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.
[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!
“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
I’ve never met a founder or fund manager I deeply respected say, “Beggars can’t be choosers.” Or “It is what it is.”
While it wasn’t the first time I’ve heard of the phrase, I liked the way a fund-of-funds GP put it yesterday. “I invest in GPs who can run through walls.”
As an early-stage investor — be it in pre-seed/seed startups or in emerging managers — there is literally no metric, no number, no amount of traction that can truly convince us just by themselves to invest. If there are, you’re too late. The truth is it’s about people. And that failing to get conviction, most of the time is we haven’t find the right person yet to execute against the vision.
It’s about people who move fast.
It’s about people who learn fast.
It’s about people who wow you in ways you don’t expect.
It’s about people who are so smart and learn so quickly that outpace your ability to absorb said information.
It’s about people (at least in the early days) rarely, if ever, hedge.
It’s about people who make us question if our thesis really matters.
It’s about people who compel us to write an angel check for an off-thesis investment.
It’s about people who will succeed whether we back them or not.
It’s about people who are ambitious enough to take on the world, but humble enough to know they don’t know everything.
There’s this line I heard in a recent Tim Ferriss podcast with Martha Beck that I really like. “I don’t know where we’re going, but I know exactly how to get there.” If you have frequent flyer miles on this blog, you know one of my favorite heuristics is Mike Maples’ line. “90% of our exit profits have come from pivots.” The ideas we invest in don’t often look like the ideas that generate us there is literally no metric, no number, no amount of traction that can truly convince — pardon my French — shitloads of money.
In fact, “It is what it is” is a function of ambition. The greater one’s ambition, and the greater the recognition there is for the work it requires to get to that level, the less likely that statement and that mentality will come to fruition. Visionaries question the status quo and challenge it. And no matter what, they’ll figure out a way.
On the flip side, as James Stockdale once put it, “You must never confuse faith that you will prevail in the end – which you can never afford to lose – with the discipline to confront the most brutal facts of your current reality, whatever they may be.”
The discipline of reality
I’ve never seen a great founder or a great investor not be able to intimately explain how amazing their direct and indirect competition is. How they wouldn’t be here if not for others paving the road. In either career and personal growth. Or changing the customer mindset. Or who validated the market for them. Or who created the business model before they did.
After all, it’s extremely easy to share in one’s reality distortion field how everyone else sucks, and that you are the only one who’s doing things right. Failure to recognize what got your competition to where they are today and why their customers and fans love them is a failure to understand and truly appreciate the market you’re serving.
In closing
I spend a lot of time thinking about a Jim Collins’ line, “It is not that beauty is hard to find, it’s that it is easy to overlook.”
It really is. For smart people with degrees in finance and business with C-something-A’s attached to their title, it’s really easy to see what can go wrong. Hell, most companies are default dead when they pitch to us, early-stage investors. As Roelof Botha and Pat Grady put it, “it’s not about figuring out what’s wrong, it’s about figuring out what’s right.”
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.
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.
[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!
“[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
Two weeks ago, Ted Seides put out a great blogpost titled: The Investment Office Playbook – What Managers Don’t See. It’s the truth behind the veil of “It’s not you, it’s me” answer that LPs give. And that the best time for managers to be approaching CIOs at institutions happens to be:
1-2 years after they’re just sworn in (in other words, after they’ve figured out their strategy)
Up to 2-4 years after that period when they’re deploying against that strategy
And around years 11-13 where they’re now restructuring their portfolio after their previous portfolio has been optimized and reached maturity
Last week, Sequoia’s Jess Leeshared a fascinating product-market fit framework. Probably the best breakdown of solutions to problems mapping I’ve seen of late. It echoes much of what I’ve writtenbefore, but more eloquently put.
And the reason I bring this up is not to induce whiplash as you’re reading this blogpost. But that it relates back to when to raise from large LPs. As most of us know, there’s a strong correlation between fundraising as a founder and fundraising as a GP.
