20VC: Why Financial Planning and Goals Do Not Work, The Decision to Ban Politics in the Workplace and Losing 1/3 of the Team Overnight & The One Question That Will Drive All Decision-Making for Leaders with Jason Fried, CEO @ 37Signals

Posted on 6th January 2023 by Harry

Jason Fried the Co-Founder and CEO at 37signals, makers of Basecamp and HEY. Over an incredible 21 year journey, Jason and his co-founder David have scaled Basecamp to become the communication tool trusted by millions. 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 Todays Episode with Jason Fried We Discuss

1. From Web Design Agency to Founding Basecamp:

  • What was the a-ha moment for Jason when they had to make the pivot from a design agency to going full-time launching and running Basecamp as a SaaS company?
  • What is Jason running towards? What is he running from?
  • What is the single biggest fear that Jason is trying to avoid?

2. Jason Fried: The Leader:

  • Why does Jason believe he is running from his position as leader and CEO @ Basecamp?
  • Why does Jason not like or agree with goals or targets? Why are they not helpful?
  • How does Jason make decisions today as a leader and CEO? What one question does he ask that determines his decision-making process?
  • Why does Jason never compare himself to the competition? Why does he believe competition is for losers?

3. Jason Fried: The Politicisation of Leadership:

  • Why did Jason and David decide to not allow politics in the workplace?
  • How did they manage with 1/3 of their team leaving overnight? How was that experience for them personally? How did it impact the company? Is there anything they would do differently?
  • Does Jason believe we will see the continued politicization of leadership in the coming months?
  • How would Jason advise other CEOs when it comes to taking a stance on politics?

4. Jason Fried: Building the Best Team:

  • What is the one question that determines whether you made a good hire?
  • Why does Basecamp start with hiring all employees on a week-long project contract?
  • Why does Jason believe the best CEOs approach management as the art of the individual?

5. Jason Fried: The Partner, Father and Husband:

  • Jason and David have been partners for 21 years, why does Jason believe it is helpful that they do not see each other much?
  • Is it right for co-founders and partners to be friends?
  • What have been Jason’s single biggest lessons on what it takes to be the best husband?
  • What does great fatherhood mean to Jason? How has it changed over time?

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