Cup of Zhou - Weekly Investor Musings to go with your Morning Coffee

November 13, 2026November 12, 2026

Creativity starts at 2 degrees

One degree of freedom removed from the status quo is what most people, even if they can’t do, can imagine. And because they can imagine it—”I could have come up with that idea myself”—what you have doesn’t feel innovative. They may ask you “why” once, but they’ll get to the answer they expect to hear pretty quickly.

Starting at two degrees of freedom removed, you start at the imagination’s imagination. The fringe of the fringe, so to speak. Then, by most people’s standards, you are creative. Not one standard deviation but two standard deviations from the mean. Which starts putting you in the uncommon 5%.

It’s where the average person starts calling you “built different”. I don’t know if that phrase means anything if it’s overused or used by people who refuse, for whatever reason, to be different themselves. But nevertheless, you are 1 in 20 of their friends who feel like they and their 19 other friends are doing the same thing. If you want to impress insiders and people labeled by others as “built different,” you need to be two more degrees of freedom removed from that. At least 4 degrees of freedom removed from the mean. So instead of “why,” they usually start their line of questioning with “how.” “How did you think of that?”

If you’re taking the ‘perfect’ stat sheet of a hire these days, across different variables (schooling, prior companies, prior job titles, years of experience, extracurriculars, skills, resume template, cover letter template), a normal applicant exudes familiarity across all the above variables. The “required” five years of experience across companies you’ve heard of, but may not be extremely exciting. They go on hikes on the weekends, hang out with friends, watch Netflix. They’re applying for a Director role through the job portal and submitted a cover letter with references, having been a Senior Manager and Manager before that. A hire that’s built different will have all the above, except for two. Instead of climbing the corporate ladder, they started a company and sold it to private equity. They didn’t apply through the job portal, but directly cold emailed the hiring manager delivering a deep dive report on what problems they see in the organization and how to fix them. That’s a hire that’s “built different.” But in the world of exceptionalism when there are hundreds, maybe thousands, who can/have done the same, you need all of the above and more. You built a media business on the side. You also went the unorthodox path of schooling yourself. Self-teaching. You created a podcast to interview people in this field to help you learn. You started more than one business here. And you’ve come via the referral of a board member.

If you’re an artist drawing a horse, the average artist will draw a long muzzle, side-set eyes, a mane, four legs, a tail, a smooth back and maybe a saddle. A innovative artist might instead draw a horse with a long muzzle, a side-set of eyes, a mane, four legs, a tail, but instead of a smooth back, draws with the armor of an armadillo. A creative artist will take all of the above, and change the legs to octopus arms and the tail into a skeletal one with a barbed one that ends with a flower. At some point, as you iterate more, it stops looking like a horse, and something else entirely.

I find this to be useful exercise in all areas that require imagination or in industries where there are incentives to be different. Craftsmanship and art being more obvious examples. Startups fundraising. VC funds fundraising. Saturation of the job market, especially with hires in AI requiring deep domain expertise and/or different perspectives. Football plays in overtime and you have the ball. Cold emails to busy people.

Of course, there are industries or moments where it pays to be the same. Where a large amount of trust is involved. Where the risk of something adventurous or out of scope could be catastrophic (to lives, to reputation, or to income/revenue). Where you only have so much wiggle room before you are alienated. Political campaigns. Kids asking for money from your parents to buy “groceries.” Neurosurgeons. Flying a plane with passengers (unless this is a Red Bull campaign). Choosing your safety gear when going free climbing.

But I dare say most could use some creativity.

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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

November 6, 2026November 7, 2026

Offloading vs Outsourcing

Offloading is when someone (or something i.e. AI) does the work that you know how to do yourself, but you would rather save the time you would have on the task on something else. You know how to course-correct an action, input and output. You know right from wrong. What makes sense from what makes no sense.

Outsourcing is when someone (or something) does work you don’t know how to do yourself. When you get a result, you don’t know if it’s a good or bad result. You have no idea the implications of that result. Everything seems to make sense.