The first step is to have a product that large LPs can invest in. As a matter of fact, you need to have a specific product (aka fund strategy) for the LP you wish to court. For example, if a large LP’s minimum check size is $20M and their maximum ownership is 10%, and you’re a $50M fund, you don’t have what they’re looking for. That’s okay. You should never resize your fund purely on an LP’s check size and ownership.
The second is to understand their deployment timeline. In the case of large LPs, like endowments and pensions, that’s usually 2-4 years after a new CIO is sworn in. And years 11-13 when they’re rebalancing their portfolio. For other institutions, like some corporates, it’s actually in the bylaws that every three years, there’s a new Head of Investments. Hell, at Norges Bank Investment Management (NBIM) — the largest sovereign wealth fund, or at least one of the largest ones — a new CEO is sworn in every five years. So the clock is always ticking.
To the second point, for a large LP:
Years 1-2
When the new CIO is just sworn in, in many ways, that might be the best time to pitch a new paradigm. When the strategy has yet to fully shape up. Will you get many checks during that period? Likely not. Unless you’re a pre-existing trusted relationship of the CIO. But even if you do convince the CIO/team, they’re likely only allocating a very small percentage to that field, which for the most part, should work for you.
The goal of the value proposition, and subsequently the onboarding and tutorial, is to give people the activation energy needed to overcome the customer mindset. As such, it means one’s product can’t just be 10-20% better, but 10X better.
For instance, to get over the “yeah, right” and the “it is what it is” mindset, in the words of NFX’s Omri Drory, “the best way to manipulate energy, and get what you want, is to remove that ‘imagination barrier.'”
As such, the CIO must believe in the new paradigm. In all fairness, this takes more validation and big headlines for a tenured CIO to usually begin to believe these.
Years 2-4 (and 11-13)
They’re deploying against a top-down approach. And just as in years 11-13, they’re looking for the best in class solutions for each vertical. Meaning they’ll talk to hundreds of managers and look through thousands of pitches to pick just a few. Processes are long because they dig deep on these multi-fund relationships, but this is also an opportunity for them to increase the surface area for luck to stick.
While we all know past performance isn’t an indicator of future results, there is a reliance on metrics and the consistency of such metrics. For instance, if one were to take the top 2 investments in your portfolio and bottom 2 investments and throw them out, what does your remaining track record look like?
Or if some of your funds have yet to have meaningful distributions, graduation rates become rather important. Not just that on average, 30% of seed stage deals graduate to Series A. And 30% of Series A to B. But how many of your deals graduate past more than one subsequent round? For example, do more than 10% of your seed deals graduate to Series B? Although, to play my own devil’s advocate, vintages post-2019 have yet to really learn the true impact of loss ratios.
In closing
The truth is it’s hard to tell when the best time is. And oftentimes, it’s just a matter of luck. For one to have the right fund a specific LP is looking for at a time when liquidity is good.
But in many other ways, like Ted suggests in his blogpost, it’s the ability to think from the perspective of an LP that is invaluable and greatly appreciated as an LP.
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.
Jaap Vriesendorp is one of the managing partners of Marktlink Capital, an investment manager from the Netherlands investing over $1b into private equity and venture capital funds. Marktlink Capital’s LPs are almost exclusively Dutch (tech) entrepreneurs from companies such as Booking.com, Adyen and Hellofresh. At Marktlink Capital Jaap focusses on selecting venture and growth funds across Europe and the US. Before Marktlink Capital, he spent the majority of his time at McKinsey where he was one of the leaders of McKinsey’s practice for Venture Capital, Unicorns & Startups in Europe. Besides work, Jaap enjoys sports, mountains, technology, comic books, music and art.
He holds an MBA from INSEAD and is a guest lecturer at the Rotterdam School of Management (Erasmus University). He occasionally shares his views on private market investing on Medium.
