Developing Taste as an LP

taste, donut, bite

Brian Chesky did a fireside chat recently where he talks about how he hired for roles at Airbnb, especially in the early days. To which, I highly recommend you checking the above link. Lots of nonobvious lessons worth noting. One thing especially stood out. Probably due to the recency bias of having a few friends text me who were thinking about investing in their first fund.

“Executives have more experience bullshitting you than you have experience detecting their bullshit. So it’s like an asymmetric game where you’re a white belt fighting a black belt and they’re just going to punch you in the face repeatedly.”

In a similar way, a lot of new LPs in venture have also yet to develop their taste for quality in the venture asset class. If you’ve never hired an executive, you have no idea what a great executive looks like. And if you’ve never invested in a fund, or seen a few, you have no idea what a great fund looks like. Most GPs, given the volume of LPs they pitch to, have more experience bullshitting you as an LP than you have experience detecting their bullshit.

And that’s okay. Everyone starts off this way. So the question then becomes how do you develop taste?

  1. Talk to as many as you can. Don’t overoptimize for quality. You have no idea what quality looks like, so don’t delude yourself that you do. Ask friends who they’ve talked to. Ask Twitter. And ask the GPs you talk to who are friends they respect who are also building a fund. Hell, try your luck at asking certain “influencers” in the space if they have recommendations. Realistically, if you raise your hand and say you’re an LP, GPs will flock to you. In 2024, deal flow, as measured by quantity, isn’t really hard for any LP out there.
  2. Prioritize references.

On the first point, as is the advice I give most first-time angel investors investing in startups, don’t invest in the first startup you see. Unless it’s for a reason outside of financial gain. To support a friend. To learn. For impact. To give back. All great reasons. But not if because your friend told you to.

Along the same thread, don’t invest in the first fund you see. Talk to at least 30-50 fund managers. Get a good understanding of what the average fund looks like. What is actually special about a GP versus what they say is special. Most of the time when someone claims that they are the special one, they usually aren’t. For instance, only [insert big name fund] invests with us. Or we are the only [insert industry or function] fund. Hell, if anyone gives you any sort of superlatives, they’re usually wrong. Only. Always. Best. Most. I’m sure there are more, but the rest are escaping me.

Secondly, prioritizes references over your initial judgment when interviewing and doing diligence. Dan Stolar from Colibri and I had a conversation recently about references, where the questions you ask are paramount. If you’re short on time, I’d recommend starting from the 25:50 mark.

In short, to existing LPs, ask:

  1. How did you get to conviction?
  2. Who else did you talk to that were comparable to this GP before you reached an investment decision?
  3. Is there anything you learned about the team after you made the investment?
  4. What kind of person do you think they should bring onboard either in the next fund or after they get to a close?
  5. Would it be possible to share your investment memo with me?
  6. What were some of the pushbacks or hesitations when this deal reached your investment committee?

To LPs more broadly:

  1. What are your primary motivations to be an LP in venture?
  2. How do you think about portfolio construction?
  3. Who are the GPs you’ve talked to that seem to stand above the rest? And why?

To co-investors/other GPs:

  1. How often do you share deals with this GP?
  2. How often do they share deals with you?
  3. Who are your top 3 emerging managers that you love seeing deals from and why?
  4. Is there an emerging manager you would hire to be a partner or GP at your firm if you could?
  5. How would you rate this GP on a scale of 1-10, with 10 being perfect?
    • What would get this GP to a 10?
  6. Did you or have you considered investing in their fund?
  7. What are some of this GP’s hobbies that I might not guess?
    • This shows you how well people know each other. You can also use this question for other reference archetypes.

To former colleagues and friends:

  1. If you were to hire someone under this GP, what traits or skillsets would you look to hire for?
  2. I hate surprises. Is there anything that could go wrong I should know now about this GP, so that I wouldn’t be surprised when it happens?
  3. Who is someone you would hire or work together again in a heartbeat?
    • Notice if they mention that GP. You don’t have to probe as to why they didn’t mention if they didn’t. But worth noticing. Also probably worth talking to that person they did mention to keep a strong talent network around you.

