The Religion of Venture Capital

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. โ€œWhen 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.โ€ 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. ๐Ÿ™‚

Photo by Aaron Burden on Unsplash


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.

GP EQ

conversation, eq, fundraising

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 โ€” 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.”

Photo by Priscilla Du Preez ๐Ÿ‡จ๐Ÿ‡ฆ on Unsplash


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.

Whac-A-Mole

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 shouldnโ€™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.

Photo by Yuheng Ouyang on Unsplash


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.

What is the Density of your Founder NPS? | El Pack w/ Charlotte Zhang | Superclusters

charlotte zhang

โ€œWeโ€™re going into a world where there will be an increase in inequality in terms of the haveโ€™s versus have-notโ€™s. And so if you are invested in some of the haveโ€™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.โ€ โ€” 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.

You can find Charlotte on her LinkedIn here:
LinkedIn: https://www.linkedin.com/in/charlotterzhang/

Listen to the episode onย Apple Podcastsย andย Spotify. You can alsoย watch the episode on YouTube here.

OUTLINE:

(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

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œIn 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.โ€ โ€” Charlotte Zhang

โ€œBecause incumbent brands create access flywheels, the most important thing for an emerging manager is having a clearly differentiated strategy. Otherwise, itโ€™s fighting an unwinnable war.โ€ โ€” Charlotte Zhang

โ€œInvestment strategies are simply financial products serving the market of what founders and management teams in businesses need.โ€ โ€” Charlotte Zhang

โ€œThe best founders will know who the best VCs are.โ€ โ€” Charlotte Zhang

โ€œItโ€™s all about the density of the NPS you have amongst the best talent. Of course, if they have a good experience with you, theyโ€™re more likely to refer others they think highly of to you. And thatโ€™s the reason why it becomes a leading indicator and therefore, a self-fulfilling prophecy as to who rises to the top.โ€ โ€” Charlotte Zhang

โ€œItโ€™s actually a higher signal to me if itโ€™s someone referring you that didnโ€™t take money from you.โ€ โ€” Charlotte Zhang

โ€œWhen weโ€™re conducting diligence as an LP, you should be looking under the rocks where you are more likely to find disproving evidence.โ€ โ€” Charlotte Zhang

โ€œIf [venture] does not produce any realized returns, how will it be self-funding? And how can you continue pacing sustainably into this asset class?โ€ โ€” Charlotte Zhang

โ€œWeโ€™re going into a world where there will be an increase in inequality in terms of the haveโ€™s versus have-notโ€™s. And so if you are invested in some of the haveโ€™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.โ€ โ€” Charlotte Zhang


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
For Superclusters After Hours: โ https://superclusterslp.substack.com/โ 
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP


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.

“You don’t have enough dopamine in your pitch!” | El Pack w/ Asher Siddiqui | Superclusters

asher siddiqui

โ€œHow 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.โ€ โ€” 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 worldโ€™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 firmsโ€”including Race Capital, Lumikai, Sukna Ventures, Zayn VC, and Humanrace Capitalโ€”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.

You can find Asher on his socials here:
LinkedIn: https://www.linkedin.com/in/ashersiddiqui/
X / Twitter: https://x.com/ashercdkey

Listen to the episode onย Apple Podcastsย andย Spotify. You can alsoย watch the episode on YouTube here.

OUTLINE:

(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

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œโ€œHappiness is amazing. Itโ€™s so amazing it doesnโ€™t matter if itโ€™s yours or not. A society grows great when old men plant trees the shade of which they know they will never sit in.โ€ โ€” from Ricky Gervaisโ€™ After Life

โ€œHow 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.โ€ โ€” Asher Siddiqui

โ€œThereโ€™s no point of perfect information, especially in venture, where you say โ€˜I have enough informationโ€™, this is the thesis, the timing is nowโ€”… No, thereโ€™s a lot of belief involved.โ€ โ€” Asher Siddiqui


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
For Superclusters After Hours: โ https://superclusterslp.substack.com/โ 
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP


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 Hardest Fund I to Underwrite | Zach Ruchman | Superclusters | S7E7

zach ruchman

โ€œThe question at Fund IV is, โ€˜Okay, youโ€™ve proved that youโ€™re a great firm builder. Congratulations, youโ€™re raising Fund IV. Are you still a great investor?โ€™โ€ โ€” 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.

