Ben Ehrlich is the founder and General Partner of First Momentum Capital, where he helps seed a new generation of venture capital firms. He is also the Director of Strategy at the Long Term Stock Exhange. Previously Ben worked across the venture ecosystem supporting companies in the Canadian Technology Accelerator, OutCast Communications and Cribspot (YC 15). In his free time Ben takes his Irish setter doodle hiking and enjoys watching the University of Michigan football team (mostly) win.
[00:00] Intro [03:43] The origins of the Out of the Crisis podcast [06:54] Ben’s advice for rookie podcasters [08:35] How did Ben first meet Eric Ries? [11:46] The play-by-play for Ben’s interview with LTSE [13:36] What do decisions and conversations look like at LTSE? [16:23] Building trust among team members [18:29] How does Ben build trust with GPs? [25:14] How did First Momentum Capital start? [30:42] What was the pitch to close First Momentum’s first fund? [33:54] How does Ben underwrite Fund I managers? [36:42] How does Ben measure a GP’s future deal flow (as opposed to today’s)? [45:40] What does a “No” from Ben look like? [57:50] Thoughts on fund governance [1:05:57] What is the role of serendipity in Ben’s life? [1:08:17] Commisso Bakery in Toronto [1:10:35] Thank you to Alchemist Accelerator for sponsoring! [1:11:35] If you enjoyed the episode, I’d appreciate it if you could share it with one friend!
“Make sure to pay the government, doctors, and podcast producers on time.” – Ben Ehrlich
“If you want to build trust with someone [on your team], if they screw up, you have to be okay with them screwing up because you put them in the situation.” – Ben Ehrlich
“We’re looking for concentrated, non-correlated bets.” – Ben Ehrlich
My friend invited me to a demo day earlier this week. Albeit, it was a bunch of summer interns presenting their project they’d been working on for the last two months. The few investors and I who sat on the judging panel were all admittedly quite surprised by the quality of pitches and products from students and hell, even within two months. In fact, these 10-11 interns have gotten much further in product development and customer discovery than most founders I’ve seen across the span of a year. Whether sampling bias or not, the latter is probably about 50%+ of what I see these days. And you’d think that AI would have sped up the product development cycle.
But I digress.
Simply put, I was impressed. So, in efforts to simulate actual pitches at demo days, I asked a team who had presented five features they’d been working on and gotten each to a working prototype. “If you had to kill three of the five features, which three would you kill?”
To which, the “CEO” replied: “To be honest, all five are quite important. But if we had to kill a feature, it’d be the AI chatbot, but the rest of the four go hand-in-hand.”
I pushed for a more discerning answer, but was met with a paraphrased version of the last answer. And of course, it left a little more to be desired. What I was looking for was something of more prescriptive specificity. For instance, “we’d focus on usage metrics, particularly with respect to retention cohorts and actions per session across all the features. And depending on what features seem to perform better than others, our plan is to focus 70% of engineering resources on the top feature, 20% on the second most popular feature, and 10% focused on either a permutation of the other three or spending time with our customers to see where they’re the most frustrated.” It may not need to be the “right” answer, but having a thought-out answer is helpful.
After all, the original question boils down to the fact that most founders fail from indigestion not from starvation. Charles Hudson wrote this great piece last month, aptly named “The Last $250K.” In short, one of the most common behavioral changes he’s observed is when founders are down to their last $250K. And, three things stand out in particular:
“The most important things to work on become incredibly clear.”
“The data needed to validate the company’s hypothesis becomes much clearer.”
“There are things that the company was doing that they stop doing because those things don’t really matter given the gravity of the situation.”
It’s a quick read. And I highly recommend it. Much of which I personally agree with. Not sure if that’s usually the $250K mark, but my personal sample size is far smaller than Charles’. Constraints are the breeding grounds of creativity.
What’s really interesting is that my first reaction to that blogpost was just like how the last 4-6 months of runway leads to deep focus, how do the last 4-6 months affect fund managers? And it’s not too far off.
Deployment speed slows. The simple reason is that they no longer feel the fire under their belly to deploy. Either because they’re close to their target portfolio size or they need to elongate the time horizon while they’re actively raising their next fund.
