The Value of Being an Outsider

fence, inside, outside

In 1968, NASA tasked the late George Land to create a test that would help NASA hire more creative geniuses. Does genius and creativity come from nature or nurture? As such his job was to create a test so simple that even children could take it. And he found that for children ages 4-5, out of 1,600 children, 98% of them qualified to be a genius. Divergent thinkers. Then, he waited five years to assess these same children. To which he found, only 30% qualified. Then another five years later, only 12% of the same children were what he counted to be geniuses.

It begged the question: What percent of adults are geniuses?

The answer, 2%.

For those curious, I’d highly recommend George’s 2011 TEDx talk about the topic.

Of course, the lesson from all of this is the fallacy of modern-day education. And the same is true for the adult world between convergent thinkers and divergent thinkers. I believe in the world of venture at least, we have terminology that’s little less palatable (at least for me, although on occasion I’m guilty of using them myself): insiders and outsiders.

My friend Anne sent me this piece by Auren Hoffman recently on insiders and outsiders. An incredibly well-written piece, and quite thought-provoking. I’ve largely thought about how outsiders can become insiders, but silly me, less about the value of staying an outsider or an insider aiming to become an outsider. Moreover, that to be successful as an insider, there’s actually a rather predictable path to become one. Or at least to help your children become one. Go to Harvard. Play insider sports, like gold, or horse-riding, or sailing. And son. But in Auren’s words, to be successful as an outsider, well, “being [an outsider] is MUCH higher beta. They could end up changing the world for the better. They also could blow it up. Or just never be accepted and live less happy.”

And while I may not agree with everything that Auren proposes, a lot of it makes sense. In fact, 11 words definitely caught my eye. “Outsiders take things from insiders.  Insiders inherit things from other insiders.” And as such, insiders play the status quo; outsiders change the status quo.

It’s interesting. Every generation of VC, there’s a changing of the guard. Many of the new regime are outsiders. People who think different. People who exhibit a level of creativity that is uncommon in VCs. Either in the form of business models or how they provide value. How they build brand. Or simply how their brain works. People that in bringing a fresh perspective were able to find the next great companies unlike any other.

Interestingly enough, in my buddy and Superclusters guest Jaap’s recent study of 2,092 North American and European VC funds, he found that these are the folks who are more likely to hit fundraise targets than any other GP persona. Aka 45% success rate. And perform highest at 2.4X net TVPI, but only average on DPI and IRR.

Source: Jaap Vriesendorp’s cluster model on 2,092 VC funds. Find a more interactive one here.

My guess here is that these outsiders, in being artisanal about their craft and — well, at least with respect to the VC industry at large, divergent thinkers — find their tribe rather quickly because LPs quick self-select themselves in or out of a relationship with them. They’re the round pegs in the square holes, to borrow a Steve Jobs moniker. So when most others look square, the few round holes instantly identify with these round pegs. And more often than not, they’re new to the asset management game, so have lower fund targets and a more precise strategy. Downside to that is they’re still learning the ropes of exit strategies and fund management. Which also explains the high volatility in returns.

And while there’s much higher beta in being an outsider, there’s plenty of research to suggest that there is also greater alpha. But it’s going to be unfair. The deck is rigged against you. There’s a great Marcus Aurelius line. “Mental toughness is knowing life isn’t fair and still playing to win.”

The outsiders who win exhibit exactly that mental fortitude against stacked odds. Besides, there’s joy in doing things differently.

Photo by Randy Fath 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.

Why Trust is Built from the Small Things | Ben Ehrlich | Superclusters | S3E8

Ben Ehrlich is the founder and General Partner of First Momentum Capital, where he helps seed a new generation of venture capital firms. He is also the Director of Strategy at the Long Term Stock Exhange. Previously Ben worked across the venture ecosystem supporting companies in the Canadian Technology Accelerator, OutCast Communications and Cribspot (YC 15). In his free time Ben takes his Irish setter doodle hiking and enjoys watching the University of Michigan football team (mostly) win.

