Craig Hewitt

Rogue Startups

A Entrepreneurship , Business and Technology podcast

#73 in Entrepreneurship · 🇮🇪 #93 in Entrepreneurship · 🇿🇦

About the show

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.

Newest episodes

Why Enterprise Deals Die w/ Marc Thomas

Nov 11, 2026 47 min

Craig Hewitt sits down with Marc Thomas, a consultant who works on lifecycle marketing, to talk about what it feels like to run a business while AI changes the ground under everyone's feet. Both swing between optimism and pessimism from one day to the next. They look at where founders should put their marketing effort, what has happened to SEO and content, whether AI personas are worth building, and what AI might mean for their kids' working lives. Topics discussed Why the constant stream of tech and AI news feels like a fire hose, and why the highs and lows come so fast Outcome-based pricing, where customers pay when they are satisfied with the result, and Marc's experience paying for credits in a tool he tried Trust, switching costs and why reputational risk stalls big enterprise deals more than price does Craig's scale of AI adoption, and where he puts his own business on it The worries founders have as AI improves: customers building their own product, retention and upsell, and finding new customers Acquisition versus getting more from your existing list, with a CRM-for-window-cleaners example Why SEO and content no longer work the way they did, and how AI search favours established brands Organic social, and what happens when you build an AI avatar or AI persona Kids, college, layoffs and what work might look like in the future A book recommendation: Before the Deluge, and the parallels Marc sees between 1920s Berlin and today Key takeaways Marc's view: big enterprise deals depend on a champion inside the organization, and looking after that person matters more than price. His rule of thumb for acquisition: if you are below a million dollars of annual revenue, put your focus on acquisition; beyond that, getting more from your list matters more unless your list is huge and converts very poorly. Craig says SEO and content were a fantastic way to acquire customers and that taking that away is a big deal for the bootstrapped SaaS world. Marc's approach to the A...

Is the SaaSpocalypse Over?

Oct 22, 2026 43 min

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 bi...

Your Product Is Now a Wrapper Around Go-To-Market | Hiten Shah

Oct 13, 2026 50 min

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...

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All episodes

Why Enterprise Deals Die w/ Marc Thomas

Nov 11, 2026 47 min

Is the SaaSpocalypse Over?

Oct 22, 2026 43 min

Your Product Is Now a Wrapper Around Go-To-Market | Hiten Shah

Oct 13, 2026 50 min

From Audience To Income

Sep 29, 2026 56 min

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 m...

RS368: Grok Bot & Hermes

Sep 22, 2026 50 min

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: 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) - 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 chall...

RS367: How to Hire in the AI Era

Sep 15, 2026 48 min

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

RS366: When (and how) To Pick a Co-Founder

Sep 8, 2026 41 min

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.thepodcas...

RS365: Marketing that Actually Works Today

Sep 1, 2026 48 min

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 Link...

RS364: Think Less, Do More

Aug 25, 2026 48 min

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/p...

RS363: Why Talking to AI About Your Business Is Dangerous

Aug 18, 2026 32 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...

RS362: Hidden Multipliers with Jason Cohen

Aug 11, 2026 50 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 way...

RS361: Lessons Learned Selling A Business

Aug 4, 2026 46 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 B...

RS360: Kill the Hippo

Jul 29, 2026 43 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 Featur...

Huge Work (and life) Updates

Jul 21, 2026 14 min

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

RS358: Your Design Sucks

Mar 18, 2026 54 min

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, qu...

RS357: I Got Hacked

Mar 11, 2026 44 min

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...

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

Mar 4, 2026 1 hr 2 min

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 e...

RS355: Code Velocity and the Future of SaaS

Feb 25, 2026 58 min

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 C...

RS354: The State Of Podcasting Heading Into 2026

Nov 26, 2025 41 min

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 Se...

RS353: Is This the Last Organic Marketing Channel

Oct 1, 2025 50 min

In 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 Chapters (00:00:00) - Interview With Builder Methods's Brian Castle(00:00:40) - 100 Days of AI: How to Write a Week...

RS352: AI Killed Traditional Marketing – Here's What's Next

Sep 24, 2025 49 min

Ross 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 Chapters (00:00:00) - Ross Simmons on Marketing in the Era of AI(00:01:31) - What's Working For B2B & SaaS?(00:04:53) - In the Elevator With Tim Ferriss(00:05:24) - Marketing Cycle: Is It Really Different This Time?(...

RS351: Why Brands Fail on Reddit

Sep 17, 2025 45 min

Today on the podcast, Craig sits down with Reddit marketing expert Paul Xue to explore how brands can tap into one of the internet’s most engaged and skeptical communities. Reddit can be a tough nut to crack, but when approached with authenticity and a strategic approach, it can become a powerful driver of trust, visibility, and growth. Paul, founder of his own marketing company specializing in Reddit campaigns, breaks down the principles, tactics, and future trends you need to know. Whether you’re curious about launching your first campaign or wondering if Reddit should be part of your overall growth strategy, this episode is packed with practical insights, not to mention a few insightful predictions on the future. Highlights from Craig and Paul’s conversation The fundamentals of Reddit marketing: why content and value must come before sales. How authentic reviews and real conversations build credibility with both competitors and customers. Proven strategies to run successful Reddit campaigns without getting downvoted. Ways to make your brand stand out in Reddit’s crowded, skeptical landscape. The future of AI models and how they’ll shape online marketing. Big-picture insights on AI, robotics, and what a fully autonomous future could look like. Resources and Links from This Episode Paul’s LinkedIn: https://www.linkedin.com/in/pxue/ Paul on X (Twitter): https://x.com/pxue?lang=en Castos Free Tools: 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 #AI #marketing #reddit Chapters (00:00:00) - How to Market Your Brand on Reddit(00:00:59) - Paul on Reddit Being Soulless(00:01:3...

