How Trees Fall

lumberjack, felling a tree, axe, emerging lp

I caught up with a single family office over the holidays. Let’s call him Mark. Mark told me that he had caught up with a Fund I GP that I had passed on. Let’s call her Susan. In that conversation with that GP, he told Susan that I introed him to another GP “Charlie” whom she knew and whom I invested in, which he eventually passed on. And Susan asked Mark why I invested. That it made no sense. That Susan herself would have never invested in Charlie. As such, she didn’t know why I would invest in Charlie and not her. After sharing that last line, with no explicit question that plead for an answer, Mark looked at me, waiting to see how I’d respond.

I stared back at him. And he to I. And I to him.

As he felt seemingly unsatisfied with my reaction, I asked him, “If I put both of these GPs on a report card, how would you score each?”

He followed up, “Susan is more experienced. She’s done X and Y. And she came from Z.”

“You’re right. Susan is all of that. In fact, on a report card, it’s fair to say that her GPA is a solid B+, maybe an A-.”

He concurred.

I went on. “And Charlie would probably score a B, maybe B-, if we were really critical. But to you, did anything about Susan jump out at you?”

“Not exactly.”

“What about Charlie?”

“Well, there’s that…”

“I agree. For me, and you don’t have to agree with my assessment, Charlie is on paper a lower GPA than Susan, but Charlie spikes in very particular areas. Areas I personally believe puts him in a position to do really well. That he will have a good chance to outperform. Susan is factually better in almost every area than Charlie is, but she doesn’t spike in any area. At least it’s not obvious to me. I like her thesis. I think she has a great GP-thesis fit. And I do believe that her thesis has a really good chance of being right, but I’m not sure she’s the only person in the world who can do that, much less the best person in the world to do it. In fact, I can think of two other GPs who spike in that thesis area where she doesn’t.”

It’s harsh criticism. And it’s not my place to give non-constructive criticism. So what I said when I passed was that we had other deals in the pipeline that were a lot more interesting to us. Which is true. But it’s not my place to say “I don’t think you’re good enough.” And she probably felt my pass was unsatisfying. Because in her shoes, I’d probably feel the same.

I don’t invest in all-rounders. There’s a time and place and industry for those. But I don’t believe it’s venture. Even less early stage emerging managers. There’s a line I’ve long liked in the F1 world. “In Formula 1 itโ€™s nearly impossible to go from 13th to 1st on a sunny day, but itโ€™s possible on a rainy day.” In the uncharted territory of true early, early stage investing, it’s always a rainy day. And to go from 13th to 1st, you need to make bold decisions. Measured, well-timed, but risky decisions. You need to make certain sacrifices to do so.

To me, that meant comparatively lower grade-point averages, but much, much higher select individual subject grades. In fact, only an A++ would suffice. A spike must be at least three standard deviations from the mean. As an emerging manager LP, who plans to be an active participant in the journey, naturally with the GP’s permission, it falls on me and my peers to help our GPs raise their overall GPAs, but we can’t help them spike. But in that, we must know and recognize their flaws.

One of the most interesting spectacles I’ve always marveled at is how lumberjacks fell trees. The first cut is the notch cut that indicates the direction the tree will fall. The second is the felling cut that catalyzes the tree to fall, acting as the hinge.

In many ways, the GP spikes (and flaws) makes the first cut. Whether you count it as nature or nurture. The GP’s job is to figure out which direction they’d like to fall. Or to borrow a line from Mark Manson’s most important question of your life: “What pain do you want in your life? What are you willing to struggle for? How do you choose to suffer?” To further borrow, “What determines your success isnโ€™t ‘What do you want to enjoy?’ The question is, ‘What pain do you want to sustain?’ The quality of your life is not determined by the quality of your positive experiences, but the quality of your negative experiences. And to get good at dealing with negative experiences is to get good at dealing with life.” All in all, it’s a GP’s job to make that choice. An LP cannot make that choice for the GP. And it is a function of the flaws they’re willing to overcome, and how they want to double down on their spikes.

The second cut is for investors, board and advisory members to nudge our investees towards the direction they so chose. As the great Tom Landry once said, “A coach is someone who tells you what you don’t want to hear, who has you see what you don’t want to see, so you can be who you have always known you could be.” But the prerequisite for the second cut is the first. The first requires intentional and special people.

