Rogue Startups
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.
Episodes
Your Product Is Now a Wrapper Around Go-To-Market | Hiten Shah
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 was
From Audience To Income
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.
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
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 sti
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 s
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 cri
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 wr
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
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 Multipl
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, t
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 yo
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/
Cha
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 t
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
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
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, e
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
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 cha
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,
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
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
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-driv
RS348: Not Exactly White Hat AI-SEO with Lars Lofgren
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
RS347: How to Rank Any Brand In AI Results
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
RS346: What 11 Years in SaaS Really Looks Like
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 entrepre
RS345: The State Of Search 2025
- 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) - Mar
RS344: 12 Years to Overnight Success with Amar Ghose
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 share
A Caffeine Infused Diatribe
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
RS342: SaaS Survival Mode - AI, Niches & Navigating Chaos
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 entrep
RS341: Microconf 2025 Recap
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
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-u
RS339: AI Skeptic, or Believer
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 t
RS338: Balancing Your Use of AI with Aaron Francis
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'
RS337: Building AI Native SaaS w/ Jordan Gal
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 o
RS336: Claude Project Deep Dive with Alison French
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
RS335: Evaluating AI Model Performance with Stuart Grey
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 harn
RS334: How AI Saves Me 10 Hours A Week
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 n
RS333: Grading My Business (and yours!)
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 c
RS332: Competing with Stripe and Hubspot (ft. Geoff Roberts)
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 un
RS331: I'm Still Here...
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 po
RS330: Product-Led Playbook with Wes Bush
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 prod
How To Hire For Growth
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 g
RS328: Are you Productive or Effective as a founder?
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 a
RS327: 3 Traits Of Successful Founders w/ Rob Walling
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
RS326: 5 Things Most Founders Struggle With
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 topi
RS325: Stuck? Ask Yourself These 3 Questions
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
RS324: $100 Million Bootstrapped SaaS with Adam Robinson
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 hav
RS323: Breaking Through Plateaus with Josh Ho
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 di
RS322: Marketing, in 2 hours a week
In this episode Craig descirbes his current SaaS marketing approach. Balancing Active and Passive marketing, he’s got his marketing time down to just a few hours a week. Using a video-first, AI-assisted workflow he’s reaching his target market, educating his prospective customers, and building goodwill in the community.
RS321: B2B Lead Gen on LinkedIn
If there’s one thing Craig loves more than podcasting, it’s sales.
In this episode, he shares his enthusiasm with tech sales coach Peter Ahn. They discuss everything from bridging the gap between creating content and driving leads to the importance of being genuine and authentic.
Peter drops plenty of knowledge bombs, so grab a chair, take out
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