The quality bar for what gets funded goes up. Since your deal flow pipeline is likely not contracting, there’s a flight to quality. And quality more often than not, translates to traction, logos/brands, and founder’s prior experiences. While there are always outliers, I see many GPs take less risky bets that they would’ve otherwise.
GPs are actively planning for the next fund’s strategy. And actively synthesizing lessons learned. Or at least, with respect with how they pitch LPs. And if they’re an emerging manager, or a fund without clear wins in their last fund, the most important things also become painfully clear. They often focus on the 20% that drove 80% of fund returns.
GPs are spending a lot more time on portfolio support. Not only because graduation rates become a lot more important (for fund returns and narratives for prospective LPs), but also because references matter in diligence. And well, if you’re fundraising for your next fund, you can be damn well sure that a sophisticated LP is going to do anywhere between 10-50 reference checks. On-list and off-list. 20-30% of which with your portfolio companies.
Thematically, focus. While there are other constraints that help improve a founder or a fund manager’s level of focus, limited runway (or capital to deploy) is a natural forcing function. The best ones I’ve seen often impose artificial constraints early on, before things get rough. Rules and codes of conduct. Things they promise themselves and the team never do. Aligning compensation behind performance. In other words, operational discipline.
Naturally, it should be to no surprise that investors of any kind spend a lot of time on organizational discipline before they choose to invest.
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.
Susan Kimberlin builds and invests in things that are Good & Useful. She is an angel investor, limited partner and product leader with a career that is equal parts building SaaS software products, and investing in companies, funds, teams, and projects that promote social equity with practical solutions for real-world problems. She is committed to bringing more diverse people into investing and the innovation economy. With a background in building search and natural language products for companies like PayPal and Salesforce, she leverages her experience to help her portfolio companies with product and fundraising strategies. Susan believes that bringing diverse perspectives to creative and practical challenges is the best way to create durable and impactful change.
In addition to her tech roles, Susan co-owns and manages Tammberlin Vineyards, growing Rhône wine varietals in Bennett Valley, Sonoma County. She works on documentary and narrative film projects as an executive producer, supporting creative projects that raise awareness, start conversations, and bring joy. She is a lifelong singer, and has been singing with pop a cappella group The Loose Interpretations for nearly 20 years.
[00:00] Intro [02:51] What are madrigals? [10:10] How to balance high expectations for your team and the trust that they will get there [14:53] How does Susan recognize drive and excellence in others? [21:49] What made Susan’s founding LP check in Backstage Capital so unique? [26:01] Difference between LP stakes and GP stakes [38:51] The smokes and mirrors behind the first pitch [43:54] Susan’s investment strategy as an individual LP? [50:21] What topic would Susan give a TED talk in that’s not startups or venture? [59:24] Thank you to Alchemist Accelerator for sponsoring! [1:00:25] If you enjoyed this episode, could you share this with one other friend?
Raida Daouk started her career in banking before moving to the investment team of BY Venture Partner, a venture fund with offices in Beirut and Abu Dhabi. She quickly climbed the ranks within the company and ultimately became a Venture Partner.
Recognizing a void in the market for personalized venture consulting services, Raida established Amkan Advisory, a boutique consultancy firm specializing in assisting family offices and high-net-worth individuals in identifying venture funds that align with their specific strategies. Given that first-time fund managers often possess the most aligned incentives with their investors, she understood the significant value they bring to the venture capital landscape. However, Raida also understood the reluctance of family offices to commit capital to relatively unproven managers. By curating a portfolio of carefully selected funds, she aims to mitigate the perceived risk associated with investing in first-time managers while still accessing the high-growth potential of emerging ventures.
Amkan Ventures emerged to offer LPs access to emerging managers beyond their direct reach. Focusing on small Funds I and II led by ambitious managers with a conviction-driven approach, the firm prioritizes delivering returns and nurturing opportunities in the venture arena.
Amkan Ventures’ first close occurred in April 2024, with one investment already made in a $30M fund I out of NY and one more about to be announced.
Raida currently serves on the Selection Committees of RAISE Global and The Bridge Platform.
