Tag: questions

Posted on

Good Misses and Bad Hits

basketball shot, swoosh

The espresso shot:

  • What are the essential elements of a “good” VC fund strategy vs. “lucky”?
  • What elements can you control and what can you not?
  • How long does it take to develop “skill” and can you speed it up w/ (intentional) practice?

Anyone can shoot a three-pointer every once in a while.

Steph Curry is undeniably one of the best shooters of our time. If not, of all time. Even if you don’t watch ball, one can’t help but appreciate what a marksman Steph is. In case you haven’t, just look at the clip below of his shots during the 2024 Olympics.

From the 2024 Olympics

As the Under Armour commercial with Michael Phelps once put it, “it’s what you do in the dark that puts you in the light.” For Steph, it’s the metaphoric 10,000 hours taking, making, and missing shots. For the uninitiated, what might be most fascinating is that not all shots are created equal, specifically… not all misses are created equal.

There was a piece back in 2021 by Mark Medina where he wrote, “If the ball failed to drop through the middle of the rim, Curry and Payne simply counted that attempt as a missed shot.” Even if he missed, the difference between missing by a wide margin versus hitting the rim mattered. The difference between hitting the front of the rim versus the backboard or the back rim mattered. The former meant you were more likely to make the shot after the a bounce than the other. Not all misses are created equal.

Anyone can shoot a 3-pointer. With enough tries. But not everyone can shoot them as consistently as Steph can.

The same holds for investing. Many people, by sheer luck, can find themselves invested in a unicorn. But not everyone can do it repeatedly across vintages. It’s the difference between a single outperforming fund and an enduring firm.

The former isn’t bad. Quite good actually. But it also takes awareness and discipline to know that it may be a once-in-a-lifetime thing. The latter takes work. Lots of it. And the ability to compound excellence.

When one is off, how much are you off? What are the variables that led you to miss? What variables are within your control? And what aren’t? Of those that are, how consistent can you maintain control over those variables?

As such, let me break down a few things that you can control as a GP.

Deal Flow

Are you seeing enough deals? Are you seeing enough GREAT deals? Do you find yourself struggling in certain quarters to find great deals or do you find yourself struggling to choose among the surplus of amazing deals that are already in your inbox? Simply, are you struggling against starvation or indigestion? It’s important to be intellectually honest here, at least to yourself. I know there’s the game of smokes and mirrors that GPs play with LPs when fundraising, but as the Richard Feynman line goes, “The first principle is that you must not fool yourself—and you are the easiest person to fool.”

Value Add

Whereas deal flow is about what companies you see, value add is more about how you win deals. Why and how do you attract the world’s best entrepreneurs to work with you? In a world where the job of a VC is to sell money – in other words, is my dollar greener or is another VC’s dollar greener – you need to answer a simple question: Why does another VC fund need to exist?

What can you provide a founder that no other, or at least, very few other, investors can

While there are many investors out there who say “founders just like me” or “founders share their most vulnerable moments with me”, it’s extremely hard for an LP to underwrite. And what an LP cannot grasp their head around means you’ll disappear into obscurity. The file that sits in the back of the cabinet. You’ll exist, and an LP may even like you, but never enough for them to get to conviction. And to a founder, especially when they’ve previously “made it”, already, you will fall into obsolescence because your value-add will be a commodity at scale. Note the term “at scale.” Yes, you’ll still be able to win deals on personality with your immediate network, and opportunistically with founders that you occasionally click with. But can you do it for the three best deals that come to your desk every quarter for at least the next four years? If you’re building an institutional firm, for the next 20+ years. Even harder to do, when you’re considering thousands of firms are coming out of the woodwork every year. Also, an institutional LP sees at least a few hundred per year.

For starters, I recommend checking out Dave’s piece on what it means to help a company and how it impacts your brand and perception.

Portfolio Size

Deal flow is all about is your aperture wide enough. Are you capturing enough light? Portfolio size is all about how grainy the footage is. With the resolution you opt for, are you capturing enough of the details that could produce a high definition portfolio? In venture, a portfolio of five is on the smaller side. And unless you’re a proven picker, and are able to help your companies meaningfully or you’re in private equity, as a Fund I, you might want to consider a larger portfolio. It’s not uncommon to see portfolios at 30-40 in Fund I that scale down in subsequent funds once the GPs are able to recognize good from great from amazing.

I will also note, with too big of a portfolio, you end up under optimizing returns. As Jay Rongjie Wang once said, ““The reason why we diversify is to improve return per unit of risk taken.” At the same time, “bear in mind, every fund that you add to your portfolio, you’re reducing your upside as well. And that is something a lot of people don’t keep in mind.”

Moonfire Ventures did a study in 2023 and found that “the probability of returning less than 1x the fund decreases as the size of your portfolio grows, and gets close to zero when your portfolio exceeds 200 companies.” That said, “it’s almost impossible to 10x a fund with more than 110 companies in your portfolio.”

While there’s no one right answer in the never-ending diversified versus concentrated debate, nevertheless, it’s worth doing the work on how size and the number of winners in your portfolio impact returns.

Valuations and marks

First off, how are you measuring your marks? Marc Andreessen explains the concept of marks far better than I can. So not to do the point injustice, I’m just going to link his piece here.

Separately, the earliest proxies of portfolio success happens to revolve around valuations and markups, but to make it more granular, “valuation” really comes down to two things:

  1. Graduation rates
  2. Pro rata / follow-on investments

Graduation rates

When your graduation rates between stages fall below 30%, do you know why? What kinds of founders in your portfolio fail to raise their following round? What kinds of founders graduate to the next stage but not the one after that? Are you deeply familiar with the top reasons founders in your portfolio close up shop or are unable to raise their next round? What are the greatest hesitations downstream investors have when they say no? Is it the same between the seed to Series A and the A to B?

Pro rata / follow-on investments

Of your greatest winners, are you owning enough that an exit here will be deeply meaningful for your portfolio returns. As downstream investors come in, naturally dilution occurs. But owning 5% of a unicorn on exit is 5X better than owning 1% of a unicorn. For a $10M fund, it’s the difference for a single investment 1X-ing your fund and 5X-ing it.

When you lose out on your follow-on investment opportunities, what are the most common reasons you didn’t capitalize? Capital constraints? Conviction or said uglier, buyer’s remorse? Overemphasis on metrics? Lack of information rights?

Then when your winners become more obvious in the late stages and pre-IPO stages, it’s helpful to revisit some of these earlier decisions to help you course-correct in the future.

I will note with the current market, not only are the deal sizes larger (i.e. single round unicorns, in other words, a unicorn is minted after just one round of financing), there are also more opportunities to exit the portfolio than ever before. While M&A is restricted by antitrust laws, and IPOs are limited by overall investor sentiment, there have been a lot of secondary options for early stage investors as well. But that’s likely a blogpost for another day.

In closing

To sum it all up… when you miss, how far do you miss?

Obviously, it’s impossible to control all the variables. You cannot control market dynamics. As Lord Toranaga says in the show Shogun when asked “How does it feel to shape the wind to your will?”, he says “I don’t control the wind. I only study it.” You can’t control the wind, but you can choose which sails to raise, when you raise them, and which direction they point to. Similarly, you also can’t completely control which portfolio companies hit their milestones and raise follow-on capital. For that matter, you also can’t control cofounder splits, founders losing motivation, companies running out of runway, lawsuits from competitors, and so on.

