Jason’s background

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The reason I think it's great for entrepreneurs to start bootstrapping is because they just have more practice making money, and they get better, and better, and better at the fundamental skill you need to have ultimately to run a successful business, which is to make money. Hopefully, I don't come off as encouraging everyone to be like me. I'm not saying that at all. What I'm saying is, this is a way to be. It's an alternative to what you're often hearing in our industry, which is, "Go big or go home. Raise a bunch of money and get huge, and unicorn status," and the whole thing. That's a way. Just know though that basically almost nobody makes it that way. Really, almost nobody really makes it that way, and there's a lot more room to make it, and to build a successful business, if you throw out that outlier and look at all the other places you can land as a business.

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Today, my guest is Jason Fried. Jason is the Co-Founder and CEO of 37signals, which makes Basecamp and HEY, and soon a few more products including a competitor to Slack. 37signals is a very different type of company. They have no investors, no board. They have no plans to go public. They never want to sell their business. They've made a profit for 24 years in a row. They have over 100,000 customers and make tens of millions of dollars in profit each year, which most VC-backed companies never make a dollar of. All of this profit filters down to the founders and employees because they have no investors. Most founders, by default, will go down the venture route raising money from VCs and Angels. For many types of companies, that is necessary.

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But it's also important to know that there is a different option available, and it can be much more fulfilling and fun, and even much more lucrative, by bootstrapping your idea. In my conversation with Jason, we get into why constraints like small teams and less cash often lead to better outcomes. Why gut and instinct is underappreciated as a decision-making tool. Why planning long-term is often a mistake. Why work doesn't have to feel like war. Why we should focus on playing infinite games. When it makes sense to consider raising venture capital versus bootstrapping. How to actually bootstrap your startup, so much more. Jason is fascinating, and he's got a lot of wisdom to share. I'm excited to be able to bring you this conversation. With that, I bring you Jason Fried, after a short word from our sponsors.

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This episode is brought to you by Coda. You've heard me talk about how Coda is the doc that brings it all together, and how can help your team run smoother and be more efficient. I know this firsthand because Coda does that for me. I use Coda every day to wrangle my newsletter content calendar, my interview notes for podcasts, and to coordinate my sponsors. More recently, I actually wrote a whole post on how Coda's product team operates. Within that post, they shared a dozen templates that they use internally to run their product team, including managing the roadmap, their OKR process, getting internal feedback. Essentially their whole product development process is done within Coda. If your team's work is spread out across different documents and spreadsheets, and a stack of workflow tools, that's why you need Coda. Coda puts data in one centralized location, regardless of format, eliminating roadblocks

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