You can find Ben on his socials here:
Twitter: https://x.com/benjaminehrlich
LinkedIn: https://www.linkedin.com/in/benjamin-ehrlich-43b75498/

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

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[03:43] The origins of the Out of the Crisis podcast
[06:54] Ben’s advice for rookie podcasters
[08:35] How did Ben first meet Eric Ries?
[11:46] The play-by-play for Ben’s interview with LTSE
[13:36] What do decisions and conversations look like at LTSE?
[16:23] Building trust among team members
[18:29] How does Ben build trust with GPs?
[25:14] How did First Momentum Capital start?
[30:42] What was the pitch to close First Momentum’s first fund?
[33:54] How does Ben underwrite Fund I managers?
[36:42] How does Ben measure a GP’s future deal flow (as opposed to today’s)?
[45:40] What does a “No” from Ben look like?
[57:50] Thoughts on fund governance
[1:05:57] What is the role of serendipity in Ben’s life?
[1:08:17] Commisso Bakery in Toronto
[1:10:35] Thank you to Alchemist Accelerator for sponsoring!
[1:11:35] If you enjoyed the episode, I’d appreciate it if you could share it with one friend!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Make sure to pay the government, doctors, and podcast producers on time.” – Ben Ehrlich

“If you want to build trust with someone [on your team], if they screw up, you have to be okay with them screwing up because you put them in the situation.” – Ben Ehrlich

“We’re looking for concentrated, non-correlated bets.” – Ben Ehrlich


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
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What Limited Capital Does to Founders and Investors

pitch, presentation

My friend invited me to a demo day earlier this week. Albeit, it was a bunch of summer interns presenting their project they’d been working on for the last two months. The few investors and I who sat on the judging panel were all admittedly quite surprised by the quality of pitches and products from students and hell, even within two months. In fact, these 10-11 interns have gotten much further in product development and customer discovery than most founders I’ve seen across the span of a year. Whether sampling bias or not, the latter is probably about 50%+ of what I see these days. And you’d think that AI would have sped up the product development cycle.

But I digress.

Simply put, I was impressed. So, in efforts to simulate actual pitches at demo days, I asked a team who had presented five features they’d been working on and gotten each to a working prototype. “If you had to kill three of the five features, which three would you kill?”

To which, the “CEO” replied: “To be honest, all five are quite important. But if we had to kill a feature, it’d be the AI chatbot, but the rest of the four go hand-in-hand.”

I pushed for a more discerning answer, but was met with a paraphrased version of the last answer. And of course, it left a little more to be desired. What I was looking for was something of more prescriptive specificity. For instance, “we’d focus on usage metrics, particularly with respect to retention cohorts and actions per session across all the features. And depending on what features seem to perform better than others, our plan is to focus 70% of engineering resources on the top feature, 20% on the second most popular feature, and 10% focused on either a permutation of the other three or spending time with our customers to see where they’re the most frustrated.” It may not need to be the “right” answer, but having a thought-out answer is helpful.

After all, the original question boils down to the fact that most founders fail from indigestion not from starvation. Charles Hudson wrote this great piece last month, aptly named “The Last $250K.” In short, one of the most common behavioral changes he’s observed is when founders are down to their last $250K. And, three things stand out in particular:

  1. “The most important things to work on become incredibly clear.”
  2. “The data needed to validate the company’s hypothesis becomes much clearer.”
  3. “There are things that the company was doing that they stop doing because those things don’t really matter given the gravity of the situation.”

It’s a quick read. And I highly recommend it. Much of which I personally agree with. Not sure if that’s usually the $250K mark, but my personal sample size is far smaller than Charles’. Constraints are the breeding grounds of creativity.

What’s really interesting is that my first reaction to that blogpost was just like how the last 4-6 months of runway leads to deep focus, how do the last 4-6 months affect fund managers? And it’s not too far off.