But there are a select few things that you can control and that will change the destiny of your fund. To extend the basketball analogy from the beginning a bit further, you can’t change how tall you are. But you can improve your shooting. You can choose to be a shooter or a passer. You can choose the types of shots you take — 3-pointers, mid-range, and/or dunks. In the venture world, it’s the same.

The choice. Or, things you can change easily:

  1. Industry vertical
  2. Stage
  3. Valuation
  4. Portfolio size
  5. Check size
  6. Follow-on investments

The drills. Or, things you can improve with practice:

  1. Deal flow – both quantity and quality
  2. The kinds of deals you pick
  3. Value add – Does your value-add improve over time? As you grow your network? As you have more shots on goal?
  4. The deals you win – Can you convey your value-add efficiently?

And then, the game itself. The things that are much harder to influence:

  1. Graduation rates
  2. Downstream dilution
  3. Exit outcomes
  4. The market and black swan events themselves

Venture is a game where the feedback cycles are long. To get better at a game, you need reps. And you need fast feedback loops. It’s foolhardy to wait till fund term and DPI to then evaluate your skill. It’s for that reason many investors fail. They fail slowly. While not as fast of a feedback loop as basketball and sports, where success is measured in minutes, if not seconds – where the small details matter – you don’t have to wait a decade to realize if you’re good at the game or not in venture. You have years. Two to three  What kinds of companies resonate with the market? What kinds of founders and companies hit $10M ARR? In addition, what are the most common areas that founders need help with? And what kinds of companies are interesting to follow-on capital?

Do note there will always be outliers. StepStone recently came out with a report. Less than 50% of top quartile funds at Year 5 stay there by Year 10. And only 3.7% of bottom-quartile funds make it to the top over a decade. Early success is not always indicative of long-term success. But as a VC, even though we make bets on outliers, as a fund manager, do not bet that you will be the outlier. Stay consistent, especially if you’re looking to build an institutional firm.

One of my favorite Steph Curry clips is when he finds a dead spot on the court. He has such ball control mastery that he knows exactly when his technique fails and when there are forces beyond his control that fail him.

Source: ESPN

Cover photo by Martí Sierra on Unsplash

Huge thanks to Dave McClure for inspiring the topic of this post and also for the revisions.

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.

Posted on

Referencing Excellence

magnifying glass, excellence

Recently, I’ve had a lot of conversations with LPs and GPs on excellence. Can someone who has never seen and experienced excellence capable of recognizing it? The context here is that we’re seeing a lot of emerging managers come out of the woodwork. Many of which don’t come from the same classically celebrated institutions that the world is used to seeing. And even if they were, they were in a much later vintage. For instance, a Google employee who joined in 2024 is very different from a Google employee in 2003.

And there seem to be two schools of thought:

  1. No. Only someone who is fortunate enough to be around excellent people in an excellent environment can recognize excellence in others. Because they know just how much one needs to do to get there. Excellence recognizes excellence. So there’s this defaulting to logos and brands that are known concentrations of excellence. Unicorns. Top institutions. Olympians. Delta Force. Green Beret. Three Michelin-starred restaurants.
  2. Yes. But someone must constantly stretch their own definition of excellence and reset their standards each time they experience something more than their most excellent. The rose growing in concrete. The rate of iteration and growth matters for more. Or as Aram Verdiyan once put it to me, “distance travelled.”

Quite possibly, a chicken and egg problem. Do excellent environments come first or people who are born excellent and subsequently create the environment around themselves?

It’s a question many investors try to answer. The lowest hanging fruit is the outsourcing of excellence recognition to know excellent institutions and known excellent investors. The ex-Sequoia spinout. Ex-KKR. Ex-Palantir. First engineer at Uber. Or hell, they’re backed by Benchmark. Or anchored by PRINCO.

It’s lazy thinking. The same is true for VC investors and LP investors. As emerging manager LPs (and pre-seed investors), we’re paid to do the work. Not paid to have others do the work for us. We’re paid to understand the first principles of excellent environments. To dig where no others are willing to dig.

To use an extreme example, a basketball court can make Kobe Bryant an A-player, but Thomas Keller look like a C-player. Similarly, a kitchen will make Thomas Keller an A-player, but Ariana Huffington a C-player. Environments matter.

When assessing environments and doing references, that’s something that you need to be aware of. What does the underlying environment need to have to make the person you’re diligencing an A-player? Is the game they have willingly chosen to play and knowledgeable enough to play have the optimal environment that will allow them to be an A-player? Is the institution they’re building themselves conducive to elicit the A out of the individual?

Ideally, is there evidence prior to the founding of their own firm that has allowed this player to shine? Why or why not?

Did they have a manager that pushed them to excel? Was there a culture that allowed them to shine? Were they given the trust and resources to thrive?

References

And so, that leads us to references. I want to preface with two comments first.

One, as an investor, you will NEVER get to 100% conviction on an investment. It’s one of the few superlatives I ever use. Yes, you will never. Unless you are the person themselves, you will never understand 100% about a person. And naturally, you will never get to 100% conviction because there will always be an asymmetry of information.

Two, so… your goal should not be to get to total symmetry of information, nor 100% conviction. Instead, your goal is to understand enough about an opportunity so that you can sufficiently de-risk the portfolio. What that means is that when you meet a fund manager (or a founder, for that matter) across 1-2 meetings, you write down all the risk factors you can think of about the investment. You can call it elephants in the room, or red or yellow flags. Tomato. Tomahto.

Then, rank them all. Yes, every single one. From most important to least important. Then, somewhere on that list — and yes, this is deeply subjective — you draw a line. A line that defines your comfort level with an investment. The minimum number of risks you can tolerate before making an investment decision. For some, say those investing in early stage venture or in Fund I or II managers, that minimum number will be pretty high. For others, those whose job is to stay rich, not get rich, that minimum tolerance will be quite low. And that’s okay.

There’s a great line my partner once told me. You like, because; you love, despite. In many ways, the art of investing in a risky asset class is understanding your tolerance. What are you willing to love, despite?

The purpose of diligence, thereinafter, is to de-risk as many of your outstanding questions till you are ready to pull the trigger.

In regards to references, before you go further in this blogpost, I would highly recommend Graham Duncan’s essay “What’s going on here, with this human?” My buddy, Sam, also a brilliant investor, was the person who first shared it with me. And I’m a firm believer that this essay should be in everyone’s reference starter pack. Whether you’re an LP diligencing GPs. Or a VC doing references on founders. Or a hiring manager looking to hire your next team member.

Okay, let’s get numbers out of the way. Depending on the volume of investments you have to make, the numbers will vary. The general consensus is that one or two is too little, especially if it’s a senior hire or a major investment. Kelli Fontaine’s 40 reference calls may also be on the more extreme side of things. Anecdotally, it seems most investors I know make between five and ten reference calls. Again, not a hard nor fast rule.

That said, there is often no incentive for someone to tell a stranger bad things about someone who supported them for a long time. It’s why most LPs fail to get honest references because they haven’t established rapport and trust with a founder over time. Oftentimes, even in the moment. So, the general rule of thumb is that you need to keep making reference calls until you get a dissenting opinion. Sometimes, that’s the third call. Other times, is the 23rd call. If you’ve done all the reference calls, and you still haven’t heard from others why you shouldn’t invest, then you haven’t done enough (or done it right).