When you’re new to a space or young in your career, and you have no prior relevant experience and context to rely on, you should avoid outsourcing at all costs. In other words, AI is quite detrimental as it stands now to help you become an expert. It will be world-class at helping you become mediocre.

The first time I read a term sheet having no other reference point, everything made sense to me. The first time I read an LPA, the same was true. The first time I read the clause “the general partner should spend a reasonable amount of time on the fund”, it seemed to check out. Only later did I realize that reasonable is not the same as significant or majority. Hell, even now, I know nothing about drug discovery. And AI for drug discovery made sense to me when I first heard it, but it wasn’t till I asked my friends in biotech did I realize there were many more limitations than I expected. The list goes on. Since there are a lot of things I know nothing about.

You should spend all your calories, time, attention, energy, resources, favors on getting guidance from more experienced professionals who have know-how that do not exist in the public domain. That LLMs have yet to get access to train on.

Wisdom cannot be outsourced to AI, podcasts, articles, tweets, social media, public panels and fireside chats, and arguably any medium where there is an audience that has no reason to withhold any secrets.

The only difference between offloading and outsourcing is taste.

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October 30, 2026October 30, 2026

Trust to Adopt

A few weeks back, I read one of Scott’s Implications posts on what AI adoption look like from here on out. I wrote about it on my other blog as well of my favorite takeaways, but for the purpose of this one, this quote particularly resonates.

“Explorers vs. Guardians” is the new “Visionaries vs. Pragmatists.” In previous eras, early adopting cohorts of customers known as “Visionaries” were those more willing and forgiving of a product’s shortcomings. Product teams worked tirelessly to improve their onboarding and polish their features to the point where later cohorts of customers, known as “Pragmatists,” could come in and find their way. Today, the early adopters are the “Explorers,” a cohort of customers willing to share their data and “trust by default,” despite the occasional misstep, as they explore the unknown. And the later cohorts of customers are the “Guardians,” who value their privacy as a precious asset and don’t want their data indexed. Trust is the bridge for Guardians to become Explorers.

The currency of adoption in the past used to be perks, discounts, free trials, and a little bit of brand and relationships (especially for enterprise).

The currency of adoption in the future is trust. Which, to be fair, are also won via brand and relationships.

a16z seems to like the phrasing of preferential attachment. While it’s still a slight mouthful, it is true. Similarly, one of the best pieces of advice I got early in my venture career was that it’s not about who you know, but who trusts what you know. In the age of AI, where all tech moats in software (and one day, hardware) have fallen, transactions are cemented over years, if not decades of trust. Trust not in the sense of pure “do I use the product?” but “do I trust this company with my data?” Trust over time is something that the market outside of the US has long prioritized, but still fairly foreign to a lot of US-based companies with a primarily US-centric customer base. The US, especially the bi-coastal regions, has long had a higher proportion of early adopters than other geographies. Ideas flowed freely. Interest in trying new things has long been the culture here. And because software was rather compartmentalized across entities, many of whom made switching costs really hard, adoption of new technologies was usually around niche or new use cases rather than old.

And in this world, where trust matters more than any other sales tactic, you either did a good job maintaining relationships and building and growing a brand where your intentions are clear, or you didn’t. And if either of the above two were an afterthought pre-AI, you’re a leg behind already. As two folks once told me, “someone can’t measure your competency until they see your intentions. If they deem you as competent before they know your intentions, it’ll actually have the adverse effect.”

So despite me not liking the idea of self-promotion and social media growth, the value an investor can bring to the table is helping a founder leapfrog their way into deeper layers of trust. Be it brand/marketing or pre-existing relationships.