[00:00] Intro [03:04] The significance of Mount Pinatubo in Jaap’s life [06:23] One Shell Jackets [08:45] The entrepreneurial gene in the Vriesendorp family that dates back to Jaap’s grandfather [14:32] The 1-year time constraint of starting Welt Ventures [17:43] What did the transition to becoming an investor look like for Jaap [20:28] The 3 traits that define a community [24:03] How often does Jaap host events? [25:30] How does Marktlink Capital have 1000 LPs? [27:15] What was Marktlink’s pitch to their LPs? [28:32] What is the typical individual LP’s allocation model to VC/PE? [29:41] Why is VC/PE uncorrelated to the public markets? [35:10] The 3 facts that define Welt Ventures’ portfolio construction model [38:28] Exit windows matter more than entry windows [42:15] Diversification in PE = Concentration in VC [47:42] 3 types of emerging GPs that deliver alpha [49:35] Which European fund has a really unique thesis? [51:44] Which school did Jaap apply to but not get in? [53:55] Thank you to Alchemist Accelerator for sponsoring! [56:31] If anything resonated with you in today’s episode, we’d be honored to earn a like, comment, or share!
“We set out to achieve three things with the community:
We wanted people to have fun with each other. And when entrepreneurs meet entrepreneurs, good stuff happens even if you don’t bring any content.
We wanted to bring the absolute best type of propositions. So in terms of sales, it means sales almost without being sales where you offer something that people really want.
Organized knowledge in a way that nobody does.” – Jaap Vriesendorp
“85% of returns flow to 5% of the funds, and that those 5% of the funds are very sticky. So we call that the ‘Champions League Effect.’” – Jaap Vriesendorp
“The truth of the matter, when we look at the data, is that entry points matter much less than the exit points. Because venture is about outliers and outliers are created through IPOs, the exit window matters a lot. And to create a big enough exit window to let every vintage that we create in the fund of funds world to be a good vintage, we invest [in] pre-seed and seed funds – that invest in companies that need to go to the stock market maybe in 7-8 years. Then Series A and Series B equal ‘early stage.’ And everything later than that, we call ‘growth.’” – Jaap Vriesendorp
I’ve always admired the way Mike Maples has thought about backcasting. In summary, he proposes that true innovators are visitors from the future. Or as he puts it: “Breakthrough builders are visitors from the future, telling us what’s coming.” Such that they “pull the present from the current reality to the future of their design.” In other words, start from the future, then work your way backwards to figure out what you need to do today to get there.
And I find it equally as empowering to do the same exercise as an emerging manager. Hell, for any aspiring institutional investor. Be it from an angel to a GP. Or an individual LP to a fund of funds.
Start from your ideal fund model. Your ideal LP base. Your ideal pitch deck. Then work backwards to figure out what you need to do today. For the purpose of this blogpost, I’ll focus on reference checks.
For everyone in the investing world, especially in the early-stage private markets, we all know that reference checks is a key component of making investment decisions. Yet too often, founders and emerging managers alike think about them retroactively. Post-mortem. Testimonials that are often not indicative of one’s strengths. And especially not indicative of how a GP won that investment, as well as how they can win such investments in the future.
An exercise I often recommend investors do is write your ideal reference you would like to get from a founder. Be as specific as you can. What would your portfolio founders say about you? How have you helped them in a way that no one else can? What do founders who you didn’t fund say about you?
Another way to think about it is if you were to own a word — something that would live rent free in people’s minds — what would you own? Hustle Fund owns “hilariously early.” Spacecadet Ventures owns “the marketing VC” and they live up to it. Cowboy’s Aileen Lee created the idea of “unicorns.” “Software is eating the world” is attributed to Marc Andreessen.
On the flip side of the token, what are testimonials that should never be written about you?
Hell, at this point, if you’re an aspiring institutional investor, and have yet to spell things out, create the whole deck. Fill in the numbers and the facts later, but for now, make up your ideal deck. When leading indicators become lagging, then update it and fill it in.
Then be that kind of investor for every founder you help. As Warren Buffett once said, “You should write your obituary and then try and figure out how to live up to it.”
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.
Aakar Vachhani is a Managing Partner and a member of Fairview’s investment committee. He is involved in research, due diligence, investment monitoring, and business development for Fairview’s venture capital and private equity partnership and direct co-investment portfolios.
