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


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


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.

Bringing the Endowment Approach to Emerging Managers | John Felix | Superclusters | S3E1

John Felix is the Head of Emerging Managers at Allocate where he leads manager diligence and product innovation within the emerging manager ecosystem. Prior to joining Allocate, John worked at Bowdoin College’s Office of Investments, helping to invest the $2.8 billion endowment across all asset classes, focusing on venture capital. Prior to Bowdoin, John worked at Edgehill Endowment Partners, a $2 billion boutique OCIO. At Edgehill, John was responsible for building out the firm’s venture capital portfolio, sourcing and leading all venture fund commitments. John started his career at Washington University’s Investment Management Company as a member of the small investment team responsible for managing the university’s now $15 billion endowment. John graduated from Washington University in St. Louis with a BSBA in Finance and Entrepreneurship.

You can find John on his socials here:
LinkedIn: https://www.linkedin.com/in/johnfelix12/
Twitter: https://x.com/johnfelix123

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
[02:35] The band that started it all
[08:43] How did a band of 3 become a band of 5?
[10:39] What bands served as inspiration for John?
[13:37] Lessons on building teams and trust
[19:48] The mischance that led John into the endowment world
[22:34] What John learned under 3 different CIOs
[26:20] What does concentration mean for Washington University’s endowment?
[33:53] Portfolio construction perspectives at an endowment
[36:26] The flaws of GP commits
[41:25] How has John’s approach to emerging managers changed over the years?
[44:17] What is key person risk?
[47:06] One of the biggest challenges emerging managers face
[50:45] Balancing over- and under-diligencing an emerging manager
[56:28] What are traits that GPs think are unique but actually aren’t?
[1:03:36] What makes a great cold email?
[1:08:40] As a sports fan, do the highs or lows hit harder?
[1:11:53] Thank you to Alchemist Accelerator for sponsoring!
[1:12:54] Let me know if you enjoyed this episode with a like, comment or share!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Being too dogmatic about things or having too black or white views will prohibit a lot of LPs from making really, really good investments.” – John Felix

“The biggest leverage on time you can get is identifying which questions are the need-to-haves versus nice-to-haves and knowing when enough work is enough.” – John Felix


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 #88 Koi No Yokan

love, heart

In a late night conversation with my high school friend last week, I picked up a fascinating Japanese phrase from her. Koi no yokan.

The best translation of it that I found was ‘the premonition of love.’ It serves as the antithesis to the notion of love at first sight. It’s love that takes time to grow on you. Slow, but steady. A seemingly acquired, yet inevitable sense of fate. It’s a feeling that begins when you meet someone you’ll eventually fall in love with.

It’s a remarkable concept with no direct English parallel. It sits in rarified air between words like hiraeth, hyggelig, and yūgen. All of which have inextricable meaning behind a seemingly simplistic string of letters. While I’ll leave the afore-mentioned three to your own rabbit holes, as you might imagine, I’ve been having quite a field trip across the linguistic landscape.

Koi no yokan.

It’s a concept that’s often applied to the enamor between humans. This may just be me being a sacrilegious foreigner, but I find the same linguistic beauty with passions.

In many ways, my love for the emerging GP and LP world was the same. If you told me back in college, that I’d want to spend a few decades of my life obsessed over demystifying the space, I’d have called your bluff. Might have even called you bonkers.

And while I’d been hovering like a satellite around the space for a while, it wasn’t till I started writing The Non-Obvious Emerging LP Playbook that I realized there was an inkling of a yearning there. Answers only led to more questions. Each insight I learned was always paired with another punctuated with a question mark. And it honestly was a really fun exercise. I didn’t write that blogpost for anyone else. Just myself. Like a public diary that encapsulated my intellectual expedition in the LP world. Even before I published it, even before any other feedback I got for it, it felt special. All catalyzed by an opportunity to back a first-time fund manager I’d been honored to see grow as the last check in.

At that point, I still had neither committed to the idea of really being a capital allocator nor to the promise of more of such content.

And when that blogpost finally saw daylight, and a number of readers responded in kind, a tenured investor asked if I was going to write a book. It seemed only fitting that a non-fiction 200-page book be the successor to the 12,500 word blogpost. So pen met paper.

I revisited old and forged new relationships off the momentum of the blogpost. And around 80 pages into the manuscript, I ran out of things to write. I didn’t know how to continue. It felt both lacking and comprehensive at the same time. I could add in more examples. Case studies. Or just superfluous language. The equivalent of turning “my dad” into “my wife’s father-in-law.” The latter of which I swore to myself I wouldn’t do.