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October 23, 2026October 23, 2026

Spikes, bumps, dents, cavities

A couple LPs and I were discussing the GPs we met this week. All who spend most of their time looking at emerging venture managers. Well it’s RAISE week, so everything’s hot in SF. Except the weather. Heat wave was last week. And as we were trading notes, and do note, this is highly anecdotal… 50% of GPs mentioned were very quick passes. In fact at some of the network-y events, LPs were trying to help each other get out of conversations with certain GPs. But that’s to no surprise, the same is true for many VC-founder events. About 40% of GPs mentioned felt good enough for us to continue the conversation, but not enough for any of us (assuming we didn’t know them already) to take next steps with them. And 10%, maybe less, were worth further conversations. Some of my friends reading this may claim less in the last cohort.

Do note, almost every LP who came into town this week, asked the local LPs or just each other, who are the 1-2 GPs they have to meet. So every LP, minus opportunistic chats, knew exactly who they wanted to meet before the week started.

All that to say, there were enough strong candidates for LP capital around this week. There are more well-rounded GPs in markets than ever before. Folks with classic venture training, enduring relationships, and/or founding experiences. Rewind 15 years prior, most of these folks would have been great GPs and potentially household names too. They’re highly responsive. They’ve got a good track record. Founders like them, and for the most part, they do try to be helpful as early as possible and as much as possible. They don’t pretend to be someone they’re not (there are plenty still who do). They’re well-connected to downstream capital, customers and/or talent. And in their niche, they have a lot of trust. And some of them have even been historically great fiduciaries of capital (i.e. comms, exiting positions, etc.).

But in Q4 2026 (yes it’s Q4 already), they’re just good (not great) in a lot of LP’s eyes.

Another thing I’ve noticed is that when LPs introduce GPs they’ve invested in to me that they like, there’s always a story. A very specific incident where everything clicked. One thing a GP is known for that makes them unforgettable that no one else has. Something small that sparked that upon continued exposure compounds again and again and still something most GPs don’t have.

And I can’t help but think about spikiness.

Spikiness is memorability.

In one instance, a friend and I were discussing a GP that I passed on before, but he thought was interesting. The conclusion was that this GP will most likely be a top quartile GP, but she didn’t have an obvious edge. My friend said that he thought she was interesting because she had a “subtle edge.”

A bump, if I might translate for a second.

Are bumps enough? Is that enough to attract the best founders? Do bumps matter more than spikes after a certain AUM? Are spikes no longer as valuable past a certain AUM?

To define some terms really quickly:

Spikes are edges. Absolute advantages. What you’re known for that very few other people are known for. What you can do that no one else can do. And that you’re in the top 0.0001%.
Bumps are comparative advantages. May not be unfair, but you are better than at least half of your competition. Potentially top quartile.
Dents are comparative disadvantages.
Cavities are absolute disadvantages.

While many LPs will have different answers to the above, with respect to emerging managers, a common thread seems to be that:

LPs like spiky GPs with no dents and no cavities. These GPs admittedly don’t exist. Or at least I haven’t come across.
So instead, LPs like spiky GPs with dents, but no cavities.
But they will take spiky GPs with cavities as long as the cavities don’t handicap their ability to create outsized returns.
LPs hesitate on investing in bumpy GPs with no spikes. Even if they have dents and no cavities.
LPs run away from GPs with cavities but no spikes or bumps.

And of course, the observations above come in lieu of track record and referenceable relationships that are easier for many allocators to underwrite.

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October 16, 2026October 15, 2026

Curiosity before Retention

My buddy recently asked me to give some advice to an early-stage consumer social company. And the company asked if they should focus on growth or retention first. Both are equally as important for a business designed for venture growth.

If you only focus completely on growth, you’re going to have a leaky bucket. We saw this with many of the AI applications that launched in the last few years. Image generation. Video generation. App building. The quality of the product makes the product go viral. Everyone uses it. Then when the next higher quality product comes, they move. Either that, or the one week free wasn’t enough for people to use it beyond casually.

If you focus completely on retention, you have mom and dad and friends using your product, but depending on how much runway you have, may not be able to sustain the business nor attract investors.

And given the short(ish) runway of the company, I told them to focus 80% of their time and energy on growth first to attract investor dollars, but build with the remaining 20% for retention mechanics in the background.

