20VC: Altimeter's Brad Gerstner on Why Supercycles and the Powerlaw is the Most Important Thing In Investing, Why Portfolio Diversification is the Opposite of Risk Mitigation and The #1 Question Brad Asks All New Recruits


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Brad Gerstner is the Founder and CEO of Altimeter, a life-cycle technology investment firm that manages public and private portfolios. Brad has personally participated in more than 100 IPOs as a sponsor, anchor, and investor. Brad’s notable deals include Snowflake, Mongo, Bytedance, Gusto, Unity, Okta, dbt, Modern Treasury, EPIC Games, Hotel Tonight, and Zillow. Prior to founding Altimeter, Brad was a 3-time co-founder where he sold all three businesses (to IAC, Google, and Marchex), a founding principal at General Catalyst; a securities lawyer, a former Deputy Secretary of State of Indiana, and a pilot.

In Today's Episode with Brad Gerstner We Discuss:

1.) From Humble Beginnings in Indiana to 100 IPOs:

  • When did Brad realize his original love of finance and entrepreneurship?
  • What one single question does Brad ask all potential new recruits to determine if they have hustle?
  • What does Brad know now that he wishes he had known at the beginning of his career?

2.) The Power Law and Supercycles:

  • What is a power law? Why is it the single most important thing in investing?
  • How do the best investors in the world build a framework around supercycles?
  • How does Brad approach market sizing? How does Brad think about market creation when aligning that to his thesis of investing in power laws?
  • How does Brad determine if a large opportunity is a "super-cyle" or a short, time-stamped fad that is unsustainable? How does Brad assess the importance of market timing?

3.) Building Anti-Fragile Portfolios:

  • Portfolio Construction: Why does Brad disagree that the answer to risk mitigation is portfolio diversification? How many companies is enough companies for a diverse portfolio?
  • Price Sensitivity: How does Brad reflect on his own relationship to price? How does this process and mindset change on re-investments? What is needed for Brad to re-invest?
  • Time to Exit: How does Brad analyze when is the right time to exit a position? What are the single biggest mistakes people make when it comes to timing their exit?

4.) The Venture Landscape: Today, What is Happening?

  • Why does Brad believe what has happened over the last 24 months is a great disservice to founders?
  • What are the biggest examples of a complete lack of investor discipline?
  • Why does Brad believe that for all positions valued over $500M, we should apply a 20% discount?
  • Is today's pricing actually just the new normal? How has the public market pricing impacted the deployment of growth stage checks? How will this play out in the next 12 months?
  • Why does Brad believe there is "not blood on the streets yet"? How does the speed of interest rate change impact our ecosystem so dramatically?

Items Mentioned in Today's Episode:

Brad's Favourite Book: The Snowball: Warren Buffet and the Business of Life

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