[00:00] Intro [02:45] The impact of biology on Raida’s career [06:24] If Raida were to teach a founder psychology course [08:42] Raida’s definition of “running through walls” [10:16] Similarities and differences between founders and fund managers [11:36] What does GP-thesis fit look like? [14:38] How Raida got to a yes on Nebular Ventures? [20:35] The personas of different kinds of references [26:05] The one question that Raida always asks during reference calls [28:31] Is there such a thing as too many references? [31:57] What if you don’t have a network of references as an LP? [35:26] How does one set up the venture arm of a family office? [40:28] What is the GCC? [43:58] The best way to build relationships in the GCC [47:54] The origin story of Amkan Ventures [52:19] How did Raida build a strong understanding of the foodtech space? [53:58] Where did Amkan’s name come from? [58:26] What fund is in Raida’s anti-portfolio? [1:00:30] What’s Raida’s take on solo GPs? [1:03:10] How does your mindset change as an LP if you had evergreen capital? [1:06:58] Thank you to Alchemist Accelerator for sponsoring! [1:07:59] If you enjoyed this episode, it would mean a lot if you could share this with one other friend!
“It’s always best to start the relationship when there is no ask.” – Raida Daouk
“The average length of a VC fund is double that of a typical American marriage. So VC splits – divorce – is much more likely than getting hit by a bus.” – Raida Daouk
“The more constraints you have, the more conviction you will have in each manager.” – Raida Daouk
These days I’ve been spending a lot of time thinking about succession and key person risks. Definitely influenced by a number of conversations I’ve had with a partnership I invested in who broke up and LPs who take the long-term perspective on investing in funds.
When I say long-term, I mean when those LPs invest in a firm, it’s not just a single check into one fund. They plan to budget out $XX million dollars over the next three funds or so. Or across 9-10 years primarily to invest in this fund manager. We’ve talked about how underwriting a solo GP is actually much easier than underwriting a partnership, at least on the key person risk side of things.
If a solo GP dies, they die, and the firm naturally cannot go on. And any capital reserved for them automatically goes towards net new investments. If a partnership loses a key partner, then it’s this awkward dance to figure out if the remaining partners are worth re-upping on. And a re-underwriting needs to occur.
Before I go any further, let me first define key person risk for the uninitiated. Key person risk is the risk created when a single person leaves or dies that creates meaningful knowledge, brand, or performance loss at the institution. Simply put, when shit hits the fan in a partnership, how volatile will the transition be?
As such, my recent conversations informs much of what I write below. For the purpose of this blogpost, I’ll focus on partnerships as opposed to solo GPs and founders.
All great relationships are battle tested. Battle-hardened. In fact, when I ask a set of co-founders how they resolve disagreements, and they say, they never disagree, I run in the opposite direction fast. So fast that I could be cast as Barry Allen. Maybe. If my acting were better. If two people never disagree, they’re either the same person (which is hard, ’cause even biological twins disagree) or they’ve never truly worked on something together that they would call their life’s purpose.
To me, the formula for battle-hardened relationships has two key variables.
Depth – High stakes
Breadth – Time for the stakes to manifest
High stakes
Even if artificially high stakes. Even if in the moment, all parties involved must truly believe that this is the be all, end all. That there is no Plan B. There’s no going back. That everyone has to see it through. In Hollywood, I believe it’s called the inciting incident. A clear market in time that after a set of events that there is no way one can go back to their old life. Whether it’s the state championships for a sport among high school students, or fighting for survival in the middle of nowhere. For artificially high stakes, one must distort the reality, so that at the minimum they must convince themselves of the gravity of the situation.
Why do high stakes matter? Because only then does one put their all into something. And when you truly care, you hold nothing back. High stakes reveals the character you are. If people can accept and embrace you at your worst, everything else is a cherry on top.
Time for the stakes to manifest
This varies for different people. Sometimes it takes time to care. Other times, it takes time to fully realize what’s at stake. And others still, may never get to that point of realization. For example, in a ball game with four quarters, sometimes it isn’t until the score is neck and neck in the fourth quarter do you give it your all.
In practice
So in practice, I love spending time with folks to talk about their past. Their origin story. And get into the weeds on key inflection points not only in their own lives, but also in the time they’ve gotten to know each other. When did they first work together? When did they realize they were more than just colleagues? At what point did they introduce their families to each other? What was the point of realization?
Most investors focus primarily on length of a relationship, which is definitely valuable information, but without depth, it’s easy to know someone for decades and care very little for their growth and success.
