Rogue Startups

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...

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 secu...

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 exper...

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...

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 expl...

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...

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...

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 Re...

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 marketin...

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” sid...

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 re...

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 ahe...

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 StatusGato...

- 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 (00:1...

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 lon...

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...

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 fa...

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), Ec...

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...

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...

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 o...

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 I...

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 driv...

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 incorporati...