When she complains about the dishes…

dishes

This is a repost of a piece I wrote earlier this week on my investing topic only blog that seemed to get good feedback, so sharing here as well, in hopes that it is helpful to you as well.

The post is for GPs who’ve gotten rejections from LPs, but I think the analogy stands if you’re a founder hearing back from a VC, or anyone who is doing any kind of fundraising or sales.


One of the most memorable pieces of relationship advice Iโ€™ve gotten is that line. โ€œWhen she complains about the dishes, itโ€™s not about the dishes.โ€

By the time your spouse complains about the dishes, itโ€™s a culmination of other pent-up emotions simmering at the surface. And when she says it’s the dishes, itโ€™s not. Potentially it never was. But it may have been the reason that tipped her over the edge.

That said, this is not a post about relationships. Iโ€™m not a marriage counselor or a relationship coach. This is a post about rejections. And all the reasons that come with rejections. Or more specifically, about LPs passing on GPs. Or hell, VCs passing on founders.

And yes, Iโ€™m going to use gendered language but itโ€™s purely for the purpose of extending this analogy and lesson my friend gave me. So I hope you allow me this literary liberty.

When she complains about you being too early, itโ€™s that she never had conviction over the deal. When she says you need more traction (track record), itโ€™s because she couldnโ€™t see why you would see and win the most interesting deals in your space. What you say has yet to be proven by what you did. So, the underwriting will start now for what you will do. She doesnโ€™t trust you can execute against what you promised. Youโ€™re either talking a big game (using superlatives that feel disingenuous) and/or you create a feeling of naivete. Be assured that the best allocators will be keeping track of what you promised before. Even if you, as a GP, rewrite your Docsend pitch deck. Admittedly, still, most wonโ€™t.

You will wonder why she backs others with no track record and no prior relationship with her. And 9 out of 10 times, itโ€™s a communication issue in the first (few) meetings. You gave her no reason to generate enough dopamine that would get her to act outside of the meeting.

When she complains about there being higher priority opportunities, your strategy doesnโ€™t align with the organizationโ€™s strategy. She likely did some work, and her initial work and/or references discounted the initial enthusiasm she had. She didnโ€™t know how to say no politely and without seeming like an asshole. So only after a few meetings, and only after sheโ€™s felt like sheโ€™s given you the time and respect she thinks you deserve (whether you accept it or not), she can finally pass. Your problem is you never figured out what her motivations are. What she wants in her career. What her โ€œfamilyโ€ (organization) wants of her. What keeps her up at night. Why she wants to go to work every Monday.

When she complains that there isnโ€™t enough capital to left to deploy, itโ€™s the fact you arenโ€™t good enough to be an exception that would help her raise her next vehicle or to get board approval. Excluding institutions (including family offices) who own their own pool of evergreen capital, anyone who has to ask other stakeholders for more capital to invest has at least 20-30% left to deploy when they go out to raise their next vehicle. The primary motivator for the remainder of capital are people or opportunities that best highlight an allocatorโ€™s promise to their stakeholders. Fund-of-funds promise access. That means either a multi-million dollar allocation in Anthropic or an individual (usually spinout, but sometimes highly reputable founder/operator) whoโ€™s been early in generational opportunities. Others, like multi-family offices, depending on their mandate, either promise access or their ability to pick great pickers, which means 5X+ DPI in 5 years in a prior fund is extraordinarily exciting. Realized IRR or DPI matter a lot.

When she gives you a whole list of reasons as to why theyโ€™re passing, itโ€™s because of the first reason, but she needed a laundry list of reasons to justify the one small thing she felt like she would get judged for. But that small thing came up as a recurring theme again and again, among references, among pushback from her investment committee, among her own doubts she never unearthed with you. One reason is all you need to pass. One reason is all you need. And sometimes, itโ€™s the dirty laundry (i.e. gossiping). Or the speed of your communication. Sometimes, itโ€™s the fact that you boast about another LP competitor in front of them. Sometimes, itโ€™s the fact that you forgot what you talked about in the last meeting. The reasons will always feel like bullshit to you. But trust me, theyโ€™re as real, and as meaningful as they get.

When she doesnโ€™t complain at all and just disappears from your life, she didnโ€™t feel safe with you to give you the feedback you ought to hear. She feared your reaction, or at least the expectation of your reaction. You never provided the safe space she needed. Itโ€™s likely because of how you talked about others. The more judgmental you are about others, the more sheโ€™ll thinkโ€ฆ if things go awry, will you say the same about me behind my back? Can you even handle any amount of criticism?

