Conservative vs Bold Returns

A discussion between Sam Parr and Shaan Puri reveals contrasting investment philosophies, highlighting the difference between conservative and aggressive approaches to wealth building. Shaan's perspective shifted dramatically after a successful exit, leading him to take bigger risks with potentially larger payoffs.

  • Investment Philosophy After Success:

    • Shifted mindset to act like someone with $100M
    • Takes larger bets than his actual bankroll can handle
    • Believes in ability to rebuild wealth if lost
    • Maintains confidence in recovering within 3 years if going to zero
  • Portfolio Strategy:

    • Keeps about 10% in cash
    • Roughly 50/50 split between public equities/crypto and angel investing
    • Manages a $4M/year rolling fund (mostly other people's money)
    • Exploring real estate but cautious about time commitment
    • Avoids other people's real estate funds
  • Growth Factors:

    • Benefited from strong stock market performance
    • Amazon stock appreciation (from $18.50 to $3,100)
    • Success in crypto (Bitcoin and Ethereum)
    • Additional income from podcasts and newsletters
  • Investment Style Inspiration:

    • Influenced by Chris Sacca's approach
    • Believes in making small initial bets
    • Follows up aggressively when identifying winners
    • Focuses on technology sector due to massive potential upside
  • Contrasting Approach with Sam Parr:

    • Sam: Higher probability of "pretty good" returns
    • Shaan: Higher probability of either "amazing or zero" returns
    • Acknowledges higher risk profile
    • Embraces potential for both massive wins and losses
13:50 - 14:16
Full video: 52:59
SP

Sam Parr

Host of MFM and fitness influencer

Sam Parr is a serial entrepreneur and business media pioneer.

In 2016, he founded The Hustle, a business news media company that started in his kitchen with just $12 and grew to eight figures in revenue.

Sam led the charge in making newsletters popular when few believed in their potential.

After four successful years, he sold The Hustle to HubSpot, a publicly traded company. Now operating as HubSpot Media, The Hustle reaches 3 million readers daily, employs a team of nearly 100, and has been the launchpad for dozens of its staff to found their own media companies and newsletters.

Sam remains the host of the popular business podcast, My First Million, and continues to start and sell companies. He also co-founded Hampton, a highly vetted community for entrepreneurs, founders, and CEOs, and teaches people to write better through his platform, Copy That.

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