Obviously the above list isn’t all-inclusive. But nevertheless I imagine they’ll be good starting points. Also, I want to note that going deep is often more insightful than going wide.

Remember, almost everyone is incentivized to say good things about others. Or at least, there is little to no incentive to talk smack about anyone you know. So finding the best way to ask questions that unearth different perspectives and facets of a person is important.

Funnily enough and unintentionally, last week I wrote a similar post from the perspective of a GP, this one happened to be more for the LP.

Photo by Thomas Kelley on Unsplash


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


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

The Difference Between GPs who Can and Should Raise | Dan Stolar | Superclusters | S4E3

dan stolar

“GPs and LPs are both equally busy, but different kinds of busy where on any given day, we’ll probably have the same amount of calls and all these things going on, but [LPs are] going to know [they’re] busy three months ahead of time and a GP won’t.” – Dan Stolar

Dan Stolar is a Principal at Colibri Equity Ventures, a single family office based in NYC and San Diego. Dan leads the venture capital strategy and also participates in all alternative private investments, including sports investing and private equity. As part of the venture strategy, Dan particularly focuses on investing in emerging venture capital funds. Since launching the strategy in late 2022, the firm has invested in ~15 managers. Dan started his venture capital journey as an intern at Viola Credit, a venture debt fund in Tel Aviv, before spending time in investment banking at Peter J. Solomon Co. (now Solomon Partners) where he focused on consumer and retail mergers & acquisitions. After banking, Dan spent ~5 years at Alpha Partners, a late-stage venture firm that partners with early stage managers helping them follow on in their late stage deals. Dan is still involved with Alpha as a Venture Partner. Dan is a proud New Jersey native, and a graduate of the University of Michigan (Go Blue!).

You can find Dan on his socials here:
LinkedIn: https://www.linkedin.com/in/danielstolar/
X/Twitter: https://x.com/dan_stolar

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
[02:29] Dan’s high school scavenger hunt
[07:33] Telltale sign of excellence #1 in a GP
[09:29] How telling intros are
[11:16] Telltale sign of excellence #2
[13:46] Underwriting a Fund II vs Fund I
[17:40] What do LPs think of deadlines that GPs set for closes?
[18:48] What does a no that turns into a yes look like?
[22:26] Not all positive references are created equal
[25:50] Questions to ask an existing LP in a GP during diligence
[28:30] Reasons an investor would leave a firm
[30:13] The difference between a GP who can and should raise a fund
[33:01] Fund track records that aren’t scalable
[33:56] The one question that most GPs don’t have a good answer to
[35:09] Responsiveness between a GP and an LP
[38:39] Inbox overload for LPs
[41:21] What trivia does Dan excel at?
[45:07] Biking through snowstorms in NYC
[48:08] Thank you to Alchemist Accelerator for sponsoring!
[49:08] If you learned something from this episode, it would mean a lot to me if you could share it with one friend who might also enjoy it!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“I think a lot about someone’s transactional ability – or how transactional they actually are – correlates with how successful they’re going to be. […] Who you lift up is a much better indication of how good you are.” – Dan Stolar

“Getting an LP is like pulling a weight with a string of thread. If you pull too hard, the string snaps. If you don’t pull hard enough, you don’t pull the weight at all. It’s this very careful balancing act of moving people along in a process.” – Dan Stolar

“GPs and LPs are both equally busy, but different kinds of busy where on any given day, we’ll probably have the same amount of calls and all these things going on, but [LPs are] going to know [they’re] busy three months ahead of time and a GP won’t.” – Dan Stolar

“When a GP passes on a deal, the deal’s done. You’re not going to see that company again. When I pass on a fund, I might see that fund for another 12 years. So I’m going to be on those updates and those check-in calls.” – Dan Stolar


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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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.

