Rogue Startups

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...

Clearly Design works in every aspect from branding to marketing, from product to promotion. Go to Clearly. Design for a discount on his monthly design subscription service. Tell him that Rogue Startups sent you. What gets someone to buy our products or services? How do you make LinkedIn a meaningful sales channel? In today’s discussion, Craig speaks with LinkedIn expert Ryan Musselman on optimizin...

Clearly Design works in every aspect from branding to marketing, from product to promotion. Go to Clearly. Design for a discount on his monthly design subscription service. Tell him that Rogue Startups sent you. Danny DelVecchio joins Craig today to discuss creating, posting, and uploading video content on LinkedIn. In today’s conversation, you’ll discover how to overcome challenges in creating co...

Clearly Design works in every aspect from branding to marketing, from product to promotion. Go to Clearly. Design for a discount on his monthly design subscription service. Today Craig is chatting with Nemanja Zivkovic about conversion on LinkedIn. This is the crux of LinkedIn for a lot of us, as B2B SaaS founders, especially indie or bootstrapped businesses. So how do you find opportunities on Li...

This episode is sponsored by Clearly Design . Francois and his team at Clearly Design are absolute geniuses of UI, UX, and design. If you’re looking to level up your design, UI, and UX give Clearly Design a try If you’re running a B2B business today, chances are that LinkedIn is a fantastic growth opportunity for you, and your business. But if you’re looking at the vastness of how to grow your aud...

Optimize your company’s retention, and supercharge growth with Churnkey . In today’s episode, Craig welcomes Sam Browne. They take a deep dive into the ever-evolving landscape of LinkedIn, the premier platform for professionals seeking to expand their network and amplify their influence. With Sam’s expert advice and practical tips, they guide listeners through proven strategies for personal brandi...

Optimize your company’s retention, and supercharge growth with Churnkey . In this episode Craig sits down with Matt Hayman from Linklo to talk through how we as SaaS founders can set up cost effective LinkedIn ads. Matt has strong experience in building B2B lead flows for a variety of companies, and out of that experience saw the pain for a more customizable LinkedIn ads experience. In the episode...

Optimize your company’s retention, and supercharge growth with Churnkey . Are you looking to build the perfect SaaS business? Discover the key elements for crafting a thriving SaaS venture in the latest Rogue Startups episode. Craig delves into the success story of Castos, dissecting eight crucial attributes essential for any SaaS business to flourish. Some of these are things Castos has nailed, a...

This episode is sponsored by ChurnKey: Optimize your company’s retention and supercharge growth with Churnkey . Are you looking to fuel your startup’s revenue growth? Jason Cohen , founder of WP Engine , joins Craig behind the mic on this episode of Rogue Startups. Join Jason and Craig as they delve into strategies for sustained revenue growth, even when certain metrics plateau. Discover the power...

In today’s episode, Craig is joined by Adam Shaw from Marketing for Founders to talk about precise and overarching marketing strategies. Adam’s expertise lies in navigating Reddit and LinkedIn, two social media platforms that B2B SaaS entrepreneurs often neglect. Together, they explore Adam’s techniques for Reddit, LinkedIn, and broader marketing principles. Should you focus on active marketing or...

Join Craig as he chats with Dan Andrews , renowned cohost of the Tropical MBA , a weekly podcast dedicated to bootstrapping businesses and entrepreneurship. Dan is also the founder and brains behind Dynamite Circle and Remote First Recruiting . Today, they’re dishing out some expert advice about podcasting, content creation, and strategies for acquiring customers. Tune in to explore Dan’s opinions...

In this solo episode Craig talks through a few updates from Castos, how he’s thinking about growth, and where he’s focusing his attention and energy in the business. Craig also gives an update on his personal content: this podcast, his Founder Insights newsletter (check it out at craighewitt.me/join ) and his new 1-on-1 coaching business. Craig’s started coaching founders, 1-on-1, to help them gro...

Alison French joins Craig behind the mic today to talk about ICP and go-to-market strategy, as well as the challenges that bootstrap founders have. We can all overcome these struggles with the right tools, systems, outlook, and determination. She commiserates with Craig about what bootstrappers have to go through and also gives some great advice for new startups and entrepreneurs.  Alison runs a b...