Founder @DealStreetAsia (Nikkei Group). Journalist-entrepreneur.
@himangi_t's partner, blessed to be a father of two.
jojiphilip at dealstreetasia dot com
The Three Humans Left in a VC Firm
Fred Wilson, co-founder, Union Square Ventures, interviewed by Michael Mignano (USV)
[I post one executive summary daily of an interview I enjoyed and learnt from. I loved this interview that @mignano did with @fredwilson, who I've learnt a tremendous amount from on the board of Coinbase. Tons of great nuggets for founders and investors.]
Summary: After 40 years in venture, Wilson has rebuilt USV around a single conviction. Only three things in the firm still need a human: picking the thesis, building relationships with founders working in that thesis, and supporting them after the check. Everything else, including sourcing, diligence, term sheets, and CRM, is being handed to agents. The interview is a working sketch of what a venture firm looks like when the back half of its job becomes software, and a clear read on what stays human-only and why.
1. The Three Humans Left. A year ago Wilson wrote a memo to his partners saying that if he were starting USV from scratch today, only three jobs would stay with humans: high-level thesis development, building relationships with founders inside that thesis, and supporting them after the check. Everything else gets handed to agents. USV is now executing on that memo, not theorizing about it. For founders raising, this is the new operating profile of the firm sitting across the table.
2. Agents Love Data Rooms. "I hate data rooms. Agents love data rooms." USV no longer asks a junior associate to scrub the data room before a term sheet. An agent reads the room and answers questions in conversation: cap table, vesting, founder ownership, anything in the corpus. The effect on partner time is direct, with less work on the parts of the job no one enjoys and more time with founders.
3. Term Sheets Without Lawyers. USV's term sheets are now written by an agent, with no outside counsel stamp at the term-sheet stage. The firm seeded the agent with standard term sheets by sector and by stage, then partners shape each document in conversation with the agent. Wilson does not yet trust an agent to write long-form definitive docs. The implication for founders: term sheets land faster, with less round-trip friction, and the cost structure of the next-generation venture firm starts to drop.
4. The Kill Zone Test. Wilson ran a sample contract through a legal-AI startup and through raw Claude Code, side by side, and Claude's markup was better. "All of legal AI is in the kill zone." The test is portable to almost any AI vendor pitch. If a wrapper company cannot outperform the raw model on the thing it sells, the wrapper is paying for the privilege of being disrupted. Operators should run the same test before signing a multi-year contract.
5. No Wrappers Allowed. To survive the kill zone you cannot wrap a model. You have to rebuild the business model from scratch around the new economics. Cursor is the example Wilson reaches for: it has been hugely successful, but more developers are dropping back to raw Claude Code, and nothing stops Anthropic from shipping an IDE. A defensible AI company redesigns the workflow itself, so the foundation lab would have to abandon its current pricing model to copy.
6. Energy Is the AI Trade. About a third of USV's deployment now goes to energy, because no matter which model wins, the winner needs power. The firm has backed a decentralized model-training network and a company that turns each grid-scale solar and wind plant into a mini data center selling inference tokens. The trade is indexed to AI without forcing USV to pick the model. Builders hunting for a less crowded adjacent market should read the same memo, because the picks and shovels of AI run through electricity.
7. Sellers, Not Coders. The skill USV now overweights in founders is selling: recruiting, fundraising, convincing customers, inspiring teams. Forty years has taught Wilson that the founder who can tell the story and bring it to life wins more often than the founder who can write the code. The corollary is uncomfortable for technical founders. "Actually being able to write code is probably not a big deal anymore," though enough technical vision to see three moves ahead still matters. If you are a CEO who cannot recruit, that is now your constraint.
8. The 80–90% Open Source Window. Open-source models, especially the ones shipping out of Asia, are running at 80 to 90 percent of the quality of the closed frontier models. Right now the closed labs are subsidizing usage, so price does not force the comparison. When the labs have to charge a real margin, open source becomes a serious value alternative and the playing field levels. Wilson is not betting the firm on this outcome, but he is hedging into the quadrant where open source wins.
