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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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.
At the risk of being an iconoclast and at the risk of offending people with the below, these are the tenets of venture capital today. You have been warned.
My investments will work out. They have to. Please.
Everyone else is dumber than I am.
My peers have died at the cross for me already. Their portfolios have died at the cross for me. The mega funds have died at the cross for me. I am absolved of my sins fueled by belief, hope, and my need to diligence the worthy.
VC is a power law business. I have yet to see the returns, not because they don’t exist, but because we are still in J-curve, at the very beginning of the hockey stick growth. I need only to believe in this truth as much as to leverage other people’s money to back true risk-on businesses.
The mega funds investing is all the signal I need from the powers above to tell me I’m on the right track. Yet, what I am doing is venture, not what they are doing.
Venture as an asset class is now too big to fail.
The gap between TVPI and DPI does not exist. It cannot. At the end of the day, moolah will be in the coolah. All paper marks will realize, collapsing the illusion of paper wealth into hard, undeniable absolute returns. Today, we are still pre-DPI. But believe that it will come. It’s a matter of when, not if.
Secondaries is the only answer I need. I guarantee someone else will want and buy what I have. For the price I have it at.
I was destined to do this the moment I wrote my first check. Whether it be in a friend or stranger, success or not, I knew I was meant for this. There is no other thing I’d rather do. Or not do.
Everyone who does not believe in me is foolish. Why can’t they see what I see? Are they blinded by only what’s in front of them? Are they blinded by the today that they can’t see my tomorrow?
Forgive me not, Father, for I have never sinned.
AI will replace every job. But never my job. Never me. I am above the collective consciousness.
Bible study sessions exist on Twitter/X. And I’m a regular attendee.
I repeat these prayers to myself thrice before sunrise. And thrice before the moon who shall be my witness.
There’s a Warren Buffett saying that relates to the world we live in now. “When a management with a reputation for brilliance tackles a business with a reputation for bad economics, it is the reputation of the business that remains intact.” We are in a world where the reputation of venture capital has not changed for the past 15 years. Brilliant people have died, are dying, and will continue to die at the cross.
An LP once told me something I’m inclined to agree with. “A lot of LPs should be VCs. A lot of VCs should be founders. A lot of founders should be employees.” The world doesn’t need more VCs. The world needs more builders.
All that to say, I’m still bullish and actively investing in venture, but it’s undeniable that there is a lot of fluff going on here.
Appreciate those for reading the above drafts and helping me make it more trigger-worthy. 🙂
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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.”
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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.
“When small men begin to cast big shadows, it means the sun is about to set.” — Lin Yutang
It’s been 10 years since I first stepped into venture. Yet still, while I know more, have met more people, and have experienced more, and when I look back, I pity the knowledge and experience I had a decade prior… yet despite all that, I know I have still so much work to do.
This essay was born from many conversations over the years, but especially so, in the past few months, where I’ve witnessed conversation after conversation that follows the theme of:
“Have you met X?”
“I have.”
“What do you think of X?”
“X feels far smarter online than X is in reality. After meeting X, where I anticipated so much, I was only let down.”
Never meet your heroes, they say.
In venture, we live in a world where the average VC brags more about “being a part of the journey” or “excited to support” a founder they backed than actually doing the work. It’s no wonder that 70% of VCs add no value (though 15% more add “negative value”). But it is far easier to say the part, look the part, than do the part. With SpaceX and OpenAI’s IPO today, Anthropic’s tomorrow, and Databricks, Anduril, who knows what, the day after, we will find many more VCs congratulating themselves, raising larger vehicles, and casting larger shadows.
In an unreleased interview with a GP I really admire, she told me an anecdote of a founder she knows well. “All of my early stage investors made out like bandits with my huge exit, and I never got a thank you. All I saw was them talk about how they discovered me and how they had such a big role to play in my success. But no one said, thank you for returning my fund 10 times over. And here’s a token of appreciation, whatever the appreciation is.” Which echoes the growing sentiment in the ecosystem.
And here’s my own self-reflection.
I hope that I cast no greater of a shadow than my beliefs, thoughts, and remarks would allow. And I hope still that I have the humility to cast a smaller shadow than I would ever be allowed to.
