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🚨 Big news: We’ve raised $160M for @Work_Bench Fund IV to back Seed-stage founders with massive enterprise ambitions.
Enterprise is in our DNA and with Fund IV, we’re quadrupling down.👇
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Jonathan Lehr
27.7K posts
Jonathan Lehr
@fendien
Enterprise VC @Work_Bench | We Lead Seed Rounds with $2-4M Investments | Organizer @NYETM, @KauffmanFellows 19 | My better half is @MichaelaLehr | 305 Native
NYC Katılım Mart 2008
1.4K Takip Edilen6.8K Takipçiler
@lpolovets @Besvinick not monthly anymore (now quarterly) but I've got one that's 12 years old
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@Besvinick These long threads are one of the best parts of the job!
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I do short monthly chats with every seed founder I back. Sometimes they stop after Series A or B, but often they keep going because they're fun.
The longest-running monthly sync -- 9+ years! -- had an exit in June.
Me, hovering over "Delete recurring event" in Google Calendar:
GIF
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Jonathan Lehr retweetledi
Biggest enterprise software acquisitions from 2010-2020
- 3 by Salesforce
- 3 by SAP
- MSFT, Adobe, IBM, Oracle 1 each
- 7/10 acquisitions were between 2018-2020
wonder what this will look like for the 2020s!
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@emilyinvc I'm all about the anticipation of who @FarroYossi wraps next 👀
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my entire linkedin is just:
* fundraising announcements of mega rounds
* ETF advertisements
* yossi farro wrapping tefillin with various VCs
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lol can't disagree here
Sam Altman@sama
i thought this was satire, kept looking for the handle to be spelled c1audeai or something
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Today @vermilionfund closed our $25M second fund.
Still backing technical founders building for technical users in AI infra, security, and dev tools.
95% of my Fund I investors came back for Fund II.
That's the number I'm most proud of.
@DominicMadori from @TechCrunch wrote about our story
techcrunch.com/2026/07/08/sol…
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Jonathan Lehr retweetledi
@bhalligan A big part of what helps fuel the long grind is the laughs along the way, so that's a pity
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Have we lost our sense of humor?
Before every Long Strange Trip episode, I email folks who worked for my guests asking for:
1. Their superpower?
2. Something everyone should know about them.
3. Something funny that happened.
Consistent n/a on #3.
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Poached again! 🤷🏻♀️ I’ve accepted a new role as Editor-at-Large at @BusinessInsider, where I’ll continue covering VC, IPOs etc. I’m also joining Axel Springer’s new program contributing to sister publications including @politico and @Telegraph . businessinsider.com/business-insid…
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It's wild how many AI email bots now use out-of-office replies as prospecting signals.
My @Work_Bench cofounder is on vacation, and her OOO lists me as the backup contact.
Years ago, that just meant she'd come back to a queue of automated follow-ups.
Now it means I'm getting flooded with emails titled:
"Intro via Jess"
"Jess suggested I reach out"
Apparently the newest SDR on the team is the OOO auto-reply.
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wow that's some creative hustle
GEOFF 🧠💸@geoffwoo
i remember this trip. i had a call with scott and zach to invest in the @cognition series A @ $2b while they were en route to visit this kid’s parents. @ScottWu46 is a savage and a winner. hard to compete against or bet against someone who goes this hard
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Jonathan Lehr retweetledi
"Charlie Munger talked about the importance of being multidisciplinary and multidisciplinary thinking. He thinks getting a functional understanding of many disciplines is not that hard. You can just go read the books now or you can talk to your AI about it. I think multidisciplinary thinkers are going to do incredibly well."
Activating Munger Mode for H2 2026. If you are too and you're in NYC, shoot me a DM-- we should grab a coffee.
TBPN@tbpn
.@Collision is bullish on two types of people: high-agency individuals and double majors. "There are two categories of people I would be super bullish on right now and I think will do incredibly well over the next 10-20 years. First, high-agency people. The people at Stripe who have been talking to customers and know exactly what we should do. It's the people who have that pep in their step and want to go make Stripe better. They are so much more empowered thanks to AI." "The second is double majors. I think if you understand software and understand finance, or if you understand software and understand marketing, you now can go massively improve the entire marketing funnel for your company. Now, one person can do what would have taken 20 people dredging through all these systems." "Charlie Munger talked about the importance of being multidisciplinary and multidisciplinary thinking. He thinks getting a functional understanding of many disciplines is not that hard. You can just go read the books now or you can talk to your AI about it. I think multidisciplinary thinkers are going to do incredibly well." From his appearance on the show in April.
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In an era of AI talent wars, founder conviction matters more than founder pedigree.
One of the hottest debates in venture right now is around founder legibility. They're the pedigreed founders that every investor immediately understands and the perspective is that you should back them because they will attract tons of capital and have an advantage in the market from being "king made."
Here's the wrinkle. Some founders may now be too legible. Their backgrounds are so attractive that the biggest risk isn't competition from another startup. It's getting poached by Big Tech and the AI Labs.
Over the last few weeks I spoke with three different Seed investors who had the same story.
All three paid up for exceptionally credentialed founders. Each was in a different sector across agents, AI infra, and security.
The premise was straightforward: expensive at Seed, but potentially massive outcomes.
Then something else happened. The companies started showing promise and the founders got offers they couldn't refuse. These weren't large acquisitions of the companies, but rather talent raids.
Big tech and AI labs increasingly don't want to compete with the best talent. They want to hire it.
The result is a strange dynamic for Seed investors. The founders everyone agrees are exceptional may also be the founders most likely to get pulled off the field before the company reaches escape velocity.
So what do you optimize for? Founders who have a unique world view, are talented enough to build something important, and hungry enough to turn down the comfortable path when it arrives.
That's the hard part of Seed investing today.
Finding founders who are legible enough to believe in, but not so obvious that someone else buys the dream before it becomes a company.
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Its a high conviction environment and you need firepower to compete and win the next Anthropic!... "After betting the firm on Anthropic, Menlo Ventures raises victorious $3B fund" techcrunch.com/2026/06/23/aft… via @techcrunch
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fwiw there is already a graveyard of 2021 vintage VC funds that decided that entry prices didn't matter because they were investing in the biggest opportunities ever
Laurence Allen@laurence1allen
The permanent underclass will be filled with favelas of price sensitive VCs who have passed on SpaceX-sized opportunities
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@briannekimmel over time you develop a Spidey sense to avoid them
that is unless you're @DanielChesley and they jump on you 🤭
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Things I miss after a week in NYC
> gyms open later than 10pm
> cafes with people reading books
> rooftop bars that don’t need heaters
> every store in SoHo
> restaurants with warm lighting
> people who walk fast
Things I don’t miss
> rats that come out of nowhere
> trash day
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