9. Founders Still Want Humans. Founders do not want to raise money from an agent. They want to know the human they are getting in business with, and that is why Wilson does not see VC automating itself out of a job in the short term. The firm can automate the back half of the workflow. The front half, sitting across from a founder at 11 p.m. when they have had a horrible day, stays human.
10. Don't Pass on Price. The biggest regrets of Wilson's career are deals he passed on because the price was too high. The market-clearing valuation will almost always feel uncomfortable a year later, and the right answer is to find a way in, even if that means buying secondary instead of leading the round. Saying no on price is a defensive move masquerading as discipline. Founders raising can use the line in negotiation, because a firm that walks on price is telling you it has not adjusted to the current market.
11. Offense Over Defense. Wilson lost $25 million in six months in 2001 and learned that getting it wrong is a byproduct of the job, not a verdict on the investor. He spent his first 15 years scared of losing money and only got good at venture once he stopped playing defense. The advice is harder to apply for someone breaking in, because the first checks really do matter, but the directive holds at every level. For operators, the analog is the founder who refuses to ship until the product is perfect, because you cannot win a game you are not playing.
12. The Relationship Is the Moat. After 40 years and an AI rebuild of the firm, Wilson's one-line summary of the venture business is the same as it was on day one. The relationship between the investor and the founder is the secret sauce. Everything else, including the work USV used to staff up to do, gets compressed by technology. Find great founders, build real relationships with them, and help them build great companies. If your venture pitch to LPs does not lead with that, you are pitching the wrong business.
A compendium of Pilot Rules (Number 30 is Gospel in Fighters).
1. The only three things a wingman should ever say are:
“Two's up. “
“Lead, you're on fire.”
“I'll take the fat chick.”
2. In a multi-place aircraft, there are only three things the copilot should ever say:
“Nice landing, Sir.”
“I'll buy the first round.”
“I'll take the fat chick.”
3. As a new copilot on a bomber I was told to say these three things and to otherwise keep my mouth shut and not touch anything:
“Clear on the right.”
“Outer (marker) on the double (indicator).”
“I'll eat the chicken.” (Crew meals consisted of one steak and one chicken to avoid possible food poisoning of the cockpit crew).
4. As an aviator in flight you can do anything you want. As long as it's right. And we'll let you know if it's right after you land.
5. You can't fly forever without getting killed.
6. As a pilot only two bad things can happen to you and one of them will:
One day you will walk out to the aircraft knowing that it is your last flight in an airplane.
One day you will walk out to the airplane not knowing that it is your last flight in an airplane.
7. Any flight over water in a single engine airplane will absolutely guarantee abnormal engine noises and vibrations.
8. There are Rules and there are Laws. The rules are made by men who think that they know better how to fly your airplane than you; the Laws (of Physics) were made by God. You can, and sometimes should, suspend the Rules but you can never suspend the Laws.
9. More about Rules:
The rules are a good place to hide if you don't have a better idea and the talent to execute it.
If you deviate from a rule, it must be a flawless performance. (e.g., If you fly under a bridge, don't hit the bridge.)
10. The pilot is the highest form of life on earth.
11. The ideal pilot is the perfect blend of discipline and aggressiveness.
12. About check rides:
The only real objective of a check ride is to complete it and get the bastard out of your airplane.
It has never occurred to any flight examiner that the examinee couldn't care less what the examiner's opinion of his flying ability really is.
13. The medical profession is the natural enemy of the aviation profession.
14. The job of the Wing Commander is to worry incessantly that his career depends solely on the abilities of his aviators to fly their airplanes without mishap and that their only minuscule contribution to the effort is to bet their lives on it.
15. Ever notice that the only experts who decree that the “age of the manned flight” is over are people who have never flown anything? Also, in spite of the intensity of their feelings that the pilot's day is over I know of no such expert who has volunteered to be a passenger in a non-piloted aircraft.
16. It is absolutely imperative that the pilot be unpredictable. Rebelliousness is very predictable. In the end, conforming almost all the time is the best way to be unpredictable.