Thereโ€™s another great line on communication, but also on relationships by writer and poet Khalil Gibran. โ€œBetween what is said and not meant, and what is meant and not said, most of love is lost.โ€

If thereโ€™s one takeaway you need from this post, whether youโ€™re a LP, there is more love (and reputation) lost in the lack of communication than in overcommunicating.

Photo by Scott Umstattd 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.

On spinouts

When British voters voted for Brexit in 2016, comedian James Acaster gave a hilarious and apt analogy.

When you make tea, “if you leave the [tea] bag in, and over time, the cup of tea itself as a whole gets stronger. And it might appear like the bag is getting weaker but it’s now part of a stronger cup of tea. Whereas if you take the bag out, the tea is now quite weak, and the bag itself goes directly in the bin.”

I think that’s the case with a lot of spinouts. Not all. But a lot.


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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.

GP EQ

conversation, eq, fundraising

A conversation with an LP reminded me of this recently. Can we trust a GP’s word that they’re a good picker if they can’t assess how likely an LP is to commit?

I’ve had multiple conversations with GPs where they tell me XXX and YYY are excited to come in the fund, and they just need more time to close their fundraise or for their process. Then the same XXX and YYY LPs ghost these GPs for months on end. For me, that’s enough for me to question their level of commitment, but not having been in those conversations firsthand, I can’t speak to the actual incentives. Sometimes, I actually know XXX and YYY LPs well enough to pick up the phone and dial them right away and ask them what’s up. Which I do. Only to hear from them and they say they had passed already.

Now I don’t know what actually goes on between those two parties. What’s said and what’s not said. There are many LPs out there who give very soft “no’s.” In hopes to not offend, they imply it’s a “no.” There are also LPs who explicitly say it’s a “yes” ONLY IF ZZZ happens. Given the current market, most of the time, ZZZ doesn’t happen, which becomes an easy out for the LP. The LP’s felt like they’ve delivered the “no.” The GP is still hanging onto the hope the LP likes them enough to break the rule. And then, there are many GPs who have selective hearing loss.

Nevertheless, there are multiple instances of this. And it’s not my job to point fingers to any party other than elucidate that this exists in our world.

That said, even if an LP doesn’t explicitly say “no”, there should be enough breadcrumbs to point to whether someone is a pass. Probably harder to know if they’re a “yes.” But there’s definitely writing on the walls if it’s a pass. And it’s almost always better to assume an LP is an out than an in if there’s hesitation.

The outstanding question for someone like me or any of my friends who I’ve had this conversation with is… is this indicative of a GP’s EQ when talking to founders? Is this GP more prone to rewriting history and facts? Is there a massive perception bias here and is the GP living through rose-tinted lens?

Richard Feynman has this great line. “The first principle is that you must not fool yourself โ€” and you are the easiest person to fool.”

And I’ve also had this conversation with another GPs a few weeks back, and I said, “You’re either lying to me or you’re lying to yourself. One is worse than the other. But neither gives me a reason to back you.”

Photo by Priscilla Du Preez ๐Ÿ‡จ๐Ÿ‡ฆ 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.

Whac-A-Mole

One of the questions that seem to come up every so often, whether it’s when I’m on a podcast or a fireside chat or just in conversation, is: Between sourcing, picking, and winning, which one do you think is the most important that emerging managers have?

The cop-out answer is always: They need all three. Or, they’re all important. Which is theoretically true. One in isolation is really hard to pull off ’cause then you need to account for sheer dumb luck (hope is never a strategy). And while everyone is subject to their own answer, I’m a big believer that the lead domino between the trifecta is sourcing. If you never see it, how do you even pick or win it?

We can talk about how you’d theoretically and systematically pick the best founders or how your value-add is something that is something truly valuable to your investments, but if you never have the opportunity to interact with a generational founder, I don’t care how smart you are. Or how well-connected you are. Or how experienced you are. I don’t care if you’re the world’s greatest X if no one’s heard of you or thinks of you when they or someone close to them starts a company.