  • Deployment speed slows. The simple reason is that they no longer feel the fire under their belly to deploy. Either because they’re close to their target portfolio size or they need to elongate the time horizon while they’re actively raising their next fund.
  • The quality bar for what gets funded goes up. Since your deal flow pipeline is likely not contracting, there’s a flight to quality. And quality more often than not, translates to traction, logos/brands, and founder’s prior experiences. While there are always outliers, I see many GPs take less risky bets that they would’ve otherwise.
  • GPs are actively planning for the next fund’s strategy. And actively synthesizing lessons learned. Or at least, with respect with how they pitch LPs. And if they’re an emerging manager, or a fund without clear wins in their last fund, the most important things also become painfully clear. They often focus on the 20% that drove 80% of fund returns.
  • GPs are spending a lot more time on portfolio support. Not only because graduation rates become a lot more important (for fund returns and narratives for prospective LPs), but also because references matter in diligence. And well, if you’re fundraising for your next fund, you can be damn well sure that a sophisticated LP is going to do anywhere between 10-50 reference checks. On-list and off-list. 20-30% of which with your portfolio companies.

Thematically, focus. While there are other constraints that help improve a founder or a fund manager’s level of focus, limited runway (or capital to deploy) is a natural forcing function. The best ones I’ve seen often impose artificial constraints early on, before things get rough. Rules and codes of conduct. Things they promise themselves and the team never do. Aligning compensation behind performance. In other words, operational discipline.

Naturally, it should be to no surprise that investors of any kind spend a lot of time on organizational discipline before they choose to invest.

Photo by National Cancer Institute 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.

An Inside Peek into the Mind of an Individual LP | Susan Kimberlin | Superclusters | S3E7

Susan Kimberlin builds and invests in things that are Good & Useful. She is an angel investor, limited partner and product leader with a career that is equal parts building SaaS software products, and investing in companies, funds, teams, and projects that promote social equity with practical solutions for real-world problems. She is committed to bringing more diverse people into investing and the innovation economy. With a background in building search and natural language products for companies like PayPal and Salesforce, she leverages her experience to help her portfolio companies with product and fundraising strategies. Susan believes that bringing diverse perspectives to creative and practical challenges is the best way to create durable and impactful change.

In addition to her tech roles, Susan co-owns and manages Tammberlin Vineyards, growing Rhône wine varietals in Bennett Valley, Sonoma County. She works on documentary and narrative film projects as an executive producer, supporting creative projects that raise awareness, start conversations, and bring joy. She is a lifelong singer, and has been singing with pop a cappella group The Loose Interpretations for nearly 20 years.

You can find Susan on her socials here:
Twitter: https://x.com/susansearchpro
LinkedIn: https://www.linkedin.com/in/susankimberlin/
Substack: https://goodanduseful.substack.com/

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

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[02:51] What are madrigals?
[10:10] How to balance high expectations for your team and the trust that they will get there
[14:53] How does Susan recognize drive and excellence in others?
[21:49] What made Susan’s founding LP check in Backstage Capital so unique?
[26:01] Difference between LP stakes and GP stakes
[38:51] The smokes and mirrors behind the first pitch
[43:54] Susan’s investment strategy as an individual LP?
[50:21] What topic would Susan give a TED talk in that’s not startups or venture?
[59:24] Thank you to Alchemist Accelerator for sponsoring!
[1:00:25] If you enjoyed this episode, could you share this with one other friend?

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Communication between us is the definition of our experience in the world.” – Susan Kimberlin


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

The Art and Science of Reference Checks | Raida Daouk | Superclusters | S3E6

raida daouk

Raida Daouk started her career in banking before moving to the investment team of BY Venture Partner, a venture fund with offices in Beirut and Abu Dhabi. She quickly climbed the ranks within the company and ultimately became a Venture Partner.

Recognizing a void in the market for personalized venture consulting services, Raida established Amkan Advisory, a boutique consultancy firm specializing in assisting family offices and high-net-worth individuals in identifying venture funds that align with their specific strategies. Given that first-time fund managers often possess the most aligned incentives with their investors, she understood the significant value they bring to the venture capital landscape. However, Raida also understood the reluctance of family offices to commit capital to relatively unproven managers. By curating a portfolio of carefully selected funds, she aims to mitigate the perceived risk associated with investing in first-time managers while still accessing the high-growth potential of emerging ventures.