A self-proclaimed coffee snob once told me the best coffee shops are rated three out of five stars. “Barely any 2-4 stars. But a lot of 5-stars and a lot of 1-stars. The latter complaining about the baristas or owner being mean.” I’m not sure it’s the best analogy, but the way I think about references is I’m trying to get to the ultimate 3-star review. One that can highlight all the things that make that person great, but also understand the risks, the in’s and out’s, of working with said person.

For me, great references require trust and delivery.

  1. Establishing trust and rapport. What you share with me will never find its way back to the person I am calling about.
  2. Is the reference themselves legit? Is this person the best in the world at what they do?
  3. How well does this reference know said person? Have they seen this person at both their highs and lows? At their best and at their worst.
  4. The finer details, the possible risks, and how have they mitigated them in the past.

I will also note that off-list references are usually much more powerful than on-list references. Especially if they don’t know you’re doing diligence on the person you’re doing diligence on. But on-list references are useful to understand who the GP keeps around themselves. After all, you are the average of the people you hang out with most. As the one doing the reference checks, I try to get to a quick answer of whether I think the reference themselves is world-class or not.

While I don’t necessarily have a template or a default list of questions I ask every reference, I do have a few that I love revisiting to set the stage.

Also, the paradox of sharing the questions I ask is simply that I may never be able to use these questions again in the future. That said, references are defined by the follow-up questions. Rarely, if ever, on the initial question. There’s only so much you can glean from the pre-rehearsed version.

So, in good faith, here are a few:

Does the reference know them well?

  • If I told you this person was [X], how surprised would you be? Now there are two scenarios with what I say in [X]. The first is I pick a career that is the obvious “next step” if I were to only look at the resume. Oftentimes, if a person’s been an engineer their entire life, the next step would be being an engineering executive, rather than starting a fund. So, I often discount those who wouldn’t find it surprising. Those that say it is surprising, I ask why. The second scenario is where I pick a job that based on what I know about the GP in conversations is one I think best suits their skillset (that’s not running their own fund), and see how people react. The rationale as to why it’s surprising or not, again, is what’s interesting, not the initial “surprising/not surprising” answer itself.
  • If you were invited to this person’s wedding, which table do you think you’d be sitting at?
  • Have you ever met their spouse? How would you describe their spouse?

Understanding their strengths and weaknesses

  • Who’s the best person in the world at X? Pick a strength that you think the person you’re doing a reference on has. See what the reference says. Ask why the person they thought of first is the best person in the world at it. If the reference doesn’t mention the GP I’m diligencing, then I stop to consider why.
  • What are three adjectives you would use to describe your sibling? I’ve written about my rationale for this question before, so I won’t elaborate too much here. Simply, that when most people describe someone else, they describe the other person comparatively to themselves. If I say Sarah is smart, I believe Sarah is smarter than I am. Or… if I say Billy is curious, I believe Billy is more curious than I am.
  • If I said that this person joined a new company, knowing nothing about this new company, what would your first reaction be?
    • Congratulate this person on joining!
    • Do a quick Google or LinkedIn search about the company.
    • As an angel, consider investing in the company (again, knowing nothing else)
  • How would you rate this person with regards to X, out of 10? What would get this person to a 10? Out of curiosity, who’s a 10 in your mind?
  • If you were to hire someone under this person, what qualities would you look for?
  • If you were to reach out to this person, what do you typically reach out about?
  • I hate surprises. Is there something I should know now about this person so that I won’t be surprised later?
  • Of all the media, gossip, and stories that surround this person, what would you say is the most misunderstood piece of lore about this person?

Photo by Shane Aldendorff 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.

Posted on

Request for LPs (2025)

question, request, ask, raising hand

A capital allocator is someone who balances the humility that they are not the world’s best at something (or might never be) with the deep belief in the long-term potential of an asset class (even if that means they will play a less active role in the future of that asset class).

As always, the last holiday period was a time for introspection and reflection. Many of the conversations I had were around request for startups (RFS) with VCs and request for funds (RFF) with LPs. Many of the latter focused on spaces and problems that individuals and family offices personally care a lot about.

In the essence of putting my vote for all the below, I’m going to phrase them as questions and pontifications rather than statements. Since I don’t have the capital to invest in such organizations, but also it is highly likely that these organizations need no external sources of capital. In fact, a number of the family offices I’ve conversed with have enough capital where they no longer use external bank providers for lending, but borrow and invest only within the families.

Is there a world where the LP is the sourcing engine for the GPs in their portfolio?

Like Deep Checks, but catalyzed by a single institution with large brand appeal. The problem is two-fold:

  1. Most LPs are not good at identifying great deals at the pre-seed and seed stage.
  2. Many LPs love co-investment opportunities. They’ve historically invested in brand-name funds expecting such opportunities, but largely evidenced in the 2020 to early 2022 hype cycle, most got no calls from their VCs at all. So, they’ve moved towards emerging managers who don’t have reserves to cash in on their top deal flow.

If an LP is willing to be a sourcing engine which complements their portfolio funds’ deal flow, that LP will have a chance to build (a) conviction earlier, and (b) build relationships with founders earlier. And in the sourcing/picking/winning framework, outsource the picking element to people who have more refined tastes built upon years of being boots on the ground.

Of course, said LP cannot enforce that GP invests in a certain type of company in which its sourcing engine brings in. That’ll defeat the purpose of investing in GPs in the first place, as well as diversifying risk.

Is there a world where a deeply networked LP leverages their network to support the underlying startup portfolio?

There are a number of fund-of-funds in the world who offer their geographical connections to help a portfolio fund’s startup grow in their respective market, but I’ve seen comparatively few, if any, LPs who offer their deep networks as advisors/mentors to portfolio founders.

For the most part, a VC is likely to better connected to tech talent, executives and founders. But quite a few family offices and endowments have their own deeply entrenched networks. Endowments have alumni networks. Family offices, depending on their source of wealth, are well-connected in the industry that created their wealth. Luxury brands. Oil and gas, as well as renewable energy. Infrastructure. CPG. Pharmaceutical drugs. Transportation. And the list goes on.

In other words, the LP would help a VC win deals based on their expansive combined networks. And sometimes the best advice a founder can get is not from another founder or VC, but someone tangential to the ecosystem who has seen the world from a birds eye view.

I’ve written before that there are three kinds of mentors: peer, tactical, and strategic. And you need all three.

  1. Peer: Someone with similar level of experience as you do
  2. Tactical: Someone who’s 2-5 years out and who can check your blind side
  3. Strategic: Someone who’s attained success in a particular field and is often 10+ years out from where you are. They offer the macro and big-picture perspective, and help you define long-term goals.

Founders often have their peers already. And if not that, there are a number of communities, forums, and groups out there where founders can exchange notes with each other. Many VCs often bring their founders together to co-mingle as well in annual or quarterly get-togethers.

VCs themselves often act as tactical mentors, and given how their portfolios grow also have access to a plethora of tactical mentors for any given company.

LPs with their large networks of people who run multi-billion dollar enterprises (often not tech), many of whom achieved financial success independently, have access to people who could be strategic mentors for founders in their fund-of-fund’s underlying portfolio.

Request for Funds of Funds?

This isn’t a particularly traditional fund model or fund-of-funds model, but nevertheless would be an interesting product for asset owners. Namely large institutions who are looking for product diversification and who have little to no short-term and medium-term liquidity needs. Large single family offices, pensions, and potentially some endowments and foundations.

Is there a smaller product that focuses on vintage diversification from both an entry and exit perspective?