So I stopped.

Put it aside. And went on with the rest of my life.

But time and time again, I’d find myself staring at the ceiling at night, journaling, or writing on my whiteboard in the shower about the afore-mentioned topics. It became borderline annoying that my mind kept circling back to it and I was doing nothing about it.

So frick that. As I once learned from Max Nussenbaum, who I got to work with sooner after, the fastest way to test out if there’s a market for your ideas AND if one’s interests are sustained across longer periods of time is to just write about it. And I did. Here, here, here, and more.

At one point, my buddy Erik asked if I was going to start a podcast. At first, I dismissed the idea. Didn’t think I had the skillset or the personality for one. But man, I lost even more sleep in the ensuing weeks after he seeded the idea in my head. And so I started a podcast. (Which holy hell, I can’t wait to show you Season 3 on July 1st)

I realized much later, probably a year after I stopped writing the book, that the reason I couldn’t write anymore, despite asking so many really smart LPs for help, wasn’t that there was nothing more to share, there was still a lot… Hell, even each family office had a strategy so unlike the next. And as the saying goes, if you know one family office, you really only know one family office. So no, it wasn’t because there was nothing else to write. In one world, I could have just written an encyclopedia of strategies. It was that there was so much that had yet to be written, ever, about allocating into emerging managers.

Venture as an asset class was not the Wild West, still an alternative and still risky, but there have been predecessors who’ve productized the practice. But allocating to Fund I’s and II’s without proof of a track record was a horizon most had yet to cross.

Hell, I wrote a LinkedIn post just yesterday on how I think about evaluating Fund I track records without relying on TVPI, DPI, and IRR. And why I think more funds of funds should exist.

An excerpt on my LinkedIn post

Simply put and in summary, there’s a complexity premium on not just venture capital, but specifically on evaluating Fund Is and IIs. And I don’t mean the big firm spinouts who have a portable track record. I mean the real folks who are truly starting to build a firm (not just a fund) for the first time.

I don’t have all the answers. Sure, as hell, I hope to have more in the near future. But I’m ridiculously excited to find answers (and more nuanced questions) — putting science to art — as an emerging LP.

If you couldn’t tell yet… I think I’m in love.

And if you’re interested, I’d love to have you join me on this ride.

Photo by Mayur Gala 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.

The Power Law of Questions

question, mark

Recently I’ve been hearing a lot of power law this, power law that. And you guessed right, that’s VC and LP talk. Definitely not founder vocabulary. Simply, that 20% of inputs lead to 80% of outputs. For instance, 20% of investments yield 80% of the returns.

Along a similar vein… what about questions? What 20% of questions lead to 80% of answers you need to make a decision? Or help you get 80% of the way to conviction in a deal?

‘Cause really, every question after those delivers only marginal and diminishing returns. And too much so, then you end up just wasting the founder’s or GP’s time. As the late Don Valentine once said, “[VC] is all about figuring out which questions are the right questions to ask, and since we don’t have a clue what the right answer is, we’re very interested in the process by which the entrepreneur get to the conclusion that he offers.”

While I can’t speak for everyone, here are the questions that help me get to 80% conviction. For emerging GPs.

I’m going to exclude “What is your fund strategy?” Because you should have either asked this at the beginning or found out before the meeting. This question informs if you should even take the meeting in the first place. Is it a fit for what you’re looking for or not? There, as one would expect, you’d be looking into fund size, vertical, portfolio size, and stage largely. Simple, but necessary. At least to not waste anyone’s time from the get go.

Discipline. In the first 4 years of a fund, you’re evaluated on nothing else except for the discipline and the prepared mind that you have going in. All the small and early DPI and TVPI mean close to nothing. And it’s far too early for a GP to fall into their respective quartile. In other words, Fund I is selling that promise. The prepared mind. Fund II is selling Fund I’s strategy and discipline. Fund III, you’re selling the returns on Fund I.

Vision. Is this GP thinking about institutionalizing a firm versus just a fund? How are they thinking about creating processes and repeatability into their model? How do they think about succession and talent? And sometimes I go a few steps further. What does Fund V look like? And what does the steady state of your fund strategy look like?

This is going to help with reference calls and for you to fact check if an investor actually brings that kind of value to their portfolio companies. So, in effect, the question to portfolio companies would be: How has X investor helped you in your journey?

On the flip side, even during those reference calls, I like asking: Would you take their check if they doubled their ownership? And for me to figure out how high can they take their ownership in a company before the check is no longer worth it. There are some investors who are phenomenal $250K pre-seed/seed checks for 2.5-5% ownership (other times less), but not worth their value for $2-3M checks for the same stages. To me, that’s indicative of where the market thinks GP-market fit is at.

I also love the line of questioning that Eric Bahn once taught me. “How would you rate this GP on a scale of 1 to 10?” Oftentimes, founders will give them a rating of 6, 7, 8, or if you’re lucky 9. And the follow up question then becomes, “What would get this investor to a 10?” And that’s where meaty parts are.

Of course, it’s important to do this exercise a few times, especially with the top performers in their portfolio to truly have a decent benchmark. And the ones that didn’t do so well. After all, our brand is made by our winners. And our reputation is made by those that didn’t.

In the trifecta of sourcing, picking, and winning, this is how GPs win deals.

This is really prescient in a partnership. Same as a co-foundership. If someone says, we never disagree, I’m running fast in the other direction. Everyone disagrees and has conflicts. Even twins and best friends do. If you don’t, you either have been sweeping things under the rug or one (or both or all) of you doesn’t care enough to give a shit. Because if you give a damn, you’re gonna have opinions. And not all humans have the same opinions. If everyone does, realistically, we only need one of you.

Hell, Jaclyn Freeman Hester even goes a step further and asks, How would you fire your partner?

Jaclyn on firing partners and team risk

Personally I think that last question yields interesting results and thought exercises, but lower on my totem pole (or higher if you want to be culturally accurate) of questions I need answers to in the initial meetings.

This is always a question I get to, but especially valuable, when I ask it to spinouts. Building a repeatable and scalable sourcing pipeline is one of the cruxes of being a great fund manager. But in the age when a lot of LPs are shifting their focus to spinouts from top-tier funds, it’s an important reminder that (a) not all spinouts are created equal, and (b) most often, I find spinouts who rely largely on their existing “brand” and “network” without being able to quantify the pillars of it and how it’s repeatable.

For (a), a GP spinning out is evaluated differently than a partner or a junior investment member. A GP is one who manages the LP relationships, and knows intimately the value of what goes in an LPA, on top of her/his investing prowess. And the further you go down the food chain, the less visibility one gets of the end to end process. In many ways, the associates and analysts spinning out need the most help, but are also most willing to hustle.

Which brings me to (b). Most spinouts rely on the infrastructure and brand of their previous firm, and once they’ve left, they lose that brand within a year’s time. Meaning if they don’t find a way or have an existing way to continue to build deal flow, oftentimes, they’ll be left with the leftovers on the venture table. This question, for me, gives me a sense of whether an investor is a lean-in investor or a lean-back investor. The devil’s in the details.

This is a test to see how much self-awareness a founder/GP has. The most dangerous answer is saying “There are no reasons not to invest.” There are always reasons not to. The question is, are you aware of them? And can you prioritize which risks to de-risk first?

In many ways, I think pitching a Fund I as illustrating the minimum viable assumption you need to get to the minimum viable product. And Fund II is getting to the minimum lovable strategy (by founders and other investors in the ecosystem). And with anything that is minimally viable, there are a bunch of holes in it.

Another way to say the above is also, “If halfway through the fund we realize the fund isn’t working, what is the most likely reason why?”


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 Limited Partner Game Show | Beezer Clarkson & Chris Douvos | Superclusters | S2 Post Season Episode

Beezer Clarkson leads Sapphire Partners‘ investments in venture funds domestically and internationally. Beezer began her career in financial services over 20 years ago at Morgan Stanley in its global infrastructure group. Since, she has held various direct and indirect venture investment roles, as well as operational roles in software business development at Hewlett Packard. Prior to joining Sapphire in 2012, Beezer managed the day-to-day operations of the Draper Fisher Jurvetson Global Network, which then had $7 billion under management across 16 venture funds worldwide.

In 2016, Beezer led the launch of OpenLP, an effort to help foster greater understanding in the entrepreneur-to-LP tech ecosystem. Beezer earned a bachelor’s in government from Wesleyan University, where she served on the board of trustees and currently serves as an advisor to the Wesleyan Endowment Investment Committee. She is currently serving on the board of the NVCA and holds an MBA from Harvard Business School.