Venture is a game of outliers. (I feel like a broken record at this point writing and saying this.) And I would much rather a GP see and miss generational founders again and again (and well, learn each time they do) than to have only seen one their entire life. Obviously, both are better than not having met any ever. You don’t know what quality looks like if you’ve never seen quality before they became obvious. No amount of books you’ve read or podcasts you’ve listened to will help you with that. I would rather you have a large anti-portfolio than build one for the first time as you’re starting your first fund. And in that anti-portfolio, it’s a lot of “I didn’t pick it” or “I didn’t win it” or “I didn’t even know I wanted to be an investor yet.” Yet despite all of that, I’ve chosen to stay in touch with these generational talents and they still value my presence in their orbit.

If you’ve only met one generational founder in your life before, I need to figure out if your network and sourcing channels would allow you to see another in the next 3-4 years (or whatever your deployment period is). And that when you see it, you’ll know that that is the one. But every generational founder looks different from the rest. So if you’ve only seen one in the past, how will I know if you have both the pattern recognition and the exception recognition to pick the next?

For those who have seen one or less generational founders in their lives, I have to bet that you somehow can “use the Force.”

That on the off-chance you do find one, can I trust your intuition to recognize it AND win it?

On the flip side, there’s this game that many of us grew up with. Whac-A-Mole. It’s an arcade game that has a series of moles hiding in holes. The goal is to whack as many moles as you can as they pop their heads up. Venture investing is similar. Each mole is a generational founder. That you may miss “whacking” many a generational founder, but as long as you keep seeing them, and as long as you keep trying to pick them, you’ll eventually hit one. And if you’re lucky, more than one. But in order to see multiple generational founders, you need the cards to be stacked in your favor. The ideal venture manager should be playing a constant game of Whac-A-Mole, as opposed to using the force. Although, damn, being a Luke Skywalker sounds a hell of a lot cooler than playing an arcade game.

To pull a line from Scale’s Rory O’Driscoll that I wrote about in a previous post, “Having to deal with the psychological burden of having an anti-portfolio is a privilege. If you never have the psychological tax of passing on multiple generational deals, you shouldnโ€™t be in venture. Passing on 20 great companies out of 40 great companies you see is always more preferable than investing in 2 great companies after seeing 40 average companies.”

Then there’s the question of whether our definition of generational founders even match up. Does your definition lead you to find founders who will exit at $1B+ outcomes? $100B+ outcomes? Or $100M outcomes? But a topic for another day.

Photo by Yuheng Ouyang 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.

What is the Density of your Founder NPS? | El Pack w/ Charlotte Zhang | Superclusters

charlotte zhang

โ€œWeโ€™re going into a world where there will be an increase in inequality in terms of the haveโ€™s versus have-notโ€™s. And so if you are invested in some of the haveโ€™s, I would actually bet on their acceleration of value aggregation in the later stages of scaling which is why I, personally, think a winning strategy is to hold onto them for as long as possible.โ€ โ€” Charlotte Zhang

Charlotte Zhang from Inatai Foundation is back! And if you’ve tuned into her first episode on Superclusters, you’ll know exactly why. Charlotte has been one of my favorite guests on the podcast, marrying both her profound ability for deep analysis with strong framework-oriented assessments. You might remember her 4 P’s to underwriting every manager from our prior episode.

Naturally I had to have her back for an El Pack episode to answer your questions on how to build a venture capital fund. We bring on 3 GPs at VC funds to ask 3 different questions.

99VC’s Lisa Yu asks about what LPs look for in Fund I’s beyond track record.

Escape Velocity’s Mahesh Ramakrishnan asks about recycling and what happens when you have 30% of your fund size as distributions in the first few years of the fund.

Founder Embassy’s Helena Gagern asks about investing in AI frontier labs where the first round of financing already puts the company at $400M+ in valuation. And also, how do you communicate to LPs that you have an “exceptionalism” bucket to invest out of?

As the director of investments at Inatai Foundation, Charlotte Zhang oversees the selection of external investment managers, conducts portfolio research, and helps to institutionalize processes, tools, and resources. She previously served as a senior associate at ICONIQ Capital and, before that, Medley Partners. When not working, you can find her globetrotting (18 countries and counting), writing a Yelp review about the best bite in town, or cuddling up with a book and her two adorable cats.

