What mistakes have you learned from in venture?

How does an $8B venture platform turn a 650-fund network into a repeatable co-investing edge? In this episode, Jonathan Roosevelt, Managing Director at Industry Ventures, explains how the firm evolved from a pioneer in venture secondaries into a platform combining secondaries, co-investments (directs), fund-of-funds, and tech buyout—with AUM “a little over $8B” and 25+ years in market. We break down why Series A/B/C co-investing requires a different lens than seed, how believability guides which GPs get a “stamp” for later-stage deals, and why customer calls are ground truth when underwriting mid-stage businesses. Jonathan also shares how asymmetric information and inflection points create true co-invest alpha—and when to ignore comps for N-of-1 companies.

Highlights:

• $8B platform: Secondaries, co-invests, fund-of-funds, tech buyout
• 650-fund network: ~250 primaries, ~400 via LP secondaries
• Co-invest engine: 100% sourced from seed/early GP relationships
• Seed vs. mid-stage: PMF stories vs. durable unit economics
• Believability lens: Repeatable process before a later-stage “stamp”
• Ground truth: Independent customer diligence over CEO references
• Asymmetry & inflection: Board insights at turning points drive edge
• Do the unscalable: Sector depth, real customer intros, hands-on help
• N-of-1 underwriting: Backcast valuation from end-state outcomes

Guest Bio:

Jonathan Roosevelt is a Managing Director at Industry Ventures, where he focuses on originating, valuing, and managing primary fund commitments, early secondary LP stakes, and direct company investments within the firm’s Direct & Partnership Holdings strategies. Previously a Venture Partner at Industry Ventures (2017), he was promoted to Managing Director in 2019; earlier, he founded and led companies, was an early employee/VP of Sales at SoFi, and invested as an angel in Fitbit. He holds an MBA and BA from Harvard.

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Links Industry Ventures: https://www.industryventures.com/

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(0:00) Preview (0:04) Customer feedback's impact on investments (1:03) Industry Ventures' co-investment strategy (3:44) Co-investment opportunity lifecycle (7:19) Assessing investment manager credibility and diligence (17:14) Identifying exciting co-investment opportunities (19:47) Triangulating information for investment decisions (23:04) Customer enthusiasm in the investment process (27:16) Relationship significance in investment decisions (29:34) Operator vs investor perspectives in venture capital (34:01) Risk management for seed stage investments (37:10) Competing as an emerging manager in venture capital (38:43) Valuation strategies for new venture capitalists (41:18) Closing remarks