Chris Douvos founded Ahoy Capital in 2018 to build an intentionally right-sized firm that could pursue investment excellence while prizing a spirit of partnership with all of its constituencies. A pioneering investor in the micro-VC movement, Chris has been a fixture in venture capital for nearly two decades. Prior to Ahoy Capital, Chris spearheaded investment efforts at Venture Investment Associates, and The Investment Fund for Foundations. He learned the craft of illiquid investing at Princeton University’s endowment. Chris earned his B.A. with Distinction from Yale College in 1994 and an M.B.A. from Yale School of Management in 2001.

You can find Chris and Beezer on their socials here.

Connect with Beezer here:
Twitter: https://twitter.com/beezer232
LinkedIn: https://www.linkedin.com/in/elizabethclarkson/

Connect with Chris here:
Twitter: https://twitter.com/cdouvos
LinkedIn: https://www.linkedin.com/in/chrisdouvos/

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
[03:07] Beezer’s childhood dream
[04:29] How Chris was let go from his $4.15 job at Yale
[08:09] Concentrated vs diversified portfolios
[09:30] First fund that Beezer and Chris invested
[11:42] Funds that CD and Beezer passed on and regret
[16:07] Favorite term in the LPA? Or not?
[19:18] What piece of advice did a GP in their portfolio share with them?
[23:15] What’s something that Beezer/CD said to a GP that they regret saying?
[28:06] What’s the most interesting fund model they’ve seen to date?
[33:20] What fund invested in 2020-2021 inflated valuations that they’ve reupped on?
[40:18] Events that they went to once but never again
[44:24] Life lessons from CD & Beezer
[54:02] The founding story of Open LP
[55:02] Thank you to Alchemist Accelerator for sponsoring!
[57:58] If you learned something new in this episode, it would mean a lot if you could drop a like, comment or share it with your friends!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“If you’re overly concentrated, you better be damn good at your job ‘cause you just raised the bar too high.” – Beezer Clarkson

“Conviction drives concentration, and that you should be so concentrated as to be uncomfortable because otherwise you’re de-worsified, not diversified.” – Chris Douvos

“[David Marquardt] said, ‘You know what? You’re a well-trained institutional investor. And your decision was precisely right and exactly wrong.’ And sometimes that happens. In this business, sometimes good decisions have bad outcomes and bad decisions have good outcomes.” – Chris Douvos

“Sometimes I treat GPs like I treat my teenage children which is: Every word out of a teenager’s mouth is probably a lie designed to make them look better or to hide some malfeasance.” – Chris Douvos

“May we be blessed by a weak benchmark.” – David Swensen

“Miller Motorcars doesn’t accept relative performance for least payments on your Lamborghini.” – Chris Douvos (citing hedge fund managers)

“At the end of the day, the return on an asset is a function of the price you paid for it and the capital it consumes.” – Chris Douvos


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

Telltale Signs of When Risk is High

jenga, risky

At the end of last week, an LP told me something quite provocative. That right now in 2024, we’re in a low-risk environment.

And in all fairness, I thought he was completely bonkers. Fear is high. Investments have slowed their pace, especially in the private markets. Markets have really yet to recover. Some believe we’ve hit the bottom and will bounce around the bottom a few times. Others think we’ve yet to see the worst of it. Hell, just yesterday, Eric Bahn tweeted the below:

Wars are raging across the world. Currency is fluctuating on a global scale. Hell, even for the average person, prices are going up at a rate unfamiliar to most people’s memory.

But his next line really made me pause. “You’re right. There’s geopolitical risk, currency risk, market risk, and valuation/pricing risk. And we can identify every single one of them. In fact, the actual risk of investing today is really low, but the perceived risk is really high. Risk is highest when you can’t tell what the risk is. That was 2020 and 2021, when you couldn’t put a finger on what kinds of risk were out there.”

And that really stuck with me. To underscore again, risk is highest when you can’t tell what the risk is.

And so paved way for this blogpost. Albeit, that last line was the punchline.

He later told me that the concept wasn’t original, but that its origin traces its way back to Ken Moelis. Regardless of the attribution, it’s worth doing a double take on.

There’s that famous Peter Drucker line, “You can’t manage what you don’t measure.” And in many ways, it is just as true for risk as it is for tasks and KPIs and OKRs.

The family office for a well-known luxury brand once told me that they like to pay the complexity premium on esoteric alternatives. To them, venture is one of those esoteric alternatives. In addition, they’re also happy to overpay during bull markets. Access to a volatile and nascent asset class, to them, deserves a premium.