Prior to joining Fairview, Aakar was with Cambridge Associates, a leading investment advisor to foundations, endowments and corporate and government entities. He was responsible for analyzing private equity and venture capital investments in support of the firm’s clients and consultants. In addition, he led research and data analytics projects on the firm’s private equity and venture capital database. Aakar also spent time with MK Capital, a multi-stage venture capital firm with a sector focus on software and cloud services.
Aakar Vachhani holds a B.S. in Economics-Finance from Bentley University and an MBA in Finance and Entrepreneurship & Innovation from the Kellogg School of Management. He is a member of the Board of Directors of San Francisco Achievers and the New Breath Foundation. On top of that, Aakar established and leads Fairview’s San Francisco office.
[00:00] Intro [04:29] Growing up in a household of 10 [09:36] Aakar’s leadership style when he was a child [12:12] Why Aakar turned down a job in insurance back at home [17:25] The third time Aakar applied to Cambridge Associates [21:56] How Fairview aligns incentives with each investment they make [26:15] How Fairview helps their GPs [28:58] How Fairview gives pitch feedback to GPs [32:54] Reasons Fairview passes on a GP [34:58] How does Aakar define what a “new manager” looks like? [37:55] How did Aakar build out Fairview’s SF Bay Area practice? [44:26] Fairview’s onboarding process for new hires [47:21] Why Fairview’s investment decisions need to be unanimous [52:17] The balancing act between a narrow thesis and a big market [56:09] Why Fairview invested in Eniac Ventures [57:56] What does a helpful LPAC member look like? [59:30] Typical questions GPs bring to their LPAC [1:01:13] How do the best GPs communicate strategy drift to their LPs? [1:03:01] Why LPs dislike strategy drift [1:06:28] What new technologies does Aakar think LPs should pay attention to? [1:08:30] Aakar’s core memories [1:11:45] Thank you to Alchemist Accelerator for sponsoring! [1:14:22] If you enjoyed the episode, it would mean a lot if you could like, comment, share, or subscribe!
Possibly the quiet thing out loud, one of the best parts about demo days is the excuse to catch up with old friends. Yes, we do go there to see deals, but realistically, many of us would have started the conversations with many of the demoing class before demo day. This is not only true for VCs at startup demo days, but equally so for LPs at emerging manager demo days.
Earlier this week, my friend invited me to go to his emerging manager demo day. I’ve always admired how intentional he’s been with picking, so it was a natural yes. The pitches came and gone. And as the networking part kicked off after, a few LP friends and I came together to catch up but also to compare notes. What did we think of Fund A? Fund D? Who was interesting? Who would we take a second conversation with? And why?
Naturally, we shared our respective decision-making frameworks. A lot of which overlapped. Others were more unique to each LP themselves. Simply because the motivations of LPs often differ from each other. Some do so for co-investment opportunities. Others invest in VC as an asset class. And there are also those that invest to pay it forward.
So while it’s not my place to share the words whispered to me in confidence, here are some general takeaways:
Unlike startup pitches, there is no consistency of pitch format among emerging managers.
Most GPs don’t seem to know what kinds of metrics/facts immediately stand out to an LP. One such GP buried an amazing angel track record TVPI as one line in his deck.
Humor sells.
Spinouts are only interesting if your track record is portable. In other words, if you were too junior on the team to have pounded the table for deals, you don’t count as a spinout in some LP’s minds.
Unscripted moments are memorable. At least ones that feel unscripted.
DPI earned within 5 years (as opposed to 5+ years) begs the question of where does it come from (i.e. secondaries, acquisition, etc. Former will lead to yellow flags.)
Track records that began post-2019 have an asterisk next to them.
That said, if it may be helpful to not only GPs, or other LPs out there, I’ll share my own calculus below.
I want to preface that the goal of the below “checklist” is for me to quickly decide which GPs I should follow up with, given limited information in the format of a 5-minute pitch. As such, this isn’t all-inclusive, but simply answers the question: Is this fund/manager interesting enough for me to spend another hour with them?
I will also say that this works best for me particularly for Funds I and II.