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.
Lisa Cawley is the Managing Director of Screendoor, a highly respected LP of GPs, investing in firm-builders by firm-builders, with a unique model for partnering with allocators to access the emerging manager ecosystem. She’s been covering venture capital for more than a dozen years, since 2010 at Ernst and Young, a private investment firm, and now to Screendoor.
Lisa is a proud graduate of Loyola University Maryland where she’s earned her MBA and MS in Finance, as well as her BBA in Accounting, with a double minor in Information Systems and Spanish. Lisa is a CFA Charterholder and holds a CPA from the State of Maryland. In addition, she’s also a member of Class 29 of the Kauffman Fellows.
[00:00] Intro [03:43] How swimming has influenced Lisa’s life to date [11:16] How does Lisa evaluate competitive spirit in others? [14:36] The importance of understanding LP side letter terms [21:33] Investing as a team AND individual sport [23:45] Screendoor as the LP of GPs [28:43] How does Screendoor align incentives with their GP advisors? [31:05] How do GP advisors get assigned to portfolio managers? [35:09] LP-GP fit [37:46] Generation 1 vs Generation 5 of a family office [43:19] How does firm-building differ from fund-building? [49:09] Reference checking a fund manager’s “unique” value-add [55:24] Which two life lessons would Lisa canonize in a time capsule? [57:36] What was in Lisa’s last OS update? [1:01:23] The different facets of education in Lisa’s life [1:09:09] Final words on being thoughtful as an LP [1:14:05] Post-credit scene [1:25:27] Thank you to Alchemist Accelerator for sponsoring! [1:26:29] If you enjoyed the episode, I’d great appreciate it if you shared it with 1 other person!
“[Swimming, like venture] is both a team and individual sport.” – Lisa Cawley
“If you are governing things from a point of a legal document, whatever that may be and having to refer to that in order to trigger a behavior, that often to me feels emblematic of a transaction, not a relationship.” – Lisa Cawley
“Performance is everybody’s right to continue to do their business in venture.” – Lisa Cawley
“You can be a critic while still helping somebody, and you can be a critic while still giving empathy and doing so with respect.” – Lisa Cawley
But I’m so glad I did. In it, Harry shared a question he likes asking “If we were hiring someone underneath me to support him, what skills would they have?” In many ways, it’s the same as another question Doug Leone shared on his podcast as well. What three adjectives would you use to describe your sibling?
It comes down to simple purpose of trying to ask about someone’s weakness without asking them “what’s your weakness?” Why does it matter? When you’re too forward with your question, say the weakness one, recipients always end up finding ways to explain their “weakness” as a byproduct of their strength, or not really sharing a true weakness. “I’m too honest.” “I work too hard.” And so on.
While the above set of questions may not work for everyone, and probably even less so now that Harry and Doug shared it in a public arena, I can’t help but appreciate the linguistic gymnastics to find the right combination of words that gets one the answer they want. Nevertheless, I’m sure there are many more on this planet who still have yet to be exposed to those questions.
Similarly, I find it to be a damn good question to ask when doing references on potential investments. The truth is every founder or GP one invests in will have weaknesses. And that’s okay. Everyone’s a human. But in reference calls, there are two hurdles that one most overcome in their diligence:
Getting the reference to share an honest assessment of the person they know. This is especially hard when these are on-list references. In other words, references that the person being diligenced is providing themselves. Naturally, this list is full of people who are almost guaranteed to say positive things about said individual. Besides, there is absolutely no incentive to badmouth another person. Neither do most people aim to do so.
How high on the priority list is this person’s weakness? Can I get conviction on this deal even if I were to accept this weakness? Does it matter as much in a Fund I? Fund II? Fund III? If they need to hire someone to fundraise for them, is that a question of ability or network? And how crucial is it not only to the firm’s survival, but also their outperformance? If they need to hire someone to manage their calendar, that may be lower on the priority list of risks for most LPs.
Nevertheless, I find Harry’s question a great one to ask former colleagues, occasionally portfolio or anti-portfolio founders.