Without getting too specific on the exact company and the exact steps they are taking, first step, get people on the platform, and the only metric outside of growth you should be optimizing for is the login the day after (24 hours later). In the meantime, build notification and engagement mechanisms following the Ebbinghaus’ Forgetting Curve intervals. 2 hours. 24 hours. 3 days. 7 days. 30 days. And 90 days. Moving short term memory to the long-term memory bank.

The notification system, moreover, should activate at least one, but ideally two of George Loewenstein’s five triggers to curiosity.

Novelty — Access to information known to others
Partial exposure — Reminders of something forgotten, but also “insider gossip”
Complexity — Questions and riddles
Uncertainty — Unknown resolutions
Conflict — Violated expectations.

If people have enough reasons to come back to the platform, at some point, it’ll become muscle memory.

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October 9, 2026October 9, 2026

LPs Judging Each Other

I had a conversation with both a family office and a fund-of-funds this week about the same topic. All of us at a high level agree on the premise of it (with nuances at the edges). And within 24 hours of each other, so I now feel compelled to write about it.

There are four sets of GPs we come across as LPs.

GPs we love and end up backing
GPs we think are really interesting, but for whatever reason, choose to wait and track
GPs we pass on really quickly
And, GPs we, unfortunately, because the stars don’t align (or whatever the horoscope folks say, when Jupiter meets Neptune or Mars is in retrograde… clearly not a astrologist), fail to give any respectable attention to, and never even began to dig in at all.

The last one is unfortunate. Truly. But it happens. A stray LinkedIn message. An email that slips through the inbox. A chance meeting at an event with no follow up.

Now this post is about judging.

Not all LPs see eye-to-eye on investments. Sometimes I’ll find a GP particularly fascinating, and my peer won’t see the same brilliance. And vice versa. But most of us do agree, to some extent, that the sum of our first set of GPs (ones we invest in) and our second set of GPs (ones we’re tracking but didn’t invest in) is roughly the same as each other’s. In other words, if another LP I respect has invested in a fund that I didn’t, I am most likely tracking that fund. And even though another LP friend may not invest in the same funds that I do, they are most likely tracking the GPs I’ve invested in. What’s good enough to invest for one LP is good enough to invest to track for another.

What raises the eyebrow is usually coming across an LP who has a consistent track record of investing in funds that you yourself pass on rather quickly. The third set of GPs. One, maybe two, fine. It happens. You may have missed something when skimming quickly. But if there are three or more GPs in one’s own third set but in another LP’s first set, one starts questioning their judgment. And it seems that the family office LP and the fund-of-funds manager also agree.

One caveat to note… this only really applies to LPs who primarily focus on venture. The unfortunate circumstance of LPs who don’t focus only on venture is that given limited bandwidth, they’re likely to have a lot more GPs in a given asset class in the third camp than LPs who only focus on one asset class.

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September 29, 2026September 28, 2026

Motivations

Crossposting this from my LP specific Substack…

I met a family office last week and she asked me a really interesting question. Probably the question a lot of us are asking ourselves. Whether you’re a VC or an LP or someone looking to hire team members.

How does one really understand another person?

The short answer is I’m still looking for the answer to that question myself. And probably will continue to do so till the day I die. Kinda like one of those questions… What is the purpose of life? Is there other sentient life in the universe besides us and what are they like? What happens to all the memories we forget? But I digress, though you can probably guess I’m writing this piece in a good mood 🙂

And so I responded.

Doubt I or anyone really has the answer to that. But there’s that Charlie Munger line: “Show me the incentives, and I’ll show you the outcome.”

My first step in every investment conversation is understanding why someone does what they do. Are they trying to prove someone wrong (ie a parent, an ex, their kids, former boss, etc.)? What is their chip on shoulder if they have any? What gives them joy? What gives them pride? How do they identify themselves? Who do they see themselves as? Is there something they’re unwilling to tell me? Why? What’s stopping them?

