Rogue Startups

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 employs for successful PLG implementation.

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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!

Wes is an entrepreneur, author, and product-led coach. Over 500,000 people have read his Product-Led Growth book and listened to the ProductLed Podcast.

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“Why Nations Fail” by Daron Acemoglu and James A. Robinson

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Founder Insights

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.

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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:

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.

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.

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?

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.

Remember, your goal in the early days is to collect data, not over-engineer things.

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.

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.

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 Thoughts
These 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.

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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.

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.

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.

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.

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.

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.

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.

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 [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!

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.

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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:

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 [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!

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.

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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 [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!

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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.

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.

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Founder Insights