Podcast · Business

Rogue Startups

by Craig Hewitt · English · Business

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 t

New episodes: Weekly
Typical length: 49 min
Latest: 13 Oct 2026
Language: English

Latest episode

13 Oct 2026 · 51 minNew

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 wasn’t there” a year ago. That leads into local models: how much hardware you really need, why open-weight models still have a “flavor” from how they’re trained, and why even the frontier labs don’t fully know what a model will be good at until…

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Earlier episodes 29 most recent

29 Sep 2026 · 57 min
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. Craig talks about growing his YouTube channel toward 25,000 subscribers and building a second revenue stream through ads and brand partnerships. We dig into the gap between getting views and building a business: growing an email list, creating…
22 Sep 2026 · 50 min
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 overhaul a 15-year-old WordPress site, and they explore what the next generation of AI-powered websites and…
15 Sep 2026 · 49 min
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 processes have changed and evolved, from async video interviews to paid work samples and screen-recorded…
8 Sep 2026 · 41 min
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 thinking, keep you accountable, and be completely honest about the business - along with the risks…
1 Sep 2026 · 49 min
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 Colin debate whether blogging still matters, why YouTube may be the strongest starting point for…
25 Aug 2026 · 48 min
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 increasingly blurry line between building a product and simply building something for yourself. The…
18 Aug 2026 · 33 min
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 company" still holds up for B2B, legal, and SaaS businesses that swear they're different. It's a…
11 Aug 2026 · 51 min
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 transformation customers actually want instead of simply adding AI to their products, why repositioning…
4 Aug 2026 · 46 min
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 life-changing exit. They also explore how AI is reshaping SaaS, content marketing, and YouTube, as…
E360 · 29 Jul 2026 · 44 min
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 beats relying on surveys and feature voting alone, and discusses how companies can avoid building…
21 Jul 2026 · 15 min
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/
18 Mar 2026 · 54 min
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 ideation pages, this episode is a must-listen for anyone vibe-coding their next SaaS app and…
11 Mar 2026 · 44 min
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 building AI-driven products. If you’re launching SaaS with tools like Next.js, Supabase, and Claude,…
4 Mar 2026 · 1 hr 2 min
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 hacker, or SaaS entrepreneur trying to figure out how to stay relevant and move fast, this one's…
25 Feb 2026 · 58 min
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. Highlights from Craig and Arvid’s conversation: AI is shifting the founder’s role from building to…
26 Nov 2025 · 41 min
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 Craig and Colin’s conversation: How podcasting has changed over the last 10 years The more we’re…
1 Oct 2025 · 51 min
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 AI boom is a lasting shift or just another bubble. Highlights from Craig and Brian’s conversation:…
24 Sep 2025 · 50 min
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’t miss out on.. Ross and Craig explore how founders and marketers can leverage AI to create…
17 Sep 2025 · 45 min
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’re curious about launching your first campaign or wondering if Reddit should be part of your…
10 Sep 2025 · 57 min
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 insights you won’t want to miss. Highlights from Craig and Brendan Hufford’s conversation: AI in SEO: how…
3 Sep 2025 · 1 hr 4 min
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 optimization agency that helps e-commerce brands increase online sales through user research,…
16 Jul 2025 · 53 min
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 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…
9 Jul 2025 · 48 min
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 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…
2 Jul 2025 · 49 min
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 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…
11 Jun 2025 · 18 min
RS345: The State Of Search 2025
- LLMs.txt article: https://www.quoleady.com/llm-txt-files/ - Craig's YouTube channel: https://youtube.com/@thecraighewitt
4 Jun 2025 · 47 min
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 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…
28 May 2025 · 47 min
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 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.
23 Apr 2025 · 45 min
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 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…
26 Mar 2025 · 18 min
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.

About Rogue Startups

Rogue Startups is a English business podcast from Craig Hewitt. Melo plays each episode straight from the publisher's own feed — no ads added, no account needed — and remembers where you stopped, in this browser only.

Publisher: Craig Hewitt
Language: English
Category: Business
New episodes: Weekly
Typical length: 49 min
Latest episode: 13 Oct 2026
Feed: RSS — paste into any podcast app
Apple Podcasts: podcasts.apple.com/podcast/id954938779

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