Uncapped #22 | Greg Rosen from BoxGroup

Uncapped with Jack Altman

Aug 20, 2025•45 min

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Episode description

Greg Rosen is a Partner at BoxGroup. Greg was the first hire at BoxGroup outside of the founders, David Tisch and Adam Rothenberg. After moving to the West Coast to work with Benchmark and Bedrock, Greg rejoined BoxGroup and currently invests out of their San Francisco office. An engineer by training, Greg built iOS games in high school before dropping out of college at 19 to join Jim Pallotta's venture fund in New York City.

BoxGroup is an NYC-based seed stage venture capital firm that has invested in over 500 seed-stage startups over the last 15 years, including Plaid, Ro, Ramp, Clay, Scopely, Warp, Cursor, PillPack, Amplitude, Flatiron Health, Stripe, Warby Parker, Harry’s, Oscar, Flexport, Classpass, Vine, GroupMe, Airtable and more.

We covered:

Being collaborative at scale
Avoiding adverse selection
Getting to a yes instead of no
Venture calendar audits
Running the right strategy

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Timestamps:

(0:00) Intro

(0:47) The collaborative venture model

(5:47) Adverse selection vs coverage

(11:59) How to see a ton of companies

(14:44) Getting to founders early

(21:10) Helping teammates get to a yes

(23:25) Why there aren’t more BoxGroups

(27:57) What’s learnable about picking

(31:46) Calendar auditing

(34:39) Focusing on where you’re outlier

(37:25) Depth vs breadth of network

(41:03) The future of code

(44:00) Brain computers

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