Rogue Startups

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...

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...

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...

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 ag...

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...

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,...

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-a...

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...

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, a...

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 busine...

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 f...

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...

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...