Launching Superclusters

Hello friends,

I did a thing.

I started a podcast.

So why the name Superclusters?

I’ve always been a fan of easter eggs. Cup of Zhou also happens to be one of them. Superclusters is another. But this time, rather than leaving it for surprise, I’d love to spell out why and with that, the purpose of this podcast.

In the startup world, we always say startups are the stars of our universe. They shine the brightest and they light up the night sky. We also have tons of aphorisms in the startup world. For instance, “Aim for the stars, land on the moon”. Startups are often called moonshots. They need to achieve escape velocity. And so on.

So if startups are the stars of the universe, galaxies would be VC firms that have a portfolio of stars.

And if galaxies were VC firms, superclusters would be LPs. Superclusters are collections of multiple galaxies. For example, the supercluster that the Milky Way is in is called Laniakea (Hawaiian for “immense heavens,” for the curious).

So why a podcast on the LP world?

  1. The LP industry in ten years will be much bigger than it is today. We are not even close to the TAM of it.
  2. The LP industry will be a lot more transparent than it is today. FYI, as many of you know already, the industry is very opaque. Many want and still like to keep their knowledge proprietary. But what’s proprietary today will be common place tomorrow. I’m not here to share anyone’s deepest, darkest secrets, or anyone’s social security number. That’s none of my business. But the tactics that make the greatest LPs great are already being shared over intimate happy hours and dinners between a select few. And it’s only a matter of time before the rest of the world catches up. We saw the same happen with the VC industry, and now people are moving even more upstream.
  3. I think of content on a cartesian X-Y graph. On the X-axis, there’s intellectual stimulation. In other words, interesting. On the Y-axis, there’s emotional stimulation, or otherwise known as fun. Most financial services (for instance, hedge fund, private equity, venture capital, options trading) content tends to highly index on intellectual stimulation and not emotional. And for the purpose of this pod, I want to focus on making investing in VC funds fun AND interesting.

You can find my podcast on YouTube, Spotify, and Apple Podcasts for now. In full transparency, waiting on RSS feed approval for the other platforms, but soon to be shared on other platforms near you.

You can expect episodes to come out weekly with ten episodes per season, and a month break in between each to ensure that I can bring you the best quality content. 🙂

You can find my first episode with the amazing Chris Douvos here:

Or if you’re an Apple Podcast person, here’s the Apple Podcast link.

Thank you’s

I am no doubt flawed, clearly evidenced by my verbal “ummmm’s” and “likes” in the podcast. But nevertheless pumped to begin this journey as a podcast host. I expect to grow in this journey tackling the emerging LP space and running a podcast, and I hope you can grow with me. So, any and all feedback is deeply appreciated. Recommendations of who to get on. What questions would you like answered. Formats that you find interesting. I’m all ears.

That said, I’m grateful to everyone who made this possible. My mighty editors, Tyler and JP. Without the two of you, I’d still be struggling telling head from tail on how to do J-cuts and L-cuts. The sole sponsor for the pod, Ravi and Alchemist. And while the pod itself is separate from Alchemist altogether, Ravi pushed me to make it happen. And for that and more, I am where I am now. Every single LP who took a bet on me for Season 1 when all I had for them was an idea and a goal. Chris. Beezer. Eric. Jamie. Courtney. Ben. Howard. Amit. Samir. Jeff and Martin.

And to everyone, who’s offered feedback, advice, introductions and pure energy to fuel all of this. Thank you!

And to you, my readers, I appreciate you taking time out of your busy day when there are so many things that fight for your attention, that you spend time with me every week! If I could just be a bit more self-serving, if you have the chance to tune in, I’d be extremely grateful if you could share it with one LP or one GP who could take something away from it.

Cheers,

David

P.S. Don’t worry. I’ll still continue to write on this blog weekly about everything else in between. That’s a habit I’m not willing to give up any time soon.

P.P.S. I’m already working on and recording for Season 2 of the pod, and I can tell you now that things will only get spicier.

P.P.P.S. Due to a million bugs and a half, I’m still working on launching a dedicated website for the podcast (superclusters.co), but until then, I’ll be sharing the show notes of each episode 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!


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 Think about LP Construction

ocean, ship, sail, family, together

Before we dive into this blogpost, I’ve been asked by my legal friends to include the below disclaimer. I have a version of this at the bottom of every blogpost, but nevertheless, it doesn’t hurt to reiterate it again.

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.


One of my favorite scenes as a kid was in Harry Potter and the Sorcerer’s Stone when Harry visits Diagon Alley for the first time. As the stone wall parted like the Red Sea, we saw a world unlike any we’ve seen before. With that, the audience along with Harry (Kudos for Director Chris Columbus‘ artistic direction) watched in wonder, excitement, and mystery. And Harry and I alike (Admittedly, I didn’t start reading the books till after the first movie) was hit with an overwhelming load of new information to absorb.

Raising your first fund is very much like that. While there are still some elements of familiarity, like investing in great people and winning great deals, you are taking other people’s money (OPM) for the first time. As such, it begs the questions: Who do you take money from? And how do you manage those relationships?

And like the stone wall in Diagon Alley, there’s more than meets the eye.

I have to thank Shiva for first bringing this topic to my attention, one that deserves a more nuanced breakdown than what is currently out there. And when Rebekah brought the below notion up for the Emerging LP Playbook, I knew I had to dedicate a blogpost to just this topic.

“GPs often have some flexibility on their minimum check size. I’m a pretty small check (particularly since I’ve been living on a founder salary!), but I can bring other things to the table to help the GPs I invest in (e.g. I highlighted Janine Sickmeyer from Overlooked Ventures in my Forbes column, I’m an advisor to Zecca Lehn from Responsibly Ventures, I send them deal flow from my AuthenTech community of founders). I’ve had luck with reaching out and saying ‘I really believe in what you’re doing. Please let me know if you get enough large checks and have room for some smaller LP investments.’ They’ll usually need to get enough big investments first since there are SEC limits on how many LPs they can have, and then they can let in some smaller, value-add LPs.”

The LP landscape is rapidly changing. What we knew in the last decade won’t get us to the next. The opacity in the LP world is getting undone by new, emerging LPs hungry to get involved and to learn. Folks, like Nichole at Wischoff Ventures have also shared publicly what her LP base looks like, with a level of transparency that’s foreign, yet refreshing for this industry.

Regulation has moved the needle, allowing for greater allocations to equity crowdfunding, as well as introducing more retail and high net-worth individual investors, to join the foray. Platforms, like AngelList, Republic, Twitter, Allocate, and Revere, just to name a few, are creating engines for better GP discoverability. There have been conversations on raising the ceiling on the number of accredited investors in a fund to 600. Which, if passed, will allow for smaller checks into funds, whereas the previous decades only allowed for family offices and institutions, as well as close friends. Anecdotally, I’ve also seen a lot of angel investors starting to allocate to funds rather than just purely startups.

And at this inflection point, as a GP, you need to be ready for this market shift that’s still early now, but starting to move. And hopefully, the below insights from 11 amazing GPs will serve as your wand, potions, owl and broom as you embark into the magical world of being a fund manager.

My methodology

To be fair, LP construction is more of an art than a science. So, I asked GPs who were on Funds I, II, or III. Why? Emerging GPs would best be able to relate a lot more to the hustle of finding and persuading different kinds of LP personas than someone who was on a Fund X or XV, who already have a long track record that speaks for itself.

I’m also a firm believer in tactical mentorship — mentors who are just 2-3 years ahead of you. People who have just been through the trenches you’re in and can share the lessons they learned. At the same time, not too far ahead where they are no longer the best people to check your blind side. After all, the lessons they picked up are still fresh in their mind. As a function, every one of these amazing GPs started their current fund in the past decade. The only caveat is that this may be the first recession they’re investing other people’s money (OPM) into, although they may have invested their own in the previous decade. And while that may be true, their lessons are timeless.

In the world of baseball, there’s the idea of breaking the catcher’s mitt. In other words, a new glove must be worn and used several times before it can achieve its full potential. Pitching to LPs and LP construction as a whole is no different. Just like a founder needs to pitch to several friends, colleagues, and investors, before they can hit their full stride during fundraising, raising from LPs requires many conversations and many iterations. Even Felicis’ brilliant Aydin Senkut got his first yes from an LP in Felicis after 107 iterations of his pitch.

So, in embarking on this topic and to get the best insight I could, it came down to two core pillars: the people I asked and the questions. I’ll start with the people.

The experts

If there were a periodic table of elements for GPs, who would be the canonical faces who would be on there? That’s who I needed for this blogpost. Not me, but them. So I did just that. I couldn’t be more grateful. A big thank you to Sarah Smith, Nichole Wischoff, Shiva Singh Sangwan, Vijen Patel, Eric Bahn, Paige Finn Doherty, Sheel Mohnot, Hunter Walk, Arjun Dev Arora, Steven Rosenblatt, and “Mr. Huxley” for your insights and edits. I know the below will go a long way.

Don’t get me wrong, there are a lot. And the folks included here are by no means all-inclusive. Many who had gone on to raise a Fund IV or higher. In effect, a few years or more out of the emerging manager game. Quite a few I didn’t know well enough. That’s on me. And some who, for all their goodwill and insight, unfortunately, were busy in the weeks prior to this blogpost coming out.

The questions

Building a firm with multiple funds is, in many ways, like driving a car through fog. Not my best analogy, but gets the point across. You see the rough outlines of the road just a few meters ahead, but you won’t see the sinkholes and the cracked concrete until you’re right in front of it, nor do you see any part of the road further than a few meters away. Or as Warren Buffett says, “The rearview mirror is always clearer than the windshield.”

Things are often painfully obvious in hindsight, but are scary, mysterious and unknown in foresight. Sometimes, you just don’t know what you don’t know. And as such, I write and I ask, in hopes to help the ones starting off, to develop foresight from the below cast’s hindsight. And to each, I had five overarching questions, coupled with follow-ups for more depth:

  1. What kinds of LP personas should a GP target at the beginning of their fundraise versus at the end?
    • In your experience, what do institutions look for before writing you checks?
  2. How active of a role do you ask your LPs to play?
  3. Are there any LPs you say no to? What is your framework for saying no?
  4. If you have one, how do you think about structuring your LPAC?
  5. What tools do you use to help manage your engagement with LPs?

LP Personas

As you embark on your fundraise, note that different LPs resonate with different pitches. Additionally, when you choose out to reach out to each persona, be aware of what each of these LP personas’ incentives are. As a seasoned LP once told me:

  • High net-worth individuals seek to learn and rarely have a financial incentive.
  • Small and medium-sized family offices seek to learn and access top decile deal flow.
  • Larger LPs, like institutions and fund-of-funds, seek financial return.

From my conversations, it seems most GPs raising a Fund I start with individuals, then target larger check sizes as their fundraise matures. For Fund IIs, many seem to start with finding an anchor LP first, before reaching out to individuals and family offices.

The truth is there’s no silver bullet. And you’ll see exactly why below. So what might be more useful to you, an emerging GP, are anecdotes of what worked for different funds. As I call it, tools for your toolkit.

I will note that the one LP persona I won’t touch on as much since I have a lack of data here are corporates who usually seek technology, as well as information access, largely for acquisition opportunities.

Individuals

Start with people close to you.

“You should always target friendlies first. Welcome your references and first believers who might be founders, individuals, former coworkers, classmates.”

— Sarah Smith, Sarah Smith Fund

“It all depends on which Fund you are raising, how much you are raising, track record, team, and many more variables.  If you are an emerging manager that is not spinning out of a brand named fund with a significant track record, you are going to have to be scrappy and start with people who know and trust you. “

— Steven Rosenblatt, Oceans Ventures

“You should always start off with your network – from the closest circle and outwards through the various concentric circles. At the beginning, you want to focus on finding your first believers. Those are your first-degree and maybe second-degree connections. So it’s less of the archetype of LP, but more so the depth of relevant relationship that matters. After the first close, that’s when you explore emerging manager programs or talk to more traditional asset managers — still largely within your first- and second-degree networks and/or those of your close early LPs and advisors.”

