Rogue Startups

- 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...

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 criteria for evaluating SaaS businesses: 1. Pr...

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 unique setup where everyone makes $210k/year (...

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 podcast. Hit me up on Twitter , LinkedIn or eve...

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 product-led mindset and methodology that Wes empl...

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 game. Watch on YouTube 1. When Should You Kno...

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 accountability necessary to keep moving forwar...

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. Do you have any comments, questions, or topi...

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 topics include: Managing Uncertainty Getting a Sanity Check On...

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 your own wisdom. Whether you’re just starting out or sc...

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 haven’t. Adam, who has built multiple successful...

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 dive into when and how you should go about deleg...

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.

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 a notebook, and jot down some great tips from this epi...