Operator Selection Over Financial Engineering

What if the best private equity opportunities are the ones no one else is set up to pursue? In this episode, I sit down with Jeff Collins, Founder and Managing Partner of Cloverlay, to explore how he built a $2 billion firm by going where capital isn’t. After 14 years at Morgan Stanley Investment Management, Jeff spun out to focus on what he calls “uncorrelated private assets” - niche, often overlooked segments where return dispersion is wide and operator selection matters more than financial engineering.

Highlights:

• Why “go where the money isn’t” only works if you build the right organization around it
• How Cloverlay built a sourcing flywheel through references and long-term reciprocity
• The importance of holding structured “kill calls” to preserve relationships
• Why broad dispersion of returns signals opportunity in overlooked markets
• How to evaluate niche segments like special mission aircraft, wireless spectrum, and IP
• The strategy behind assembling “portfolio premium” assets in industrial outdoor storage
• Why uncorrelated private assets can act as ballast in institutional portfolios
• How pensions think about completion portfolios and non-beta exposure
• The tradeoff between being an A+ specialist versus a well-rounded investor
• Why Jeff believes ego should be tied to performance, not AUM growth
• The cultural decision to remain focused instead of scaling into adjacent strategies

Guest Bio:

Jeff Collins is the Founder and Managing Partner of Cloverlay, a Philadelphia-based private investment firm managing approximately $2 billion in assets focused on uncorrelated private markets.

Before founding Cloverlay in 2015, Jeff spent 14 years at Morgan Stanley Investment Management, where he led investments across private market strategies and developed a focus on segments with high return dispersion and limited competition.

At Cloverlay, Jeff and his team specialize in niche asset categories ranging from intellectual property and aviation to industrial outdoor storage and other esoteric markets. The firm partners with highly specialized operators and seeks to generate performance through asset selection, structure, and disciplined portfolio construction rather than market beta or leverage.

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 Jeff Collins:

LinkedIn: https://www.linkedin.com/in/jeff-collins-76b7b54/

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) The Strategy: Go Where the Money Isn’t (1:44) Why the Best Opportunities Take 291 Days to Close (3:20) Building Deal Flow Without Bankers or Auctions (7:59) Why Relationships Matter More Than Transactions (11:04) The Power of Proactive Deal Sourcing (14:48) How Small Markets Create Big Returns (19:17) The Role of Uncorrelated Assets in Portfolios (26:39) Why Investors Love Wide Dispersion of Returns (33:38) Turning Gravel Parking Lots Into Institutional Assets (47:27) Why Performance Matters More Than AUM