Gratitude and Deal Flow

thank you, gratitude

A few months ago, my good friend Sam hosted a happy hour for LPs, which he invited me to. There I caught up with a former fund-of-funds (FoF) manager who has booked some of the most impressive returns I’ve ever heard of for a pure FoF play. For context, more than one fund generated over 15X net distributions to their LPs. The numbers were enough to impress me. But I had to ask: “Across all the funds you were a part of, what is something that you look for that you’re reasonably confident others don’t?”

He said two things, but one stood out. “Gratitude. I look for managers who never forget who put them in business.”

In all honesty, I found that odd. Not because I disagreed. I love folks who recognize and are grateful to the people who got them to where they are today. But because it didn’t occur to me that it should be the top two things one should optimize for when picking managers. Naturally, it kept gnawing at me.

In my own experience, gratitude seems to compound. Grateful individuals thank you often and sometimes when you least expect it, and more often than not, assuming you’ve done real work to help them, they compliment behind your back. The people they talk to end up learning about you. Their teammates learn about you. And you’ve earned multiple occasions to meet their teammates and those close to them. When a GP or founder’s teammates leave and start new things, those people often think to call you first.

Grateful GPs often hire talent who are just as humble, and in turn, as second nature, extend their appreciation often. Those same GPs are more likely to invest in people who have similar traits as well. So, it begins this flywheel.

As an LP, I look for emerging GPs whose network and deal flow compounds over time. That the first moment I meet them is the smallest network they will ever have again. So I expect and underwrite a GP’s ability to compound deal flow over time. So Fund n+1 is better than Fund n, and Fund n+2 is exponentially better than Fund n. Gratitude is one way GPs can increase the surface area for serendipity to stick. For there to be more quality inbound opportunities in the future.

Photo by Jonny Gios on Unsplash


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


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

Why I Don’t Pay for LinkedIn Premium

ruler, short

“I didn’t have time to write a short letter, so I wrote a long one instead.” — Mark Twain

I write on this blog because I can write to think. I can write as a stream of consciousness. But at the same time, it is just that. It’s long.

But when it comes to reaching out and getting a stranger’s attention, there’s beauty in brevity. 200 characters. If you can’t get the attention of someone you don’t know in 200 characters. Hell, even 100 characters. Then no pitch deck, no long blurb ever will. Just because a house has more square footage doesn’t mean you’ll stop and visit the house.

People are busy. Investors are busy. Recruiters are busy. The world’s smartest, brightest, most ambitious are busy. A great cold message can go further than almost any warm intro can. Most people are just not good at writing them. They’re too verbose. (Caveat, a lot of my outreaches are too, but I highlight the 20 words they need to pay attention to in that email. And they may not all be in the same sentence.)

To be fair, LinkedIn Premium is really the Trojan Horse for this short piece. Keep exercising the cold outreach muscle.

I still do it every week. And so far, the response rates to ones I handcraft are better than what AI can write for me. The platform of outreach may vary. Question I always think about is where are the people I’m reaching out to spending a lot of attention, but there’s just that slight deficit of inbound information. Sometimes, it’s literally a messenger pigeon.

Photo by William Warby 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.

How to Increase Dialogue with your LPs | El Pack w/ Kelli Fontaine | Superclusters

kelli fontaine

Kelli Fontaine from Cendana Capital joins David on El Pack to answer your questions on how to build a venture capital fund. We bring on three GPs at VC funds to ask three different questions.

The Council’s Amber Illig asked what happens when a solo GP is incapacitated or passes away.

Oceans Ventures’ Steven Rosenblatt asked why most LPs follow the decision-making of other LPs.

NeuCo Academy’s Jonathan Ting asked what LPs think about GPs asking for help.

From investing in great fund managers to data to investor relations, Kelli Fontaine is a partner at Cendana Capital, a fund of funds who’s solely focused on the best pre-seed and seed funds with over 2 billion under management and includes the likes of Forerunner, Founder Collective, Lerer Hippeau, Uncork, Susa Ventures and more. Kelli comes from the world of data, and has been a founder, marketing expert, and an advisor to founders since 2010.

You can find Kelli on her socials here:
X/Twitter: https://x.com/kells_bells
LinkedIn: https://www.linkedin.com/in/kellitrent/

And huge thanks to Amber, Steven, and Jonathan for joining us on the show!

