2025 Year in Review

2025

“‘I remember’ is more meaningful than ‘I love you.'”

I was catching up with an college friend over the holidays who’s now in a wonderfully happy relationship now, when once upon a time, she once doubted her ability to fall in love again. And as we were talking about what makes this guy special compared to all the other ones, she said: “Because he remembers the small things.”

“I love you”, while great for Hallmark movies, often feels empty if not paired with action. And more often than not, actions speak louder than words. Remembering that whenever they order they pick the carrots out of the salad, so you order salad without the carrots. Remembering their bucket list and making it a quarterly goal to check something off that bucket list.

Separately, I caught up with a friend who runs investors relations (IR) for a large multi-stage firm. Someone I’ve heard from manyโ€”colleagues, LPs, founders, even her friendsโ€”that she is one of the most thoughtful people in the world, which seems to be “easy” for her because she has a great memory and they “don’t”. For a blogpost that will come out next year, we were talking about IR best practices and what her CRM looks like. And I can say it’s accident that she comes off with great memory. There are details she tracks in there that no sane capital formation professional would actively track. One’s go-to coffee order. Their children’s birthdays. Their anniversary. Their first day on the job. And so on. What is that James Clear line again? “You do not rise to the level of your goals. You fall to the level of your systems.”

This past year was a year where I found myself remembering. How I got here. Did I even want to be here? Why did I want to be here? Who helped me get here? What they did? What might’ve seemed like an accident, but was a subconscious habit or intention? Even to the point I’ve asked several guests on the podcast, if they always knew they wanted to be where they are today. How did they know? When did they realize it? Given how personal some of the answers got, we had to leave quite a few on the editing floor. (Sorry.)

I left Alchemist close to the beginning of this past year. 2025 was also the first year since I started where I didn’t share my birthday resolutions on this blog. Largely because I didn’t know if I needed to add more to my list of things to do, but rather subtract things.

And now I’m writing this on the last day of the year, as it felt right to recap on the year only after the year was done. (Almost done.)

Most of my writing this year centralized around LP/GP dynamics. More so than any previous year.

Which is funny. I started this humble blog as a public FAQ. I used toโ€”still doโ€”get quite a few messages often asking for the same advice. I’ve always disliked giving general advice. A piece of advice is only as great as the situation in which you use it in. But most people ask generic questions. And generic questions often get generic advice. Nevertheless, I’ve always erred on the side of sharing the circumstance in which the advice is given when I do share generic advice, except when the advice, in my experience, applies to most people I talk to. And it’s funny that of this year’s most popular blogposts, four definitely include generic advice. Two arguably more circumstantial. But proportionally, even looking back at my most popular blogposts, the furthest reaching ones often house FAQs that most people can relate to. Or know someone that can relate to it.

Without further ado, my most popular pieces of writing this year:

  1. Hustle as a Differentiator โ€” I don’t know how ‘hustle’ went up in search volume this year, but it did. At least in terms of how people found this essay. But I also think people like stories and tactical examples of when and how hustle beat everything else. And this is the blogpost for that. Also, the only one of the top six not written this year.
  2. If 198 Pieces of Unsolicited, (Possibly) Ungooglable Advice for Founders Were Not Enough โ€” The third installation of my 99 pieces of tactical founder advice series. Admittedly, not surprised this went far. Sometimes great content is hard to find. And every time I publish a collection, like this, I hope it becomes the Dewey Decimal Classification for good, tactical content in the innovation ecosystem.
  3. Dear LP โ€” I wrote the sister blogpost of this first. But an emerging manager asked me to write that calls LPs out on their bad behavior. Not a good reason to write a piece in my opinion, until the subsequent weeks’ worth of LP conversations left me frustrated at LP behavior myself. This is also the blogpost where I had more than a handful of friends reach out to ask if I was okay. Which I was and am. This essay was the therapy I needed.
  4. Good Misses and Bad Hits โ€” Most outcomes in venture aren’t clear until a decade later. And when they are, so much of our past memory atrophies that for many of us, we can’t pattern match to why we made the decisions we did. Inspired by our Golden State celebrity, we decided to write a piece on what it means to measure inputs before the outputs and how we can course correct before it’s too late.
  5. Dear Emerging Manager โ€” Born out of frustration with emerging managers who seem to be living under a rock. But also a realization that not every GP has the vantage point that LPs do. In fact, most don’t. So this letter was hopefully helpful to debunk some of the myths GPs have.
  6. Goldilocks and the 3 Secondaries โ€” One of my favorite pieces I co-wrote this year with Dave, as it is one of the most tactical and intellectually rigorous pieces this year, but also a great mathematical exercise of how much of your private stake in a company to sell, when, and to whom.