You can find Charlotte on her LinkedIn here:
LinkedIn: https://www.linkedin.com/in/charlotterzhang/

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

OUTLINE:

(00:00) Intro
(01:04) What’s new in Charlotte’s life?
(04:06) LPs Charlotte would love to meet
(05:41) Who is Lisa and 99VC?
(09:31) What qualities does Charlotte look for beyond track record?
(14:55) How does a GP know if they have a differentiated strategy?
(15:49) Charlotte’s pet peeve
(17:29) The bottoms up exercise of building a fund strategy
(18:00) Consistency of execution
(20:05) The highest level of signal you can get from a founder reference
(22:18) The ask
(22:51) Who is better at bowling: Mahesh or David?
(24:44) Who is Mahesh and Escape Velocity?
(25:20) Why is Escape Velocity spelled as EV^3?
(27:10) What happens when you have 30% DPI in the first 2 years of your fund?
(30:19) Does early DPI matter more in Fund I than Fund III?
(33:26) Should you sell secondaries at the Series B as a pre-seed/seed GP?
(37:34) Venture is under siege for no DPI
(38:18) Would Charlotte rather have 4X in 10 years or 7X in 15 years?
(39:42) Have’s and have-not’s
(40:35) Who is Helena and Founder Embassy?
(44:45) What is Charlotte’s reaction when a pre-seed GP invests in a $400M post valuation?
(49:23) How do the best GPs communicate betting off-thesis?
(50:44) How many GPs have an “exceptionalism” bucket to invest out of?
(55:56) How much underwriting goes into a GP breaking the rules?
(58:10) “A-players are obvious” but what isn’t?
(1:00:38) Charlotte’s last piece of advice for LPs
(1:03:43) Charlotte’s last piece of advice for GPs
(1:07:18) Why you should talk about the anti-portfolio
(1:09:33) David’s favorite moment from Charlotte’s previous episode

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œIn venture capital, although the top quartile of emerging managers outperforms the established funds. On average, you would actually be better off investing in established funds than in an emerging manager because the dispersion of returns is so much wider in emerging managers.โ€ โ€” Charlotte Zhang

โ€œBecause incumbent brands create access flywheels, the most important thing for an emerging manager is having a clearly differentiated strategy. Otherwise, itโ€™s fighting an unwinnable war.โ€ โ€” Charlotte Zhang

โ€œInvestment strategies are simply financial products serving the market of what founders and management teams in businesses need.โ€ โ€” Charlotte Zhang

โ€œThe best founders will know who the best VCs are.โ€ โ€” Charlotte Zhang

โ€œItโ€™s all about the density of the NPS you have amongst the best talent. Of course, if they have a good experience with you, theyโ€™re more likely to refer others they think highly of to you. And thatโ€™s the reason why it becomes a leading indicator and therefore, a self-fulfilling prophecy as to who rises to the top.โ€ โ€” Charlotte Zhang

โ€œItโ€™s actually a higher signal to me if itโ€™s someone referring you that didnโ€™t take money from you.โ€ โ€” Charlotte Zhang

โ€œWhen weโ€™re conducting diligence as an LP, you should be looking under the rocks where you are more likely to find disproving evidence.โ€ โ€” Charlotte Zhang

โ€œIf [venture] does not produce any realized returns, how will it be self-funding? And how can you continue pacing sustainably into this asset class?โ€ โ€” Charlotte Zhang

โ€œWeโ€™re going into a world where there will be an increase in inequality in terms of the haveโ€™s versus have-notโ€™s. And so if you are invested in some of the haveโ€™s, I would actually bet on their acceleration of value aggregation in the later stages of scaling which is why I, personally, think a winning strategy is to hold onto them for as long as possible.โ€ โ€” Charlotte Zhang


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
For Superclusters After Hours: โ https://superclusterslp.substack.com/โ 
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP


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.

12 Types of LPs

I just shared this verbally on a podcast and a talk recently, and realized while I’ve shared this friends, I’ve never shared it publicly explicitly or made a graphic for it.

What is it? And this was helpful when I was in IR, but also hopefully helpful as a GP pitching LPs, what are the types of LPs that exist?

I never really liked the line, “If you know one family office, you only know one.” Or if you know 1 LP, you only know one.” Probably true in a lot of circumstances, but feels odd that there are 100,000+ types of family offices or LPs.

Short blogpost, but I’ll probably elaborate on each in a future one, but sometimes a picture speaks a thousand words.

This is not all-inclusive, just like Myers-Briggs or OCEAN/Big 5 or the enneagram isn’t. But hopefully a good orienting framework in the first few meetings with LPs.

I borrowed a little bit of the nomenclature my buddy Matt Curtolo used as my original segmentation of LP archetypes was not as well-worded.