Overwhelming and Underwhelming — When to Know You Are Just “Whelming”

fireworks, light, night

One of my favorite sections in Danny Meyer’s Setting the Table (H/T to Rishi and Arpan from Garuda who not only gifted me that book, but also one of the nicest bookmarks I own today) is when he talks about whelmers.

“I ask our managers to weigh one other critical factor as they handicap the prospect. Do they believe the candidate has the capacity to become one of the top three performers on our team in his or her job category? If people cannot ever develop into one of our top three cooks, servers, managers, or maître d’s, why would we hire them? How will they help us improve and become champions? It’s pretty easy to spot an overwhelmingly strong candidate or even an underwhelmingly weak candidate. It’s the ‘whelming’ candidate you must avoid at all costs, because that’s the one who can and will do your organization the most long-lasting harm. Overwhelmers earn you ravers. Underwhelmers either leave on their own or are terminated. Whelmers, sadly, are like a stubborn stain you can’t get out of the carpet. They infuse an organization and its with mediocrity; they’re comfortable, and so they never leave; and, frustratingly, they never do anything that rises to the level of getting them promoted or sinks to the level of getting them fired. And because you either can’t or don’t fire them, you and they conspire to send a dangerous message to your staff and guests and ‘average’ is acceptable.”

In an industry where everyone is incredible — in many ways, you can’t, or at least it’s really hard to, be a GP without being overwhelming in your past in one way or another… INcredible becomes credible. So, it’s quite hard when you have a limited sample size to know who is incredible among the already incredible.

Almost everyone today is overqualified for the job, compared to the 1970s, 80s, and 90s, when most were underqualified.

So, unless you’ve been an LP, how do you know if you’re overwhelming versus just whelming?

  1. LPs who have seen at least 200 funds in the last 2-4 years tell you you’re the “only” one who is pursuing this strategy
    • They have large enough of a sample size to make an assessment. While not perfect, it’s enough to be in rarified air.
  2. You’ve been to the major LP/GP conferences (i.e. RAISE, Bridge, All Raise, SuperReturn / SuperVenture, Upfront Summit, Milken, EMC Summit, etc.) and have seen how other GPs pitch where you personally have a sample size of at least 100.
    • Even better, if you’ve been to the Demo Days or showcases for Coolwater, Recast, VC Lab, just to name a few, and you’ve seen other GP’s pitches
    • Do note what GPs say on podcasts are usually (in my experience) what they pitch to LPs.
  3. You can cold email LPs and they’ll respond.
    • LPs are notoriously closed off to cold emails. As an institution that makes only 1-3 new investments per year in an asset class, it doesn’t make sense for them to keep the doors open as much as venture investors do for founders. And even then, a lot of VCs are also averse to cold emails. That said, if you’re a GP that consistently gets meetings booked from cold emails, you might have something special.
    • More often than not, admittedly, this is due to a strong brand, either via media, personal brand, strong returns, or word of mouth.
    • Important to note that you’re never as good as they say you are, but you’re also never as bad as they say you are.
  4. When you are THE first call exited founders ($100M+ exits) make when they’re brainstorming their next company
    • Them needing a sparring partner on their next career move also counts.
    • You getting invited to whatever large event they host next does not. Including birthday parties, weddings, etc. As much as it feels good to me, you’re not overwhelming. If it puts things into perspective, I get invited to these, and I know I’m not an “overwhelming” venture investor.
    • Also if you’re the fifth person they call, you’re just “whelming.”
  5. You are cited by other investors and founders alike as the source material of an ideology or a framework.
  6. Different founders (or people in general) reach out to you consistently on topics that is not fundraising/them pitching you. In fact, they may never reach out to you on fundraising because you’re known for excellence in other areas.
  7. The best talent in the world want to work with you and they’ll find any way to do so. They’ll say things like, “What if we worked together on a small project first together?” or “How about this together?” The same world-class talent will not only prioritize your goals but also not forsake their own. ‘Cause frankly, the world’s best have their own pursuits and they are transparent and honest about it. Beware of people whose goal you don’t know and those that “give up” their dreams for yours.
  8. You have a memory like a steel trap. You quote books, passages, movies, lessons, anecdotes, stories, history, podcasts, presidential speeches from back in the day, and music in ways most people cannot fathom but make complete sense. You quote in ways where people wonder if you have photographic memory or a chip in your brain, but you actually don’t.
    • This is more or less intellectually “overwhelming”, although overwhelming may not be the right terminology. But someone who is profusely well-read and cultured in a diverse amount of material. Think Da Vinci. Or maybe a modern-day equivalent, Patrick Collison, David Senra, or Ben and David on Acquired.