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

OUTLINE:

[00:00] Intro
[01:26] Kelli’s new data discoveries
[04:32] How did Kelli underwrite a manager with no LinkedIn?
[06:19] Is too much data ever a problem?
[08:18] Vintage year benchmarking
[09:49] Telltale signs on GPs’ social profiles
[10:57] Data Kelli wishes she could collect
[15:59] Enter Amber and her new podcast
[18:08] Amber’s background and The Council
[19:08] How does Amber define top companies?
[24:25] How can a solo GP set the firm up well in case they’re no longer there?
[26:11] Kelli’s number one fear with solo GPs
[28:30] Best practices for generational transfers
[32:28] Solo GPs and their future plans
[36:51] Enter Steven and Oceans
[42:38] Would Kelli ever include AI summaries as part of the get-to-know-someone phase?
[44:18] Why do LPs follow other LP’s decision-making?
[48:43] What are the traits of an LP who is likely to have independent thinking?
[51:16] Why don’t LPs talk directly with founders?
[57:59] Enter Jonathan and NeuCo Academy
[1:00:05] Is Kelli seeing more secondaries firms?
[1:01:56] How often should GPs lean on LPs for help?
[1:07:22] Are most LPs helpful?
[1:12:21] What kinds of questions does Kelli get from her own GPs?
[1:15:39] Kelli’s last piece of advice

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“If that fund deployed over a year versus a manager of ours that deployed over four years, they’re going to look very different. So we do vintage-year benchmarking to see how their MOIC stacks up against how the revenue of companies stack up.” – Kelli Fontaine

“Team risk is the biggest risk in venture.” – Kelli Fontaine

“The same top ten firms are not the same that they were 15 years ago, and probably Silicon Valley. Generational transfer is very hard.” – Kelli Fontaine

“If you make the brand bigger than just you that it comes from DNA, support systems, things that you stand for that have had support to get there—so once that brand is made, the other team members embody that brand as well. That’s the way to do it. It’s really empowering other team members to own a part in that brand-building—outwardly and inwardly in decision-making.” – Kelli Fontaine


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.

Intro Policy

dogs, meet, intro

I used to send intro requests for as many people as I humanly could. Admittedly, a sillier, more naive me a long, long while back.

The most number of intro requests came from people I did not know. Usually founders. Given that I had just entered the venture world at that time, I was labeled as an investor or, at least, someone, who was connected to the investor world based on my LinkedIn. I also had a habit of adding anyone who reached out to connect (unless they were obviously spam). At the time, I thought, “What was the downside?”

Spoiler alert: There is a downside.

They would try to tell me about their startup. Then asked if I would invest. I’d say no, so they’d ask if I knew anyone who might be interested. A fair question. And a natural lead-in, had I offered any names, to: Can you intro me to them?

In trying to be a good Samaritan, I’d ask for the deck and blurb in a forwardable email. Half of them would. Half of them would say something to the effect of “You know enough about my company already; you write the email.”

And my dumbass, fearing to offend, would go out of my way to write intros for strangers who didn’t even bother to write anything themselves. So, I’d send that email to a friend or colleague in the industry. “You interested?” along with the email they sent me. And if they didn’t, just their LinkedIn, website, and/or deck.

Naturally, most would say no. Some would ask for my take on them. To which, I’d share that I didn’t know much about them outside of the obvious. I wasn’t investing myself, but they wanted to meet. 10-20% of the time, some friends and colleagues would say yes. (To this day, I wonder if it was just their policy to say yes to all warm intros or they were trying to be considerate of me. Some, over the years, I’ve asked. As such, it’s all the above.)

Over time, I would just include “I’m not investing. Only met them once.” in addition to “You interested?” in those emails.

Then one day, and I don’t remember when I first thought to myself, why the hell am I putting my reputation on the line each time for someone I don’t know and personally haven’t bothered to dig deeper only to write an email to show I also didn’t care about them? Why would I put myself through that? It had also become emotionally taxing to me to go through all those actions only to disappoint the founders (and myself) 99% of the time. Not only would I feel bad (often delayed disappointment and resent at myself), but I also wasn’t doing anyone any good.

So I stopped. Full stop. Period.

Around the early innings of the pandemic when it felt like there was a greater influx of deals and noise.

My rule became, and still is, unless:

  • I’m investing/invested
  • I’m advising (investing my time)
  • I’ve worked with you before and I would instantly jump at the chance to work together again
  • I’ve hired you
  • I’ve known you for so long and to a level we’ve become good friends and I feel like you’re a good reflection of the people I choose to surround myself with (that does not mean you have to be successful, but that you need to have good values and the discipline to pursue them)
  • You are someone I care about
  • Or someone, that has wowed me in a fundamental way.

AND I know the other person who you want an intro to well enough…

I’m not writing any intros.

I still read every email I get. Cold or not. And I still respond to every warm email I get. But for my fragile heart that can’t stand disappointing more people and the volume of emails I get, I’m not responding to any emails that look like they’re templated, AI-generated, or written without care. So I can focus on the ones that matter.

Photo by Collins Lesulie 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.

81% of America is Underfunded | Vijen Patel & Grady Buchanan | Superclusters | S5PSE1

vijen patel, grady buchanan

“19% of our GDP attracts about 55% of capital inflows, aka venture activity, and 81% is underinvested.” – Vijen Patel

We’re back with one of our crowd favorite formats, where we bring on one LP and one GP, and share why that LP invested in this GP. This time, we have Grady Buchanan, co-founder of NVNG, and Vijen Patel, founding partner of The 81 Collection.

Vijen Patel is an entrepreneur and investor. He founded The 81 Collection, a high growth equity firm in boring industries. Previously, he founded what is now known as Tide Cleaners. He bootstrapped what eventually became the largest dry cleaner in the country (1,200 locations) before selling to Procter & Gamble in 2018. Before Tide Cleaners, he worked in private equity, McKinsey & Company, and Goldman Sachs. He lives in Chicago with his wife and two kids.

You can find Vijen on his socials here:
LinkedIn: https://www.linkedin.com/in/vijenpatel/
X / Twitter: https://x.com/itsvijen

Grady Buchanan is an institutional and risk-based asset allocation professional with a passion for bringing venture capital to those who have the interest. He founded NVNG in late 2019 and oversees investment strategies, the firm’s venture fund pipeline, manager sourcing, due diligence, and external events. Before launching NVNG, Grady worked with the Wisconsin Alumni Research Foundation’s (WARF) $3B investment portfolio, focused on private equity and venture capital initiatives, including fund diligence, investment strategy, and policy. Grady is based in Milwaukee, WI.

You can find Grady on his socials here:
LinkedIn: https://www.linkedin.com/in/gradynvng/
X / Twitter: https://x.com/GradyBuchanan

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

OUTLINE:

[00:00] Intro
[02:41] The pressure of quitting a PE job for dry cleaning
[05:09] Vijen’s self talk as a founder
[06:50] How to overcome doubt
[09:00] How Vijen learned customer success
[10:35] What did Pressbox become?
[12:41] The dichotomy between society’s needs and what gets funded
[14:19] How did Grady go from selling pancakes to being an LP?
[23:51] Why did Grady think he bombed the LP interview?
[29:15] What is The 81 Collection?
[32:22] How did Vijen meet Grady?
[34:39] How is Vijen fluent in Spanish?
[36:40] How did Grady meet Vijen?
[42:21] How did Grady underwrite 81 Collection?
[44:44] What about Vijen made Grady hesitate?
[48:35] What’s one thing about 81 Collection that could’ve gone wrong?
[50:33] The 3 things that create alpha
[52:42] Why does NVNG have the coolest fund of funds’ names?
[53:47] The legacy Grady plans to leave behind
[56:06] The legacy Vijen plans to leave behind

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“I wrote down everyone’s concerns, and I just sat on it. A lot of the founders we like to work with, the ones who we really love are the ones who take it in and listen, write it down, then take some time to synthesize everything and then they’ll act with conviction. ‘Why is this stupid? Tell me why. Let’s go deeper and deeper.’ And oftentimes these reasons are very rational and slowly over time, what if I derisk this by doing that?” – Vijen Patel

“19% of our GDP attracts about 55% of capital inflows, aka venture activity, and 81% is underinvested.” – Vijen Patel

“There’s this crazy stat we recall often: the 50 richest families on Earth, who often build in this 81, they’ve held, on average, their business for 44 years.” – Vijen Patel

“We invest in only amazing managers; we will not invest in every amazing manager.” – Grady Buchanan

“Alpha’s three things: information asymmetry, access, and, actually, taxes.” – Vijen Patel


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.

On GP Commits

backflip, commit

1% GP commits have been a part of investing history for as long as most people can remember. But actually finds its origin as a vestigial part of IRS Revenue Procedures from 1974, more specifically Rev. Proc. 74-17, which stated “the interests of all the general partners, taken together in each material item of partnership income, gain, loss, deduction or credit is equal to at least one percent.”

And yes, technically, in 1989, Rev. Proc. 89-12 also created a lower bound of 0.2%. “In no event… may the general partners’ aggregate interest at any time in any material item be less than .2 percent.” But all of that was overturned in 2003.

Ever since then, the 1% GP commit has withstood the test of time.

But… I’ve always felt that to be a weird checkbox that LPs have for GPs. I get the element around incentive alignment. But why is incentive alignment a static number? If a college student is just starting a Fund I, still with student loans, and raising a $10M fund, $100K is a meaningful proportion of their net worth. Hell, they may not even have it. At the same time, a successful spinout who used to be a GP at a large established fund who’s received distributions already and raising $100M fund will likely have more than just $1M. And $1M alone is not a meaningful proportion of her/his net worth.

So, I think GP commits should be a function of a GP’s net worth, not the fund size.

I want to know that the GP is betting their career over on this next enterprise. I want to know that the GP is more motivated today than they were ever before. Even if they’ve already hit that career-defining success.

I’m looking for the fire under their belly. Why does this upcoming fund matter so much to them?

