When she complains about the dishes…

dishes

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

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


One of the most memorable pieces of relationship advice Iโ€™ve gotten is that line. โ€œWhen she complains about the dishes, itโ€™s not about the dishes.โ€

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

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

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

When she complains about you being too early, itโ€™s that she never had conviction over the deal. When she says you need more traction (track record), itโ€™s because she couldnโ€™t see why you would see and win the most interesting deals in your space. What you say has yet to be proven by what you did. So, the underwriting will start now for what you will do. She doesnโ€™t trust you can execute against what you promised. Youโ€™re either talking a big game (using superlatives that feel disingenuous) and/or you create a feeling of naivete. Be assured that the best allocators will be keeping track of what you promised before. Even if you, as a GP, rewrite your Docsend pitch deck. Admittedly, still, most wonโ€™t.

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

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

When she complains that there isnโ€™t enough capital to left to deploy, itโ€™s the fact you arenโ€™t good enough to be an exception that would help her raise her next vehicle or to get board approval. Excluding institutions (including family offices) who own their own pool of evergreen capital, anyone who has to ask other stakeholders for more capital to invest has at least 20-30% left to deploy when they go out to raise their next vehicle. The primary motivator for the remainder of capital are people or opportunities that best highlight an allocatorโ€™s promise to their stakeholders. Fund-of-funds promise access. That means either a multi-million dollar allocation in Anthropic or an individual (usually spinout, but sometimes highly reputable founder/operator) whoโ€™s been early in generational opportunities. Others, like multi-family offices, depending on their mandate, either promise access or their ability to pick great pickers, which means 5X+ DPI in 5 years in a prior fund is extraordinarily exciting. Realized IRR or DPI matter a lot.

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

When she doesnโ€™t complain at all and just disappears from your life, she didnโ€™t feel safe with you to give you the feedback you ought to hear. She feared your reaction, or at least the expectation of your reaction. You never provided the safe space she needed. Itโ€™s likely because of how you talked about others. The more judgmental you are about others, the more sheโ€™ll thinkโ€ฆ if things go awry, will you say the same about me behind my back? Can you even handle any amount of criticism?

Thereโ€™s another great line on communication, but also on relationships by writer and poet Khalil Gibran. โ€œBetween what is said and not meant, and what is meant and not said, most of love is lost.โ€

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

Photo by Scott Umstattd 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.

The Danger of the Value-Add Investor

umbrella, valuable, value add

I’ve been a believer for a long time that our jobs as LPs (especially if weโ€™re on the LPAC) is to be the parent at the playground. I donโ€™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, thatโ€™s when we step in as the parent.

We see those โ€œdangerous maneuversโ€ in fund updates, at AGMs, in LP reach outs, in LPA terms, or hell, in regular conversations. I donโ€™t give unsolicited feedback. Just my personal rule. The only exception I make to that rule is if I see something youโ€™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:

  1. “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.
  2. “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.”

Photo by J W on Unsplash


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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.

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 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.

Who Should NEVER Start a VC Fund? | Sam Huleatt | Superclusters | S7E3

sam huleatt

โ€œLower barriers to entry doesnโ€™t mean higher probabilities of success.โ€ โ€” Sam Huleatt

Sam Huleatt is the co-founder of The Side Letter, a platform driving network-based research for capital allocators. Prior to The Side Letter, he created and ran the The LP Institute at VC Lab, as well as let On Deck Angels at On Deck. Moreover, he’s a serial founder, active angel investor in over 35 companies, and an active allocator in emerging fund managers, including the likes of Notation Capital, Orange Fund, Inuka Capital, Asylum Capital, and more.

You can find Sam on his socials here:
LinkedIn: https://www.linkedin.com/in/samhuleatt/
X / Twitter: https://x.com/samhuleatt

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

OUTLINE:

[00:00] Intro
[01:34] Sam’s childhood
[03:24] The most persistent myth about Sam he never bothered to correct
[05:47] Bottom-up vs top-down investor
[13:37] Can career VCs develop empathy for the founder?
[18:43] Traits of someone who should definitely start a fund
[26:45] Traits of someone who should NEVER start a fund
[28:09] Air of inevitability
[33:44] Why was Outlander VC inevitable?
[36:11] Where should 60% of your Fund I capital come from?
[41:47] Starting a VC fund is hard
[44:46] Do LPs like GP accelerators?
[51:35] Top 3 considerations for first-time LPs
[58:03] How many GPs should 1st-time LPs meet?
[1:01:06] Governing law of VC: Adverse selection
[1:04:40] Incentive alignment on fees
[1:06:36] Terms in LPAs vs side letters
[1:11:16] What is The Side Letter?