The one thing I won’t include on this list, while undeniably “overwhelming,” is intuition. People with phenomenal intuition are just different. Overwhelmingly different. But in the world of venture, the word intuition is often overused and has lost its true meaning. Many investors who bet well in hindsight attribute luck to intuition. And hell, the reason I’m not including it in the above list, is that many investors think they’re heavily intuitive, which in my experience usually means:

  1. They hate math. Spreadsheets and the like. In fact, they’re likely just to be bad at it.
  2. They hate diligence. The homework that’s actually required to be a great investor.
  3. If they’re pre-economic success, they’re often spinning a tale to us. Or worse, lying to themselves.
  4. If they’re post-economic success, there’s a good chance they have hindsight bias.

That said, there are a rare few number of times where I meet someone (often not an investor) and they’re able to deduce the person I am with a glance with very little other context. To me, that feels like magic. Something that very few have. But at the same time, I do believe can be trained.

Photo by Jeffrey Hamilton on Unsplash


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


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

The Case for Concentrated Portfolios | Jeff Rinvelt | Superclusters | S4E2

jeff rinvelt

“The line that sits for me is you got to pick well, you got to coach well, and then you got to finance well – and the financing includes the exit.” – Jeff Rinvelt

Jeff Rinvelt is a partner at Renaissance Venture Capital an innovative venture capital fund of funds. Jeff’s diverse background in venture capital and technology and his experience working in various start-up ventures uniquely position him to advise startups. In addition, Jeff is quite active in the Michigan start-up community, volunteering his time to mentor young entrepreneurs, judge pitch competitions, and guest lecture student classes and organizations. Through Jeff’s work on the Fund, his volunteer efforts, and his role as the chair of the Michigan Venture Capital Association’s board of directors, his passion for fostering a productive environment for venture capital investment in the State of Michigan is evident.

You can find Jeff on his socials here:
Twitter: https://twitter.com/rinvelt
LinkedIn: https://www.linkedin.com/in/rinvelt/

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
[02:28] When Jeff went from engineering to finance
[06:26] An introvert in an extroverted industry
[07:42] Jeff’s transition from founder to investor
[11:06] The need for a fund of funds in Michigan
[13:54] Why start a fund of funds instead of joining another fund
[15:32] The minimum viable fund size for a fund of funds
[21:46] Renaissance’s portfolio construction
[24:15] Why Renaissance measures GP performance by net IRR
[28:18] How does Jeff assess a GP’s portfolio construction model?
[31:20] Jeff’s stance on reserves
[34:39] Who is the exit manager?
[37:22] Should VCs be public market investors?
[42:43] What would Jeff do if he had evergreen capital?
[44:01] Do the best GPs in Jeff’s portfolio send the deck first or have the meeting first?
[45:11] Why is Jeff trying to break your heart?
[48:32] Thank you to Alchemist Accelerator for sponsoring!
[49:33] If you enjoyed the episode, please do share this episode with ONE other person you think would enjoy it.

