Rogue Startups

Craig is back! Today, he welcomes fellow podcaster Colin Gray back to the podcast. They dive into the ever-evolving world of podcasting, reflecting on how much the landscape has shifted over the last decade and what people are craving now more than ever: genuine human connection. From the tug-of-war between YouTube and podcast growth, to what it really means to build an AI-first product, they explore the trends shaping creators, customers, and the platforms that connect them. Highlights from Craig and Colin’s conversation: How podcasting has changed over the last 10 years  The more we’re pulled toward AI, the more we crave genuine connection Is it easier to grow a YouTube channel or a podcast? Content integration and becoming a centralized hub Spotify’s role in the evolution of podcasting Monetization: ads, donations, subscriptions, and more Balancing and prioritizing feature requests How AI is shaping customer expectations How to make your product AI-first Resources and Links from This Episode: The Podcast Host: https://www.thepodcasthost.com/  Colin on LinkedIn: linkedin.com/in/colinmcgray?originalSubdomain=uk  beehiiv: https://www.beehiiv.com/  Kit: https://kit.com/ Creator Hooks: https://creatorhooks.com/  Castos Free Tools: castos.com/tools Email me: podcast@roguestartups.com Find me on Twitter: @TheCraigHewitt If you feel like Rogue Startups has benefited you, and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes.  Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com  Chapters (00:00:00) - Rogue Startups: 100 Days of AI(00:00:48) - How Podcasting Is Affecting AI(00:05:14) - How To Integrate Podcasts into Your Business(00:09:18) - Is Podcasting The Most Popular Media Format?(00:14:18) - Steve Bartlett on Spotify and Video(00:18:11) - Podcaster on Separation of Podcasting and Editing(00:22:19) - Podcasts: How Do They Monetize?(00:23:20) - Has Alitud added advertising to our Episode Builder?(00:25:24) - How to Make a Living on Podcast(00:27:45) - How is AI Affecting Your Company's Business?(00:32:24) - How To Make a Chatbot Like a Human Being(00:34:08) - 100 Days of YouTube(00:37:43) - How to Grow a Podcast on YouTube(00:40:53) - PODCAST: A Chat With Craig

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 Weekly Newsletter for the(00:04:24) - Building With AI: How To Monetize It(00:08:00) - How Do You monetize AI?(00:08:49) - Bootstrapped SaaS: The Challenge(00:16:33) - How to Bootstrap a Startup at 40(00:23:48) - How to Write a 100-Day Video on YouTube(00:29:54) - How to Write a Scriptment for a Video(00:34:41) - How to Write a Short Video(00:36:23) - How to Edit Video in 2 Minutes(00:38:42) - Do You Think AI Will Cause a Recession?(00:41:49) - What are you most excited about AI in the future?(00:45:58) - Bill Simmons on Art and AI(00:49:55) - Craig Has All The Answers For AI

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?(00:10:52) - Will AI Change Your Life?(00:16:27) - SooooO(00:16:33) - Is LinkedIn the Place to Start Your Business?(00:24:13) - B2B Content: The Best Channels(00:28:49) - Instagram's Paid-For Content(00:29:42) - Traditional SEO vs AI SEO(00:33:21) - Content Marketing in SaaS: The Rise of AI(00:36:55) - The Internet's Most Overhyped(00:38:50) - What's The Business of Quora?(00:40:24) - How to start a blog on Reddit(00:40:55) - Biggest Disappointment in AI Tooling(00:43:50) - What I'd Be Most Disappointed In About Gmail(00:45:26) - I Think Google Will Win In The End

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(00:01:30) - Are You a Reddit Marketer?(00:05:45) - Multiple Reddit Accounts: How to start a community(00:12:53) - How to Get your Website and Brand Images indexed on Reddit(00:19:56) - Reddit Marketing: The B2B Content(00:22:46) - Is AI Eating Its Own Content?(00:29:07) - Top Tech Executives: Where Do You Think the World Will(00:30:39) - GPT5: When Will It Drop?(00:32:16) - Underrated AI Companies(00:37:00) - Will AI Agents Replace Jobs?(00:43:46) - How to get a job in the tech world

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 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) - The Best Guest for Marketing: Brendan from Growth Sprints(00:00:54) - How to Get Out of Stuck in the Past With SEO(00:05:33) - What Do You Do To Stay Fresh?(00:07:33) - Where Are You on the AI Spectrum?(00:12:32) - How to Leverage AI in Content(00:14:56) - Instagram vs. Twitter: Brand Safety(00:19:14) - PODCAST: Short Form and Long Form(00:19:51) - Facebook, LinkedIn: No More 'Zero Click'(00:20:59) - Content and Zero-Click Marketing(00:24:57) - Content Investment: The Trust Recession(00:30:19) - How to Build a Growth Strategy With SaaS Founders(00:33:10) - There's a better way to sell an SEO(00:36:51) - In the Elevator: Founder Gravity(00:37:55) - How to manage your LinkedIn and YouTube accounts(00:42:39) - How to Start a Business on a Single Channel(00:45:41) - Growthsprints: End of 2021(00:48:16) - Ideas for Digital Marketing...(00:52:46) - How to Build a Content Board with a Single Person(00:56:16) - How to Tell a Funny Story on a Podcast(00:57:00) - Brendan on Talking To Himself