You can find Zach on his socials here:
LinkedIn: https://www.linkedin.com/in/zruchman/
X / Twitter: https://x.com/zmrphoto

Listen to the episode on Apple Podcasts and Spotify. You can also watch the episode on YouTube here.

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

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œConsulting 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. Itโ€™s like you have distribution requirements for your career.โ€ โ€” Zach Ruchman

โ€œThere are plenty of great investors that are not great firm builders.โ€ โ€” Zach Ruchman

โ€œThe question at Fund IV is, โ€˜Okay, youโ€™ve proved that youโ€™re a great firm builder. Congratulations, youโ€™re raising Fund IV. Are you still a great investor?โ€™โ€ โ€” Zach Ruchman

โ€œIf it was as easy as, โ€˜Hey GP, send your attribution spreadsheet,โ€™ and I say, โ€˜Ok, great, thatโ€™s the attribution,โ€™ my job would be so easy.โ€ โ€” Zach Ruchman

โ€œIf that person is an on-sheet reference for a spinout firm, the question then is, โ€˜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 elseโ€™s because there was a value-add or was it you really liked the name on the back side of the business cardโ€”the name of the firm?โ€ โ€” Zach Ruchman

โ€œThe hardest Fund I to underwrite is a brand new team. The easiest thing to underwrite is a team that lifts up together.โ€ โ€” Zach Ruchman

โ€œPrivate assets work best when theyโ€™re inefficient.โ€ โ€” Zach Ruchman

โ€œThe more money you have going at a limited opportunity set, the more the perfectly priced that opportunity set will be.โ€ โ€” Zach Ruchman

โ€œAI 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.โ€ โ€” Zach Ruchman


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
For Superclusters After Hours: โ https://superclusterslp.substack.com/โ 
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP


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 Psychological Tax

burden, tax, headache

I was at an annual general meeting (AGM) the other week, and during one of the fireside chats, Scale’s Rory O’Driscoll said, “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 shouldnโ€™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.”

And I couldn’t stop thinking about that line.

Last week I also wrote a quick essay on things GPs say and think are gold, but LPs don’t. In which, I talked about win rates:

โ€œWe have a 90%+ win rate.โ€ Personally, I donโ€™t care. Some LPs do. But I know of a lot of institutions who have a dedicated venture team do not as well. Win rate can be engineered. There are funds that only offer verbal commitments with no term sheet that claim a very high win rate, so only the ones they offered a term sheet โ€œcount.โ€ Also, no one will ever say they have a 50% win rate (even if they do, I donโ€™t care as much as the other metrics that you could optimize for). No one will also say 100% win rate. And if they do, THAT is the thing you need to double click on and be wary of.

This past weekend, a friend heard a comment. “100% win rate means you’re not targeting the right founders.” Which is…… true. Many of the best founders, and especially true if they’re serial founders, are picky. They know exactly what they want, who they want. I give some grace to first-time founders who eventually become mainstay names because their early days are still full of rejections.

If you’re a VC with a specific thesis who has a stake in the ground, you’re probably not the VC that every founder wants. Only a very specific founder. But every so often you’ll come across a founder who you think will make it big, but they don’t see you as someone who can help or has the know-how to help them get to the next stage. And that’s okay. As Rory said, “the psychological burden of having an anti-portfolio is a privilege.” At least you’re in the right rooms. And as a VC, that’s the first half of the battle.

To come full circle, if you have a 90%+ win rate writing $500K or less checks, that’s to be expected. Assuming you know a founder beyond an acquaintance and you’re not an asshole, it’s hard to lose out on these opportunities, especially if you’re betting in non-obvious, illegible founders in the early days.

The larger your check, the more your win rate should technically decrease, and at some point, quite dramatically, where it no longer becomes a metric worth optimizing for.

And, if you ever have a 100% win rate, I dare say you have never had the privilege of the psychological tax of seeing multiple outlier founders and companies.

Photo by Nik Shuliahin ๐Ÿ’›๐Ÿ’™ on Unsplash


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.

What Your Lawyer Isn’t Telling You About LPA Terms | Apurva Mehta & JD Montgomery | Superclusters | S7PSE1

apurva mehta, jd montgomery

โ€œOur best GPs are talking to their founders all the time. And our best GP relationships, we talk to all the time.โ€ โ€” Apurva Mehta

โ€œIf you canโ€™t handle something going to zero, then you shouldnโ€™t do one.โ€ โ€” JD Montgomery

Apurva Mehta is the co-founding Managing Partner of Summit Peak Investments, a fund-of-funds that boasts a portfolio of both venture fund investments and direct investments, including the likes of Affirm, Anduril, Airtable, Opendoor, and Wish, just to name a few.

Prior to starting Summit Peak in 2018 with his co-founder, Patrick O’Connor, he previously served as Vice President and Deputy Chief Investment Officer for the Children’s Hospital Endowment Portfolio in Fort Worth, Texa. From 2008 to 2011, he was the Director of Portfolio Investments at The Juilliard School in New York City. Apurva began his career in investment consulting and investment banking at Citigroup and Lehman Brothers. He was recognized for his expertise when he was named to aiCIO Magazineโ€™s Top Forty Under Forty in 2012 and 2013 and honored as a Rising Star by Institutional Investor. He holds a BBA in Finance from The George Washington University.

You can find Apurva on his socials here:
LinkedIn: https://www.linkedin.com/in/apurvaamehta/

JD Montgomery leads the Family Office division at Canterbury Consulting and is a seasoned advisor with nearly four decades of experience serving prominent families with a focus on strategy, organization and measurement. Based in Newport Beach, he serves a select group of multi-generational families and helps them navigate the complexities of wealth, purpose, and legacy. Mr. Montgomery partners with his clients to help them optimize the allocation of their resources across generations. Over the years, Mr. Montgomery has developed a deep network of relationships in the venture capital industry. He has helped his clients gain meaningful exposure to venture funds and direct investments and develop relationships with leading innovators and investors globally. He is a Managing Director, shareholder, and board member at Canterbury Consulting. He graduated from Stanford University and holds the Chartered Alternative Investment Analyst (CAIA) designation.

You can find JD on his socials here:
LinkedIn: https://www.linkedin.com/in/jd-montgomery-6161341b/

Listen to the episode on Apple Podcasts and Spotify. You can also watch the episode on YouTube here.

OUTLINE:

(00:00) Intro
(01:53) How did this episode come to be?
(06:56) What do LPs get right/wrong with co-invests?
(12:06) GP best practices for co-investments
(14:35) How do you know a GP is capable of pre-empting a round?
(16:37) How often should GPs be talking to their portfolio founders?
(17:52) Why Apurva goes to AGMs
(18:17) How Apurva/JD stays in touch with GPs
(23:33) The ask
(24:01) Solo GPs
(31:42) Types of solo GPs who join multi-stage firms later
(34:32) What’s the skew in the benchmarking data?
(39:22) What lawyers don’t tell you about carveout capital in LPAs
(44:46) LPA terms that LPs redline
(45:44) Carry ratchets that LPs hate
(48:15) How higher fees impact IRR
(49:39) Outlandish fees on SPVs
(50:49) How much should a GP’s salary be?
(52:56) Cashless GP contributions
(53:59) Do $1T outcomes change venture math?
(59:17) Should private market investors be public market investors?
(1:04:30) What made Apurva nervous? What does he love?
(1:07:57) What does JD love?

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œIf you canโ€™t handle something going to zero, then you shouldnโ€™t do one.โ€ โ€” JD Montgomery

โ€œOur best GPs are talking to their founders all the time. And our best GP relationships, we talk to all the time.โ€ โ€” Apurva Mehta

โ€œIf Iโ€™m going to an AGM to learn about whatโ€™s going on in our portfolio, I am not doing my job.โ€ โ€” Apurva Mehta


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
For Superclusters After Hours: โ https://superclusterslp.substack.com/โ 
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP


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.

Pyrite

First off, this post has nothing to do with mining or minerals. If you’re curious as to why this post is called “Pyrite,” you’ll get it if you find out the nickname for pyrite.

Secondly, if I had a dollar for every time the below are said in an AGM, I’d be rich.

This was inspired after I read Brendan’s post from a few days ago. “Things we all already know that you can stop writing on LinkedIn about.”