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Net IRR is the one that’s probably going to work. It takes a while for it to bake though – 5 or 6 years in.” – Jeff Rinvelt

“The line that sits for me is you got to pick well, you got to coach well, and then you got to finance well – and the financing includes the exit.” – Jeff Rinvelt

On portfolio construction models… “We are not in the Monte Carlo simulation game at all; we’re basically an excel spreadsheet.” – Jeff Rinvelt

“A lot of those skills [to be a fund manager] are already baked in. The one that wasn’t baked in for a lot of these firms was the exit manager – the ones that help you sell. […] If you don’t have it, there should be somebody that it’s their job to look at exits. ” – Jeff Rinvelt


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
Follow Superclusters on TikTok: https://www.tiktok.com/@super.clusters
Follow Superclusters on Instagram: https://instagram.com/super.clusters


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


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

Hypoxic Training

swimming, diving

Back when I was still swimming competitively, one of the drills our swim coach always had us do was a set of hypoxic drills. The two that left the most indelible marks were:

  1. 10 sets of 100 yards, broken down by 25 yards. Lap 1, breathe every 5 strokes. Lap 2, every 3 strokes. Lap 3, every 7 strokes. And Lap 4, every 9 strokes.
  2. 20 sets of 55 yards. You start with a flip turn into the wall. First 25 yards (Lap 1), no breaths allowed. Second 25 (Lap 2), you’re allowed to only take one breath.

Naturally, those drills usually left me the most exhausted. Not only did I find myself catching my breath, we also had to swim those on specific intervals, which left less than five seconds of rest at best, while swimming at 80% our max speed.

All that to say, it was a set of exercises that trained us to hold our breath. We had less oxygenated blood. Naturally, it was harder to exert our max strength and endurance. But it tested our ability to weather exhaustion.

Just like today.

Our venture ecosystem needs oxygen. The whole industry is holding their breath. For IPOs. like Stripe’s. Which may be unlikely to happen in the near future given Sequoia’s recent share acquisition. Software acquisitions have also hit an all-time low, leaving LPs starved for liquidity from the major private market exit paths.

Source: Tomasz Tunguz / Theory Ventures

And of the few “acquisitions” that are happening, they’re done to circumnavigate anti-trust laws. As Tomasz points out, “they hire the core team [in other words the founding team], license the technology, but the majority company continues to operate as a separate entity.” In addition, a number of companies also need to get re-priced in the market, having raised in 2020 and 2021 on over three-year runways. Which to their credit, was the common advice given by VCs during that era.

Election season does not make this Mexican standoff any less strenuous. How will it impact the global economy? And who’s the last to hold the bag with all these hot AI deals? We all know AI has low margins and requires and immense amount of compute to deliver the results that we expect, but how much longer will this need to go on?

Who knows?

At least until we get to breathe again. The consensus seems to be Q1 2025. But until we have oxygen again, this is the hypoxic training that our world will have to endure for the foreseeable future.

In the words of my coach, “focus on distance per stroke.” In other words, executional discipline. Do more with less.

Photo by NEOM 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.

DGQ 24: Guessing a number between 1 and 100

lock, numbers

Eight years back, at least at the time of publishing this blogpost, Steve Ballmer, former CEO of Microsoft, shared one of his favorite interview questions.

“I’m thinking of a number between 1 and 100. You can guess. After each guess, I’ll tell you whether high or low. You get it the first guess, I give you five bucks. [Second guess], four bucks. Three. Two. One. Zero. You pay me a buck. You pay me two; you pay me three… And the question is, do you want to play or not? What’s your answer?”

While he didn’t go too much in depth on all the answers he’s gotten to it over the years, I imagine different people would have given different proposals on how the game might be played. Of course, the classic engineer is likely to approach it was as an expected value problem.

Most people will lose money. There are far more numbers to guess on which one loses than wins. The question really comes down to… do you know the odds of the game you play?