The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
Evan currently serves as Head of Venture Capital Investments and Research for Integra Global Advisors, a multi-family office. Prior to Integra, Evan served as Senior Manager of Data Science for Anheuser-Busch InBev where he oversaw data science and strategy for the US marketing organization. Prior to Anheuser-Busch, Evan spent two years as a Management Consultant at Marketing Management Analytics and held a technical role at Amazon. Evan earned an MS in Computer Science with a concentration in machine learning from Georgia Tech and studied computational and applied mathematics at the City University of New York and finance and psychology at the University of Miami.
[00:00] Intro [03:27] What are the mechanics of a great cold email? [07:54] Evan’s background in sports marketing [10:54] The kinds of data to ignore as an LP [13:01] Portability and replicability of track record [19:57] How much thesis drift is too much? [22:37] What happens when a partner isn’t pulling their weight? [29:35] Why does Evan have two bachelor degrees? [34:38] Why study quantum mechanics in applied math? [38:25] Evan’s journey to Integra [45:21] Buy vs Build at a fund-of-funds [47:40] Questions to ask when choosing which vendor to work with [51:24] How Evan thinks about operational diligence [58:30] Setting up an information policy in your firm [1:01:39] Valuation policy at a hedge fund vs VC fund [1:11:12] Why doesn’t Integra have strict mandates for geographies to invest in? [1:21:20] The fallacy with LPs overweighing DPI in 2020-2021 [1:27:15] Evan’s greatest life lesson [1:28:14] Evan’s favorite kosher restaurants in NYC [1:32:07] “Post-credit scene” [1:34:24] Thank you to Alchemist Accelerator for sponsoring! [1:35:25] If you liked this episode, it would mean a lot if you left a like and shared this episode with one friend!
“It’s important to be data-informed, not data-driven.” – Evan Finkel
“Not only does [an investment] have to be the best in that geography, it actually has to be better than the incremental dollar we could put in any other geography.” – Evan Finkel
“The way we think about VC is both on an absolute and a relative basis. On an absolute basis, we have to be able to underwrite a manager to 3X net or better, or ideally 4X net or better. Because otherwise the lockup doesn’t make sense. It doesn’t make sense to lock up your money for 10, 12, or 15 years with pretty limited distributions. In order to be able to consider a VC fund for our portfolio, we have to be able to underwrite it to at least 3X, but ideally 4X or better.
“But then there’s also a relative component. We’re not looking for the best relative managers. Understanding whether this is a really good year or weak year… You might be the best manager of a given vintage, but in absolute terms, you actually might not be quite as impressive. […] It helps us contextualize the performance of a given manager.” – Evan Finkel
“DPI generated in a chaotic environment is sort of similar to TVPI generated in a chaotic environment. It’s great it happened, but let’s contextualize it properly and don’t overweight DPI when you’re evaluating managers.” – Evan Finkel
“In venture, we don’t look at IRR at all because manipulating IRR is far too easy with the timing of capital calls, credit lines, and various other levers that can be pulled by the GP.” – Evan Finkel
Ian Park is a Partner at Primer Sazze, a firm dedicated to investing in ambitious talent across East Asia and North America. Prior to Primer Sazze, he was a venture capital allocator at Korea Investment Corporation (KIC), one of the largest sovereign wealth institutions in the world, where he focused on investments into venture managers and founders. He’s also amassed a fervent following of AI, VC, and LP fans over the years through writing his newsletter and his YouTube channel. Prior to KIC, he’s built his investing repertoire at VMG Partners and Bertram Capital after leaving the world of consulting.
Ian studied mathematics and economics at University of Minnesota and earned his master’s degree in economics at Boston College. He’s also got his master’s in computer and information technology from University of Pennsylvania as well.
[00:00] Intro [02:26] From Boston to SF [10:58] How does Ian diligence a GP’s ability to source? [13:37] The three things Ian looks for in emerging managers [17:04] Best practices on sharing insights [26:37] A typical week at KIC and conversations with GPs [30:42] How to best approach co-investment opportunities as an LP [33:38] How does Ian get to conviction on a direct deal [39:19] What funds should you invest in if you prioritize co-investments? [43:23] What does Ian look for in a Fund II/III that’s not TVPI, DPI, or IRR? [47:26] Relationship management best practices with GPs [53:30] The good, bad, and ugly at a sovereign wealth fund [1:00:00] What is Ian investing in at Primer Sazze? [1:10:20] What has Ian learned over the years as a content creator? [1:16:57] Thank you to Alchemist Accelerator for sponsoring! [1:17:57] If you liked the episode, would greatly appreciate a like and a share!
