Rogue Startups

RS368: Grok Bot & Hermes

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 overha

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RS367: How to Hire in the AI Era

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 process

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

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 thi

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RS365: Marketing that Actually Works Today

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

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RS364: Think Less, Do More

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 i

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RS363: Why Talking to AI About Your Business Is Dangerous

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

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RS362: Hidden Multipliers with Jason Cohen

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 trans

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RS361: Lessons Learned Selling A Business

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 l

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RS360: Kill the Hippo

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 be

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Huge Work (and life) Updates

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/

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RS358: Your Design Sucks

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 id

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RS357: I Got Hacked

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 bui

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

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

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RS355: Code Velocity and the Future of SaaS

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.

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RS354: The State Of Podcasting Heading Into 2026

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 Cra

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RS353: Is This the Last Organic Marketing Channel

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

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RS352: AI Killed Traditional Marketing – Here's What's 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 methods, it feels like the Wild Wild West. But within all that chaos are opportunities that we shouldn

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RS351: Why Brands Fail on Reddit

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

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

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 insight

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RS349: Ranking In ChatGPT with Devesh Khanal

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 opti

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