VCs Beyond The Meme

The First Principles of Being Useful, Circling Back, and Backing Outliers

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The power of a meme is in its truthfulness. "There is a little bit of truth in every JK." In fact, memes are increasingly extending past truthfulness into economic power. One of the memes that hits closest to home in my own life is "let me know how I can be helpful."

Since I started writing, I find myself reflecting on the meme of VCs pretending to be helpful. I've started collecting what I've affectionately referred to as The “Let Me Know How I Can Be Helpful” Series:

• How can I be helpful vs. Is this helpful?

• The Tales of Usefulness Have Been Greatly Exaggerated

• Let Me Know How I Can Be Helpful

• You Don’t Want My Value Add

Most recently, I've found myself cringing at the meme because I've had several interactions over the last few weeks with people who are just getting started in their career as VCs. And, each time, I could feel myself summarizing a key aspect of the job as some synonymous phrase akin to "let people know how you can be helpful."

All of the pieces I've written on the topic before were more about prosecuting the sentiment of the meme. But the reality is that as much truth as there is behind the criticism that VCs stop at "how can I be helpful" without actually being helpful, there is also truth behind the first principles that VCs should approach things from the lens of being helpful.

Where Do I Start?

The conversations I had with people starting off on their VC journey revolved around a similar question: where do I start? So I thought about what I would do if I was getting started in venture.

Find Your "Why"

I've written before about the my introduction into the world of venture capital:

"I started my career as a founder building a creator marketplace long before I knew to call it that, or even to call it a startup. When justifying my work to my mother-in-law, I always called it a project. Partly because I didn't want to trigger her criticisms of my company not being "a job," and partly because I didn't know what else to call it.

I built Sandbox as a way to help videographers, photographers, and graphic designers get jobs. What I loved most about my work was the ability to support these passionate people, and be a resource to them in making their dreams a reality.

After I sold my company, I didn't know what to do next. I described my love of helping be this resource for passionate people to a friend of mine and he said, "Well, that's sort of what venture capitalists do." I didn't know what those words meant at the time, but that was the beginning of my journey into figuring out what I wanted, my "why."

Later, I had that idea embodied by a clip from The West Wing. You can watch it below, but here's the TLDR. The President's deputy chief of staff is frustrated because he's failed to accomplish something. The president says, "the difference between you and me is I want to be 'the guy.' You want to be the guy that 'the guy' counts on." That summed up my desire as a VC."

Since then, I've written about it over, and over, and over again. I keep coming back to this story because it is my guiding "why" of being a VC.

There are some people who want to be the smartest person in the room. There are some people who seek the thrill of the chase. There are some people who love to compete and win. There are some people who are obsessed with the discipline of capital allocation.

But for me, I just want to be "the guy that the guy (or girl) counts on." I have a servant mentality, not because I'm oh so very humble, but because I get more satisfaction out of breaking down walls for other people than I do out of breaking down walls for myself. I think that's probably why the "let me know how I can be helpful" meme is so irritating to me. Because I really do want to be helpful however I can be.

Now, that's not to say that being someone a founder can count on is the only reason to be a VC. Any of the above reasons can be fine (except maybe being the smartest person in the room; though thats one that a LOT of VCs gravitate towards despite it being almost never true). But whatever your why is, you need to have it. Because that what guides how you operate.

Relationship Business

Outside of my "why", you have to then confront the practical reality of the job. I started to reflect on the question of what some of the best investors have done to build their careers? Well, people say investing is, first and foremost, a relationship business. Like any good cliche, it strikes of as much truth as the best memes. My rough, shoot-from-the-hip framework was that investors typically take one of two (or both) approaches to building relationships: (1) deeply personal, or (2) deeply contributive.

For some investors, they focus on building friendships and those personal relationships trend towards opportunities to invest. Think about the number of investments that happen because people have worked together in the past, have kids in the same school, go to the same church, have the same hobbies, join the same poker match. Dozens of Midas List VCs have built their careers off of investing in the people they worked with at Google or PayPal or Palantir.

But the other approach is starting largely from scratch building relationships. The thing I love about venture is that just describing the process got me excited all over again about the potential behind this job. So I wanted to unpack the thinking that, previously, I've done through rambled ideas on a phone call. First, hopefully its helpful to other people who are starting to build out their relationships, and second, because I think going deeper into the thinking will help me better understand it.

So here's the thought process:

Building Nodes

If I was just getting started in venture, the first thing I would do is shore up any established connections I do have. From high school friends to college roommates to co-workers from my first job to people at my gym. Anyone I already know, the question I have to ask is whether that person will have any good connectivity to the broader tech / startup world.