And one more thing, I’m still a WIP. In other words, this is the checklist that suits my current needs the best, but your mileage may vary.
The Demo Day checklist
At a high level, below are the five categories that are the most interesting to me.
Sourcing — Are they fishing in differentiated pools? Do they have proprietary access to deals? Where are they finding diamonds in the rough?
Picking — This can be interesting in two ways: (a) track record (which only starts to become interesting after 5+ years with 20+ deals), and/or (b) decision-making framework/algorithm.
Winning — Why do the best founders pick you? How much ownership can you get in these companies? Some examples here.
Likability — You’re either very likeable or contrarian. Anything else just isn’t memorable. And if not memorable for me, likely not memorable for founders. In many ways, I’m looking for ways you stay rent free in a founder’s mind when they know nothing else other than the fact that you invest in early stage companies. ‘Cause let’s be honest; most firm’s websites say just that and nothing more. Some might call this GP-founder fit. Others call it vibes.
Uniqueness — A bit amorphous here, but really, it’s just: Is there something I’ve never heard of before?
As a caveat, I only started including this “pillar” after I saw about 200 decks and pitches. Before that, I simply didn’t know what counted as unique and what didn’t.
And for each category, I give 4 different kinds of scores.
✔️
There’s something special here. Worth digging deeper. If I continue on to diligence, this is usually the first thing I reference check.
〰️
No strong opinion here and/or there’s no edge here.
❌
I use this extremely sparingly. This is a sign of a red flag. In fact, there are very few red flags that can even come out in a 5-minute pitch. So really, I only use an X when I feel the fund manager is sharing something dishonest.
Yes, that’s a blank space. Meaning the pitch itself failed to offer any reference point or evidence on this variable.
And for the five categories above, having a check mark in at least two of them is enough for me to say yes to another conversation. No single A+ trait standing in pure isolation. But only one X is enough for me to pass.
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 Teneriello has been a career-long investor in the private markets. He has experience as an allocator across a range of institutional types, from wealth management firms to pensions and endowments, and helped launch the venture capital program for the Texas Municipal Retirement System. Other past experiences of his have included leading finance/operations for a venture-backed startup, in addition to vetting investments for a family office and working with their portfolio companies. Over the years he has also written about his investing experience on Medium and Substack.
He is a graduate of the University of Notre Dame as well as the Kauffman Fellows Program, an executive education program focused on venture capital and innovation leadership. He wears many hats.
[00:00] Intro [03:57] The origin of Peter’s nickname [05:16] How was boxing formative to who Peter is today? [07:25] The art of the first conversation with a GP [11:46] How did TMRS deploy $1B into VC and PE annually? [19:45] Looking at the underlying portfolio of companies [24:06] How overlap in venture portfolios affect re-up decisions [26:55] Marks from an LP perspective [30:52] Qualitative vs quantitative information [34:45] Signal vs noise in the private markets [40:46] When Peter shaved his head in front of an entire lecture hall [45:09] The most recent update to the Peter OS [51:17] Thank you to Alchemist Accelerator for sponsoring! [53:53] If you enjoyed the episode, consider dropping a like, comment or share as it really helps me create content that is interesting to you
“Don’t overweight the quantitative over the qualitative.” – Peter Teneriello
“It’s not to be in the consensus out of a misguided sense of self-preservation; it’s approaching your life’s work with creativity and conviction and treating it like the art that it is.” – Peter Teneriello
Last week, Youngrok and I finally launched our episode together on Superclusters. In the midst of it all, we wrestle with the balance between the complexity and simplicity of questions to get our desired answer. Of course, we made many an allusion to the DGQ series. One of which, you’ll find below.
In many ways, I started the DGQ series as a promise to myself to uncover the questions that yield the most fascinating answers. Questions that unearth answers “hidden in plain sight”. Those that help us read between the lines.
Superclusters, in many ways, is my conduit to not only interview some of my favorite people in the LP landscape, but also the opportunity to ask the perfect question to each guest. Which you’ll see in some of the below examples.