— Arjun Dev Arora, Format One

“The first $5 million is the hardest. Go to your friends and family. Build some momentum. After you get the initial momentum, it builds off of that. Everyone back channels everyone.”

— Vijen Patel, The 81 Collection

“For the beginning of a fundraise, I’d recommend asking for advice (before money) from people you’ve worked with for an extended amount of time. Your earliest checks may often be smaller but meaningful amounts from colleagues, co-investors, and GPs at other firms.”

— Paige Finn Doherty, Behind Genius Ventures

“The thing is my fund wasn’t oversubscribed from the beginning since I found it hard to raise. It’s a game of momentum, and in the beginning, I didn’t have any. In the beginning, it was about reaching out to the folks that you know. So, I mostly reached out to GPs and fund managers I knew and getting them through.”

— Shiva Singh Sangwan, 1947 Rise

“At the beginning, always start with people you have relationships with — people who’ve known you for a very long time. They not only want to invest in the fund, but invest in you. My first LPs would have likely invested in anything I created, but they knew I wanted to build a track record in venture. I’ve known one of my LPs since we were kids. Another was one of my best friends in university. Another was a friend of his.”

— “Mr. Huxley”, GP with two funds

Beware of relying too much on publicly available data to find LPs.

“The challenge with a purely data-driven approach (i.e. on LinkedIn or Pitchbook) is that you don’t understand the full rationale for why certain LPs invested in a fund. On paper, it may look like a family office is an LP in venture funds, but the principal at that family office could just be the brother- or sister-in-law of the GP. Most LPs also don’t explicitly say they’re LPs on LinkedIn. They could be an asset manager or a CEO of a Fortune 500 company. They almost always don’t want to be inundated with asks. Only after understanding why the industry is opaque, can you then understand LPs and find them.”

— Arjun Dev Arora, Format One

For potential MVP LPs, check size doesn’t matter.

“At the beginning of the fundraise, anyone that knows you and trusts you already AND can easily part with some money. Our first close was $20 million, and it was almost all people who knew us already – either directly or through our brand. We only had one new investor. In that group, we were lucky to have some fairly common names, which helped build the momentum for the rest of the fundraise.

“We did think about check sizes a little bit. There were some people we wanted to have involved for sure, and for them, the check size didn’t really matter. In our first close, we thought of people who could write a $250K check. And if there was someone we really wanted, we’d reduce it to $100K. I’m also an LP, and I do the same. If I plan to invest, I always negotiate down as well. The GP tells me X and I say I’ll invest X, divided by three.”

— Sheel Mohnot, Better Tomorrow Ventures

Persistence also speaks for itself.

“There are two types of investors: those who will commit to your fund now, and those who will invest after building trust. A lot of investors don’t like to invest in a Fund I. To keep them engaged, you either take a tiny check they’re comfortable with or you share regular LP updates that showcase your proof of work.

“In addition, you have to be clear with expectations. I bucketed potential LPs into four buckets:

  1. High net-worth individuals
  2. Founders and operators
  3. Family offices
  4. And GPs

“With each meeting, my pitch evolved and did a lot of follow ups. I had to show I was getting access to good deals and how I was getting access to those deals. You have to share the story behind that. That’s how you attract other investors. For instance, I remember sending my proof of work and an additional ten follow-ups to an LP. And each time I followed up, there has to be some new substance, value, and proof of work. It was a long process, but he ended up becoming one of my largest checks.

“Investors who were or are hustlers tended to gravitate towards my pitch. They became high-functioning people because of their hustle and respect me for my follow-ups and my persistence. They saw themselves in me. Similarly, founders are most likely going to get a reply from me who follow-up at least 2-3 times.

“The lesson here is that being persistent shows that you care. 99.9% of people won’t follow up, and by doing so, you’re already standing out.”

— Shiva Singh Sangwan, 1947 Rise

There are different ways to get in front of LPs: events, Twitter, deal flow, etc.

“Throw events for your LPs — a nice dinner or a cool experience — and ask them to invite their friends. Host events in a thoughtful way.

“Share relevant SPVs. Even broader, it’s content. Having founders be big fans of yours is also helpful. It’s a positive signal and creates buzz.

“That said, having co-investors who like you is a more direct path. LPs often ask VCs: Who are you co-investing with? Which emerging managers are you excited about? These LPs are looking for names. Some GPs are more generous with intros; while others prefer not to share but that’s OK as long as some do.”

— Arjun Dev Arora, Format One

“Looking back at my experience, a majority of our LPs from both Fund I and II actually came from Twitter and warm intros. I’m on Twitter a lot, mostly because I raised Fund I during the pandemic, so Twitter was where I hung out with many of my friends. I love to tell stories and as an extension I help founders tell their stories. And I host events and have done so since elementary school when I was on the student government event planning board. People are interested in my story because I don’t come from a traditional background. They invested mainly because they realize ‘she’s putting so much into the ecosystem, so it’ll eventually come back to pay dividends.'”

— Paige Finn Doherty, Behind Genius Ventures

Some individual LPs are not financially motivated.

“I want to preface that we only have foreign LPs, not US LPs. So, sophistication is very different. With European investors, while running a fund investing in the US, you can play the access game. In other words, you can sell access to great US companies. It’s something I lean on quite a bit.

“My LPs are quite sophisticated outside of the world of tech. They’re finance-savvy wealth managers, founders, high net worth individuals with net worths greater than $50 million, where they invest out of leisure and pursuing a mission, rather than for financial returns. They don’t understand venture, but want exposure to venture.”

— “Mr. Huxley”, GP with two funds

Start with HNW individuals, and end on family offices.

“Let’s make a few assumptions here. Let’s assume this is a Fund I and an emerging manager who doesn’t come from an extreme pedigree. Not from Sequoia or the like. This person is a decent operator-turned-VC, investing with a cool thesis. I’m going to also assume they’re not going to raise a $50 million Fund I or greater. They’re staying small and only raising $10-20 million.

“So I break down LPs into four categories.

  1. High net-worth individuals – These are your angels.
  2. Family offices – They have a lot more assets, usually $100 million or greater.
  3. Fund of funds – They have a mandate to invest in other funds.
  4. Endowments – These are very large institutions, maybe even sovereign wealth. They tend to write big checks into big funds.

“The big mistake I see many GPs make is that most GPs try to target the big ones out of the gate. Rather, in the beginning, focus on the high net-worth individuals. This is similar to asking angels. Their conviction and speed is quick. Their typical check size is no greater than $100K.

“Once you get a few million in the bank, then focus on the family offices — the $1-5 million checks. They tend to operate a lot like angels, but have just accumulated a lot more wealth. Around Fund II or III, then you target larger institutions.

“So, my recommendation is that as an emerging manager, start with angels, end with family offices.”

— Eric Bahn, Hustle Fund

“When you get closer to a final close, and you have a small fund, you can always welcome 1-2 family offices who can write small checks as well as individual investors who can be really helpful.”

— Shiva Singh Sangwan, 1947 Rise

Family offices

Find LPs by optimizing your search with certain keywords.

“Ask your existing LPs if they know anyone. Search LinkedIn to make their life easier. To find LPs, I would recommend looking up the keywords: Venture capital, asset manager, family office, emerging manager, startup (or venture) ecosystem, allocation, active allocator. All the above implies someone is putting money to work.”

— Arjun Dev Arora, Format One

Ask each person for just one intro, nothing more.

“Hustle Fund today has hundreds of LPs in our pipeline. But when we started off, we didn’t know a single family office. So, at the risk of sounding unintentionally mean, here’s how I think about it. Finding a family office is kind of like finding a cockroach. It’s always hard to find the first one. But once you find one, you’ll find a whole nest.

“I’ll share a tactical networking tip of how we found family offices over time. So, let’s say we chat with David. He likes us and decides to invest in the fund. We then share our fundraising blurb and deck and ask, ‘Do you mind sending this to one person you think would be a good fit for our fund?’

“The mistake I see a lot of other fund managers make is they ask, ‘Do you mind sharing this to anyone you think would be a good fit?’ Don’t ask for too much. There’s just too much paradoxical choice. There’s too many in their network to choose from and that overwhelms them.

“So, we change the question to just ask for one. That’s it. Generally, they think of the richest person they know. With just one intro, you’re magically in the family office world. A rich person tends to be friends with a lot of other rich people. It is secretive, but they also talk amongst each other a lot. When they invest, they like to bring their own friends in too.”

— Eric Bahn, Hustle Fund

Ask for intros to LPs who backed GPs who look like you.

“Another big filter is to find LPs who have backed GPs that look like you or have a similar investment strategy. For me, it was finding LPs who have backed solo GPs. To be fair, it’s not easy to figure out, since it is a rather opaque industry. So, I had other solo GPs I knew well and have co-invested with help make intros to their LPs.

“For LPs that I’ve never talked to before, a question I always ask LPs is: ‘Have you ever backed a solo GP?’ If not, don’t waste your time as you’re extremely unlikely to be their first. They likely have strong philosophical reasons to not back solo GPs so your meeting time is better spent elsewhere.”

— Sarah Smith, Sarah Smith Fund

Institutional LPs

Don’t underestimate the power of an anchor LP.

“If possible, having a respected entity who could anchor 5-10% of the fund would be ideal. In my case, my former partnership Bain Capital Ventures anchored my fund which was ideal because it keeps us connected and they are well known in the industry. Just like for a founder, having a lead is important. Having an anchor early helps you build momentum to close the rest of the fund.”

— Sarah Smith, Sarah Smith Fund

“For Fund II, I wanted an anchor LP to provide stability and credibility in the fundraise. Cendana was my number one pick. As a function of fund size at the seed stage, they’re definitely the best. The Harvard of LPs. To become part of their community, for me, was really important.

“It was a hard process, but was doubly as difficult, since Josh and I went our separate ways for Fund II. We had to communicate that decision to our 120 LPs in Fund I before starting the fundraise.

“In Fund I, some LPs believed in me. Some believed in Josh separately. I remember fondly of our first $10K check of belief capital. BGV’s most expensive decisions were our investment decisions. We made all our decisions together in Fund I. We also tried doing a few SPVs via Assure. While it was a great start to our career in VC, it required more work than we thought made sense. But for Fund II, it was going to be different. It was just me. No more SPVs, just checks out of the fund. The story itself wasn’t hard to communicate, but when we got to our 70th call, it was hard to sell the same emotional story.

“So, once we did, I put in the work. I flew to Australia to get introductions and to meet his teammate. Whenever I chatted with other GPs that were backed by Michael [Kim], I’d ask them to say hi to him.

“Pitching to Cendana, and most importantly, Michael, was the longest sales process I’ve ever gone through. He passed on Fund I, but he finally said yes to BGV’s Fund II. Along with Michael, GREE also doubled down on Fund II, along with operator checks from folks at Dropbox and other companies.”

— Paige Finn Doherty, Behind Genius Ventures

Bigger LPs have the ability to write smaller get-to-know-you checks.

“At the end of Fund I, we ended up with Cendana, Greenspring, Industry, Vintage, and Invesco. All fund-of-funds, but they all wrote relatively smaller checks than they typically do. For all the afore-mentioned funds, they wrote $1-3 million checks. It was a get-to-know-you check. They would talk to other companies in our portfolio and other managers we co-invested with. And so the best way to get in front of them was to get intros from other managers these fund-of-funds invested in.”

— Sheel Mohnot, Better Tomorrow Ventures

Talk to LPs whose minimum check size is 20% or less of your fund.

“Some CIOs like being in Fund I’s; others don’t. There’s a lot of alpha in Fund I. At the same time, there are others that won’t consider you seriously until Fund III. The challenge is figuring that out as quickly as possible.

“The best filter for this is figuring out what their minimum check size is. And, is that greater than 20% of your fund size? If so, it won’t be a good fit.”

— Sarah Smith, Sarah Smith Fund

“Biggest thing is their own AUM and the amount they need to deploy. First barrier to entry is the size of the fund you are raising as the GP. If you are raising sub-$75M (give or take) it wouldn’t be big enough for their minimum check size. LPs don’t want to be even close to a majority of your fund, or likely more than 20%.”

— Nichole Wischoff, Wischoff Ventures

“Some institutional LPs also cannot write small checks since they are dealing with other variables around their asset allocation models.”

— Steven Rosenblatt, Oceans Ventures

Start conversations early with LPs who can invest in the ideal fund size you want to raise.

“It’s not just about what your fund size is today, but where you aspire to be. Say you have a $25 million fund today, but aspire to have a $150 million fund where you lead Series As by Fund III or IV, then you should still talk to LPs who are able to write checks that are 20% or less of that future fund. It’s important to know there may be incredible university endowments or foundations who really like you as a GP but in order to run their business efficiently, they have to be able to write minimum checks of $25M or even $50M+ which means they only seriously consider funds of $150M+.

“The question for you, the fund manager, is: Are you going to grow your fund size over time? Or are you going to stay consistent with your current fund size? If the former, then you need to spend a fair bit of time in your deck about how your strategy will shift over time and some views into those larger future funds.”

— Sarah Smith, Sarah Smith Fund

“I started having conversations with institutions while I was raising Fund II knowing they wouldn’t come in until Fund III at the earliest. You need a lot of touchpoints and time with these types of LPs before they invest. I am very focused on LPs that want to underwrite me/the fund for years. I want long lasting relationships and partners that can come in fund over fund.”

— Nichole Wischoff, Wischoff Ventures

“So, when I speak to institutions that are more data-driven — they think about the scalability of AUM — I knew many of those folks were not going to be the best fit. That’s why raising Fund I was so hard.”

— Paige Finn Doherty, Behind Genius Ventures

“We have been cultivating relationships with a large amount of institutional LP’s over the last few years.  Investors invest based on trust and relationship and in our mind that doesn’t happen overnight.”

— Steven Rosenblatt, Oceans Ventures

LPs hate surprises.

“There are some institutional LPs who will give you transparent feedback and transparency about their process but most do not.  The #1 thing that rules them all is track record and performance. Institutional LPs don’t want surprises; they want to see a multi-year established track record in what you are investing in.”

— Steven Rosenblatt, Oceans Ventures

And even if they disagree with you, LPs like consistent LP updates, even prior to their investment.

“We have a couple institutions that have invested in Hustle Fund. What I didn’t appreciate out of the gate is how long it took to build those relationships. They want to see at least one fund cycle, ideally two. That’s usually anywhere between two and four years. But we’ve nailed how we do it passively.

“We have a newsletter that goes out on the first day of each month at midnight — every month for the past 5.5 years. Each issue has two things: a state of the market and a deal memo on each deal we’ve invested in.

“Today we have 150 investors across three funds and an additional 450 investors who have not invested yet. Think of it like a monthly drip campaign for these prospective investors. Investors get to see what we execute against what we say we’re going to do.

“In some cases, these investors like what they see and choose to eventually invest. In other cases, they find themselves totally disagreeing with how we run our process so they don’t invest, and that’s okay, too. Drip campaigns are always a great marketing tool to close customers. That’s no less true for Hustle Fund. So, at some point, when we mention we’re going to raise a Fund IV, all the meetings will just line up.

“I’ll share a story. Our biggest LP, Foundry Group — Jaclyn and Lindel run their LP initiatives — initially didn’t like our thesis and approach. To them, our investment model was a little too spray and pray. But at the end of our Fund II, they told me, ‘Even if we’re a little uncomfortable with your thesis, you’ve been so consistent with sharing how you’re learning and developing, and we love it. So, we want to invest now.’ They invested because of our newsletter, and witnessing our exact fund thesis. You gotta put in the work. And if you do, the money will follow.”

— Eric Bahn, Hustle Fund

Give LPs a compelling reason not to back an established fund. Otherwise, they will.

“Every institution is different, but it’s also really important to realize that with most institutions, the decision maker is not making the decision based on their own capital. So, risk is a huge point. No one is going to get fired for backing Sequoia. They could potentially get fired for putting a huge check into a new emerging manager that isn’t proving anything and going backwards. It’s important to understand the incentives of who you’ll be working with. So institutions are a completely different beast than individuals. Anything they do there’s usually 5 to 10 back references. It’s a small world. For pushback, they want to see a track record, which is really hard for emerging managers. And they want to see some sort of pedigree.”

— Vijen Patel, The 81 Collection

“I’m the horrible anomaly of being able to raise from institutional LPs in my first fund. I’ll chalk up timing, privilege, and reputation as being the reason we were successful in doing so. While not all of this is relevant to emerging managers today, 100 Days of Fundraising was a blog post which detailed how Homebrew ran its process.”

— Hunter Walk, Homebrew

Author’s Note: Of particular note, in Hunter’s alluded blogpost, is when he writes:

“What we also had was a point of view as to where we’d be investing: the Bottom Up Economy. This set us apart from other funds with broader or non-descriptive investment principles. We also had given extensive thought to our portfolio construction strategy around playing lead roles in rounds, the number of deals we would do each year, how much capital we’d hold back for follow-on, etc. The combination of these two meant that a fund could see how we’d be differentiated in the marketplace and where we’d fit against their current exposure.”

Should your LPs be active?

The truth is, and you’ll read this below, most LPs are passive. But in a world where you take so many different types of risk as an emerging GP, it helps to have people you can lean on. So, it really comes down to two questions:

  1. What can you ask of your LPs?
  2. What is the upside and downside to having active LPs?

The bull case for active LPs

HNW individuals are just waiting for the ask.

“The LPs I love working with are the ones who are going to be actively involved. They share their expertise with the portfolio, answer our questions, and are willing to jump on random calls with me. A lot of our LPs are high net-worth individuals, and they’re just waiting for the ask. They’re waiting for the GPs who they invested in, to engage with them. Sometimes, all it takes is a 20-minute call to share deals or thoughts or questions.”

— Paige Finn Doherty, Behind Genius Ventures

Your LPs will make LP intros if you have a good story.

“I think you can do a good job of getting LPs to send intros. If you can build trust and tell a good story, your LPs will naturally tell others because it comes up at a cocktail party organically. A VC fund is more interesting than ‘Hey I invested in a new ETF.'”

— Vijen Patel, The 81 Collection

Incentivize your LPs with additional carry.

“With Fund II, my Fund I LPs opened the door to other LPs in their network. Additionally, I am quite generous with my 20% carry for running the fund. I share 5% of the carry pool with other founders and LPs who send me deals, help with diligence and introduce me to other LPs.”

— “Mr. Huxley”, GP with two funds

Leverage your LPs’ brand to win deals.

“In my case, I had smart and well-connected LPs, and I was able to win deals because of them by inviting them into deals I wanted to get into. Some of my LPs happened to be fund managers as well, and I have been able to learn a lot from them.”

— Shiva Singh Sangwan, 1947 Rise

Build communities alongside LPs.

“I do believe there is room for LPs to provide value on top of what we expect today – better ways to tap their networks on behalf of our portfolio companies for example. At Screendoor for example, a fund of funds that backs underrepresented emerging managers, we strive to create a community among these VCs to support each other, and also pair them with VCs (like me) who can be coaches along the way when they have questions about firm building.”

— Hunter Walk, Homebrew

If you’re doing something for the first time, ask institutional LPs how other managers they’ve backed have done so.

“Since their investment offices have decades of experience in the venture sector and exposure to top managers across all stages, we often turn to them to gut check our reality against their perspective of the market. And when we encounter a type of situation for the first time, understand how other managers have approached the solution.”

— Hunter Walk, Homebrew

Author’s Note: Paige’s anecdote on how she engages her LPAC below is a great +1 to this point.

Let your LPs choose the kind of LP they want to be.

“I have no preference here. Rather, I’m open to what my LPs want their experience to be like. I have LPs that want to be more passive, as well as operator LPs who want to learn more about investing, lend expertise during diligence, facilitate customer intros, and even help out portfolio companies with hiring.

“After my LPs wire their money, I send them an intake form where I ask the question: How would you describe yourself as an LP? I have a number of statements they can select to indicate whether they are a newer or more experienced LP, if they’d like to be more active with founders, how often they’d like to communicate with me, and if they are interested in co-investment opportunities and events. I have another question following that: If you want to be more active, what are ways you enjoy helping?”

— Sarah Smith, Sarah Smith Fund

“I leave it completely up to them, but they typically opt to be more active. I host monthly one-hour office hours, share quarterly updates and deal reviews. For office hours, while we mostly chat about interesting deals I’ve been seeing in the last 30 days, my LPs can ask me anything. I try to be as communicative as possible – valuations, deal memos, and diligence. Sometimes they ask me to set up an additional SPV if they’re interested in putting additional capital in. I have a separate Airtable for deals we’re diligencing at the moment which LPs have access to. If they’re interested in a deal, they can reach out and ask. If not, they don’t have to.”

— “Mr. Huxley”, GP with two funds

The bear case for active LPs

Having engaged LPs is a lot of work.

“Candidly, I don’t want LPs that want to be super engaged outside of maybe one or two. It’s enough work as it is with quarterly reporting, etc. I want LPs focused on returns. Cendana is the most active with me and in great ways because they have so many emerging managers. I can strategize on fund size, raise timing, first hires, etc.”

— Nichole Wischoff, Wischoff Ventures

Emerging LPs want to learn from you, but remember you’re an investor, not a professor.

“Emerging LPs want that education. For emerging LPs who write a $5 million check or greater, they might like for you to jump on a call every quarter to educate them and share your current portfolio and what else you are seeing out in the field.

“Also, be thoughtful about how you’re managing your time, so that you don’t turn into a full-time venture professor. You’re an investor, a GP. That’s what you’re getting paid to do.”

— Arjun Dev Arora, Format One

Then again, most LPs are just passive.

“Most LPs are pretty passive. Sometimes they are helpful by making intros to our portfolio companies. We also like getting a pulse on the market from them.”

— Sheel Mohnot, Better Tomorrow Ventures

“Mostly passive. Most of the time, when the deals are good, they require little involvement.”

— Shiva Singh Sangwan, 1947 Rise

GP-LP fit: Red flags and things to watch out for

Avoid LPs who ask for special terms.

“These are long-term marriages, really long term. If you are going to be partners for the next 10-20 years, you better like each other. We have a no-asshole rule. We want investors who believe in our approach and ethos. My mentors at some of the top VC funds of the last 20 years have also coached us to keep the terms clean and I think a lot of emerging managers feel pressure to give special terms and ownership of their management company or GP, and long term, that might be something you regret.”

— Steven Rosenblatt, Oceans Ventures

“While I haven’t said no yet, I have selectively not followed up. For example, after talking with other GPs, I’ve heard some LPs were tricky to manage – outside the norm. It’s okay to expect quarterly communications, but when people start pushing an agenda, that’s too much.

“Avoid LPs who ask you to give up economics as a GP or change your terms. LPs who want to negotiate lower management fees, a different carry structure, or they want to own 20% of the general partnership for the next three funds are best avoided if possible. They want to change the terms that everyone else has. I wouldn’t allow that. If other LPs find out (and they eventually do), it would cause my LPs to lose trust in me and rightfully be frustrated that they got worse terms.”

— Sarah Smith, Sarah Smith Fund

Do your LPs’ goals align with your fund goals?

“As we got into the process we realized there was, at the time (2013) some other attributes we needed to take into consideration. One for example was the LP’s definition of success.

“We wanted LPs who were investing in us solely because they thought we’d be good stewards of their capital and return above-benchmark results. If there was a second agenda that they made obvious we typically declined the opportunity to work together. Our mindset was that there’s so much risk in trying to build a new firm, let’s focus all of our energy on a single definition of success: cash on cash returns. That precluded taking capital from LPs who were emphasizing direct co-investment (some of our LPs have direct practices and we love to bring them in to portfolio company cap tables when there’s mutual interest but we didn’t want it to be an expectation) or strategic investors who had interests in our portfolio different than our own (e.g. corporates that wanted access to market information).”

— Hunter Walk, Homebrew

Do you have the bandwidth to teach?

“If someone wants to learn, that can take a lot of time. Time that, for you, might be better spent elsewhere. If you’d rather spend the time elsewhere, like with your portfolio or investing, be clear with expectations. And if they don’t budge, don’t take that money.”

— Arjun Dev Arora, Format One

Beware of round tripping.

“I actually couldn’t take any Indian capital due to regulations. There’s a thing called ’round tripping.’ If a fund in India invests in a fund that’s built in the US, then invests back into Indian startups, that’s round tripping. And unfortunately, not allowed.”

— Shiva Singh Sangwan, 1947 Rise

Check your CFIUS rules.

“Before you say yes to LPs, check the CFIUS rules. Under those guidelines, you may not be able to take money from certain countries and parties.”

— Arjun Dev Arora, Format One

Did you take the right capital from the right people?

“Even though we heard ‘no’ a lot during our first fundraise we also turned down some offers. We’d already done a good job of pre-screening out LPs who we didn’t think were values aligned with Homebrew (e.g. money came from sources/institutions we wouldn’t want to work on behalf of).”

— Hunter Walk, Homebrew

“If they’re asking for things that you’re not comfortable with, then you probably shouldn’t work with them. The key is that there should be zero second-guessing. You need to be in a relationship with partners you won’t regret, during bull and bear markets. Ask yourself, ‘Did I take the right capital from the right people? Sometimes, it’s about where that capital came from and if you feel good about that. If there’s any inkling of doubt, don’t take the money or it’ll come back to haunt you.”

— Steven Rosenblatt, Oceans Ventures

“You need to communicate your clear values as a fund and long-term platform. Any LPs not aligned on your mission and values would be people to say no to quickly.”

— Arjun Dev Arora, Format One

“So, I did say no. I turned down a million dollar check because I didn’t feel comfortable with him being in front of a founder. And we’re very geared on our community. Money’s nice, but it’s not everything.”

— Vijen Patel, The 81 Collection

“Another thing to be mindful of is if an LP has a history of making verbal commitments and then changing that number at closing. You want a reliable and trusted relationship. If you did a reference with another GP, and heard that an LP cut their commitment by 50% at the last minute, that capital’s just not worth the risk to me.”

— Sarah Smith, Sarah Smith Fund

Don’t tolerate disrespect.

“I said no to a few LPs in Fund II. This was largely because they were super disrespectful during the raise process. I had an LP fly in from the UK after already committing and was so insanely rude to me in front of his all-male team that I decided not to work with them. I also try to be very transparent for folks that might not be a great fit for the fund.”

— Nichole Wischoff, Wischoff Ventures

“Small things I look for include off-color jokes, like ‘Look at that hot chick,’ or asking stupid questions. Some LPs have said this to Elizabeth, ‘How do you balance being a mom and being a full-time investor?’ I dare people to ask me that question. I’m a dad and I’m still doing it, but no one does.”

— Eric Bahn, Hustle Fund

Author’s Note: Eric goes into much more detail on ten reasons why you shouldn’t take LP money here, which I highly recommend a read.

Are your LPs disengaged during the diligence process?

“There are people who are disengaged in the diligence process. Those are people who are usually a bad fit.”

— Paige Finn Doherty, Behind Genius Ventures

Look for complimentary experience and diversity of opinion and experiences.

“Like any cap table or LP base, what is important to us is to have partners who can grow with us for a long period of time and where we have diversity of thought, experience, and exceptions.  It was really important to Oceans and our ethos to have amazing founders and tech execs as LPs early on who could be great to lean on for diligence and additional leverage to support our founders and entrepreneurial family offices.  At the same time we have LPs who are extremely valuable on the finance side and who have a long history of investing in venture. Complimentary experience and diversity of capital is really important to us.”

— Steven Rosenblatt, Oceans Ventures

“I also want to put it out there that GPs should be intentional about their LPs. For me, I aim to have my LP base include at least 50% who identify as women or non-binary, 10% black or Latinx, and 10% LGBTQ. Be intentional and solicit a diverse group of people. People talk about the diversity of founders and venture investors, but not about LPs. I think a lot about wealth creation, and it starts from the very top. I think people should be thinking about that a lot more.”

— Sarah Smith, Sarah Smith Fund

Don’t discount vibe.

“For Fund I, we had a chance to close $30 million worth of LP capital, but we only chose to raise $11 million. That’s a lot of people we said no to.

“It comes down to say a single word: vibe. It’s kind of like a marriage. ‘You’re trusting me with your wealth for a decade, if not more. It’s not a relationship we take lightly.’ I also share all the reasons why it won’t work out. So our LPs know what they’re getting themselves into.

“If something feels off, I don’t have to explain it. No one on our team has to explain it. If your gut feels like this could be off, we should just always trust that. Those one or two LPs your gut tells you is off are likely going to be super annoying,

“People like to logos their way out of things, but you really have to go back to gut feel. It’s almost never worth it. I can’t explain what an asshole feels like. But when you meet one, you know it.”

— Eric Bahn, Hustle Fund

“If I have a gut feeling that something is weird, then I trust that.”

— Paige Finn Doherty, Behind Genius Ventures

Big checks prevent you from bringing in other LPs you want.

“We haven’t had to say no to that many LPs. In our case, we either told them, ‘It’s too late – we’re full now and don’t have room for you.’ Or we talked LPs down from how much they wanted to commit. We had an LP who initially committed $22 million. And we told them, ‘Hey, we want to add more investors to our fund, so we don’t want to have any investors who commit more than $15 million.’”

— Sheel Mohnot, Better Tomorrow Ventures

Sometimes, the check size is just too small.

“I’ve said no because people wanted to invest below the minimum. To which, I told them to wait until they could meet the minimum. I’m not in the business of putting people in financial distress. And if my minimum, which is modest by design, $100K, called over two years, puts people in a position where they are stressed out, they shouldn’t invest in me or perhaps venture as a whole.”

— Sarah Smith, Sarah Smith Fund

“As the fund grew, I would turn down certain individuals due to check size.”

— Paige Finn Doherty, Behind Genius Ventures

But check size can vary based on an LP’s value to you or the portfolio.

“I also only reached out to people I wanted to have on board. The minimum check size did vary from individual to individual, which I largely based it off of the value they could provide for the fund and my portfolio companies.”

— Shiva Singh Sangwan, 1947 Rise

Or don’t settle and aim high.

“I hate the word ‘oversubscribed.’ It’s something I was lucky to learn very early on. Early in my career I had a board member say to me that if you hit your goals every quarter, your goals aren’t high enough.”

— Steven Rosenblatt, Oceans Ventures

Author’s Note: As you might realize even more after the last three pieces of advice, there’s really no right answer.

How do GPs think about building an LPAC?

Your anchor and other major LPs will ask you to create one.

“On the LPAC, I think I can confidently say that no fund manager wants an LPAC and proactively creates one. It is usually the ask of an anchor LP as you scale fund size. For example, for my second fund, I was asked by an LP to create one, and I was told a good number of LPAC members is three. You want the anchor LP in the LPAC because they are your biggest investor, and the two others should be trusted partners who want to help you. It’s up to me who I ask assuming not many have asked to be a part of it.

“I’ve been told most managers will have a bi-annual quick check-in call just to talk about how things are going. TBD if I ever do this. On the other hand, a lot of managers try to wait until they have at least $100M in AUM to give into an LPAC. But I didn’t say no.”

— Nichole Wischoff, Wischoff Ventures

“I think it’s, in large part, who wants to be on it. A lot of your larger LPs, in exchange for 10% of your fund, want to be on your LPAC. There are some investors who committed 10% but don’t want to be on it. It’s not like a board. If people want to be on it, it’s okay.

“We have five on our LPAC, and it’s a good number. We give them an early look by sharing with them our plan and fund deck. So, they gave us early feedback, like on carry structure.”

— Sheel Mohnot, Better Tomorrow Ventures

If a smaller LP wants to be on the LPAC, push back by giving them options that fit what you’re looking for.

“There are no real rules about how you approach them. We typically like to have our largest investors in it, at least symbolically. They’re putting in the most risk, so they should have a say in the direction of the firm.

“If someone does ask for it, and if they aren’t a large enough check, we tell them, ‘We like to reserve this spot for our largest LPs because they have the largest exposure in our fund. We’re open to you being a member in our LPAC, if you increase your check size.” That way, you can leave the ball in their court. Either, they won’t push further or they’ll commit more capital to the fund.”

— Eric Bahn, Hustle Fund

Evaluate a potential LPAC member on five different dimensions.

“So I will preface that emerging funds — Funds I to III or IV — are different from established funds, which have a mostly institutional base. Those who tend to write large checks may also be more inclined to want a seat on the LPAC.

“We look at it from these different dimensions, which we categorize into:

  1. Flexibility,
  2. Complementary skills,
  3. Ability to give honest feedback
  4. Value, and
  5. Capital

“So, flexibility is important because we’re not an institutional fund yet. The construction of the committee depends on the ebbs and flows of fundraising. Some investors don’t want to be on an LPAC — conflicting interests, not wanting to be actively involved, or just don’t want the time commitment. This’ll admittedly look very different for an institutional LPAC down the road for someone who has several hundred million in AUM. Institutional LPs will ask to have a seat on the LPAC, especially if they’re writing a check that accounts for 20% or more of the fund.”

— Steven Rosenblatt, Oceans Ventures

Go to them if you plan to go off-thesis.

“You go to them for things you might think are a conflict. For example, if I say I write $1M checks and I am considering going off-thesis and writing a $250K check, I might want to gut check and get a thumbs up that I’m not being an idiot. It would be a super simple email saying: ‘Hey team, here’s the scoop – please share thoughts.’ It’s very loose.”

— Nichole Wischoff, Wischoff Ventures

Ask your LPAC what they’re seeing in other managers they’ve backed.

“I didn’t expect to negotiate my LPA with Cendana. I have Michael [Kim] and Yougrok [from GREE Capital] on my LPAC. Youngrok is someone I meet with very often. And since GREE backed us since Fund I, he’s seen my growth as a fund manager. Our LPAC offers a great and critical lens into the industry.

Individually, I chat with both quite often. Together, as an LPAC, we meet quarterly. We’re also going to have our first general annual meeting on April 21st.

What’s great about Michael and Youngrok is that I’m not afraid to ask questions I think are dumb. If you’re in your Fund I or II, like I am, you’re still figuring shit out. You’re still testing what works and resonates and what doesn’t. I ask them, ‘what have you seen other managers do in this situation?’ They’ve worked with so many other managers, and in learning from their deep knowledge, I’m better off as a manager. It’s about building BGV as a long-term institution.”

— Paige Finn Doherty, Behind Genius Ventures

Your LPAC is your LP base’s chief influencer.

“One useful note about having an LPAC is that sometimes you want to make a minor change to the LPA. Say you originally planned to only invest in North American companies, but now you want to invest 5% of the fund in African startups. If you don’t have an LPAC, you have to go back to all your LPs each time you change the parameters of the agreement. If you have an LPAC, they can approve those minor changes for you on behalf of the rest of the LPs.”

— Sarah Smith, Sarah Smith Fund

“To be honest, I’m still confused about the purpose and concept of an LPAC. I like to think of the LPAC as the influencer of the LP base. They keep the investors’ interests in mind and help you communicate hard decisions to your investors.”

— Eric Bahn, Hustle Fund

Consult your LPAC for tough decisions.

“It definitely matters more at the end of the fund life. For instance, if we want to wait an additional year for Stripe to IPO. Then we consult with our LPAC to figure out the best way to message that to our LPs. Additionally, we can ask them what they think about a deal we’re about to do. It can also be useful in corporal situations. Hypothetically, if Elizabeth was beating me up, I can ask our LPAC to help me remove her.”

— Eric Bahn, Hustle Fund

“Since we’ve got a very small group of LPs that make up 95%+ of our funds, there isn’t much difference between our relationship with our LPAC and the other LPs. That said, we do have an LPAC and it’s composed of the largest investors in our funds. We meet with them once a year – typically a lunch before our annual meeting. And share the materials/discussion with the rest of the institutional LPs as well, so it’s less about anything confidential and more about a group of stakeholders we can get feedback from. Of course there are sometimes administrative aspects (approve us raising our recycling limits for a fund) but more often than not Satya and I are seeking feedback on questions we’re facing about how we want to manage the firm, tradeoffs between short and long-term thinking, and such.”

— Hunter Walk, Homebrew

“For us, when we constructed our LPAC, the questions we asked ourselves were:

  • Who do we think would be valuable in helping us balance short term decisions with long term thinking?
  • Who do we think will give us honest feedback and engage in honest conversations?
  • And who do we know has complementary DNA?”

— Steven Rosenblatt, Oceans Ventures

Find LPAC members who come from diverse experiences.

“I use it as a mini-board. I won’t go to it for big decisions, but I like the idea of surrounding myself with people who have different experiences than me, who have dissent, and make me a better investor.”

— Vijen Patel, The 81 Collection

Build an LPAC of different LP personas.

“If you have a great LPAC, they’re almost like a board of directors. You have some kind of cadence to get advice. If I did have one, I would like to do it with a group that represents my LP base – a few family offices, individuals, and people who could give really good advice.

“For first-time funds, you don’t want it to be any more than three to four people. And four to six for more established funds.”

— Sarah Smith, Sarah Smith Fund

“My advice to other VCs in building their LPAC would be to remember it’s about institutions, not individuals – your LPs representative might change over the course of the years. And, if applicable, to make sure you have a mix of LP types – for example, if your fund LPs are a mix of evergreen investment offices (such as most endowments) and folks who think of returns on a different cycle (fund of funds), include both.”

— Hunter Walk, Homebrew

The tech stack of engaging LPs

While I didn’t ask everyone this question, thought I’d share what notes I did have on some firms’ tech stack for engaging their LPs and managing their investor relations.

Wischoff Ventures — Airtable, Figma

“A spreadsheet/Airtable — I have everyone’s emails and copy-paste when I’m ready to send a quarterly update. I only talk to most once per quarter and it’s for my update. I built that in Figma (wouldn’t recommend it).”

Oceans Ventures — Affinity

“We use Affinity to manage our LP CRM. Our existing LPs get quarterly reports. And we try to write an LP update at least two times a year but will also often put out memos especially during key market moments. Also, since day one, we have a newsletter that keeps people up to date. It goes out every two to three weeks. And we have a personality. We’ve had other VCs tell us how excited they are to read it and we have LPs tell us they love our newsletter. We try to over-communicate and keep them heavily engaged.”

The 81 Collection — Streak, Airtable, Hubspot, Excel/Google Sheets

“We use Airtable, Hubspot, Excel and Google spreadsheets, but Streak is our main thing.”

Behind Genius Ventures — Cloze, Airtable, Google Drive, Webflow, Zapier, 1Password, Calendly, Twitter, Descript, Riverside

“We’re pretty software-heavy — something I picked up from my time at WorkOS. We use:

  • Cloze — as our CRM, where we track what cities folks are in in, who’s in the pipeline and more
  • Airtable — for portfolio management
  • Google Drive
  • Webflow — for our website
  • Zapier — but there’s only so much you can automate
  • 1Password — we’re pretty big on security
  • Calendly — but we’ve gone back and forth on that. I’m trying to spend more time with people who’ve invested in our fund, as well as the founders we invested in.
  • Twitter
  • Descript — for podcast transcriptions
  • Riverside — to record podcast episodes”

1947 Rise — Email, AngelList

“Regular LP updates, as well as my newsletter, have been my biggest engagement tool with LPs. I send the former out once a quarter, and the latter every few weeks. Luckily, I can also see all my LPs on my AngelList dashboard.”

Better Tomorrow Ventures — Carta, Affinity, Mailchimp, Aumni, Anduin

“We used Carta, Affinity, Mailchimp, Aumni for analytics, and Anduin to bring LPs in.  Fundraising is a bunch of chasing people down. Anduin’s a workflow tool. You can send people stuff and have people sign them all in one tool. Actually, several LPs told us that Anduin was the smoothest onboarding experience they’d ever had.”

“Mr. Huxley’s” Firm — Airtable, Notion, Whatsapp, Quickbooks, Google Drive

In closing

As I was writing this blogpost, a big part of me wanted a nice, easy linear narrative around LP construction. But I knew there wasn’t. In the many conversations that led to the above writing, it became quite evident there was no undisputed best way — no cure-all — to build an LP base.

Some believed in aiming high and never becoming oversubscribed. Others generated demand for their subsequent fund or was able to be judicious with their LPs by being oversubscribed.

Some built momentum by securing an anchor LP. Others started from individuals they knew the best.

Some didn’t budge on minimum check size. Others were flexible.

The list goes on and on. While there is no right answer, in knowing all of the above possibilities and strategies, I, and everyone who helped me make this blogpost a reality, hope you are armed with the knowledge to make the most informed decision for your fund. And to that, cheers!

Photo by Ivan Ragozin on Unsplash


Once again, and I cannot say this enough, a big, big thank you to Sarah Smith, Nichole Wischoff, Shiva Singh Sangwan, Vijen Patel, Eric Bahn, Paige Finn Doherty, Sheel Mohnot, Hunter Walk, Arjun Dev Arora, Steven Rosenblatt, and “Mr. Huxley” for our continuous back-and-forth’s, edits and of course, your insights.


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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.

The Two-Part Question That Differentiates Just Another GP From THE GP

singer, signal above the noise

The past 2 weeks brought me a whirlwind of conversations with emerging managers and LPs, catalyzed by the emerging LP playbook. And of the former, I’ve come across two main themes:

  1. Everyone — I kid you not… everyone — has top-tier VCs as their follow-on and/or their co-investors. What was once upon unique is no longer so.
  2. Eric was right. There’s an overabundance of the word “signal” in venture wonderland these days — to the point the word itself has lost its meaning. By definition, it should mean that is unique and stands above a sea of noise. For many investors, that means either investing in brand-name startups (i.e. SpaceX, Figma, etc.) or investing alongside brand-name investors. The latter, unfortunately, is also a product of the ecosystem as many LPs seek social proof about your investment thesis from others’ who have a proven track record. The former gets a bit sticky. A lot of these logos are either off-fund-thesis or came as a Series B syndicate investment (but the fund itself is investing in pre-seed or seed).

To piggyback on the above, the notion of signal is worth elaborating on, likely a vestigial appendage of the past two years.

Let me preface by saying that it takes a lot to get to conviction.

In 2020 and 2021, many investors’ calculus of startup signal boiled down to three things: great investors, great traction, and great team. And in that order. That is first and foremost what I see a lot of professionalizing investors do. I can’t entirely blame them since the ecosystem itself propagates the belief that if a Tier 1 VC jumps in, you’re more likely to get to a great exit. Or at the minimum, get a great mark-up to make your IRRs and TVPIs look better. On paper, of course.

But what I believe a lot of investors are missing is that… venture is a game that’s not about your batting average, but about the magnitude of the home runs you hit. You’ve heard it before, and you’ll continue to hear more of it. Unlike other financial services, VC is driven by the power law. 80% of your returns will be driven by 20% of your bets. That’s the 10,000 foot view. Let’s be honest. Most of us, myself included, don’t take that panoramic view every day or even every week. In fact, I see many emerging managers only take that view when they’re forced to. In other words, when they’re in fundraising mode.

For many professionalizing angels and syndicate leads, that becomes trying to string a narrative from seemingly disparate data points. Or at least, it seems that way.

As Asher Siddiqui told me, “[after] you look at their whole life and career history, and look at their thesis, if the thesis doesn’t make complete and perfect sense, then I don’t think this is a ‘great‘ fund manager. If it fits like a glove, then yes, they could be.”

The best GPs are disciplined even before they start fundraising. They focus on the thesis they want to raise on when they do. That’s not to say they don’t invest off-thesis every so often. But they don’t pitch their off-thesis angel or syndicate investments as part of their thesis-driven track record. But I digress.

In chasing signal for the sake of signal, when you hear of a hot deal every other day, many investors forget to be that belief capital for founders. I’m not saying that an investor should do so for every founder out there. But to pick a few, or even just one. One that they’re willing to take the swing before others do.

The signal is their own conviction in the founder.

The first half

Because of this progression, there’s been a new two-part question I really enjoy asking emerging GPs. The first half:

Which company in your portfolio you think is still underestimated?

Which company in your portfolio didn’t get the investor attention you expected but are still extremely bullish on their growth? And why do you still believe in them? What are other investors missing out on?

It’s not about track record or social proof here. It’s about the ability to recognize exceptional talent and articulate it clearly. Hopefully, a rose growing in concrete.

Well, in terms of the odds, you’re likely to be wrong. But that’s okay. You need to be willing to be wrong to achieve outlier success.

Fund I is often the proof-of-concept fund for the emerging managers I’ve talked to. They start by writing small checks, don’t lead rounds, and don’t fight for ownership targets. They claim to be extremely helpful and hands on. Then again, expectation often differs from reality, especially if they’ve never been so before (where LPs discover through reference checks). And because they’re writing smaller checks now, I’ve seen many implicitly hold off on developing a framework to get to conviction until Fund III. Whereas the best GPs start thinking about it early on.

You can think about it this way. As long as you’re benchmarking on signal via other investors, why should an LP back your thesis when they can back your “signal”?

For individuals and smaller family offices, they’ll still back you. What they’re buying is access, since they can’t afford nor have the relationship to be an LP in the “signals.” Larger LPs have the optionality to do so. And if you’re an emerging GP hoping to grow as a professional manager by having larger and larger funds, you eventually need to raise from large LPs. At least, until the SEC changes their 99 limit. And to do so, from larger LPs, means you need to bet where their existing portfolio has not bet before. Plus do it well.

The second half

If you haven’t already, a great way to build a referenceable track record is to sweat the details. Yes. The details matter. Nate Silver, one of the best poker players of our generation, said earlier this year, “you can’t just get the big things right in poker. You have to get the small things right too. It’s too competitive of a field right now.”

Though he said venture is different, I believe he’s half right. Most investors don’t sweat the small things. But investors should. Today, that’s how you stand out.

It might not have been true a decade ago, but now it is. Just last year, in 2021, there were 730 funds created. To put that number into perspective, on average, that literally means two firms closed every single day last year, including the holidays and weekends!

Capital has become a commodity. In 2021, speed was a differentiator. Clearly, in 2022, it is not. Today, it’s tough being a founder. If you’ve raised in the last two years, you’re considering extending your runway. That means having tough conversations to reduce your workforce, your benefits, or your salaries. If you haven’t raised, it’s a hard market to be raising in now. And so the differentiator today, is in two parts:

  1. Helping founders navigate these tough situations. In other words, being (proactively) helpful.
  2. And helping founders raise their next round. Mac Conwell recently shared a great thread on how powerful a founders’ network is to get funding. The same applies to an investors’ ability to help their portfolio raise capital. How liquid is your network? It’s not about who you know, but how well you know your friends downstream, and how can you get them over the activation energy to invest. Don’t get me wrong. There still needs to be a certain level of hustle from the founders themselves. But a great investor often steps in to reduce as much friction as we can in that process.

Both of which have long been the job description of being a VC. It’s in the small things. Jump on a 2AM call. Help your founders figure out the wording for a reduction-in-force. Fix the sales copy to better close leads.

There are 10-15 character-building moments in a founder’s journey where the moat they build around the business (as opposed to just the product) is not IP or early product traction, but rather from the lessons obtained from scar tissue.

It’s hard to predict looking through the windshield when these moments are, but quite obvious via the rearview mirror. And the best an investor can do is be there as much as he/she can. Albeit hard to do for every company in your portfolio, and that’s the truth. The wealth of information creates a poverty of attention. The larger your portfolio, the harder it is to be truly helpful to every single one. So focus on founders who need you, rather than those who will do great without you. Reputation is built in wartime and realized in peacetime.

So, the second part to the above question is:

What did you do for this company that no other investor or advisor did?

… where I’m looking for answers on how this investor went above the call of duty to help a company they believed in grow.

In closing

In summary,

  1. Which company in your portfolio you think is still underestimated?
  2. What did you do for this company that no other investor or advisor did?

This is by no means original, but heavily inspired by the recent conversations I’ve had, as well as helps me build my own framework for analysis. In parts, this question is a derivation to the check size to helpfulness ratio (CS:H). How helpful are you as an investor? When you say you’re founder-friendly, do you mean it?

Photo by Austin Neill 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!


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.

Three Mindsets To Being A Great Venture Investor

compass, path, direction, future

“Readily available quantitative information about the present is not gonna give you they key to the castle. […] If everyone has all the company data today and the means to massage it, how do you get a knowledge advantage?

“The answer is you have to either:

  1. Somehow do a better job of massaging the current data, which is challenging; or you have to
  2. Be better at making qualitative judgments; or you have to
  3. Be better at figuring out what the future holds.”

Those are the words of the great Howard Marks on a recent Acquired episode.

When most of us first learned economics — be it in high school or college, we learned of the Efficient Market Hypothesis. In short, if you had access to both public and private information, you would be capable of generating outsized returns that outperformed the market.

The truth is that reality differs quite a bit. And that’s especially in early-stage investing. Investors often make investment decisions with both public and private information at their disposal. There is admittedly still some level of asymmetric information, but that depends on deep of a diligence the investors do. Yet despite the closest thing to a strong efficiency, there’s still a large delta between the top half and bottom half of investors. The gap widens further when you compare with the top quartile. And the top decile. And the top percentile. Truly a power law distribution.

Massaging the data

I’m no data scientist, although I am obsessed with data. But there are people who are, and among them, people I deeply respect for their opinion.

There’s been this relentless, possibly ill-placed focus on growth (at all costs) over the last two years. Oftentimes, not even revenue growth, but for consumer startups, user growth.

I want to say I first heard of this from a Garry Tan video. The job of a founder pre-product-market fit (pre-PMF) is to catch lightning in a bottle. The job post-PMF is to keep lightning in that bottle. Two different problems. Many founders ended up focusing on or were forced to focus on (as a function of taking venture money) scale before they caught lightning in that bottle. They spent less time on A/B testing to find a global maximum, and ended up optimizing for a local maximum.

Today, or at least as of September 2022, there’s this ‘new’ focus on retention and profitability (at all costs). But there’s no one-size-fit-all for startups. As a founder, you need to find the metric that you should be optimizing for — a sign that your customers love your product. Whether it’s the percent of your customers that submit bug reports and still use your product or if you’re a marketplace, the percent of demand that converts to supply. Feel free to be creative. Massage your data, but it still has to make sense.

From a fund perspective, equally so, it’s not always about TVPI, IRR, and DPI, especially if you’re an emerging fund manager. Or in other words, a fund manager who has yet to hit product-market fit. You probably have an inflated total-value-to-paid-in capital (TVPI) — largely, if not completely dominated by unrealized return. The same is true for your IRR as well. In the past two years, with inflated rounds and fast deployment schedules, everyone seems like a genius. So many investors — angels, syndicate leads, and fund managers — found themselves with IRRs north of 70% for any vintage of investments 2019 and after. Although an institutional LP that I was chatting with recently discounts any vintage of startups 2017 and after.

So the North Star metrics here, for fund managers, isn’t IRR or TVPI. It’s other sets of data. I’ll give two examples. For a fund manager I chatted with a few weeks ago, it was the percent of his portfolio that raised follow-on capital within 24 months of his investment because it was more than twice as great as the some of the best venture firms out there. Another fund manager cited the number of his LPs who invested in his fund’s pro rata rights through SPVs.

Making qualitative judgments

In this camp, these are folks who have an extremely strong sense of logic and reasoning. When a founder has yet the data to back it up, these investors go back to first principles.

In my experience, these investors are incredible at asking questions, like how Doug Leone asks a founder for their strengths and weaknesses. But more than just asking questions, it’s also about building frameworks and knowing what to look for when you ask said questions.

For instance, every investor knows grit is an important trait in a founder. More than knowing at a high level that grit is important, what can you do to find it out? For me, it boils down to two things.

  1. Past performance. In other words, prior examples of excellence that they worked hard to get.
  2. Future predictors. I ask: Why does this problem keep you up at night? Or some variation. Why does this problem mean so much to you? Why are you obsessed? Are you obsessed? Why is this your life’s calling? And I’m not looking for a market-sizing exercise here.

While I don’t claim to hold all the truths in this world, nor can I yet count myself in the highest echelons of startup investing, the most I can do here is share my own qualitative frameworks for thinking:

Futurists

One of my favorite thought pieces on the internet is written by a legendary investor, Mike Maples Jr. of Floodgate fame. In it, he illuminates a concept he calls “backcasting.” To quote him:

“Legendary builders, therefore, must stand in the future and pull the present from the current reality to the future of their design. People living in the present usually dislike breakthrough ideas when they first hear about them. They have no context for what will be radically different in the future. So an important additional job of the builder is to persuade early like-minded people to join a new movement.”

Early-stage investors must have the same genetics: the ability to see the future for what it is before the rest of humanity can. And they back founders who are capable of willing the future into existence and create reality distortion fields, a term popularized by Bud Tribble when describing Steve Jobs.

When I first jumped into venture, one of the first VCs I met — in hindsight, a futurist — told me, “Some of the best ideas seem crazy at first.” A visionary investor is willing to take the time to detect brilliance in craziness. Paul Graham, in a piece titled Crazy New Ideas, proposed that it’s worth taking time to listen to someone who sounds crazy, but known to be otherwise, reasonable because more than anyone else, they know they sound crazy and are willing to risk their carefully-built reputation to do so.

For 10x founders and investors alike, the more you hear them out, the more they make sense. That said, if they start making less and less sense the more you listen, then your time is most likely better spent elsewhere.

In closing

As you may already know, a great early-stage investor requires a different skillset than a great public equities trader or a hedge fund investor. You’re more likely to work with qualitative data than quantitative data. Regardless of what archetype of a venture investor you are, you have to believe that we are capable of reaching a better future than the one we live in today. It is then a question of when and how, not if.

Of course, I don’t believe that these three archetypes are mutually exclusive. They are more representative of spectrums rather than definitive traits. Think of it more like an OCEAN personality test than a Myers-Briggs 16 personalities.

To sum it all, I like the way my friend describes venture investors: pragmatic optimists. Balance the realities of today with how great the future can be.

Photo by Jordan Madrid 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!


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.

#unfiltered #70 Conviction Comes From The Stories We Tell Ourselves

focus, conviction, motivation

On the second half of a late summer Friday, as I was overlooking the singed blades of the parched grass in our front yard, I found my good friend, Andrew, in my inbox. An inbox that was about to be empty from filing an eclectic collection of investor updates, food science analyses, tech articles, and my weekly subscription of Substack extraordinaires into my Read Later folder.

An email headline in boldface. All it would take would be two clicks. Two clicks to add to my party of internet writers I would be conversing with over a Saturday morning of roasted hojicha tea. Instead, I clicked once. Just once. And I’m glad I did.

Andrew started writing again. Pen to paper. Or rather, finger to keyboard. And that, that was worth celebrating. I, like many of his other friends, had been starved, deprived, relieved of his prose given his busy schedule. In it, he postulated the relationship between commitment and conviction.

“Commitment helps you stay on the path. Conviction is what calls you to the path in the first place.”

In sum, the pre-requisite for commitment is conviction. And so, it got me thinking about the source of conviction…

From inspiration

For decades, athletes have tried to break the 4-minute mile. According to British author John Bryant, since 1886. “It had become as much a psychological barrier as a physical one. And like an unconquerable mountain, the closer it was approached, the more daunting it seemed.”

But it wasn’t till May 6, 1954, did Roger Bannister break it with a time six-tenths under the mark. As soon as Bannister did it, 46 days later, another did. One year later, three runners broke the once elusive 4-minute barrier in one race.

The thing is, nothing technological had changed in the world when all these runners post-Bannister broke the four minutes. Nutrition hadn’t drastically improved. Neither was there drastic evolution in the technology of shoes. Yoram Wind and Colin Crook argues it was a mindset shift. The impossible was possible.

We see the same notion today in the world of emerging markets. In these markets, the first wave of unicorn founders is usually spearheaded by Harvard and Stanford grads building X for Latam or Y for Africa. For instance, both of Grab’s founders are HBS graduates. Gojek’s Nadiem is no exception. Nubank’s David Velez holds a similar Stanford GSB degree. So does Cabify’s Juan de Antonio. Rappi’s founders are also Stanford alumni. And the list goes on. They come with the Silicon Valley mindset in a market underestimated by not only the broader world but by the homegrown talent themselves. I like the way a Midwest founder-turned-investor once put it, “My mind is in Silicon Valley, but my feet are in the Midwest.” The same is true for this first wave.

And once they’ve proven it’s possible to reach unicorn status, the second wave follows quickly after.

Most people follow in the footsteps of our predecessors. Older siblings are the same for their younger siblings. Parents are that for their children. While I’m not a parent yet myself, I do aspire to be that for my children. Equally so, that’s why we need diverse representation in media, in positions of power, and in stories.

For many, conviction comes from examples to disprove the limitations of our own imagination.

From emotion

For a handful of others, conviction comes from a deep desire to prove or disprove.

There’s a superpower that comes with being underestimated. Reddit’s founders famously hung on the office walls the words of a Yahoo! exec who told them,  they were nothing but a “rounding error.”

When Michael Phelps’ eight gold medals in Beijing were on the line, their coach Bob used what the French team was boasting on the papers as motivation in the locker rooms. “The Americans? We’re going to smash them. That’s what we came here for.” And soon after, the world was blessed with one of the greatest races to date. A race of which the Americans — the underdogs — pulled a miraculous spectacle of conviction and resolve.

For founders, you need obsession, not just passion. Many of the best ones have a personal vendetta — a deep, unquenchable desire borne out of time spent in the idea maze. Every successful founder needs to perform 10-15 miracles in the startup to household name journey. Trials by fire that are meant to deter the fainthearted.

After chatting with a number of limited partners (LPs, folks who invest in venture funds) over the past two months, I’ve realized the thread of founder obsession continues here. That investor-market fit is not just a function of professional experience but also of life experience. Once again, a deep desire to change the world from personal frustrations and the hope that no one will ever have to go through what they went through.

In closing

Earlier this year, Reed Hastings shared a profound line with the graduating class, “[stories are] about harnessing the human spirit.” Conviction starts from the story we tell ourselves. The story itself is bound by the limitations of our own imagination. And conviction happens to be the belief that we can will our imagination into existence.

Michelangelo once said, “The sculpture is already complete within the marble block, before I start my work. It is already there, I just have to chisel away the superfluous material.” Commitment is the dedication to your conviction. A devotion to say no to distractions and yes to the person you want to be.

We live in a world filled with shiny objects. So, ask yourself, do you want what others want? Or what you truly want? Is your conviction inherited or innate?

I was listening to the latest episode of the All-In podcast, and David Friedberg echoed a similar notion for the greater human race, “What differentiates humans from all other species on Earth is our ability to tell stories. A story is a narrative about something that doesn’t exist. And by telling that narrative, you can create collective belief in something. And then that collective belief drives behavioral change and action in the world.”

Photo by Devin Avery on Unsplash


#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.


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


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.

DGQ 14: Why does the world need another venture fund?

rock, big rock, small rock

If you’ve been following me on Twitter recently, you might have noticed I’m working on a new blogpost for the emerging LP. One that I’m poorly equipped personally to talk about, but one that I know many LPs are not. Hence, I’ve had the opportunity to sit down with a number of LPs (limited partners – people who invest in venture funds) and talk about what is the big question GPs need to answer to get LP money, specifically institutional LP money.