And some permutation of the questions below is what usually comes up in conversation. While I don’t have a checklist of questions I have to ask, as long as I’m not sure what my sparring partner’s motivation is, I keep trying to figure out. Hopefully, the below questions serve as inspiration for you. Or are just more questions to your arsenal.

What is your selfless motivation—the one that goes in the Forbes interview? What is your selfish motivation—the one you tell yourself when you’re struggling? Your selfless motivation will inspire you on your best days. Your selfish one will keep you going on your worst.
What do you want to have written on your epitaph? Do you have adjectives or words you particularly like?
What is the greatest regret you’ve had? Why?
What’s the greatest thing you’ve ever done that no one around you knows about? Proudest?
What’s the proudest sacrifice you’ve made that no one knows about?
Is there a question no one has ever asked you but you would like to give the answer to?
What is a question you feel uncomfortable asking me?
Is there a set of questions you would feel uncomfortable if I asked you?
Why did your spouse first fall in love with you?
Why do you think each of your former bosses hired you? Would you say they all hired you for the same reason?
What’s the closest you came to breaking?

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September 23, 2026September 22, 2026

Questions

My girlfriend and I hosted a tea tasting omakase at our home over the weekend. Three teas and tea pairings across a few hours, with activities mixed in.

Our friends really seemed to like the questions they were asked as part of our icebreaker at the very beginning of the tea tasting experience. So thought that it might be worth sharing for all of you, as, say, introspective queries that you might journal with. Call them journaling prompts. Or 69 questions to fall in love? The number 69 was not intentional, by the way.

The below are just a combinations of questions that I’ve liked over the years, questions I’ve heard from others that I liked, and questions I’ve personally come up with. If you’ve been around here for a while, you might see some familiar lines of queries from the podcast, this blog, and even my question-off with Kevin.