I've always been a fan of the idea of having a personal CRM, but have never found anything that really does the job. Maybe there is some new AI context-rich personal CRM that I should check out, so feel free to send recommendations. But whatever the process or tool, the trick is not what you do to stay organized about the relationships you're building, but that you are actually building relationships.

From those initial conversations you identify the people who are much more plugged into other potentially entrepreneurial people. Within your foundational network you identify superconnector nodes that can lead you to other great people to meet.

Beyond your existing network you're also going and adding new sources for nodes. Pick a company that you think is interesting; they've built an interesting product, compete in a compelling space, or have produced some other great people you've met and respect.

By literally just going through Linkedin and looking at everyone's background, role, and (in particular) the slope of their career. How capable they seem of moving into new challenges and expanding the types of things they're capable of. You can also prioritize people who have been at their current company for ~3+ years. If people are going to start a company, they often wait until they hit their four year vest at their current company before leaving. Out of that exercise you'll identify a handful of new nodes to go investigate.

The Pitch

One thought is wondering why any of these people, especially from the new nodes who don't have any "first job" of "college"-type connections to me, be willing to talk with me in the first place?

If you're working at a venture firm already, there can be an honest pitch here.

"I'm looking to meet as many great people as I can, even if you're not looking to start a company. Across all the conversations I'm having, maybe there's new roles or new hires for your team or whatever else I can do that might be interesting to you."

If you're not working at a venture firm yet, but you're trying to build a deeper network you can frame it from whatever lens you're coming from that is a fit for them. Trying to learn more about the way they build things, the playbooks they've run, anything. And in return, hoping to share something useful with them.

Actual Listening

Whether its from your existing network, friends-of-friends through your "superconnectors", or new companies you explored, you're now starting to have dozens of conversations with interesting people. Here's where it gets tricky. The reason that "let me know how I can be helpful" is such a cringe meme is, at least in part, because (1) its transaction-adjacent; the VC clearly wants something from you in exchange for "being helpful", and (2) its shallow; they could know nothing about you and still say it.

Source: Twitter

You're not going into these conversations wondering "what am I going to get out of this?" You're trying to focus on what, if anything, can I do that would actually be helpful to this person. And for people who are just getting started, you might be thinking "what could I do that is useful to this person?" But you'd be surprised.

Any compounding engine starts by just getting going.

It reminds me of a stat I read about MrBeast. He, basically, published a YouTube video every 11 days for 10 years. Consistency and shots on goal are critical in building any engine.

So lets say you go have a dozen conversations out of these initial nodes you've identified. One person is an engineer at Databricks, one is a product manager at Retool, one is a researcher at OpenAI, and one is an engineering manager at Wiz. In each conversation, your number one job is asking questions and listening to the person talk about what is important to them.

• Engineer @ Databricks: Its his second job and he's really focused on progressing to manage people so he has experience running a team.

• PM @ Retool: She's thinking about leaving to join a startup as an early employee.

• Researcher @ OpenAI: He's just getting ready to leave and start a company and is looking to hire.

• EM @ Wiz: She's looking to hire more engineers on her team.

If you have enough conversations and you're a good listener and you do a good job of taking notes somehow to keep track of everyone, you'll automatically start to notice overlap.

What if I introduce the engineer at Databricks and the EM at Wiz? He's looking to manage people, which she does. And she's looking to hire engineers, which he is.

Could be a fit. But listening continues to be important because, what if the engineer at Databricks told you he hates getting recruited and doesn't want to leave anytime soon? Then setting him up to get approached for a job is bad.

What if I introduce the PM at Retool to the researcher at OpenAI? She wants to join a startup and he's starting a company and looking to hire.

Could be a fit. But maybe she said she's avoiding AI hype in picking the company she wants to join and he said he was only focused on engineers, not product hires right now.

If there is one cardinal sin that most VCs commit, its in being transactional and insincere. Listening is the antidote to insincerity. If you're really listening to someone, regardless of what they might do for you, it is much more likely that you can sincerely help them. Also notice that in almost none of the qualifying criteria for who to look for is "starting a company" on the immediate docket. By focusing, primarily, on people who look interesting, you distance yourself from the transaction, which enables you to be less transactional.

Compounding Engine

Existing networks, superconnectors, new nodes, referrals by those new nodes. If you push the limits of this motion you could very quickly find yourself having quite a lot of conversations. Lets say you're in SF and do these in person. Maybe 30 minutes per chat, 15 minutes of travel between. Maybe you meet folks from 9-5 each weekday. You could have ~50 meetings per week if its all you do.

