E301: Why Generating Alpha is So Hard

After 300 interviews with the world’s top investors, what does alpha actually look like and why is it almost never what people think it is? In this special episode, the roles are reversed. David Weisburd, host of How I Invest and Co-Founder of Weisburd Capital, steps into the guest seat as his co-founder Curtis Pierce takes over as host. Together, they unpack the most important lessons David has learned from more than 300 conversations with CIOs, LPs, GPs, founders, and allocators representing trillions in assets. The discussion centers on why real alpha is hard, boring, and often low-status, how structural advantages drive sustainable outperformance, and why governance and portfolio construction matter more than any single trade.

Highlights:

• Why alpha is almost never a “stroke of genius”
• Hard and boring as the most reliable sources of outperformance
• Prestige as a contra-indicator to future returns
• Structural alpha vs. manager selection
• Portfolio construction as ~90% of long-term outcomes
• Co-investments and fee structure as embedded alpha
• Tax efficiency as one of the most powerful return drivers
• Why lower middle market investing passes the “cocktail cringe test”
• Governance as the true upstream driver of returns
• LP capture vs. LP empowerment
• Why reference calls are the most underrated investing skill
• Career alpha and choosing the right institution
• Focusing on activities that compound over decades

About David Weisburd: David Weisburd is the founder of Weisburd Capital and host of the How I Invest podcast.

He previously served as Partner and Head of Venture Capital at 10X Capital, leading investments in companies including Robinhood, HoneyBook, Palantir, Circle, and DraftKings. He also founded Growth Technology Partners, which was acquired by 10X Capital.

Earlier in his career, David was part of the founding teams of venture-backed startups iSocket (acquired by Rubicon Project) and RoomHunt (acquired by RentLingo). He has served on the boards of three publicly traded companies and holds an MBA from Tuck School of Business at Dartmouth and a master’s degree in psychology from Harvard University.

About Curtis Pierce: Curtis Pierce is a co-founder of Weisburd Capital and the How I Invest podcast.

He previously served as Senior Vice President at 10X Capital, where he led investment and capital markets activities across venture capital and other alternative asset classes. Notably, he led the firm’s investment in Cerebras Systems. He also served as CFO of a publicly-traded portfolio company, successfully executing a change of control transaction.

Pierce began his career at Wells Fargo Securities in the equity capital markets group covering technology, media, and telecom companies. He graduated magna cum laude from the University of Utah with an Honors BS in Finance and currently serves as President of the New York City Chapter of the University of Utah Alumni Association.

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 Curtis Pierce: LinkedIn: https://www.linkedin.com/in/curtisapierce/

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

(0:00) Introduction (1:36) Consistent compounding and portfolio construction (3:33) Achieving alpha through prestige and low status (5:36) Overcoming status games and examples of contrarian investors (9:05) Structural alpha and its examples (12:18) Co-investing and identifying alpha opportunities (16:15) Exploring lower middle market private equity (18:09) Principal-agent dynamics in institutional investing (20:28) Balancing returns and career management for CIOs (22:58) Leveraging corporate governance for institutional capital (25:59) Governance strategies for mid-career allocators (29:23) LP capture: risks and management (32:31) Fostering LP empowerment and avoiding capture (34:51) Evaluating institutional investing practices (36:16) Effective reference calls in investing (38:10) Career advice for recent graduates in finance (39:05) Closing remarks