RS350: Authenticity, Content Strategy, and the Future of Marketing with AI

Sep 10, 2025 57 min

Startup marketing can feel like a maze, right? In this episode of Rogue Startups, Craig chats with Brendan Hufford of Growth Sprints about how to cut through the noise and actually connect with your audience. They dig into everything from creating raw, authentic content to dialing in your SEO strategies and uncovering your brand’s real voice. If you’ve ever felt a little lost with your marketing (or just want some fresh ideas to make your plan actually work), this episode is packed with insights you won’t want to miss. Highlights from Craig and Brendan Hufford’s conversation: AI in SEO: how artificial intelligence is reshaping the digital marketing landscape Why old methods don’t work anymore—and the mindset shift needed to move forward Building new skill sets: why continuous learning is essential for marketers and founders Staying ahead of the curve with new tech, trends, and tools How entrepreneurs can use AI to market their businesses more effectively Content atomization and distribution: breaking big ideas into bite-sized content across multiple channels Maximizing social platforms like Instagram, Twitter (X), and more “Zero-click content”: how to thrive on platforms that discourage external links Optimizing for virtual retargeting and platform-native algorithms Overcoming the “trust recession” and rebuilding credibility with your audience Turning one-star reviews into marketing gold Creating a gravitational pull that draws customers toward your brand and story The power of self-perpetuating content that continues to work for you over time Why founders shouldn’t try to do everything alone—and how to delegate effectively Finding your authentic founder’s voice and building trust through genuine content Resources and Links from This Episode Brendan Hufford on LinkedIn: com/in/brendanhufford Growth Sprints: https://growthsprints.co/ Email me: podcast@roguestartups.com Find me on Twitter: @TheCraigHewitt If you feel like Rogue Startups has benefited you, and it...

RS349: Ranking In ChatGPT with Devesh Khanal

Sep 3, 2025 1 hr 3 min

Today on Rogue Startups, Craig sits with Devesh Khanal from Grow and Convert to talk about how to get your brand showing up at the top of search results in LLMs. They dive deep into the world of AI SEO—covering everything from debunking myths about large language models to sharing actionable strategies for ranking your content in both Google and AI-driven search tools. Devesh is the “convert” side of Grow and Convert. In addition to co-founding the company, he runs Growth Rock, a conversion optimization agency that helps e-commerce brands increase online sales through user research, usability testing, analytics evaluations, and A/B testing. Before launching into the marketing world, Devesh worked on financial strategy and cost modeling for a biofuels startup—and he also holds a Ph.D. in Materials Science and Engineering from U.C. Berkeley. Highlights from Craig and Devesh’s conversation: Bottom-of-funnel SEO vs. top-of-funnel queries How to use LLMs as a marketing tool Debunking common myths about LLMs in SEO Does community content promotion (like Reddit) actually work? The correlation between Google rankings and LLM results Identifying customer pain points and achieving product–market fit Why to avoid “fluff” writers and generic AI writing tools Resources and Links from This Episode: Devesh Khanal on LinkedIn: https://www.linkedin.com/in/deveshkhanal/ Grow and Convert: https://www.growandconvert.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: Chapters (00:00:00) - How to get your brand to show up in ChatGPT or(00:01:21) - Why Our Traffic's Down 50% vs. 2 years ago(00:08:29) - ChatGPT's Google Rankings(00:09:47) - Push...

RS348: Not Exactly White Hat AI-SEO with Lars Lofgren

Jul 16, 2025 53 min

In today’s episode, Craig sits down with AI-SEO expert Lars Lofgren to unpack the future of AI-SEO in a world dominated by artificial intelligence. They explore how to attract and retain traffic through both on-site and off-site strategies like Reddit, YouTube, LinkedIn, and beyond. With AI rapidly reshaping the digital landscape, the traditional rules of content and inbound marketing are being rewritten. Should SEO still be your top focus? How do you build brand authority when search algorithms are changing every day? Tune in for practical tips and bold insights on what’s working now—and what’s next. Highlights from Craig and Lar’s conversation: What does SEO even mean in the age of AI? How the search landscape has shifted with AI’s rise The #1 thing to do now to thrive in AI-powered search results Top of Funnel (TOFU) vs Bottom of Funnel (BOFU) marketing Why Google prioritizes specific landing pages for specific products The companies gaming AI—and how it’s disrupting traditional SEO How to get your brand seen in AI answers and social media feeds The surprising impact of Reddit on SEO strategy Why SEO best practices feel more unclear than ever Authentic content vs high-volume output, what wins with AI? Building trust: How to make your site feel real to your visitors Ads, paid influencers, evangelists: what actually pays off? Resources and Links from This Episode Lars on LinkedIn: https://www.linkedin.com/in/larslofgren/ Lars’ website and newsletter: https://larslofgren.com/ Lars on BlueSky: https://bsky.app/profile/larslofgren.bsky.social Lars on Twitter/X: https://x.com/larslofgren?lang=en Find me on Twit... Chapters (00:00:00) - Interviewing Lars Lofgren on AI-SEO(00:01:20) - What to Call AI SEO?(00:03:23) - SaaS Companies: The AI SEO Challenge(00:05:56) - Top of the funnel and AI in the SEO(00:09:57) - SEO Training: Bottom of the funnel vs(00:12:43) - What's The Difference Between a Keyword and a Topic?(00:16:10) - Is Content Still the Only Way to Win...

