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?
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
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.
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?
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?
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.
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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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.
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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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.
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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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.
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.”
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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.
A conversation with an LP reminded me of this recently. Can we trust a GP’s word that they’re a good picker if they can’t assess how likely an LP is to commit?
I’ve had multiple conversations with GPs where they tell me XXX and YYY are excited to come in the fund, and they just need more time to close their fundraise or for their process. Then the same XXX and YYY LPs ghost these GPs for months on end. For me, that’s enough for me to question their level of commitment, but not having been in those conversations firsthand, I can’t speak to the actual incentives. Sometimes, I actually know XXX and YYY LPs well enough to pick up the phone and dial them right away and ask them what’s up. Which I do. Only to hear from them and they say they had passed already.
Now I don’t know what actually goes on between those two parties. What’s said and what’s not said. There are many LPs out there who give very soft “no’s.” In hopes to not offend, they imply it’s a “no.” There are also LPs who explicitly say it’s a “yes” ONLY IF ZZZ happens. Given the current market, most of the time, ZZZ doesn’t happen, which becomes an easy out for the LP. The LP’s felt like they’ve delivered the “no.” The GP is still hanging onto the hope the LP likes them enough to break the rule. And then, there are many GPs who have selective hearing loss.
Nevertheless, there are multiple instances of this. And it’s not my job to point fingers to any party other than elucidate that this exists in our world.
That said, even if an LP doesn’t explicitly say “no”, there should be enough breadcrumbs to point to whether someone is a pass. Probably harder to know if they’re a “yes.” But there’s definitely writing on the walls if it’s a pass. And it’s almost always better to assume an LP is an out than an in if there’s hesitation.
The outstanding question for someone like me or any of my friends who I’ve had this conversation with is… is this indicative of a GP’s EQ when talking to founders? Is this GP more prone to rewriting history and facts? Is there a massive perception bias here and is the GP living through rose-tinted lens?
Richard Feynman has this great line. “The first principle is that you must not fool yourself — and you are the easiest person to fool.”
And I’ve also had this conversation with another GPs a few weeks back, and I said, “You’re either lying to me or you’re lying to yourself. One is worse than the other. But neither gives me a reason to back you.”
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
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.
One of the questions that seem to come up every so often, whether it’s when I’m on a podcast or a fireside chat or just in conversation, is: Between sourcing, picking, and winning, which one do you think is the most important that emerging managers have?
The cop-out answer is always: They need all three. Or, they’re all important. Which is theoretically true. One in isolation is really hard to pull off ’cause then you need to account for sheer dumb luck (hope is never a strategy). And while everyone is subject to their own answer, I’m a big believer that the lead domino between the trifecta is sourcing. If you never see it, how do you even pick or win it?
We can talk about how you’d theoretically and systematically pick the best founders or how your value-add is something that is something truly valuable to your investments, but if you never have the opportunity to interact with a generational founder, I don’t care how smart you are. Or how well-connected you are. Or how experienced you are. I don’t care if you’re the world’s greatest X if no one’s heard of you or thinks of you when they or someone close to them starts a company.
Venture is a game of outliers. (I feel like a broken record at this point writing and saying this.) And I would much rather a GP see and miss generational founders again and again (and well, learn each time they do) than to have only seen one their entire life. Obviously, both are better than not having met any ever. You don’t know what quality looks like if you’ve never seen quality before they became obvious. No amount of books you’ve read or podcasts you’ve listened to will help you with that. I would rather you have a large anti-portfolio than build one for the first time as you’re starting your first fund. And in that anti-portfolio, it’s a lot of “I didn’t pick it” or “I didn’t win it” or “I didn’t even know I wanted to be an investor yet.” Yet despite all of that, I’ve chosen to stay in touch with these generational talents and they still value my presence in their orbit.
If you’ve only met one generational founder in your life before, I need to figure out if your network and sourcing channels would allow you to see another in the next 3-4 years (or whatever your deployment period is). And that when you see it, you’ll know that that is the one. But every generational founder looks different from the rest. So if you’ve only seen one in the past, how will I know if you have both the pattern recognition and the exception recognition to pick the next?
For those who have seen one or less generational founders in their lives, I have to bet that you somehow can “use the Force.”
That on the off-chance you do find one, can I trust your intuition to recognize it AND win it?
On the flip side, there’s this game that many of us grew up with. Whac-A-Mole. It’s an arcade game that has a series of moles hiding in holes. The goal is to whack as many moles as you can as they pop their heads up. Venture investing is similar. Each mole is a generational founder. That you may miss “whacking” many a generational founder, but as long as you keep seeing them, and as long as you keep trying to pick them, you’ll eventually hit one. And if you’re lucky, more than one. But in order to see multiple generational founders, you need the cards to be stacked in your favor. The ideal venture manager should be playing a constant game of Whac-A-Mole, as opposed to using the force. Although, damn, being a Luke Skywalker sounds a hell of a lot cooler than playing an arcade game.
To pull a line from Scale’s Rory O’Driscoll that I wrote about in a previous post, “Having to deal with the psychological burden of having an anti-portfolio is a privilege. If you never have the psychological tax of passing on multiple generational deals, you shouldn’t be in venture. Passing on 20 great companies out of 40 great companies you see is always more preferable than investing in 2 great companies after seeing 40 average companies.”
Then there’s the question of whether our definition of generational founders even match up. Does your definition lead you to find founders who will exit at $1B+ outcomes? $100B+ outcomes? Or $100M outcomes? But a topic for another day.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
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.
“We’re going into a world where there will be an increase in inequality in terms of the have’s versus have-not’s. And so if you are invested in some of the have’s, I would actually bet on their acceleration of value aggregation in the later stages of scaling which is why I, personally, think a winning strategy is to hold onto them for as long as possible.” — Charlotte Zhang
Charlotte Zhang from Inatai Foundation is back! And if you’ve tuned into her first episode on Superclusters, you’ll know exactly why. Charlotte has been one of my favorite guests on the podcast, marrying both her profound ability for deep analysis with strong framework-oriented assessments. You might remember her 4 P’s to underwriting every manager from our prior episode.
Naturally I had to have her back for an El Pack episode to answer your questions on how to build a venture capital fund. We bring on 3 GPs at VC funds to ask 3 different questions.
99VC’s Lisa Yu asks about what LPs look for in Fund I’s beyond track record.
Escape Velocity’s Mahesh Ramakrishnan asks about recycling and what happens when you have 30% of your fund size as distributions in the first few years of the fund.
Founder Embassy’s Helena Gagern asks about investing in AI frontier labs where the first round of financing already puts the company at $400M+ in valuation. And also, how do you communicate to LPs that you have an “exceptionalism” bucket to invest out of?
As the director of investments at Inatai Foundation, Charlotte Zhang oversees the selection of external investment managers, conducts portfolio research, and helps to institutionalize processes, tools, and resources. She previously served as a senior associate at ICONIQ Capital and, before that, Medley Partners. When not working, you can find her globetrotting (18 countries and counting), writing a Yelp review about the best bite in town, or cuddling up with a book and her two adorable cats.
(00:00) Intro (01:04) What’s new in Charlotte’s life? (04:06) LPs Charlotte would love to meet (05:41) Who is Lisa and 99VC? (09:31) What qualities does Charlotte look for beyond track record? (14:55) How does a GP know if they have a differentiated strategy? (15:49) Charlotte’s pet peeve (17:29) The bottoms up exercise of building a fund strategy (18:00) Consistency of execution (20:05) The highest level of signal you can get from a founder reference (22:18) The ask (22:51) Who is better at bowling: Mahesh or David? (24:44) Who is Mahesh and Escape Velocity? (25:20) Why is Escape Velocity spelled as EV^3? (27:10) What happens when you have 30% DPI in the first 2 years of your fund? (30:19) Does early DPI matter more in Fund I than Fund III? (33:26) Should you sell secondaries at the Series B as a pre-seed/seed GP? (37:34) Venture is under siege for no DPI (38:18) Would Charlotte rather have 4X in 10 years or 7X in 15 years? (39:42) Have’s and have-not’s (40:35) Who is Helena and Founder Embassy? (44:45) What is Charlotte’s reaction when a pre-seed GP invests in a $400M post valuation? (49:23) How do the best GPs communicate betting off-thesis? (50:44) How many GPs have an “exceptionalism” bucket to invest out of? (55:56) How much underwriting goes into a GP breaking the rules? (58:10) “A-players are obvious” but what isn’t? (1:00:38) Charlotte’s last piece of advice for LPs (1:03:43) Charlotte’s last piece of advice for GPs (1:07:18) Why you should talk about the anti-portfolio (1:09:33) David’s favorite moment from Charlotte’s previous episode
“In venture capital, although the top quartile of emerging managers outperforms the established funds. On average, you would actually be better off investing in established funds than in an emerging manager because the dispersion of returns is so much wider in emerging managers.” — Charlotte Zhang
“Because incumbent brands create access flywheels, the most important thing for an emerging manager is having a clearly differentiated strategy. Otherwise, it’s fighting an unwinnable war.” — Charlotte Zhang
“Investment strategies are simply financial products serving the market of what founders and management teams in businesses need.” — Charlotte Zhang
“The best founders will know who the best VCs are.” — Charlotte Zhang
“It’s all about the density of the NPS you have amongst the best talent. Of course, if they have a good experience with you, they’re more likely to refer others they think highly of to you. And that’s the reason why it becomes a leading indicator and therefore, a self-fulfilling prophecy as to who rises to the top.” — Charlotte Zhang
“It’s actually a higher signal to me if it’s someone referring you that didn’t take money from you.” — Charlotte Zhang
“When we’re conducting diligence as an LP, you should be looking under the rocks where you are more likely to find disproving evidence.” — Charlotte Zhang
“If [venture] does not produce any realized returns, how will it be self-funding? And how can you continue pacing sustainably into this asset class?” — Charlotte Zhang
“We’re going into a world where there will be an increase in inequality in terms of the have’s versus have-not’s. And so if you are invested in some of the have’s, I would actually bet on their acceleration of value aggregation in the later stages of scaling which is why I, personally, think a winning strategy is to hold onto them for as long as possible.” — Charlotte Zhang
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
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.
