Rogue Startups

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, and others are not. Craig candidly shares insights from personal and professional growth and extensive research. Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at [email protected]. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week! Highlights from this episode: Optimal pricing strategies for maximum profitability Enhance retention by ensuring that your product or service is exceptionally sticky Incorporate payment solutions seamlessly into your business to enhance user experience Become a valuable asset for your clients by contributing to their revenue streams Implement strategies to heighten switching costs, fostering customer loyalty. Customers should be getting value even when they’re not actively using your product Stand out from competitors by highlighting unique features and advantages Confirm market demand by researching your niche Links & Mentions from This Episode: Designing The Ideal Bootstrapped Business – Microconf talk Rogue Startups Resources: Follow Craig on Twitter/X Castos Founder Insights

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 of pricing strategies and delivering enhanced value propositions to justify premium prices. Learn how diversifying variables beyond product features can make your business highly desirable to your market. Moreover, Jason emphasizes the pivotal role of the community in authentic company development. Uncover the importance of leveraging existing assets and explore his innovative “adjacency matrix” method for strategic expansion. Got any thoughts on our content or ideas for upcoming episodes? Reach out to Craig via email at [email protected]. If you’ve found our podcast valuable, don’t hesitate to share it with others. If you could spare a moment, leave us a review on iTunes. We appreciate your support and look forward to connecting again next week! Highlights from Craig and Jason’s conversation: Determining success or failure as a founder and business owner Strategies for becoming the market leader in your industry Importance of building a community to enhance customer value Distinguishing between brand, company culture, values, and mission Identifying when branding becomes crucial for a startup’s success Deciding between staying focused on your core business or expanding into new ventures Embracing a culture of innovation despite the risk of failure Achieving a balance between personal fulfillment, skill development, and company needs Practical applications of AI for internal operations and enhancing customer experience A Little About Jason: With over 27 years of experience in business and software development, Jason Cohen is the founder of WP Engine where he has served in several roles including CEO, Head of Engineering, Head of Product, and CTO. Jason Cohen is the Chief Innovation Officer at WP Engine, with a focus on the intersection of corporate and technology strategies as well as continue as the company’s executive sponsor for the headless platform, Atlas. Jason is a serial entrepreneur, having built four technology startups to more than $1 million in annual revenue. He is a founding member and mentor at Capital Factory, and was previously a founder of Smart Bear and IT WatchDogs. Jason received the EY Entrepreneur Of The Year 2017 Central Texas Award for Technology. Links & Mentions from This Episode: WP Engine Jason on Twitter/X Jason’s Blog Rogue Startups Resources: Follow Craig on Twitter/X Castos Founder Insights

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 passive marketing? How do you know how much time to put into marketing? What are good marketing strategies for new business owners? Check out this episode for the answers to these questions and more. Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at [email protected]. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week! Highlights from Craig and Adam’s conversation: Utilizing your Reddit page as a landing page for your business Optimizing LinkedIn as a platform to maximize its potential Identifying which companies are suited for each social media platform The Marketing for Founders service and model Recognizing the flexibility inherent in marketing strategies; it’s not one size fits all Consistency is the key to seeing results from marketing When to engage in active marketing versus passive marketing How much time should you spend on marketing? When you should do your marketing on your own versus when to hire a marketer Find where your customers are hanging out Identifying the two biggest obstacles that might be impeding your scalability efforts A Little About Adam: Adam’s goal and vision for Marketing for Founders is to help B2B SaaS founders do their own marketing. Links & Mentions from This Episode: Marketing for Founders Adam Shaw’s LinkedIn The Marketing Memo LinkedIn Sales Navigator Gummy Search Hive Index Sparktoro Rogue Startups Resources: Follow Craig on Twitter/X Castos Founder Insights

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 on the rapid evolution of AI and his tips on building thriving ventures. Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at [email protected]. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week! Highlights from Craig and Dan’s conversation: Dan’s podcasting inspirations and his journey into the industry Why Dan chose podcasting over any other platform Is YouTube worth the effort? Finding the overlap between creativity and growth The importance of Investing in your team and treating your business like an investment Getting over imposter syndrome and what your job is as an entrepreneur Creating successful businesses versus businesses that are “just okay” The difficulty of getting to $1 mil for a SaaS company The lifecycle of the entrepreneur ecosystem Predictions for bootstrapping and podcasting trends in the next 5 years A Little About Dan and TropicalMBA: Tropical MBA started in 2009 when hosts Dan and Ian wanted to meet other entrepreneurs for some celebration and commiseration. Most of their first episodes were just them, sharing what they learned about bootstrapping their own business until they concluded that journey with a multi-seven-figure exit. Both Dan and Ian have moved on to their next projects but continue to talk with entrepreneurs on their show. Links & Mentions from This Episode: Tropical MBA Connect with Dan on Twitter/X Lifestyle Business Podcast Internet Business Mastery Smart Passive Income Podcast Startups for the Rest of Us “Profit First: Transform Your Business from a Cash-Eating Monster to a Money-Making Machine” by Mike Michalowicz Check out Matt Paulson’s Twitter/X “Exploitative Play in Live Poker: How to Manipulate your Opponents into Making Mistakes” by Alexander Fitzgerald Rogue Startups Resources: Follow Craig on Twitter/X Castos Founder Insights

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 grow, stay sane, and thrive in their business. If you’re a SaaS founder and are looking for a sounding board, someone who’s seen a lot in business, and has your back (through thick and thin) head over to craighewitt.me/coaching to learn more and schedule a free 30-minute session. The coaching has been really rewarding, and is a great way to give back to the founder community that has given him so much. If you’re interested in sponsoring Rogue Startups, hit me up on Twitter/X at twitter.com/thecraighewitt

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 boutique sales and marketing consultancy all around B2B SaaS startups. She is the Marketing Gal who got bit by the revenue bug and became passionate about helping companies scale their revenue by focusing on the intersection of sales and marketing. With over 20 years of experience in the field, she specializes in assisting B2B founders and leaders who venture into new markets. Her ultimate goal is to help you build a robust sales and marketing infrastructure that not only streamlines lead generation but also maximizes your ability to close deals. And the best part? She does all this while keeping your expenses to a minimum. Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at [email protected]. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week! Highlights: Why everyone sucks at execution. Ideas are cheap. Execution is the hard thing. Recognize how to get out of your own way and when to delegate How can you delegate cheaply Free up your time so you can do the higher-leverage tasks Getting good content writers and/or a copy editor The entire team needs to know the values and priorities of the company People discount the importance of brand research and focus ICP: marketing, content, When you’re taking a dollar of profit and reinvesting in growth, where do you focus? Build a prospect list and then proactively nurture that small segment Versium: matched audience media The importance of retargeting Your Dream 100 Cold E-mail: a balance of who you can go after, the right time, and the right place Starting your bootstrapped B2B business today: where do you focus? Look at your prospects, laser focus on your ICP Apollo.io for data hacking Recognizing you can’t do it all Look at your tech-stack Know, instantly, who you can delegate to Throw tasks out into the world and see what happens As a founder, you’re never going to find someone who can sell as much as you Resources: Alison French, LinkedIn LTO.com Follow Craig on Twitter/X Castos Founder Insights