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) - Pushing the Bottom of the Marketing Flourish(00:13:33) - Tim Ferriss: The Bottom of the Sales Cycle(00:16:21) - Category keywords and alternatives: What is SEM(00:18:49) - The 3 Types of Jobs in the SEO Market(00:21:23) - How to Get Your Bottom-of- Content to Rank in(00:30:05) - Don't Get On Reddit(00:35:36) - How to Get Your Lead Generation Solutions Recommended by LLMs(00:40:03) - Can You Rank in LLMs With ChatGPT?(00:45:30) - Do We Need AI in Our Jobs?(00:50:48) - Is AI Taking Over Your Business?(00:53:07) - Waverider vs. AI in Marketing Writing(00:59:06) - Grow and Convert: The AI Writing Tool

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 on Google?(00:22:46) - Local SEO: Don't Get Duped By Fake Reviews(00:27:00) - How to Build a Brand on Reddit(00:33:39) - How to manage content at the startup level(00:35:55) - What Do You Think of SEO?(00:40:28) - How to Optimize Content for AI in 2020(00:46:19) - How to Build a Content Team(00:50:13) - How Do You Get Your Personal Brand Out There?

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 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) - AI SEO in Inbound Marketing(00:01:10) - Noah Toa: The Only AI-based Tool for S(00:05:02) - How HubSpot is Preparing for AI-based Resignation(00:13:28) - How to Optimize Your Website With Google Search(00:17:18) - Is LLMs Txt important for your site?(00:23:09) - Ask ChatGPT: How Much of its Intelligence Is Based on(00:25:02) - What's AI Doing To Your Company?(00:32:43) - How Social Networks Are Affecting Business(00:35:28) - Deep Learning and the Google Cloud(00:37:08) - Top Tech Thinkers: The Future of Content(00:46:11) - Noah Toa: A Landing Page for New Users

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 Startup With Colin Bartlett(00:01:51) - Flare on the Internet Outage(00:03:48) - How Do You Capture Leads From Free Signups?(00:09:18) - How Long Can You Keep Working On Your Startup?(00:14:42) - How Do You Think Your SaaS Business Should Be Profitable(00:16:53) - What Your Team Looks Like on SaaS(00:19:12) - How We Run a WordPress Team(00:21:34) - How to Hire a Team in the AI Era(00:25:46) - Top Executives: How AI Will Affect the Business in 2(00:31:20) - Podcaster on An Economic Dip(00:32:17) - How Do We Stay Fresh After 11 Years?(00:37:22) - If You Had to Pick A Boss, What Would You Do?(00:38:39) - Cisco on SOC2 Compliance(00:42:30) - How much Time Should Your Team Work?(00:46:48) - How To Get Things Done As A CEO

- 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?

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 topic ideas for future episodes? Feel free to reach out to me: Chapters (00:00:00) - How to Build a 12-Year-Old SaaS Company(00:01:15) - Squarespace CEO on How Far Along the Business Is(00:03:39) - How We Went From Fast Follower to Industry Leader(00:08:35) - Jeff Bezos on Decisions Made by the Team(00:13:52) - Zenmaid's CEO on Never Enough(00:18:10) - How to Get More Out of a Manager(00:19:30) - Craig on His Side Businesses(00:25:49) - Kastos on What Would He Tell You?(00:28:03) - How Do You Continue to Evolve As a Founder?(00:33:16) - Brain tumor patient on work life balance(00:39:46) - Jordan G. on AI and the Economy(00:44:55) - Brands and the AI revolution(00:46:33) - Amar Ghosh on Connecting With People

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

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 (00:00:00) - Interview + Co-Host Chat(00:02:34) - Visit Annecy, France(00:02:51) - Living in France as an American(00:04:39) - Trump on Trade Wars and AI(00:05:04) - Bento CEO on Working With Customers(00:07:41) - What's the rest of the team like?(00:11:02) - How to Hire an AI-Inspired Team(00:16:46) - Bento's CEO on How Long Will He Run the Business?(00:18:55) - Bento CEO on Cash Exclusion(00:23:53) - WSJD: Business Cycle, Uncertain Future(00:27:15) - Have We Should Offer a Free tier?(00:33:03) - Bento vs. Mailchimp: How To Reach Out to(00:38:41) - Bento on Being a Utility Tool(00:40:24) - Bento on Collaboration and Its Impact(00:43:52) - Community and the AI of Business

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.

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:

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 you have to pay attention to what information you are getting from AI, but how it is affecting your productivity overall.  Resources and Links from This Episode: DNSimple Anthony Eden, LinkedIn Anthony Eden,

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

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, or if you’re creating the next AI tool, now is the time to embrace this technology. Resources and Links from This Episode: Rosie   Jordan on Twitter/X

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 professional lives can help save you time and free up some creative energy for being social, innovative, and expressing yourself. AI will give you the time to do the work to open yourself up to having personal experiences. Resources and Links from This Episode   Alison French on LinkedIn: https://www.linkedin.com/in/frenchalison/  LTO:

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: