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

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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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.

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.

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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.

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September 4, 2026September 3, 2026

The Danger of the Value-Add Investor

I’ve been a believer for a long time that our jobs as LPs (especially if we’re on the LPAC) is to be the parent at the playground. I don’t care which slides, swings, trampolines, or rock climbing walls you scale up. You are welcome to play however you want within the sandbox (your thesis). But when we see you flipping upside down on a swing or doing dangerous maneuvers that can lead to bodily harm, that’s when we step in as the parent.

We see those “dangerous maneuvers” in fund updates, at AGMs, in LP reach outs, in LPA terms, or hell, in regular conversations. I don’t give unsolicited feedback. Just my personal rule. The only exception I make to that rule is if I see something you’re doing as a GP that could have downstream negative impact to you or the fund.

Our job is not to look you straight in the eye with everything you do. Our job is not to be the helicopter parent and scold you at every turn. But I will always keep you in my field of vision, out of the corner of my eye, to make sure you’re staying safe.

To take a step back, there’s an interesting parenting rule I came across a while back. “Prepare the child for the road, not the road for the child.”

Here’s what I’m seeing:

Fund-of-funds replacing emerging managers’ marketing and community roles (aka FoFs are doing those roles for GPs)
GPs who believe in king-making. Folks who are doing everything from customer intros to closing customers for founders to hiring and managing all executive positions to finding the co-founder for the founders. So to speak. preparing the road for the child.
GPs who double as therapists
LPs who “anchor” your fund, but they take your entire fund

How much help is too much help? How much help handicaps the founders or GPs from what they do next? How does the value-add around certain metrics (i.e. ARR, concentration of customers, time spent fundraising, etc.) by investors mask the a founder’s own ability to achieve success? Have you prepared the road for the child?

My classic venture training told me that startups need to pull off 10-15 miracles before their company succeeds. Will those “miracles” carry the same lessons, scar tissue, and weight in a founder’s mind if the investor does 50%+ of that job for them?

A chick has to eventually leave the nest.

“Good” news is that most VCs are not helpful. And while many say they are or want to be, their calendar, their actions speak differently. Bad(?) news is that this wave of emerging managers feel they need to be valuable in order to stand out. I fear for the over-optimization of the perception to be helpful, rather than actually being helpful.

But to borrow two quotes from two friends:

“VCs are terrible.” From a friend who’s been in this world for decades having grown one of the most recognizable names in venture. The average VC isn’t helpful. Which is fine. As long as that’s communicated to the founders at the forefront of the investment. Quite a few VCs claim to be helpful. About the same number try to be, most fall short. In fact, more and more emerging GPs are doing so. And many end up optimizing for their own incentives, and not the founders’. Many want board seats, but do not understand the fiduciary gravity of being one. Many make 1-2 intros and act like the founders owe them, whether or not the intros landed any meaningful progress for the founders. And we’re sitting just before the wave of value-add LPs.
“Just because I have court side seats to the Warriors games does not mean I can replace Steph.” From an emerging GP and basketball fan whose first fund sits at 8X DPI. Despite his success as an investor and as a founder, it’s easy to conflate seeing the action from afar as prescriptive on how to play the game. Most VCs and LPs have had some version of court side seats. Some even further in the stadium. Yet many investors try to offer value and/or advice as if they have a crystal ball.

In doing off-list references on a fund recently, I was chatting with a founder that the VC backed and she said she would never take his money again in her next company. When I asked why, she said, “I have a job to do, but he keeps texting me ideas he has for the business and making single opt-in intros. I’m too busy to respond.”

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August 27, 2026August 26, 2026

Knife Shopping

A friend of mine was in the market for a new chef knife. The first one his wife wanted to cherish and asked me for thoughts, which gave me my little stage time to nerd out. And I thought… hell, might as well share my thoughts here as well.

So, a couple things to consider when you’re choosing a knife. For now, I’m going to exclude most of my commentary on how to take care of knives (i.e. wash, knife cloth, sharpening on whetstones, etc.).

How do you cut? Up/down or rolling motions?
What will you cut most of the time?
How often will you use the knife? Daily? Or for special occasions?
How important is knife control to you? Do you like letting gravity “do the work”?