After a month, you've had 200 conversations. And the real "rice-on-a-chessboard" compounder is if you ask each person who their sharpest friends are. Lets say you get ~2 referrals from each conversation on average. Pretty soon, you have an additional 400 names.

If you didn't think a personal CRM was necessary before, hopefully that helps you see how valuable it is when the numbers get crazy.

And one concern, if you're an investor, might be "listen, I need to be focused on finding people that are starting companies so I can consider investing." What if only 10% of the people you talk to are actually starting companies? Well first of all, in one month that would be 20 new companies to consider. Not bad. And second, you're not appreciating the value of the network you're building independent of "deal flow."

If you have a spreadsheet of 600 people you meet over the course of three months of crazy meeting schedules like this then you'll start to notice some things. A lot of them have similar backgrounds, some of them have unique specialties, some of them are interested in particular things.

When you meet someone as your 10th or 11th conversation, its just a matter of chance whether one of the first 10 people you met happen to have something that is valuable to the person you're on now. But by your 586th meeting, there are pretty high odds that someone in your pool of new friends might be interesting to the person you're talking to.

What's more, lets start to focus in on founders. Say your 601st meeting is with someone who is a senior software engineer at Glean. They've been there for 3 years and were at Figma for several years before that. They were referred to you by someone at Databricks; one of the smartest people you've met so far. They're starting to build a company you're excited about. And they have three asks:

• (1) I'm looking to hire engineers with a particular background

• (2) I'm looking to meet people who are engineering managers at large companies as potential customers of what I’m building

• (3) I'm looking for someone who could be a GTM advisor to spitball ideas with

Out of the 600 people you've met, 312 of them are engineers and 87 of them have backgrounds that might be interesting to this founder.

Out of the 600 people you've met, 45 of them are engineering managers, and 21 of them are at large companies.

Out of the 600 people you've met, 32 of them are GTM people, and 14 of them are senior enough to be considered an advisor.

This is where the magic happens. As you start to build a broader network of people you can be an enriching middleware layer that brings these people together. And the sheer scale is powerful. It reminds me of the quote by Ronnie Coleman:

“Everybody wants to be a bodybuilder, but nobody wants to lift no heavy-ass weights.”

Everybody wants to have some value-add, but nobody wants to have no 600 meetings.

Radical Prioritization

The immediate criticism I can feel rising from this exercise is a question of quantity over quality. 600 meetings in 3 months? How productive can that actually be. And I don't necessarily think you should have 30 minute meetings every 45 minutes for 5 days a week for 3 months. The point of the numbers exercise is to show that volume is important. You're developing pattern matching, you're expanding your network, and diversifying your "training data."

But over time, you run into Dunbar's number. You probably can't build meaningful relationships with 600 people. But as you meet people, you can find ways to reengage with certain people at certain times. Making introductions is powerful, even if you aren't becoming close friends. Finding ways to sincerely maintain your relationships, even if they're not close friendships, is huge.

Ultimately, however, you need to narrow down to the people you really want to build relationships with. Maybe thats one or two superconnectors that you really get along with. Maybe thats people who have said they want to be founders in the not-too-distant future and you think they're exceptional. So you prioritize those relationships over others to really get to know those people.

With those people, you can start to leverage the other playbook that many VCs use. Beyond just being contributive, you can make it personal. Spend time together as friends, introduce them to others, include them in Tennis matches, chess / poker clubs, dinners, etc. I think one of the mistakes I made over the course of my career was not becoming closer friends with the people I really liked.

Milk Before Meat

All of this is the simple version of something that is deeply complex and can be woven in a dozen different directions. You can deepen particular relationships in different ways. Building a bench of execs that you lean on, having a good motion for maintaining relationships with a lot of engineers through larger meetups, hackathons, or dinners, building in methods of helping your favorite would-be founders build in the early days.

There are dozens of ways that the best investors in the world have established to deepen their relationships and maintain their competitive ability to invest in the very best founders. For you, its first a function of establishing the foundation of a broad and deep network of relationships.

From there, you can identify the methods that are the best fit for your personality and style.

But across the board, the reason I'm thinking about this stuff is because the "let me know how I can be helpful" meme is a deep and rich pool of constructive criticism. Where is the sincerity? Where is the follow through? Why are VCs so criticized? Because the meme sheds light on a truth that most VCs are more interested in the potential of the investment than the potential of the person.

Venture has exploded as an asset class. It has become so big, so competitive, so meme-ey, so bubble brained, so consensus, so intellectually dishonest, so stupid. Its getting harder and harder to compete. But my belief is that, rather than having to amp up the transactional memeyness of venture, you can fight against the tide by just being a human being. Because, as depressing as it sounds, just being a genuine human being can be a competitive differentiator as a venture capitalist.

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