But taking a step back, there may be more wisdom to it than I initially thought. In bear markets, when the risk is real and discrete, there is no complexity premium to pay. After all, you can begin to manage what you do measure. On the flip side, in a bull market, where no one really knows who will win or what the macro risks are, a premium can be and often is paid as a bet on a company’s future and insurance against a margin of error that is hard to define.

Of course, one can say that the premium is often hype-driven instead of risk-driven. But really, hype is just long-term risk donned with a new set of clothes. A short-term luxury with a buy-now-pay-later tag that comes in quarterly installments of belt-tightening and regret.

While I personally have always believed that as an investor it’s better to be disciplined and to “dollar cost average” across vintages vis a vis time diversification, there are several great investors who believe price is a trap. At the top of my head, Peter Fenton and Keith Rabois. The latter shared his thoughts earlier this year on why. At least for seed and Series A. That in summary, there is no limit on how much you pay for a great company at the seed and Series A (likely the pre-seed as well) that won’t return you multiple-fold back. And that debates on price really are leading indicators on conviction or lack thereof.

The last part of which I agree to an extent.

All that to say, I think a useful exercise to go through whenever making a major (investment) decision is to take out a notepad and write down all the risks you can think of. If you can think of it, you can probably find a way to hedge against it. On the flip side, if you’re about to make a decision and you can’t think of any risks, that’s probably the biggest risk you’ll take.

As my mom told me since I was a kid, “There’s no such thing as a free lunch.”

But if you do come up with a good list, and the world around you is still scared, and you think there might be something special in the opportunity in front of you, sometimes it pays to be bullish when others are bearish.

Photo by Naveen Kumar 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.

Qualitative Signals to Look for in Emerging GPs | Jaclyn Freeman Hester | Superclusters | S2E9

Jaclyn Freeman Hester is a Partner at Foundry. She joined in 2016 with a passion for supporting the next generation of entrepreneurs and investors. Jaclyn leads direct investments in early-stage companies, often collaborating with Foundry’s partner funds. She loves working closely with founders to solve hard problems and think about the human elements of business. She invests across B2B and consumer companies that exhibit strong end-user empathy and use technology to empower individuals, unlock potential, and improve experiences.

Jaclyn helped launch Foundry’s partner fund strategy, building the portfolio to nearly 50 managers. Bringing her unique GP + LP perspective, Jaclyn has become a go-to sounding board for emerging VCs.

Jaclyn first fell in love with entrepreneurship while earning her JD/MBA at CU Boulder (Go Buffs!). There, she served as Executive Director of Startup Colorado, where she got to know Foundry and the incredible Boulder/Denver startup community the firm helped catalyze. In her brief stint as a practicing attorney, Jaclyn advised clients in M&A transactions and early-stage financings. She also witnessed the founder journey first-hand, working closely with her husband and his family as they built a B2B SaaS company, FareHarbor (acquired by BKNG).

Jaclyn loves the Boulder lifestyle, but her heart will always be on the East Coast, having grown up a New England “beach kid.” She is the proud mother of three humans and three dogs and is a blue-groomer-on-a-sunny-day skier and 9-hole golfer. In her glimpses of free time, you can find Jaclyn enjoying live music, especially at Red Rocks and in Telluride, two of the most magical places in the world.

You can find Jaclyn on her socials here:
Twitter: https://twitter.com/jfreester
LinkedIn: https://www.linkedin.com/in/jaclyn-freeman-hester-70621126/

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
[03:24] The significance of Kara Nortman in Jaclyn’s life
[13:59] Lesson on recognizing effort from Dan Scheinman, Board Member at Zoom
[18:27] The question to disarm GPs learned from Jonathon Triest at Ludlow Ventures
[23:37] The differences between being a board member and an LPAC member
[32:04] Turnover within institutional LPs
[33:58] The telltale signs of team risk in a partnership
[41:25] How to answer “How do you fire your partner?”
[44:05] Foundry’s portfolio construction
[53:22] What makes Lan Xuezhao at Basis Set so special?
[59:59] What does Shark Tank get right about venture?
[1:03:37] Jaclyn’s Gorilla Glue story
[1:05:51] What keeps Jaclyn humble today?
[1:12:11] What will Jaclyn do after Foundry’s last fund?
[1:16:28] Jaclyn’s closing thought for LPs
[1:18:10] Thank you to Alchemist Accelerator for sponsoring!
[1:20:46] If you enjoyed this episode, a like, a comment, a share will go a long way!