Most investors focus on entry vintage diversification, not as much for exits. Some LPs do, to make sure they have liquidity in every vintage. While I’ve seen only a small, small number of funds and fund-of-funds do this, I wonder if this is something that is more interesting to a broader customer base of LPs.

Of those I’ve seen so far:

  • Crypto funds that hold both token-based assets and equity-based assets. The token-based ones are expected to deliver DPI within years 4-8. The equity-based assets are expected to deliver DPI within years 8-12.
  • Funds-of-funds that hold multiple asset classes within a single LP entity. Secondaries for 3-6-year time horizons. Buyouts for 5-8-year time horizons. And venture capital for 8-12 year time horizons. Some also hold venture debt assets and cryptocurrency themselves.
  • Large multi-stage billion-dollar plus VC funds that have a suite of product offerings for LPs.

There are many emerging LPs and LPs who see VC as an access class who can’t write massive checks, but need to hedge their bets when writing into a speculative asset class.

While I’m still working to collect more data on this, I do wonder. In modern history, market cycles happen every 8-12 years. Venture funds exist on 10-12 year time horizons. Theoretically, that means if you’re investing in the least expensive entry windows, you’re also existing in the lowest revenue multiple windows. And if you’re investing in the most expensive vintages, you’re also existing in the great markets. Which effectively means, the delta between “buying low” and “selling high” are roughly the same no matter which markets your entry point is.

The data seems to suggest that so far, but the publicly available datasets (i.e. Pitchbook) have heavy survivorship bias. There’s no incentive for funds that fizzle out midway or near the end to report their metrics. Carta is really interesting, but their datasets aren’t robust till after 2017.

As an allocator, it just means you just need to be in every vintage. It makes me wonder if it really matters to be investing in down or up markets. Probably not. As the sages who have invested through multiple cycles tell me. Though I wonder if underwriting venture funds to 15 years changes anything on the DPI front across multiple vintages.

Photo by Felicia Buitenwerf 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.

Posted on

Talent Networks are your Greatest Asset | Adam Marchick | Superclusters | S4E9

adam marchick

“When investing in funds, you are investing in a blind pool of human potential.” – Adam Marchick

Over the past twenty years, Adam Marchick has had unique experiences as a founder, general partner (GP), and limited partner (LP). Most recently, Adam managed the venture capital portfolio at Emory’s endowment, a $2 billion portfolio within the $10 billion endowment. Prior to Emory, Adam spent ten years building two companies, the most recent being Alpine.AI, which was acquired by Headspace. Simultaneously, Adam was a Sequoia Scout and built an angel portfolio of over 25 companies. Adam was a direct investor at Menlo Ventures and Bain Capital Ventures, sourcing and supporting companies including Carbonite (IPO), Rent The Runway (IPO), Rapid7 (IPO), Archer (M&A), and AeroScout (M&A). He started his career in engineering and product roles at Facebook, Oracle, and startups.

You can find Adam on his socials here:
X / Twitter: https://x.com/adammStanford
LinkedIn: https://www.linkedin.com/in/adammarchick/

And huge thanks to this episode’s sponsor, Alchemist Accelerator: https://alchemistaccelerator.com/superclusters

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[03:14] Who is Kathy Ku?
[06:20] Lesson from Sheryl Sandberg
[06:39] Lesson from Justin Osofsky
[07:46] How Facebook became the proving grounds for Adam
[09:26] The cultural pillars of great organizations
[10:40] When to push forward and when to slow down
[12:39] Adam’s first investment: Dell
[14:20] What did Adam do on Day 1 when he first became an LP
[17:00] Emory’s co-investment criteria
[20:02] Private equity co-invests vs venture co-invests
[21:15] Teaser into Akkadian’s strategy
[23:03] Underwriting blind pools of human potential
[29:03] Why does Adam look at 10 antiportfolio companies when doing diligence?
[32:11] What excites and scares Adam about VC
[35:36] Engineering serendipity
[37:52] Where is voice technology going?
[39:45] How does Adam think about maintaining relationships?
[43:20] Thank you to Alchemist Accelerator for sponsoring!
[44:20] If you enjoyed this season finale, it would mean a lot if you could share it with 1 other person who you think would love it!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“What’s so freeing is when you can bring your personality to work. It’s so much less cognitive load when you can be yourself.” – Sheryl Sandberg’s advice to Adam Marchick

“Take your work seriously, not yourself.” – Adam Marchick

“Be really transparent, and even document and share your co-investment criteria.” – Mike Dauber, Sunil Dhaliwal’s advice to Adam Marchick

“For an endowment doing co-invests, you should never squint.” – Adam Marchick

“When investing in funds, you are investing in a blind pool of human potential.” – Adam Marchick

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.

Posted on

Stress and Ambition

stress, founder stress

“The thing about working with self-motivated people and driven people, on their worst day, they are pushing themselves very hard and your job is to reduce the stress in that conversation.”

It’s something Nakul Mandan from Audacious said in a Superclusters episode earlier in Season 4. And a line that’s been gnawing at me for the past few weeks. Particularly, “your job is to reduce the stress in that conversation.” So it got me thinking… Are the entrepreneurs I back stressed (enough)?

I know what you’re thinking. But before you come at me with pitchforks and torches, here me out. If you get to the end of this essay and still feel as strongly, feel free to take a swing at me.

First off, let me define some terms in the above question. An “entrepreneur” is someone who starts something that doesn’t exist in the world already. To me, that is a startup founder, a local restaurant, an emerging fund manager, and so on. I use this term pretty liberally. “Enough” is in moderation. A balance of feeling the pressure and urgency, but not enough to make one go insane. By definition, entrepreneurs — people who dare challenge the world and create something that hasn’t existed before — are ambitious. And ambitious, action-oriented doers are, to Nakul’s point, often hard on themselves. So everything in moderation. As a friend once told me, if you’re doing anything ambitious, a third of your days will be epic. A third will be okay. And a third will absolutely suck. As long as your days feel like that proportionally, you’re on the right track.

So… are the entrepreneurs I back stressed (enough)?

Let’s start with no. Are they the underdog still, pre-product-market fit, stagnating, losing market share, and/or in a crisis?

If not, carry on. It’s okay to not be stressed all the time. In fact, it’s probably not helpful to be stressed all the time.

If so — that they are the underdogs, stagnating or in a crisis — AND they’re not feeling stressed, I do wonder from time to time. And I’d be lying if some part of me didn’t feel buyer’s remorse. Because that means one of three things:

  1. They’ve lost their ability to care. About the product. The market. The team. Or simply, their own ambition. That’s the worst.
  2. Conversely, they don’t feel comfortable enough to be vulnerable with me. And that, in part, not to sugarcoat things, is because of me.
  3. They never cared enough or were ambitious enough in the first place. And that’s something I have to take back to the drawing board so that I learn the next time around.

Nevertheless, regardless of which of the three, it warrants a conversation. A difficult one. One where I try to understand their current motivations, what’s changed. If their motivations still hold true, then I, in Danny Meyer’s words, add “constant, gentle pressure.” For those curious, Chapter 9 of his book. Nevertheless, my job is to give them the activation energy to hopefully get them back on track.

If things change, great. I eventually go back to the first question. Are the entrepreneurs stressed? If not, then I let them on a few things:

  1. I’ll spend less time time with them to prioritize the rest of my portfolio.
  2. If they have any of the money left, they can keep the money. FYI, if it wasn’t my personal angel money, but someone else’s capital (of which I’m a fiduciary), depending on how much they have left, it may lead to a different conclusion. But in general, I view it as a write-off.
  3. Wish them the best of luck in their next chapter.
  4. If they feel the fire burning again (for good reason), they should let me know. And I’m happy to have another conversation.