X-axis is if they own / create the wealth or not. Y-axis is Maslow’s Hierarchy of Needs.

P.S. This is not a framework you brag about to your LPs. You don’t tell any LPs how they’re bucketed. Just like you as the GP don’t like to get bucketed, no LP wants to. But in this case, when fundraising, you need to eat your ego.

P.P.S. Honestly, you should probably eat your ego while investing, but no one usually listens to this latter comment.


    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.

    Who Should NEVER Start a VC Fund? | Sam Huleatt | Superclusters | S7E3

    sam huleatt

    โ€œLower barriers to entry doesnโ€™t mean higher probabilities of success.โ€ โ€” Sam Huleatt

    Sam Huleatt is the co-founder of The Side Letter, a platform driving network-based research for capital allocators. Prior to The Side Letter, he created and ran the The LP Institute at VC Lab, as well as let On Deck Angels at On Deck. Moreover, he’s a serial founder, active angel investor in over 35 companies, and an active allocator in emerging fund managers, including the likes of Notation Capital, Orange Fund, Inuka Capital, Asylum Capital, and more.

    You can find Sam on his socials here:
    LinkedIn: https://www.linkedin.com/in/samhuleatt/
    X / Twitter: https://x.com/samhuleatt

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

    OUTLINE:

    [00:00] Intro
    [01:34] Sam’s childhood
    [03:24] The most persistent myth about Sam he never bothered to correct
    [05:47] Bottom-up vs top-down investor
    [13:37] Can career VCs develop empathy for the founder?
    [18:43] Traits of someone who should definitely start a fund
    [26:45] Traits of someone who should NEVER start a fund
    [28:09] Air of inevitability
    [33:44] Why was Outlander VC inevitable?
    [36:11] Where should 60% of your Fund I capital come from?
    [41:47] Starting a VC fund is hard
    [44:46] Do LPs like GP accelerators?
    [51:35] Top 3 considerations for first-time LPs
    [58:03] How many GPs should 1st-time LPs meet?
    [1:01:06] Governing law of VC: Adverse selection
    [1:04:40] Incentive alignment on fees
    [1:06:36] Terms in LPAs vs side letters
    [1:11:16] What is The Side Letter?

    SELECT LINKS FROM THIS EPISODE:

    SELECT QUOTES FROM THIS EPISODE:

    โ€œA career VC has a lot more experience having been on boards. And because of that, because theyโ€™ve been a career VC, theyโ€™ve seen more companies operating at scale and the issues that come into play in those cases, whereas operators-turned-GPs often have a narrow aperture because theyโ€™ve spent most of their career at one or two companies. On the one hand, the operator-GP obviously has a lot of empathy for founders because theyโ€™ve been that founder, but they probably havenโ€™t experienced all of the difficult issues that come up as companies scale across lots of different environments. Career VCs have.โ€ โ€” Sam Huleatt

    โ€œThe best investors have an air of inevitability. Itโ€™s not asking for permission or doing something because itโ€™s perceived to be high status.โ€ โ€” Sam Huleatt

    โ€œLower barriers to entry doesnโ€™t mean higher probabilities of success.โ€ โ€” Sam Huleatt

    โ€œMost people, after starting a fund, should assume that 60% of that Fund Iโ€”you should raise that from first-degree connectionsโ€”people you already know. It may not be easy, but if you donโ€™t have a network thatโ€™s large enough or has those resources, you either need to reconsider your fund target size or maybe you need to spend more time building your network before you start to go out and do that raise.โ€ โ€” Sam Huleatt

    โ€œIf you donโ€™t have an edge going into [a GP] accelerator, youโ€™re certainly not going to find an edge in the accelerator.โ€ โ€” Sam Huleatt

    โ€œWhy do the best GPs in the world want you to be on the cap table? A lot of people forget that a key aspect of venture is not just picking, but being picked. Thatโ€™s true for LPs and itโ€™s true for GPs.โ€ โ€” Sam Huleatt

    If you somehow made it to the bottom of these show notes, I’m also trying a new experiment where I write my reactions to the episode on my second blog, Superclusters After Hours. For Sam’s episode, you can find my reactions here.


    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.

