How Billionaires Invest
How Billionaires Invest covers how family offices divide capital and investment work, and how investors assess managers, founders, risk and fit with their expertise. The pages range across public markets, real estate, private companies, healthcare, crypto and early stage deals. Richard C. Wilson explains portfolio choices and direct investing, while guests share how they make decisions and manage investments.
Investors weigh different signals when choosing where to put capital, including changing demand, customer growth and the people behind a business. Michael Lee-Chin says he anticipated his baby boomer cohort shifting from consuming to saving and investing, so he chose wealth management companies over banks and insurers to avoid underwriting losses. Tim Draper says Hotmail spread to 11 million users with an invitation to get free email, and that he backs people dedicated to their work. Tom says the people can be the first sign a business will not work. Serg says many business mistakes come from choosing the wrong people, and describes success as many smart decisions over time.
Start with the interviews
Lessons from Richard C. Wilson's one-on-one interviews, as published on each interview page.
- Michael Lee-Chin: Invest in what people will do next. He saw that his generation would shift from consuming to saving and investing. He chose wealth management companies over banks and insurers to avoid underwriting losses.
- Tom Rosen: Buy when the market is down. Tom bought a lot when the stock market almost collapsed and made a substantial profit. In the year that followed, oil and gas surged. So did some tech.
- Tim Draper: Teach children about money early. Give them a small allowance and have them earn and invest money in the stock market. Over time they learn to ask sharp questions about how a business works.
Videos
- How Connie Looks for Asymmetric Investment Upside: Connie's approach to founder fit, deal terms, team quality and the time private investments may need.
- Direct Investing vs. Fund Managers for Family Offices: See how family offices weigh pooled funds against direct investments and the resources each approach takes.
- How Family Office Leaders Assess Uncertainty and Opportunity: Hear how family office leaders approach uncertainty, support companies, hold cash, and assess opportunities.
- What Family Office Wealth Managers Seek in Investments: Hear how panelists screen managers, tailor advice and think about private market opportunities.
- Richard C. Wilson on Family Office Strategy and Niche Assets: See how Richard C. Wilson thinks about building a portfolio of businesses with strategic roles.
- How a Midwest Family Office Weighs Oil and Emerging Technology: See how one family office weighs investment timing, oil interests and operating businesses across several sectors.
- Top 5 Mistakes in Starting a Family Office: Richard C. Wilson discusses how families can prepare to start a family office and make room for sound decisions.
- The Three Parts of a Family Office Portfolio: A framework for assigning portfolio roles and focusing direct investments where a family has relevant expertise.
- Bitcoin for Family Offices: A Decision Beyond Allocation: See how Eric frames Bitcoin decisions for family offices, from asset categories to ownership choices.
- Direct Investing Contracts and Agreements: A guide to the paperwork investors may encounter when investing directly in a private company.
- Monitoring and Managing a Portfolio of Direct Investments: Learn how Richard C. Wilson approaches monitoring, managing and diversifying direct investments in private companies.
- Tim Draper on Turning Points, Customers and Risk: Tim Draper links Hotmail's growth to customer led sales and describes how early IPOs reshaped his firm.
- George on Structuring Alternative Investments: See how George approaches fractional ownership, structured notes and the design of alternative investments.
- How a Multi-Family Office Approaches Distressed Deals: How Paul's firm evaluates distressed deals, plans for liquidity and sizes positions.
- Angel Investing Strategies for Family Offices: A framework for choosing angel investments, supporting companies and deciding when to invest again.
- How Family Offices Divide Investment Work: See how a family office can decide which investment work to delegate and which to handle internally.
- Highlights from 16 Family Office Trends: Richard C. Wilson maps family office shifts in investment focus, hiring, deal design and technology.
- How Dat Built and Exited a Laser Dentistry Practice: See how Dat weighed an exit, approached deal reviews, and made health part of his plans for freedom.
- How a Chicago Adviser Approaches Family Investment Mandates: A Chicago adviser discusses family portfolios, referrals and the discipline to walk away from a deal.
- Larry Namer on Building E. And Choosing What to Scale: Larry Namer on financing E., programming, evaluating ventures, and reaching new audiences.
- Jose on Opportunity Zones and Private Investment Mandates: Jose explains how his office sources private deals and evaluates opportunity zone, real estate, and fund investments.
- How Saeed Amidi Builds Businesses and Backs Founders: Hear how Saeed evaluates founders and connects startups with corporate partners.
- Michael Lee-Chin on Accountability and Wealth Frameworks: Michael Lee-Chin shares how he thinks about accountability, decision frameworks and changing demand.
- How John Paul DeJoria Built Consumer Brands Through Product Fit and Sales: John Paul DeJoria describes how repeat orders, useful product differences and hands-on partnerships shaped his businesses.
- How Family Offices Weigh Private Company Deals: See how family office investors assess private deals, from risk screening and fees to the manager's investment approach.
- How a Family Office Panel Evaluates Health Tech and Medical Devices: Hear how panelists weigh product use, development stage, exit prospects and their ability to contribute.
- $104M Exit in 3.5 Years: Michael on Capital and AI: A founder explains how he evaluates operators, raises private capital, and sees AI changing established businesses.
Questions answered
- How do wealthy families divide their investments?: Richard C. Wilson says the right balance depends on where a family built its expertise. He describes founders stepping in as chairman or CEO in a niche they kno
- How did Larry Namer manage his money after selling his company?: Advisers managed 90% of Larry's money, and he kept 10% for his own investments.
- How does Richard C. Wilson structure fees for Airbnb investors?: Richard C. Wilson says the Airbnb investment platform charges no acquisition fee or annual management fee. It charges no fee until investors have received all t
- How do family offices divide their investment portfolios?: Richard C. Wilson says families may outsource stocks, bonds, commodities, fund managers and ETFs, choose real estate deal by deal, and keep the most control ove
- Which private assets did Tony Robbins say to pair with public investments?: Tony Robbins tied his asset allocation to Ray Dalio's view that 8 to 12 uncorrelated investments could reduce risk by 80% and increase potential returns. Tony s
- How do investors vet cannabis businesses before investing?: Michael says deal flow is part of diligence itself. Seeing enough opportunities gives his team a basis to distinguish a standout from an average pitch.
- How do family office investors screen new investment ideas and monitor portfolios?: A compelling deck may still fail this panel's screen if the business takes too long to explain or falls outside the office's expertise. Jack's food manufacturin
- How can family offices reduce risk in direct startup investments?: Richard C. Wilson says family offices can invest in stages, check whether a product has a real market and competition, and assess the founders' management exper
- How do professional athletes decide whether to invest in a deal?: Professional athletes in this panel said they assess deals through trusted people, concise pitches, and review by their accountants and attorneys. Brad said he
- How should investors evaluate a biotech opportunity?: Rick compared insulin's historical 58% approval rate from phase one with oncology drugs' 5% rate. That comparison makes the type of therapy part of how he frame
- How do investors manage risk when investing in crypto?: Lawrence's penny stock comparison puts market cap and transparency at the center of how he sorts digital assets. For smaller projects, he points to developer co
- How can investors combine expert views and data when making decisions?: Wilson describes starting with three relevant tools and two deep research reports, then going deeper on one or two. That workflow gives him a way to focus furth
- How can investors explore crypto while managing risk?: Lawrence compared long-tail tokens with penny stocks and NFTs with art, giving listeners familiar reference points for sorting digital assets by risk.