Personally, it’s not that I only choose to focus on Fund I’s and II’s. I’m open to the idea of other Roman numeral-ed funds, but I usually get the sense that the economics of commitment are misaligned with the intentions and motivations of the GP themselves.

Photo by Drew Farwell 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.

How Many Exceptions Are Too Many? | El Pack w/ John Felix | Superclusters

john felix

Pattern Ventures’ John Felix joins David on El Pack to answer your questions on how to build a venture capital fund. We bring on three GPs at VC funds to ask three different questions.

Atria Ventures’ Chris Leiter asked about the common mistakes LPs make when underwriting solo GPs.

Garuda Ventures’ Arpan Punyani asked how quickly do most LPs get to conviction. First 10 minutes? First meeting?

Geek Ventures’ Ihar Mahaniok asked how LPs evaluate Fund IIs when the Fund I has no distributions.

John Felix is a General Partner and Head of Research at Pattern Ventures, a specialized fund of funds focused on backing the best small venture managers. Prior to Pattern, John served as the Head of Emerging Managers at Allocate where he was an early employee and helped to launch Allocate’s emerging manager platform. Prior to joining Allocate, John worked at Bowdoin College’s Office of Investments, helping to invest the $2.8 billion endowment across all asset classes, focusing on venture capital. Prior to Bowdoin, John worked at Edgehill Endowment Partners, a $2 billion boutique OCIO. At Edgehill, John was responsible for building out the firm’s venture capital portfolio, sourcing and leading all venture fund commitments. John started his career at Washington University’s Investment Management Company as a member of the small investment team responsible for managing the university’s now $13 billion endowment. John graduated from Washington University in St. Louis with a BSBA in Finance and Entrepreneurship.

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

And huge thanks to Chris, Arpan, and Ihar for joining us on the show!

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

OUTLINE:

[00:00] Intro
[02:20] What’s changed for John since our last recording?
[04:08] What is Pattern Ventures?
[06:22] Why is Pattern’s cutoff for funds they’re interested in at $50M?
[07:32] How does John define noise?
[09:34] Do non-sexy industries require larger seed funds?
[11:36] How does think about overlap in the underlying startup portfolio?
[15:22] Enter Chris and Atria Ventures
[18:03] Should solo GPs scale past themselves?
[24:14] Partnerships have more risk than solo GPs
[26:10] How does John think about spinouts from large VC firms?
[27:53] The psychology of being a partner at a big firm versus your own
[30:38] Enter Arpan and Garuda Ventures
[31:26] Geoguessr
[32:52] Garuda’s podcast, Brick by Brick
[34:52] How quickly do LPs know they intuitively want to invest in a GP?
[38:02] The analogy to what GPs do to founders
[43:50] There are many ways to make money
[44:57] Quantifying intuition as an investor
[49:12] Enter Ihar and Geek Ventures
[49:36] How do LPs evaluate Fund IIs when Fund I has no DPI?
[53:01] How do you know if a GP did what they said they were going to do?
[54:47] What if the key value driver is off-thesis, but everything else is on-thesis?
[56:21] Is signing 1 uncapped SAFE per fund reasonable?
[57:14] What is the allowable percentage of exceptions in a fund?
[1:01:32] Good vs bad exceptions
[1:06:06] Reminders that we are in the good old days
[1:07:31] John’s last piece of advice to new allocators
[1:09:00] David’s favorite moment from John’s last episode

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“In life, it’s always easy to justify ‘why now’ is not the right time. I think it’s hard to justify ‘why now’ is the right time to do something.” – John Felix

“We love investing in things that are contrarian and non-consensus, but there has to be a path to becoming consensus because something can’t remain non-consensus forever. There has to be a catalyst that the market eventually realizes this or else the company’s not going to be able to raise venture capital. It’s not going to be able to sustain it and continue to grow and survive.” – John Felix

“The type of spinouts we want to back are the people who are successful in spite of working at the big brand, not because they worked at the big brand.” – John Felix

“You need to earn the right to start your new firm to do your own thing. I don’t think enough people realize that.” – John Felix


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.

How to Boost Engagement: Proven LP Relationship Building Techniques

A while back, my friend Augustine, CEO and founder of Digify, asked me to write something for his company, Digify’s blog, about how I think about maintaining relationships between fundraising cycles when I was still an investor relations professional. As such, I wrote a mini two-part series on the frameworks and tactics I use to maintain LP relationships. Been given the liberty to cross-post on this humble blog of mine, in hopes that it helps any emerging managers or IR professionals here.

Voila, two of two! The first one you can find here (also linked below).