2025 was the year I took a step back from promoting any of this blog’s content online. I also took down any vestigial pages that asked for a subscription within the first 10 seconds of browsing a page on this blog. I simply wanted this blog to be my safe harbor, my personal diary on my journey week by week. I realized that every time I actively promoted my blog on social media, I felt a part of me die.

Unlike Superclusters, this blog isn’t meant for one particular audience. While this blog has grown over time and I’m thankful to each and every one of you who has joined me in this journey, and while I had many an opportunity to do a sponsored blogpost, selling any piece of this virtual real estate felt disingenuous. It felt that I was selling a part of my soul. Because every week when I write, I write about whatever I want to write about. I don’t have an agenda. I merely write to write.

And the way I felt most true to myself was to no longer pursue any marketing of this blog. The only reason any of the afore-mentioned blogposts in the last section made its way to new audiences is that I’m lucky to have readers like you share things with the world, while I’ve hermitized.

As such, any growth of this blog this year is because of you, not me. For that and more, I am deeply thankful. Nevertheless, the all-time most popular blogposts haven’t varied much compared to last year, except for our lucky number five. Interestingly enough, I didn’t even write that one this year.

  1. The Science of Selling – Early DPI Benchmarks โ€” Honestly, it still surprises me that this is my most popular one to date. Not because I think it’s a bad topicโ€”in fact, I truly believe it’s a much needed discussion as venture funds face liquidity crunches and the asset class institutionalizesโ€”but because, I think it’s still a niche topic that is not widely searched for. But I’m glad that people are searching for answers here. This one also led me to write its sister piece here, which ranked 6th for this year’s most popular.
  2. The Non-Obvious Emerging LP Playbook โ€” My first piece that felt like it went viral. And the one that taught me how much dialogue is needed in this world around investing in venture funds.
  3. 10 Letters of Thanks to 10 People who Changed my Life โ€” Another surprise that this topic of gratitude is as enduring as it is. Hopefully, this will play a small part in helping create a more grateful world. We stand on the shoulders of giants. It’s always important to never forget that fact.
  4. 99 Pieces of Unsolicited, (Possibly) Ungooglable Startup Advice โ€” The OG collection I put together on 99 pieces of tactical advice for founders. This is the one that led to the one I wrote for investors, and all future series under the ’99’ nomination.
  5. Hustle as a Differentiator โ€” Only a matter of time that this one beat out the one I wrote about how to host fireside chats. ๐Ÿ™‚

It’s always deeply interesting to me that sometimes the blogposts I spend the most time writing and/or are the ones that resonate with me the most personally don’t always go the furthest. A constant reminder that what the world might like, what you might like, may vary from what I like. From time to time, I get small notes from you that an esoteric, but deeply personal blogpost peaks your interest. And it really makes my day. For a very brief 24 hours, if only to relish in the small joys in life, I save those notes for when I feel imposter syndrome. Trust me, it happens. Not because the readership is highest, but because it’s nice to know I’m not alone in my peculiar, sometimes really nerdy interests.

The below I will list, in no particular order, as each meant something to me at the time of writing each, as well as moving forward:

  • Goldilocks and the 3 Secondaries โ€” Same rationale as above. And if you want the actual model we used to model when and how much to sell on the secondary market, it’s in there.
  • Flaws, Restrictions, and Limitations โ€” Inspired by Brandon Sanderson’s framework for character development, I’ve found this framework quite useful when assessing how risky an investment is into an emerging manager.
  • Dear LP โ€” Pure therapy.
  • Dear Emerging Manager โ€” Same as the above. Free therapy for myself. Hopefully helpful to the world.
  • The Question Off โ€” One of my favorite drills I did this year to be a more thoughtful conversationalist, with none other than the best sparring partner out there, Kevin Kelly.
  • On Re-Ups โ€” I’m an emerging LP. I haven’t been allocating to venture funds for over a decade, and so I’m still learning. This year, for the first time, I had managers I invested in, in previous vintages, come back and ask for me to re-up. Rather than do so haphazardly, I had to build a system for when it makes sense for me to re-up. This is it.
  • Gratitude and Deal Flow โ€” One of my favorite re-framings on who I choose to invest in. And I couldn’t spell out why I liked certain managers over other great ones until a friend spelled it out for me.
  • Intro Policy โ€” Another piece for personal therapy. Since writing this, it’s been much easier for myself to decide when to make intros.
  • 300 WhatsApp Messages Later: Our Risk Framework for Backingย Emergingย VCs โ€” One of the beauties of collaborating with someone brilliantโ€”I’m looking at you, Benโ€”is that I learn something new as I am writing this alongside my co-author. Iron sharpens iron. And it was through this piece, that I built a more robust risk framework to evaluate emerging managers.
  • Scientists, Celebrities and Magicians โ€” Kudos to my friend, Michael, for teaching me his framework for how a professional can be a triple threat, which I’ve since applied to the world of venture. And how different investors and leaders spike.
  • Referencing Excellence โ€” The more I invest as an LP, the more important I realize how important reference calls are. The more important I realize they are, the more I realize I need to refine the way I get to the truth. Unfortunately, there’s no silver bullet, but this blogpost led me down my first real personal exploration for how to do references my way.

There is but one personally memorable blogpost I will intentionally leave out of the above list. It is the only one I’ve gone back to edit not once, not twice, but four times this year. Let’s call it an easter egg. If you do find it somehow, just know that I plan to continue updating that piece next year as well.

Photo by Kelly Sikkema on Unsplash


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


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.

Peter Walker as You’ve Never Seen Him Before | Peter Walker | Superclusters | S6PSE3

peter walker

โ€œYouโ€™re making decisions in an incomplete vacuum. What I think many people should do more of, in terms of those mental models, is frame it in the reverse. Which of these decisions am I going to make that is the most regret-minimizing? That I have the least likelihood of regretting later on in life, assuming that in most cases, I will be wrong.โ€ โ€” Peter Walker

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 VC and startup world. This episode, it’s with my man, Peter Walker, who creates some of the industry’s most talked charts and graphics around the ebbs and flows of tech innovation.

Peter Walker runs the Insights team at Carta, where he works to make startups a little less opaque for founders, investors, and employees. Prior to Carta, he was a marketing executive for the media analytics startup PublicRelay and led a data visualization team at The Atlantic magazine. He lives in San Francisco, but you can find him on LinkedIn (see links below).

You can find Peter on his socials here:
LinkedIn: https://www.linkedin.com/in/peterjameswalker/
X / Twitter: https://x.com/PeterJ_Walker

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

OUTLINE:

[00:00] Intro
[02:52] Peter’s first brush with entrepreneurship
[11:49] 996 work culture
[17:11] Peter’s disclaimer on his data
[21:27] Regret-minimization when investing
[24:24] One example of regret-minimization
[26:07] How does Peter choose which conferences to go to?
[29:33] Conference panels are often bad
[36:22] The incongruencies of what GPs say publicly and privately
[41:43] Peter’s first data visualization
[44:18] Why is soccer underrated in the US?
[46:10] What great lengths has Peter gone for his friends?
[48:21] One worrisome trend we’re going to see in 2026
[52:18] One optimistic trend to look forward to in 2026

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œNo one has to force you to work long hours if you really want to. The founders and early employees who push hardest arenโ€™t usually doing it because someone set the office lights to stay on until midnight. Theyโ€™re doing it because they care. Itโ€™s not obedienceโ€”itโ€™s compulsion.โ€ โ€” Cristina Cordova

โ€œThereโ€™s a growing recognition that that sense of compulsion, it very rarely lasts for 10 years. […] Itโ€™s very rare to find that one thingโ€”that one set of problemsโ€”that can get you so excited for your entire life.โ€ โ€” Peter Walker

