Perceived vs. Actual Risk

What if the biggest barrier to earning returns in alternatives isn’t access, fees, or performance but friction, complexity, and behavior? In this episode, I talk with Brett Hillard, Founder and CEO of GLASFunds, about why infrastructure matters more than selection in alternative investing. Brett explains how GLASFunds helps wealth managers implement alternatives at scale, why K-1 friction keeps investors out of high-return asset classes, and how thoughtful design around vintages, liquidity, and reporting can dramatically improve long-term outcomes. We also explore why “alternatives” is an overused label, how to build portfolios across vintages, and why illiquidity can actually protect investors from themselves.

Highlights:

• Why infrastructure, not product, is the bottleneck in alternatives
• How GLASFunds solved the K-1 problem for multi-fund portfolios
• Why most investors fail simply by not being invested at all
• The behavioral value of minimizing friction and complexity
• Why “alternatives” is a misleading and overused category
• How to build private market exposure across vintages
• Why secondaries and private credit are ideal entry points
• The virtue of illiquidity and why it protects against bad behavior
• Why risk is often misunderstood as discomfort
• How emotional intelligence matters more than technical skill in investing

Guest Bio:

Brett Hillard is the Founder and CEO of GLASFunds, an infrastructure platform that enables wealth managers to build, customize, and implement alternative investment portfolios at scale. GLASFunds provides legal, operational, and reporting infrastructure that allows advisors to offer hedge funds and private capital strategies while dramatically reducing administrative friction, tax complexity, and behavioral barriers for investors. Brett is widely recognized for his first-principles approach to portfolio construction, risk, and behavioral finance in private markets. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Brett Hillard:

LinkedIn:www.linkedin.com/in/brett-hillard-caia-cfa-40729725/

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) Introduction (3:18) Model portfolio for high-net-worth clients and endowment strategies (9:39) Risk tolerance, liquidity, and the misinterpretation of "alternatives" (11:44) Crafting an alternatives portfolio and private credit secondaries insights (18:04) Wealth manager advantages and behavioral investing in alternatives (22:23) Selecting general partners and evaluating hedge funds (24:27) Value creation and risk-reward in private capital and fund vintages (28:32) Investing in first-time funds and assessing risk perception (32:12) Timeless investment advice and the benefits of illiquidity (35:59) Closing remarks