17. He who demands everything that his aircraft can give him is a pilot; he that demands one iota more is a fool.
18. If you're gonna fly low, do not fly slow! ASW pilots know this only too well. (Amen)
19. It is solely the pilot's responsibility to never let any other thing touch his aircraft.
20. If you can learn how to fly as a 2nd Lt and not forget how to fly by the time you're a Maj. you will have lived a happy life.
21. About night flying:
- Remember that the airplane doesn't know that it's dark.
- On a clear, moonless night, never fly between the tanker's lights.
- There are certain aircraft sounds that can only be heard at night.
- If you're going to night fly, it might as well be in the weather so you can double count your exposure to both hazards.
- Night formation is really an endless series of near misses in equilibrium with each other.
- You would have to pay a lot of money at a lot of amusement parks and perhaps add a few drugs, to get the same blend of psychedelic sensations as a single-engine night flight in weather.
22. One of the most important skills that a pilot must develop is the skill to ignore those things that were designed by non-pilots to get the pilot's attention.
23. At the end of the day, the controllers, ops supervisors, maintenance guys, weather guessers, and birds are all trying to kill you and your job is to not let them.
24. The concept of "controlling" airspace with radar is just a form of FAA sarcasm directed at pilots to see if they're gullible enough to swallow it. Or to put it another way, when's the last time the FAA ever shot anyone down?
25. Remember that the radio is only an electronic suggestion box for the pilot. Sometimes the only way to clear up a problem is to turn it off.
26. It is a tacit, yet profound admission of the preeminence of flying in the hierarchy of the human spirit, that those who seek to control aviators via threats always threaten to take one's wings and not one's life.
27. Remember when flying low and inverted that the rudder still works the same old way but hopefully your flight instructor never taught you "pull stick back, plane go up".
28. Mastering the prohibited maneuvers in the NATOPS Manual is one of the best forms of aviation life insurance you can get.
29. A tactic done twice is a procedure (refer to unpredictability discussion above).
30. The aircraft G-limits are only there in case there is another flight by that particular airplane. If subsequent flights do not appear likely, there are no G-limits.
31. One of the beautiful things about a single piloted aircraft is the quality of the social experience.
32. If a mother has the slightest suspicion that her infant might grow up to be a pilot, she had better teach him to put things back where he got them.
33. The ultimate responsibility of the pilot is to fulfill the dreams of the countless millions of earthbound ancestors who could only stare skyward ...and wish.
My name is Ram.
You called me by a Muslim name because I called Narendra Modi a fraud, a weak leader.
You calling me Abdool will not make me less Hindu.
Nor do I feel insulted.
All I see is a low-IQ insecure bhakt who fears that every Hindu will understand the truth about Narendra Modi the way I do today. Cope.
Three punches in a row.
First, GST on online gaming jumped to 28% on deposits. Dream11 took the hit and rebuilt the business.
Then the government banned real-money gaming. They took the hit again and pivoted to sports and stocks.
Today, the courts upheld retrospective GST — paying tax on years of past operations under rules that didn't exist at the time.
No company survives a third punch like that. It will wipe out the whole industry.
@harshjain85 and the @Dream11 team built something super special. They complied with every rule, always looked after their users, absorbed every increase, and never asked for sympathy. Just kept building.
What got upheld today doesn't punish bad actors. It punishes builders.
The silence on Twitter is the most depressing part of all this. I really hope the government reconsiders — there is still a way to save this industry and the people who built it.
Today we reduced headcount by 22%. The business is the strongest it's ever been. So I think it's important to be direct about what I'm seeing and why.
First, I made this decision and I own it. I did it because the way to operate at the highest level of productivity is changing, and to win the future, ClickUp needs to change with it.
Second, this wasn't about cutting costs. Most savings from this change will flow directly back into the people who stay. We'll be introducing million-dollar salary bands. If you create outsized impact using AI, you'll be paid outside of traditional bands.