Along a similar vein, my buddy Henry wrote a post recently I really liked.

“Is this founder special?” That’s probably the only question that has to be asked in every non-obvious investment decision. Maybe every investment decision. But especially true under imperfect information conditions. And special isn’t just about getting a high GPA.

Photo by Radek Skrzypczak 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.

On Investing in Generalist GPs

pull up bar, high bar

A quick thought on investing in generalist funds, inspired by a GP following up with me after I told him I prefer investing in “specialist” funds. Which he followed up with “I am a stage specialist.” Technically, he’s not wrong. But under that definition, almost all emerging managers are stage specialists. Their specialization just depends on which stage we’re talking about. But when most, including myself, use the word specialists, we really mean sector specialists.

A couple things to caveat before I go further:

  • I’m an emerging LP. I don’t have that many years or funds I’ve invested in at this point, so I need to spread my coverage wider than after I figure things out. But not too wide that I trend towards the median, also known as “indexing venture.” Median, even top quartile in today’s venture, is uninspiring. And there are far better liquid options that can deliver the same return profile as top quartile in venture.
  • I have a stage preference because I think it’s where you can build meaningful relationships while still figuring things out alongside the founder. As they say, a friend in need is a friend indeed.
  • I have a geographical preference because of my existing network, which makes certain opportunities easier to diligence.
  • I prefer sector specialists because I’m designing a portfolio where I can hopefully predict where 50% of my underlying portfolio will come from, and 50% where I can’t. Since most things in venture are opportunistic, and I give each of my managers that longer leash to make bets to be opportunistic (20%-ish; not a hard number, but can’t be 70%). Specialists are easier to underwrite how valuable they can be to a portfolio. Generalists, it’s harder to, unless I’m somehow convinced that a GP has a unique skillset I’ve never seen before in my career so far, which the bar just gets higher the longer I’m in business, AND that skillset is uniquely valuable to a founder across sectors.

I want to have exposure to 50-60 new companies/opportunities per year, with very little overlap. Stats suggest 30 of a sample size becomes statistically significant so anything less than that, I’m not giving my null hypothesis an honest chance. If I believe that 20 companies per year matter (not sure of the exact number, but this number feels directionally accurate), I want to know my managers collectively together has at least a 1 in 3 chance of hitting at least one. That means being in the right networks. Proportionally, some should spend their time hunting (i.e. actively spend time in interesting ways to find and chase after the best opportunities). Some should spend time fishing (i.e. building a brand so fish swim to or at least through their fishing hole). Some should spend time farming (i.e. cultivating relationships).

That said, my portfolio has yet to deploy into 50 new opportunities per year, so I am actively adding to it, in specific areas. Areas I don’t have good coverage over for now. So to invest in a new sector generalist manager, I likely need to “fire” one or more managers from my existing portfolio, which means I won’t re-up in them. And there are only a small handful o reasons I’ll won’t re-up into an existing manager.

  • Their investments have really deviated off of the thesis I underwrote them to have.
  • There’s a major team change that puts into question their ability to outperform.
  • Their fund size has drastically increased to a point I question the return profile that would get me excited.
  • They’ve made a series of bad bets where I question their ability to make decisions (i.e. I meet with their founders and they just don’t feel like high performers.).
  • They lose motivation to be a VC and hang up the cleats. In this case, I won’t have to say the “no.” They will for me. But on occasion, they’ll try to raise another firm, or hear whispers on how tough the market is, and they’ll choose not to raise another vintage.
  • I meet with a new GP covering an area an existing manager covers but materially better on almost all fronts. 10-20% better, even 50% better, is negligible, and also really hard to measure in foresight. And assuming the manager I’ve invested in learns quickly, that 50% gap will be closed shortly.

Luckily none of the above has happened yet. But I imagine, because I’m not perfect, at some point, one or some of the above will.

So if you’re a generalist covering 2-4 areas that my existing portfolio is covering AND has reasonable access to, in order to invest in you, I must believe that you’d be better than the firms I’ve already invested in, then subsequently fire them from my portfolio the next vintage.

That is a high bar. And only gets higher the more my portfolio grows.

