Asking A Billionaire Investor How To Prepare For The Economic Collapse (#371)

About this video

Andrew Wilkinson, founder and CEO of Tiny (a holding company that acquires internet businesses), joins Sam and Shaan to discuss preparing for economic uncertainty, personal investment strategies, and new business ventures. The hosts explore Andrew’s stress-testing approach to business resilience, his shift toward conservative venture investing and secondary deals, his personal portfolio focused on cash and Pershing Square Holdings, and his contrarian strategy of buying businesses during downturns rather than making venture bets.

Key takeaways

• Andrew stress-tests businesses by modeling scenarios where revenue drops 50-70% to identify vulnerabilities in debt, contracts, and cash reserves; he emphasizes the danger of missing opportunities during downturns due to illiquidity, not just the risk of bankruptcy.
• During economic uncertainty, Andrew is pivoting his venture strategy toward secondary buyouts, minority deals, and structured arrangements with downside protection, while also incubating low-cost internal businesses that solve real P&L problems rather than making high-valuation startup bets.
• Andrew holds approximately 50% of his personal net worth in US Treasury bills and 50% in Pershing Square Holdings (trading at a discount to net asset value), waiting to acquire businesses personally; he separates personal liquidity from his 90% net-worth stake in Tiny to ensure optionality if conditions deteriorate.
• Shaan is taking the opposite approach: deploying more venture capital now because founders with conviction are self-selecting (less-committed ones quit), valuations have dropped 40-60%, and he can buy cheaper while exiting 7-10 years later in a recovered market, though Andrew cautions against anchor bias—businesses may be overvalued even at lower prices.
• Andrew discusses incubating new businesses like a procurement/negotiation service (Buyer, which sold to Ramp) and a credit optimization company, starting with capital-light models that generate revenue within 2-3 months rather than pursuing unprofitable ventures for years.

Episode details: published October 6, 2022 · 49K views · 1:23:49 long. Summary written by Self Growth Videos from the episode itself. The business ideas, figures and results discussed are the hosts’ and guests’ own claims, shared as brainstorming and entertainment — not verified facts and not investment advice.

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