RS347: How to Rank Any Brand In AI Results

Jul 9, 2025 47 min

This week on Rogue Startups, Craig chats with Mike Buckbee from Knowatoa about how AI is changing the game for brands. With tools like ChatGPT taking over the way we search and discover businesses, Mike breaks down what you need to do to get your brand noticed in the AI world. From content strategies to getting your site in front of the right eyes, this episode’s got the lowdown on how to stay ahead in an AI-driven world. Michael is a serial entrepreneur and software developer who has founded multiple successful startups in the cybersecurity space. With over a decade of experience in marketing and technology, he previously worked as a Director of Demand Generation for a public cybersecurity company, as well as consulting for multiple YC startups. Knowatoa’s mission is to help businesses win the AI search game by ensuring they remain discoverable, relevant, and competitive in a rapidly evolving digital landscape. Highlights from Craig and Mike’s conversation: How to get your business in front of customers in the AI-driven world New strategies for success: creating brand-specific content that attracts customers What "Face vs Space" content really means Where AI is training and how it impacts businesses The role of txt: Is it still important, and what’s the best alternative? Why you should ask ChatGPT questions about your business Personalized AI search results: Are they working for or against you? Why your content should be on YouTube, LinkedIn, and Reddit The growing role of LLMs in social etiquette and advice How search, companionship, and advice are blending in the AI space What does all this mean for businesses in the future? The future of business is pay-to-play Will AI take 30% of our jobs? The "floor" may rise, but the "ceiling" will stay human Resources and Links from This Episode Knowatoa: https://knowatoa.com/ Mike on LinkedIn: https://www.linkedin.com/in/michaelbuckbee Email: Mike@knowatoa.com If you feel like Rogue Startups has benefited you and...

RS346: What 11 Years in SaaS Really Looks Like

Jul 2, 2025 48 min

In this episode of the podcast, Craig sits down with longtime entrepreneur Colin Bartlett, cofounder of StatusGator, to explore what it really takes to build, and sustain, a SaaS business over the long haul. With more than a decade at the helm of a company that helps users monitor service outages, Colin shares hard-won insights from 12 years of entrepreneurship and 11 years of running StatusGator. The conversation dives into how founders’ perspectives evolve, especially in today’s turbulent tech landscape, and how to stay grounded and successful through all of that craziness. Highlights from Craig and Colin’s conversation: How Colin and StatusGator did when Google Cloud went down for a few hours The factors that can determine whether or not free trials can work for your business The difference between the company in the beginning versus 10+ years down the road How their businesses fit into the current markets (alongside AI and other tech advances) Appreciation and respect for the businesses in such uncertainty Plans, trajectories, and what the future holds for them Views on profit in the SaaS industry Their team structures and how to hire and maintain a team in the AI era Staying fresh in the market after you’ve been in the business for a while The benefits of having a cofounder SOC 2 (System and Organization Controls 2) compliance and privacy standards How many hours does your team have to work to be a value to your company? Resources and Links from This Episode Colin Bartlett on LinkedIn: https://www.linkedin.com/in/colinabartlett/ StatusGator: https://statusgator.com/ 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) - Talking...

RS345: The State Of Search 2025

Jun 11, 2025 18 min

- LLMs.txt article: https://www.quoleady.com/llm-txt-files/ - Craig's YouTube channel: https://youtube.com/@thecraighewitt Chapters (00:00:01) - Rogue Startups: The Startup Podcast(00:00:07) - Content Marketing: Multimodal(00:03:37) - Is Content Necessary for Your Business?(00:06:23) - How to get a crawler to crawl your website for SEO(00:13:58) - Marketing Decoded: Content and Search(00:17:14) - Want to hear more of my ranting on AI?

RS344: 12 Years to Overnight Success with Amar Ghose

Jun 4, 2025 47 min

What does it really take to lead a company for over a decade—and still be growing? In this episode, Craig chats with Amar Ghose, founder and longtime CEO of ZenMaid, about the challenges, lessons, and evolution that come from running a SaaS company for 12 years. From market leadership and internal conflict to personal growth and productivity, Amar shares candid insights into the realities of long-term entrepreneurship. Whether you're scaling a startup, feeling stagnant in your leadership role, or just wondering if AI is going to eat your SaaS lunch, this conversation delivers. Highlights from Craig and Amar's conversation: Transitioning from following trends to becoming a category leader Navigating internal disagreements and managing tough decisions Running a "benevolent dictatorship"—and why that sometimes works How to deal with boredom, complacency, and staying sharp as a CEO The productivity paradox: what being "productive" means at the top Entertainment vs. distraction: protecting your focus How coaching reveals your blind spots (and helps you evolve) Staying out of cruise control—how to keep leveling up, year after year Is AI a threat to SaaS companies, or a tool for growth? Takeaways and Vision Longevity in SaaS isn’t about coasting. It’s about evolving. Amar Ghose proves that staying in the game for 12+ years means embracing discomfort, sharpening your focus, and leading with intention. Whether you're one year in or a decade deep, this episode is a reminder: real leadership isn’t about avoiding boredom, it’s about leveling up through it. Resources and Links from This Episode ZenMaid – Amar’s SaaS for maid service businesses Follow Amar on LinkedIn Rogue Startups Podcast Archive Connect with Craig on Twitter/X: @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...

