Rogue Startups

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 forward. If you’re a founder—or on any long-term entrepreneurial journey—I hope these insights can help you do the same. Watch on YouTube The Isolation of Being a Founder Being a single founder can be a lonely journey. For me, working from home, with my wife and kids out for the day, often leaves me in the company of my dog and cats. While solitude has its perks, isolation can be damaging to both motivation and productivity. Find Community: Join a mastermind group or work from a co-working space. Being around people, even casually, can be a game-changer. I started playing tennis twice a week—not because I’m a tennis fanatic, but because it gives me a social outlet and some physical exercise. Finding balance between work, family, and social time is key to staying mentally sharp. Surround Yourself with Peers: Programs like TinySeed or the DC Accelerator not only offer education but surround you with like-minded individuals who push you to level up. In my career, the periods when I’ve had a strong community around me have been my most productive. Accountability: The Secret Weapon for Consistent Progress One of the biggest myths in entrepreneurship is the idea of the “solopreneur” doing everything on their own. The reality? Success comes from being accountable, whether it’s to your team or an external source. Accountability to Your Team: I’ve got payroll to meet, and employees who count on me. That creates built-in accountability. But even if you’re a one-person operation, you need some form of this. Whether it’s a peer accountability partner or joining a program with structured check-ins, having someone who will ask, “Did you get that done?” is crucial. Accountability Buddy: Inspired by a conversation with Rob Walling, I decided to create My Founder Pal, an accountability network for founders to check in with each other regularly. It’s still in its early stages, but the idea is to create a system where we set goals and follow up on progress, offering each other the motivation to keep pushing forward. Daily Structure for Focus and Efficiency One simple habit that has had a huge impact on my productivity is making a list of three things I need to get done each day. I literally put the notebook on my keyboard so it’s the first thing I see before starting my day. These can be small tasks, but they are important things that move the needle. I prefer to write the list in the morning so I have a fresh perspective on what matters most that day. This simple act keeps me focused on what’s essential, rather than getting distracted by Slack or email first thing in the morning. It’s about prioritizing effectiveness over productivity—doing what matters most rather than just doing more things. Sharing Your Work Another aspect of accountability that I’ve found useful is sharing my work with my team. Whether it’s a new YouTube video or an internal operations playbook, I post it in Slack for feedback and accountability. It not only helps me feel more productive, but it also fosters a sense of friendly competition among my team. Avoiding Negativity and Overanalysis We all have tough days, but one of the worst habits I’ve fallen into is bitching and complaining when things aren’t going well. It’s easy to get stuck in a negative loop—SEO is dead, cold outreach doesn’t work, our customers are too price-sensitive, and so on. But in reality, no business is perfect. Focusing on the negatives too much paralyzes progress. Instead, I’ve learned to compartmentalize the challenges and move forward. Acknowledge the imperfections in your business, but don’t let them dominate your thoughts. Staying active, shipping, and doing the work will always outweigh overanalyzing the flaws in your business. Focus on Inputs, Not Outcomes As founders, we often get discouraged by focusing too much on outcomes. It’s tempting to start a marketing channel and expect instant results. But the reality is, you need to put in sustained effort over time to see results. I’ve learned that it’s more productive to focus on inputs—the work we’re putting in—rather than getting fixated on the immediate results. For example, if you’re investing in a new marketing strategy like LinkedIn outreach, give it time. Stick with it for a quarter before evaluating its success. Switching strategies too quickly leads to rash decisions and missed opportunities. Separating Strategy from Execution Lastly, one mistake I’ve made is trying to do all parts of a project at once—strategy, planning, and execution. I’ve found that separating planning from doing yields better results. For instance, with a YouTube video, I focus on planning and scripting first, and then tackle the actual recording when I’m fresh the next day. Trying to do everything at once burns me out and results in lower quality work. Conclusion Being a founder is a long game, and the key to longevity is building the right habits and support systems. Whether it’s finding community, staying accountable, or structuring your workday for focus, these small changes can lead to big improvements. And remember, it’s about progress, not perfection. I’d love to hear your thoughts—what habits help you stay productive and accountable as a founder? Drop a comment or message me to share! Plus i share an update on https://myfounderpal.com – an accountability community for SaaS founders.  

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 topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. 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 Rob’s conversation: What makes Rob Walling a successful founder How to gain clarity and focus in your decision-making Relentless execution: why the winners are those who practice every day Intrinsic vs. extrinsic motivation Creating a network of accountability The parallels between “fitness” and being a founder Making success fun Finding someone to hold you accountable Is there a one-stop shop for founders? The layers of Rob’s business model funnel A Little About Rob: Rob Walling is the founder of TinySeed, host of Startups For The Rest Of Us, and of MicroConf. Rob has bootstrapped multiple startups to exit, most recently Drip. He has been advising, mentoring, and investing in startups for more than a decade. He has also written The SaaS Playbook which aims to help entrepreneurs strategize and build frameworks from the trenches so they can grow successful SaaS companies. Links & Mentions from This Episode: saaslaunchpad.co Rogue Startups Resources:  Follow Craig on Twitter/X Craig on LinkedIn Castos Founder Insights

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 New Initiatives Being An Accountability Partner Navigating Financial Troubles Sales & Marketing Strategy Most important thing to remember from this is that being a founder is tough, but you are not alone. Text a friend, join a community, get a coach, but somehow build that support network around yourself so that you can thrive as a founder to grow your business. If you’re interested in learning more about my one-on-one founder coaching head over to craighewitt.me/coaching – I offer free 30 minute consultation sessions, and if we’re a good fit to work together we can go from there.