Given your answers to the above questions, it’s easier to then figure out if German or Japanese steel is better for you, the heat treatment/HRC, full tang or hidden tang, and so on.

So let’s take this one by one.

If you cut up and down, Eastern/Japanese knife shapes may serve you better as they have straighter edges. Western/German knives have more curvature along the knife’s edge, which is useful if you cut in a rowing motion.

In general, full tang (meaning the metal of the blade extends all the way to the back of the handle) means you’re controlling the knife more. Whereas hidden tang (the metal of the blade extends partway through the handle) is more front-weighted, and more popular among chefs who “let the knife do the work.”

If you’re cutting veggies and fruits or in general softer material, knives with higher HRC (Rockwell Hardness C-scale) where higher means the metal is cooled faster, are better. And in general, allows for thinner knives and more precise cuts. Think sushi knives. Personally, I think an HRC of 58 is good enough for regular use. But some prefer 59+. The upside is that they retain their edge longer. The downside is they chip more easily then lower HRC numbers (cooled more slowly when making the knife). Lower HRC knives are better for cutting bones and hard material. They tend to dent (softer metal) rather than chip. Think meat cleavers.

If you’re using a knife regularly, say at least 3-4 times per week, I’d recommend going stainless steel (which is what most people prefer anyway) instead of carbon steel. The latter rusts easily (or patinas easily, the layer of rust that develops on the outside of low alloy high carbon knives). Also easier to upkeep with repeated washes. Do dry with a cloth instead of letting them air dry though. Knife oil helps, but is not mandatory on stainless steel knives. For presentation or special occasion purposes, aka to show off, a lot of people prefer the looks of high carbon steel knives.

In general, you can get a great starter knife for $80-200. Up to $500 if you want to splurge. But anything north of that is really the premium you’re willing to pay for each artisan.

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August 21, 2026August 20, 2026

On spinouts

When British voters voted for Brexit in 2016, comedian James Acaster gave a hilarious and apt analogy.

When you make tea, “if you leave the [tea] bag in, and over time, the cup of tea itself as a whole gets stronger. And it might appear like the bag is getting weaker but it’s now part of a stronger cup of tea. Whereas if you take the bag out, the tea is now quite weak, and the bag itself goes directly in the bin.”

I think that’s the case with a lot of spinouts. Not all. But a lot.

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August 14, 2026August 14, 2026

What is your play style?

On a quarterly alchemy session with my buddy Matt (yes, we have a quarterly-ish ideation/philosophical debate session), he asked me, “If you were a video game character, with both pre-set stats as well as the stat points you’ve accumulated through experience to date, what’s your play style? How would you best utilize your stats and skill trees towards your goals?” Furthermore, how might someone else with the exact same stats play your character differently?

First off, I like video games. I had a gamer in me in my past. Probably still, if I were given the chance to restart. But alas, a dangerous trade for me. So do note the bias in the intellectual resonance I had with the question.

Secondly, the underlying assumption in this line of questioning is that while the distribution of stat points vary per person, there exist others who would have the same set of stats as you do and the same skill trees. The same builds. But just because you have the same builds does not mean you have to have the same play style.

Thirdly, that last question is probably most interesting. How might someone else with the exact same stats play your character differently? How might someone else reach a different conclusion to “min-max” your play style? Or potentially more critically, how are you not leveraging certain skill trees to maximize your odds of “beating the game”? Skill trees that are underutilized or have been set aside to collect dust so far. Skills you earned as a child. Or in college. Or in your first job that you failed to keep putting the pedal to the metal.

To take the gaming analogy further, every time there’s a new update, your character build has to evolve with the associated nerfs and buffs to certain skill trees. In other words, with each new world order, are your past skills more or less relevant? As such, you need to change your build every world “update.” Be it the internet to the cloud/SaaS era to the AGI era and so on. Given the pace of technology and culture, there will be several “updates” to the world within your lifetime. And no one wants to play a character with an obsolete build.

I can’t take credit for this since I haven’t read the book yet, but when I was telling another friend about the above, she used the phrase “the leash of your past” inspired by a chapter in Björn Natthiko Lindeblad’s I May Be Wrong. Which I think is quite apt to this analogy.

After all, your past self won’t thank you for staying the same, but your future self would wish you changed sooner.