Author’s note: My promise to you is that we’ll share advice you’ve likely never heard before. By the time you get to the end of this article, if you’re intimidated, then we’ll have done our job. Because that’s just how much it takes to fight in the same arena as people I’ve personally admired over the years and work to emulate and iterate daily. That said, this won’t be comprehensive, but a compilation of N of 1 practices that hopefully serve as tools in your toolkit. As such, we will be separating this piece into Part 1 and 2. The first of which is about overarching frameworks that govern how I think about managing relationships. The second of which focuses on tactical elements governed by the initial frameworks brought up.

You can find the first piece of two here.

It’s easy to stay high-level and strategic. I won’t. I personally find it helpful to have tactical examples on how to execute frameworks on LP relationship management. As your mileage may vary, the below will hopefully serve as tools for the toolkit, as opposed to Commandments or the Constitution for investor relations practices.

In general, people who help create a product have more mental and emotional buy-in to the continued success of said product. It’s why influencers leverage their fanbase to generate new ideas for content. It’s why laws and propositions are voted on. It’s why your parents asked what you wanted for dinner. It’s why, if you’re a junior team member and want budget and resources for your project, you ask for feedback from leadership (often). While not every LP wants to be intimately involved in the day-to-day, and even if they don’t end up helping, it still goes a long way when you ask for their feedback and advice for major firm decisions, regardless of whether they’re on the LPAC or not. Building strong LP relationships requires making them feel like true partners in the decision-making process. They want to be involved in:

  • Hiring/promoting a new partner or GP
  • Pivoting or expanding fund strategy
  • Increasing the length of the deployment period or fund term
  • Generating early DPI
  • Breaking a partnership

LPs want to hear news before they become news. And if time and expertise allows, they’d like to write the press release with you.

In addition, if you have the bandwidth and resources, host events with them on topic areas they’re interested in. Even if it’s a small gathering of four to six people, it’s the intentionality and the willingness that counts.

I think a lot about Ebbinghaus’ Forgetting Curve. Effectively, how long does it take someone to forget new information and as a function, how often do you need to remind someone for them to retain memory of that new piece of information? Within an hour, the average person forgets half of what they learned. Within 24 hours, the average person forgets 70% of it. And within a week, they forget 90%. I won’t get too technical here, but if you are interested in learning more, I highly recommend reading this paper: Murre and Dros’ Replication and Analysis of Ebbinghaus’ Forgetting Curve.

And so, in theory, every time someone’s memory of you, of your thesis, or of your firm drops below 90% memory retention, you should remind them. Rough intervals of which are within minutes, within 2 hours, within a day, within a week, within 30 days, and so on. In practice, after you catch up with an LP, text them a note saying that you’ll follow up within the day. And yes, texts are often far more effective in maintaining relationships with LPs than emails. Emails are read by other team members and often lost in inboxes. The only exception to this rule is if you or your LP is an RIA, and requires all communication to be archived, including text.

Outside of scheduled catchups, spend a lot of time tracking people’s hobbies and interests in your CRM, and sending LPs an article, video, interview or insight that reminded you of them or that you think they’d genuinely appreciate; it goes a long way. Oh, and sending thank you notes more often than you think you need to, especially unprompted ones, really helps cement relationships. Over time, this will become a habit. Here’s an example of an email I send often:

Hey [name],

Read this article [link article] this morning as I was grabbing my morning coffee and it reminded me of our conversation half a year back on [insert topic you were talking about].

One of my favorite lines from the piece was [insert quote from the article] – something I thought you would really get a kick out of.

I know you’re busy, so there’s no need to reply to this email, but I want to send this your way in case it’s interesting for you, as well as send you good vibes on this beautiful Tuesday.

Keep staying awesome,

David

Two things here:

  1. You do not have to write like me.
  2. Telling people that they don’t have to reply is more likely to result in a reply. Works for me 80-90% of the time when sending to a warm connection. Though, your mileage may vary.

When I had Felipe Valencia from Veronorte on my podcast, he mentioned that he brought Colombian coffee for GPs whenever he visited the States. I also know of IR people and GPs who do the same for LPs. And vice versa from LPs to Heads of IR and GPs, especially from our Asian counterparts, where gifting culture is more common. Do note though that if your LP is from a public institution—sovereign wealth fund, pension, endowment, or sometimes, even a large corporation—individuals are not allowed to accept gifts more than $50, or sometimes none at all.

One of my favorite lessons from Top Tier Capital’s co-founder, David York, was on when to see LPs as a function of budgetary cycles.

“Going to see accounts before budgets are set helps get your brand and your story in the mind of the budget setter. In the case of the US, budgets are set in January and July, depending on the fiscal year. In the case of Japan, budgets are set at the end of March, early April. To get into the budget for Tokyo, you gotta be working with the client in the fall to get them ready to do it for the next fiscal year. [For] Korea, the budgets are set in January, but they don’t really get executed until the first of April. So there’s time in there where you can work on those things. The same thing is true with Europe. A lot of budgets are mid-year. So you develop some understanding of patterns. You need to give yourself, for better or worse if you’re raising money, two to three years of relationship-building with clients.”