As such, these are all the things we, as LPs, already have heard a million times at AGMs from GPs who believe these statements mean something real, but either (a) want to hear something different, or (b) is in many LPs’ eyes and ears, straight bullshit:

  • “This is the best time to be investing. AI is going to change the way we live, work and play.” We get it. We likely wouldn’t be at the AGM if we didn’t think so.
  • “These are the best entrepreneurs we’ve ever seen.” Or “Founders today are higher quality than we’ve ever seen before.” Or “Our top of funnel/(quality) deal flow is as robust as we’ve ever seen.” All to relate to “Entry valuation increases are to be expected because quality entrepreneurs and the growth they can achieve are unmatched in history. Historical prices shouldn’t be a tether.” Then should we anchor ourselves on anything you initially pitched LPs? Is the promise we invested in the same as the fund that currently exists? What are exceptions to the rule and when do exceptions become the norm? Assuming you did invest in higher priced rounds, what is the venture math necessary to 5X the fund? What are the possible exit paths for that exit to be meaningful to you? Citing Chris Douvos’ old blogpost here that elucidates that.
  • “The portfolio is really trending in the right direction.” We want to hear the lowlights on top of the highlights. Not everything is sunshine and rainbows. So let’s not pretend it is. Also let’s not forget to talk about the performance of older funds that may or may not have zombie companies. Are you proactive with new marks?
  • “Trillion dollar IPOs are here.” Twitter and LinkedIn and any major publication has already informed us of such.
  • Venture arrogance score (Shoutout to Josh Kopelman for the initial nomenclature) for big funds”, and/or “small emerging managers outperform” and/or “venture math is broken” and/or “multi-stage funds have raised 50%+ of this year’s dollars.” Yes to all of this, but with a caveat. The dispersion of returns at the emerging manager level is far higher. Higher risk of ruin, and higher chance you return less than 1X your fund size. As an asset class to “index,” emerging managers are realistically a bad bet. Moreover with emerging managers, in the words of a large institutional LP who told me this, “we invest in venture because we like taking company-level risk, but not fund-level risk.” All the above statements are technically true, but I’ve also seen so many emerging managers “forget” to move their warehoused deals into the fund, call more capital than they promised their LPs back-to-back, drift from their strategy, move their final close date 5+ times, leak sensitive LP information to their intern/associate, get kicked out of their own fund by a fund platform, breakup the partnership mid-fund, and the list goes on. I’m not saying established funds are immune to this, but it is important for an LP and a GP to be aware of the whole package that’s getting pitched. Usually most institutional LPs in emerging managers are already well aware of the above, which is why to then, LPAC seats matter to get on top of the matters.
  • “We believe the company is growing into its valuation.” More often than not, that’s not the case. This is just a version of sugarcoating really high last round valuation (LRV) marks. This usually indicates a flat or down round at best, the next raise, assuming the company can raise.
  • “We consistently get allocation in competitive rounds.” Probably. But also introduces the question of what does “competitive” mean. Does your definition of competition and the LP’s definition match up? AND is competitive or hot always good? AND are you outsourcing your decision-making to other firms? Unfortunately, the answer to the last question is often yes for a lot of emerging managers.
  • “We beat other investors and at lower prices.” Probably again. But is it adverse selection? There’s a massive graveyard of companies that raise once and never get traction in any direction (i.e. customers, investors, etc.). So rather than saying that, show us why said companies are generational talent and ideas. Who else did you talk to and have a chance to invest in before you picked this one? Is their revenue growing in a direction that suggests it isn’t adverse selection? Admittedly, this one you have to do more work to show most LPs why. Otherwise, doubt will always linger.
  • “We have a strong pipeline of LP interest ahead of our next fundraise.” Unfortunately, no one says the inverse. And so while it may be true for you (time will tell), no one can verify that statement outside of wired commitments, unless they dig deep.
  • “We have a 90%+ win rate.” Personally, I don’t care. Some LPs do. But I know of a lot of institutions who have a dedicated venture team do not as well. Win rate can be engineered. There are funds that only offer verbal commitments with no term sheet that claim a very high win rate, so only the ones they offered a term sheet “count.” Also, no one will ever say they have a 50% win rate (even if they do, I don’t care as much as the other metrics that you could optimize for). No one will also say 100% win rate. And if they do, THAT is the thing you need to double click on and be wary of.

And finally because of all the above, this is why junior people go to AGMs, as a box to check, as opposed to senior partners and CIOs. The same is true for Demo Days these days too.

Thanks to Chris (who actually first inspired this post ages ago on the pod), Asher, Youngrok, Dave, and a few other LPs who chose to stay anonymous for keeping me grounded on this post and making this post more robust. And to Brendan who re-inspired me to finish this one.

