20VC: Basecamp CEO Jason Fried on His Relationship To Risk, Money, Vulnerability and Self-Doubt, Fantasising About Being Fired, How To Optimise Decision-Making and Minimising Regret
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC
4.4 • 637 Ratings
🗓️ 22 March 2021
⏱️ 44 minutes
🧾️ Download transcript
Summary
Jason Fried is the Founder & CEO @ Basecamp, the project management and team communication tool trusted by millions. Over an incredible 22 year journey, they have scaled to over 3.5M accounts and in 2020 they went back to being a multi-product company with the launch of their integrated email client & service, HEY. Jason is also the co-author of the widely acclaimed, ReWork and has also made several angel investments in the likes of Intercom, Gumroad and Hodinkee to name a few.
In Today’s Episode You Will Learn:
1.) How Jason Fried made his way into the world of startups and came to found one of the leading project management and team communications tools in the form of Basecamp?
2.) How does Jason analyse and evaluate his relationship to money? Why does Jason believe that he has this inherent downside protection when it comes to money? How does he structure his personal finances between stocks, cash, crypto etc etc? What have been some of Jason's biggest lessons when it comes to tying happiness to monetary levels?
3.) What does Jason mean when he says, "I have a fantasy of getting fired"? How does Jason think about knowing when is the right time to step away from the business? What would he like to do with that time? How does Jason feel about the challenge of tying his identity to his company? What are the dangers of doing so?
4.) How does Jason approach decision-making frameworks? What does Jason believe is the right way to respond when a decision does not go as planned? Where do many make mistakes here? Does Jason feel regret with decisions? How does Jason try and minimise regret?
5.) How does Jason feel about his biggest insecurities as a leader and CEO today? What are Jason's views on a CEO's ability to have self-doubt and be vulnerable? How have his views on this changed over the years? In what way has having kids impacted Jason's operating mindset? How has it changed what he values and appreciates?
Item’s Mentioned In Today’s Episode
Jason’s Favourite Book: In Praise of Shadows
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Transcript
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| 0:00.0 | Welcome back. This is 20VC with me, Harry Stebbings. Now, you might have noticed that the last |
| 0:03.9 | few months of shows have been a little bit more personal. They've been focused on the traits and |
| 0:07.7 | mindsets of great leaders, and the best of these shows always go off script. Now, there is no |
| 0:12.4 | greater example of this going off script totally than today's episode with the one and only Jason |
| 0:17.0 | fried. Luckily, he was okay with my wayward questions, but to Jason, he's the co-found |
| 0:21.2 | and CEO at Basecamp, the project management and team communication tool trusted by millions. |
| 0:26.3 | Over an incredible 22-year journey, they've scaled to over 3.5 million accounts, and in 2020, |
| 0:31.6 | they went back to being a multi-product company with the launch of their integrated email client |
| 0:36.1 | and service, Hey. Jason's also the co-author of the widely acclaimed rework and has made several angel investments |
| 0:41.7 | in the lights of Intercom, Gum Road and Hodinky to name a few. |
| 0:45.1 | I'd also want to say a huge thank you to his wonderful co-founder, DHH, some fantastic |
| 0:49.4 | questions suggestions today. |
| 0:50.8 | David, I really do so appreciate that. |
| 0:52.9 | But before we move into the show today, |
| 0:54.3 | I have to say I just love using AngelList's fund admin platform to manage my investments. The team |
| 0:59.2 | platform at AngelList takes care of all my back office needs so that I can focus on working |
| 1:03.4 | with great founders. Leading fund managers have made over 10,000 investments into 6,000 startups |
| 1:08.9 | via AngelList, all online and all in one place. And with recently |
| 1:12.6 | announced rolling funds, you can easily find and invest in these top fund managers on AngelList.com |
| 1:18.2 | forward slash rolling. And speaking of amazing products there with AngelList, last month I had |
| 1:22.5 | Jeff Seiber and Wayne Chang on the show from Digits. Simply put, they're two of the best |
| 1:26.3 | founders I've met and they're creating the most intuitive financial software you've ever used, automatically |
... |
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