I find it interesting as an investor to hypothetically ask to founders and/or GPs. That said, I never did. But equally so, I usually spend the first conversation with an entrepreneur (whether the product be software or a fund model) trying to understand a person’s motivations. And, if they understand the rules of the game.

Those who don’t understand the rules will often jump head first in, and take care of the consequences later. Asking for forgiveness than for permission. An attitude that is more excusable in a startup founder than a fund manager.

Those who do understand will take a more measured approach. It’s interesting how little some people understand the game they’re playing. Be it in a two-year financial projection that encapsulates all their assumptions, or a portfolio construction model to understand the enterprise value to return the fund 3X.

For the former, it’s less so of how accurate a financial projection slide is. Hell, your guess is as good as mine. But I always ask founders to unpack it to understand how they’re thinking about the future as a function of their reality today.

For the latter, it’s to understand the true power of the power law, no pun intended. For instance, if you have a $10M fund, writing 20 checks of $500K for 5% ownership. Obviously, I’m assuming a bunch of things for the sake of keeping the math simple. No fees, no recycling, no reserves, and so on. You need to return $50M to 5X your fund. Accounting for 80% dilution, you’ll own 1% on exit. So you need $5B in enterprise value. Given the power law, one of out of the 20 companies should get to at least $3-4B in exit value.

Then again, those who understand the game too well will never take the risk necessary for serendipity to stick.

There’s an interesting blogpost an LP shared with me for my blogpost on evergreen content that VCs and LPs consume. A piece written by the legendary Graham Duncan. “The Playing Field.” A piece I highly recommend reading, even if to shape your own thinking about how the game you play evolves over time. In it, a line worth underscoring.

“[I]t’s the way you learn to play the cards you’ve been dealt, rather than the hand itself, that determines the worth of your participation in the game.”

Photo by Towfiqu barbhuiya 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.

DGQ 23: What’s the most interesting question you’ve been asked so far?

cactus, different, unique

I use this question quite often as a discovery tool. My job as an early-stage investor is to find crazy, interesting people building interesting things. By the time things look less crazy (at least at face value, without digging), I’m likely too late.

To founders who are fundraising, I often ask this question with respect to VCs. Most VCs default to the usual.

Tell me about your company.

How much revenue do you have? Growth rate?

Tell me about your 2-year plan. Your financial projections.

Tell me about your competitors.

How much are you raising?

Who else is investing?

And I’ve probably missed a plethora of usual suspects when it comes to questions VCs ask founders. But I love people who ask different sets of questions. People who think different, see different, and as such ask different. How are they slicing the cake differently? What might these people be seeing that most others are not? And then, I go back and reflect… is there alpha in that way of thinking.

But first, it’s about the questions. Some examples of such… here, here, here, and here, and also here and here.

So when I ask, “What’s the most interesting question you’ve been asked so far?” to founders, they can help me uncover new VCs I may not have noticed before. Probably investing in ways the industry has not seen before. And probably also investing in companies uncorrelated with most others. At least in the early stages. When I ask it to GPs, I can find LPs whose portfolios may look different from others. Or at the very least, will have arrived at their conclusion differently than their peers.

Photo by Nick Karvounis 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.

Starting from Yes versus No

stoplight, green, red, yes, no

Last week, I was chatting with an LP about decision-making processes at institutional LPs, whether a large family office or a pension or an endowment. And I asked her:

“When you come across a new investment opportunity, do you often find yourself starting from a yes and working to find ways to disprove yourself to get to a no? Or do you start from a no, then spend the next few years working your way to get to a yes?”

(To be honest, I could have phrased the question. But alas, you get the gist.)

She gave a light chuckle. Thought for a moment. And said, “In the first conversation I have with a GP, I either get to a quick no or a tentative yes. And in the next few months, I try to find signs of why this investment could be a no. But if I don’t find any strong disproving evidence in that exploration, that’s when we choose to invest.”