A Caffeine Infused Diatribe

May 28, 2025 46 min

Hello, remember me? Sorry that it's been 6 weeks, but I'm back. In this episode I talk through what I've been up to recently, what's going on with Castos, with myself personally, and things I'm learning growing the business. Towards the end, I share the lessons I learned from a recent 2-day Scaling Workshop with Alex and Leila Hormozi. The event was great, and really reframed how I am thinking about the business, and about being a business owner. My YouTube channel: https://youtube.com/@thecraighewitt - for sales, marketing, and founder-focused content like this. Chapters (00:00:00) - What's Up With Me(00:00:38) - Top Creators: AI and How to Use It(00:06:21) - How We're Going to Implement Hybrid Podcasting(00:10:36) - How I'm Using AI on My Personal Channel(00:14:27) - Writing Content Is Dead on Social Media(00:17:43) - A Retrospective on The Kastos Scaling Workshop(00:18:43) - Interview(00:19:14) - The Warren Buffett Lecture(00:21:19) - Six Metrics That Make Up My Business(00:23:17) - Top Executives: Paid Acquisition(00:24:39) - Keeping Person in the Business(00:25:42) - What is the Key Customer Risk?(00:27:16) - Key Market Risks(00:29:15) - Sales Funnels and How to Manage Them(00:30:37) - How to Get More Out of Your Work Life(00:31:40) - How to Scale a Startup: The Castos(00:34:01) - The Four R's for Job Description(00:35:04) - How To Get Feedback From Your Sales System & Culture(00:37:12) - What They Look For In Their CRM Hiring(00:38:54) - Sales and Marketing: The Middle of the Revenue Cycle(00:42:21) - Castos: How to Make Paid Acquisition Work(00:45:28) - The Time Evaluation Workshop

RS342: SaaS Survival Mode - AI, Niches & Navigating Chaos

Apr 23, 2025 45 min

In this episode of Rogue Startups, Craig chats with Jesse Hanley, marketer, self-taught developer, and founder of Bento, a powerful email marketing platform for modern teams. With today’s economy in flux and global events adding more pressure, Craig and Jesse dive into what it really means to run and grow a SaaS business in 2025. They explore how entrepreneurs can protect their businesses and families in turbulent times, why niching down is more important than ever (but only for some), and how AI is transforming both Bento and Craig’s own company, Castos. From global living experiences to making tough decisions about free tiers, this episode is packed with honest insights, practical advice, and a few spicy takes on the future of SaaS. Highlights from Craig and Jesse’s conversation: Living and working in Japan, France, Australia, and the US: cultural and business differences Bento’s vision and how they are navigating economic uncertainty Knowing when to bring in experts (and when to trust your gut) How Bento is integrating AI—and how it’s driving real results for users Behind the scenes at Castos: using AI to boost productivity and creativity Are free plans a growth hack or a trap for SaaS companies? Marketing smarter: finding your ideal customers in a crowded market To niche or not to niche? What to do if your product is a Swiss Army knife If you’re a SaaS founder, bootstrapped entrepreneur, or just love behind-the-scenes looks at real businesses navigating real challenges, this episode is for you. Resources and Links from This Episode Jesse Hanley on Twitter/X: https://x.com/jessethanley Bento: https://bentonow.com/ 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: Chapters (00:00...

RS341: Microconf 2025 Recap

Mar 26, 2025 17 min

Craig recaps his biggest takeaways from MicroConf 2025, reflecting on lessons in positioning, lead generation, conference ROI, and the power of going all in on what’s working. From tactical marketing insights to personal reflections, this episode delivers both strategic clarity and founder fuel.

RS340: Is AI Killing SaaS w/ Tim Schumacher

Mar 19, 2025 43 min

In this episode of Rogue Startups, Craig sits down with founder and entrepreneur Tim Schumacher to discuss his insights on AI, the future of SaaS, and what makes a company successful. In 2001, Tim co-founded Sedo.com, the world's largest domain marketplace. Since selling the company, he’s been active as an Entrepreneur and/or Investor in various start-ups, such as Eyeo (makers of Adblock Plus), Ecosia, Hitfox, Aklamio, Miomente, PiwikPro, BasicThinking, Home, Zolar, Joblift, SaaS.group, and others. Highlights from Craig and Tim’s conversation: The future of SaaS keeps founders up at night Using artificial intelligence to analyze feedback and company metrics for smarter decision-making How to make your data, and your customers' data, available across multiple platforms and environments What impact will AI and automation have on the economy and the future of work? Why are some in the SaaS industry still hesitant to adopt AI, and what are their fears? Key factors that drive business growth and longevity. Product-Market Fit vs Founder-Market Fit: Understanding the difference and why both matter. Starting a business at the intersection between climate tech and AI Remote work vs in-office culture: How the workplace dynamic is evolving in the age of digital transformation. Resources and Links Mention in This Episode: Tim on Twitter/X Tim on LinkedIn Email: tim@saas.group Sedo Zenloop Day.ai Fyxer 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:

RS339: AI Skeptic, or Believer

Mar 5, 2025 47 min

In today’s episode, Craig chats with Anthony Eden from DNSimple about how they use AI in their businesses and their personal lives. As early skeptics of AI, they do a deep dive into what made them change their minds, what AI does for them, and how it might actually be holding people back. Like the internet, AI is a powerful tool people can use to make their lives better. They also chat about what it’s like to raise kids as entrepreneurs. Has their influence improved or hindered their children’s lives? Not to mention, how do they balance their work life and personal life and is AI helping them with that balance? Anthony Eden is the creator and founder of DNSimple. He has been developing web applications since the early days of the web (1995) using Ruby, Erlang, Golang, and other languages. He used to publish a podcast called the Strong Businesses Podcast with Steven Bristol. He also published a mostly weekly podcast of progressive dance music over at theministerprime.com. He also produces tracks which can be found on SoundCloud. Highlights from Craig and Anthony’s conversation: What changed Anthony and Craig’s minds about AI How to, as an entrepreneur, leverage AI without just “chasing the trend” The personal and emotional impacts of running a business in this AI world What AI will do for the future of business and SaaS Training AI and what the “mistakes” teach you and your team “I have to have a little bit of fear in everything I do [as a founder].” Keeping customer data safe and secure What data is AI using to aid you with your business? “This kind of stuff is fantastic but, boy, does it make you lazy.” As an entrepreneur, how do you talk to your kids about careers after college? How is generative AI going to make our lives better? Takeaways and Vision: How do you take a non-native AI solution and adapt it to a solution for your customers, your team, and your business? As a founder and entrepreneur, how you use AI in your business is important. Not only do yo...