“Regression is trying to figure out why this happened, and machine learning is more about what’s going to happen.” – Ian Park
“The three things I’m looking for in emerging managers are first, information; second, network; third, it’s more about co-investments.” – Ian Park
“VCs should publish their thoughts as soon as possible – be it on YouTube or be it on a blog. You have to tell people what you think, and you have to claim that’s your idea too, so you can get some credit.” – Ian Park
“My rule of thumb is five years for 1X [DPI] for PE funds, and seven years for VC funds.” – Ian Park
Inspired by John Felix in our recent episode together, as LPs, we often get pitches where GPs claim they’re an N of 1. That they’re the only team in the venture world who has something. Usually it’s the fact that they have brand-name co-investors. Or they run a community. Or they have an operating background, like John says below. And it isn’t that unlike the world of founders pitching VCs.
The truth is most “unfair advantages” are more commonplace than one might think. Even after one hears 50 GP pitches, one can get a pretty good grasp of the overlap.
For the purpose of this blogpost, the goal is to help the emerging LP who has yet to get to 50-100 pitches. And for the GP who hasn’t seen that many other pitches to know what the rest of the market is like. Obviously, the world of venture shifts all the time. What’s unique today is commonplace tomorrow.
For the sake of this post, and to make sure I’m not using some words too liberally, let’s define a few terms I will use quite often in this blogpost:
Product: A fully differentiated edge that an emerging manager/firm has. In other words, a must-have, if the firm is to succeed.
Feature: A partially differentiated edge, if at all, an edge. In many cases, this may just be table stakes to be an emerging manager today. In other words, a nice-to-have or expected-to-have.
Networks
Product
Feature
Differentiated community (high/consistent frequency of engagement)
Alumni network (school or company)
Downstream investors that prioritize your signals
In-person events
Keeper test
Virtual events
Co-investors
Networks, in many ways, are synonymous with your ability to source. It’s the difference in a lot of ways from co-investing versus investing before anyone else (versus investing after everyone else). The latter of which is least desirable for an LP looking for pure-play venture and risk capital.
The quickest check is simply an examination of numbers. LinkedIn or Twitter followers. Newsletter subscribers. Podcast subscribers. Community members. While it’s helpful context, it’s also simply not enough.
Here’s a simple case study. Someone who has 5,000 followers on LinkedIn with hundreds of people engaging with their content in a meaningful way is usually more interesting than beat someone who has 20,000 followers on LinkedIn, who only has 10s of engagements. Even better if one generates a substantial amount of deal flow with their content alone.
One thing that is hard to evaluate without doing an incredible amount of diligence is your founder network referring other founders to you. From one angle, it’s table stakes. From another, true referral flywheels are powerful. In the former, purely having it on your pitch deck without additional depth makes that section of the deck easily skippable.
One of my favorite culture tests is Netflix’s Keeper test. That if a team member were to get laid off or fired, would you fight to keep them or be relieved? The best folks, you would fight to keep. And as such, one of my favorite questions during diligence to ask the breakout / top founders in each GPs’ portfolios is: If, gun to head, you had to fire all your investors from your cap table and only keep three, which three would you keep and why?
Do note I differentiate breakout and top founders. They’re not mutually exclusive, but sometimes you can be brilliant and do everything right and things still might not work out. But smart people will keep at it and start a new company. And maybe it was a smaller exit the first time, but the second or third time, their business may really take off. Of course, sometimes I don’t have the same amount of time to diligence each GP as an LP with a team, so I generally ask the question: If all of your portfolio founders were to drop what they’re currently doing regardless of outcome, and start a new business, who are the top 2-3 people you would back again without hesitation?
At the end of the day, for networks, it’s all about attention. It’s not about who you know, but about how well you know them AND who you know that TRUSTS what you know. In an era, where there is more and more noise and information everywhere, a wealth of information leads to a poverty of attention. But if you have a strong foothold on founders’ and/or investors’ attention in one way or another, you have something special.