    “I Write-Off Every Sourcing Slide” | Alex Felman | Superclusters | S7E2

    alex felman

    โ€œThe game you play as youโ€™re building a reputation becomes a different game than when you have a reputation. And I tend to find, from an LPโ€™s perspective, when youโ€™re building reputation, thatโ€™s actually when you deliver the most value.โ€ โ€” Alex Felman

    Alex Felman is an entrepreneurial and family office professional. For over 10 years, as a second-generation member, he has run his own family office, Felman Family Office, and works with family offices around the world through his family’s multifamily group, MSF Capital Advisors. Using his expertise in Molecular Toxicology and Bio-entrepreneurship (B.A from University of California -Berkeley, MBA from Copenhagen Business School), he advises them in biotechnology, healthcare, and other futuristic tech industries with the goal of maintaining long-term wealth through innovation. He regularly speaks at family office and private wealth events on topics such as tech investment, manager selection, generation and succession issues, rising generation trends, and more.

    He has used his experience within the family office industry and 20 year background as an educator to create Exponential U, a family office education program designed to help families become multigenerationally sustainable. His proprietary L3 framework (Learn, Leverage, Legacy) allows the holistic development of family members to ensure a smooth leadership transition.

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

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

    OUTLINE:

    [00:00] Intro
    [04:36] The ‘tastemaker’ for family offices
    [05:54] Exploration vs discipline
    [08:15] The hero’s journey in investing
    [09:49] The life line
    [13:39] Building and having reputation
    [16:06] Risk appetites for asset owners & allocators
    [18:44] Why won’t an institution invest in me?
    [19:50] The quiet thing LPs don’t talk about
    [25:15] When did Alex get involved with his family office?
    [29:09] Writing off sourcing slides
    [35:33] Different flavors of “sourcing from YC”
    [38:41] Emerging GPs are “investments-as-a-service”
    [40:08] Fund power law is greater than startups’
    [43:44] Emotional value of investing in funds
    [44:45] Most VC funds are scams!
    [50:01] Optimistic cynic
    [51:43] Reminders today about the good ol’ days
    [54:17] Late stage capitalism
    [59:10] Post-credit scene: Dave Chappelle and podcasts

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    SELECT QUOTES FROM THIS EPISODE:

    โ€œEvery great conversation dances on the line of your understanding. You dance between both sides of the line and try to find out where what you know and what they know intersect and end. Good conversation is like play.โ€ โ€” Alex Felman

    โ€œWith my background from the family offices, I almost believe that most family offices moving forward will need their own personal tastemaker or sommelier. Someone whoโ€™s curating the world specifically for the needs of that family.โ€ โ€” Alex Felman

    โ€œPeople get into trouble when theyโ€™re using the wrong tool or trying to do something for a different purpose. For example, Iโ€™m going to try to do discovery when Iโ€™m in my routine. Ok, youโ€™re probably running into problems. Or routinizing my discovery. Those two things are in conflict with each other.โ€ โ€” Alex Felman

    โ€œOne of the things people always forgetโ€”… What they remember from the heroโ€™s journey is adventure, and we fight the dragon, and we get the treasure. But at the end of the heroโ€™s journey, youโ€™re supposed to bring that back to your community. And youโ€™re supposed to forward it to your community. And youโ€™re supposed to make your community better from the dragons and the treasure that you fight or find. Most people often leave off that last part. And I actually think that last part is extremely important.โ€ โ€” Alex Felman

    โ€œThe game you play as youโ€™re building a reputation becomes a different game than when you have a reputation. And I tend to find, from an LPโ€™s perspective, when youโ€™re building reputation, thatโ€™s actually when you deliver the most value.โ€ โ€” Alex Felman

    โ€œIf you have a family office where youโ€™ve actually outsourced it, your employee is more of an allocator than an owner. And in that case, that allocator is often making decisions to save their own job. Or to ensure that they continue to have a job.โ€ โ€” Alex Felman

    โ€œWhat I find is slightly sad is that ultimately because of security and comfort reasons, things like peopleโ€™s pensions which should be more secure, are actually, in my opinion, taking riskier bets. And bets that will lead to worse outcomes.โ€ โ€” Alex Felman

    โ€œI believe that the amount of due diligence you do doesnโ€™t matter depending on the deal size. So letโ€™s say theyโ€™re writing five $100 million checks compared to 100 $5 million checks, that is literally 20 times the amount of work. So even if theyโ€™ll get a better return on that 100 $5 [million checks], on a realistic level, it forces them to play certain types of games.โ€ โ€” Alex Felman

    โ€œWith at least funds on a standard two and twenty, somewhere around $75-100 million fund size is where the incentives shift from being carry-oriented to management-fee oriented. Once you get larger than that, then it actually becomes more incentivized for the fund managers to build up their funds than the actual returns itself.โ€ โ€” Alex Felman