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August 7, 2026August 6, 2026

“Be strong enough to be gentle”

Three conversations happened recently.

One, an LP told me that he pit two fund managers against each other by asking their shared portfolio founder, “If you could only choose one, who would you keep as an LP?” Then went on to relay that answer back to both of the respective managers.

The manager who lost the vote shrugged and didn’t feel the need to really engage in the ragebait. The one who won the vote ended up making some remarks along the lines of “I don’t see why anyone would ever want to work with [insert other GP’s name].”

Two, similarly, I met a GP for the first time last week who pitched me a strategy he thought was unique. To which I responded with, “What are your thoughts on [insert VC firms with similar theses]?” He replied with a whole list of reasons of “why X, Y, and Z should never be in business in the first place.”

Three, I caught up with another Fund I GP earlier this week. Second conversation, who pitched me a strategy he thought no one else was doing. I asked the same question, listing some competitors with the same strategy, stage, and focus. He said he’d never heard of them, then asked me to repeat those names. He Googled each. Scrolled through their portfolio and website and LinkedIns. Then started his response with, “I guess I’m not as unique as I thought I was. Here’s what I think they’re doing right…”

All three conversations carry notes of similarity. Each either directly or indirectly ending with one of two paths. In the first one with the LP, do I agree with his method of execution? Not really. But nevertheless, he received the answer he was seeking.

Yet in all three, I can’t help but be reminded of something Peter Cullen (who’s best known for being the voice of Optimus Prime from Transformers) said.

It’s not immediately apparent on the relevance. But he says, as the inspiration for how he voiced Optimus Prime, “Be strong enough to be gentle.”

True strength and mastery has no need for infighting. No need to demean others. No need to push others down only so that they will look better by comparison. Most Midas investors I know are not bragging about the fact they’re on the Midas List, at least I haven’t heard Vinod or Marc brag about it. They’re on the Midas List because they can pick great companies. It’s not that being on the Midas List allows them to pick great companies.

Those that are the best of their craft, across industries, and that I’ve been lucky enough to be in their presence are both gentle and generous with their learnings. What’s proprietary is the execution not the idea. And by being generous and gentle, you end up commanding a lot more respect and admiration. If you’re truly stronger than others, you know how to control your strength. And only use it, when necessary. Most situations do not demand the necessity.

You need not prove your strength to a flower. Neither a butterfly. You need not prove your strength to a baby. To a feather. The inability to control one’s strength for the situation required can only exist in the absence of maturity. And the absence of mastery.

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July 31, 2026July 30, 2026

The Wrong Question for the Ambitious

I was chatting with a friend over the weekend who made me look stupid.

We were catching up after a while and we were talking about career paths and opportunities, and I had shared that I was offered to join a few large institutions late last year and earlier this year. Both of which I eventually turned down. And that one of the canonizing questions I had in the back of my head among 2-3 others was: When I leave, could I say I was successful because of the institution or in spite of the institution?

And for the first time, after sharing that set of questions with a few friends when I was in the process of making a decision, someone called me out. “That’s a bad question. That’s a horrible question.”

He goes on, “The question presumes that you are either joining a has-been or never-was institution OR that you couldn’t do anything meaningful while you were there. Given the names you’ve told me, the former is most likely not true. Instead, the framing of the question should be:

“What can you do at this institution that no one else with that job title has done?

“Something you actually wrote about before. On top of that, what can you do at this institution that no other institution would allow you to do? And how can you leverage the hell out of that? Why would you even join an institution where you can’t even leverage their success to date? That would make you look dumb for joining a bad institution when you have the opportunity to join a great one.”

Photo by Timothy Barlin on Unsplash

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July 20, 2026July 19, 2026

Why invest in a FoF

We’ve had a number of family offices (FOs) ask Sam and I for advice recently on investing in venture. And Sam shared a post recently on exactly that, which I highly recommend reading if you’re considering investing in a fund-of-funds. This post is more of an elaboration, a continuation on his.

Some of which have had experience investing in startups. Others in venture funds. And many still, absolutely no venture exposure in their portfolio. And a fraction of them want to.

Some have reached the conclusion that it makes sense to invest in funds-of-funds (FoF), which we’re a big proponent of. That said, not all fund-of-funds are created equal.

