Brandon Sedloff and Aaron Gershenberg sit down in California's wine country to explore three decades of venture capital evolution. Aaron, CEO and managing partner at Pinegrove Venture Partners, shares his unconventional path from economic development work and real estate consulting to building SVB Capital into a $10 billion platform, then relaunching after the bank's collapse as Pinegrove, backed by Sequoia Heritage and Brookfield.
They discuss:
- How Aaron used Monte Carlo analysis to project fund performance and justify additional capital during the dot-com crash
- Why he structured distribution-only fee models for anchor LPs instead of traditional management fees and carry
- The mechanics of becoming a FOIA blocker to attract pension fund capital
- How Pinegrove positions across seed, Series A, Series B, credit, and secondaries to capture alpha at different stages
- Why the 2024–2026 vintage may deliver the fastest value creation Aaron has seen in his career
This episode offers a roadmap for institutional investors navigating venture exposure, LP sentiment shifts, and the structural innovations that have reshaped fund economics over the past 25 years.
Topics:
(00:00:00) - Intro
(00:03:20) - Growing up between Uganda, Kenya and New Jersey
(00:10:50) - Africa's influence and giving back
(00:15:40) - Question authority and the unstructured path
(00:18:30) - Real estate consulting and the sales pivot
(00:21:10) - Breaking into venture in the mid-'90s
(00:32:00) - Joining Silicon Valley Bank
(00:33:30) - Building community through cycling and kiteboarding
(00:37:00) - Launching SVB Capital
(00:40:15) - Innovative fund structures and FOIA blockers
(00:44:20) - Scaling through three eras: 2000–2023
(00:49:00) - SVB's collapse and rebuilding as Pine Grove
(00:50:20) - Partnering with Sequoia Heritage and Brookfield
(00:56:30) - Pine Grove's platform and strategies today
(01:02:30) - AI conviction and the 2024–2026 vintage
(01:09:10) - What keeps you up at night
Links:
Aaron on LinkedIn - https://www.linkedin.com/in/aaron-gershenberg-7361b23/
Pinegrove Venture Partners - https://pinegrove.vc/
Brandon on LinkedIn - https://www.linkedin.com/in/brandonsedloff/
Juniper Square - https://www.junipersquare.com/