โ€œCuriosity is the art of asking questions where youโ€™re not married to the answer.โ€ โ€” Matt Huang

โ€œYou should probably, if youโ€™re a founder, for instance, selectively ignore at least half of what Iโ€™m saying because it doesnโ€™t apply to you. And your job as a founder, your job as an investor, your job as a thoughtful person is to figure out which half.โ€ โ€” Peter Walker

โ€œIf you torture the data long enough, it will confess to anything.โ€  โ€” Ronald Coase

โ€œYouโ€™re making decisions in an incomplete vacuum. What I think many people should do more of, in terms of those mental models, is frame it in the reverse. Which of these decisions am I going to make that is the most regret-minimizing? That I have the least likelihood of regretting later on in life, assuming that in most cases, I will be wrong.โ€ โ€” Peter Walker

โ€œThe worrisome part is that sometimes [selling founder secondaries] is at pretty early-stage companiesโ€”seed, A. Sometimes, itโ€™s for $10,000 and I donโ€™t know what happened there. Sometimes, itโ€™s for a really sizable amount of moneyโ€”seven figures. To me, that is a bubble sign. That is as close as you can get to capital is chasing consensus too much, and therefore, smart founders are just taking advantage and taking stuff off the table.โ€ โ€” Peter Walker


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
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Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

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.

The Third Leg of Firm-Building

marathon, race, third leg

Five years ago, I wrote a piece about the third leg of the race. From my time as a competitive swimmer, the lesson our coach always had for us was if you’re swimming anything more than two laps, the most important part of every race is the third leg. Everyone’s tired. Everyone’s gasping for air. Yet everyone wants to win. The question is who wants it more. And by the time you get to a decently high level, everyone’s athleticism is about the same. All that matters is the mentality you have on that third segment of four of each race.

We often say, that starting a company or a fund is a marathon, not a sprint. True in a lot of ways. But also, it’s a series of sprints within a marathon.

We put out an episode last week with the amazing Ben Choi, which I really can’t stop recommending. Just because I learn something new every time I talk with Ben, and this time especially so. But that’s my own bias, and I get it. But more interestingly, he said something that I couldn’t get out of my mind since we recorded. “The first three fundsโ€”not just the first two, the first threeโ€”are that ‘working-out’ process. Most pragmatically, there’s very little performance to be seen by Fund III. So it’s actually Fund IV for us to hold up the manager as no longer emerging and now needs to earn its own place in the portfolio.” The timestamp is at 16:21 if you’re curious.

And it got me thinking… is Fund III that third leg of the race?

When most GPs raise Fund III, they’re usually four, maybe five years, out from their Fund I. And that’s assuming they started deploying as soon as they raised their fund. And within five years, not that much changes. Usually, that’s two funding rounds after your first investments. But lemons ripen early, so only a small, small subset move to Series A or B. Most have raised one or less subsequent round since the GP committed capital.

Even accounting for two funding rounds later, that’s usually too early to consider selling into the next round. And if one does (unless it’s a heavily diversified portfolio and the GP has no information rights, and somehow is so far removed from the company that no one at the company talks to the GP anymore), then there’s signaling risk. Because:

  1. No matter what portfolio strategy you run, not staying in touch with your best performing companies is a cardinal sin. Not only can you not use those companies as references (which LPs do look for), you also can’t say your deal flow increased meaningfully over time. No senior executive or early employee knows who you are. So if they leave the company and start their own, they wouldn’t pitch you. Your network doesn’t get better over time. See my gratitude essay for more depth here.
  2. Not having any information rights and/or visibility is another problem. Do the founders not trust you? Do you have major investor’s rights? How are you managing follow-on investment decision makingโ€”whether that’s through reserves or SPVs? Are the blind leading the blind?
  3. And if you do run a diversified portfolio, where optically selling early may not be as reputationally harmful to the company, you are losing out on the power law. And for a diversified portfolio, say a 50-company portfolio. You need a 50X on an individual investment to return the fund. 150X if you want to 3X the fund. As opposed to a concentrated 20-company portfolio, where you only need 20X to return the fund and 60X to 3X. As such, selling too early meaningfully caps your upside for an asset class that is one of the few power law-driven ones. As Jamie Rhode once said, โ€œIf youโ€™re compounding at 25% for 12 years, that turns into a 14.9X. If youโ€™re compounding at 14%, thatโ€™s a 5. And the public market which is 11% gets you a 3.5X. [โ€ฆ] If the asset is compounding at a venture-like CAGR, donโ€™t sell out early because youโ€™re missing out on a huge part of that ultimate multiple. For us, weโ€™re taxable investors. I have to go pay taxes on that asset you sold out of early and go find another asset compounding at 25%.โ€ Taking it a step further, assuming 12-year fund cycles, and 25% IRR, โ€œthe last 20% of time produces 46% of that return.โ€ And that’s just the last three years of a fund, much less sooner.
  4. Finally, any early DPI you do get up to Fund I t+5 years is negligible. Anything under 0.5X, and for some LPs, anything sub-1X, isn’t any more inspiring to invest in than if you had absolutely no DPI.