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œA career VC has a lot more experience having been on boards. And because of that, because theyโ€™ve been a career VC, theyโ€™ve seen more companies operating at scale and the issues that come into play in those cases, whereas operators-turned-GPs often have a narrow aperture because theyโ€™ve spent most of their career at one or two companies. On the one hand, the operator-GP obviously has a lot of empathy for founders because theyโ€™ve been that founder, but they probably havenโ€™t experienced all of the difficult issues that come up as companies scale across lots of different environments. Career VCs have.โ€ โ€” Sam Huleatt

โ€œThe best investors have an air of inevitability. Itโ€™s not asking for permission or doing something because itโ€™s perceived to be high status.โ€ โ€” Sam Huleatt

โ€œLower barriers to entry doesnโ€™t mean higher probabilities of success.โ€ โ€” Sam Huleatt

โ€œMost people, after starting a fund, should assume that 60% of that Fund Iโ€”you should raise that from first-degree connectionsโ€”people you already know. It may not be easy, but if you donโ€™t have a network thatโ€™s large enough or has those resources, you either need to reconsider your fund target size or maybe you need to spend more time building your network before you start to go out and do that raise.โ€ โ€” Sam Huleatt

โ€œIf you donโ€™t have an edge going into [a GP] accelerator, youโ€™re certainly not going to find an edge in the accelerator.โ€ โ€” Sam Huleatt

โ€œWhy do the best GPs in the world want you to be on the cap table? A lot of people forget that a key aspect of venture is not just picking, but being picked. Thatโ€™s true for LPs and itโ€™s true for GPs.โ€ โ€” Sam Huleatt

If you somehow made it to the bottom of these show notes, I’m also trying a new experiment where I write my reactions to the episode on my second blog, Superclusters After Hours. For Sam’s episode, you can find my reactions here.


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
Follow Superclusters on TikTok: https://www.tiktok.com/@super.clusters
Follow Superclusters on Instagram: https://instagram.com/super.clusters


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.

“I Write-Off Every Sourcing Slide” | Alex Felman | Superclusters | S7E2

alex felman

โ€œThe game you play as youโ€™re building a reputation becomes a different game than when you have a reputation. And I tend to find, from an LPโ€™s perspective, when youโ€™re building reputation, thatโ€™s actually when you deliver the most value.โ€ โ€” Alex Felman

Alex Felman is an entrepreneurial and family office professional. For over 10 years, as a second-generation member, he has run his own family office, Felman Family Office, and works with family offices around the world through his family’s multifamily group, MSF Capital Advisors. Using his expertise in Molecular Toxicology and Bio-entrepreneurship (B.A from University of California -Berkeley, MBA from Copenhagen Business School), he advises them in biotechnology, healthcare, and other futuristic tech industries with the goal of maintaining long-term wealth through innovation. He regularly speaks at family office and private wealth events on topics such as tech investment, manager selection, generation and succession issues, rising generation trends, and more.

He has used his experience within the family office industry and 20 year background as an educator to create Exponential U, a family office education program designed to help families become multigenerationally sustainable. His proprietary L3 framework (Learn, Leverage, Legacy) allows the holistic development of family members to ensure a smooth leadership transition.

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

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

OUTLINE:

[00:00] Intro
[04:36] The ‘tastemaker’ for family offices
[05:54] Exploration vs discipline
[08:15] The hero’s journey in investing
[09:49] The life line
[13:39] Building and having reputation
[16:06] Risk appetites for asset owners & allocators
[18:44] Why won’t an institution invest in me?
[19:50] The quiet thing LPs don’t talk about
[25:15] When did Alex get involved with his family office?
[29:09] Writing off sourcing slides
[35:33] Different flavors of “sourcing from YC”
[38:41] Emerging GPs are “investments-as-a-service”
[40:08] Fund power law is greater than startups’
[43:44] Emotional value of investing in funds
[44:45] Most VC funds are scams!
[50:01] Optimistic cynic
[51:43] Reminders today about the good ol’ days
[54:17] Late stage capitalism
[59:10] Post-credit scene: Dave Chappelle and podcasts

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œEvery great conversation dances on the line of your understanding. You dance between both sides of the line and try to find out where what you know and what they know intersect and end. Good conversation is like play.โ€ โ€” Alex Felman

โ€œWith my background from the family offices, I almost believe that most family offices moving forward will need their own personal tastemaker or sommelier. Someone whoโ€™s curating the world specifically for the needs of that family.โ€ โ€” Alex Felman

โ€œPeople get into trouble when theyโ€™re using the wrong tool or trying to do something for a different purpose. For example, Iโ€™m going to try to do discovery when Iโ€™m in my routine. Ok, youโ€™re probably running into problems. Or routinizing my discovery. Those two things are in conflict with each other.โ€ โ€” Alex Felman

โ€œOne of the things people always forgetโ€”… What they remember from the heroโ€™s journey is adventure, and we fight the dragon, and we get the treasure. But at the end of the heroโ€™s journey, youโ€™re supposed to bring that back to your community. And youโ€™re supposed to forward it to your community. And youโ€™re supposed to make your community better from the dragons and the treasure that you fight or find. Most people often leave off that last part. And I actually think that last part is extremely important.โ€ โ€” Alex Felman