Amkan Ventures emerged to offer LPs access to emerging managers beyond their direct reach. Focusing on small Funds I and II led by ambitious managers with a conviction-driven approach, the firm prioritizes delivering returns and nurturing opportunities in the venture arena.

Amkan Ventures’ first close occurred in April 2024, with one investment already made in a $30M fund I out of NY and one more about to be announced.

Raida currently serves on the Selection Committees of RAISE Global and The Bridge Platform.

You can find Raida on her socials here:
LinkedIn: https://www.linkedin.com/in/raidadaouk/
Amkan Ventures: https://www.amkanventures.com/

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

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[02:45] The impact of biology on Raida’s career
[06:24] If Raida were to teach a founder psychology course
[08:42] Raida’s definition of “running through walls”
[10:16] Similarities and differences between founders and fund managers
[11:36] What does GP-thesis fit look like?
[14:38] How Raida got to a yes on Nebular Ventures?
[20:35] The personas of different kinds of references
[26:05] The one question that Raida always asks during reference calls
[28:31] Is there such a thing as too many references?
[31:57] What if you don’t have a network of references as an LP?
[35:26] How does one set up the venture arm of a family office?
[40:28] What is the GCC?
[43:58] The best way to build relationships in the GCC
[47:54] The origin story of Amkan Ventures
[52:19] How did Raida build a strong understanding of the foodtech space?
[53:58] Where did Amkan’s name come from?
[58:26] What fund is in Raida’s anti-portfolio?
[1:00:30] What’s Raida’s take on solo GPs?
[1:03:10] How does your mindset change as an LP if you had evergreen capital?
[1:06:58] Thank you to Alchemist Accelerator for sponsoring!
[1:07:59] If you enjoyed this episode, it would mean a lot if you could share this with one other friend!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“It’s always best to start the relationship when there is no ask.” – Raida Daouk

“The average length of a VC fund is double that of a typical American marriage. So VC splits – divorce – is much more likely than getting hit by a bus.” – Raida Daouk

“The more constraints you have, the more conviction you will have in each manager.” – Raida Daouk


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

DGQ 22: If you were hiring someone underneath this person, what skills would they have?

hire

I’ve had Harry’s episode with Peter Lacaillade under my saved episode list on Spotify for a long minute. And Benedikt Langer‘s semi-recent piece on Embracing Emergence finally got me over the activation energy to listen to it. (Sorry, Harry)

But I’m so glad I did. In it, Harry shared a question he likes asking “If we were hiring someone underneath me to support him, what skills would they have?” In many ways, it’s the same as another question Doug Leone shared on his podcast as well. What three adjectives would you use to describe your sibling?

It comes down to simple purpose of trying to ask about someone’s weakness without asking them “what’s your weakness?” Why does it matter? When you’re too forward with your question, say the weakness one, recipients always end up finding ways to explain their “weakness” as a byproduct of their strength, or not really sharing a true weakness. “I’m too honest.” “I work too hard.” And so on.

While the above set of questions may not work for everyone, and probably even less so now that Harry and Doug shared it in a public arena, I can’t help but appreciate the linguistic gymnastics to find the right combination of words that gets one the answer they want. Nevertheless, I’m sure there are many more on this planet who still have yet to be exposed to those questions.

Similarly, I find it to be a damn good question to ask when doing references on potential investments. The truth is every founder or GP one invests in will have weaknesses. And that’s okay. Everyone’s a human. But in reference calls, there are two hurdles that one most overcome in their diligence:

  1. Getting the reference to share an honest assessment of the person they know. This is especially hard when these are on-list references. In other words, references that the person being diligenced is providing themselves. Naturally, this list is full of people who are almost guaranteed to say positive things about said individual. Besides, there is absolutely no incentive to badmouth another person. Neither do most people aim to do so.
  2. How high on the priority list is this person’s weakness? Can I get conviction on this deal even if I were to accept this weakness? Does it matter as much in a Fund I? Fund II? Fund III? If they need to hire someone to fundraise for them, is that a question of ability or network? And how crucial is it not only to the firm’s survival, but also their outperformance? If they need to hire someone to manage their calendar, that may be lower on the priority list of risks for most LPs.

Nevertheless, I find Harry’s question a great one to ask former colleagues, occasionally portfolio or anti-portfolio founders.

Photo by Clem Onojeghuo on Unsplash


The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.


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.

Operational Due Diligence Like You’ve Never Seen Before | Evan Finkel | Superclusters | S3E4

Evan currently serves as Head of Venture Capital Investments and Research for Integra Global Advisors, a multi-family office. Prior to Integra, Evan served as Senior Manager of Data Science for Anheuser-Busch InBev where he oversaw data science and strategy for the US marketing organization. Prior to Anheuser-Busch, Evan spent two years as a Management Consultant at Marketing Management Analytics and held a technical role at Amazon. Evan earned an MS in Computer Science with a concentration in machine learning from Georgia Tech and studied computational and applied mathematics at the City University of New York and finance and psychology at the University of Miami.

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

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

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[03:27] What are the mechanics of a great cold email?
[07:54] Evan’s background in sports marketing
[10:54] The kinds of data to ignore as an LP
[13:01] Portability and replicability of track record
[19:57] How much thesis drift is too much?
[22:37] What happens when a partner isn’t pulling their weight?
[29:35] Why does Evan have two bachelor degrees?
[34:38] Why study quantum mechanics in applied math?
[38:25] Evan’s journey to Integra
[45:21] Buy vs Build at a fund-of-funds
[47:40] Questions to ask when choosing which vendor to work with
[51:24] How Evan thinks about operational diligence
[58:30] Setting up an information policy in your firm
[1:01:39] Valuation policy at a hedge fund vs VC fund
[1:11:12] Why doesn’t Integra have strict mandates for geographies to invest in?
[1:21:20] The fallacy with LPs overweighing DPI in 2020-2021
[1:27:15] Evan’s greatest life lesson
[1:28:14] Evan’s favorite kosher restaurants in NYC
[1:32:07] “Post-credit scene”
[1:34:24] Thank you to Alchemist Accelerator for sponsoring!
[1:35:25] If you liked this episode, it would mean a lot if you left a like and shared this episode with one friend!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“It’s important to be data-informed, not data-driven.” – Evan Finkel

“Not only does [an investment] have to be the best in that geography, it actually has to be better than the incremental dollar we could put in any other geography.” – Evan Finkel

“The way we think about VC is both on an absolute and a relative basis. On an absolute basis, we have to be able to underwrite a manager to 3X net or better, or ideally 4X net or better. Because otherwise the lockup doesn’t make sense. It doesn’t make sense to lock up your money for 10, 12, or 15 years with pretty limited distributions. In order to be able to consider a VC fund for our portfolio, we have to be able to underwrite it to at least 3X, but ideally 4X or better.

“But then there’s also a relative component. We’re not looking for the best relative managers. Understanding whether this is a really good year or weak year… You might be the best manager of a given vintage, but in absolute terms, you actually might not be quite as impressive. […] It helps us contextualize the performance of a given manager.” – Evan Finkel

“DPI generated in a chaotic environment is sort of similar to TVPI generated in a chaotic environment. It’s great it happened, but let’s contextualize it properly and don’t overweight DPI when you’re evaluating managers.” – Evan Finkel

“In venture, we don’t look at IRR at all because manipulating IRR is far too easy with the timing of capital calls, credit lines, and various other levers that can be pulled by the GP.” – Evan Finkel


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

#unfiltered #90 If A Song Took a Lifetime to Play

music, song

Just the other day, I was listening to one of 99% Invisible’s episodes, interestingly titled as “As Slow As Possible,” named after the organization ASLSP, which stands for the same. My knee-jerk reaction was that the abbreviation and the first letters of each word just didn’t match up. Luckily, Roman Mars and Gabe Bullard explained. Although it still left something more to be desired.

“The title is also a reference to a line in James Joyce’s novel Finnegans Wake. The line is: ‘Soft morning, city! Lsp!’ Where lisp is just spelled L S P.”

