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Value Investing with Legends

Nov 1, 2019

of Omega Advisors. After getting his MBA from Columbia Business School, Leon joined Goldman Sachs as a Junior Analyst and ultimately built up Goldman Sachs' asset management division, GSAM. In 1991 Leon decided to follow his passion for money management and started his hedge fund, Omega Advisors, which became a family office in 2018. Leon is a member of The Giving Pledge and he takes great pleasure in giving back to those organizations and institutions that made a difference in his life. 

From humble beginnings, Leon benefitted greatly from the public education system while attending high school and college in the Bronx. Intuition has always played an important role in Leon’s life. After years of hard work to fulfill his goal of becoming a dentist, he followed that intuition and dropped out of dental school after just 8 days, forfeiting a full year of tuition and expenses. That misstep into dentistry put Leon on the path that would lead to Columbia Business School and a job at Goldman Sachs right after graduation, which he credits with changing the trajectory of his life. 

On this episode, Leon and I talk about how Leon went from dreams of dentistry to a successful career in the investment world, Leon’s approach to value investing, Leon’s career path at Goldman Sachs, why Leon founded Omega Advisors, how politics affects policy, Leon’s take on the current state of the financial markets, Leon’s approach to philanthropy, and so much more!


Key Topics:

  • The two factors to which Leon attributes his success (2:56)
  • Why Leon wrote a letter to President Obama (3:12)
  • How getting an MBA from Columbia Business School changed the trajectory of Leon’s life (4:22)
  • Why Leon dropped out of dental school (4:36)
  • The key role intuition played from early in Leon’s life (6:05)
  • How Leon ended up working at Goldman Sachs right after graduating (6:56)
  • Leon’s introduction to value investing at Columbia Business School (8:12)
  • Leon’s career at Goldman from Junior Analyst to Partner (9:36)
  • The benefits of the close working relationship between sales, trading, and research at Goldman (11:08)
  • The dual roles Leon had to play in the 70s (11:42)
  • Leon’s favorite aspect of doing investment research (12:37)
  • Why Leon keeps up to date with the micro- and macro-activities of the business world (13:44)
  • The origin of Goldman Sachs Asset Management (14:42)
  • The inception of Omega Advisors Hedge Fund and its evolution into a family office (16:50)
  • Why Leon decided to retire (18:05)
  • What Leon told Warren Buffett about The Giving Pledge (18:48)
  • Why Leon decided to leave Goldman Sachs (19:16)
  • How Leon’s brush with the S. Securities and Exchange Commission (SEC) positively impacted him (21:18)
  • Leon’s investment strategy when he started Omega Advisors (22:24)
  • The importance of surrounding yourself with knowledgeable people (23:06)
  • How regulatory changes have driven up the cost of business (24:01)
  • Why Leon attributes value orientation as the driver behind the success of Omega Advisors (25:35)
  • Leon’s current investment strategy (26:02)
  • Leon’s perspective on the current state of the financial markets (27:33)
  • Why we should be worried about the amount of debt currently being created in the economy (29:46)
  • What Leon considers to be a “normal” state for the markets (31:07)
  • How government policy has contributed to the current income disparity (33:14)
  • The problem with wealth tax (34:31)
  • Why Leon believes America’s commitment to capitalism is so important (37:55)
  • How the current state of politics is affecting the creation of sensible policy (39:42)
  • The four things you can do with money (42:37)
  • Leon’s philanthropic endeavors (43:54)
  • And much more!


Mentioned in this Episode:


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