Beyond Small Bets — Embracing the Big Play — The Bootstrapped Founder 332


Dear founder,

I’m at an interesting stage of my entrepreneurial journey, seeing several of my worlds colliding. The frameworks I’ve been using to get where I am are both working really well and starting to show their limitations.

For years, I operated under the paradigm of having many small bets, a framework popularized by Daniel Vassallo in the indie hacker community. I’ve been part of his Small Bets community and even held workshops there occasionally. The idea is to treat your ideas like cattle - try many different things and see what sticks.

This approach led me to build a diverse portfolio:

  1. A media business with a newsletter, podcast, and YouTube channel
  2. Consulting, mentoring, and workshops
  3. Several software-as-a-service businesses

All of these projects ran side by side, each a small bet in its own right. This stage was all about exploration, variety, and experimentation. I was looking for signals in the noise, trying different formats and approaches.

But recently, something changed. My latest software project, Podscan, has shown signs of product-market fit like I’ve never seen before. This success is forcing me to restructure my focus, which has become a challenge. I’m so used to having parallel entrepreneurial efforts that pulling my focus away from them and maximizing the time and effort I put into Podscan is difficult.

The challenge is overcoming my inhibition to change - making a decision to prioritize one thing and deprioritize others that have been big parts of my life for years. It’s not just about personal expectations, but also managing the expectations of the people who’ve been part of my journey. When you build a media business, you build it with and in front of people. A podcast is nothing without its listeners, a newsletter nothing without its readers.

So, the question isn’t whether I should keep running my media business - that’s a clear yes. The question is how much of it I want to run while spending most of my time on Podscan. I could do less of it, give it to somebody else, or invite someone to work for me.

I’ve been subconsciously moving towards less media and more software-as-a-service for a while now. My income has been mostly dictated by sponsorships over the last couple of years, which provided both motivation and structure. If someone’s paying you for eight podcast episodes a month, you have to create two episodes a week. If they place newsletter sponsorships two months in advance, you know you have to create newsletters for a couple of months.

But I think my subconscious mind understood that this accountability was actually getting in my way. Over the last couple of months, I’ve been saying no to sponsorships more and more. I’ve pulled out of long-term agreements, trying to deprioritize the mental load of having to create content every week so that I could focus on the software business.

The potential outcomes are on different scales. Getting another 20,000 newsletter subscribers would be wonderful, but having another couple hundred recurring customers in a software business, creating a business worth millions, is a completely different ballgame. Podscan is effectively a marketing amplifier, a tool that helps people make money and get their jobs done. Focusing on this could have a much stronger impact on wealth-building and the field I work in.

I’ve been feeling this shift more strongly since getting funding for the business and receiving positive feedback from customers. Now that I’ve realized this, I’m making a more conscious effort to adapt.

I’ve decided to make the interview part of my podcast more flexible. I’ll interview people when I want to, not on a weekly basis, and I’ll focus more on the core values of independence, progressive business entrepreneurship ideas, and solopreneurship. I want to keep the interviews relevant to what Podscan is currently struggling with, bringing my real-world problems to experts in their fields and hearing about their experiences and frameworks.

My weekly solo episodes will remain as an accountability regimen to myself and to everyone who wants to see me succeed on this journey. As I spend more time building Podscan, there will be more for me to talk about on the podcast as well.

It’s hard to change something that’s been working well for almost four years, but I have to remind myself that change is constant in entrepreneurship. Five years ago, this podcast didn’t exist. Three years ago, it was just me talking about interesting things. Two years ago, I was sheepishly getting into interviews. A year ago, it was my main source of income. Why wouldn’t change keep happening?

My strategy now is to focus on Podscan as my main dish and keep everything else as side projects. I need to be adaptable to changing circumstances. Maybe Podscan really takes off and I have to pause my other efforts, or maybe it finds an equilibrium where I can hire someone to help me with it and I can spend more time on my other efforts. I don’t need to know now - I just need to be able to make the choice when the time is right.

If you’re struggling with priorities and focusing on things, consider that nothing is ever truly lost if you keep a channel open. It’s fine to pause things to see if they impact your productivity overall. It’s okay to dial them down a little if that helps you significantly.

This is a common problem for solopreneurs and founders who have to juggle many different things at the same time. We only have a dozen or so hours in the day to distribute amongst the many things we could be doing. If one of your small bets turns out to be the golden goose, you owe it to yourself and your future self to question if your current priorities are serving you. That’s why I’m changing mine.

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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Arvid Kahl

Being your own boss isn't easy, but it's worth it. Learn how to build a legacy while being kind and authentic. I want to empower as many entrepreneurs as possible to help themselves (and those they choose to serve).

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