โ€œThe game you play as youโ€™re building a reputation becomes a different game than when you have a reputation. And I tend to find, from an LPโ€™s perspective, when youโ€™re building reputation, thatโ€™s actually when you deliver the most value.โ€ โ€” Alex Felman

โ€œIf you have a family office where youโ€™ve actually outsourced it, your employee is more of an allocator than an owner. And in that case, that allocator is often making decisions to save their own job. Or to ensure that they continue to have a job.โ€ โ€” Alex Felman

โ€œWhat I find is slightly sad is that ultimately because of security and comfort reasons, things like peopleโ€™s pensions which should be more secure, are actually, in my opinion, taking riskier bets. And bets that will lead to worse outcomes.โ€ โ€” Alex Felman

โ€œI believe that the amount of due diligence you do doesnโ€™t matter depending on the deal size. So letโ€™s say theyโ€™re writing five $100 million checks compared to 100 $5 million checks, that is literally 20 times the amount of work. So even if theyโ€™ll get a better return on that 100 $5 [million checks], on a realistic level, it forces them to play certain types of games.โ€ โ€” Alex Felman

โ€œWith at least funds on a standard two and twenty, somewhere around $75-100 million fund size is where the incentives shift from being carry-oriented to management-fee oriented. Once you get larger than that, then it actually becomes more incentivized for the fund managers to build up their funds than the actual returns itself.โ€ โ€” Alex Felman

โ€œI would argue that power laws apply even more to funds than to startups.โ€ โ€” Alex Felman

โ€œThe intersection of venture as a product or service meets venture as a job career. And there are a lot of fund managers who see venture as a job career and essentially want to use it as a way to get a paycheck. And because of that, theyโ€™re going to put out a fairly boilerplate fund.โ€ โ€” Alex Felman

โ€œMany venture funds are basically scams. I believe itโ€™s a scam if you knowingly sell something you know you canโ€™t deliver on. And the dirty secret in venture is if you purely look at venture from a financial point of view, most fund managers know they cannot hit their targets and yet they still sell that promise anyway. And I think that starts to become kind of scammy.โ€ โ€” Alex Felman

If you somehow made it to the bottom of these show notes, I’m also trying a new experiment where I write my reactions to the episode on my second blog, Superclusters After Hours. For Alex’s episode, you can find my reactions here.


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
Follow Superclusters on TikTok: https://www.tiktok.com/@super.clusters
Follow Superclusters on Instagram: https://instagram.com/super.clusters


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.

(Not) Relationship Advice

relationships, biking

Earlier this year, when catching up with a friend and talking about love, he shared his greatest relationship advice. “You want to marry someone who believes the world happens because of them, not to them.” And it really stuck with me. Both he and I are people who have big dreams. That in order to make our dreams happen we need every oar rowing in the same direction. That includes the people we surround ourselves with. More than anyone else, our romantic partner is likely the one we spend the MOST time with. But that in itself is a slight digression.

In a somewhat parallel sequence of events, at the end of last year, I had the opportunity to join a much, much larger shop. And while I ended up choosing not to join, the primary question I was asking myself was: If I were successful here, would I be successful in spite or because of the institution? The truth was from an outsider’s perspective, maybe even personally, it’d be really hard to tell.

Now why do I share the above? And where the hell am I going with all of this? What does love have to do with career opportunities?

So… this won’t be my most graceful transition between thoughts, but in my head, they all orbit the same genre.

One of the questions I used to ask LPs during my time in investor relations was: “What was the last investment you made that didn’t work out? Without naming names, what happened?”

And there are two reasons I ask that:

  1. Oftentimes, knowing what an LP doesn’t or won’t ever invest in again is more telling than asking them what they do invest in. LPs are, by definition, generalist. And under that premise, they technically invest in “everything,” so you’ll end up getting very broad answers, especially if they cover more than one asset class.
  2. Do they describe an investment that didn’t work out with active or passive verbs? Did it happen to them? Or do they own up/exhibit agency over their own decisions? Are they arbiters of their own destiny? “I made this investment decision, learned, and this is what I won’t do in the future. Or will still continue to do.” is different from… “This mishap happened to me. How could I have known? It is what it is. It’s not my fault. It was out of my control. It was someone else’s decision.”

For the latter point, people who don’t seem to be able to own up to the decision will likely not be your greatest champions if you’re an emerging manager. If at all. To them, life happens to them. They can’t control it. They have a narrative they keep telling themselves that they have no power. Some might be true. But these folks rarely stick their neck out for you.

By default, most emerging managers look less than pretty. A million reasons (most of which likely true) of what could go wrong. And it’s actually in the best interest of a capital allocator’s career and income that they stick their neck out for risky bets. Many institutions don’t compensate their team based on outlier performance. So incentives won’t be aligned. But to borrow an adage of Jobs, “the people who are crazy enough to think they can change the world, are the ones who do.” And at the very minimum, they have to believe they can change their own world.

When things are non-obviousโ€”from a returns perspective or strategy or anything elseโ€”you need people who can and will invest courageously and own that decision.

Photo by Everton Vila 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.