Of course, she’s not alone. I haven’t actively gone out to measure the distribution. But out of 20 or so LPs I’ve asked, I’d say anecdotally, it’s about half who start from a yes, and half who start from a no.

There’s no hard and fast rule here. But what I seemed to notice is that it depends heavily on how easily people get to conviction.

Some people are more prone to saying yes. They get easily excited about new opportunities. The feeling of love at first sight. As such, their investment process accounts for that by delaying gratification and impulse purchases. The discipline of their investment process allows to take time to find clues that may either prove or disprove their intuition.

Among thousands, if not tens of thousands of opportunities, for others, it’s easier to say no. Most LPs don’t have a time horizon they have to commit capital before, barring fund of funds, and potentially some large institutions who act as fiduciaries for others’ capital. Unlike a GP whose mandate is potentially stage-specific, to most LPs, a Fund I commitment versus a Fund II or a Fund III is virtually the same to them. If a pre-see-only fund says no at the pre-seed, they lose that window of opportunity because they’re not allowed to invest net new checks at seed or Series A.

For LPs, this takes the possibility of a near-term transactional relationship out. Then as the relationship matures over time, one might stumble across something about a GP that gets them over the activation energy to dig deeper. And eventually, when enough evidence is collected, they’ll pull the trigger. More often than not, it’s not “enough evidence,” but rather enough time to realize the one or two brilliant things about a GP.

Photo by Diane Picchiottino 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.

When VC Funds Become Firms, Part 2 | Lisa Cawley, Ben Choi, Jaclyn Freeman Hester | Superclusters

lisa cawley, ben choi, jaclyn freeman hester

“We overcomplicate almost nothing as LPs. And this is a criticism of myself. And I think we oversimplify almost everything. Because by definition, we’re the customer of the end product. […] LPs watch the movie, but don’t read the book.” – Ben Choi

We’re doing a three-part series with some of our fan favorites over the last three seasons on the LP perspective of succession-planning and VC firm-building.

Lisa Cawley is the Managing Director of Screendoor, a highly respected LP of GPs, investing in firm-builders by firm-builders, with a unique model for partnering with allocators to access the emerging manager ecosystem.

Ben Choi manages over $3B investments with many of the world’s premier venture capital firms as well as directly in early stage startups. He brings to Next Legacy a distinguished track record spanning over two decades founding and investing in early-stage technology businesses.

Jaclyn Freeman Hester is a Partner at Foundry. 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.

You can find Lisa on her socials here:
LinkedIn: https://www.linkedin.com/in/31mml/
Screendoor: https://www.screendoor.co/contact

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

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.

You can also find Part 1 of this 3-part mini series here.

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[02:00] Questions Ben asks GPs to see if they’re thinking long-term
[06:50] Questions Jaclyn asks GPs to assess long-term thinking
[09:45] What does leverage look like for a GP?
[20:13] The role of AI internally at a firm
[21:06] Advice to people looking to take junior VC roles
[25:33] Questions Lisa asks GPs to assess long-term thinking
[29:19] When does a fund turn into a firm?
[31:26] Lisa: What do LPs often oversimplify vs overcomplicate about firm-building?
[35:31] Ben’s answer to oversimplification vs overcomplication
[41:00] What do emerging and established GPs oversimplify and overcomplicate?
[45:06] Thank you to Alchemist Accelerator for sponsoring!
[46:07] If you can’t wait for Part 3 of this conversation, leave us a like or comment!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“How do you get the most out of the least amount of people? […] I don’t think getting more bodies solves it. I think getting high leverage from a smaller set of resources is better.” – Jaclyn Freeman Hester

“If I hire someone, I don’t really want to hire right out of school. I want to hire someone with a little bit of professional experience. And I want someone who’s been yelled at. […] I don’t want to have to triple check work. I want to be able to build trust. Going and getting that professional experience somewhere, even if it’s at a startup or venture firm. Having someone have oversight on you and [push] you to do excellent work and [help] you understand why it matters… High quality output can help you gain so much trust.” – Jaclyn Freeman Hester