RS338: Balancing Your Use of AI with Aaron Francis

Feb 26, 2025 52 min

Ever wonder what's happening behind the scenes when your dev team says they're "leveraging AI"? As a non-technical founder, you don't need to understand every line of code, but knowing how AI is actually being used in your business is becoming essential. Today I'm sitting down with Aaron Francis, who pulls back the curtain on AI in development work. We'll explore the surprising differences between how veterans and newcomers in the field are using these tools, the common pitfalls teams fall into, and the unexpected ways AI is transforming how products get built. Whether you're trying to speak your developer's language or just want to ensure your company is using AI effectively, this conversation will give you the insights you need. Highlights from this Episode: Are junior developers utilizing AI too much? Creating a balance between overusing AI and being a Luddite How Aaron uses Claude for “discrete” tasks Developers aren’t going away anytime soon Balancing the use of AI without depending too much on it Harnessing the power of AI for your business AI tools are both calming and scary for founders Aaron’s different uses for 01 Pro What AI can do versus what AI should do and undeniably human tasks Where to go to educate yourself about AI The importance of testing and checking AI work Resources and Links from this Episode: Try Hard Studios: https://tryhardstudios.com/ Aaron Francis: https://x.com/aarondfrancis Reforge: https://www.reforge.com/profiles/brian-balfour SWYX: https://x.com/swyx https://www.youtube.com/@JeffSu https://www.youtube.com/@SkillLeapAI https://www.youtube.com/@MATGpod Email me: podcast@roguestartups.com Find me on Twitter: https://twitter.com/TheCraigHewitt

RS337: Building AI Native SaaS w/ Jordan Gal

Feb 5, 2025 48 min

Today, Craig chats with Jordan Gal from Rosie about starting a business centered solely on AI. While many of us use AI to help with our work tasks and streamline certain jobs, Jordan’s whole business is AI. They discuss how you and your customers can use AI, what it’s like to start a company right now, and what AI is doing to SaaS. Rosie creates a new option for small businesses. Previously, the only way to handle phone calls during work hours was through voicemail or an answering service. Rosie offers a new option in that market: an AI can answer the phone for you and handle the tasks needed for these calls, whether it’s taking messages, sending messages out, or talking to clients. Highlights from Craig and Jordan’s conversation: Non-technical CEOs sympathize more with customers Jordan views his engineering company as customers see their product Because of this, he knows how Rosie helps businesses run better Using AI to help the customer understand their data vs building a product that was not possible before AI Create milestones for the team when creating a brand-new product Jordan tells his team to work as if they are onboarding 100 customers a day Dealing with customers that have different knowledge bases of your type of product Remove marketing fluff to speak plainly to possible customers If you provide the customer with something they truly need and get value from, they will find ways to deal with those roadblocks Conversion versus usage numbers: how to avoid churn Freemium and usage-based trials What AI has done to SEO: people are led to video and YouTube Software in the AI era Now is a good time to bootstrap; it is not a good time to raise money Everything you do has to have leverage Takeaways and Vision: Everything in technology is time-sensitive because tech improves and evolves so fast. Rosie shows us that AI can do much more than just answer questions, run some numbers, and analyze data. Whether you’re using AI to help your business run better,...

RS336: Claude Project Deep Dive with Alison French

Jan 29, 2025 47 min

On today’s episode of Rogue Startups, Craig continues his AI series with founder, marketer, and Claude-user Alison French. They discuss the hesitation creators feel when working alongside AI and what Alison did to overcome that hurdle. Since then, she’s taught herself how to use Claude.ai in her creative and professional work. AI is a tool that everyone has to learn how to use. Watch on YouTube If you feel our podcast has benefited you and might benefit someone else, please share it with them. Also, if you have a chance, please give Rogue Startups a review on iTunes. We’ll see you next week! Highlights from Craig and Alison’s conversation: How creatives can use AI to improve their professional and personal lives How to fine-tune Claude’s tone of voice: Add files to the specific project only You have to feed the machine with information that matters Over time, working within the same project, Claude will tune itself to your prompts How to have Claude see references and change the tone or voice Separate and break down transcripts by prompt to hone in on specifics Claude is like a junior copywriter: work with it and nurture it, and it will help your work go faster so you can focus on the important things. Craig’s creative process when creating content: Get examples/models, templates, and ideas to input into your AI program of choice. Break your content up into different functions. Go in once a week to pull out topics. Put the time and energy into refining one meaty piece of content that you can use over and over again. You have to focus on what makes you credible to your audience How does your team embrace and respond to AI because at the surface it’s a risk for all of us? How do we educate our youth now, for a future with AI? Takeaways and Vision Balancing the importance of human connection with the ability to express your individuality and be yourself is even more possible in this AI era. Adopting and embracing technology and AI in your personal and p...

