Jon Lehr, is co-founder of Work-Bench VC, a seed series fund focused on Enterprise. He’s also a smart guy, a good dude, and my friend.
How are enterprises using AI now, and how are techcos building for them, and what’s an investor to do?
Jon knows.
Jon dishes on rethinking enterprise VC by starting with the enterprises themselves, navigating real sales cycles, and backing atypical founders. Part of it is doing the hard things well: defining ICPs, resisting bad partnerships, and competing with megafunds without playing their game. But there’s also a decent amount of learning from mistakes, and as per always, adapting to the new-normal.
Prior to Work-Bench, Jon worked at Morgan Stanley in the Office of the CIO in IT. There he partnered with internal technology clients to facilitate the selection and on-boarding of emerging technology startups. He has written about enterprise technology trends for publications such as The Wall Street Journal's CIO Journal and TechCrunch.
Jon is a graduate of the University of Pennsylvania where he received a BSE in Bioengineering with minors in Mathematics and Economics.
Show notes below
Catch up on everything you missed
The best way to catch up on everything you missed is to skim the archive
There’s a lot of goodies. You don’t want to miss ‘em.
What do Enterprises want with their AI? What if you don’t have AI to offer?
00:00 Opening Moves: A look inside Workbench and the thinking behind its new fund
01:23 Inverting the Model: Rethinking enterprise VC by defying Silicon Valley orthodoxy
04:17 ICP Isn’t Obvious: Why ideal customer profiles in enterprise are harder than they look
06:31 The Bear Hug Trap: How to survive the enterprise partner that smothers you
10:23 Enterprise Sales, Decoded: Mapping the real journey from intro to closed deal
12:22 Seed to A, Now: What it really takes to raise an A in today’s enterprise market
14:55 What Buyers Want: How enterprise tech priorities have shifted post-2021
18:04 Off-Track Founders, On-Point Ideas: Avoiding the megafund stampede by sourcing differently
🚨🚨Claymation Clip Interlude🚨🚨
20:26 Flawed Theses & Common Pitfalls: The worst assumptions in enterprise investing
21:58 Beyond AI: Building meaningful startups around non-obvious, non-AI problems
24:24 The Toughest Competitor: The one public company no startup wants to face
26:17 The Rise of Zombie-corns: Why capital-rich, growth-poor startups are more dangerous than they appear
30:08 The ZIRP Hangover: Cleaning up the distortions left by a decade of free money
35:44 Complacency Will Kill You: Why sleepy incumbents can’t survive what’s coming
38:31 Raising a Fund in 2025: What’s changed, what hasn’t, and what LPs want
41:59 Competing with Giants: Tactics for staying scrappy when megafunds move in
45:24 A High-Stakes Landscape: Why this is both the best and hardest time to invest
46:39 Idea Flow as Edge: How cross-pollination unlocks investor insight and creativity
Also available on Youtube
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