Now-ish: The World According to Jason Fried

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In this episode of The Startup CEO Show, host Mark MacLeod sits down with Jason Fried, co-founder and CEO of 37signals, for an enriching conversation on startup leadership and maintaining a successful business partnership.

Jason shares valuable insights on keeping business costs lean, the inefficiencies of large teams, and the necessity of balancing intuition with business decisions. Learn how Jason's unique approach to day-to-day operations and his "joy of missing out" mindset has contributed to 37signals' sustained success. Discover his thoughts on remaining independent, the pitfalls of excessive venture capital, and the importance of genuine personal branding.

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Key highlights:

02:20 The Power of Respect and Admiration in Business Partnerships

06:50 Why Large Teams in Software Companies Can Be Inefficient

12:15 The Importance of Keeping Costs Low and Avoiding Early Venture Capital

18:00 Balancing Fights with Positive Outcomes in Startup Success

24:45 Jason’s Approach to Vision: Focus on Present and Immediate Future

30:15 Embracing the 'Joy of Missing Out' (Jomo)

35:50 Allowing Space for Creativity and Reflection

41:35 The Importance of Consistent Practice and Personal Satisfaction

47:20 Seeking Advice and Peer Groups for CEOs

53:40 The Value of Balancing Profit with Reinvestment

59:30 Finding Enjoyment and Energy in Work Processes

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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Contact Mark: https://markmacleod.me/