Most importantly, I have the deepest gratitude for those affected. We're doing this from a position of strength specifically so we can take care of people properly. Everyone affected receives a package aimed at honoring their contributions and easing the transition.
I only see two options: wait for this to play out gradually in the market or be honest about what I'm seeing and act proactively.
THE 100X ORGANIZATION
The primary change is that we're restructuring around what I call 100x org. The goal is 100x output. The roles required to build at the highest level are fundamentally different than they were a year ago.
Incremental improvements to existing systems won't get us there. We need new ones. That means creating enough disruption to rebuild rather than iterate on what's already broken.
The common narrative is that AI makes everyone more productive. It doesn't. Many of the workflows of today, if left unchanged, create bottlenecks in AI systems.
These roles will evolve. But waiting for that to happen naturally means falling behind now.
The 100x org is actually heavily dependent on people - infinitely more than today. This is only possible with 10x people that have embraced and adopted new ways of working.
THE BUILDERS, AGENT MANAGERS, AND FRONT-LINERS
— THE BUILDERS: 10X ENGINEERS
I don't think most companies have internalized what's actually happening with AI in engineering. The common narrative is that AI makes all engineers more productive. That may be true in isolation, but at an organization level - that is the farthest thing from reality.
Here's what we've validated recently at ClickUp: the great engineers, the ones who can orchestrate, architect, and review, are becoming 100x engineers. They're not writing code. They're directing agents that write code. The skill is judgment.
AI makes the best engineers wildly more productive, and everyone else using AI slows these engineers down.
Think about it - the bottlenecks are (1) orchestration - telling AI what to do, and (2) reviewing - what AI did. Everything is leapfrogged and no longer needed.
So who do you want orchestrating and reviewing code?
And how do you want your best engineers to spend their time?
If your best engineers are spending time reviewing other people's code, then this is inherently an inefficient bottleneck. These engineers can review their agent's code much faster than reviewing human code.
The new world is about enabling your 10x engineers to become 100x.
The wrong strategy is to push every engineer to use infinite tokens. Companies doing this are celebrating 500% more pull requests. But customer outcomes don't match the volume of code being generated.
I call this the great reckoning of AI coding, and every company will face this soon if not already.
More code is just another bottleneck to the best engineers, and ultimately to your company's impact as well.
— THE BUILDERS: 10X PRODUCT MANAGERS
Product management and design roles are merging.
Designers that have customer focus, become more like product managers.
And product managers that have intuition for UX become more like designers.
The bottleneck of user research is gone. It takes us just one mention of an agent to kickoff research and analyze results.
The bottleneck of product <> design iteration is also gone. The product builder iterates on their own, along with agents and skills that ensure alignment with quality and strategy.
Also controversial today - I believe that the wrong strategy is to have your PMs shipping code - that just introduces another bottleneck that the best engineers will waste their time on.
To be clear, PMs should be coding but they should do this in a playground to iterate, validate, and scope. That code should not go to production.
Everything outside of managing systems, orchestrating AI, and reviewing output becomes a bottleneck.
That's why the other roles that are critical along with these are the systems managers (to reduce bottlenecks) along with a bottleneck you can't replace - customer meeting time.
— THE SYSTEM MANAGERS
Ironically, the people that automate their jobs with AI will always have a job. They become owners of the AI systems - agent managers. We have many examples of these people at ClickUp.
The underlying systems in which we operate are absolutely critical to get right. I think most companies are delusional to think they can iterate on existing systems and compete in this new world.
You must create enough disruption so that old systems are deprecated entirely. If there's any definition for 'AI native' that's what it is.
— THE FRONT-LINERS
In a world that will become saturated with AI communication, the human touch will matter more than anything to customers.
This is a bottleneck that you shouldn't replace - even when agents are high enough quality to do video meetings.
One-on-one meeting time with customers is something that shouldn't be automated. The systems around the meetings should be - so that front-liners spend nearly 100% of their time with customers.
REWARDING 100X IMPACT
In a world where companies are able to do so much more with less, where does that excess money go?
