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.


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.

#unfiltered #75 Why I Write Long Form Blogposts

typewriter, blog, write

This past Wednesday, I was having lunch with an artist-turned-VC. And as you might imagine, we had to cover every topic at the intersection of art and startup investing. But of all the ground we covered, one stood out — content creation.

She’s on the Gram, LinkedIn, and everything in between. (Although surprisingly not on Twitter.) But to help her focus, she uninstalls those apps on her phone. Otherwise, she says she’ll end up “doomscrolling.” I get it. In fact, many of my friends and colleagues have shared similar things as well. But…

I’m weird. At least among my friend group, I’m really weird. I’m terrible at social media. I’m an 80-year old stuck in a 27-year old body. At least on the social media front. I find it so hard to keep my attention on social. In fact, I schedule ten minutes three times a week to hold myself accountable to be on LinkedIn and Twitter.

So, when it came to sharing my thoughts and learnings publicly, it was a pretty easy decision. Of course, I eventually came to self-rationalize it as the ability to own my own piece of virtual real estate, but there are three more reasons I chose blogging rather than tweeting or social posting.

1. I write to think

I’ve written about this before so I won’t elaborate in length on my own rationale here, but share a few examples of others also holding it in high regard.

There’s only so much you can flush out in just 280 characters, or over any short post. And while some of my thoughts fully flushed out may only be that long or less, not having that restriction gives me peace of mind to not hold back.

One of my favorite George Orwell lines happens to be: “If people cannot write well, they cannot think well. And if they cannot think well, others will do their thinking for them.”

On that same wavelength on writing, Jeff Bezos makes Amazon execs write six-page memos. In most companies, team members often resort to PowerPoint presentations. Take anywhere between five and ten slides. Maybe less, maybe more. It’s much less thought out than a six-page dissertation. As Bezos says, “The reason writing a ‘good’ four page memo is harder than ‘writing’ a 20-page PowerPoint is because the narrative structure of a good memo forces better thought and better understanding of what’s more important than what.”

Equally so, it’s the same reason the best investors write memos for their investment decisions. My favorite public ones are Bessemer’s, which encapsulates much of their thinking at the time in amber. Turner Novak also turned his ability to write great memos to eventually raising his fund, Banana Capital. And the great Brian Rumao writes memos not just pre-investment, but also in his post-mortems where he gathers his learnings.

While I won’t go as far as to comparing myself to the afore-mentioned, I do find great pleasure and great learning from putting words on paper.

2. Longer feedback loop

My writing is more often a form of self-expression, self-curiosity, and self-discovery. So, unlike a product manager or founder who’s relentlessly testing and iterating on feedback, I enjoy longer feedback loops. I may start another content engine at some point that is for a particular audience, focused on feedback and iteration. But this humble piece of virtual estate will stay me. With no algorithm conditioning my attention span and yearn for external validation. That’s not to say I won’t ever (or have not ever) written things that you my awesome readers want, but it is only at the intersection of what you want and the what I enjoy writing about and asking others about that mint content here.

I also spend a lot of time thinking about audience capture, a term Gurwinder brought to my attention in an essay he wrote about Nikocado Avocado, which I also touched on in an essay I wrote near the end of last year.

I’m reminded by something Gurwinder wrote a few months ago about the perils of audience capture. In it, he shares the story of Nikocado Avocado, who lost himself to his audience, in a section of that essay he calls: The Man Who Ate Himself. He also shares one line that I find quite profound:

“We often talk of ‘captive audiences,’ regarding the performer as hypnotizing their viewers. But just as often, it’s the viewers hypnotizing the performer. This disease, of which Perry is but one victim of many, is known as audience capture, and it’s essential to understanding influencers in particular and the online ecosystem in general.”

3. The impermanence of social media

Most things on social media are ephemeral in nature. It’s designed to capture the moment, but not chronicle the moments. On Twitter, you can only pin one tweet. On Instagram, you can pin three. And on LinkedIn, only three are visible on the featured carousel, and include, five max before it takes you down another layer of friction to discover more.

There’s a level of impermanence which makes thoughts feel whimsical rather than evergreen. To use a phrase I recently heard Tim Ferriss use, the “durability of the signal seems to wane so quickly.” And that made my thoughts feel cheap.

That’s not to say every post I write has their weight in gold, but the searchability and the evergreen nature of my favorite blogposts (saved in my “About” tab) are the reasons I keep most of my thoughts here.

Photo by Fiona Murray 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!


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.

