May 14, 2025

12 Years, 12 Lessons: The Unfiltered Playbook for Emerging VCs, with Jonathan Lehr, Co-Founder/GP at Work-Bench

What does it really take to raise and run a venture fund from scratch?

In this special episode of The Drafting Table, Work-Bench co-founders Jessica Lin and Jon Lehr pull back the curtain on their 12-year journey building one of New York’s most respected enterprise seed funds. They share the lessons they wish someone had told them before they ever raised their first fund—and the painful, tactical, and often hilarious moments that shaped Work-Bench along the way.

From getting cold-shouldered by LPs to standing by a tea table just to get a pitch in (yes, that happened), this episode is a no-BS masterclass for emerging managers and anyone dreaming of building a lasting VC franchise.

We cover:

  • What actually moves an LP through the funnel
  • The “slot strategy” that helps create urgency when closing
  • Why your data room is probably too thin
  • What fund management really looks like behind the scenes
  • Why staying disciplined—especially in hype cycles—is your biggest moat
  • How to build in public (and let LPs “lurk”)
  • Why GP-GP references matter more than you think
  • The infamous “tea pitch” and what it taught us about shameless hustle
  • What it means to build a fund, a team, and a franchise for the long haul

📍 Whether you’re raising your first $10M fund or scaling your third, this one’s for you.

Hosted by Jessica Lin (General Partner, Work-Bench)

🎧 Listen wherever you get your podcasts.

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