“How you modulate a good story is by inserting dopamine, oxytocin, serotonin, and endorphins at the right times to be able to deliver that story so that the person listening to that story can form an opinion.” — Asher Siddiqui
Asher Siddiqui from the Song Family Office joins me on El Pack to answer your questions on how to build a venture capital fund. We bring on 3 GPs at VC funds to ask 3 different questions.
Inuka Capital’s Gautam Shewakramani asks about what GPs typically overshare and under-share when they’re pitching an LP. As well as how an LP identifies if a GP has great sourcing if they’re a generalist fund.
Unshackled Venture’s Manan Mehta asks if VC is still only one asset class. Is early stage now a combination of discovery and validation capital?
Keymaker VC’s Tim Wang asks what do most LPs overvalue in GPs.
Asher Siddiqui is a global tech investor, M&A dealmaker, and venture fund builder with over 25 years of hands-on experience across venture capital, entrepreneurship, and more than $15B in executed M&A transactions.
He began his career as a software engineer and entrepreneur in the US and UK before spending a decade leading M&A and corporate venture at Etisalat Group (now e& Group), one of the world’s largest listed TMT investment groups. There, he led acquisitions, exits, and strategic transactions across multiple continents.
In 2016, Asher joined the global leadership team at 500 Startups in San Francisco, helping scale the platform to $2B+ AUM, with a portfolio that includes 35+ unicorns and 160+ centaurs.
Since then, he has helped launch and scale several institutional VC firms—including Race Capital, Lumikai, Sukna Ventures, Zayn VC, and Humanrace Capital—and serves on the advisory boards of funds such as FootPrint Coalition Ventures, Merus Capital, and The Treasury.
To date, Asher has made 100+ venture investments (both direct and LP), raised hundreds of millions in LP commitments, mentored hundreds of emerging VC managers globally, and advised countless founders.
(00:00) Intro (02:09) The DOSE framework for underwriting pitches (04:19) Asher’s new role (05:38) Who is Gautam and Inuka Capital? (09:19) What do most GPs overshare and undershare on? (15:19) How does Asher differentiate sourcing ability in generalist funds? (20:01) The first date analogy (22:38) What emotions do each of DOSE represent? (27:23) Too much dopamine, not enough endorphins (30:02) Who is Manan and Unshackled Ventures? (31:33) Unshackled’s most recent big win (32:46) Discovery capital vs validation capital (33:31) Is venture still only one asset class? (43:29) The Song Family Office portfolio construction (51:41) Asher’s stance on reserves (55:00) Why it makes sense to go to zero AGMs (56:23) The ask (57:27) Who is Tim and Keymaker VC? (58:45) What do most LPs overvalue in GPs? (1:04:40) A new way to share the team’s personality on the deck? (1:08:09) Asher’s last piece of advice (1:14:57) David’s favorite moment of Asher in S5
““Happiness is amazing. It’s so amazing it doesn’t matter if it’s yours or not. A society grows great when old men plant trees the shade of which they know they will never sit in.” — from Ricky Gervais’ After Life
“How you modulate [a good story] is by inserting dopamine, oxytocin, serotonin, and endorphins at the right times to be able to deliver that story so that the person listening to that story can form an opinion.” — Asher Siddiqui
“There’s no point of perfect information, especially in venture, where you say ‘I have enough information’, this is the thesis, the timing is now—… No, there’s a lot of belief involved.” — Asher Siddiqui
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
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.