Now… what happens if the entrepreneurs are stressed. Then I try to figure out if it’s anxiety or stress. Let me define.

Anxiety is caused by things you cannot control. For instance, the market. Other people you cannot control. Or black swan events. Stress, on the other hand, is caused by things you can control. Your own mistakes. Mistakes made by people you hired. Volume of work that needs to be done. Procrastination. Mistakes that can be actively mitigated. For instance, missing the deadline for a quarterly report. Missing payroll due to insufficient funds. Layoffs. Bad performance. Media, publicity, and perception. Something Danny Meyer calls, “writing a great last chapter.” As Danny Meyer puts it, “the worst mistake is not to figure out some way to end up in a better place after having made a mistake.”

If it’s anxiety, my role is to calm the founders. Be the mental support they need. Help them see the bigger picture. Build contingency plans.

If it’s stress, my role is to help them build an action plan. Help get key decision-makers and doers in the same room. Get the founders in front of advisors who can help them think through key considerations and check their blind side (assuming it’s not me. Most of the time it isn’t.). Of course, you need to timebox “thinking” time. There’s a great saying. “There are no right choices; only choices we make right.”

And finally, help the entrepreneurs execute the plan. Sometimes, that requires getting my hands dirty. And that’s what I’m here for. To increase the metabolism of the organization. Or at the very minimum, leadership. Stress is often caused by indigestion of tasks that need to be done.

Alas, the job of an investor, given we’re not in the driver’s seat, that we don’t always have complete information, is to reduce the stress of the founder when we have that conversation. More often than not, ambitious founders are hard enough on themselves.

Photo by Francisco Moreno 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.

Posted on

The Dao of Investing in VC Funds | Jay Rongjie Wang | Superclusters | S4E8

jay rongjie wang, jay wang

“The first layer is setting up your own strategy. The second layer is portfolio construction. How do you do your portfolio construction based on the strategy you set out to do? And then manager selection comes last. Within the portfolio construction target, how do you pick managers that fit that ‘mandate?’” – Jay Rongjie Wang

Jay Rongjie Wang is the founding Chief Investment Officer of Primitiva Global, where she runs a family-backed Multi-asset Strategy. She also works extensively with emerging VC managers, and sits on the Selection Committee of Bridge Funding Global.

Jay’s background uniquely combines software engineering (at the world’s largest fintech platform) and institutional investing (at top funds including Fidelity and Sequoia), as well as general management (3x executive in tech startups). Jay has lived in 5 different countries across 9 major cities, giving her a global perspective.

Jay obtained her B.A and M.Sci in Physics from Cambridge University and M.B.A from INSEAD. In 2023 she was listed as an Entrepreneurial Pioneer Under 35 by Hurun Wealth.

You can find Jay on her socials here:
LinkedIn: https://www.linkedin.com/in/wangrongjie/

And huge thanks to this episode’s sponsor, Alchemist Accelerator: https://alchemistaccelerator.com/superclusters

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[04:12] Life atop a Daoist mountain
[10:27] Qigong and tai chi
[12:21] What is dao?
[19:18] The weapon that Jay specializes in
[21:08] Why did Jay leave the Daoist temple?
[24:24] The motivations behind Jay’s career shifts
[30:05] The difference between underwriting a VC fund and a fund-of-funds
[33:08] How does Jay get to know a fund manager?
[36:31] The 3-layer process for building an allocation strategy
[38:01] Picking the initial asset class
[45:29] How much Jay allocates to venture
[48:43] What does “reasonably diversified” mean?
[49:15] Figuring out the portfolio construction model
[54:59] At what point do you stop maximizing for portfolio returns?
[56:57] How Jay calculates a 200X target return on direct investments
[57:53] Data on returns as a function of portfolio size
[1:01:42] The biggest challenge once you’ve picked your strategy
[1:04:40] Selecting the right fund managers
[1:14:17] The difference between guqin and piano
[1:18:42] Intuition versus discipline
[1:24:08] Post-credit scene
[1:27:47] Thank you to Alchemist Accelerator for sponsoring!
[1:28:48] If you enjoyed this episode, it would mean a lot if you could share it with one friend who’d also get a kick out of this!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“If you have the deal flow and you have the energy and have the skills to construct your own portfolio, then funds-of-funds obviously are more complimentary than necessary.” – Jay Rongjie Wang

“The first layer is setting up your own strategy. The second layer is portfolio construction. How do you do your portfolio construction based on the strategy you set out to do? And then manager selection comes last. Within the portfolio construction target, how do you pick managers that fit that ‘mandate?’” – Jay Rongjie Wang

“The later the stage you go, […] capital becomes more anonymous, and […] the more you converge to public market returns.” – Jay Rongjie Wang

“I only put the regenerative part of a wealth pool into venture. […] That number – how much money you are putting into venture capital per year largely dictates which game you’re playing.” – Jay Rongjie Wang

“Your average median of a fund-of-funds is higher than a venture capital fund, and the variance, the standard deviation, is lower. So it is possible for a VC fund to have 40%, 50%, or higher IRR. It’s much, much less likely for a fund-of-funds to achieve that, but also the likelihood of losing money is much, much lower for a fund-of-funds.” – Jay Rongjie Wang

“The reason why we diversify is to improve return per unit of risk taken.” – Jay Rongjie Wang

“Bear in mind, every fund that you add to your portfolio, you’re reducing your upside as well. And that is something a lot of people don’t keep in mind.” – Jay Rongjie Wang

“Once you have a strategy, the hardest thing for me is to stick to that strategy because you just meet those amazing managers, amazing funds all the time.” – Jay Rongjie Wang

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.

Posted on

2024 Year in Review

2024

Undeniably, one of the most insightful books I read this year has been Setting the Table by Danny Meyer. Someone I’ve been a long time fan of. If you’re no stranger to this humble blog, you’ll notice his cameos throughout previous pieces I’ve written. I am also remarkably late to the game. The book came out in 2008. And to this day, is as timeless as it was over a decade and a half back. Thank you, Rishi and Arpan for gifting me a copy.

That book has led to blogposts like this and this. To finally cold email him (yay, he replied! Danny, if you’re reading this, thank you for making my day, hell, and a good portion of my year!). New ways on how I support GPs. More intentional ways to hire. Inspired me to take on two more writing projects and a new podcast series in 2025 (don’t worry, Superclusters isn’t going anywhere, but expanding). And I’m sure it’s only the tip of the iceberg.

And as one last fanboy moment for Danny, there’s a line he has on page 220. A line the late and great Stanley Marcus of Neiman Marcus fame once told him. “The road to success is paved with mistakes well handled.” A line I haven’t stopped thinking about since I read it.

There’s a saying in the entrepreneurial world that it takes between 10 and 15 miracles for a startup to succeed. Each miracle is a trial by fire. A right of passage. A test of character. I’ve always believed that the job of an investor is not to be helpful all the time, or share celebrations on social media, or facilitate just connections. Despite having done many of the above myself, those are all, in my mind, table stakes. Rather, the job of an investor is to be there for at least one of those critical points of failure and to be extremely valuable. To help an entrepreneur handle their mistake well, to borrow Stanley Marcus’ line.