Yet despite all of the above, the only thing you can prove to LPs are the inputs. Not the outputs. You can prove that you invested in the same number of companies as you promised. You can prove that you’re pacing in the same manner as you promised. And you can prove that founders take the same check size and offer the same ownership to you as you promised. And that is always good. As you raise from friends and family and early believers in Fund I, Fund III’s raise usually inches towards smaller institutions, but larger checks than you likely had in Fund I.

  1. Fund-of-funds care about legibility. Logos. Outliers. Realistically, if you didn’t have any before Fund I, the likelihood of you having any while raising Fund III is slim. They need to tell a story to their LPs. A story of access and getting in on gems that no one else has heard of, but if everyone knew, they’d fight to get in.
  2. Any person you pitch to who has any string of three to four letters (or is hired to be a professional manager) attached to their name (i.e. MBA, CAIA, CFA, CPA, etc.) has a job. For many, their incentive unless their track record speaks for itself (likely not, given how long venture funds take to fully return capital) is to “not get fired for buying IBM.” Some of their year-end bonuses are attached to that. Some lack the bandwidth and the team members to fully immerse themselves in the true craft of emerging manager investing. Many times, the incentive structure is outside of their immediate hands. For every bet they make that isn’t obvious, they risk career suicide. At least within that institution.

I’m obviously generalizing. While this may be true for 90%+ of LPs who fit in these categories, there are obviously outliers. Never judge a book by its cover. But it’s often helpful to set your expectations realistically.

As such, despite not much changing from your investment side, from the eyes of most LPs, you are graduating to larger and larger LP checks. Usually because of the need to provide more proof points towards the ultimate fund strategy you would like to deploy when you’re ‘established.’ But to each new set of LPs, prior to an institutional 8-year track record, you’re still new. On top of that, as your fund size likely grows a bit in size from Fund I, to some LPs, you are drifting from your initial strategy by no longer being participatory and now leading and co-leading. You also might have added a new partner, like Ben talks about in the afore-mentioned episode. And a new strategy and a new team requires new proof points related to on-thesis investments. So, Fund III is where you begin to need to whether the storm. For some, that may start from Fund II. Altos Ventures took four years to raise their Fund II. Many others I know struggled to do the same. But if you really want to be in VC long term, this is the third leg of the race.

And this is when a lot of GPs start tapping out. Will you?

Photo by Victoire Joncheray 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.

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.

50% of Your Portfolio Will Be Opportunistic

clover, luck, opportunistic

50% of a fund’s portfolio will come from predictable, hopefully, scalable sourcing mechanisms. It’s the community you run. The events you host. The newsletter you write and the podcast you moderate. It’ll come from existing networks that you’ve built trust with. Prior companies. Collegiate classmates. And geographical proximity.

50% will be opportunistic. Sitting next to a founder in coach. Standing in line at a coffee shop waiting for your friend, only to strike up a conversation with someone who’s been waiting even longer than you have for their friend. That friend of a friend’s spouse’s sister’s cousin you meet at your neighbor’s holiday party. Sitting next to someone who also is the proud parent of a Rottweiler at the dog park.