Yes, different FoFs will pitch different value-adds to GPs. And yes, different FoFs will pitch different strategies — anchor versus co-invest versus secondaries versus asset class diversification versus lower fees. And yes, different FoFs will tell you they have access to different pools of GP talent.

But your motivations for investing in venture as an asset class are often different as a family office.

Some FOs want to invest in venture passively and use FoF exposure to give them comprehensive exposure to VC. Kind of the set-it-and-forget-it mentality. As long as the asset appreciates 10-15% per year. Here, families look for institutional processes. Do the FoF GPs know how to run a fundraising process? Is reporting and communication clear and timely? Do all interactions have a feel of polish? How many managers do these GPs see per year? Are they in embedded networks?

Some FOs want to eventually directly invest in startups, but want to use FoFs to have co-invest exposure, as well as learn how to underwrite deals. In fact, I talked to two family offices last week. One of which invested in a FoF who invested in Sequoia because they wanted access to Anthropic. Another because they wanted to invest via an SPV into a hot AI infrastructure deal. Here, they’re looking for thoughtful and elaborate memos. AI-written memos only go so far. They want to ask questions. Here, FOs are unlikely to move fast. In fact, they’re looking to spend time to get conviction on a deal. Webinars, meets and greets with founders, regular internal content pieces about why a space/vertical or a company in the underlying portfolio is exciting is paramount before an SPV gets put in front of them. Assuming they’re not looking for the same ol’ pre-IPO, blue chip names, they not only need to trust the FoF’s taste, but also the underlying GP’s taste and why the space is exciting. Returns from the FoF matter less than their individual returns from investing in the SPVs or direct vehicles.

Other FOs want to invest in venture funds due to a portfolio approach rather than being a stock picker, but hesitate at the risk-reward profile of unproven managers, so will only invest in Fund III+ (maybe Fund IV and onwards), and need FoFs to do the diligence/relationship-building for them. Yes, this is also true for a lot of institutional capital in general. It’s for that reason, that they typically say, “It takes us 3-7 years to get to know a manager.” The number of years itself is arbitrary. Depending on where on the totem pole an individual sits (for institutions), they’re motivations for punting the conversation till later varies from “Is this deal going to get me promoted/fired?” to “I just don’t have the time in the immediate future to spend disproportionate time on one deal that’s asking for the smallest ever check size I can write in the smallest asset class I allocate to.”

Similar to the above archetype who likes co-invests, but with an added layer of dinners, happy hours, and invitations to events where they get to meet different portfolio GPs helps them build conviction. The frequency of these don’t have to be as often as with founders, just because knowledge and insight atrophy faster than relationships with people. Individual returns from best-performing GPs matter more than the overall FoF returns. Batting average matters less than magnitude of the home runs.

Others still want to build their own fund-of-funds program, but don’t know how to and want to see how the best operate before pursuing it themselves. They would like regular calls with the FoF GPs, frequent texts back and forth and the liberty to ask rookie questions. For many FOs, we usually tell them it’s hard to expect these unless you’re an early commit to a brand new FoF, or you are at least a 5% check of the overall FoF size. Our general recommendation is that as a family office, you also commit to investing in the next vintage as well, so the GPs of the fund-of-funds have a reason to continue to the conversation with you. Simply, because, well… oftentimes, GPs whether a FoF or venture fund could be short-sighted in their ways of thinking. That also means if you have $5M to invest in a fund-of-funds, it generally makes sense to split that check up to invest $1-2M in the first vintage of a $30-50M FoF and double down in the second vintage if you are able to get what you want out of the relationship.

Returns also don’t matter as much, but these FOs will want to have at least seen what quality GPs look like. Ideally through the portfolio of the FoF, but if not that, at least through events and interactions made by the FoF.

There are those who want to put capital towards impact initiatives and fund-of-funds with an ESG/DEI mandate is one way they can bring impact with capital. FOs with these intentions are quite explicit, but to add on to what already is, regular reports and communication to know their dollars are being put to good use is really what they’re looking for. Returns matter a little less.

And yes, finally, there are those who care about fees. For most families that we work with, the fees don’t seem to be the primary concern. But having chatted with a number of families out there, it is a concern that exists for some, not all. That said, it is a low-hanging excuse to pass on a fund-of-funds. 🙂

Photo by Y M on Unsplash

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