Nevertheless, the episode itself circles around the concept of taking one song and using the entire lifespan of a pipe organ (639 years) to play that song just once. That even a single note would take two years to play. A fascinating concept! And which led me down a rabbit hole of thought experiments.

What if we took our favorite song and extrapolated that to the human lifespan? Say 90 years. What note would we be on today? Have we gotten to the chorus yet?

So for the sake of this thought experiment, for a brief second, let’s walk down the lane of music theory. Take the average pop song. The average pop song plays for about three minutes. And many at 120 beats per minute. Apparently, 120 bpm is also the golden number you want to get to if you’re working a crowd as a DJ. You never start at that speed, but you work your way up throughout the night. And if you can get people’s heart rate matching the beats per minute, you’ve hit resonance. But I digress.

So, taking round numbers, the average pop song has a total of 360 beats. Most songs are in 4/4 time. In other words, four beats per bar. An average pop song takes about 2-4 bars for the intro. 16 bars for a verse. Possibly, another 4 bars as the pre-chorus. And the first chorus doesn’t really start till bar 25. And usually lasts another 4-8 bars.

Now, if we were to extrapolate a song to the average human lifespan. 90 years. 360 beats across 90 years. Assuming it takes 24 bars to get to the chorus, the chorus doesn’t start until we’re 24 years old. And the full chorus doesn’t end until we’re 32 years old. With each note lasting a full three months. And the second chorus starts around age 48.

Then again, I remember reading somewhere that most pop songs are played in multiples of four or eight. And that most of these songs only have 80 bars. If that’s the case, the first chorus doesn’t kick in till we’re just past 28 years old and ends around 36 years old.

In either case, the first chorus happens around the time when most people would define as their prime. Young enough to take risks; old enough to be dangerous. The second chorus seems to fit as the second wind people have in their careers. Hell, HBR found, the median age of a startup founder when they start is 45. And with that reference point, they’ll be 47 or 48 when they become venture-backed.

Obviously, this is just me playing around with numbers. Correlation does not mean causation, of course. But nevertheless, the parallels… curious and uncanny.

P.S. Jaclyn Hester and my episode together on Superclusters got me thinking about a lot how much music applies to our lives and how we live and think.

Cover Photo at the top by Marius Masalar on Unsplash


#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘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.

VC Fund Secondaries Unlocked | Dave McClure | Superclusters | S3E2

dave mcclure

Dave McClure has been a Silicon Valley entrepreneur and investor for over 25 years. He has invested in hundreds of startups around the world, including 10+ IPOs and 40+ unicorns (Credit Karma, Twilio, SendGrid, Lyft, The RealReal, Talkdesk, Grab, Intercom, Canva, Udemy, Lucid, GitLab, Reddit, Stripe, Bukalapak).

Prior to launching PVC in 2019, he was the founding partner of 500 Startups, a global VC firm with $1B AUM that has invested in over 2,500 companies and 5,000 founders across 75 countries. Dave created 20 VC funds under the 500 brand and invested in 20 other VC funds around the world.

Dave began his investing career at Founders Fund where he made seed-stage investments in 40 companies, resulting in 4 unicorns and 3 IPOs. He led the Credit Karma seed round in 2009 (acq INTU, over 400X return). His $3M portfolio returned more than $200M (~65X) in under 10 years.

Before he became an investor, Dave was Director of Marketing at PayPal from 2001-2004. He was also the founder/CEO of Aslan Computing, acquired by Servinet in 1998. Dave graduated from the Johns Hopkins University (BS, Engineering / Applied Mathematics).