Photo by Vitaly Gariev 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 Most Disappointing Podcast You’ll Ever Listen To (ft. Allie Garfinkle) | Superclusters | S6PSE2

allie garfinkle, david zhou, superclusters

Warning: This is a brief-ish, but hopefully entertaining intermission from the usual Superclusters programming. When we passed the 50th episode mark more than a few episodes ago, Tyler (my editor) and I thought it’d be interesting to record an episode where I change seats. Instead of me asking the questions, someone else would ask me questions. And I couldn’t imagine any better person to do so than my good friend, Allie, who in my humble opinion, is one of the best interviewers alive today.

Allie Garfinkle is a senior finance reporter for Fortune, covering venture capital and startups. She authors Fortuneโ€™s weekday dealmaking newsletter Term Sheet, hosts the Term Sheet Podcast, and co-chairs Fortune Brainstorm, a community and event series featuring an annual retreat in Deer Valley, Utah. A regular contributor to BBCโ€™s Business Matters podcast, Allie is also a frequent moderator at major conferences such as SXSW. Before joining Fortune, she covered Amazon and Meta at Yahoo Finance and helped produce Emmy-nominated PBS Frontline business documentaries, including Elon Muskโ€™s Twitter Takeover and The Power of the Fed. A graduate of The University of Chicago and New York University, Allie currently resides in Los Angeles.

You can find Allie on her socials here:
LinkedIn: https://www.linkedin.com/in/alexandra-garfinkle1/
X / Twitter: https://x.com/agarfinks

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

OUTLINE:

[00:00] Intro
[02:01] Art
[09:39] Competition
[17:49] Paleontology
[18:14] Allie’s Tiki mugs
[22:49] How has VC evolved?
[29:41] Evaluating risk
[43:04] Why is it important for VCs to stay in touch?
[47:10] Are there reliably good investors?
[53:09] Young GPs in market
[54:58] How useful is education that come via public talks?
[57:50] Does your niche fund size make sense for the market?
[1:01:16] Is there too much venture capital?
[01:05:24] How much of VC is art vs science?
[1:07:18] What’s going on in Allie’s world?
[1:09:45] Post-credit scene: Receipts

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

Iโ€™m intentionally keeping this section void of the things that I said since I hate the idea of quoting myself.

โ€œPart of the point of this [investing job] is that you want to be anonymously, asymmetrically correct. And you canโ€™t necessarily be that by saying or doing the same thing as everyone else. That being said, the worst nightmare for a VC is that no one wants to back a company theyโ€™ve backed.โ€ โ€” Allie Garfinkle

โ€œIf it eventually doesnโ€™t become consensus, you were wrong.โ€ โ€” Allie Garfinkle


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.

Timeless VS Just-In-Time Lessons | Earnest Sweat & Alexa Binns | Superclusters | S6PSE1

earnest sweat, alexa binns

The holiday season has always been a great time to celebrate the movers and shakers in our world. This season we’re celebrating my personal favorites in the LP world. To start this mini-holiday series off, Earnest Sweat and Alexa Binns runs one of the most popular podcasts on venture capital limited partners, Swimming with Allocators. I was also fortunate enough to be on their podcast as well as a bonus crossover episode.

You can find Earnest on his socials here:
LinkedIn: https://www.linkedin.com/in/earnestsweat/
X / Twitter: https://x.com/EarnestSweat

You can find Alexa on her socials here:
LinkedIn: https://www.linkedin.com/in/alexabinns/
X / Twitter: https://x.com/alexabinns

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

OUTLINE:

[00:00] Intro
[02:09] Alexa’s earliest relationship with money
[03:28] Earnest’s earliest relationship with money
[04:45] Earnest’s first major purchase
[06:41] Alexa’s first major purchase
[08:25] The difference between public speaking and interviewing
[12:19] Memorable guests on the SwA podcast
[14:46] To do or not to do in-person interviews
[18:05] Evolution of YouTube titles
[20:04] Why err towards evergreen content?
[22:30] Was SwA designed for LPs or GPs?
[24:12] How did Earnest and Alexa meet?
[24:56] How did Swimming with Allocators start?
[27:21] The Pandora’s Box of intros
[28:02] Alexa’s 3 buckets for LP investing
[30:12] What is ‘coming soon’ for Earnest and Alexa?
[36:58] Post-credit scene: Spider-Man & Investors as Avengers

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œHaving done my investment philosophy, Iโ€™ve got three buckets. There is the โ€˜Let it ride, you canโ€™t beat the marketโ€™ bucket. Thatโ€™s the majority of what Iโ€™m working with. Thatโ€™s 90[%] plus. There is a bucket where Iโ€™ve worked as a VC, Iโ€™ve managed a bunch of LP investments, I am better suited to vet deals than the average person. I believe in my ability to pick winners in this very thin layer of finance. Just in angel investing and GP selection where Iโ€™ve got lived experience and then my network. And then thereโ€™s a bucket for other ways capital can make your life richer.โ€ โ€” Alexa Binns


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.

When Do You Know If You’ve Grown Up as a VC? | El Pack w/ Ben Choi | Superclusters

ben choi

Ben Choi from Next Legacy joins David 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.

Gilgamesh Ventures’ Miguel Armaza, also host of the incredible Fintech Leaders podcast, asks Ben what is the timing of when a GP should consider raising a Fund III.

Similarly, but not the same, Strange Ventures’ Tara Tan asks when an LP backs a Fund I, how do they know that this Fund I GP will last till Fund III.

Arkane Capital’s Arkady Kulik asks how one should think about building an LP community, especially as he brings in new and different LP archetypes into Arkane’s ecosystem.

Ben manages over $3.5B investments with premier venture capital firms as well as directly in early stage startups. He brings to Next Legacy a distinguished track record spanning three decades in the technology ecosystem.

Benโ€™s love for technology products formed the basis for his successful venture track record, including pre-PMF investments in Marketo (acquired for $4.75B) and CourseHero (last valued at $3.6B). He previously ran product for Adobeโ€™s Creative Cloud offerings and founded CoffeeTable, where he raised venture capital financing, built a team, and ultimately sold the company.

Ben is an alum and Board Member of the Society of Kauffman Fellows (venture capital leadership) and has also served his community on the Board of Directors for the San Francisco Chinese Culture Center, Childrenโ€™s Health Council, Church of the Pioneers Foundation, and IVCF.

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 Los Altos with his wife, Lydia, three very active sons, and a ball python.

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

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

OUTLINE:

[00:00] Intro
[05:05] Ben’s 2025 Halloween costume
[06:44] Jensen Huang’s leather jackets
[07:24] Jensen Huang’s answer to Ben’s one question
[10:05] Enter Miguel, Gilgamesh Ventures, Fintech Leaders
[14:43] What are good signals an LP looks for before a GP raises a Fund III?
[22:35] Why does Ben say ‘established’ starts at Fund IV?
[25:08] Who’s the audience for Miguel’s podcast?
[27:52] In case you want more like this…
[28:32] Enter Tara and Strange Ventures
[32:46] How does Ben know a Fund I will become a Fund III?
[36:53] How does Ben know if a GP will want to build an enduring career?
[40:58] How does Tara share a future GP she’d like to work with to Ben?
[42:43] Marriage and divorce rates in America
[43:34] What should a Fund I do to institutionalize?
[46:28] Should you share LP updates to current or prospective LPs?
[48:57] Enter Arkady and Arkane Capital
[51:09] How does one think through LP-community fit?
[1:01:31] What’s Arkady’s favorite board game?
[1:03:08] Ben’s last piece of advice to GPs
[1:09:50] My favorite Ben moment on Superclusters

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œThe dance of fundraising is when you do have [your thesis], the LP has to figure out is this a rationalization of the past or is it actually what happened? Was this known at the time? Because if it was, we can have some confidence in the future going forward. But if it was just a rationalization of some randomness, then itโ€™s hard to know if Fund IV or V or VI will benefit from the same pattern.โ€ โ€” Ben Choi

On solo GPs bringing in future partners by Fund IIIโ€ฆ โ€œThe future unidentified partner is the largest risk that we have to decide to accept. So there actually isnโ€™t a moment where we decide this GP is going to be around for Fund III. Itโ€™s actually the dominating risk we look at and we get there, but itโ€™s a preponderance of other things that we need to build our conviction so high that weโ€™re willing to take that risk.โ€ โ€” Ben Choi

โ€œItโ€™s brutal. Itโ€™s a 30-year journey. For any GP who raises a single dollar from external LPs, itโ€™s a 30-year journey.โ€ โ€” Tara Tan

โ€œI donโ€™t think anyone goes into this business to raise capital, but your ability to raise capital is ultimately what allows you to be in this business.โ€ โ€” Ben Choi

On communityโ€ฆ โ€œYour core question is how much diversityโ€”in the technical term of diversityโ€”can you tolerate before you lose the sense of community.โ€ โ€” Ben Choi

โ€œMost letters from a parent contain a parent’s own lost dreams disguised as good advice.โ€ โ€” Kurt Vonnegut

โ€œFundraising is a journey of finding investors who want what you have to offer; itโ€™s not convincing somebody to do something.โ€ โ€” 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.

Insight Per Half Hour

lightbulb, dark, insight

This is a blogpost where I’ll risk sounding like an asshole. Probably am already one to some, although I try not to be.

My jobโ€”as well as all other investors, hiring managers, talent agents, sports scouts, just to name a fewโ€”is to make decisions relatively quickly when faced with the pure volume of inflows. Not necessarily investment decisions, but in a brief interaction, it’s my job to figure out if I want to continue spending time with someone. And if I do know, I need to set expectations clearly as soon as I can. Usually within the first interaction. Because of that, I find it useful to develop heuristics.

(max age at which the knowledge one has today would still be impressive) – (age today) = (# of F’s given)

Where… negative F’s is a lost cause. You’re too late to the game. Zero F’s means it’s to be expected. Expectation meets reality. And the larger the number of positive F’s given, the more impressive you are.

Let me contextualize this.

Today, I know that 7 x 8 = 56. Not impressive at all. I’m 29, at the time of writing this post. The max age knowing what 7 x 8 is, and still be impressive, is probably 5 years old.

The Pythagorean Theorem probably caps out on the “impressive scale” at 8 or 9-years old before it’s to be expected. Maybe 10. There are some pieces of knowledge that have an expiration date on impressiveness. If you know E=mc2 at 6-years old, you might be a genius. If you brag about it at 30-years old, people will wonder what you’ve done with your life. That’s not to discount the folks who spend their life on the actual intricacies of the equation. There is also an age where it starts being worrisome if you still don’t know how to do something. At 10, if you know how to file taxes, people will shower praises at you. At 40, if you don’t know how to file your taxes, people will scoff.

The interesting thing is it extends beyond simple math. In venture, there is a certain point in your career that you need to know what pre- and post-money SAFEs are. You need to know the responsibilities of a board member, if you want to be a lead investor. You need to know how to file your K-1’s. You need to know what qualifies for QSBS. If you’re three months into your job as a VC, I don’t expect you to know how to negotiate pro-rata rights when a downstream investor wants you to sell a piece of your equity so they can keep their ownership targets. If you’re a VC, and not a GP, I don’t expect you to know the difference between a 3(c)(1) and a 3(c)(7) entity and that if you have a 3(c)(1) structure, then any LP owning more than 10% will be subject to the look-through rule and every single underlying LP in theirs counts as a beneficial owner and counts towards your 100 investor cap.

There is also so much free content online at this point that the max age where someone will still be impressed by a certain skillset or knowledge will continue to decrease as media democratizes knowledge. Made even easier with AI. Although do take niche knowledge generated by AI with a grain of salt.

The second part, which is equally as important, is: How did you acquire that piece of knowledge? For instance, one of the common “Would you rather?” assessments when I first jumped into venture was: Would you rather invest in someone who graduated from MIT with a 4.0 GPA or someone who took every free computer science course online to learn to built a software product? The common consensus on our team was the latter. The latter shows drive and intrinsic motivation. Critical for someone who’s a founder. Aram Verdiyan and Pejman Nozad call it “distance travelled”, a terminology I’ve since borrowed.

As such, both the insight and the insight development matters. It’s what I look for when I have an intro conversation with a GP and/or founder. It’s what I seek when I go to an investor’s annual summit. So much so, that in my notes, I keep track of who has the highest “insight per half hour.” And I have an extreme bias towards those who have something insightful to share almost every time I have a conversation with them, as well as those who accumulate insights faster than others.

Of course, this isn’t the end all, be all heuristic, but I find it helpful as a rough rule of thumb when a GP claims to have insight in a given area.

Photo by Ethan Hoover 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.