    โ€œI would argue that power laws apply even more to funds than to startups.โ€ โ€” Alex Felman

    โ€œThe intersection of venture as a product or service meets venture as a job career. And there are a lot of fund managers who see venture as a job career and essentially want to use it as a way to get a paycheck. And because of that, theyโ€™re going to put out a fairly boilerplate fund.โ€ โ€” Alex Felman

    โ€œMany venture funds are basically scams. I believe itโ€™s a scam if you knowingly sell something you know you canโ€™t deliver on. And the dirty secret in venture is if you purely look at venture from a financial point of view, most fund managers know they cannot hit their targets and yet they still sell that promise anyway. And I think that starts to become kind of scammy.โ€ โ€” Alex Felman

    If you somehow made it to the bottom of these show notes, I’m also trying a new experiment where I write my reactions to the episode on my second blog, Superclusters After Hours. For Alex’s episode, you can find my reactions here.


    Follow David Zhou for more Superclusters content:
    For podcast show notes: https://cupofzhou.com/superclusters
    Follow David Zhou’s blog: https://cupofzhou.com
    Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
    Follow Superclusters on TikTok: https://www.tiktok.com/@super.clusters
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    Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


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

    (Not) Relationship Advice

    relationships, biking

    Earlier this year, when catching up with a friend and talking about love, he shared his greatest relationship advice. “You want to marry someone who believes the world happens because of them, not to them.” And it really stuck with me. Both he and I are people who have big dreams. That in order to make our dreams happen we need every oar rowing in the same direction. That includes the people we surround ourselves with. More than anyone else, our romantic partner is likely the one we spend the MOST time with. But that in itself is a slight digression.

    In a somewhat parallel sequence of events, at the end of last year, I had the opportunity to join a much, much larger shop. And while I ended up choosing not to join, the primary question I was asking myself was: If I were successful here, would I be successful in spite or because of the institution? The truth was from an outsider’s perspective, maybe even personally, it’d be really hard to tell.

    Now why do I share the above? And where the hell am I going with all of this? What does love have to do with career opportunities?

    So… this won’t be my most graceful transition between thoughts, but in my head, they all orbit the same genre.

    One of the questions I used to ask LPs during my time in investor relations was: “What was the last investment you made that didn’t work out? Without naming names, what happened?”

    And there are two reasons I ask that:

    1. Oftentimes, knowing what an LP doesn’t or won’t ever invest in again is more telling than asking them what they do invest in. LPs are, by definition, generalist. And under that premise, they technically invest in “everything,” so you’ll end up getting very broad answers, especially if they cover more than one asset class.
    2. Do they describe an investment that didn’t work out with active or passive verbs? Did it happen to them? Or do they own up/exhibit agency over their own decisions? Are they arbiters of their own destiny? “I made this investment decision, learned, and this is what I won’t do in the future. Or will still continue to do.” is different from… “This mishap happened to me. How could I have known? It is what it is. It’s not my fault. It was out of my control. It was someone else’s decision.”

    For the latter point, people who don’t seem to be able to own up to the decision will likely not be your greatest champions if you’re an emerging manager. If at all. To them, life happens to them. They can’t control it. They have a narrative they keep telling themselves that they have no power. Some might be true. But these folks rarely stick their neck out for you.

    By default, most emerging managers look less than pretty. A million reasons (most of which likely true) of what could go wrong. And it’s actually in the best interest of a capital allocator’s career and income that they stick their neck out for risky bets. Many institutions don’t compensate their team based on outlier performance. So incentives won’t be aligned. But to borrow an adage of Jobs, “the people who are crazy enough to think they can change the world, are the ones who do.” And at the very minimum, they have to believe they can change their own world.

    When things are non-obviousโ€”from a returns perspective or strategy or anything elseโ€”you need people who can and will invest courageously and own that decision.

    Photo by Everton Vila 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.