Knowing the timing of when to see who is important, especially these days when you’re required to meet and build relationships across the world. Strategic timing can make or break an LP relationship, particularly when it comes to securing allocations.

While the above are usually for pensions, corporates and sovereign wealth funds, endowments, foundations, and large family offices all have recurring cycles. And meeting a few months before the ball has to roll can mean the difference between you being a line item somewhere and being on top of the docket.

I first learned of this when tuning into a Reid Hoffman and Brian Chesky interview, which I highly recommend. It was further reinforced as I spent more time learning from people in the hospitality and culinary world.

To summarize, everyone knows what a 1- to 5-star experience looks and feels like. But when everyone is optimizing on a 5-point scale, to outcompete others, you must compete on a scale they have yet to conceptualize. And so a five out of five experience is one where you leave happy and content enough to leave a glowing review because all the boxes were checked. Everything in your ideal vacation, retreat, or dining experience was fulfilled. So… if that’s the new baseline, then what does a six out of five experience look like?

Maybe that’s sending a limo to pick someone up at the airport, so they don’t have to find their own way to the establishment. That could also be finding your guest’s favorite bottle of champagne and having it ready when they enter your premises.

So, if that’s a six out of five, what does a seven out of five look like? You’ve pre-booked everything your guest is interested in before they show up and without them having to lift a finger. Or you learned that on their entire NY trip, your diners never had the chance to try an original New York hot dog from a street vendor, so you replace one course of the menu just so that they can try it. (True story. Would highly recommend reading Will Guidara’s Unreasonable Hospitality.)

So, if that’s a seven-star experience, what does an eight look like? What about a nine-star? 10-star? 11-star?

At some point, the stakes get quite insane. Meeting their role model from the history books. Using time travel or teleportation devices. Meeting aliens. But trust me, if competitive sports taught me anything, it’s that it’s good to envision the impossible as possible. And, the most important part to envision in this entire exercise is the genuine, and unstoppable smile that appears.

So what does this look like in practice? I cannot list everything out there, because it’s 1. not possible, and 2. if I can spell out a true 7- or 8-star experience, it’s generalizable. And if it is, it won’t feel special. That said, let me list out some I’ve done in the past that hopefully serve as inspiration. Caveat, I’m a Bay Area native, and I still live in the Bay Area.

  • An LP tells me they’re coming to visit the Bay. I send them a suggested itinerary based on the number of days they’re here, which balances both work and some under-the-radar touristy things. On top of that, I send hotels I suggest, restaurants I recommend, and more. All of which I offer to call on their behalf because I know the staff there and I might be able to get them a discounted rate or an automatic upgrade.
  • If I recommend a restaurant, and they agree to host a meeting there or just to try it out, I call the restaurant, tell them that they’re really important people to me (can do so if I’m a regular patron there already), and on top of that, I ask them to give the guests a kitchen tour.
  • I ask a local chocolatier to custom make some bonbons for me that are inspired by the individuals visiting, that I give to the LPs when I meet them in person.
  • If it’s a rush order, I call one of the long-established fortune cookie shops in San Francisco for them to do a custom order and write custom fortunes inside each fortune cookie. And inside each fortune is a fun fact about each person I’ve introduced them to meet while they’re here.
  • When it comes to intros, 70% of my intros will be relevant to their business interests. Startups. VCs. Other LPs. 20% of my intros are my recommendation of who they should meet but might not know they should. 10% are 1-2 people I think extremely highly of who are outside of technology and startups, but will offer a fascinating perspective to the world. A YouTuber with millions of subscribers. A legendary restaurateur. A lead game designer. An author. A Nobel prize winning professor. Naturally, I do the last selectively. My job is also to protect their bandwidth. For the last set of intros, I also don’t take intro requests.

All-in-all, LPs, like the rest of us, are human. We’re emotional creatures. We love stories. We are naturally curious. We love wonder. Their job doesn’t always allow for them to be, especially with tons of back-to-back diligence meetings, conversations with stakeholders, and so on. So it makes me personally really happy when I can balance suspense and surprise when I help them craft trips to the Bay.

These are just a few strategies and tactics among many. The goal with this piece was never to be exhaustive, but to inspire possibilities and your favorite practices. And if you’re willing, I, as well as the Digify team, are always all ears about practices you’ve come to appreciate and build into your own routine. Until the next time, keep staying awesome!


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!


Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.

Uncompensated Risks in VC | Wendy Li | Superclusters | S5E12

wendy li

“It’s not the probability; it’s the consequence. It’s not the probability when something goes wrong. It’s the consequence when it goes wrong.” – Wendy Li

Wendy Li is the co-founder and Chief Investment Officer at Ivy Invest, a fintech investment platform bringing an endowment-style portfolio to everyday investors.

