Seeking valuable insights on startup success and leadership strategies for CEOs? 🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/ ----------------------------------------------- How many times a day do you think "This meeting could have been an e-mail"? Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools. Go to https://fellow.app/ and discover the best way to enhance productivity today! ---------------------------------------------- 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. ------------------------- 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 -------------------------------- 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/ Connect on X/Twitter: https://twitter.com/markmacleod_ Contact Mark: https://markmacleod.me/