In our case, much of the savings in this new operating model will flow directly back to those that enabled it.
We must reward people that create productivity accordingly. This aligns incentives on both sides. Plus, in a world where your best people create 100x impact, you can't afford to lose them.
You should aim to retain these employees for decades. The context they have and their ability to efficiently orchestrate and review will be nearly impossible to replace.
Compensation bands of today should be thrown out the door. We're introducing $1 million cash/year salary bands with a path available to nearly everyone in the company if they produce 100x impact by creating or managing AI systems.
THE FUTURE
Nearly every company will make changes like these. The ones that do it proactively will define what comes next.
The future is not fewer people. It's different work, new roles, and better rewards for those who embrace it. We're already seeing entirely new roles emerge, like Agent Managers, that didn't exist a year ago.
ClickUp is positioning to lead this shift, not just internally, but for our customers too. I've never been more certain about where we're headed.
After four years full of challenges and hard work, it's time to move on.
I leave with the feeling that the mission is complete. 4 seasons, 3 championships.
I will never forget the love I received from the fans from my very first days.
Catalonia is my place on earth.
Thank you to everyone I met along the way during these beautiful four years.
A special thank you to President Laporta for giving me the chance to live the most incredible chapter of my career.
Barça is back where it belongs.
Visca el Barça. Visca Catalunya 💙❤️
@fcbarcelona
My billionaire client once told me: I don't hire for salary. I hire for sleep.
Because a bad hire means I’m up at 2 am fixing what they broke, especially when that damage touches a client relationship built over years.
His words just stayed with me forever
Five years into running an agency across India and the UAE, the most expensive mistake I made was a low-paid inexperienced hire that indirectly cost us a ₹2 lakh per month client.
In markets like GCC, where reputation travels faster than promotion, that shift can cost you more than you think.
When someone joins my team, I am handing them access to relationships built over years, strategy calls, and consistent delivery.
And the impact of the wrong person rarely appears through small lapses in judgment, tone, and preparation & clients notice patterns before they raise a concern.
So today, I view hiring as one of the highest-stakes decisions I make for my clients, my team, and my own peace of mind.
Krishna Rao is the CFO of Anthropic, and this is his first podcast appearance.
He joined the company two years ago when run-rate revenue was about $250M. Today it is $30B. He has helped raise ~$75B and is responsible for the procurement and allocation of compute.
I feel lucky we get to hear what it is like to sit inside a company this consequential at a moment this pivotal.
We discuss:
- The cone of uncertainty
- How he allocates compute across Trainium, TPUs, and GPUs
- What investors misunderstand about model companies
- Why the returns to frontier intelligence keep rising
- Platform vs application and where Anthropic builds its own products
- How Anthropic uses Claude internally
I have asked my closing question about the kindest thing more than 500 times. Krishna's answer is one I have never heard before.
Enjoy!
Timestamps:
0:00 Intro
2:38 The Compute Canvas
6:51 The "Cone of Uncertainty"
11:58 Why the Returns to Frontier Intelligence Are So High
16:45 Recursive Self-Improvement
20:20 Scaling Laws
23:30 Sourcing $100 Billion in Compute
28:05 Platform vs. Application Strategy
32:52 Pricing Dynamics
38:48 How Anthropic’s Finance Team Uses Claude
43:24 Raising Capital & Overcoming Investor Skepticism
52:32 Public Perception, Risks, and Government Regulation
57:25 Mythos Release
1:12:33 What Could Derail the AI Revolution?
1:13:47 Biotech and Healthcare
1:15:31 The Kindest Thing
If India survives Modi. That's a big if. So far, there's no sign of being able to run the country for the well-being of the masses, while there is every sign that he will hold on to power by hook or by crook - mostly by crook - by compromising institutions or outright violence.
By the time the public gets disillusioned enough, there will be little left to loot - but also no resources to rebuild with. Newer generations are growing up entirely out of touch with reality or the building blocks of civilization, so to say. Rational thinking is at an all time low. I seriously don't think our grandparents were as dumb as our contemporaries.