In another episode earlier this year, Jaclyn Freeman Hester shared one of the best soundbites ever said on Superclusters.

“If I hire someone, I don’t really want to hire right out of school. I want to hire someone with a little bit of professional experience. And I want someone who’s been yelled at.”

While it makes for a great clickbait title, the lesson extends further. One only gets yelled at by making a mistake. One learns not by making mistakes, but the public embarrassment of that mistake. If someone learn of the negative aftermath of a mistake, one won’t get the feedback mechanism necessary to grow from that experience. To analogize it to elementary math, if my afterschool teacher didn’t slap me with a ruler every time I got 9+8 wrong, it would have taken me a lot longer to learn that lesson. If no one catches you accidentally making an inconsistent calculation on the balance sheet, you may never learn from that mistake.

All that to say, someone who’s been yelled at made the mistake, received the feedback mechanism to improve, and learned to handle it better next time.

So, in my long preamble, and not to bury the lead, 2025 will be the year of big mistakes. Maybe. Hopefully, well handled. 2024 was the year of laying the groundwork. A lot of which were made explicit via this blog. I’m not saying I haven’t made any mistakes. Yes, I’ve left the toilet seat up. I should have asked for more concrete examples during certain podcast interviews. Almost forgot to file my annual tax extension. Forgot to mention a sponsor at an event (luckily my co-host had my back). Made the rookie intern mistake at work. Twice. Different things, but nevertheless twice. But those mistakes will be small compared to the ones I’ll make next year.

Nevertheless, here are the hallmarks of 2024!

2024’s Most Popular

  1. Timeless Content for the Weary Investor — Our society spends quite a bit of time focusing on results, outputs, and success. All of which are lagging indicators of the blood, sweat and tears people put in. So instead, earlier this year, I thought it’d be interesting to compile a list of content that some of the most successful investors (LPs and VCs alike) consume. What goes in their information diet? What are the inputs? Some results may surprise!
  2. The Science of Selling – Early DPI Benchmarks — With the economy outside of AI hitting a standstill and hitting record low numbers in terms of liquidity, I’ve found a constant stream of new readers via this blogpost. Many of which I imagine to be fiduciaries and capital allocators. I do hope that one day there is more content on selling and exiting positions in a liquidity-constrained environment though. Although, I may just put out a blogpost on secondaries in the new year, inspired by a number of conversations I’ve had this year already.
  3. How to Break into VC in 2024 — It may be obvious by now that there’s no one set path to get into venture. I’ve worked with colleagues who ranged in majors from history to food science to economics to computer engineering. Additionally, those who have been a founder, a banker, a consultant, a product manager, an artist, an athlete, an actress, a public relations specialist, and the list goes on. But if you were looking for the closest thing to a silver bullet, maybe this essay would be a great place to start.
  4. Five Tactical Lessons After Hosting 100+ Fireside Chats — Surprisingly, this has stayed as a perennial blogpost. I realize even now looking back, how much I’ve learned since, but nevertheless a good starting point for those who want to interview others.
  5. The Non-Obvious Emerging LP Playbook — The first blogpost I wrote on the topic of being an LP. Still my longest one to date. Since then, I’ve learned an LP comes by many a name. Capital allocator. Asset owner. And more specifically, the difference between multi-family offices and single family offices. Family businesses. Access versus asset class LPs. And more.
  6. Non-obvious Hiring Questions I’ve Fallen in Love with — I’ve been lucky enough to spend quite a bit of time around talent magnets this year. And in the surplus of applications, they’re forced to quickly differentiate signal from noise. And these are some of the questions I’ve heard them use. And well, have also used myself when hiring these past two years.

All-Time Most Popular

This list hasn’t changed much this year. One can say I have yet to outdo myself. Which may be true. I admittedly, also haven’t shared these blogposts much on Twitter. In fact, over 70% of this year’s posts never touched LinkedIn or Twitter. When in the past, I invested a bit more time in expanding to new audiences. For any essay that did go a little viral this year, it was because of you, my readers. So thank you!

  1. The Science of Selling – Early DPI Benchmarks
  2. The Non-Obvious Emerging LP Playbook
  3. 10 Letters of Thanks to 10 People who Changed my Life
  4. 99 Pieces of Unsolicited, (Possibly) Ungooglable Startup Advice
  5. Five Tactical Lessons After Hosting 100+ Fireside Chats

2024’s Most Memorable

This year was the year of LP content. Also, the year where I stopped using as many headers in my blogposts. Interestingly enough. It wasn’t any conscious decision, but at some point I just slowed my pace down. Excluding this blogpost and a few others. I wonder if I’ll use less next year.

So, to share them chronologically, here are some of my personal favorites:

  1. The Proliferation of LP Podcasts — I wrote this back in March at the beginning of Season 2 of Superclusters, and I still stand by this today. At the beginning of every content adoption curve, the question is: WHERE can I find this content? But as the content becomes fully adopted, in this case around being a capital allocator, the question will become: WHO do I want to / choose to listen to?
  2. From Demo Day to First Meeting: My Demo Day Checklist — There are times we have to make fast decisions when faced with a volume of options. Going to Demo Days and choosing who to follow up with is just one of such cases. I’m happy this year I’ve codified that practice when going to VC accelerator Demo Days. And I imagine it’s only a matter of time, before we’re faced with the volume of YC Demo Days, but for funds.
  3. The Power Law of Questions — As I’ve grown as an LP, I find myself being a lot more intentional with questions I ask fund managers. This blogpost serves as a record of questions I found myself asking quite often this year.
  4. Emerging Manager Products versus Features — In the startup world, the concept of products and features have become quite prevalent. One is a standalone business. The other is more of a subclause than a clause, incapable of being a product offering in of and itself. As I spend time thinking about an asset class, where the simplest, and likely, most facetious way of describing it, is we sell money, this blogpost serves as “value-adds” that deserve their own fund versus ones that should be built within a larger shop.
  5. Shoe Shopping — One of my posts where the title almost has nothing to do with the blogpost itself. But an observation of what differentiates VC funds beyond what they pitch the public.
  6. ! > ? > , > . — Another one of those blogposts where it’s hard to guess what it’s about from the title itself. Likely my worst essay title to date. Or best? A product of my gripe that most people don’t know how to ask for feedback. And good news! Some readers of this blog have reached out since asking for more directed feedback.
  7. Three E’s of Fund Discipline — A lot of GPs focus on entry discipline. A lot of LPs in 2024 focus on exit discipline. Both are equally as important, but both often forget about the third kind of fund discipline. Executional discipline. I give examples of each in this essay, which hopefully can help as a reminder for what is needed out of a great fund manager. A separate job description from just being a good investor. In fact, you can be the latter without ever needing to raise or manage your own fund, and still make the Midas List.
  8. Anecdotal Telltale Signs of Exceptionalism — One of the blogposts I imagine will continuously be updated. As even in 2025, I’m making edits to this one. This, at the end of the day, may just sit as an easter egg hidden in the deep corners of this blog. But for me, it will be a public log of things I’ve noticed, things I like, and things that I’ve seen work well for really exceptional people I get to meet and be friends with.

With that, 2024 comes to a close. See you all in the new year!

Photo by Eyestetix Studio on Unsplash

If you want to check out the past few years, you’ll find them encased in amber here:

4/12/2025 Edit: Added in Anecdotal Telltale Signs of Exceptionalism as one of 2024’s most memorable blogposts. One of the few blogposts that is likely to be dynamic, as opposed to static.