And it boils down to this question:

Why does the world need another venture fund?

Most LPs think it doesn’t. And it is up to the GP to convince those LPs why they should exist. For most institutional LPs, even those who mean to back emerging managers, to invest in a new manager, they have to say no to an existing manager. While data has historically shown that new managers and small funds often outperform larger, more established funds on TVPI, DPI, and IRR, when institutional LPs invest in a Fund I, it’s not just about the Fund I, but also the Fund II and Fund III.

For those who reading who are unfamiliar with those terms, TVPI is the total value to paid-in capital. In other words, paper returns and the actual distributions you give back to LPs. DPI, distributions to paid-in capital, is just the latter – the actual returns LPs get in hand. IRR, internal rate of return, is the time value of money – how much an LP’s capital appreciates every year.

It’s a long-term relationship. Assuming that you fully deploy a fund every three years, that’s a 19-year relationship for three funds. Three years times three funds, with each fund lasting ten years long. If you ask for extensions, that could mean an even longer relationship.

But the thing is… it’s not just about returns. After all, when you’re fundraising for a Fund I, you don’t have much of a track record as a fund manager to go on. Even if you were an active angel and/or syndicate lead, most have about 5-6 years of deals they’ve invested in. Most of which have yet to realize.

So, instead, it’s about the story. A narrative backed by numbers of what you see that others don’t see. Many institutional LPs who invest in emerging managers also invest directly into startups. I’ve seen anywhere from 50-50 to 80-20 (startups to funds). And as such, they want to learn and grow and stay ahead of the market. They know that the top firms a decade ago were not the top firms that are around today. In fact, a16z was an emerging fund once upon a time back in 2009.

Of course, anecdotally, from about 15-ish conversations with institutional LPs, they still want a 4-5x TVPI in your angel investing track record as table stakes, before they even consider your story.

Over the past two years, capital has become quite a commodity. And different funds tackle the business of selling money differently. Some by speed. Others by betting on underestimated founders and markets.

The question still looms, despite the cyclical trends of the macroeconomy, what theses are going to generate outsized alphas?

And synonymously, why does the world need another venture fund?

Photo by Artem Kniaz on Unsplash


The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.


Subscribe to more of my shenaniganery. Warning: Not all of it will be worth the subscription. But hey, it’s free. But even if you don’t, you can always come back at your own pace.


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.

How Do Investors Think About Early Dilution On The Cap Table?

dilution water investment

A founder recently asked me how investors would perceive her going through two different accelerator programs. Specifically, what would investors think if she took dilutive capital from two investors who care about ownership targets, yet have similar, if not the same, value adds to her business?

How each type of investor thinks about dilution

It’s a great question. Unsurprisingly, a nuanced one as well.

Honestly, a “messy” cap table or early dilution is an excuse investors give when they’re not sold on you or the business. Investors regress to the “why this”, or otherwise known as, traction, when you haven’t convinced them on “why you.”

Investors want to be excited about you. They want to brag about you to their partnership, colleagues and friends. But if you don’t give them a strong reason to, they’re going to regress to what they know will return them capital. Predictability. And that comes in the form of traction. But I digress.

If Max Levchin or Phil Libin or Elon Musk or Justin Kan – pick your favorite serial entrepreneur with unicorn exits under their belt – wanted to raise for a new startup, no matter what it is or how early, people are gonna jump on the opportunity to regardless of how saturated the cap table is.

Let’s stand in the shoes of an investor for a second. Of which there are three main kinds of early investors.

  1. Angels
  2. Non-lead VCs and syndicate leads
  3. VCs who lead rounds

For individual angels, ownership targets don’t matter. They just want a piece of the action. In fact, multiple sources of signal and validation give them more confidence to invest. Especially if you’ve taken previous or current checks from your small handful of top tier VCs. These angels’ check sizes are negligible on the cap table, so they won’t end up crowding anyone else out.

On the other hand, notice how I bucketed non-lead VCs and syndicate leads into the same category. Why? These investors are writing bigger checks. They won’t price the round. And they move a lot faster if someone with a great track record is leading the round. Once again, ownership also doesn’t matter, but great co-investors do. As long as ownership targets don’t matter, the excuse of dilution is merely lip service. The story here is “I just need to get in the best deals, so I can raise my next fund from LPs.” Or “I need build my track record as an investor, so I can raise a fund one day.” I’m going to generalize here really quickly. While it doesn’t apply to every non-lead investor, it does apply to the vast majority. I dare say, 90% of them. These investors move on the combination of three levers:

  1. Great traction
  2. Great team,
  3. And great co-investors – the last of which is often the most important.

The more of the above levers you have as a founder, the faster you’ll get a check from the above individuals and institutions. Why do great co-investors matter so much? Outside of branding and social rapport, their investors – their LPs – also want to invest in these top deals led by these funds, but often can’t invest into these top-tier funds since everyone wants to get into a16z or Sequoia. In fact, for many of these top-tier funds, there’s a massive waitlist of LPs.

Finally, lead VCs. Ownership does matter. Really, this is the only audience you need to worry about when it comes to the topic of early dilution. While you as a founder should be dilution-preserving, sometimes, taking the capital (and subsequently, the dilution) is the best option. Maybe you really need something from an accelerator or an early investor that would be hard to get for you yourself. At that point, their capital becomes optimization capital. Early checks can get you from A to B faster, with less burn potentially, and with less detours.

So, the question you have to figure out if you take subsequent capital injections is that each time you dilute the cap table, did you reach an important milestone? What’s worrying is if you keep diluting your cap table without making meaningful progress each time. Think in the framework of milestone-based financing. Raise what you need, while giving you and your team an appropriate margin of error.

In closing

As a footnote, it’s also important to consider how much equity you as the founder will have left upon exit. If you’re going through large amounts of early dilution, you’re going to have very little upside unless you go through a massive exit. Unlike investors who invest in many businesses and have diversified their risk appetite, you, the founder, have put all your eggs in one basket. So if you care about the upside, you want to reduce dilution unless there is an absolute necessity to raise capital.

Photo by Lucas Benjamin 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!

No One Talks About Selling

Seemingly, everyone these days – from Twitter to podcasts to blogposts (including mine) – talk about buying and investing in startups. What are best practices for investment theses? How do I pick the best companies to invest in? Conversely, how do I get picked or get allocation into hot startups? But people rarely seem to be talking about selling positions. So, if you know me, I hit up two of the smartest people I know – one early-stage, the other growth-stage. Both of whom might be familiar faces on this blog. So I asked them:

How do you think about selling a position? How much does DPI matter for your investors?

The below insights include minor edits for clarity.

The notice that you’ve all seen a million times

None of this is investment advice. This content is for informational purposes only, and should not be relied upon as legal, business, investment, or tax advice. Please consult your own adviser before making any investments.

Shawn Merani (Parade Ventures)

Shawn was instrumental in my early career growth in venture. When I met him years ago, he was still running Flight Ventures, where he wrote early checks into Dollar Shave Club and Cruise Automation and was one of the first syndicates on AngelList. There he led a network-based model of syndicate leads, which I’ve heard been described by others as a “venture partner program on steroids.” Now he’s the solo GP at Parade Ventures, a seed stage venture fund investing in enterprise-themed companies.

“I would preface all of this with the fact we have never fully exited a position before a traditional liquidity event, but more so, have managed our position given the duration of our ownership and to generate returns for our LPs and manage risk. 

“We talk to founders all the time, and foster a relationship that grows. When I was writing check sizes for 1-5% of ownership, my engagement then is very different from my engagement with founders now, where we take more concentrated bets.

“When it comes to selling, it’s about influence and information. The larger our ownership, the more information we have access to. And if a company is doing well, we don’t think about selling. In fact, it’s the exact opposite; we buy more. If things are working, we take our pro rata. In some cases, we take more than my ownership target. And founders are willing since we’ve been helping them from the beginning. We know when there’s going to be a 3-4x uptick every 12-18 months. Compounding is powerful.

“Our investors back the fund because they trust us. They don’t talk to the founders as often as we do. They trust our decision when we say we should buy more or keep our shares. There are two ways to talk about DPI:

1. Making money for your current investors, and
2. Telling the story.

“Selling is really a case-by-case scenario, and it really depends on my relationship with the founder. All the equity in which I sold so far has been before Parade. But if we know the company is doing well, we buy more. There are also holding periods to consider under QSBS, which has huge tax benefits.”

For those that are unfamiliar with the terminology, DPI means distributions to paid-in capital. Effectively, how much money you actually return to your investors versus “paper returns”. QSBS, or qualified small business stock, tax exemption allows investors in qualified businesses to avoid 100% of the capital gains tax incurred if they hold their stock for more than 5 years.

Ratan Singh (Fort Ross Ventures)

I posed the same question to someone I’ve been a huge fan of the day I met him – Ratan Singh, Partner at Fort Ross Ventures. He’s an investor in some of the most recognizable businesses today, including the likes of Rescale and Clearcover, as well as holds board seats at Blueshift and Ridecell. You may remember Ratan from a previous essay about speed as a competitive advantage for investors. And you’ll likely see him a lot more on this blog. He summed it up best in our chat when he said, “There are two reasons why an investor needs to care about DPI: time horizon and fund strategy.” Both of which are variables, not constants, between early- and growth-stage investments.

“The true metric at the end of the day is DPI. DPI is turning in money to your investors. And there are two reasons why an investor needs to care about DPI: time horizon and fund strategy.

“Let’s start with time horizon. For a seed stage fund, as you get close to the end of your fund cycle, that’s when DPI matters. What type of vintage is the fund in? In 2021, it’s going to be the 2010 and 2011 funds.

“For the majority of the time, you want to ride your winners. At the end of your time horizon, ask for a one- to two-year extension. Usually LPs want more money or their shares distributed. They’ve already waited 10 years. Two more won’t make a difference, especially if you have some big fund returners in the making.

“For fund strategy, did you meet the objectives for your LPs already? If you have, and you want to sell some of your winnable deals in your portfolio to help raise your Fund II because those are the same LPs that would re-up in your next fund, then you might consider selling.

“The worst reason to sell is that you want to take the wins you currently have since you think the market is overvalued. ‘I’m at the peak.’ Or ‘I want to take chips off the table because there’s something bad that will happen, but that is very hard to predict.’

“There were a bunch of funds at the beginning of this year that sold their entire positions. They were desperate to lock in a win. They sold because they thought the market was at the top. And, they were wrong. I’m against it. Selling early doesn’t fully realize the strategy you have put forth. For us, at the growth stage, we shoot for 48 months to an exit. If it takes longer, did we underwrite it wrong? But even if it does, the case may be that the company is growing a little slower than expected.

“At the early stage, all funds will say 2 to 3x cash-on-cash in the LP presentation. Most funds return 1 to 1.5x, on average, with most funds total DPI at 1.2 to 1.5x, which barely returns the fund. Before your time horizon, everyone likes to cite unrealized gains and mark ups because TVPI’s all they have.

“DPI matters most for funds in the top quartile – the top returners, funds with more than $500 million, or nowadays, $1 billion mega-funds. For the bottom majority of funds, early DPI won’t matter. They would be limiting their upside.

venture returns
Author’s Note: Notice that 65% of financings lost money for their investors.
Source: Correlation Ventures

“The new interesting commentary is that – where the job is getting harder – a lot of crossover funds are making binary bets. Finding the one deal that’s the next Salesforce – the next industry-defining company. And putting a lot of capital to find that one or two companies. Tiger and Coatue, still maintain that 10-12% IRR, but spend a lot to find the company that’ll be the next Databricks. Every generation has their industry-defining companies. And, they’re willing to lose it all to find that one.

“You usually don’t see this at the growth stage. It’s bad for innovation. Everyone is trying to find investments that are scaling. 1000 investments in the past year became unicorns. And there are 3000+ unicorns. Yet, the top five to seven companies are still undercapitalized.”