Before Ivy Invest, Wendy was Managing Director of Investments at the Mother Cabrini Health Foundation, where she built the Investment Office from the ground up and managed a $4 billion portfolio. Prior to Mother Cabrini Health Foundation, Wendy was Director of Investments at UJA-Federation, investing across a broad range of asset classes. Wendy began her career in the Investment Office at the Metropolitan Museum of Art. She has a Bachelor of Arts degree from Columbia University and is a CFA charterholder.

You can find Wendy on her socials here:
LinkedIn: https://www.linkedin.com/in/wendy-li-cfa/
X / Twitter: https://x.com/askwendyli

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

OUTLINE:

[00:00] Intro
[02:29] Wendy’s family’s history with Columbia University
[07:55] The importance of understanding family history
[11:09] Why Wendy chose to work at The Met
[15:16] How did Wendy know in the interview that Lauren would be her mentor?
[19:18] Specialist vs generalist in 2006
[22:58] Pros and cons of using AI as an LP
[29:02] The 80-20 rule for how an LP thinks
[29:29] The one mistake EVERY SINGLE LP makes
[33:27] What is the Takahashi-Alexander model?
[39:38] Who do you learn from when your LP institution is so small?
[41:22] The wisdom of an open-sourced LP reading list
[45:34] What is headline risk?
[47:09] What does ‘uncompensated risk’ mean?
[50:20] Why now for ‘endowment-in-a-box’
[55:07] Wendy’s proudest dish from her mom’s recipe book
[57:09] Wendy’s last piece of advice

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Where [using AI] is a challenge and can present a challenge to somebody’s development is in the utilization of these tools where perhaps there’s not an innate understanding of why the data is important.” – Wendy Li

“The pattern of mistakes that I certainly made and I saw the others make—and I know those listening and are earlier in their investor journey—will inevitably make-… We all make it. Even knowing this is a trap that we all fall into… even though they are all going to be aware of this trap, they’re still going to make the same mistake because we all do it, but we all have to learn this one and develop our own scar tissue on this one. It’s the exciting investment manager that other really smart LPs are invested with that is a ‘hard-to-access’ manager – that has a window in which they will take your capital. And there’s this sense of urgency. Sometimes real, sometimes forced. And there’s this sense that all these really smart investors are doing this thing. And the added layer on the endowment foundation side is oftentimes that there’s an investment committee member who is super excited about the investment because—and I’ll use a real quote that someone once said to me, ‘It would be a trophy manager to have in the portfolio’—and that is invariably a mistake that we all make in our investment careers. I would say that when I have been regretful of avoidable mistakes, it has had that pattern.” – Wendy Li

“I deeply subscribe to, ‘There’s always another train leaving the station.’” – Wendy Li

“There’s a great risk in being overconfident. There’s a great risk in assuming a normal distribution of events and returns.” – Wendy Li

“It’s not the probability; it’s the consequence. It’s not the probability when something goes wrong. It’s the consequence when it goes wrong.” – Wendy Li

“In-the-moment decision-making is always harder than you might remember post-mortem.” – Wendy Li


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

LP Relationship Management: The 2 Frameworks You Need to Build Trust

A while back, my friend Augustine, CEO and founder of Digify, asked me to write something for his company, Digify’s blog, about how I think about maintaining relationships between fundraising cycles when I was still an investor relations professional. As such, I wrote a mini two-part series on the frameworks and tactics I use to maintain LP relationships. Been given the liberty to cross-post on this humble blog of mine, in hopes that it helps any emerging managers or IR professionals here.

Voila, the first of two!


Author’s note [aka me]: My promise to you is that we’ll share advice you’ve likely never heard before. By the time you get to the end of this article, if you’re intimidated, then we’ll have done our job. Because that’s just how much it takes to fight in the same arena as people I’ve personally admired over the years and work to emulate and iterate daily. That said, this won’t be comprehensive, but a compilation of N of 1 practices that hopefully serve as tools in your toolkit. As such, we will be separating this piece into Part 1 and 2. The first of which is about overarching frameworks that govern how I think about managing relationships. The second of which focuses on tactical elements governed by the initial frameworks brought up.

One of the best pieces of advice I got when I started as an investor relations professional was that you never want your first conversation with an allocator to be an ask. To be fair, this piece of advice extends to all areas of life. You never want your long-anticipated catch up with a childhood friend to be about asking for a job. You never want the first interaction with an event sponsor to be one where they force you to subscribe to their product. Similarly, you never want your first meeting with an LP to be one where you ask for money.

And in my years of being both an allocator and the Head of IR (as well as in co-building a community of IR professionals), this extends across regions, across asset classes, and across archetypes of LPs.

So, this begs the question, how do you build and, more importantly, retain rapport with LPs outside of fundraising cycles? The foundation of any successful LP relationship lies in consistent engagement beyond capital asks.

