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​Podcast, YouTube, Blog​

Dear founder,

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Recently, I’ve been pondering the difference between being sincere and being serious, especially in the context of entrepreneurship. This reflection was sparked by an article I read about how the most successful people are sincere but not overly serious. It’s a fascinating concept that ties into the idea of playing the infinite game versus the finite game—a theme I’ve explored in my books “Zero to Sold” and “The Embedded Entrepreneur.” Both entrepreneurship and audience-building are very much infinite games: you can’t truly win them, but you win by remaining able to keep playing.

I highly recommend Simon Sinek’s Infinite Game if you want to dive more into this approach. It will impact much more than your business: you’ll see things like purpose, health, love, and family in completely new ways as well. You’ll likely focus more on the infinite games because you can spot them more easily.

Both finite and infinite games have their place. I’m saying this in the middle of a lot of soccer championships, both in the Americas and in Europe. These are quite literally finite games: 90 minutes, clear rules, static teams, and obvious winners and losers. And for competitive sports, that’s great: you get action, suspense, hope, despair, and snackable experiences. Players are very serious throughout these games — you can quite literally see it when they yell at the referee every 3 minutes.

But there is a larger, infinite game at play here too: the one where every nation participating keeps an ever-improving set of soccer leagues to find their best players. These leagues make long-term decisions, because they can’t “win soccer” — they just want to keep participating in these amazing events. They’re sincere about that. These soccer organizations put their goals and vision out there, and they seek participation, buy-in, and the support of their peers.

In the world of entrepreneurship, those who play finite games are often very serious about short-term wins, sometimes at the expense of their own long-term vision. On the other hand, those who approach their ventures with sincerity and almost radical honesty are more likely to focus on the bigger picture, willing to sidestep immediate gains if they might impede the ultimate realization of their vision.

This philosophy has been at the forefront of my mind as I’ve been building Podscan.fm in public over the last couple of months. For those who aren’t familiar, Podscan is a podcast marketing and brand analytics tool I’ve been developing. Building in public has been an incredible way to demonstrate sincerity and make my entrepreneurial journey accessible to others.

One of the most interesting aspects of this path has been challenging the conventional wisdom about how we should communicate with different types of customers. There’s often an expectation that the larger the customer—say, an enterprise or big business—the more serious and formal we need to be in our communication. Conversely, when selling to individuals or indie hackers, we’re told we can be more quirky and personal. At least, that’s what we see happening in the social media channels around us.

But as I’ve delved deeper into marketing and sales for Podscan, I’ve noticed something intriguing: there’s a lot of seriousness in the world of podcast marketing and brand analytics, but not always a lot of sincerity. And you know what? I’d much rather be open, honest, and approachable than put on a facade that doesn’t reflect who I really am.

This realization has been reinforced through my interactions with people trialing Podscan. Whether they work for big businesses or are solo founders, at the end of the day, they’re real people. And people can distinguish sincerity from seriousness. They can spot when someone is genuinely engaged versus when they’re using a formulaic approach or templated responses.

It’s reminded me of a core principle I’ve been reading in so many serial entrepreneur’s success stories: successful entrepreneurship isn’t just about building a business to flip quickly or make money online. It’s about adopting a mindset, a way of thinking that’s geared towards playing the infinite game.

In the context of Podscan, playing the infinite game means focusing on building something of lasting value that keeps people coming back. It’s about having enough revenue to close some deals and pass on others if they don’t align with our long-term vision. It’s about building meaningful relationships with our users and continuously improving our product based on their feedback.

This approach requires sincerity, and I’ve tried to embody this in all my communication channels. I strive to be responsive and responsible to our users, whether they’re chatting with me in our support system or sending emails. I’m transparent about what Podscan can and can’t do, and I’m not afraid to suggest alternatives if our product isn’t the right fit. I’ll say no because I want to overcome that fear we all know: “what if they don’t buy?” Well, I’d rather have a happy non-customer than an unhappy customer.

When it comes to sharing the story of Podscan as I build it in public, I’ve made a conscious decision to be completely honest, too. I don’t inflate numbers or make promises I can’t keep. Why? Well, partly because I believe in the power of transparency and the eventual reciprocity it creates: if I’m honest and open, I will attract people who are like that too, and they’ll help me build a better business, But, I also do this because, frankly, I’m too lazy to lie. It’s hard work to keep lies consistent, and I’d rather put that energy into building a better product.

This commitment to sincerity is at the core of what I want Podscan—and my entire entrepreneurial journey—to represent. It’s about being honest, user-centric, and voluntarily truthful. I want to inspire others who might be on a similar path, and maybe even deter those who aren’t ready for the challenges that come with building a business.

Ultimately, my goal is to create a presence that’s positive and trustworthy. Because here’s the thing: if you want to play the infinite game, you can only keep playing if other people trust you to follow the rules. This is especially crucial when you’re starting out, trying to build something from nothing.

I’ve found that this approach attracts people and opens up conversations that have real impact on the business I’m building. Over the past few weeks, I’ve asked dozens of technical and business questions on Twitter, always in a humble and engaging way. The responses I’ve received have provided valuable insights, from advice on algorithms to suggestions for optimizations.

This is what entrepreneurship means to me: sincerity, not seriousness. It’s about being transparent and honest about what I’m doing with Podscan, while still having fun and engaging with the community in an enjoyable way. It’s about playing the infinite game, focusing on long-term value creation rather than short-term gains.

As I continue to build and grow Podscan, I’m committed to maintaining this approach. I believe it’s not just good for business—it’s good for the soul. And who knows? Maybe it’ll inspire a few more entrepreneurs to choose sincerity over seriousness in their own journeys.

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I'll share a few updates about my SaaS on the pod, and if you want to track your brand mentions on podcasts, please check out podscan.fm — and tell your friends!

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