To Bridge or Not to Bridge

bridge

In the wonderful world of venture, an investor takes a different kind of bet with each stage as a function of industry. For instance, a pre-seed SaaS product, it’s a distribution risk. Can this founder sell this product to others? In general, the angel or pre-seed round is often a founder bet. Can this founder or founding team pull off their vision? And subsequently, if they’re able to achieve their milestones in the funding window, will those milestones excite downstream capital?

One of the greatest byproducts in starting my career in venture as a scout — sending seed and Series A deals to those respective investors — was that I learned what archetypes of deals interested them. And what didn’t. As I moved even earlier in the funnel, so, pre-seed and seed, I could help founders and their teams set themselves up for the subsequent round.

Admittedly, that became a bit harder to do in the hoorah of 2020 and 2021 — with insane multiples and raises coming together as a function of FOMO.

When looking at the present day, mid-February of 2023, one in three or four deals in my inbox is a company raising a bridge. The bet here is an execution bet. Now before I get into the questions I consider when a founder pitches a bridge fundraise, I think it’ll be helpful to consider bridge rounds as a function of good and bad markets. And why they make more sense in a bull market, for better or worse, than in a bear market.

Bridge and venture debt

In a bull market, bridge rounds — or preemptive rounds, pick your nomenclature — and pay-to-play rounds make sense. The promise of capital within six months is extremely likely. Interest rates are low enough, where equity instruments have greater return potential than debt instruments. In a similar way, the same can be said for the premise behind venture debt. Venture debt (I am but an armchair expert at best, but have been lucky to query some of the best) is debt that is issued with the expectation of another round. At the same time, the warning label here is in a few-fold:

  • Many VCs prefer not to have investors higher than them on preference stack.
  • Subsequent equity raises are used to pay back venture debt first.
  • You have a 36-month repayment period usually, after if you decide to use the capital within the first 12 months or not.
  • There are usually warrants that ask for additional ownership in the company on top of the loan.

But I digress. In a bear market, bridge markets make less sense for an investor. Bridge rounds usually occur when teams miss expectations. They’ve missed milestones. Their burn rate was higher than expected. And their runway is naught but less than a year. It’s way the most common recommendation VCs gave their portfolio companies in 2022 was have at least a 24-month runway. You have more wiggle room to prove assumptions and get to an inflection point.

In a bull market, missing expectations is almost impossible. Sky high valuation multiples and funding rounds made capital cheap. When capital’s cheap, founders are more likely to spend with less discipline than otherwise. Moreover, consumers felt richer. Their net worth appreciated in a good economy. Interest rates lag inflationary signs. And the money is out of the pocket before it has time to warm up. Consumers also not only spend more, but they invest more. Companies saw greater revenue numbers and market cap growth, leading to more liberal spending habits. Greater market budgets to acquire customers. That spending led to high burn multiples.

This all led to a virtuous flywheel, that though growth and revenue numbers hit, the cost to get there also exponentially grew. The quality of businesses declined, as consumers and companies got used to the spending habits of the good times. Those same habits, unfortunately, don’t work in a recessionary market. And when founders are unable to part with their multiple in a boom market, and for many, the spend during that same market, they go to raise a bridge round instead of offering new equity, hoping they’ll, in some way, “make it work.” And yes, that’s the exact wording some founders used.

If investors have the chance to place new shots on goal, a lot of investors today are willing to bear the opportunity cost of passing on a bridge round.

Inflection points and lack thereof

Each new round is raised on the assumption your company is at an inflection point. Right as your second derivative shifts from negative to positive. To some businesses, that’s a market inflection. A (lucky) black swan event. A technological release. Or a regulatory easing. To others, it’s a traction inflection. Users just love your product. And to another cohort, not mutually exclusive to the afore-two inflections, is an insight inflection. You’ve learned something that’s going to catapult you so much further. For Duolingo in 2012, it’s the realization of going mobile. For Zynga, in 2010, it was its partnership with a rising class of platform usage, social media, namely Facebook.

On the other hand, for Airbnb, in 2011, its major competitor abroad, Wimdu raised $90 million to focus on its European expansion. That meant if Airbnb didn’t expand outside of the US, they would lose access to a whole market of Europeans but also Americans whose vacation destinations were one of the seven continents. To the Airbnb team, in the words of Jonathan Golden, their first PM, it was the realization that “marketplaces are normally winner-take-all markets” and “when competition comes after you, move ridiculously fast.” And they did.

