Playing Venture Like Moneyball

Carson urges managers to focus on getting companies 'on base' and turning singles into 1x outcomes for portfolio health.

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Episode notes

"The limiting downside is actually something a lot of emerging managers don’t think about. If you can turn all of your portfolio companies that don’t hit that exit velocity, if you can find a soft landing for those companies versus that’s a writeoff and they’re dead and done, that’s extra effort, but that’s an extra turn on your fund’s performance." — Carson Monson

Carson Monson is a seasoned allocator with nearly a decade of experience backing emerging and spinout GPs across large institutions, government entities, and family offices. After stints at Greenspring, SITFO, and building a fund of funds strategy for a large European single family office, he now runs the fund of funds at CrossRange, which focuses on supporting top-tier emerging and spinout GPs.

Carson has backed everything from micro funds to high-profile managers spinning out of tier-one firms. He is deeply committed to being a thought partner and strategic resource to the GPs he supports, helping them navigate the complexities of fund building and long-term success in the VC industry.

You can find Carson on his socials here:

LinkedIn: https://www.linkedin.com/in/carson-k-monson/

X / Twitter: https://x.com/Monsson_

OUTLINE:

[00:00] Intro

[02:08] Wildlife and wholesome trouble

[06:03] The journey to being an LP

[10:54] How did Carson join Greenspring?

[13:55] Lessons across Greenspring

[15:46] How many deals did Greenspring do per year?

[18:46] An example of a qualitative metric worth measuring

[20:16] How many off-thesis bets is a VC allowed to make?