Jason Fried challenges your thinking on fundraising, goals, growth, and more

The reason I think it's great for entrepreneurs to, to start bootstrapping is 'cause they just have more practice making money. 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 am saying is this is a way to be. It's an alternative to what you're often hearing in our industry, which is, like, go big or go home, raise a bunch of money and get huge and unicorn status and the whole thing. Like, that's a way. Just know, though, that basically almost nobody makes it that way. Like, 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.

(instrumental music) 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. And 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, and for many types of companies, that is necessary. 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. This episode is brought to you by Coda. You've heard me talk about how Coda is the dock that brings it all together, and how it 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, and 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, and 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 that can slow your team down. Coda allows your team to operate on the same information and collaborate in one place. Take advantage of this special limited time offer just for startups. Sign up today at coda.io/lenny and get $1,000 startup credit on your first statement. That's coda.io/lenny to sign up, and get a startup credit of $1,000. Coda.io/lenny. This episode is brought to you by Sidebar. Are you looking to land your next big career move, or start your own thing? One of the most effective ways to create a big leap in your career, and something that worked really well for me a few years ago, is to create a personal board of directors, a trusted peer group where you can discuss challenges you're having, get career advice, and just kind of gut check how you're thinking about your work, your career, and your life. This has been a big trajectory changer for me, but it's hard to build this trusted group. With Sidebar, senior leaders are matched with highly vetted, private, supportive peer groups to lean on for unbiased opinions, diverse perspectives, and raw feedback. Everyone has their own zone of genius, so together we're better prepared to navigate professional pitfalls, leading to more responsibility, faster promotions. And bigger impact. Guided by world-class programming and facilitation, Sidebar enables you to get focused, tactical feedback at every step of your journey. If you're a listener of this podcast, you're likely already driven and committed to growth. A Sidebar personal board of directors is the missing piece to catalyze that journey. Why spend a decade finding your people when you can meet them at Sidebar today? Jump the growing wait list of thousands of leaders from top tech companies by visiting sidebar.com/lenny to learn more. That's sidebar.com/lenny. Jason, thank you so much for being here, and welcome to the podcast.