Bridge rounds often don’t carry that same drive or momentum. It’s not raised at an inflection point, but rather in efforts to get to one. Usually it’s not proving a new assumption but last round’s assumptions. As I mentioned at the top, it’s an execution bet. And as such, it begs the question: How much conviction do I have that a founder is going to be a great steward of capital?

Fortunately or unfortunately, unlike most other early-stage round constructions, there are multiple data points. Have they used capital to date efficiently and effectively? If so, do I believe this founder will 10x their KPIs within this funding window?

Usually the funding window I allude to is 12 to 18 months. In the scenario of a bridge, that timeline becomes six months. The expectations are less forgiving and more aggressive. What are you building to in half a year? Do you have the discipline to execute on that goal? Does your track record corroborate? Do you have a detailed plan to get there?

In closing

IVP’s Tom Loverro recently shared, “A half measure is usually something a management team lands on because it’s easy. If a decision is easy, it’s probably a half measure. If it’s hard, if it’s really damn hard… if it’s controversial, you’re probably doing enough of it. The other thing is a half measure often doesn’t have an end result or goal in mind. If you have a really specific goal, and implementing that goal is difficult, that’s probably doing your job. That’s probably what’s necessary.”

A bridge round, more often than not, is a half measure.

He goes on to say, “If it’s a good company, give them a lot of capital. If not, zero.”

This past week, I chatted with three institutional LPs, and three more venture investors about this topic. In five out of six conversations, one phrase made its appearance. “Don’t put good money after bad.” And while anecdotal, all six — every single one having participated in bridge rounds at some point in their investing career — concluded money was better spent in new investments than in bridge rounds. The caveat from these conversations was that it may work if you are either leading the round or setting the terms. Then again, that’s favorable for an investor, and may not be as much for the founders.

That said, I’m sure there’ll still be great companies raising bridges. But who knows… I await the day, not just in outliers, that we see bridge rounds trend otherwise. For that to happen, I agree with many of my colleagues that we need to see a lot more discipline from the average founder.

Photo by Terrance Raper on Unsplash


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


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

#unfiltered #74 What If Events Were Story Arcs?

castle, story, boat

“Somewhere along the line is a voice deep within you that tells you exactly who you are; you just have to have the courage to do that. That’s what the journey of the hero is all about. You’re born into a world where you don’t fit in. You answer the call to adventure. And you deny the call. Then at some point you then set out on your path. You slay dragons, and you do all of that. At some point, you come face-to-face with not a god, but yourself. Somewhere along the line, you get it — your A-ha moment. Your elixir. And you go back to your ordinary world and share it with others. I think that’s the journey. I think that’s the privilege of being absolutely who you are — belonging to yourself and being brave.”

That’s the arc of every great story in the words of Viola Davis on one of my new favorite interviews with Sean Evans, where she shares the secret to the hero’s journey.

In the world post-pandemic, people crave connection. A desire to go from URL to IRL. Everyone lost those years. Something everyone from a first grader to a college student to a young professional entering the workforce to a retiree could relate to. And in 2021, there was a re-emergence of events. Well-intentioned and well-founded. We had conferences, coffee chats, happy hours, fireside chats, oh, so many happy hours, panels, tech weeks, and… did I mention happy hours?

Most events out there are a time and a place for a collection of people. They’re static points in time. Not even counting the full spectrum of event planners, many of the best event planners spend tons of times on what makes events special, but change more about the small bells and whistles of an event than the overall flow. There are very few who take leaps of faith. Even less true for the vast majority of events, where events feel more of an afterthought than something that is designed to start or end a chapter in your life.

As such, everyone found themselves left with a goodie bag including a surplus of events, a lack of focus and attention, and a lollipop of exhaustion.

So, I had a thought last year, greatly inspired by my team at On Deck Angels. Instead of trying to host an event a month, what would need to change if we could only do one event a year? What would we have to do? Hell, extrapolating further, what if we only did one event every two years? Three years? Every Olympic arc? Which led to the thinking around, what do we need to do to make this the most memorable event that anyone has ever been to.

You see, I’ve hosted and co-hosted small and large-scale social experiments, but it was always for an audience who proactively and voluntarily signed up for. They were willing to do things outside the ordinary. But could I apply the same learnings to events for really, busy people who crave intellectual challenges, and who have been to so many events, they might be jaded?

So, below was and continues to be my collection of governing thoughts around answering that question, which will only grow and refine this year. In the theme of my blogpost last week, the below may be messy. Disorganized. Chaotic, even. Hope not, but possible. You’ve been warned. But I do hope that you might find at least one of the below frameworks useful.