Experience/expertise
Product
Feature
Early hire at a unicorn company + Grew a key metric by many multiples
Hired top operators who’ve gone on to change the world
Experience at a larger firm where you didn’t lead rounds / fight for deals
Independent board member
Experience only matters here where there are clear differentiations that you’ve seen and can recognize excellence. In a broader sense, having an operating background is unfortunately table stakes. As John mentioned, any generalities are.
While strong experiences help you source, its main draw is that it impacts the way you pick and win deals. Only those who have experience recognizing excellence (working with or hiring) know the quality in which A-players operate. Others can only imagine what that may look like. That’s why if you’re going to brag that you’re a Xoogler (or insert any other alumni), LPs are going to care which vintage you were at Google. A 2003 Xoogler is more likely to have that discerning eye than a 2023 Xoogler. The same is true for schools. Being a college dropout from a Harvard and Stanford is different from dropping out of college at a two-year program. Not that there’s anything wrong with the latter, but you must find other ways to stand out if so.
Given a large pool of noise when it comes to titles, it’s for that reason I love questions like: “What did you do in your last role that no one else with that title has done?”
Additionally, when it comes to references, positive AND negative references are always better than neutral references. Even better is that you stay top of mind for your founders regularly. A loose proxy, while not perfect, is roughly 2-3 shoutouts per year in your founders’ monthly updates. It takes a willingness to be helpful and for the founders to recognize that you’ve been helpful.
Process
Product
Feature
Response time/speed
Some generic outline of an investment process
Evidence of a prepared mind
Doing diligence
Asking questions during diligence most others don’t know how to
Yes, response time (or speed in getting back to a founder, or anyone for that matter) is a superpower. It’s remarkably simple, but incredibly hard to execute at scale. By the time, you get to hundreds of emails per week, near impossible, without a robust process. One of my favs to this day happens to be Blake Robbins’ email workflow who’s now at Benchmark.
Now I’m not saying one should rush into a deal, or skip diligence, but making sure people aren’t ghosted in the process matter immensely. As my buddy Ian Park puts it, it’s better for a founder or an LP to know that a GP is working on it than to not feel heard.
You’ve probably heard of the “prepared mind.” The idea that one proactively looks for solutions for a given problem as a function of their lived experiences, research, and analyses over the years.
Its origin probably goes as far back as Louis Pasteur, but I first heard it popularized in venture by the folks at Accel. Anyone can say they have a prepared mind. From an LP’s perspective, we can’t prove that you do or don’t have it outside of you just saying it in a pitch meeting. That’s why a trail of breadcrumbs matter so much. Most people describe it as a function of their track record or past operating experiences. Unfortunately, there may be a large attribution to hindsight bias or revisionist’s history. Being brutally honest with yourself of what was intentional and what was lucky or accidental is a level of intellectual honesty I’ve seen many LPs really appreciate. As an example, I’d really recommend you hearing what Martin Tobias has to say on that topic.
But the best way to illustrate a prepared mind is easier than one thinks. But it also requires starting today. Content. Yes, you can tweet and post on social media or podcast. But I’d probably rank long-form content at the top.
Public long-form writing (or production in general) is arduous. The first draft is rarely perfect. Usually far from it. With the attentive eye and the cautious mind, you go back to the draft again and again until it makes sense. Sometimes, you may even get third parties to comment and revise. Long-form is like beating and refining iron until it’s ready to be made into a blade. And once it’s out, it is encased in amber. A clear record of preparation.
In closing
Pat Grady had a great line on the Invest Like the Best podcast recently. “If your value prop is unique, you should be a price setter not a price taker, meaning your gross margins should be really good. A compelling value prop is a comment on high operating margins. You shouldn’t need to spend a lot on sales and marketing. So the metrics to highlight would be good new ARR/S&M, LTV:CAC ratios, payback periods, or percent of organic to paid growth.”
In a similar way, as a venture firm, if your value prop is truly unique, you’re a price setter. You can win greater ownership and set valuation/cap prices. If your value prop is compelling, the quality of your sourcing engine should be second to none, not just from being present online, but from the super-connectors in the industry, be it other investors, top-tier founders, or subject-matter experts.
Of course, all of the above examples are only ones that recently came to mind. The purpose of this blog is for creative construction and destruction. So if you have any other examples yourself, do let me know, and I can retroactively add to this post.
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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.
