship(00:19:43) - Have You Ever Shared Options With Your Team?(00:21:44) - How was the, I don't know, the vibe with the(00:23:00) - Is Having a Co-Founder Better Than Being a Solo Founder(00:27:00) - What's The Big Benefit of Starting a Company Solo?(00:30:01) - Does the Company Have a Co-founder Type Role?(00:34:21) - Good Hires vs. Bad Hires(00:36:02) - I love working with a team

What happens to marketing when AI can create almost unlimited content, build software in days, and make it easier than ever for anyone to compete? In this episode of Rogue Startups, Craig Hewitt and co-host Colin Gray dig into what actually works in marketing today. They explore founder-led marketing, “personal brands” (and why that term makes Craig cringe), content strategy, YouTube, newsletters, podcasts, and the growing importance of creating content that carries a real human voice. Craig and Colin debate whether blogging still matters, why YouTube may be the strongest starting point for a new brand, and why podcasts are better at building trust than converting cold audiences. They also discuss the marketing FOMO that causes founders to chase every new platform, the value of in-person events, and how to build a content flywheel where one conversation can become videos, newsletters, blog posts, and social content. The conversation ultimately comes back to a simple question: when AI can produce endless content, what makes yours worth paying attention to?  Highlights from Craig and Colin’s conversation: Why the best marketing ultimately has to create a return for the customer How founders can avoid getting trapped by marketing FOMO Why founder-led marketing may matter more as AI creates more faceless businesses How to figure out what makes you genuinely different Why YouTube may be the best starting point for building a modern personal brand Whether blogging and SEO still have a place in an AI-generated content world Why real stories, experiences, and opinions can make content stand out from AI-generated material How to turn one podcast conversation into a complete content ecosystem Why podcasts are better at building trust than converting cold audiences The underrated marketing power of in-person events and relationships How to build a YouTube and newsletter flywheel Why paid advertising could become more accessible through AI-powered tools Resources and Links from This Episode: Produced by Castos Productions: https://castos.com/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: [email protected]  Find me on Twitter: https://twitter.com/TheCraigHewitt  LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/  Email: [email protected] Chapters (00:00:00) - The Podcast Is Dead(00:00:42) - Rogue Startups: More Money, Stupid(00:02:31) - Podcast Marketing: The Business of Podcasting(00:07:12) - Likely More Personal Brand than Social Marketing(00:09:46) - Developing a Personal Brand(00:13:52) - How to build a personal brand on a platform(00:17:22) - How to Build a Modern Business on the Web(00:23:34) - How Long Form Writing Is Made(00:24:25) - How to Promote Your Podcast and YouTube Videos(00:30:32) - milo on 'Physics'(00:30:50) - How to Promote your YouTube Videos on a Podcast?(00:37:08) - In the World of In-Person Events(00:38:35) - How to Market Your Podcast at Events(00:41:24) - Golf Star on His Next Thing(00:41:41) - How to Build a YouTube Channel and a Podcast(00:45:28) - What's Your First Channel for AI?(00:47:16) - Paid Advertising: The Future of AI(00:48:40) - Episode 1

AI has made building software dramatically easier. But if everyone can build a product, what happens to SaaS? In this episode of Rogue Startups, Craig Hewitt is joined by co-host Colin Gray for a wide-ranging conversation about what they're building, how AI is changing their businesses, and why the biggest challenge for SaaS founders may no longer be writing the code. Colin and Craig dig into AI-assisted development, content repurposing, YouTube strategy, AI agents, memory and context, and the increasingly blurry line between building a product and simply building something for yourself. The conversation gets especially interesting as they compare tools like Cursor, Claude, Codex, Grok, OpenClaw, and Hermes, and discuss the idea of having an AI "boss" that can remember your priorities, surface old ideas, manage your tasks, and push information to you instead of making you constantly hunt for it. Highlights from Craig and Colin’s conversation: How AI is making software dramatically easier to build - and why that creates a new challenge for SaaS founders Why AI tools become much more powerful when they're customized to your specific workflows Is "anyone can build this" becoming a real problem for SaaS companies? Why the hardest part of building software may no longer be writing the code The biggest risk of AI-built software: building something nobody actually wants How Craig and Colin are using AI agents to reduce cognitive load and manage their work Why your AI assistant may need access to your entire digital life to be genuinely useful Turning conversations and existing content into a repeatable publishing workflow Why sometimes a solo founder just needs an AI boss Why more features aren't always the answer for a growing SaaS business What should an AI assistant actually remember about you? How AI agents could change the way founders work, prioritize, and make decisions Resources and Links from This Episode: Produced by Castos Productions: https://castos.com/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: [email protected]  Find me on Twitter: https://twitter.com/TheCraigHewitt  LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/  Email: [email protected] Chapters (00:00:00) - What's the Risk of Building a SaaS in Claude Code(00:00:28) - Rogue Startups: Updates on AI(00:05:07) - How to Build a Podcast on YouTube(00:10:12) - How to hire a non-technical developer(00:15:19) - Cursor Cloud vs. Grokbot: What's The Difference(00:19:46) - Grokbot and OpenCluster: The One Place for Everything(00:25:00) - How Do You Keep Yourself Organized?(00:30:50) - Working on a 6 week plan(00:34:27) - Pushing the pace of product development(00:36:58) - Ideas on Grokbot: The Knowledge Librarian(00:42:47) - Your Bots: Do Your Job(00:43:29) - How to Organize Your Brain in 2019(00:45:11) - OpenClaw vs. Codex: Which is better?(00:47:34) - Colin Gray on Social Media

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: [email protected]  Find me on Twitter: https://twitter.com/TheCraigHewitt  LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/   Email: [email protected] 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

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: [email protected]  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

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: [email protected] Find me on Twitter: @TheCraigHewitt  Twitter: @TheCraigHewitt  LinkedIn: Craig Hewitt  Email: [email protected] 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?

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: [email protected]  - 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

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

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: [email protected]  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: [email protected]  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

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: [email protected]  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