    “Venture is a Who Business, Not a What Business” | JD Montgomery | Superclusters | S7E1

    jd montgomery

    โ€œOne thing that is unique to private equity and venture capital is persistence is a little easier because of the brand. โ€˜They did good deals, so therefore, the good deals come to find you.โ€™ If you were in a long-only private equity shop or hedge fund, Amazon is not going to come find you because you invested in Shopify.โ€ โ€” JD Montgomery

    JD Montgomery leads the Family Office division at Canterbury Consulting and is a seasoned advisor with nearly four decades of experience serving prominent families with a focus on strategy, organization and measurement. Based in Newport Beach, he serves a select group of multi-generational families and helps them navigate the complexities of wealth, purpose, and legacy. Mr. Montgomery partners with his clients to help them optimize the allocation of their resources across generations. Over the years, Mr. Montgomery has developed a deep network of relationships in the venture capital industry. He has helped his clients gain meaningful exposure to venture funds and direct investments and develop relationships with leading innovators and investors globally. He is a Managing Director, shareholder, and board member at Canterbury Consulting. He graduated from Stanford University and holds the Chartered Alternative Investment Analyst (CAIA) designation.

    You can find JD on his socials here:

    LinkedIn: โ https://www.linkedin.com/in/jd-montgomery-6161341b/โ 

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

    OUTLINE:

    [00:00] Intro
    [02:18] The “some day” exercise
    [11:12] Why does JD do “some day” every 6 months?
    [12:33] JD’s life line
    [16:44] When JD is 85 years old…
    [18:05] JD’s relationship with fatherhood despite the trauma
    [22:40] Annual dad report cards
    [25:33] Intentionality with GPs
    [28:41] How to avoid one-hit wonders
    [33:43] How to transfer self-esteem
    [36:05] How do you get GPs off of their talk track?
    [37:36] Non-obvious things JD looks for in GPs
    [41:43] Is selling 0.2X DPI in the first 4 years meaningful?
    [44:27] Should you recycle capital or deploy out of the next fund?
    [46:34] Why did JD choose to work with families?
    [48:07] “Never eat alone”
    [51:34] How does JD think about time allocation?
    [55:06] How many new GPs does JD meet with?
    [59:07] How did JD pass on then back Founders Fund?
    [1:03:22] The difference between unexplored gold veins and rotting trash
    [1:08:13] Mayan Mocha at Austin’s Picnik
    [1:08:58] JD’s secret street taco recipe
    [1:11:09] JD’s reminder that we’re still in the good ol’ days
    [1:13:20] Post-credit scene: No garlic and onions

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    โ€œI donโ€™t have a mentor per se. My mentor is hundreds, probably thousands of peopleโ€”Iโ€™m sure thousandsโ€”people that Iโ€™ve met where I try to learn just the amazing talent that person has and I smush it with the next person that I meet that might be most kind person that I meet or the most organized. So itโ€™s this blend of a lot of people that really becomes the mentor.โ€ โ€” JD Montgomery

    โ€œDOD โ€“ dear old dad.โ€ โ€” JD Montgomery

    โ€œKids grow up like trees and saplings. And a sapling needs a guiding post to hold them up when itโ€™s windy.โ€ โ€” JD Montgomery

    โ€œOne of the other questions I will ask is: โ€˜Tell me about the hardest thing youโ€™ve ever done in your life.โ€ โ€” JD Montgomery

    โ€œTo whom much is given, much is expected.โ€ โ€” JD Montgomery

    โ€œIn estate planning, you can transfer money, but you canโ€™t transfer self-esteem. Self-esteem is gained by going through the school of hard knocks and doing things and relying on yourself.โ€ โ€” JD Montgomery

    โ€œOne thing that is unique to private equity and venture capital is persistence is a little easier because of the brand. โ€˜They did good deals, so therefore, the good deals come to find you.โ€™ If you were in a long-only private equity shop or hedge fund, Amazon is not going to come find you because you invested in Shopify.โ€ โ€” JD Montgomery

    โ€œIf theyโ€™re passionate about somethingโ€”if they want to leave the world just a little differentโ€”their ding in the universeโ€”and they want to give back, money doesnโ€™t ruin them.โ€ โ€” JD Montgomery quoting a North Carolina professor

    โ€œI am not in a โ€˜whatโ€™ business; Iโ€™m in a โ€˜whoโ€™ business.โ€ โ€” JD Montgomery

    โ€œGross IRR; gross performance. I donโ€™t care. I care about net. Itโ€™s okay to show gross and then net. I prefer net. But if you show gross only, itโ€™s just gross.โ€ โ€” JD Montgomery

    If you somehow made it to the bottom of these show notes, I’m also trying a new experiment where I write my reactions to the episode on my second blog, Superclusters After Hours. For JD’s episode, you can find my reactions here.


    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.