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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
27.6K 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
Meera: I have a welcome gift for you when you’re back from NYC.
Me: What?
Meera: 🚂🚂
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"Bad speed is impatience that pretends to be ambition. It optimizes for novelty over depth and doesn’t let you sit long enough inside the unglamorous stretch where the real edge is formed. Because the truth is that the frontier rarely yields itself in the first six months"
Excellent read from @adityaag
Aditya Agarwal@adityaag
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So many of these companies aren't studied enough
- Prodigy/AOL as early Apps
- We all know PhP/MySQL/Java and JS, but what happened to the others? Nagios, DreamHost, GeoCities
- SurveyMonkey / Salesforce founded in the same year! Webex is also underrated as an early SaaS player
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At long last, got to meet Mr. Data himself @PeterJ_Walker 😎
Fun VC dinner hosted by @cartainc
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Jonathan Lehr retweetledi
What an excellent picture of @fendien and I
Poker, pizza, and beer. Great way to spend a Tuesday night. Thanks to everyone who came and excited for the next one!
Daniel Chesley@DanielChesley
Another Work-Bench poker night in the books ✅ Shoutout to PeerBound, Git AI, and GovWell for making it happen
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Arguably *the* must attend annual event for GPs and LPs alike
@Rick_Zullo and team created and continue to cultivate this thriving community of GPs building firms in thoughtful and different ways to support founders
Read more below and apply to participate
Rick Zullo@Rick_Zullo
1) I’m excited to announce @EqualVentures’s 5th Annual Emerging Manager Circle Summit 8 years ago, this was just a few of us swapping stories, trying to help each other. I couldn’t imagine what EMC would become Now, we need events like EMC more than ever newsletter.equal.vc/p/announcing-t…
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Jonathan Lehr retweetledi
I said this a year ago back when everyone was focused on making more SaaS:
AI is a services game. You cannot solve for enterprise inefficiency with tool adoption. You need AI implementers who go in, understand business processes, refactor for an AI-native reality, and then implement custom agents for those requirements.
Varick has been building in this domain for longer than anyone. 100% of our clients have made it to production, and 100% have come back for project #2.
OpenAI has entered the arena. I'm glad, because there are a million companies in the US alone that need a service like this, and Varick could never help all of them alone.
For companies that don't want to be vendor locked into any one AI company's systems, subjecting themselves to
- price hikes
- model quantization/regressions
- rate limits
- migration costs down the line
Let's chat.
We're also HIRING:
- Engineers
- FDEs
- Consultants
If you're top 1% in your field, I want you at the #1 AI implementation company in the world.
Join Varick Agents, website with careers in the comments
OpenAI@OpenAI
Today we’re launching the OpenAI Deployment Company to help businesses build and deploy AI. It's majority-owned and controlled by OpenAI. It brings together 19 leading investment firms, consultancies, and system integrators to help organizations deploy frontier AI to production for business impact. openai.com/index/openai-l…
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Everyone talks about MCP like it’s magic infrastructure
most MCP implementations today are actually a disaster for enterprise scale.
teams are shoving hundreds of API endpoints into giant MCP servers and blowing up context windows + token costs.
one company told me their platform has 500+ endpoints. raw API-to-MCP conversion would completely break the agent experience.
the future is not: “here are 500 actions an LLM can take”
the future is: “here’s the exact outcome you wanted in one call”
that’s a very different product design mindset than SaaS APIs were built for.
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"The risk is not that AI does the work. The risk is that AI does the work and we never learn from it."
tobi lutke@tobi
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@buccocapital @GergelyOrosz We've always been focused on helping our enterprise startup port co's build and scale their GTM motions at @Work_Bench, and exactly to your point @GergelyOrosz we tripled down on this critical need in an AI-first world
linkedin.com/posts/jlehr1_a…
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Starting to REALLY see how reaching potential customers is becoming a massive pain point for software startups - esp w AI!
I get so much more messages about software that founders built rapidly that they think will solve some important problem (usually eg AI+context/trust/security).
But how will anyone know about it?
It was fast to build, but getting the world to know about it / care about it is increasingly hard/expensive/time-consuming.
And the irony is: the "easier" it is to build, the more the only differentiation is marketing/advertising! (Because the easier it is to build, the more teams build something similar in parallel, and racing to win the market becomes key!)
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Jonathan Lehr retweetledi
Hosting another NYC Tech Poker Night on May 12th at a cool venue in NYC
My previous event had founders & engineers from Anthropic, Ramp, Traversal, Datadog, Palantir, and more
Come hang!
luma.com/pokerwb
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My grandfather, Ike Sleeper, passed away yesterday.
A son of refugees, he lived the American Dream. He worked in our family’s grocery store into his 80s, was married for 60 years and loved his family fiercely.
Some of the lessons I learned from him:
1) He brought an intense, earnest fastidiousness to everything he did in life. His yard was weedless, the store’s shelves were fronted (compulsively), his garage floor was painted annually, etc. He believed passionately in doing everything with pride, no matter how small.
2) He was an investor and a big believer in America (and these were closely intertwined). The idea of owning part of a great American company had special meaning for him- he bought me my first shares of stock (Cisco at the height of the dotcom bubble and Disney) and made sure I understood what those pieces of paper meant.
3) He loathed idleness but believed in/loved to travel and explore. Time didn’t need to be work to be well spent, and he was always up for an adventure. I’m grateful that I managed to take one with him (a river cruise in Europe) and can’t recommend those sorts of trips enough- take your grandparents on one on one trips! It’s amazing.