You can find Dave on his socials here:
Twitter: https://x.com/davemcclure
LinkedIn: https://www.linkedin.com/in/davemcclure/

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

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[03:37] How did Narnia inspire the start of Dave’s entrepreneurship?
[08:32] On the brink of bankruptcy
[11:42] The lesson Dave took away from his first acquisition
[13:19] What did Dave do that no one else did as a marketing director?
[16:06] What do most people fail to appreciate about secondaries?
[22:31] The 3 bucket method for secondaries
[28:46] How much do fund returners matter for secondaries?
[33:01] When do LPs typically think about selling fund secondaries?
[42:04] What are two questions that Dave asks to see if a portfolio is good for a secondary?
[46:10] Why is it complicated if a GP wants to buy an LP’s stake?
[55:03] When do most funds return 1X? 2-3X?
[57:13] Underwriting VC vs PE secondaries
[1:01:49] How do institutional LPs react to VC secondaries?
[1:07:01] The founding story of Practical VC
[1:15:36] Closing Josh Kopelman in Fund I
[1:18:47] How often does the PayPal Mafia get together?
[1:23:49] What’s the most expensive lessons Dave learned over the years?
[1:27:38] Thank you to Alchemist Accelerator for sponsoring!
[1:28:29] If you enjoyed the episode, would deeply appreciate you sharing with one other friend!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Anything worth doing is worth fucking up the first time. [But] hopefully you don’t keep fucking it up.” – Dave McClure

“Anything worth doing is worth doing badly.” – G. K. Chesterton

“There’s a huge discount for illiquidity, and there’s a huge discount for a lack of buyers.” – Dave McClure

“Secondaries is a dish best served cold.” – Dave McClure


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How Long is the VC Asset Class?

bridge, long

Axios’ Dan Primack recently wrote a great update on the shifting tides of institutional LPs allocating to venture. Smaller LPs often need liquidity, given limited capital inflows. And unfortunately, cannot afford to play the long game. Those with access to additional sources of capital, as well as aren’t constrained by mandatory capital outflows, tend to have deeper desires to continue allocating to venture.

Source: Dan Primack, Axios

In conversations with a number of LPs who write $3-10M checks, many have learned first-hand venture’s J-curve. Something these emerging LPs have underestimated in the last few years. As such, a number of foreign LPs are holding back. Moreover, there are looming concerns of currency risk. For instance, US-based LPs who have historically invested in funds domiciled outside of the US, are now accounting for currency depreciation. Ranging from 20-30%. Which means, what normally would have been a 4X net fund based in, say, Japan, is now underwritten as a 3X net. And a 10X would be an 8X.

Early liquidity is nice. But any DPI in the first few years is almost never meaningful and often gets recycled back into the fund to make new investments.

With VC being underwritten to 15-year time horizons, as a GP, you need LPs who can afford that time horizon. Yes, most funds have 10-year fund terms, with the two-year extension. But if the 2008-2012 vintages have taught us anything, it’s that GPs will ask for extensions beyond that. Simply since the best companies stay private longer. Airbnb was private for 12 years. Klaviyo, 11 years. Reddit, 19 years.

Of course, some of these companies are outliers. But the average tech company still stays private for 9-10 years. Assuming venture’s three-year deployment period, the last (hopefully great) investment out of a fund may take till Year 13 to finally achieve a large exit, not including the lock-up period too. That’s not accounting for a growing number of funds pitching four to five-year deployment periods. Excluding emerging market funds, where emerging market companies go public faster.

Moreover, companies need double the revenue they needed back in 2018 to go public. Shoutout to Tomasz Tunguz for the graphic.

Source: Tomasz Tunguz

To make things even more spicy, an interesting trend right now is where we see VC firms moving into PE, and PE moving into VC. At the same time, you have some large institutions who are now investing across multiple asset classes, including public markets. Consequentially, an interesting discussion commences. Should private investors hold public assets?

I was fortunate to be in an LP discussion group recently where we debated that exact question. The general consensus was no. VCs are paid to be private market investors, not public markets. Where their expertise does not lend itself well to watching market movements closely. The only exceptions are crossover funds who build out specific public markets teams. And so when an LP invests, they know exactly what they’re getting themselves into. The expectation is to return the capital back to the LPs right after the lock-up period.

But if the narrative ever changes, prepare for an even longer haul. Good thing, most LPs also agree that evergreen funds don’t make sense for venture either. But that’s a discussion for another day.

Photo by Sven Huls on Unsplash


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