528 Hz is the love frequency. The miracle tone. The Solfeggio frequency — that very pitch — that certain songs are tuned to make you feel inspired and emotional. To take a different definition of the word pitch, was there a pitch or story you’ve heard in the past that inspired you to take action for seemingly unexplained reasons?
If you could open a store and only sell one object that is meaningful to you, what would you sell?
What’s the closest you came to breaking?
What’s an adjective you would use to describe your relationship with your mom?
It’s the last day of kindergarten, and you have the chance to walk home with the child you once were. What would you say to them?
What is it you do that you use to give you confidence?
What is a question you feel uncomfortable asking me?
What’s something difficult you’re going through that people don’t often see?
Is there a single question or a set of questions that has yielded you outsized returns when it comes to getting to know a person?
Charlie Chaplin has this great line where he says, “Life is a tragedy when seen in close-up, but comedy in long-shot.” Do you remember a part of your career or life that seemed like a tragedy in the moment, but is something you laugh about now?
What were some of your come to Jesus moments in the past few decades that your friends may fail to appreciate?
I’m curious, as you one day age and start to slowly lose your memories, what would be the last memory you would hold dear?
Has there been a habit or practice you’ve observed from a friend or colleague that you’ve worked into your own rotation?
What does one need to understand about your childhood and early upbringing to fully appreciate the person you are today?
If someone were to look at your calendar and only your calendar, what would they say your priorities are? What would you like to say are your priorities?
If you could pick any of the lessons in your life to canonize in a time capsule, which two would you pick?
Is there a routine or framework that serves as the scaffolding to how you think about life?
What, if anything, do your friends/spouse/family often oversimplify about being you? And what, if at all, do they often overcomplicate?
What’s the worst pain you’ve ever been in that wasn’t physical?
What’s the one “what if” that keeps you up at night?
What’s the biggest chance you never took?
What or who have you given up on?
Steve Jobs famously said that a typography class he took back in school was one of the most seminal experiences in his life and how he ended up building Apple. I’m curious, for you, was there a moment that you would attribute much, if not most, of how your mind works today?
What do you think makes your partner so successful?
In what ways do success fuel ambition and how might success damage ambition and hunger?
When’s the last time you had a pinch-me moment?
What talent do you have that you’re not using?
What is the no or refusal you keep postponing?
What commitments have you made that you no longer believe in?
What is the gift you currently hold in exile?
Is there anything you think the world is too dogmatic on? And in what ways are they too skeptical?
What in your life before you turned 18 was most formative to the person you are today?
If today, you could pick the age you’d pass away, assuming you’d be healthy the whole time, what age would it be? And why?
What’s a system or game you’ve hacked in the past year?
Can you think of a recent example where you said yes to something you shouldn’t have?
What was your first failure?
1. How did you know when to quit?
If you were to put together the perfect human being piece by piece Mr. Potato Head-style, how would you go about it?
If you were the main character of a movie about your life and you had an audience watching said movie, what would the audience be screaming at you to do?
If all your writing, speaking, and ideas were erased from the internet, and you only had the next 60 seconds to impart your wisdom, what would you say to the world?
There’s a quote from the show The Office. “I wish there was a way to know you’re in the good old days before you’ve actually left them.” With all the doom and gloom around us today, what are reminders you keep close to your heart that today, we’re in the good old days?
What was your earliest relationship with money?
What is it you do to train that is comparable to a pianist practicing scales? Or a swimmer going to 5AM practice just to practice a single arm stroke?
Do you see yourself as part of an intellectual heritage? Who is on your tree?
When you have time to wonder, what’s the thought or idea you regularly find yourself coming back to because you find it so interesting?
If someone who knows you well were to write a product review of you, what features and bugs would they list out?
How much of your advice is a function of a glass half full? And how much of it is a function of a glass half empty?
What is the greatest accomplishment that you regret having achieved?
What is one major decision you’ve made where it was better to not overintellectualize the decision making process?
What was the harshest piece of criticism you gave where you knew that that individual or project was providing more meaningful value to the world than your criticism gave it credit for?
What part of you is a mystery to you, the part of you that you least understand?
What’s the most persistent myth people have about you that you’ve never bothered to correct?
If you could pay a monthly subscription to be a fly on the wall of the life of one person, who would it be?
When was the first time you had to be the adult in the room?
How do you tread the terrain between doing what’s expected and doing the unexpected?
What is your earliest childhood memory that’s so deeply imprinted in your mind that all else fails to compare?
Which role have you taken on in your career made you the most nervous as a professional and what felt most immediately like home?
If someone wanted to do some serious mudslinging, what is the least charitable interpretation of everything you’ve built, of everything you’ve done to date?
There’s a great line by Soren Kierkegard. “Life is an ironic tragedy, it has to be lived forward but only makes sense in reverse.” For all the events and experiences that serve as building blocks of who you are today, what parts of that lore were more incidental than intentional?
There’s a scene from the show The West Wing said by the late John Spencer who plays Leo, and the story he shares is: “This guy’s walking down the street when he falls in a hole. The walls are so steep he can’t get out. A doctor passes by and the guy shouts up, Hey you, can you help me out? The doctor writes a prescription, throws it down in the hole, and moves on. A priest comes along and the guy shouts up, ‘Father I’m down in this hole. Can you help me out?’ The priest writes out a prayer, throws it down in the hole, and moves on. Then a friend walks by, ‘Hey Joe, it’s me. Can you help me out?’ And the friend jumps in the hole. Our guy says, ‘Are you stupid? Now we’re both down here.’ The friend says, ‘Yeah, but I’ve been down here before and I know the way out.’ For someone who’s felt the growing pains of life, who were your friends who jumped in the hole with you?
If you wrote a book where the first and last sentences were the same but had different meanings, what would it be?
“What most people call authenticity is a costume for childhood beliefs.” I’m curious for you, what are the most seminal experiences you had and remember from your childhood that shape the way you interact with people today?
There’s an interesting quote by Rishabh Gautam. “Waterfalls wouldn’t sound so melodious if there were no rocks in their way.” You’ve reached heights that most people can only dream of, but I’m curious, what were the rocks that stood in your way?
What is one thing you believe in that most people would fight you on?
If you could relive one of your career highlights as a semi-regular recurring dream, which one would it be and why?
Would you rather relive your childhood or see the lives of one of your parents before you were born?
There’s a really interesting quote attributed to Voltaire. “Change is annoying, but certainty is absurd.” What are you willing to be absurd about?
George Bernard Shaw once said: “The single biggest problem in communication is the illusion that it has taken place.” Of all the quiet things that should be said aloud, what were/are your biggest offenders of the illusion of communication?
What version of yourself do you miss sometimes?
If your partner asked you, what’s one thing you sacrificed for me that I don’t know about, what would you have told them?

