Judgment Transfer from Fighter Pilots

What separates enduring investment firms from those that quietly break as they scale? In this episode, I talk with Chris Brimsek, Managing Partner of CAB Advisory, about the unseen mechanics behind building durable alternative investment firms. Drawing from his experience as Chief of Staff to David Rubenstein and former COO of Carlyle’s $15B Infrastructure & Energy business, Chris explains why culture, judgment transfer, and succession—not deal mechanics—are the true bottlenecks to long-term performance. We unpack how elite leaders create environments without intellectual hierarchy, why forgiveness builds trust faster than perfection, and how emerging managers can avoid the most common traps as they scale.

Highlights:

• Why the best firms eliminate intellectual hierarchy, not decision hierarchy
• How great leaders use mistakes to build confidence and trust
• “Expect what you inspect”: using questions to shape culture
• Why most GPs underestimate the challenge of running a business, not a fund
• The difference between managing deals and building a firm
• Succession as knowledge and judgment transfer—not titles or economics
• Lessons from fighter pilot debriefs applied to investment decision-making
• Why non-economic factors dominate talent retention
• How GP stakes are reshaping incentives and firm-building
• The biggest silent risk facing emerging managers today

Guest Bio:

Chris Brimsek is the Managing Partner of CAB Advisory, where he serves as a trusted advisor to founders and leadership teams of alternative investment managers. Previously, he was Chief Operating Officer of The Carlyle Group’s Infrastructure & Energy business and a member of Carlyle’s Global Private Equity Operations team. Chris began his career as Chief of Staff to Carlyle Co-Founder David Rubenstein and was part of the executive group during Carlyle’s IPO. He holds an MBA from Harvard Business School and a bachelor’s degree from Washington & Lee University.

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.

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 Chris Brimsek :

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

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 (1:15) Intellectual curiosity and leadership at Carlyle (4:51) Best practices for engaging junior personnel and creating a culture of open communication (8:51) The role of incentives in retaining talent and differences between banking and asset management (13:02) Challenges and strategies for emerging managers in investment firms (18:52) Trends in alternatives and basics for LPs evaluating managers (20:29) Intentionality, innovation, and succession in investment firms (24:23) Challenges in launching new products and managing distraction costs (28:00) Importance of honest communication and common problems GPs hide from LPs (34:51) Role and impact of GP stakes in the market (38:00) Addressing LP skepticism and misconceptions about GP stakes (41:39) Industry changes and timeless career advice (45:26) Strategic thinking and the value of intellectual curiosity in career development (47:41) Closing remarks