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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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On this episode, we’re joined by Nate Cooper, Founder & Managing Partner at Barrel Ventures, and OLIPOP pre-seed investor.
He tells the story behind investing in OLIPOP at pre-seed, what changed between the early brand and the rocket ship it became, and the hemp beverage bet he believes is far bigger than most people expect.
Nate unpacks why venture is not a fit for most brands, what founders with no operating background consistently miss, and how to raise around milestones instead of “months of runway.”
We also get Nate’s high-level investment checklist and some advice for breaking into consumer VC.
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Episode Highlights:
🧭 Venture as a tool: when to raise equity vs. when to use debt
🧵 Upstream excitement: ingredients, packaging, and infra that remove friction
🥤 OLIPOP at pre-seed: conviction, category, and the early brand arc
🌿 Why hemp beverages may be a much bigger wave than expected
🧾 Nate’s investment checklist: shelf benchmarking, unit economics, repeat, team
💸 Fundraising that works: milestone-led plans, realistic pricing, exit math
🎯 Careers: how to position yourself for a role in consumer VC
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Table of Contents:
00:51:28 - Intro to Nate and his path into CPG
02:06:05 - Investing in Olipop at pre-seed
05:22:29 - What investors with no operating experience miss
08:17:27 - A tale of two cities when it comes to fundraising (or not)
10:22:27 - Upstream excitement
12:40:27 - Easing friction is the key
14:34:01 - Investing in a product you don’t personally enjoy
15:26:11 - The biggest opportunity in CPG right now
21:04:18 - The bet Nate made in the hemp beverage category
23:54:09 - Nate’s investment checklist
26:36:17 - The early Olipop brand (not great)
27:23:16 - What founders have to get right to have a successful fundraise
29:51:03 - How to land a role in consumer VC
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Links:
Barrel Ventures – https://www.barrelvc.com
Follow Nate on LinkedIn – https://www.linkedin.com/in/nathan-cooper-2ba9aa19/
Follow Adam on LinkedIn - https://www.linkedin.com/in/adam-martin-steinberg/
For help with CPG production design - packaging and label design, product renders, POS assets, retail media assets, quick-turn sales and marketing assets and all the other work that bogs down creative teams - check out KitPrint.
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