So far the Modi Era is looking more like the end of India than just a dark age to recover from.
I have been a student of this guy. He took a couple of lectures for my Machine Learning and Deep Learning summer bootcamp back in 2017-18ish when AIAYN came out. I think he taught me backprop piece. He has also been one of the most active GSoC mentors in Delhi. Truly a tragedy that India lost such a talent.
Can’t complain since I am out now too. Tried my piece by being a part of the government org - pushing for changes from inside for 3 years and losing to red tape. I was making pennies while my friends were doubling/tripling their income in the same period. I will be returning back home — but for my Maa and Paa — not for some deshbhakti ka churan. A trade off I am making conscientiously knowing very well the opportunities I am gonna let go.
Also, for Mr Deshbhakt Vembu, it was cheaper to move to India than pay the 1.7 billion in Alimony. So stop falling for that stupid gimmick that the fellow is selling. He made his empire by leveraging the arbitrage of exploitative IT services sector, serving clients in the US.
The only good reason for an NRI to return to India is if you are a billionaire trying cheat your ex-wife out of her fair share of divorce settlement.
Like this guy here. 👇👇👇
What delulu ! Record breaking heat in India is clearly making people dizzy. Just DON’T - be scientific in your approach. Look at numbers - $1 = ₹94. Temperature = 50C.
Open letter to @svembu
--
Dear Sir,
Amongst the trickle of those who come back to India - most do it for personal reasons. Some miss their family (others want to get away from them) Some miss the convenience of house helps (others we are told, fall in love with 10 minute delivery & UPI payments)
In the 2000's there was a time when post liberalisation euphoria and India's rapid economic climb - encouraged people to come back to their motherland. That that was the time when folks came back with a missionary zeal, the concept of 'reverse brain drain' had started to take root...now India is the global leader of exporting skilled labour & talent.
It seems that our political leadership takes inspiration from China's political authoritarianism - but not what it did to become an economic powerhouse. China did not beg folks to come back to motherland - it launched the Thousand Talents Plan - incentivising the best and brightest to come back home. We haven't tried yet.
Even your plea to Indians abroad - is trying to play on the fears to NRIs that they will get trapped in the battle between the 'hard right' & 'woke left' .... so the reason for coming back to India is not growth / opportunity / better life / healthier environment - but escaping persecution and xenophobia that is increasing. Still Indians are choosing to stay back. (Why?)
You spoke a lot about respect & I agree that global respect today comes from a nation's technological prowess. The question that you need to ask is - why is it - that despite 'producing sufficient brain power to achieve that prowess' we are nowhere on the technological horizon? Do have the courage to ask why has the Govt allowed the systematic decay of scientific thinking & R&D??
Forget getting talent back from America tomorrow... are we doing anything to stop the fleeing of talent abroad today? Where is the missionary zeal of the Govt in that?? Or the focus is ripping the social fabric more and getting more votes???
Finally about the respect that India always had abroad. That was not because of our nuclear bombs, our market size or chest thumping leaders - Indians ALWAYS got the respect because of our cultured civilisational values, non violent attitude, proclivity for hard work & family values.
You would have to agree Sridhar, that we are literally abandoning all this - while chasing some some false bravado, as if this is a Bollywood movie.
In the real world - unless and until we introspect where we went wrong, all this begging and pleading will be of no use & that brain drain will only keep increasing.
//
PS - The introspection should begin at home.
Thrice India elected a man who faked his degree, can barely converse diplomatically in any language, abandoned his wife, seems like a pathological narcissistic megalomaniac and accused of facilitating communal riots.
How else did you expect the term under him would be?
Hamming's talk is so important that I reproduced it on my site. It's one of the only things on my site written by someone else.
https://t.co/kWvKdwIiOm
Minute for minute, amongst the most insight-packed podcasts I’ve encountered of late. Exceptional episode featuring Keith @rabois in convo w @lennysan. Founders should listen / read / AI-parse the episode.
Notes on the podcast episode linked to in the reply tweet.