In closing

As we closed the selling part of our conversation, Ratan shared a great quote from an Economist article:

“Flush with cash amid a deal frenzy, what is the industry to do? One option would be to liquidate portfolios, that is, to sell more assets than it buys, in effect trying to cash in some chips when prices are high. As yet, however, this does not seem to be happening. Take the figures for three big managers, Blackstone, Carlyle and KKR. So far this year for every $1 of assets, in aggregate, that they have sold, they have bought $1.30. Although Carlyle is being more cautious than the other two firms, these figures indicate that the industry overall thinks the good times will roll on.”

In fairness, as the saying goes, the high risk, high reward. Data does show that the funds with the greatest track records have more deals that lose money than those make them more money than they invested.

Interestingly enough, there’s also a huge differential between the world’s most valuable and most funded startups. According to Founder Collective, “the most valuable companies raised half as much capital and produced nearly 4X the value!” All of which echo Ratan’s words. “The top five to seven companies are still undercapitalized.”

Source: Founder Collective

The public often looks towards invested capital as a proxy of startup performance. But the data suggests that isn’t the case. In the words of the team at Founder Collective, “capital has no insights.” One of my favorite lines from Ashmeet Sidana of Engineering Capital frames it is still: “A company’s success makes a VC’s reputation; a VC’s success does not make a company’s reputation.”

But when DPI boils down to selling on multiples at the end of the day, I often reference Samir Kaji‘s tweet on the return hurdles expected of different stages of investors. As you might guess, the return expectations of each type of fund varies based on fund strategy.

As all things in the world, exiting is just as nuanced and complicated as entering. Hopefully, the above insights will be another set of tools for your toolkit.

If this essay has inspired more questions, here are some further reading materials, courtesy of Ratan:

Photo by Visual Stories || Micheile on Unsplash


Thank you Shawn and Ratan for reading over early drafts.


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Think like an LP to Get a Job in VC

I want to preface this piece by first saying, though I have LP (limited partner) friends, I’ve never been an LP. So take everything with a grain of salt. For that matter, even I have been an LP, still take this with a grain of salt. After all it’s just my one perspective on the world. Nevertheless, I hope this perspective helps to provide some context around the venture space. As it did for me.

For years, I’ve recommended my friends who were looking at startup job opportunities to think like a VC. And having chatted a number of firms over the years about scout, associate/analyst, venture partner roles, I’ve come to a new revelation. Or rather one that I’ve practiced for a while, but haven’t connected the dots until recently.

When you’re looking for VC job opportunities, think like an LP. I’ve written about the LP calculus a few times before, like:

Here are some questions I usually consider:

  • How have you thought about your own differentiation that gets you access to some of the uniquely fund-defining opportunities you have?
  • What are the startups in your anti-portfolio? And what have you learned since from them?
  • [if their funds are wildly different in fund size (i.e. Fund I – $20M, Fund II – $100M)] How do you think about fund strategy now versus Fund [t_now-1]?
    • For context, usually each subsequent fund doubles in size. i.e. Fund I $20M, Fund II $40-50M, Fund III $80-100M
  • [If they have fund advisors, EIRs, and/or scouts] How do you pick advisors? What is your mental model for picking scouts?
    • Or one of my favorite phrasings: How do you differentiate the good from the great [advisors/scouts]?

Over the weekend, my friend sent me a great podcast for me to unwind. In it, I found an unlikely hero soundbite. “Your library holds a lot of value that you may not know until the story arrives. […] No one’s selling characters ’cause they’re one story away from this character becoming a hit.” While its context is related to why Marvel won’t sell any of its superheroes, Alex Segura‘s, co-president of Archie Comic Publications, anecdote proves just as insightful to the world of venture.

Discovering first-time early-stage founders is hard. The same is true for finding the next killer GP or venture firm. AngelList’s Rolling Funds are democratizing access to capital, lowering the barrier to entry for emerging fund managers. And really the success of a fund is determined by its MOIC – multiple on invested capital. 5x and up would be ideal. And that, like I mentioned in my last blogpost, boils down to the fund’s top one or two winners. Loosely analogized to a fund’s unicorn rate (percent of portfolio that are unicorns). In other words, the “one [investment] away from this [fund] becoming a hit.”

To see if a fund can consistently find those stories boils down to its systems. Often times, you’re joining a fund that has yet to have a runaway success. Or a fund that has a fund returner. So, instead, you’re looking at their thesis and if their thesis allows them to be:

  1. The best dollar on the cap table of a startup in their scope
  2. Forward-thinking enough to see where the market is heading, rather than where it’s been
    • And by definition of being forward-thinking, taking bets/risks that few other VCs would, yet calculated enough to make logical sense given the trajectory of the market. In other words, is the thesis grounded on first principles, yet able to capture their second-order effects?
    • That, in turn, requires you as a VC applicant to have decent literacy in the market the firm is betting in.

As James Clear, author of Atomic Habits, wrote, “You do not rise to the level of your goals. You fall to the level of your systems.” What are their mental models? Fund strategy? How do they think about portfolio construction? About capital allocation? And more importantly, time allocation?

If you’re looking to learn more about GP-LP dynamics, I highly recommend Samir Kaji’s Venture Unlocked podcast and Notation Capital’s Origins podcast.

Photo by Micheile Henderson on Unsplash


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Mega vs Micro Funds – Where is the money going in the private markets?

markets, mega vs microfunds
Photo by William Felker on Unsplash

One of my buddies and his team recently successfully raised their Fund I, luckily before this recent downturn. Moreover, their fund is geared towards investments into frontier tech. And the Curious George in me couldn’t help but ask about his findings and learnings. In the scope of mega versus micro-funds, our conversation also spiraled into:

  • the current state of private markets,
  • VC-LP dynamics,
  • and, operators-turned VCs.

Here’s a snapshot of our conversation, which could act as a cognitive passport for newly-minted and aspiring VCs. For the purpose of this blog, I’ll call him Noah.

The Snapshot

David: How do you think the private markets will change in this pandemic?

Noah: In a way starting a fund is a lot like starting a company. It’s definitely a humbling process to be on the ‘other side’ of the table and feel what it’s like to be an ‘entrepreneur’ and fundraise.

Yeah the impact on the private market side is something i’m trying to figure out yet. I think it’s still a little early to denote the true extent of the impact. But nonetheless, in the short term, funding activity is bound to go down, people are speculating the duration of this event and waiting for prices to come down. We’re lucky to have closed some money before this happened but it’ll be extremely tricky for the next wave of new fund managers to raise their funds.

It’ll be an especially rough time for founders especially if it goes on for long enough, most VCs will probably try to cut losses by dedicating their attention to portfolios that have the highest chance of survival. This crisis is also different in the sense that it’s a virus which prevents people from regrouping quickly if it carries on.

David: And it’s partly due to a recent function of LPs under-allocating towards the VC asset class as a whole, with longer fund cycles (10 years [6-7 years now] + 2-year extensions). Before all this, the market had been performing rather well in the past few years (a solid 17-18% return YoY on the public markets, or these self-imposed liquidity events, versus venture where only the top quartile of VCs make better than market return). I believe the 2018 number for the top quartile annual IRR was 24.98%, which is, what, 3x in 5 years, but even then, its not enough to convince many LPs.

Although you have the rise in a new sort of private investor in both the secondary markets, as well as VC-LP functions, where firms LPs either invest directly, or VCs are now investing in other micro-funds, like Sapphire. With VCs writing more discovery checks, and so many recent exits in tech, syndicates, via SPVs (special purpose vehicles), has helped them develop relationships with founders early on and relatively no strings attached.

Noah: I think one metric that really stands out that everyone is thinking about is in terms of liquidity. Not only are companies staying private for longer, more and more new alternative asset classes are rising. Interestingly enough, a lot of the endowments or larger institutions we’ve talked to are over allocated in venture. For example, Duke has nearly 1/3 of their money allocated to VCs. One obvious way that VCs are tackling this is in the secondaries market, selling off equity earlier and earlier, so lower potential return profile but LPs generally love early indications of a good DPI.

And yep, microfunds is definitely a big trend as well. It’s simply not sustainable for half a bill/billion dollar early stage funds to exist. Some of the returns of these mega funds have been made public and they’re not looking too great, even if it’s still early for them. On the flip side, smaller funds are a lot easier to return and generally where the best performing vehicles can be found. Moreover, the traditional endowments and institutions have locked in to the Sequoias and Andreessens already, so new FoFs (fund of funds) and relatively newer endowments are always looking for who are the next best alternatives. It just so happened that we’re also seeing a wave of ex-operators coming into the world of VCs and starting new funds. They might not have the acumen to build a long-standing mega fund yet, but their technical expertise makes them a good candidate for more verticalized funds.

David: I totally agree with your sentiment that operators should go do specialized funds, that could be vertically aligned, or could be functionally aligned (i.e. marketing, growth, dev, design, etc.). I’ve had this long standing belief, and let me know what you think. If you’re a great VC, run a mega fund. But if you’re a good-to-okay VC, run a micro fund or an alternative funding vehicle.

As someone who’s good-to-okay, it’s more important to (1) hedge your bets, aka diversify your portfolio, and (2) collect data. Most newly-minted VCs don’t have the experience, like you said, on the other side of the table. Just because you’ve been a good student doesn’t mean you’ll be a good teacher. As someone starting off or just don’t have a stable track record for doing well (aka one shot wonders or the lagging 75% if not more, of the industry), you gotta collect data, to do better cohort/portfolio/deal flow analysis.

Whereas if you’re a great VC, you need the capital to commit to the best investments of your portfolio. So megafunds, plus growth funds, make sense. Although, admittedly great VCs are far and few between.

Noah: My two cents is that the trend of larger and larger fund sizes is ultimately the result of VCs becoming too competitive. It’s no longer enough that VCs have a platform team to help support portfolio companies because more and more other VCs are amassing large support teams too. Therefore as you mentioned, the true way for them to stand out is to have a multi-billion dollar fund that spans across multiple stages. So unlike an early stage fund that can only guarantee committing maybe up to, let’s say, $10MM in capital during their seed and series A, these new beasts can support you in the growth rounds as well, all the way to IPO, and more and more VCs are doing so.

The problem is that this is a recent trend that happened within the past decade, and it’s still quite early to judge the capabilities of some of these new mega funds and whether they’re qualified to manage such a large fund. Nonetheless, you do still see that some of the best funds out there are very disciplined in keeping a consistent fund size (e.g. USV, Benchmark, First round, etc.) simply because it’s so much harder to return a billion dollar fund versus a $250MM vehicle. Microfunds is another interesting trend. On one hand a lot of these newly-minted VCs simply don’t have the capability to raise a >$100MM+ fund in the first place. But there are also cases where the GPs are more than capable but still choose to keep it at a <$100MM vehicle. I’m guessing a lot has to do with the competitive environment we’re in nowadays. When you don’t have as high ownership targets because of your smaller fund, you’re more flexible with minority stakes and can thus co-invest and get into better deals.

What does this mean for founders?

In these trying times, the public discourse around venture financing has been that there’s still quite a bit of capital that has yet to be deployed and that investors are still looking to invest. Yet it is neither entirely true nor entirely false. There are still financings going on today. Admittedly, most of these started their conversations 2-3 months ago.

The goal is cash preservation over growth for many verticals and companies, and it’s no less true for private companies. In that theme, most investors’ first foremost focus is the wellbeing of their portfolio. And because of that priority, many investors are slowing their investing schedule for now. This is especially true for megafunds, where, as ‘Noah’ mentioned, requires much more to return the fund, much less make a profit.

On the flip side, I’ve seen smaller funds and angel syndicates still actively deploying in this climate. I’ve also heard concerns where this pandemic and downturn is going to affect their fundraising schedule for Fund II and Fund III, so they’re pressured with making bets now from their LPs.

Anecdotally, it shouldn’t be harder to raise funding now than before. Some of the greatest companies came out of the past few downturns (2000 and ’08). A caveat would be if you overvalued in a previous round and are still looking to maintain the valuation trajectory (up round over down round).

So keep hacking! Measure well! And stay safe!


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