Metrics for success

Every event needs a North Star. When planning the Angel Forum, as well as future events, below are mine.

  1. Attendees go on a hero’s journey, revisiting Viola Davis’ words above. In other words, character development. The event should create opportunities for growth within the event itself.
  2. Every attendee continues to and is motivated to build friendships (as opposed to networking and purely transactional connection) after the event. If the event itself is the only reason for people to connect, but it does not give people incentive to after, it’s a failure (in my books).

For now, that means, not only the speakers and the presenters need to be curated, but also each and every person on the guest list. I have yet to figure out how to customize such experiences at scale, where each person has wildly different goals.

Narrative frameworks I use for events

To dig a level deeper, here are my frameworks for execution:

  1. Surprise and suspense — Surprise is when you relay information that the audience does not expect. Suspense is when you relay information that the audience is expecting, but does not know when it’ll drop. Suspense is how you keep attention. It raises expectation, but knowing when to deliver the news helps with creating a reality that meets or beats expectation. Surprise is, on the other hand, purely for creating alphas in this expectation-versus-reality model. It’s the main driver for overdelivering on a seemingly smaller, but still powerful promise. To do so, I find George Loewenstein’s 1994 paper on the psychology of curiosity super helpful. More on how the five triggers to curiosity influenced my thinking here.
  2. Candy versus the meal — A Malcolm Gladwell framework. Effectively, how people think and what people actually talk about are quite different. Candy is what people talk about. For example, if I were to talk about the recent Avatar movie, I’d talk about how amazing the motion capture and the CGI was. And in doing so, I’ve spoiled nothing. It tells you nothing about the plot, but it’s exciting to talk about. On the other hand, the meal is how people think. It’s the whole package, the whole story. The meal has to be well-worth the visit, but the candy is what gets people excited. More on that in a previous essay I wrote here.
  3. The audience must understand the rules of magic — This is a combination of the thoughts of Malcolm Gladwell‘s framework around tools and Brandon Sanderson’s three laws of magical systems. Give the audience tools to use at the very beginning of the event. It could be a framework for how to think about the event and every activity in between. It could be physical tools that they will employ throughout the event. And once you do, make sure your audience knows how to use those tools. Test them. Give them small, but easy case studies and questions. Make it easy. Don’t put them on the spot. And by completing that test, that satisfaction and joy will help motivate them to use it more later. As Sanderson’s first law of magic goes, “your ability to solve problems with magic in a satisfying way is directly proportional to how well the reader understands said magic.” More on my thoughts on Sanderson’s laws here.
  4. Plots — Like any good story, the narrative is governed by plots. The plot must thicken and build towards a climax. And it must be resolved by the end of the event. Leave little in the main plot to chance, but leave room for each guest to discover something extraordinary. Maintaining a minor amount of stress and uncertainty, while sharing examples and reminders of being open-minded to new experiences, goes a long way. Only after stepping outside one’s comfort zone can one grow.
  5. Always use the audience’s time in a way that does not feel wasted — Inspired by one of the greatest writers of all time, Kurt Vonnegut. I forget which lecture he did that I learned this from. But it’s always been a governing theme for what I do.
  6. End on an ending where the reader can imagine no other — No loose ends. Everything that is teased (whether the audience realizes it or not) needs to be resolved by the end. This might be a semi-controversial opinion among storytellers and creative professionals. But I’m biased. I like my stories to end with a bowtie.

In closing

As you might imagine, much of this is still incomplete. And I hope to share more as I continue down this path of exploration and discovery.

Photo by Artem Sapegin 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.

v27.0

The Earth has once again gone through another orbit around the only star within four light years from us.

In the past version of David, I’ve published many blogposts. Yet one of the most continual topics that owns real estate in my mind is the idea of the 99 unsolicited, but more importantly, non-googleable (figuratively speaking) pieces of advice. I’ve already published two blogposts on the respective topics of entrepreneurship and VC. And am now compiling more and an additional set of life hacks. I imagine, at some point, I will for other areas of my life I want to spend mind space on. Asking questions. Hosting interviews. Events. LP stuff. Just to name a few.

In other words, I am on a constant search for tactical pieces of insight in the corners of both the internet and safely kept (often unwittingly) in the grey matter in 7.8 billion locations. Or simpler, I want to know what others know.

I was listening to a podcast featuring James Clear earlier this year. And in it, he said something I completely agree with. “Almost every idea you have is downstream from what you consume. When you choose who you follow on Twitter, you’re choosing your future thoughts.”

