Is the real edge in investing not picking assets but structuring how you allocate capital? Terence Thompson is a Vice President of Investments at DF Enterprises, about how single family offices think about portfolio construction, liquidity, and structural alpha. We break down why Terry uses a total portfolio approach, how family offices create edge through flexibility, and why being a liquidity provider during market stress is one of the most powerful strategies. We also discuss concentration risk in public markets, the evolution of private markets, and how allocators can think about illiquidity, secondaries, and niche opportunities.

Highlights:

Why single family offices have a structural edge over multifamily offices
Total portfolio approach vs traditional asset allocation
Competing strategies for capital across the portfolio
Why liquidity is critical during market dislocations
Concentration risk in large cap equities
Structural changes in small cap and private markets
The impact of retail capital flowing into private equity
How misaligned liquidity structures can hurt returns
Where illiquidity premium still exists
Underrated opportunities in small buyout and niche credit
The role of behavioral bias in asset allocation
Why risk tolerance should match the capital base

Guest Bio:

Terence Thompson is a Vice President of Investments at DF Enterprises, a single family office where he oversees investment strategy, portfolio construction, and manager selection across public and private markets. He has over a decade of institutional investment experience, including managing assets at Blue Cross Blue Shield of Arizona. Terry is a CFA charterholder, USAF veteran, and an active member of several investment and policy organizations. He focuses on building resilient portfolios that balance liquidity, risk, and long-term compounding.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Terence Thompson:

LinkedIn:https://www.linkedin.com/in/terencemthompson/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) What Gets Lost When a Family Office Serves Too Many Families (2:00) Why the Traditional Endowment Model Isn’t Flexible Enough Anymore (2:45) The Hidden Force Behind Today’s Momentum Trades (6:29) Why Passive Investing May Be Riskier Than It Looks (13:28) Why Retail Capital Will Change Private Markets in a Big Way (16:31) The Structural Flaw That Could Hurt Retail Investors (19:29) Is the Illiquidity Premium Still Real? (21:18) Why Small Buyout May Benefit Most From the Retail Wave (23:41) The Most Underrated Asset Classes Right Now (30:24) The Career Advice That Matters More Than Playing It Safe

E350: How Family Offices Quietly Build Generational Wealth