“What’s your right to win? Why are you going to be a founder and talent magnet? Why does the world need you as a firm? Why does the world need you as a VC? And how do you define success?” – Lisa Cawley

“We overcomplicate almost nothing as LPs [about the firm building process]. And this is a criticism of myself. And I think we oversimplify almost everything. Because by definition, we’re the customer of the end product.” – Ben Choi

“LPs watch the movie, but don’t read the book.” – Ben Choi

“Ultimately, Job #1 as an emerging GP is to be a great investor. We want you to be a great investor that lasts the test of time. But if you’re a mediocre investor that lasts the test of time or a great investor that doesn’t last the test of time, we prefer the second.” – Ben Choi


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
Follow Superclusters on TikTok: https://www.tiktok.com/@super.clusters
Follow Superclusters on Instagram: https://instagram.com/super.clusters

When VC Funds Become Firms, Part 1 | Lisa Cawley, Ben Choi, Jaclyn Freeman Hester | Superclusters

“There’s this amazing, amazing commercial that Michael Phelps did, […] and the tagline behind it was ‘It’s what you do in the dark that puts you in the light.’” – Lisa Cawley

We’re doing a three-part series with some of our fan favorites over the last three seasons on the LP perspective of succession-planning and VC firm-building.

Lisa Cawley is the Managing Director of Screendoor, a highly respected LP of GPs, investing in firm-builders by firm-builders, with a unique model for partnering with allocators to access the emerging manager ecosystem.

Ben Choi manages over $3B investments with many of the world’s premier venture capital firms as well as directly in early stage startups. He brings to Next Legacy a distinguished track record spanning over two decades founding and investing in early-stage technology businesses.

Jaclyn Freeman Hester is a Partner at Foundry. 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.

You can find Lisa on her socials here:
LinkedIn: https://www.linkedin.com/in/31mml/
Screendoor: https://www.screendoor.co/contact

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

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
[02:03] The job that goes unseen by others at a VC firm
[09:01] The psychology of curiosity
[11:12] The story of Charlie Munger and Robert Cialdini
[14:17] Lisa’s perspective on the intangibles of firm-building
[17:41] Heidi Roizen and why glassblowing builds relationships
[21:09] The people you surround yourself with
[23:06] Jaclyn’s perspective on the intangibles
[26:23] Examples of how to communicate strategy drift
[27:34] Ben’s perspective on the intangibles
[33:19] The metric many LPs don’t use but should use to evaluate GPs
[36:16] Thank you to Alchemist Accelerator for sponsoring!
[37:17] If you enjoyed Part 1, and want to see Part 2 and 3 sooner, leave a like or a comment!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“The job and the role that goes most unseen by LPs and everybody outside of the firm is the role of the culture keeper.” – Ben Choi

“You can map out what your ideal process is, but it’s actually the depth of discussion that the internal team has with one another. […] You have to define what your vision for the firm is years out, in order to make sure that you’re setting those people up for success and that they have a runway and a growth path and that they feel empowered and they feel like they’re learning and they’re contributing as part of the brand. And so much of what happens there, it does tie back to culture […] There’s this amazing, amazing commercial that Michael Phelps did, […] and the tagline behind it was ‘It’s what you do in the dark that puts you in the light.’” – Lisa Cawley

“At the end of the day, the job is to take a pile of money from your LPs and give them a bigger pile. And giving them back a really big pile is the legacy thing. […] And consistently insane returns are hard. That, to me, are the firms that go down in history.” – Jaclyn Freeman Hester

“In venture, LPs are looking for GPs with loaded dice.” – Ben Choi


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
Follow Superclusters on TikTok: https://www.tiktok.com/@super.clusters
Follow Superclusters on Instagram: https://instagram.com/super.clusters