RS335: Evaluating AI Model Performance with Stuart Grey

Jan 22, 2025 47 min

In today’s episode of Rogue Startups, Craig sits down with AI expert Dr. Stuart Grey to discuss how AI is transforming both his personal and professional life. Dr. Grey also shares how he educates his students and clients on AI applications. He believes AI will play a pivotal role in all of our futures, and while there may be hesitations, AI can be harnessed to create high-quality content and drive innovation. Watch on YouTube Over the next few episodes, I’ll be chatting with folks about the real ways they’re using AI in their businesses. If you’re interested in joining the conversation, hit me up (details below). But for now, here’s a breakdown of how I’m incorporating AI into my own work. Highlights from Craig and Stuart’s conversation: What it’s like to teach AI and machine learning at the university level Comparing AI prompts across different platforms and analyzing results Stuart’s AI Rules of Thumb for efficient content generation Ethical considerations when using AI technologies A glimpse into the near future of AI in everyday life and business The two primary types of AI-driven content creation How to turn basic AI-generated content into exceptional material Takeaways and Vision AI is integrating into our daily lives and everyone needs to learn how to leverage this powerful technology to save time and enhance productivity. Whether you’re just starting or an established professional, understanding how to work alongside AI-powered tools is key to staying ahead in your career. Resources and Links from This Episode Stuart Grey on LinkedIn: https://www.linkedin.com/in/stuartgrey/ Stuart Grey on X: https://x.com/stugrey Stuart Grey’s website: https://www.stugrey.com/ Castos Free Tools: castos.com/tools Email me: podcast@roguestartups.com Find me on Twitter: @TheCraigHewitt Want to Share Your AI Story? I’m looking for guests to share how they’re using AI in their businesses. If you’ve got some great examples or unique insights, reach out to me:

RS334: How AI Saves Me 10 Hours A Week

Jan 8, 2025 15 min

Today, I’m kicking off a series on AI—how I’m using it personally and professionally to grow my business, make life easier, and operate at a higher level. Over the next few episodes, I’ll be chatting with folks about the real ways they’re using AI in their businesses. If you’re interested in joining the conversation, hit me up (details below). But for now, here’s a breakdown of how I’m incorporating AI into my own work. Key Ways I’m Using AI in My Business Content Creation for Programmatic SEO Using OpenAI and Claude to create use case pages for Castos. Built a process to programmatically generate 100+ SEO landing pages using Google Sheets and templates. Example use case: Why Startups Should Start a Podcast for Thought Leadership. Custom GPT for YouTube Scripts Created a custom GPT workflow to script our Castos YouTube videos. Process: Provide a topic, feed it examples, and let GPT draft outlines and scripts. Outcome: High-performing, 90%-ready scripts I tweak and personalize. Building Free Marketing Tools Leveraging tools like Replit and Cursor to develop free tools for Castos (e.g., podcast name generator, social post creator). Focus: Engineering as marketing to drive traffic and lead generation. Documenting Internal Processes Using Loom to record workflows (e.g., triaging support tickets). Leveraging AI to convert videos into detailed step-by-step process documentation (aka playbooks). Automating Low-Level Tasks (Future Plans) Exploring tools like Make and Airtable for automating repetitive processes (e.g., email tagging, Slack notifications). Goal: Free up mental energy for high-value activities like sales, marketing, and strategy. Takeaways and Vision AI is transforming the way we work, and I’m all in on finding ways to integrate it into every aspect of my business. It’s not just about saving time; it’s about leveling up and creating systems that make the impossible possible. I’m inspired by the idea of building something like an 8-person, $10M bu...

RS333: Grading My Business (and yours!)

Jan 1, 2025 22 min

In this New Year's Eve 2024 episode, we dive into a framework for evaluating SaaS businesses across eight crucial criteria. Instead of doing a typical year-in-review or making predictions, we explore how to assess the fundamental strength and potential of your business. Episode Highlights Craig grades Castos (podcast hosting platform) across eight key criteria for evaluating SaaS businesses: 1. Pricing (6/10) - Core product (podcast hosting) averages $28/month - below ideal $50+ threshold - Production services start at $1,500/month - Enterprise clients pay tens of thousands annually - Mixed pricing model affects overall score 2. Churn (9/10) - Extremely low churn rate - Attributes success to: - WordPress integration - Premium pricing (no free tier) - Strong technical reliability 3. Payment Processing Integration (4/10) - Offers multiple monetization options: - Castos Ads - Castos Commerce - Donations - Paid subscriptions - Private podcasting - Limited adoption of direct monetization features - Most customers monetize indirectly through business growth 4. Switching Costs (6/10) - Technically easy to switch providers - High retention due to ongoing necessity - Perceived switching cost higher than actual 5. Technical Advantages - WordPress integration provides unique value - Core functionality similar to competitors - Important lesson: Customer needs often simpler than assumed 6. Expansion Revenue (3/10) - Limited expansion opportunities - Most customers stay at $19/month - Working to add upgrade opportunities - Identified as major growth limitation 7. Established Market Need (10/10) - Clear market position - Well-understood service category - Strong product-market fit 8. Customer Acquisition (6/10) - Success with content marketing, SEO, partnerships - Struggling with paid acquisition - Limited by low price point - Working on improving paid channels Key Takeaways - Overall Business Grade: B (maybe 80/100) - Growth Ceiling: Business could potentially...

RS332: Competing with Stripe and Hubspot (ft. Geoff Roberts)

Dec 25, 2024 39 min

Hey everyone! Just had an awesome chat with Geoff Roberts from Outseta (outseta.com). They're doing something pretty wild - basically smashing together Stripe and HubSpot into one platform for subscription businesses. How cool is that? Quick Hits: - Outseta is an all-in-one platform handling payments, auth, CRM, email, and help desk - They've got this unique setup where everyone makes $210k/year (pro-rated) and can work 1-5 days a week - Took them 4 years to really nail the product (hey, good things take time!) Best Parts of the Convo: - Jeff got real about marketing struggles (who hasn't been there?) - Turns out ChatGPT is actually sending them customers now - wild! - We had a great debate about whether SaaS is still the golden ticket (spoiler: it's way more competitive now) - Talked about why sometimes it's better to stick with a "pretty good" business than chase the next unicorn Where They're Headed: - Aiming for $10M in revenue with a lean team of about 20 people - Shifting from being super product-focused to really pushing growth - Geoff's been at it for 8 years and plans to keep going for 7 more Real talk: This episode is perfect if you're building a SaaS company or thinking about bundling multiple tools together. Geoff drops some serious knowledge about what it's actually like in the trenches. Check them out at outseta.com if you want to see what they're building! #SaaS #Startups #Entrepreneurship

RS331: I'm Still Here...

