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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

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Jan 6, 2023

Jason Fried, Co-founder and CEO of 37signals and author of 'Rework,' shares his unique journey in entrepreneurship. He reveals why traditional goals hinder success and discusses his decision-making process anchored in a single, guiding question. Fried explains his choice to eliminate politics from the workplace and reflects on the challenges of losing a third of his team overnight. He also emphasizes the importance of trust in leadership and the value of sustainable growth over sheer numbers.

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ANECDOTE

Basecamp's Origin

Jason Fried, initially a freelance web designer, co-founded Basecamp with friends out of boredom with solo work.
Basecamp, originally a tool for internal project management, became a successful product due to client demand.

INSIGHT

Running From and Towards

Jason Fried prioritizes independence and autonomy, running his own business without external funding.
His long-term goal involves stepping away from his current role and exploring non-computer-based pursuits.

INSIGHT

Risks of Unprofitable SaaS

Unprofitable, venture-funded SaaS companies face significant risks during market downturns.
Their focus on market share over profitability may lead to layoffs and austerity measures.

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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?