People measure shadows by the potential and impact someone may have. I have a friend who turned 30 recently. And when we sat down to chat, he told me that people were no longer telling him that he has potential. And one of his greatest fears is that people only see the person he is today for who he is today, and no longer the person he will be tomorrow. That pressure, more than anything, meant he was no longer “young.” I don’t think anyone ever loses their potential as a function of age. I have friends double my age, still learning every day, faster and more studious than people half of theirs. To me, that is still potential.
And here I hope that the shadow I’m capable of casting is underestimated than overestimated. But at least to myself, I hope I never underestimate myself.
“After I’m dead, I would much rather have men ask why I have no monument than why I have one.” — Cato
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.
“The question at Fund IV is, ‘Okay, you’ve proved that you’re a great firm builder. Congratulations, you’re raising Fund IV. Are you still a great investor?’” — Zach Ruchman
Zach Ruchman joined HB Wealth in 2025 as a Shareholder after working with WMS Partners since 2023. In his role as Managing Director, Private Markets, Zach leads the team responsible for research and due diligence of private market investment opportunities across a variety of asset classes, including private equity, growth equity, venture capital, private credit, infrastructure, and real assets.
Before joining HB Wealth, Zach was a Senior Vice President at RockCreek and a Vice President at BlackRock, where he led direct co-investment transactions as well as manager research for both primary and secondary commitments in the Americas, Europe, and Asia on behalf of both institutional and family office clients. He began his career as a consultant with Alvarez & Marsal. In this episode, we also talk about how he worked out of the National Democratic Institute’s DC office writing grants and tracking political regimes in the Middle East, including the Arab Spring.
In the community, Zach serves as a member of the finance committee for the Howard and Geraldine Polinger Family Foundation.
I’m also including my reactions to Zach’s comments here.
OUTLINE:
(00:00) Intro (03:04) When 9/11 entered Zach’s life (12:20) Interest in the Middle East (15:00) Returning to the US (17:49) What’s in the foreign service exam? (22:29) From pursuing the state department to consulting (25:39) Consulting to allocating (32:20) Business school and mentors (36:34) The ask (37:07) How Zach makes re-up decisions? (40:15) The difference between a Fund I and Fund IV (43:26) Alignment between senior and mid-level investors (45:33) Deal attribution at big VCs (46:40) Questions to ask to references to find deal attribution (49:12) Avoiding a reference’s scripted answer (52:14) Top 1% performers leaving organizations (53:45) The hardest Fund I to underwrite (1:00:57) Does radical transparency work? (1:06:15) “Private assets work best when they’re inefficient.” (1:09:20) Does AI change VC investing? (1:11:33) Sourcing that AI cannot do (1:14:26) Can AI write good memos? (1:19:11) Pattern vs exception recognition (1:25:03) An example of how a GP proved he worked hard (1:28:00) Best advice for action photography
“Consulting is almost like the liberal arts degree for the beginning of your career. You get to see a tremendous number of different business problems in a tremendous of different geographies. It’s like you have distribution requirements for your career.” — Zach Ruchman
“There are plenty of great investors that are not great firm builders.” — Zach Ruchman
“The question at Fund IV is, ‘Okay, you’ve proved that you’re a great firm builder. Congratulations, you’re raising Fund IV. Are you still a great investor?’” — Zach Ruchman
“If it was as easy as, ‘Hey GP, send your attribution spreadsheet,’ and I say, ‘Ok, great, that’s the attribution,’ my job would be so easy.” — Zach Ruchman
“If that person is an on-sheet reference for a spinout firm, the question then is, ‘Ok, you have a great relationship with this person, did you really do the deal with the person because you liked the person so much and you thought they were bringing something of value to you and that their money was a little greener than everyone else’s because there was a value-add or was it you really liked the name on the back side of the business card—the name of the firm?” — Zach Ruchman
“The hardest Fund I to underwrite is a brand new team. The easiest thing to underwrite is a team that lifts up together.” — Zach Ruchman
“Private assets work best when they’re inefficient.” — Zach Ruchman
“The more money you have going at a limited opportunity set, the more the perfectly priced that opportunity set will be.” — Zach Ruchman
“AI is only going to write what you tell it to write. So an AI memo is only going to be as thoughtful as the reasoning that you put into it, at least here in 2026.” — Zach Ruchman
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.