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September 18, 2026September 18, 2026

DPI is a Harsh Judge

Yesterday, I was watching a reshowing of Gwynne Shotwell and Elon Musk at the 2026 All-In Summit. Perks of the attention economy are that almost all content these days no longer have exclusivity. And if so, there’s only a small window of that arbitrage. Nevertheless, I digress.

In it, Elon says, “Physics is a harsh judge.” And well it got me thinking. We live in a world where DPI (distributions to paid-in capital) is a harsh judge.

And I say DPI in a royal sense. It really is realized IRR. ‘Cause 3X DPI in 15 years is quite bad. Your Benjamins are better in the money market growing 8% a year. Not that much better but better. 3.17X to 3X. But benefit of the money market is your capital is liquid. But I will use DPI for the purpose of this piece because it rolls off the tongue better. Or rolls off the fingers…? You get my point.

But unlike the world where physics is a harsh judge, DPI is not instantaneous.

I was also catching up with a friend yesterday and he said something with respect to recursive self-improvement (RSI). For the layman, aka me as well, the process in which the AI learns by itself from itself. In other words, an AI capable of rewriting their own code. It’s a great theory and we see quite a few companies working on turning this into a reality. But the most interesting takeaway I got from that conversation was that “recursive self-improvement only works if it doesn’t take up time. If it takes time, you can’t do that many turns. Then the harness becomes the only thing you iterate on, but that undermines any moats.” In fact, building a Claude skill is the equivalent of retraining the harness after each task. Requires little time spent, but anyone can do so.

Similarly, because DPI is realized after an incredibly long feedback cycle, 5-8 years at best, you don’t have much time to retrain the model more than a small handful of times before, well, your life expectancy. So, in lieu of DPI, LPs look for other signals that act as a proxy to the harsh judge.

Mark-ups become the mild judge.

Revenue growth and talent density become the gentle judge.

And brand is the lenient judge.

And when things are too lenient, you no longer have one judge, but an army of judges. Anyone can judge you. Everyone is your jury. And all you need is one viral tweet to be your executioner.

So, when LPs say they underwrite you on discipline, at least this is what I look for, and my generous interpretation of what other LPs look for, they’re underwriting you to what can you do today that exists on a faster feedback cycle and what is easy to make evident your ability to compound your existing assets. In other words, between Fund I and II, what is the metric you would like to give LPs for them to assess your rate of change?

Now it’s up to LPs to decide if that metric holds gravity or not. But you at least have to provide one. In its absence, we are back at square one. DPI is a harsh judge.

Photo by Sasun Bughdaryan on Unsplash

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September 10, 2026September 9, 2026

When she complains about the dishes…

This is a repost of a piece I wrote earlier this week on my investing topic only blog that seemed to get good feedback, so sharing here as well, in hopes that it is helpful to you as well.

The post is for GPs who’ve gotten rejections from LPs, but I think the analogy stands if you’re a founder hearing back from a VC, or anyone who is doing any kind of fundraising or sales.

One of the most memorable pieces of relationship advice I’ve gotten is that line. “When she complains about the dishes, it’s not about the dishes.”