Dec 18, 2024 9 min

After a 2+ month hiatus, we're back! Watch on YouTube Sorry for the pause in episodes, but thank you for tuning in this week. In this episode I talk through why the forever long break in the podcast, what I've learned in that time, and where things are with me and the business. But most of all, I want to hear from you...what do you want out of this podcast. Hit me up on Twitter, LinkedIn or even Bluesky

RS330: Product-Led Playbook with Wes Bush

Oct 9, 2024 47 min

Wes Bush is a leading authority on product-led growth (PLG) and is here to guide Craig through the playbook for implementing product-led strategies in your business. This episode is invaluable for entrepreneurs eager to understand how product-led growth works, as well as those skeptical about its effectiveness. Listeners will gain insights into the product-led mindset and methodology that Wes employs for successful PLG implementation. Watch on YouTube Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast 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. We’ll see you next week! Highlights from Craig and Wes’ conversation: Differences and Similarities Between Product-Led Growth (PLG) and Self-Service SaaS How to Leverage PLG as a Marketing Tool Internal to External Growth Loops (e.g., Canva) Providing Value and Education to Empower Customers Overcoming the Fear of Change and Embracing Creative Destruction The Product-Led Implementation Program and Wes Bush’s New Book From Contender to Leader: Navigating Your Market Castos: A Case Study in Product-Led Growth A Little About Wes: Wes is an entrepreneur, author, and product-led coach. Over 500,000 people have read his Product-Led Growth book and listened to the ProductLed Podcast. Links & Mentions from This Episode: Wes on LinkedIn Product-Led “Why Nations Fail” by Daron Acemoglu and James A. Robinson Rogue Startups Resources: Follow Craig on Twitter/X Craig on LinkedIn Castos Founder Insights

How To Hire For Growth

Sep 25, 2024 14 min

In this episode of Rogue Startups, I dug into several pressing questions from the community. From knowing when to pull the plug on a marketing channel to the debate around hiring for support versus sales, we covered ground that matters deeply to founders and entrepreneurs. Here’s a breakdown of the key takeaways that can help you level up your startup game. Watch on YouTube 1. When Should You Know if a Channel is Working? A common dilemma many founders face is determining whether a new marketing channel is working. If you’ve ever wondered how long you should invest in a channel before calling it quits, you’re not alone. Here’s how I break it down: Give New Channels at Least 90 Days: If you’re starting fresh with a channel, 90 days is the minimum timeframe to give it. Less than that is almost never enough. Existing Channels Need Time Too: Even for established channels that you’re tweaking or optimizing, 90 days is still a good baseline. After that, look at the data to guide your decision. Focus on Leading Indicators: Whether it’s impressions on LinkedIn, open rates in email campaigns, or early engagement in SEO, you need to assess the leading metrics first. These are the earliest signs that a channel is gaining traction. For example, if you’re working on LinkedIn, impressions tell you whether your content is even being seen. Engagement and DM conversations are steps that follow, but focusing on what starts the funnel will help you decide if you should stick with it. 2. The Support, Success, or Sales Dilemma Another big question I often get asked is, “How do I know whether I need to hire for support, sales, or customer success?” This decision depends largely on where your business is in its growth stage and the roles you want to fill. Support Roles: These are typically more reactive—answering support tickets, maintaining a knowledge base, and troubleshooting. If customers are having common issues, or if onboarding is a bottleneck, it might be time to bring in a...

RS328: Are you Productive or Effective as a founder?

Sep 18, 2024 14 min

Running a business is both incredibly rewarding and exhausting. Over the years, I’ve experienced highs of motivation and productivity, but I’ve also hit those low points, battling burnout and loneliness. In this post, I want to share some of the habits, strategies, and mindset shifts that have helped me stay in the game and maintain the discipline and accountability necessary to keep moving forward. If you’re a founder—or on any long-term entrepreneurial journey—I hope these insights can help you do the same. Watch on YouTube The Isolation of Being a Founder Being a single founder can be a lonely journey. For me, working from home, with my wife and kids out for the day, often leaves me in the company of my dog and cats. While solitude has its perks, isolation can be damaging to both motivation and productivity. Find Community: Join a mastermind group or work from a co-working space. Being around people, even casually, can be a game-changer. I started playing tennis twice a week—not because I’m a tennis fanatic, but because it gives me a social outlet and some physical exercise. Finding balance between work, family, and social time is key to staying mentally sharp. Surround Yourself with Peers: Programs like TinySeed or the DC Accelerator not only offer education but surround you with like-minded individuals who push you to level up. In my career, the periods when I’ve had a strong community around me have been my most productive. Accountability: The Secret Weapon for Consistent Progress One of the biggest myths in entrepreneurship is the idea of the “solopreneur” doing everything on their own. The reality? Success comes from being accountable, whether it’s to your team or an external source. Accountability to Your Team: I’ve got payroll to meet, and employees who count on me. That creates built-in accountability. But even if you’re a one-person operation, you need some form of this. Whether it’s a peer accountability partner or joining a program with structured...