“Venture Should Play More Like Moneyball” | Carson Monson | Superclusters | S6E9

carson monson

“The limiting downside is actually something a lot of emerging managers donโ€™t think about. If you can turn all of your portfolio companies that donโ€™t hit that exit velocity, if you can find a soft landing for those companies versus thatโ€™s a writeoff and theyโ€™re dead and done, thatโ€™s extra effort, but thatโ€™s an extra turn on your fundโ€™s performance.” โ€” Carson Monson

Carson Monson is a seasoned allocator with nearly a decade of experience backing emerging and spinout GPs across large institutions, government entities, and family offices. After stints at Greenspring, SITFO, and building a fund of funds strategy for a large European single family office, he now runs the fund of funds at CrossRange, which focuses on supporting top-tier emerging and spinout GPs.

Carson has backed everything from micro funds to high-profile managers spinning out of tier-one firms. He is deeply committed to being a thought partner and strategic resource to the GPs he supports, helping them navigate the complexities of fund building and long-term success in the VC industry.

You can find Carson on his socials here:
LinkedIn: https://www.linkedin.com/in/carson-k-monson/
X / Twitter: https://x.com/Monsson_

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

OUTLINE:

[00:00] Intro
[02:08] Wildlife and wholesome trouble
[06:03] The journey to being an LP
[10:54] How did Carson join Greenspring?
[13:55] Lessons across Greenspring
[15:46] How many deals did Greenspring do per year?
[18:46] An example of a qualitative metric worth measuring
[20:16] How many off-thesis bets is a VC allowed to make?
[21:25] When do GPs move from thematic bets to opportunistic bets?
[25:45] How much AUM should any one GP have?
[29:46] Why does Carson liked concentrated portfolios?
[30:32] The case for concentrated portfolios
[36:40] Relationships with GPs should stay at the LP partner level
[39:49] Fund strategy at Fund (n) vs Fund (n + 1)
[45:19] What the hell is ‘critical node theory?’
[49:54] Examples of great references
[52:58] The halo effect of mega funds
[58:48] How does Carson get to inbox zero
[1:02:09] Why is CrossRange different?
[1:08:17] The last time Carson had a pinch-me moment
[1:10:17] Carson’s ricotta gnocchi
[1:12:28] Post-credit scene: Ramen, gluten, Tokyo, and Tonkatsu Suzuki Pt 2

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On if 20% of the fund is focused on opportunistic betsโ€ฆ โ€œWealthy is a nice word. I would say [20% is] egregious. […] 10%, itโ€™s not like itโ€™s the right number, but itโ€™s the number most LPs wonโ€™t contest.โ€ โ€” Carson Monson

โ€œIn the past, there have been GPs who are truly excellent at one thing or a couple of things, whether thatโ€™s a thesis, strategy, or an approach. And that approach makes a ton of sense at the fund size that theyโ€™re operating at or maybe a little bit larger. In the 20-teens especially, people were able to raise more and more, and strategy drift became a huge issue. That is something managers have to face the music on now. Itโ€™s almost like the idea of being a professional baseball player and grinding and working your way up and becoming excellent and an all-star baseball player. Then being, โ€˜Well, the motion is similar in cricket, so Iโ€™ll just go play cricket now.โ€™ Ya some of the motions are similar, but itโ€™s a fundamentally different sport. Strategy drift, fund size drift; it can be a really easy trap to fall into. The motions are similar, but you lose that competitive edge when you start to play a different sport.โ€ โ€” Carson Monson

โ€œIf youโ€™re more concentrated, there is an ability to impact outcomes more meaningfully. I like GPs that play a critical role in the ecosystem in which they operate in. If you play a critical roleโ€”whether thatโ€™s in go-to-market motions, whether thatโ€™s in commercialization, whether thatโ€™s in branding and storytellingโ€”there are so many ways you can play that role. Those types of GPs tend to have an ability to move the needle for their founders moreโ€”both on the upside and limiting the downside.โ€ โ€” Carson Monson

โ€œThe limiting downside is actually something a lot of emerging managers donโ€™t think about. If you can turn all of your portfolio companies that donโ€™t hit that exit velocity, if you can find a soft landing for those companies versus thatโ€™s a writeoff and theyโ€™re dead and done, thatโ€™s extra effort, but thatโ€™s an extra turn on your fundโ€™s performance. There is a skillset in identifying that thereโ€™s still good in a company, even if itโ€™s not going to have this massive outcome.โ€ โ€” Carson Monson