Photo by Caleb Jack on Unsplash


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 Value Add Differs in PE vs VC | Julia Rees Toader | Superclusters | S7E6

julia rees toader, princap

“In private equity, some of the older tricks about just picking on more leverage are not going to work as well now because rates are higher. We need to have more focus on operational improvement and margin expansion. And in venture, youโ€™re not expected to have good margins.โ€ โ€” Julia Rees Toader

Julia Rees Toader is the Founding Partner of PrinCap, an independent investment portfolio strategy firm working with institutions and individuals on manager selection, asset allocation, and strategic advisory. Prior to PrinCap, she was the Head of Portfolio Strategy and Head of Relationship Management at Heritage Holdings, a multi-family office. Before Heritage, Julia was the head of Portfolio Strategy at Goldman Sachs Asset Management ($3Tr assets under supervision). She and her team advised sovereign wealth funds, pensions, financial advisory firms, private banks, and other long-term asset owners on asset allocation. She studied mechanical engineering and computer science at Princeton University and is a CFA charterholder. Before Goldman Sachs, she worked on M&A and business development for an early-stage medical device biotech firm.

You can find Julia on her socials here:
LinkedIn: https://www.linkedin.com/in/julia-rees-toader-cfa-22871030/

Listen to the episode onย Apple Podcastsย andย Spotify. You can alsoย watch the episode on YouTube here.

OUTLINE:

(00:00) Intro
(01:38) A ‘happy accident’ at 16
(04:03) Julia’s first startup experience
(06:32) Why did Julia join Goldman Sachs?
(07:30) When did Julia’s appreciation for finance start?
(08:05) Conversations around the Rees and Toader dinner table
(09:48) Finance vs mechanical engineering
(13:26) On exceptional talent
(15:18) How to keep a cool head when you’re successful
(20:19) Do small emerging managers outperform?
(22:27) How do you know if a GP is founder-friendly?
(23:39) The bad pitch meeting
(25:00) Value adds in PE vs VC
(29:49) Difference between PE vs VC portfolio construction models
(31:19) Timelines to return in PE and VC
(33:17) Secondaries
(34:34) The ethics of continuation vehicles
(36:07) The subscription ask
(36:40) Are all secondaries created equal?
(38:30) What is 10+1+1?
(40:32) Hedge funds looking like private market funds
(41:16) What do you do when you have $3B?
(44:43) What is home country bias?
(46:40) How do you know you’re overweighted on allocation?
(47:15) The endowment effect in secondaries
(48:32) Leaderless investment committee sessions
(49:52) The merits of GP stakes
(54:10) Why private credit is interesting
(56:21) The duration of GP stakes
(57:36) The duration of hedge fund GP stakes
(58:11) How much GP stake is worth it?
(1:00:33) Hedge funds: How much is a good GP stake?
(1:02:00) How much is the max an LP wants to own of a hedge fund?
(1:03:12) Tax structuring is another form of alpha
(1:06:52) Cheetos Pelotazos
(1:09:15) Advice to women in finance
(1:12:28) Post-credit scene: Age of Empires, Starcraft, and Zelda

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œIn private equity, you want to have that strong value creation playbook. It used to be that you could do quite well doing mostly financial engineering, roll-ups, that kind of thing. That still works, but I think a lot of the money in the next part of the cycle is going to come from improving the margins or increasing EBITDA, so making operational improvements. So private equity, some of the older tricks about just picking on more leverage are not going to work as well now because rates are higher. We need to have more focus on operational improvement and margin expansion. And in venture, youโ€™re not expected to have good margins.โ€ โ€” Julia Rees Toader

โ€œThe providers of liquidity always get paid.โ€ โ€” Julia Rees Toader

โ€œLPs and GPs both donโ€™t want to be forced sellers.โ€ โ€” Julia Rees Toader

โ€œHome country bias is the tendency of people to overallocate to their home market.โ€ โ€” Julia Rees Toader

โ€œThe endowment effect, which is the idea that if you own something, you think itโ€™s more valuable than what anyone else is willing to pay for it.โ€ โ€” Julia Rees Toader

โ€œTax structuring is another form of alpha.โ€ โ€” Julia Rees Toader

โ€œAlphaโ€™s three things: information asymmetry, access, and, actually, taxes.โ€ โ€” Vijen Patel


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
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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.