RS327: 3 Traits Of Successful Founders w/ Rob Walling

Sep 11, 2024 44 min

Craig has TinySeed’s Rob Walling in the hot seat today. They’re chatting about defining, attaining, and maintaining success. What does success mean to you? How do focus, clarity, and execution fit into it? Rob, a leading founder and one of the most successful entrepreneurs in the SaaS industry, shares his expert advice and insights on achieving success. Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast 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. We’ll see you next week! Highlights from Craig and Rob’s conversation: What makes Rob Walling a successful founder How to gain clarity and focus in your decision-making Relentless execution: why the winners are those who practice every day Intrinsic vs. extrinsic motivation Creating a network of accountability The parallels between “fitness” and being a founder Making success fun Finding someone to hold you accountable Is there a one-stop shop for founders? The layers of Rob’s business model funnel A Little About Rob: Rob Walling is the founder of TinySeed, host of Startups For The Rest Of Us, and of MicroConf. Rob has bootstrapped multiple startups to exit, most recently Drip. He has been advising, mentoring, and investing in startups for more than a decade. He has also written The SaaS Playbook which aims to help entrepreneurs strategize and build frameworks from the trenches so they can grow successful SaaS companies. Links & Mentions from This Episode: saaslaunchpad.co Rogue Startups Resources: Follow Craig on Twitter/X Craig on LinkedIn Castos Founder Insights

RS326: 5 Things Most Founders Struggle With

Sep 4, 2024 19 min

Today’s a solo episode with Craig where he’s talking through the 5 common topics and themes that he helps most of his coaching clients through. Whether it’s through his 1:1 coaching with private clients or in serving as Advisor In Residence at TinySeed, where he’s advised over 50 SaaS founders, a few common patterns have emerged. These topics include: Managing Uncertainty Getting a Sanity Check On New Initiatives Being An Accountability Partner Navigating Financial Troubles Sales & Marketing Strategy Most important thing to remember from this is that being a founder is tough, but you are not alone. Text a friend, join a community, get a coach, but somehow build that support network around yourself so that you can thrive as a founder to grow your business. If you’re interested in learning more about my one-on-one founder coaching head over to craighewitt.me/coaching – I offer free 30 minute consultation sessions, and if we’re a good fit to work together we can go from there.

RS325: Stuck? Ask Yourself These 3 Questions

Aug 30, 2024 10 min

Are you a SaaS founder feeling stuck, unmotivated, or unsure about your next move? In this video, I dive into three powerful questions that can help you break through mental barriers and gain clarity on your business’s direction. These thought-provoking questions will challenge you to confront hard truths, think like an outsider, and tap into your own wisdom. Whether you’re just starting out or scaling up, these insights will help you refocus and reinvigorate your entrepreneurial journey. Don’t miss this opportunity to gain a fresh perspective on your SaaS business!

RS324: $100 Million Bootstrapped SaaS with Adam Robinson

Aug 21, 2024 41 min

In this episode of the Rogue Startups podcast, Craig sits down with Adam Robinson to explore key topics such as founder psychology, overcoming self-limiting beliefs, and avoiding self-sabotage. They delve into how to identify and break free from the plateau and gradual decline that can occur when you believe you have achieved product-market fit but haven’t. Adam, who has built multiple successful businesses, shares his valuable insights and practical tips with Craig. Don’t miss out—tune in to gain actionable advice from an experienced entrepreneur! Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast 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. We’ll see you next week! Highlights from Craig and Adam’s conversation: The success story behind Adam’s unicorn B2B SaaS business An in-depth exploration of achieving product-market fit The importance of establishing effective business processes How to avoid the entrepreneurial trap: recognizing when to transition to a new venture The story behind “2,300 sign-ups and 13 paying customers, 6 weeks after launch” How Adam deals with bad press when he pushes the envelope The future of data privacy and cookies Creating value for customers and learning from mentors and successful entrepreneurs A Little About Adam: Adam is the CEO of Retention.com. Retention.com is the industry-leading Shopify e-commerce solution for increasing revenue. They enable email-based retargeting so brands can re-engage lapped audiences and grow their email lists for the future. On the outside, Retention.com is a magic wand that makes money fall from the sky. He also runs RB2B, a website that helps identify your anonymous website visitors. Links & Mentions from This Episode: Adam Robinson, LinkedIn Retention.com RB2B.com Rogue Startups Resources: F...

RS323: Breaking Through Plateaus with Josh Ho

Aug 14, 2024 51 min

Today on the Rogue Startups Podcast, Craig chats with Josh Ho from Referral Rock about the peaks and valleys of being a founder. When is the right time to sell? Is there ever a right time? How do you break through a plateau in your business growth? How do you switch from wearing your visionary hat to your marketing and sales hat? They also do a deep dive into when and how you should go about delegating tasks so you can focus on more important things. Josh built Referral Rock from the ground up. Referral Rock helps customers run end-to-end referral programs with frictionless sharing, nudge reminders, and rewards customers actually care about. They help bring in more referrals from happy customers — through a remarkable referral experience — without the pain of building & tracking it all yourself. Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast 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. We’ll see you next week! Highlights from Craig and Josh’s conversation: Switching from visionary mode to marketing mode Reflecting on decisions made as a founder Letting go of your inner Superman: letting your team handle sales Knowing what you need and being strong enough to look for help Strong operations is speed The importance and effectiveness of SEO today Valuating your business and progress Growing, selling, and the future of your business “Good enough” versus “Being done” Links & Mentions from This Episode: Referral Rock Josh Ho on Twitter/X Josh Ho on LinkedIn Rogue Startups Resources: Follow Craig on Twitter/X Craig on LinkedIn Castos Founder Insights

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Podcast details

Created by: Craig Hewitt
Status: Active
Latest episode: Nov 11, 2026
Episodes: 50
Release period: Weekly
Avg. episode length: 41 min
Explicit: No
Language: English

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