October 06, 2025

E222: Why 90% of Managers Fail Before Fund 3

1 hour 8 minutes

Why do ~90% of first-time managers fail before Fund II/III—and what separates durable fund builders from good investors?

In this episode, I unpack that question with Conrad Shang, Founder & Managing Partner at Ensemble VC. We examine why being a great investor is necessary but not sufficient to be a great fund manager, how to build for durability across cycles, and the partnership practices that earn long-term LP trust. Conrad shares lessons from UTIMCO, Norwest, and Bain Capital Ventures; why sometimes the hardest move is sitting out frothy markets; and how Ensemble uses a team-first lens and internal data products to focus time on the few opportunities that matter. We also discuss defense tech’s shift from “taboo” to mainstream, and why communication cadence and transparency determine who survives the first four to five years—when most managers wash out.

Highlights:

Investor ≠ fund manager: portfolio construction, firm-building, and 10–12 year horizons matter as much as deal picking.

Durability over cycles: sometimes the right move is doing zero deals for ~12 months to avoid overpaying.

Power laws require survival: stay in the game long enough to catch the outliers; size and pacing are part of edge.

LPs as partners, not capital: trust, warm introductions (“trust by proxy”), and over-communication—without “crying wolf.”

Team > solo founder myth: first hires and sequencing reveal how companies will actually be built.

Defense tech arc: from taboo to obvious—examples include ICON (3D-printed homes), Saronic, and Manifest (ex-Palantir).

Data-driven firm design: internal platform (“Unity”) reallocates time from low-yield first meetings to high-conviction winning.

Pilot fund outcomes: Ensemble’s Fund I (pilot) marked ~12×; scaling the model required re-architecting org + software.

Guest Bio:

Conrad Shang is Founder & Managing Partner at Ensemble VC. Previously, he led/managed venture investing at UTIMCO and invested at Norwest Venture Partners and Bain Capital Ventures; earlier he was a consultant at Bain & Company. He’s a Kauffman Fellow and has sat on both the GP and LP sides of the table—experience that informs Ensemble’s product- and data-driven approach to firm building.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

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Stay Connected:

X / Twitter:

David Weisburd: @dweisburd

LinkedIn:

David Weisburd: https://www.linkedin.com/in/dweisburd/

Conrad Shang: https://www.linkedin.com/in/conradshang/

Links

Ensemble VC: https://www.ensemble.vc/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

(0:00) Introduction

(1:25) Fund management skills beyond investing

(2:06) Time horizons in investments vs. fund management

(4:24) Navigating economic cycles and long-term strategy

(7:06) Venture investing and the power law paradox

(8:24) Emerging challenges for new fund managers

(10:48) Investment timing in defense tech and 3D printing

(11:44) Team dynamics and talent as success predictors

(14:57) Trust-building lessons from UTIMCO

(19:04) The critical role of trust in LP-GP dynamics

(21:21) Treating LPs as partners and the educational aspect

(23:50) Mutual benefits of LP-GP collaboration

(29:55) Fostering trusted long-term LP relationships

(33:46) Transparency and communication with LPs

(36:19) Investment theses and relationship importance

(41:58) Insights from LP experience at UTIMCO

(46:41) Practices of successful GPs

(51:58) Relationship alpha and its impact on venture success

(52:32) Ensemble's Fund One and its approach

(54:16) Data and software in Ensemble's investment strategy

(57:06) Data-driven investment case studies

(1:00:37) Ensemble's Unity platform and efficiency tools

(1:03:04) Using data for informed investment decisions

(1:06:06) Team cohesion and its importance

(1:08:14) Closing remarks

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