โ€œVenture should play more like Moneyball. If you can get your companies on base and limit strikeouts, that is actually so impactful at a fund level. More emerging managers should try to think like CIOs, and less like individual investors, like being a portfolio manager and managing outcomes. Obviously, venture is a game of minority positions. You do not have sole control. Playing that role for your founders, it impacts performance. It impacts reputation and, in fact, your ability to win in the future.โ€ โ€” Carson Monson

โ€œYou cannot say, โ€˜Iโ€™m going to be SV Angel today, so I can be USV tomorrow.โ€™โ€ โ€” Carson Monson

โ€œA multi-billion dollar mega fund has to have a portfolio of companies whose aggregate equity value outstrips the GDP of most small nations on this planet.โ€ โ€” Carson Monson


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

Underwriting Things That Don’t Change

sequoia tree, does not change

One of the most interesting lines I heard on a podcast that Mike Maples was on was: “90% of our exit profits have come from pivots.” Which I first wrote here. Then here. It’s a line that lives rent free in my mind. Ideas, startups, roadmaps, and goals change all the time. I get it. That’s life. Very, very few folks are folks who unilaterally pursue one thing their entire lives. And of those who do, they’re not all successful.

Another friend of mine whose track record speaks for itself, having invested and involved herself in multiple boards before those companies became unicorns and even after, once told me that the idea she invests in is irrelevant. As long as it has grounds and can be adjacent to a large market. The primary thing she looks for is the founding team.

Early-stage investors obsess about people. They’re not wrong. Some are misled by these “VC-isms.” Others still have their own way of underwriting them. I don’t have a crystal ball. I’m also not the smartest person to be dishing out predictions. I have a rough idea of what will change, though I may not always be right. But I don’t know how they’ll change. Or when. So I’ve lived an investing career obsessing over things that don’t change. Or as Naval Ravikant puts it: “If you lived your life 1000 times, what would be true in 999 of them?”

I’ve written about flaws, limitations and restrictions before. But to quickly surmise:

  • Flaws are things you can overcome. Limited track record. Never managed a team. Never scaled a product. Limited access to capital.
  • Limitations are imposed by others and/or the environment. Gravity dictates that objects don’t fall upward. There are only 24 hours in a day. If you’re not based in the Bay Area, it’s harder to raise capital. Certain investors prefer co-founders and partnerships. Certain investors care about warm intros. The list goes on.
  • Restrictions are rules imposed on yourself by yourself. Batman can’t kill. You only invest in solo founders. You only invest in healthcare. You don’t invest in anyone outside the Ivy League schools. But some restrictions go deeper. You’ll never hire from a job portal again. You never hire or invest outside of your network. You won’t invest or hire having never met someone in person. You need to meet their spouse before you make a hiring decision. You don’t invest in single parents. You don’t hire anyone who doesn’t read at least one book per month. You micromanage. You don’t hire anyone who cannot curse. And yes, I’ve heard all of the above and more. My curiosity is always: Why do you impose such restrictions on yourself? What is the story you’re not telling me? Is out of a fear or admiration?

All that to say:

  • Flaws will and can change if it is a priority. But won’t change if they’re not.
  • Limitations might change, but it’s outside of your and my control. And I don’t get paid to pray to the weather gods.
  • Restrictions often don’t change.

Whether you admit it or not, certain habits are hard to change and unlearn. It’s possible. But that requires you to not only be aware of it, but also actively want to change it. Other habits are second nature. How you treat others. How you start each conversation. Why you look both ways before crossing even an empty street. Why you’ve sold yourself a particular personal narrative. Why you have to invest a certain thesis.

The world seems to always be trying to stay on top of things, but there seems to be far less dialogue around how to get to the bottom of things. To me, when it’s underwriting a person and their team, it’s about underwriting what doesn’t change rather than underwriting what could.

Photo by Hc Digital 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.

Can Your Check Size Win You Board-Level Transparency? | Apurva Mehta | Superclusters | S6E8

apurva mehta

โ€œA manager doesnโ€™t generally fit into their ultimate quartile until Year 6.โ€

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/

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

OUTLINE:

[00:00] Intro
[01:40] Tennis
[02:45] Lehman Brothers’ impact on Apurva
[05:28] What AI is missing in investment management
[14:26] Underestimated qualitative metrics that impact a GP’s story
[22:10] Building Cook Children’s Hospital foundation portfolio from scratch
[30:24] Moving quickly as an LP
[31:32] What does Apurva look for in the first meeting?
[37:20] Ugly sweater Christmas parties
[39:56] Apurva’s favorite ugly sweaters over the years
[41:40] Post-credit scene: What does GFW mean?