As such, only half your portfolio can be underwritten by an LP. Half will hardly be able to (with rare exceptions based on fund strategy). And that’s okay. Venture is a game of outliers. You need to increase the surface area for serendipity to stick. As long as most of your opportunistic deal flow is on-thesis. All in all, no more than 10% of your deals should truly be off-thesis. 20% if you have generous and/or venture-literate LPs, which often means their fund-of-fund portfolios are younger and still growing.

But of all the opportunistic deal flow out there, being open-minded of such opportunities is imperative. If you fish, you need to know when to reel it in. If you farm, you need to know when the crop is ripe enough to harvest. If you hunt, you must chase the game.

If you’re a fisher…

  • Build content libraries at scale. Increase the surface area for serendipity to stick. Meaningful and engaged distribution matters more than anything else. In an age of ephemeral attention, decide if you want to create ephemeral content (i.e. news, updates, trends) or evergreen content (i.e. timeless lessons, things that don’t change, classics). Do you want to stay on top of things or get to the bottom of things? The former requires you to stay on the rat wheel, else you disappear into obsolescence.
  • Stand for something. The hill you’re willing to die on must be unique to you, where most people would disagree. But then, you’d be the n of 1 for that belief. Highly optimized for those seeking such a perspective.
  • Host events. Stay top of mind.
  • Build super-connector networks. For some, that’s a scout program. For others, it’s a venture partner one. And others still, an emerging manager fund-of-funds.

If you’re a farmer…

  • Be more helpful than people would assume makes sense.
  • Get/stay involved in networks of aspiring entrepreneurs.
  • Nurture teams and help founders actively attract the best talent and the most enduring customers.
  • Work with founders and ecosystem builders who know how to be grateful. Do not lose the fruits of your labor because no one gave you a chance to harvest them, including yourself.

If you’re a hunter…

  • Move fast, close fast.
  • Be mobile. Be ready to meet your founders where they are at. Even if that means buying a flight out the next day. When everyone else uses a scheduling assistant and sits on Zoom, capitalize on in-person interactions with haste.
  • Know what you’re looking for before you find what you’re looking for, so that when you do come across one, even accidentally, you will have reached conviction before others have gotten to a first meeting.

Of course, most managers are often some permutation of the three. Rarely are they only one. And if they are, they are undeniably the industry’s best in each. Dare I say, as an emerging manager, it is better to spike in one than to just be proficient in all three.

Photo by Peter Burdon 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.

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.

Woe is Me

sunset, alone, dock, woe

I was talking to an emerging manager raising a $10M fund recently. He shared a comment, likely off-the-cuff, but something I’ve heard many other emerging managers echo. “This year, most of the dollars deployed into venture has concentrated in only a few big funds.”

Not this manager in particular, but I’ve heard so many other Fund I or Fund II GPs say that. Blaming their struggle with fundraising on the world. It’s not me, but the world is conspiring against me. Or frankly, woe is me. But there is no LP who ever wants to hear that. Building a firm is hard. Building a startup, likely harder. No one said it’ll be easy. So let’s not pretend it’ll be all sunshine and rainbows. If you thought so, you’re deeply misinformed. If you’re going to be an entrepreneur of any kind, you need to take matters into your own hands. You cannot change the world (at least not yet). But you can change how you approach it.

And as an LP, that’s the mentality we’re looking for. Or as Raida Daouk once said on the pod, we like “GPs who can run through walls.”

That said, the mega funds who are raising billions of dollars are raising from institutions whose minimum check size is in the tens, if not hundreds of millions. These same institutions would never invest in an emerging manager. Their team, their strategy, and their institution isn’t built for it. When they have to deploy hundreds of millions, if not billions, a year into “venture” with a team of four or less, you’re not their target audience. So as an emerging manager, those mega funds are not your competition at least when it comes to LP capital.

You’re competing against all the other funds (likely emerging managers) at your fund size. Who can take the same check size you can take. That’s who you’re competing with. So whether you like it or not, billions going to the mega funds has, from a fundraising perspective, nothing to do with you.

If you are looking for reasons to fail, you will find one.

As the great Henry Ford once said, “Whether you think you can, or you think you can’t, you’re right.”

Photo by Johannes Plenio on Unsplash


#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. Itโ€™s not designed to go down smoothly like the best cup of cappuccino youโ€™ve ever had (although hereโ€˜s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.


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.