How to Bet on the Underdog | Matt Curtolo | Superclusters | S5E6

May 26, 2025

Matt Curtolo, CAIA, a veteran private markets investor, shares his wisdom on teamwork versus star power in venture capital. He discusses the fascinating Rosetto Effect, linking community health to robust social ties. Curtolo reflects on his loyalty to the underdog Detroit Lions, drawing parallels between sports and investing. He emphasizes the critical nature of due diligence in making investment decisions and the value of cultivating workplace culture in remote settings. The conversation wraps up with nostalgic touches and insights into the influence of environment on learning.

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ANECDOTE

Rosetto Effect and Community Health

The town Rosetto, Pennsylvania, had exceptionally low heart disease due to strong community bonds, not diet or genetics.
This sociological phenomenon is known as the Rosetto effect, highlighting social cohesion's power on health.

ANECDOTE

Cheering for the Underdog Lions

Matt Curtolo became a Detroit Lions fan at age seven after watching Barry Sanders' rookie season on VHS.
He cherishes the camaraderie of rooting for an underdog team through many hardships.

INSIGHT

Focus on Team Structure Over Stars

Evaluating investment teams focuses more on how they operate collectively rather than individual star power, especially as firms grow.
Team dynamics and structure become paramount over any single rainmaker’s contribution.

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“The bigger you get, the more established you get, the more underwriting emphasis goes into how this team operates as a structure rather than is there a star?” – Matt Curtolo

Matt Curtolo, CAIA is a seasoned private markets investor and allocator with over two decades of experience at leading financial institutions. Throughout his career, he has been directly responsible for allocating more than $6 billion in commitments to private market investments and maintains relationships with hundreds of general partner relationships across the full spectrum of private capital strategies.

Most recently, as Head of Investments at Allocate, a venture-backed fintech startup. Matt built the investment capability from the ground up, broadening access to top-tier venture capital opportunities for the private wealth market. Prior to this, he served as a senior leader at MetLife, serving on the investment committee, co-managing their global alternatives portfolio and leading the firm's US Buyout portfolio. Earlier in his career, Matt led all private equity activities as Head of Private Equity at Hirtle Callaghan, a large independent outsourced Chief Investment Officer (oCIO). Matt's foundational experience was gained at Hamilton Lane during its early growth phase, before it became the world's preeminent private markets allocator, in research, investment and client-facing roles. Matt currently holds several advisory positions that span start-ups, asset management firms and fund of funds. He also manages his own advice practice, providing GPs with strategic guidance on strategy, fundraising and investor relations.

You can find Matt on his socials here:

LinkedIn: https://www.linkedin.com/in/matt-curtolo-caia/

OUTLINE:

[00:00] Intro[04:24] What town did Matt grow up in?[04:37] Why is that town significant from a sociological perspective?[08:43] Why is Matt fascinated with the Detroit Lions?[11:08] What is it like cheering for the underdog?[13:02] How does Matt break down deal attribution in partnerships?[18:04] GPs' karmic bank account[21:29] What is the kindest thing anyone's done for Matt?[23:24] How did tennis enter Matt's life?[26:35] Historical examples of VC management/leadership structures[29:33] Underwriting track record between senior and junior investors[32:23] How Matt approaches diligence after reading the data room[39:30] How do you know when you've asked enough questions?[42:37] The three classes of questions for GPs that influence investment decisions[45:34] Remote culture[50:16] Cadence of in-person gatherings in remote teams[52:48] The two (and a half) types of conversations to always host in-person[58:37] The last great idea Matt had on a walk[1:02:05] The legacy Matt wants to leave behind[1:04:37] Post-credit scene

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