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โ€œA manager doesnโ€™t generally fit into their ultimate quartile until Year 6.โ€ โ€” Cambridge Associates

โ€œIf everybodyโ€™s running the other wayโ€”running from the fire, letโ€™s run into it and thereโ€™s an opportunity here.โ€ โ€” Apurva Mehta

โ€œWhen you think about the brand-name firms, they are iconic firms, iconic names. We love the fact that theyโ€™re co-invested alongside us. Even if we could build relationships with those firms, we didnโ€™t feel like weโ€™d get the transparencyโ€”maybe it was because of our check size, but maybe thatโ€™s just because of how they operateโ€”that we needed to go to an investment committee.โ€ โ€” Apurva Mehta

โ€œThe transparency at the brand-name firm level is not as high as it is with the kinds of firms we back.โ€ โ€” Apurva Mehta

โ€œBack then, everything was white space, building around network and ecosystems […] It was easier then because the landscape was less crowded. There were 150 backable or quasi-backable seed funds in 2012. 2000 to 3000 now backable and quasi-backable funds in the market. But it was easier then to figure out what we were looking for because it was just brand new.โ€ โ€” Apurva Mehta


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
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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.

What does GP-Friendly ACTUALLY Mean? | Caroline Toch Docal | Superclusters | S6E7

caroline toch docal

โ€œItโ€™s a mathematical reality that the highest performing GPs in this part of the market often also have the highest kill rates, which means some things are incredible and other things are super wonky and you have to be cool with that. You canโ€™t be doing a six across the board.โ€ โ€” Caroline Toch Docal

Caroline Toch Docal backs early stage fund managers as the lead of BCVโ€™s Emerging Manager Program. She believes in investing in funds as early as the first close, which is a rare focus in the LP landscape. Sheโ€™s a lifelong early stage enthusiast from her time at Venture for America to Techstars to Chief to Dorm Room Fund to now Bain Capital Ventures, where she runs the emerging manager program there which has seen quite the evolution since 2017.

You can find Caroline on her socials here:
LinkedIn: https://www.linkedin.com/in/carolinetoch/
X / Twitter: https://x.com/carolinetoch

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

OUTLINE:

[00:00] Intro
[01:33] BCV Emerge
[02:30] The 13-year summer camp experience
[07:46] From VC to LP
[09:50] Compare/contrast early stage investing to emerging GP investing
[12:51] Behind the scenes of Caroline chose to become an LP
[14:36] Caroline’s first investment
[16:24] What is a GP-friendly diligence process?
[21:27] How Caroline pre-qualifies an investment?
[24:50] Understanding if a GP REALLY believes VC is their life’s work
[26:25] Examples of long-term language
[31:05] The 3 Acts of BCV’s Emerging Manager program
[36:44] What the hell is BGH?
[38:03] Stand up comedy
[39:20] Dogs vs cats

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โ€œOne of the things thatโ€™s not really talked about in this part of the asset class is everything looks pretty good until you see a lot of stuff.โ€ โ€” Caroline Toch Docal

โ€œSometimes people use the referencing phase to get to know people theyโ€™d want to meet. I donโ€™t believe that is necessarily the most GP-friendly thing to do.โ€ โ€” Caroline Toch Docal

โ€œItโ€™s a mathematical reality that the highest performing GPs in this part of the market often also have the highest kill rates, which means some things are incredible and other things are super wonky and you have to be cool with that. You canโ€™t be doing a six across the board.โ€ โ€” Caroline Toch Docal

An example โ€˜long-term languageโ€™: โ€œThey donโ€™t celebrate fundraising; they celebrate outcomes.โ€ โ€” Caroline Toch Docal

โ€œThe average anchor check for a $10-25M fund today is $4.2M. In 2017 when we started, it was less than $3M. So thatโ€™s a huge change. Related, the LP base is just concentrating. Using that same size as a benchmark, they have 25% fewer LPs than in 2020.โ€ โ€” Caroline Toch Docal


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.