Asking Abe Finkelstein about being a Pitfall Explorer and how it relates to patience (1:04:56 in S2E1)
What Ben Choi’s childhood was like (2:44 in S1E6) and how proposing to his wife affects how he thinks about pitching (1:05:47 in S1E6)
How selling baseball cards as a kid helped Samir Kaji get better at sales (45:05 in S1E8)
In doing so, I sometimes lose myself in the nuance. And in those times, which happen more often than I’d like to admit, the questions that yield the best answers are the simplest ones. No added flare. No research-flexing moments. Where I don’t lead the witness. And I just ask the question. In its simplest form.
For the purpose of this essay, to make this more concrete, let’s focus on a question LPs often ask GPs.
“Tell me about this investment you made.“
In my mind, ridiculously simple question. Younger me would call that a lazy question. In all fairness, it would be if one was not intentionally aware about the kind of answer they were looking to hear OR not hear.
The laziness comes from regressing to the template, the model, the ‘what.’ But not the ‘why’ the question is being asked, and ‘how’ it should be interpreted. For those who struggle to understand the first principles of actions and questions, I’d highly recommend reading Simon Sinek’s Start with Why, but I digress.
Circling back, every GP talks about their portfolio founders differently. If two independent thinkers have both invested Company A, they might have different answers. Won’t always be true, but if you look at two portfolios that are relatively correlated in their underlying assets AND they arrive at those answers in the same way, one does wonder if it’s worth diversifying to other managers with different theses and/or approaches.
But that’s exactly what makes this simple question (but if you want to debate semantics, statement) special. When all else is equal, VCs are left to their own devices unbounded from artificial parameters.
Then take that answer and compare and contrast it to how other GPs you know well or have invested in already. How do they answer the same question for the exact same investment? How much are those answers correlated?
It matters less that the facts are the same. Albeit, useful to know how each investor does their own homework pre- and post-investment. But more so, it’s a question on thoughtfulness. How well does each investor really know their investments? How does it compare to the answer of a GP I admire for their thoughtfulness and intentionality?
(Part of the big reason I don’t like investing in syndicates because most outsource their decision-making to larger logos in VCs. On top of that, most syndicate memos are rather paltry when it comes to information.)
The question itself is also a test of observation and self-awareness. How well do you really know the founder? Were you intentional with how you built that relationship with the founder? How does it compare to the founder’s own self-reflection? It’s also the same reason I love Doug Leone’s question, which highlights how aware one is of the people around them. What three adjectives would you use to describe your sibling?
Warren Buffett once described Charlie Munger as “the best thirty-second mind in the world. He goes from A to Z in one go. He sees the essence of everything even before you finish the sentence.” Moreover in his 2023 Berkshire annual letter, he wrote one of the most thoughtful homages ever written.
As early-stage investors, as belief checks, as people who bet on the nonobvious before it becomes obvious, we invest in extraordinary companies. I really like the way Chris Paikdescribes what we do. “Invest in companies that can’t be described in a single sentence.”
Invest in companies that can’t be described in a single sentence
And just like there are certain companies that can’t be described in a single sentence — not the Uber for X, or the Google for Y — their founders who are even more complex than a business idea cannot be described by a single sentence either. Many GPs I come across often reduce a founder’s brilliance to the logos on their resume or the diplomas hanging on their walls. But if we bet right, the founders are a lot more than just that.
Of course, the same applies to LPs who describe the GPs they invest in.
In hopes this would be helpful to you, personally some areas I find fascinating in founders and emerging GPs and, hell just in, people in general include:
Their selfish motivations (the less glamorous ones) — Why do this when they can be literally doing anything else? Many of which can help them get rich faster.
What part of their past are they running towards and what are they running away from?
All the product pivots (thesis pivots) to date and why. I love inflection points.
If they were to do a TED talk on a subject that’s not what they’re currently building, what would it be?
Who do they admire? Who are their mentor figures?
What kind of content do they consume? How do they think about their information diet?
What promises have they made to themselves? No matter how small or big. Which have they kept? Which have they not?
How do they think about mentoring/training/upskilling the next generation of talent at their company/firm?
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.
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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.