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 scaling up, these insights will help you refocus and reinvigorate your entrepreneurial journey. Don’t miss this opportunity to gain a fresh perspective on your SaaS business!

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 businesses, shares his valuable insights and practical tips with Craig. Don’t miss out—tune in to gain actionable advice from an experienced entrepreneur! Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. 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: The success story behind Adam’s unicorn B2B SaaS business An in-depth exploration of achieving product-market fit The importance of establishing effective business processes How to avoid the entrepreneurial trap: recognizing when to transition to a new venture The story behind “2,300 sign-ups and 13 paying customers, 6 weeks after launch” How Adam deals with bad press when he pushes the envelope The future of data privacy and cookies Creating value for customers and learning from mentors and successful entrepreneurs A Little About Adam: Adam is the CEO of Retention.com. Retention.com is the industry-leading Shopify e-commerce solution for increasing revenue. They enable email-based retargeting so brands can re-engage lapped audiences and grow their email lists for the future. On the outside, Retention.com is a magic wand that makes money fall from the sky. He also runs RB2B, a website that helps identify your anonymous website visitors. Links & Mentions from This Episode: Adam Robinson, LinkedIn Retention.com RB2B.com Rogue Startups Resources: Follow Craig on Twitter/X Craig on LinkedIn Castos Founder Insights

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 delegating tasks so you can focus on more important things. Josh built Referral Rock from the ground up. Referral Rock helps customers run end-to-end referral programs with frictionless sharing, nudge reminders, and rewards customers actually care about. They help bring in more referrals from happy customers — through a remarkable referral experience — without the pain of building & tracking it all yourself. Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. 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 Josh’s conversation: Switching from visionary mode to marketing mode Reflecting on decisions made as a founder Letting go of your inner Superman: letting your team handle sales Knowing what you need and being strong enough to look for help Strong operations is speed The importance and effectiveness of SEO today Valuating your business and progress Growing, selling, and the future of your business “Good enough” versus “Being done” Links & Mentions from This Episode: Referral Rock Josh Ho on Twitter/X Josh Ho on LinkedIn Rogue Startups Resources: Follow Craig on Twitter/X Craig on LinkedIn Castos Founder Insights

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 episode of the Rogue Startups podcast. Highlights from Craig and Peter’s conversation: Why are technical founders so scared of tech sales The trigger that helps tech founders understand sales Earning the trust of your customers and helping them gain confidence Staying up-to-date with authentic sales strategies Dealing with imposter’s syndrome Which businesses benefit most from LinkedIn for lead generation Make your world ubiquitous for potential customers Creating content creation that will generate leads A Little About Peter: Peter is a Korean-American tech sales coach and former VP with experience at Twingate, Front, Slack, Dropbox, and Google, he is passionate about sharing his authentic experience as an Asian-American while helping others find their own unique sales voice. Peter knows that sales is becoming increasingly difficult, so developing an “edge” or advantage requires combining effective skills and confidence in one’s identity. He coaches on both of those topics. Links & Mentions from This Episode: Peter on LinkedIn Peter Ahn website Rogue Startups Resources:  Follow Craig on Twitter/X Craig on LinkedIn Castos Founder Insights

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 optimizing your LinkedIn presence. Ryan highlights the importance of focusing on and mastering a single platform for maximum impact. Understanding effective methods to connect with a broad audience is crucial for achieving your strategic goals. LinkedIn offers excellent opportunities to engage with your target demographic. Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. 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 Ryan’s conversation: What influences customers to buy services and products What if customers don’t know what they want? The answer to what they need is inside of them, so ask good questions Selling the path to the outcome and the transformation Focus on helping potential and current customers overcome their obstacles Have a natural way to sell without “selling” Speak to the problem or the want instead of using the phrase “demo” Maximizing the time you spend on LinkedIn The more rapport you build with a potential customer, the more they will trust you Engaging with their content in order to create deeper connection rates LinkedIn as a platform is embracing video more and more LinkedIn as an amplification system The power of video for building connections Be intentional with  LinkedIn for 6 months: engage with content, make connections, and build relationships. A Little About Ryan: Ryan Musselman is the founder of Coaches who Close. CwC equip coaches to close, scale, and enterprise with new clients, content engines, and constant lead flow. Links & Mentions from This Episode: Ryan on LinkedIn Rogue Startups Resources: Follow Craig on Twitter/X Craig on LinkedIn Castos Founder Insights

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 compelling video content, even if you lack confidence on camera. Uncover the essentials of selecting the right gear to kickstart your video journey and crafting timeless content across various platforms. Gain insights into balancing visual appeal with clear messaging and discover influential LinkedIn users worth following. Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. 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 Danny’s conversation: Tips for creating videos when your on-camera presence is lacking Why people don’t create video content on LinkedIn Essential gear and tools for getting started with video Creating evergreen content across multiple platforms Choosing assistants and social media managers What happens when  you overemphasize graphics over your message Top LinkedIn users to learn from Batching recording sessions each week/month Maximizing engagement with LinkedIn connections Look for things that people are excited about and start conversations about it Three styles of video everyone should be creating: educational content, content that builds trust, and sales content A Little About Danny: Danny elevated founders with social video. He is also a father, husband, business owner, and coach. Links & Mentions from This Episode: Danny DelVecchio on LinkedIn Danny DelVecchio on YouTube Alex B Sheridan on LinkedIn Chris James on LinkedIn Laura Acosta on LinkedIn Rogue Startups Resources: Follow Craig on Twitter/X Castos Founder Insights