By the time your spouse complains about the dishes, it’s a culmination of other pent-up emotions simmering at the surface. And when she says it’s the dishes, it’s not. Potentially it never was. But it may have been the reason that tipped her over the edge.

That said, this is not a post about relationships. I’m not a marriage counselor or a relationship coach. This is a post about rejections. And all the reasons that come with rejections. Or more specifically, about LPs passing on GPs. Or hell, VCs passing on founders.

And yes, I’m going to use gendered language but it’s purely for the purpose of extending this analogy and lesson my friend gave me. So I hope you allow me this literary liberty.

When she complains about you being too early, it’s that she never had conviction over the deal. When she says you need more traction (track record), it’s because she couldn’t see why you would see and win the most interesting deals in your space. What you say has yet to be proven by what you did. So, the underwriting will start now for what you will do. She doesn’t trust you can execute against what you promised. You’re either talking a big game (using superlatives that feel disingenuous) and/or you create a feeling of naivete. Be assured that the best allocators will be keeping track of what you promised before. Even if you, as a GP, rewrite your Docsend pitch deck. Admittedly, still, most won’t.

You will wonder why she backs others with no track record and no prior relationship with her. And 9 out of 10 times, it’s a communication issue in the first (few) meetings. You gave her no reason to generate enough dopamine that would get her to act outside of the meeting.

When she complains about there being higher priority opportunities, your strategy doesn’t align with the organization’s strategy. She likely did some work, and her initial work and/or references discounted the initial enthusiasm she had. She didn’t know how to say no politely and without seeming like an asshole. So only after a few meetings, and only after she’s felt like she’s given you the time and respect she thinks you deserve (whether you accept it or not), she can finally pass. Your problem is you never figured out what her motivations are. What she wants in her career. What her “family” (organization) wants of her. What keeps her up at night. Why she wants to go to work every Monday.

When she complains that there isn’t enough capital to left to deploy, it’s the fact you aren’t good enough to be an exception that would help her raise her next vehicle or to get board approval. Excluding institutions (including family offices) who own their own pool of evergreen capital, anyone who has to ask other stakeholders for more capital to invest has at least 20-30% left to deploy when they go out to raise their next vehicle. The primary motivator for the remainder of capital are people or opportunities that best highlight an allocator’s promise to their stakeholders. Fund-of-funds promise access. That means either a multi-million dollar allocation in Anthropic or an individual (usually spinout, but sometimes highly reputable founder/operator) who’s been early in generational opportunities. Others, like multi-family offices, depending on their mandate, either promise access or their ability to pick great pickers, which means 5X+ DPI in 5 years in a prior fund is extraordinarily exciting. Realized IRR or DPI matter a lot.

When she gives you a whole list of reasons as to why they’re passing, it’s because of the first reason, but she needed a laundry list of reasons to justify the one small thing she felt like she would get judged for. But that small thing came up as a recurring theme again and again, among references, among pushback from her investment committee, among her own doubts she never unearthed with you. One reason is all you need to pass. One reason is all you need. And sometimes, it’s the dirty laundry (i.e. gossiping). Or the speed of your communication. Sometimes, it’s the fact that you boast about another LP competitor in front of them. Sometimes, it’s the fact that you forgot what you talked about in the last meeting. The reasons will always feel like bullshit to you. But trust me, they’re as real, and as meaningful as they get.

When she doesn’t complain at all and just disappears from your life, she didn’t feel safe with you to give you the feedback you ought to hear. She feared your reaction, or at least the expectation of your reaction. You never provided the safe space she needed. It’s likely because of how you talked about others. The more judgmental you are about others, the more she’ll think… if things go awry, will you say the same about me behind my back? Can you even handle any amount of criticism?

There’s another great line on communication, but also on relationships by writer and poet Khalil Gibran. “Between what is said and not meant, and what is meant and not said, most of love is lost.”

If there’s one takeaway you need from this post, whether you’re a LP, there is more love (and reputation) lost in the lack of communication than in overcommunicating.

Photo by Scott Umstattd on Unsplash

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