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“By the time track record is established, it’s almost too late.” – Jaclyn Freeman Hester


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For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
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An LP’s Guide to the European VC Ecosystem | Ertan Can | Superclusters | S2E8

Ertan Can is the Founder of Multiple Capital, a fund of funds focused on investing in micro VC funds in Europe and has been a limited partner in top funds you’ve heard of including Entrepreneur First and Angular Ventures, just to name a few. He’s done his tour of duty in the asset management world at JP Morgan to covering investor relations topics at Thomson Reuters to investing in startups at a family office. Ertan is also a founding member of 2hearts, a community dedicated to building tomorrow’s tech society with cultural diversity.

He is also a proud MBA graduate from the ESCP Business School and a long time student of finance and law catalyzed by his time at Frankfurt and London.

You can find Ertan on his socials here:
Twitter: https://twitter.com/rtancan
LinkedIn: https://www.linkedin.com/in/ertancan/

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
[02:21] Ertan’s childhood
[05:36] Why Luxembourg?
[15:03] Which countries do European GPs set up their funds?
[19:46] How did Ertan switch the family office strategy from direct to fund investing?
[24:42] How has Ertan’s underwriting process evolved over time?
[28:04] Do similar pitch deck formats make it easier or harder to make investment decisions?
[30:34] Referrals and warm intros ranked by source
[36:10] Geographies that Multiple Capital invests in
[37:44] Red flags for Multiple Capital
[43:48] How do solo GPs build sounding boards to check their blindside?
[49:04] The (un)predictability of outlier investments
[1:00:41] How does Ertan think about bringing on Venture Partners in a fund of funds?
[1:08:25] The decision-making framework behind an “angel” LP investment and a FoF check
[1:12:01] Where Ertan shares his unfiltered thoughts
[1:20:14] Ertan’s experience around giving GPs feedback
[1:27:05] Cockroaches and superheroes
[1:34:08] Thank you to Alchemist Accelerator for sponsoring!
[1:36:44] If you enjoyed this episode, it would mean the world to us if you gave us a like, comment, or share!

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“Our work is to increase the probability of having some of the outliers as early as possible in as small as possible funds because like a fund, that will lead to a power law in our portfolio.” – Ertan Can


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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How to Get Six Top Quartile Fund of Funds in a Row | Aram Verdiyan | Superclusters | S2E7

aram verdiyan, accolade partners

Aram Verdiyan is a Partner at Accolade. Previously, he worked on the investment team at Andreessen Horowitz. Before that, Aram worked in BD, sales and marketing at Aviatrix, a cloud native enterprise software company. Aram worked at Accolade from 2012 to 2015 as a Senior Investment Associate and at Deloitte Consulting LLP. He holds an M.B.A from the Stanford Graduate School of Business (GSB) and a B.S. from the George Washington University.

You can find Aram on his socials here:
Twitter: https://twitter.com/aramverdi
LinkedIn: https://www.linkedin.com/in/aram-verdiyan-8099186/

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
[02:36] How did Pejman Nozad influence the way Aram thinks about people
[04:06] Aram’s ‘distance traveled’
[05:45] What did imposter syndrome look like in Aram’s life?
[06:36] How Aram cold emailed his way into Accolade Partners
[09:03] The first case study Aram did at Accolade
[10:10] When track record is NOT just TVPI, DPI, or IRR
[15:05] The case for concentrated fund of funds’ portfolio construction
[22:42] Telltale signs of “great” deal flow
[26:32] When does due diligence start for prospective funds for Accolade?
[27:50] Primary sources of data for Accolade
[29:00] The variables that impact fund of funds’ team size
[30:24] How many fund investments should each individual FoF partner have?
[35:13] The case for consistent check sizes
[36:20] The common mistake GPs make when it comes to LP concentration limits
[41:27] How Accolade started investing in blockchain funds
[44:52] Blockchain engineering talent as a function of bear markets
[47:15] Time horizons for blockchain funds
[50:38] Luck vs skill
[53:41] Aram’s early fundraising days at Accolade
[57:38] Thank you to Alchemist Accelerator for sponsoring!
[1:00:14] If you enjoyed the episode, drop us a like, comment or share!

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“[When] you’re generally looking at four to five hundred distinct companies, 10% of those companies generally drive most of the returns. You want to make sure that the company that drives the returns you are invested in with the manager where you size it appropriately relative to your overall fund of funds. So when we double click on our funds, the top 10 portfolio companies – not the funds, but portfolio companies, return sometimes multiples of our fund of funds.” – Aram Verdiyan

“We don’t have varying levels of conviction.” – Aram Verdiyan


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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