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Great comment by @Steve_Rosenbush in @WSJ CIO Journal this morning
AI penetration in the enterprise is ultimately limited by people and change management, especially as we move beyond coding agents to other front office use cases
That's why customer empathy matters so much
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"You are buying optionality on a founder and a thesis before the market has formed a view and being properly compensated for that risk. The price is low not because the company is bad or because the founder lacks ambition. The price is low because the proof points are few and the risk is real. That is precisely why the return potential is asymmetric."
Excellent writeup by @Besvinick on pre-consensus founders. Totally agree with his POV 🎯
Adam Besvinick@Besvinick
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@MeghanKReynolds @KimKBent @megankreynolds how are LPs evaluating bubble pricing and AI disruption concerns across GPs? I'm curious especially for large markups from the ZIRP period where growth may have stalled significantly and there have been limited markdowns?
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Heard from LPs this week: more than a bit of fatigue What’s driving it?
- Constant fundraising by GPs in their portfolio, but little liquidity
- Portftolios that seem promising, but deep concern about disruption and / or bubble pricing 🫧
- Constant headlines on the model companies - on financials, on capital raising and innovation - hard to keep up
- The “how concentrated should I be in these same companies” question
- The “how worried should I be about all of the PE software in my book” dynamic
- Huge dispersion in public markets
- It’s annual meeting season so they are traveling nonstop
- Oh yeah, and there’s a war on top of it…
Hug an LP today! 🙏
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I really enjoy @levie's takes on all things AI and agents because he's such a consistently clear and prescient thinker
For anyone old enough to remember, he had an epic run of writing that helped promote enterprise software startups in the early 2010s
techcrunch.com/2010/07/25/ent…
Now if only I could find the meme of Steve Ballmer he made for BoxWorks 2011...
Aaron Levie@levie
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What a blast I had talking to Owen Davis' class at Columbia Business School!
I had the opportunity to share the @Work_Bench origin story, dig into what actually changes (and what stays the same) in today's AI environment, nerd out on enterprise trends that excite us now, and answer thoughtful questions like which incumbent SaaS companies own sticky enough workflows that AI-first startups may not be able to eat their lunch.
One lesson learned though…next time I take a selfie, it's better to give the class a heads up 😅 otherwise it looks like I just gave a 60-minute lecture on pain.
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"there are many, many profit pools that depend on apathy/laziness and a poorly informed customer - the industry that brought you the efficient market depends on an inefficient consumer to eat"
this is a spot on take from @illscience
Anish Acharya@illscience
profitable apathy if you thought saas-pocalypse was bad wait until computer use comes for consumer financial services and vampire squids the whole thing there are many, many profit pools that depend on apathy/laziness and a poorly informed customer - the industry that brought you the efficient market depends on an inefficient consumer to eat first the models will systematically exploit every customer subsidy (transfer bonuses / teaser rates), move deposits to maximize yield, open and close accounts on a whim - this industry has operated with asymmetric bureaucratic warfare through paperwork and sheer friction and the models will cut through this like a hot knife through butter and the model will neatly route around late fees, interest charges, overdrafts, expiration of teaser rates, and any mispriced debt that can be refinanced in the market - literally just moving people out of expensive debt and into cheap debt (that they are already approved for!) would save many american families thousands per year meanwhile vps and managers at these companies will hold on to their shrinking revenue lines the same way that executives at carriers protected SMS revenue as it collapsed to zero - they have zero chance of sticking the landing on new technology - and the smart ones will likely go for extending regulatory capture into the agentic economy so much of the consumer financial services ecosystem is marketing via subsidies on one end and profit maximization via customer apathy on the other, and it will collapse under its own weight as the agents pick it apart ironically the industry response to plaid was a misguided attempt to protect this very "profitable apathy" by disallowing APIs and in the end it will be agents that kill them clicking around their own UI, not the fintech aggregators they so greatly feared the end state of this is likely a headless auction where every time you swipe your credit card, some lender bids on taking the risk and capturing the profit from that transaction - it will be a much more efficient system that will work much better for consumers, and many pockets of financial services are going to see contraction as a result aa + 5.5
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@JaredSleeper As a Blackjack lover this post is *sooo* spot on
If you're at AWS Reinvent later this year we need to play together!
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Blackjack is my favorite casino game.
It is common to pick poker, but I think there are actually many insights into psychology (and yes, investing!) hidden in Blackjack.
A few reflections:
1) Even with knowable rules and complete information, people still can't help themselves from making basic errors if it "feels" stupid (i.e. they'll stand on 16 vs. a ten up, etc.). I see this same behavior all the time in investing- folks "know" they're doing something wrong, but some psychological pressure overrides their intellect at decision-time.
2) You can really get a feel for whether someone loves momentum or not quite quickly. Some players win and reflexively increase their bets- others get more cautious, expecting mean reversion. Neither is rational, but these are often deeply entrenched patterns of thought.
3) In general, anytime someone deviates from the book (assuming they know the rule in question) there's something completely fascinating going on.
4) People inexorably give each other credit and blame themselves for outcomes that everyone knows are random. You'll high-five and celebrate, tell other players good job, thank someone for pulling a card that would bust you, etc. Ideally, the celebration SHOULD be for people who overwhelm their psychology and play correctly, but that gets lost- if anything, people celebrate the deviations that pay off more because they seem "brave".
Overall, I think investing is way more similar to blackjack than people want to think. You need to carefully divorce process from outcomes, celebrate good process, accept the variance that comes with the randomness of the world, and ruthlessly try to avoid psychological biases... and those similarities (+ the joy of winning/losing together with friends, of course) are what make an otherwise boring game fun. :)
Jared Sleeper@JaredSleeper
On a flight to Vegas and built a working blackjack training app in about five minutes... yes, the world has changed.
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