Rogue Startups

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 (pro-rated) and can work 1-5 days a week- Took them 4 years to really nail the product (hey, good things take time!) Best Parts of the Convo:- Jeff got real about marketing struggles (who hasn't been there?)- Turns out ChatGPT is actually sending them customers now - wild!- We had a great debate about whether SaaS is still the golden ticket (spoiler: it's way more competitive now)- Talked about why sometimes it's better to stick with a "pretty good" business than chase the next unicorn Where They're Headed:- Aiming for $10M in revenue with a lean team of about 20 people- Shifting from being super product-focused to really pushing growth- Geoff's been at it for 8 years and plans to keep going for 7 more Real talk: This episode is perfect if you're building a SaaS company or thinking about bundling multiple tools together. Geoff drops some serious knowledge about what it's actually like in the trenches. Check them out at outseta.com if you want to see what they're building! #SaaS #Startups #Entrepreneurship

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 even Bluesky

Wes Bush, an entrepreneur and product-led coach, shares his insights on product-led growth (PLG) strategies. He explains how PLG differs from self-service SaaS and emphasizes it as a powerful marketing tool. Discussion includes overcoming skepticism, educating customers, and creating growth loops. Wes also talks about the importance of community support for user engagement and retention. Listeners can expect valuable guidance on navigating market challenges while implementing a product-led approach.

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 Know if a Channel is Working? A common dilemma many founders face is determining whether a new marketing channel is working. If you’ve ever wondered how long you should invest in a channel before calling it quits, you’re not alone. Here’s how I break it down: Give New Channels at Least 90 Days: If you’re starting fresh with a channel, 90 days is the minimum timeframe to give it. Less than that is almost never enough. Existing Channels Need Time Too: Even for established channels that you’re tweaking or optimizing, 90 days is still a good baseline. After that, look at the data to guide your decision. Focus on Leading Indicators: Whether it’s impressions on LinkedIn, open rates in email campaigns, or early engagement in SEO, you need to assess the leading metrics first. These are the earliest signs that a channel is gaining traction. For example, if you’re working on LinkedIn, impressions tell you whether your content is even being seen. Engagement and DM conversations are steps that follow, but focusing on what starts the funnel will help you decide if you should stick with it. 2. The Support, Success, or Sales Dilemma Another big question I often get asked is, “How do I know whether I need to hire for support, sales, or customer success?” This decision depends largely on where your business is in its growth stage and the roles you want to fill. Support Roles: These are typically more reactive—answering support tickets, maintaining a knowledge base, and troubleshooting. If customers are having common issues, or if onboarding is a bottleneck, it might be time to bring in a support team member. Success Roles: Customer success is more proactive. The goal here is to ensure customers get the most value from your product. This role could be key if your customers are signing up but not converting to paid users, or if you’re looking to drive expansion revenue. Sales Roles: Salespeople hunt for new business and close deals. If you’re looking to generate new demand or work with enterprise clients, this is the hire for you. Sales is more aggressive in its pursuit of growth, but if your inbound leads just need a quick demo, you may not need a dedicated salesperson—success could handle it. I suggest founders think about these roles in terms of function and their contribution to revenue growth. Where is the biggest gap in your customer journey? 3. Focus on Customers and Revenue-Generating Activities As entrepreneurs, it’s easy to get bogged down in tasks that feel productive but don’t directly drive growth. One of my favorite principles to live by is focusing on activities closest to your customers and revenue. Direct Conversations Over Complex Funnels: Fancy marketing automation systems might feel like progress, but especially early on, nothing beats direct customer conversations. Whether it’s cold outreach or calling people in your network, it’s the quickest way to gather real data and refine your approach. Avoid Procrastination via Fancy Funnels: Instead of hiding behind digital funnels and automation, get out there and sell directly. Speak to potential customers, get their feedback, and learn what truly resonates. Remember, your goal in the early days is to collect data, not over-engineer things. 4. Simple Ways to Test Paid Acquisition Paid acquisition is often intimidating, but there’s a simple approach that’s often overlooked—sponsorships in industry newsletters, podcasts, or YouTube videos. This tactic is low-risk and can provide quick insights into whether your message resonates. Why Sponsorships Work: Instead of figuring out the complexities of Google Ads or Facebook Ads, consider sponsoring content that already has your target audience’s attention. Whether it’s a niche podcast or a popular industry newsletter, you can place your offer in front of a highly relevant audience without a huge commitment. Discreet and Affordable: Unlike ongoing paid ads, sponsorships can be a one-off or a short-term commitment. You can test the waters, see if it works, and then decide whether to scale up. At Castos, we’re experimenting with this approach by sponsoring a few relevant newsletters and YouTube videos in our space. It’s a great way to validate messaging and offers before diving into more complex ad platforms. 5. The Most Important Thing for Founders The core principle for any founder is this: Work on the thing closest to your customers and revenue. All the fancy tools, automation, and branding strategies can come later. Start by doing what doesn’t scale—talking directly to your customers, gathering insights, and refining your product and messaging based on real feedback. Final ThoughtsThese are some of the questions that have come up repeatedly in my coaching sessions and with fellow founders. My best advice is to stay close to your customers, be data-driven in your approach, and always remember the 90-day rule when evaluating new channels. If you have more questions or want to dive deeper into any of these topics, feel free to reach out! Call to Action: If you’re interested in growing your business and leveling up your marketing, stay tuned for our upcoming episode where I’ll be sharing a deep dive into building a paid acquisition funnel for higher-ticket products.

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