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Dinner With Michael Ovitz

What I learned from having an intense and fun 3 hour dinner with Michael Ovitz. 1: Mediocrity is always invisible until passion shows up and exposes it. 2: There's no ceiling on where you can push your profession. 3: Don't be unequally yoked. Pick partners that have the same ambition as you. 4: Read biographies. Know everything about the history of your industry. 5. Have a profound sense of belief. The world is very malleable. 6: There’s opportunity hiding in plain sight. 7: By endurance we conquer. 8: Work 10% less. Optimize for the long term. 9. Surround yourself with people who will tell you the truth. 10: Retirement is lame. ---- Ramp gives you everything you need to control spend, watch your costs, and optimize your financial operations —all on a single platform. Make history's greatest entrepreneurs proud by going to Ramp https://ramp.com/ and learning how they can help your business control your costs and save more. https://ramp.com/ ---- Founders Notes gives you the ability to tap into the collective knowledge of history's greatest entrepreneurs on demand. Use it to supplement the decisions you make in your work. Get access to Founders Notes here. https://www.foundersnotes.com/ ---- Join my free email newsletter to get my top 10 highlights from every book https://davidsenra.com ---- “I have listened to every episode released and look forward to every episode that comes out. The only criticism I would have is that after each podcast I usually want to buy the book because I am interested so my poor wallet suffers. ” — Gareth Be like Gareth. Buy a book: All the books featured on Founders Podcast https://amzn.to/4iev7mS

David Senrahost
Mar 14, 202527mWatch on YouTube ↗

CHAPTERS

  1. 0:00 – 4:08

    How the Dinner with Michael Ovitz Came About

    David Senra explains that he flew to New York for a three-hour dinner with Michael Ovitz, arranged through a mutual friend named Rick. He describes how he processes these dinners by writing down ideas afterward rather than recording or taking notes.

    • •Ovitz told Senra he had listened to four Founders episodes the day before
    • •Senra has done similar dinner episodes with Charlie Munger, Sam Zell, Brad Jacobs and John Mackey
    • •He doesn't record or take notes during dinner
    • •He is also making an episode on Ovitz's autobiography
  2. 4:08 – 6:14

    Mediocrity Is Invisible Until Passion Shows Up

    Senra's first lesson is that mediocrity is invisible until passion exposes it, and he says Ovitz does nothing casually. He gives examples from Ovitz's mail room days and his two-year pursuit of a director.

    • •Ovitz read every file in the William Morris filing room, which he called an encyclopedia of entertainment
    • •None of the other trainees did the same
    • •He worked on one director for two hours a day for two years
    • •He got the director scripts before the director's own agent did
  3. 6:14 – 9:01

    No Ceiling on Your Profession

    Senra draws on Tim Grover's observations about Michael Jordan and Kobe Bryant to illustrate figuring out what works for you. He then lists how Ovitz kept expanding what a talent agency could do.

    • •Grover wrote that the greats figure out what works for them regardless of what others do
    • •CAA agents serviced clients together as a swarm
    • •CAA created opportunities and packages rather than just fielding offers
    • •Ovitz moved into corporate M&A and marketing consulting
    • •Ovitz said that doing new things brings criticism from outsiders
  4. 9:01 – 11:08

    Don't Be Unequally Yoked: Choosing Partners

    Senra connects Ovitz's advice about partners having the same ambition to the church phrase about being unequally yoked. He recounts how partners may label big ideas a distraction and how Ovitz keeps trusting people after being betrayed.

    • •Partners with lesser ambition lead to criticism from insiders as well as outsiders
    • •Partners may call new initiatives a distraction
    • •Two of the partners who betrayed Ovitz were close friends
    • •Ovitz said three people screwed him over out of a thousand, and he won't let that foreclose future partnerships
  5. 11:08 – 12:53

    Read Biographies and Know Your Industry's History

    Senra covers Ovitz's line that only founders understand founders and his modeling of himself on Lou Wasserman. Ovitz also advised Senra to lean into lesser-known founders.