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.

Posted on

The 4 P’s to Evaluate GPs | Charlotte Zhang | Superclusters | S4E6

charlotte zhang

“Executional excellence can get you to being great at something – let’s call that top quartile – but it really is passion that distinguishes the best from great – top decile.” – Charlotte Zhang

As the director of investments, Charlotte Zhang oversees the selection of external investment managers at Inatai Foundation, conducts portfolio research, and helps to institutionalize processes, tools, and resources. Experienced in impact investing, she previously served as a senior associate at ICONIQ Capital and, before that, Medley Partners. Investing on behalf of foundations affiliated with family offices, her investments supported a variety of nonprofit work, from early childhood education to autism research. Charlotte was a founding partner of Seed Consulting Group, a California-based nonprofit that provides pro bono strategy consulting to environmental and public health organizations, and currently serves on the Women’s Association of Venture and Equity’s west coast steering committee and as a Project Pinklight panelist for Private Equity Women Investor Network. She is also on the advisory boards of MoDa Partners, a family office whose mission is to advance the economic and educational equity of women and girls, and 8090 Partners, a multifamily office consisting of families and entrepreneurs across diverse industries that is currently deploying an impact investment fund.

Charlotte earned a BS with honors in business administration from the University of California, Berkley. 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/

And huge thanks to this episode’s sponsor, Alchemist Accelerator: https://alchemistaccelerator.com/superclusters

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[02:56] Charlotte’s humble beginnings
[07:02] Lessons as a pianist
[10:23] Lessons from swimming that piano didn’t teach
[14:52] How Charlotte became an LP
[17:44] Where are emerging managers looking for deal flow these days?
[21:23] Reasons as to why Inatai may pass on a fund
[24:35] The 4 P’s to Evaluate GPs
[29:26] How small is too small of a track record?
[34:42] How do you build a multi-billion dollar portfolio from scratch
[39:43] The minimum viable back office for an LP
[42:03] Underrated Bay Area restaurants
[47:01] Thank you to Alchemist Accelerator for sponsoring!
[48:02] If you learned something from this episode, it would mean a lot if you could share it with ONE friend!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Executional excellence can get you to being great at something – let’s call that top quartile – but it really is passion that distinguishes the best from great – top decile.” – Charlotte Zhang

“If you have enough capital chasing after an opportunity, alpha is just going to be degraded.” – Charlotte Zhang

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.

Posted on

The Holiday Special | Nakul Mandan and Ben Choi | Superclusters | S4PSE1

ben choi, nakul mandan

“VC is more about the ground game than the air game.” – Nakul Mandan

“Entrepreneurs think it’s going to be like the Michael Keaton version, and the good ones, they actually have to work through the Christopher Nolan version of Batman.” – Ben Choi

Nakul Mandan is the founder of Audacious Ventures. Audacious is a seed stage venture firm managing ~$250M. Audacious’ foundational belief is that ultimately startup success comes down to two key ingredients: Large markets and A+ teams. Accordingly, the Audacious team focuses on two jobs: 1/ Invest in force of nature founders; 2/ Help them recruit an A+ team. Then they get out of the way. Prior to founding Audacious, Nakul was a GP at Lightspeed.

Some of the companies Nakul has backed over the last decade include: Gainsight, People.ai, WorkOS, Multiverse, Marketo, 6Sense, BuildingConnected, Vartana, Tezi and Maxima, amongst others.

You can find Nakul on his socials here:
X / Twitter: https://x.com/nakul
LinkedIn: https://www.linkedin.com/in/nakulmandan/
Personal Website: https://www.nakulmandan.com/

Ben Choi manages over $3B investments with many of the world’s premier venture capital firms as well as directly in early stage startups. He brings to Next Legacy a distinguished track record spanning over two decades founding and investing in early-stage technology businesses. Ben’s love for technology products formed the basis for his successful venture track record, including early stage investments in Marketo (acquired for $4.75B) and CourseHero (last valued at $3.6B). He previously ran product for Adobe’s Creative Cloud offerings and founded CoffeeTable, where he raised venture capital financing, built a team, and ultimately sold the company.

Ben is an engaged member of the Society of Kauffman Fellows and has been named to the Board of Directors for the San Francisco Chinese Culture Center and Children’s Health Council. Ben studied Computer Science at Harvard University before Mark Zuckerberg made it cool and received his MBA from Columbia Business School. Born in Peoria, raised in San Francisco, and educated in Cambridge, Ben now lives in Palo Alto with his wife, Lydia, and three very active sons.

You can find Ben on his socials here:
X / Twitter: https://x.com/benjichoi
LinkedIn: https://www.linkedin.com/in/bchoi/

And huge thanks to this episode’s sponsor, Alchemist Accelerator: https://alchemistaccelerator.com/superclusters

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[04:14] Why is Nakul fascinated by Batman?
[06:41] Does entrepreneurial motivation often come from inspiration or frustration?
[10:33] Nakul’s childhood and early upbringing
[14:37] How Nakul grew from introvert to extrovert
[16:19] Did Ben see the ambition in Nakul from the day they first met?
[18:19] How did Ben’s parents’ work in Chinatown influence Ben as a teenager?
[22:47] How did Ben and Nakul meet?
[28:50] Would Nakul have raised in 2020 if he knew how hard it would be?
[33:49] Why did Next Legacy not invest in Fund I, but in Fund II?
[37:49] How did Nakul react to the pass on Fund I?
[39:56] The kinds of people at Next Legacy’s dinners
[43:49] Why Audacious kept a low profile in 2021
[49:01] Why Audacious deployed Fund I over 4 years, instead of 3
[51:46] Balancing the paradox of one of Audacious’ cultural values
[55:14] The difference between pitching individuals and institutions
[1:00:42] What is it like to be married to an interior designer?
[1:02:40] Nakul’s favorite coffee shop, bar, and restaurant
[1:05:56] What makes a sock special to Ben?
[1:07:17] Why does Ben still like venture?
[1:08:10] Why does Nakul still like venture?
[1:11:36] Thank you to Alchemist Accelerator for sponsoring!
[1:12:37] If you enjoyed this holiday episode, and want more like this, do let me know!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“The risk is slow failure. And actually that’s the worst kind of failure even for entrepreneurs that we back. They’re all talented people. Some ideas work; some don’t. It’s when they end up spending seven, eight years and then it doesn’t work. Then it takes out seven, eight years of their life.” – Nakul Mandan

“Entrepreneurs think it’s going to be like the Michael Keaton version, and the good ones, they actually have to work through the Christopher Nolan version of Batman.” – Ben Choi

“If you don’t wear ambition on your sleeve, how do people know you’re ambitious?” – Nakul Mandan

“VC is more about the ground game than the air game.” – Nakul Mandan

“Always remember there’s a human on the other side of every conversation.” – Nakul Mandan

“The thing about working with self-motivated people and driven people, on their worst day, they are pushing themselves very hard and your job is to reduce the stress in that conversation.” – Nakul Mandan

“If you have an understated personality, wear something really bright.” – Ben Choi

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.

Posted on

The Year 1-3 AGM “Playbook”

conference, agm, summit, annual general meeting

A good friend, who’s hosting an annual general meeting (AGM) for his LPs in his first year of the fund, pinged me the other day asking if he should include the IRR metrics in his presentation day of. For context, it was negative because well, that’s how the math works. It’s almost always negative for any venture fund you invest in, in years 1-3. As you’re investing more money, the portfolio has yet to get marked up and raise a new round. So alas, negative rate of return.