To set the context and before we get into the tactics (i.e. what structured variables to track in your CRM, how often to engage LPs, AGM best practices, etc.), let’s start with two frameworks:

  1. Three hats on the ball
  2. Scientists, celebrities, and magicians

This is something I learned from Rick Zullo, founding partner of Equal Ventures. The saying itself takes its origin from American football. (Yes, I get it; I’m an Americano). And I also realize that football means something completely different for everyone based outside of our stars and stripes. The sport I’m talking about is the one where big muscular dudes run at each other at full force, fighting over a ball shaped like an olive pit. And in this sport, the one thing you learn is that the play isn’t dead unless you have at least three people over the person running the ball. One isn’t enough. Two leaves things to chance. Three is the gamechanger.

The same is true when building relationships with LPs. You should always know at least three people at the institutions that are backing you. You never know when your primary champion will retire, switch roles, go on maternity leave, leave on sabbatical, or get stung by a bee and go into anaphylactic shock. Yes, all the above have happened to people I know. Plus, having more people rooting for you is always good.

Institutions often have high employee turnover rates. CIOs and Heads of Investment cycle through every 7-8 years, if not less. And even if the headcount doesn’t change, LPs, by definition, are generalists. They need to play in multiple asset classes. And venture is the smallest of the small asset classes. It often gets the least attention.

So, having multiple champions root for you and remind each other of something forgotten outside of the deal room helps immensely. Your brand is what people say about you when you’re not in the room. Remind people why they love you. And remind as many as possible, as often as possible. This multi-touch approach is essential for nurturing a robust LP relationship strategy.

My buddy Ian Park told me this when I first became an IR professional. “In IR, there are product specialists and there are relationship managers. Figure out which you’re better at and lean into it.” Since then, he’s luckily also put it into writing. In essence, as an IR professional, you’re either really good at building and maintaining relationships or can teach people about the firm, the craft, the thesis, the portfolio, and the decisions behind them.

To caveat ‘relationship managers,’ I believe there are two kinds: sales and customer success. Sales is really capital formation. How do you build (as opposed to maintain) relationships? How do you win strangers over? This is a topic for another day. For now, we’ll focus on ‘customer success’ later in this piece.

There’s also this equation that I hear a number of Heads of IR and Chief Development Officers use.

track record X differentiation / complexity

I don’t know the origin, but I first heard it from my friends at General Catalyst, so I’ll give them the kudos here.

Everyone at the firm should play a key role influencing at least one of these variables. The operations and portfolio support team should focus on differentiation. The investment partners focus on the track record. Us IR folks focus on complexity. And yes, everyone does help everyone else with their variables as well.

That said, to transpose Ian’s framework to this function, the relationship managers primarily focus on reducing the size of the denominator. Help LPs understand what could be complex about your firm through regular catchups—these touchpoints are crucial for maintaining a strong LP relationship:

  • Why are you increasing the fund size?
  • Why are you diversifying the thesis?
  • How do you address key person risk?
  • Why are you expanding to new asset classes?
  • Are you on an American or European waterfall distribution structure?
  • Why are you missing an independent management company?
  • Who will be the GP if the current one gets hit by a bus?

The product specialists split time between the numerator and the denominator. They spend intimate time in the partnership meetings, and might potentially be involved in the investment committee. Oftentimes, I see product specialists either actively building their own angel track record and/or working their way to become full-time investment partners.

One of my favorite laws of magic by one of my favorite authors, Brandon Sanderson, is his first law: “An author’s ability to solve conflict with magic is directly proportional to how well the reader understands said magic.”

In turn, an IR professional’s ability to get an LP to re-up is directly proportional to how well the LP understands said magic at the firm.

My friend and former Broadway playwright, Michael Roderick, once said, the modern professional specializes in three ways:

  1. The scientist is wired for process. The subject-matter expert. They thrive on the details, the small nuances most others would overlook. They will discover things that revolutionize how the industry works. The passionately curious.
  2. The celebrity. They thrive on building and maintaining relationships. And their superpower is that they can make others feel like celebrities.
  3. The magician thrives on novelty. Looking at old things in new ways – new perspectives. The translator. They’re great at making things click. Turning arcane, esoteric knowledge into something your grandma gets.

The product specialists are the scientists. The relationship managers are the celebrities. But every IR professional, especially as you grow, needs to be a magician.

Going back to the fact that most LPs are generalists, and that most venture firms look extremely similar to each other, you need to be able to describe the magic and your firm’s ‘rules’ for said magic to your grandma.

For the next half, I’ll share some individual tactics I’ve worked into my rotation. Most are not original in nature, but borrowed, inspired, and co-created with fellow IR professionals.


This post was first shared on Digify’s blog, which you can find here.


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!


Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.