In an age that offers us a wealth of information and a million topics, posts, comments, videos, and algorithms that will distract us, it becomes ever more prescient to be a great curator. It doesn’t even have to be for others. At the very minimum, for yourself.

The amount of time I’ve scrolled through metaphoric cat videos on YouTube is appalling. And I realize that whenever I do, I face a dry spell of ideas. Luckily only briefly.

As of now, the world’s top social media platforms’ algorithms work against us. It surfaces us content we are likely to enjoy. Content that is high likely to reinforce our confirmation bias, as well as availability bias of the world. And the biggest problem with that is we are fed cousins of the same information rather than new, and possibly dissenting information that would challenge our beliefs. After all, these apps’ goal is to keep us on the platform. Not to close the app and do something meaningful with our lives. I’m excited for the day we get to build our own algorithms for consumption. But for now, it has to be more manual.

James Clear also goes on to say in the same interview when Tim Ferriss asked how he chooses which books to read. “First thing is you got to be willing to quit books fast. If you have baggage around finishing books, then you’re just going to be stuck and you won’t move on quickly enough.”

I’m guilty of the counterfactual. I’ve long prided myself on seeing things through. In fact, I still do. But at least on the consumption part, I’m slowing down my rate of learning. This year, I’m going to start measuring the number of books, articles, and podcasts I fail to complete, as well as the number of long form content media (i.e. books, movies, articles, podcasts, etc.) that have inspired an idea or an output. The goal is to optimize for learning and insight rather than completion.

Since this is the first year I’m measuring it, I won’t be able to measure the delta. But I’ll leave this encased in amber for David v29.0 and future iterations.

Doing things that are unteachable

My sixth grade teacher once told me, “David, you should be proud [she] copied you. That means you have something worth copying.”

I, like many others, spent the first 22 years of my life copying and learning from someone else’s or multiple people’s playbook. And often still do. The four years after I worked on being different. From the words of someone I look up to, “Be interesting and interested.” Where I put more effort into being interesting — doing interesting things, having interesting perspectives, asking interesting questions. I worked to create things worth copying. And when I started this blog, I followed that same ethos. I did and will continue to do my best to share my findings and takeaways. So that others won’t have to fall through the same potholes as I did.

At least, that was my belief until December 8th last year.

I hosted an event. An event I’ve never been more excited to host. An event where I was intentional about as many details as I could. And a byproduct of being in the flow state at least twice a week. While I’ll likely spend another blogpost taking a deeper dive on this topic, it occurred to me that events, just like any other medium of consumption — movies, books, podcasts, shows, and so on — should be stories. And every story has a beginning, a middle, and an end. But more importantly, every great story has:

  • An inciting incident — something that compels the protagonist to leave their current timeline to embark on something spectacular
  • A main plot (with sometimes multiple side plots)
  • Character development — the protagonist, as well as other characters, grow over the arc of the story
  • An ending where the reader (viewer or listener) can imagine no other (tipping my hat to Robert McKee)
  • And to use the reader (et al’s) time in a way that is not wasted (tipping my hat to Kurt Vonnegut)

To my joy, it was as great if not greater than expected. The feedback was phenomenal. In my excitement and post-event high, I shared with many friends, colleagues, and family about how I thought about the event.

And to my dismay, while most were happy for me, a friend told me:

“You’re built different. I could never do what you do.”

In subsequent days, two other friends told me the same.

And it reminded me of something John Fiorentino once said. “The things that are going to be valuable are the things you can’t teach or copy.” While I was initially dismissive of this corollary, I now realize there might be some truth to it.

So, how does that change the stories I’ll share here or anywhere? In the past few years, every time I do something new, there ‘s usually a voice in the back of my head that asks me, “How would you catalog this adventure on your blog? What would be the title of the blogpost? What kind of title works best for SEO?”

Going forward, I’m going to ask that voice to hush. Not to say I won’t share my learnings, but I’ll preface now that my future writings may not be written for search engine optimization. It’ll be raw. And from title to body, a truer expression of what I want to share.

So where do I go from here?

I’ve hedged to be fair my entire professional career. I’ve done tons, which on paper, seems like a lot, but I’ve never fully spent time immersing myself in only one thing. And nothing but one thing. I’m context switching all the time, which probably means I live 20-30% less of a day than a focused person.

So I’m going to have to take more risks. ‘Cause I’m starting to believe that in order to do something that cannot be copied, I’m gonna need to focus more.

Photo by Mike Lewis HeadSmart Media 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.