Given that he had a lot of first-time LPs in his fund, he wasn’t sure if they would understand the context of the IRR metric if he just put it on a slide. So he was biased with not including it. To which I responded with… of course you should. For the bread and butter of being a fiduciary of capital, you should always bias towards transparency and honesty. But you should educate them every year in your first three years of the fund on what each number means and what is industry standard. Moreover, the biggest thing you’ll be measured against in the first three years of any fund is the discipline you exhibit. Did you do what you said you were going to do?

Then it brought on a larger question. What should GPs include in their AGMs in the first three years?

So I thought I’d write a blogpost about it.

This won’t be a two-hour documentary, nor a 300-page novel. But rather, just the governing principles of how I think about running annual summits for your LPs. So, as a general compass for the rest of this post:

  1. The basics to share
  2. Content at large and what to expect for the duration of the programming
  3. Gifts

The basics

First things first, the basics. What are the metrics to share?

  1. MOIC and/or TVPI
    • I prefer both gross and net, but most really just share net
  2. IRR
  3. # of investments (total)
  4. Capital called
  5. Capital deployed
  6. # of investments per pillar/vertical in your thesis (if relevant)
  7. # of investments broken down by stage (if relevant)
  8. Average check size
  9. Average entry ownership
  10. Average entry valuation
  11. Notable wins / progress in portfolio companies, and why it matters
  12. Asks for LPs
  13. Where is the market today?
  14. Where is it going? Notable trends

The first 10 are required as a fiduciary of capital. The last 4 means you’re playing professor for a bit. LPs invest in you for your opinion, for your perspective. Also it’s important to note, if more than 20% of your LPs are first-time LPs, you may want to lean more on being a professor of sorts to set expectations. And how to interpret your data. And yes, it’s worth being honest here. In good and bad times.

Do note that in the first 2-3 years, your IRRs will suck. TVPI will be roughly 1X. DPI is either negligible or non-existent. These are all things that are worth highlighting to first-time LPs in the venture space. Focus on why discipline matters more than performance in the first 3-4 years. Did you do what you said you would do?

Also, it is quite normal to invite both your current fund LPs, as well as the LPs you would like to have one to two funds from now. Although if you’re inviting the latter, do be cognizant on sharing sensitive data about your portfolio. Regardless, the AGM is an opportunity to deepen any relationships — current and future.

And, just like a Dreamforce or TwitchCon or WWDC, it’s a chance to reinvigorate your audience about why they should care about you.

Content at large

I’m not the first to say it, nor is it the first time I’m writing about it. For instance, here and here. But GPs are evaluated on primarily three things: sourcing, picking, winning. There are more yes. GP-thesis fit. Differentiation. Portfolio construction. Ability to build an enduring firm. Selling and exiting positions. And so on. But if VCs can boil everything down to team, market, and product, this is the LP equivalent.

And well, the truth is you’re always being evaluated. Even after the fundraising sprint. As in another 2-3 years, you’re going to ask the same LPs to re-up their capital, just like a founder to a multi-stage VC would.

All that to say, in the AGM, you should find ways to highlight each through the content you present. To share some examples:

  • How you source
    • Have your companies share how you first met. The crazier the story, the better.
    • If you have a community/newsletter/podcast, bring in a really high quality advisor or speaker from there.
    • If you champion yourself on outbound sourcing, find an impressive speaker that you cold emailed.
  • How you pick
    • Showcase 1-2 companies with strong growth
    • If you had a track record prior to the firm with an obvious win (i.e. you were a seed investor in Airbnb), bring the founder in to speak.
    • Share market insight that no one else knows. What is your prepared mind?
    • Request for startups.
  • How you win
    • Showcase a skillset that you have through someone else. That someone else can be a former colleague, a name-brand co-investor, or founder. Have them talk about you and that skillset. Stories are always better than facts.
    • Showcase 1 hot company in your portfolio that everyone wanted to get access to but only very few got in. Have that founder share why they picked you.

Of course, you don’t have to be explicit with the above, but nevertheless, a useful framework for planning content.

Also please don’t have your entire portfolio present. Nor any more than 4-5 companies. Two is ideal. Ideally, you want a diverse cast of speakers. And I mean, diverse by job title.

Gifts

I’m always biased towards gifts. It is one of my primary love languages, but also in any event I host or help host, I think a lot about surprise and suspense.

Surprise is relaying information to someone where they do not expect it. Suspense is relaying information where they expect it, but don’t know how or when it’ll drop. Surprise is what gets people talking about your event after. Suspense is what brings people to the event.

The earlier section on content is suspense. Gifts are usually surprises at AGMs.

In terms of what kinds of gifts to give, the most important guiding principle here is to be thoughtful. As Zig Ziglar / Mark Suster once said, ” People don’t care how much you know until they know how much you care.”

It’s less about the gift you give; it’s more important about how you deliver it.

Some examples of thoughtful ones I’ve seen at AGMs in the past:

  1. A GP’s favorite book they read that year
  2. A signed copy by the author of a deeply meaningful book that shaped the way the GP thinks today
  3. A letter at each LP’s seat of the first interaction between the GP and each of the LPs.

In closing

AGMs are the one of the few times in a year, hell, in fund cycle, to remind LPs of why they love you. Are they thinking about you when they put together the following year’s budget and allocation schedule?

And yes, you do need to remind LPs on why they love you. Just like, even if you’re in a happy marriage, every so often, you need a date night. Keep the kids at home. Get a babysitter. And do something wild with your spouse.

Pat Grady has this great line. “If your value prop is unique, you should be a price setter not a price taker, meaning your gross margins should be really good.” In a similar way, you want to be a schedule maker, not a schedule taker. And to do so, you need to get people excited. And well, you need to be unique. You need people to look forward to your AGM, and not see it as a chore. Since, let’s be honest; if I’ve been to two dozen or so AGMs, not as an LP in most of them, then a seasoned LP is definitely invited to many more.

Earlier this year, I flew over to San Diego for an AGM. I found out two other friends were also flying in to SD for an AGM that same Thursday. The three of us agreed to catch up during the happy hour, assuming all of us were going to the same one. Turns out, we each went to a different AGM. Same day, same time. All within a 10-minute Uber ride from each other. Spoiler, we later escaped our respective events during the happy hours to catch up elsewhere.

Along the same wavelength, in October this year, I was moderating a talk in a building, where there were two other AGMs happening in the same building at the same time. And three others within a five-block radius in SF… at the same time. Those were only the ones I knew of. That said, it was SF Tech Week.

Simply, you’re fighting for attention. And everything above is just table stakes. It’s the bare minimum. But what sets the great ones apart from the forgettable ones is a reminder of what makes that GP or set of GPs special. Their own flavor. Their own touch. And it’s a combination of thoughtfulness and personality. And if you have those, the small bumps in the road don’t matter.

Hope the above helps.

P.S. Why am I sharing this?

  1. I don’t think knowledge is ever perennially proprietary. Today it may be, tomorrow it will not.
  2. If you’re a GP reading this, this is pretty much exactly what I share with all the funds I’ve worked with to help plan their annual summits for LPs. So, you won’t have to hire me anymore to help you with your annual summits. I don’t care about making a living helping other people plan and organize AGMs. But I would like to go to higher quality events in general. 🙂
  3. A rising tide raises all ships.

Photo by Jakob Dalbjörn 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.

Proudly powered by WordPress