    • •Ovitz read biographies voraciously as a youth, including Carnegie and Rockefeller
    • •He confirmed to Senra that he still thinks Lou Wasserman was the best
    • •Reading life stories shows you that other founders go through the same things
    • •Ovitz advised Senra to feature more unknown founders such as Daniel Ludwig and Estee Lauder
  6. 12:53 – 14:05

    Profound Belief and a Malleable World

    Senra shares Ovitz's line that nothing in Hollywood is anything until it's something, made real through a profound display of belief. He pairs it with Marc Andreessen's similar remark about the world being malleable.

    • •Ovitz wrote that insisting a shifting set of possibilities is a movie eventually makes it one
    • •Andreessen modeled his venture firm on what Ovitz did at CAA
    • •Andreessen said the world reconfigures itself around those who go for it with maximum energy
    • •Ovitz sees what things could be, not what they are
  7. 14:05 – 16:10

    Opportunity Hiding in Plain Sight

    Senra argues that Ovitz saw unlimited opportunity in things others discarded. He cites Ovitz's deals on Shogun, Tootsie and Rain Man and compares them to other founders.

    • •Shogun became a massive miniseries after sitting unused at another agency
    • •Tootsie was considered dead for six years
    • •Rain Man was rejected by others and made over $400 million
    • •Leon Hess and Sam Zemurray built businesses from discarded product
    • •75 people turned down the Cowboys before Jerry Jones bought them
  8. 16:10 – 19:04

    By Endurance We Conquer and the Pace of Work

    Senra discusses perseverance, quoting Ovitz's line that everyone else stopped because it was hard and he didn't. He ties it to Steve Jobs on perseverance and to Herb Kelleher's story about speed at Southwest.

    • •Ovitz wrote that everyone stopped because it was hard, but he didn't stop
    • •Steve Jobs said about half of what separates successful entrepreneurs is perseverance
    • •Ovitz expects extremely fast turnaround, wanting on Friday what he asked for Thursday night
    • •Herb Kelleher told a marketing executive he meant a campaign next Wednesday, not months away
  9. 19:04 – 21:54

    Work 10% Less and Optimize for the Long Term

    Senra recounts Ted's advice to Ovitz that he could have worked 10% less without hurting his success, and Ovitz's reply at dinner that this applies after the rise. Senra concludes founders should optimize for durability.

    • •Ovitz admitted he didn't take Ted's advice and could have worked up to 20% less
    • •At dinner he said the advice applies but not during the rise
    • •CAA was underfinanced early, with founders taking second loans on their houses
    • •Most profits come decades out, as with Microsoft, Apple, Oracle and Walmart
    • •Don't optimize for growth at the expense of durability
  10. 21:54 – 24:54

    Surround Yourself with Truth-Tellers

    Ovitz said he cannot stand yes-men, and Senra describes how Rick earns Ovitz's loyalty by being direct. Senra then lists how other founders sought unfiltered information.

    • •Ovitz said he cannot stand yes-men
    • •Ovitz gave Senra candid criticism at dinner
    • •Bezos let customers email him directly
    • •Paul Orfalea used a voicemail system for employees
    • •Sam Walton and Jim Casey went to the front lines to hear directly from workers
  11. 24:54 – 27:02

    Retirement Is Lame and Closing Recap

    Senra quotes Jeff Bezos saying retirement is lame and says Ovitz feels the same, noting retired friends of his lose their sharpness. He ties this to other dinner guests, recaps all ten lessons, and previews the upcoming episode on Ovitz's autobiography.

    • •Ovitz said friends who retired to golf or gardening became less sharp and vibrant
    • •Munger, Zell, Jacobs and Mackey share the need to keep pushing
    • •Retirement is fatal for a certain personality type
    • •Senra recaps the ten lessons
    • •The next episode covers Ovitz's autobiography

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