Silicon Valley Etiquette

Timeless rules for a new generation.

One blessing that was bestowed to me was growing up next to the farmlands around Krome avenue. It was in this upbringing (and multiple social failures in tech) that taught me that the mannerisms of the American South and the Bay Area are quite similar. They share similar values; work hard, give back, and treat others well. Throughout the years enduring from the antebellum, and although maybe not as well practiced- the Bay Area has its own set of professional and personal customs that should be abided by as much as Savannah’s.

But Silicon Valley diverges from other power centers in fascinating ways.

In New York, the social ladder is refreshingly direct and title-based. You're either a Managing Director at Goldman Sachs or you're not. You either live on the Upper East Side or you don't. You are either somebody, or you are not.

The hierarchy is explicit and measurable. Where your status is mostly based on institutional affiliation and financial assets. When two finance people meet at a party, they can assess each other's relative standing within about thirty seconds of conversation.

Silicon Valley operates on a completely different social architecture that would mystify a Wall Street banker. Traditional markers of status can actually work against you. Showing up to a startup event in a bespoke suit signals that you don't understand the culture. (Exception: All-In Podcast meetup) Name-dropping your Harvard MBA might get you politely excluded from an interesting technical conversation. The person in jeans and a hoodie might be worth nine figures, while the person in the expensive blazer might be a mid-level product manager at a struggling enterprise software company.

When talking to new grads, usually they struggle to know what is appropriate and what isn’t. However, I don’t see much people discussing why etiquette matters so much in the Valley and Valley adjacent centers. Your social position is determined by a complex matrix of factors and none of these are immediately visible, which means everyone here has to develop sophisticated social intelligence to navigate the hierarchy. (Unless you are a rationalist.)

I'm writing this because I have given this talk to many a young entrepreneur, and I am noticing a pattern of naïveté that I used to have when I started my career. Dropped balls, faux pas- you know the like.

So I figure it was time for a another guide. What often happens is that when I want to introduce someone to someone else, or they ask for an introduction. The intro gets made, and the relationship on my part gets burned. I then usually have to explain the very information you are about to read.

Done right, any backwater mud-man like myself can find themselves at home at any dinner or inbox so you chose. …And what is rather interesting is that the same set of manners has leaked over into most major financial hubs. Now many Californian’s who gone east are starting to enforce their social customs wherever they go.

This post will be split into four parts:

(If you don’t care for the usual Angelo sociology stuff, you can skip right to 2.)

1. Origins of Silicon Valley Manners

2. How to conduct an introduction

3. How to send a cold email

4. Conclusion: Do What You’re Going to Say

But first, we must understand why the Valley behaves the way it does…

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Origins of Silicon Valley Manners

One must look to Sunnyvale as well as Haight-Ashbury to see where Silicon Valley’s social structure comes from. It’s a peculiar storm of multiple parts owing to the regions unique importance in WW2, the counter-culture movement, and California’s penchant for gold rushes… well, er, Silicon.

In the 50s and 60s traditional computer companies like Hewlett-Packard and defense contractors like Lockheed’s Sunnyvale and Fairchild were the primary employers in the Bay Area. These companies brought a command and control professional culture where your word was your bond because someone's missile guidance system depended on it. (…and clearances are based on reference checks.) When a Lockheed engineer vouched for someone's security clearance, they were putting their professional honor on the line. For civilian companies, employees in California were able to move freely because the state didn’t have non-competes. (Unlike New Jersey, home of Bell Labs) planting the seed of the positive sum sharing of information.

The University of California system then created an environment where Berkeley University (and Stanford) contributed to the second part, knowledge workers. Academic culture operates on citation networks and peer review, but it also functions through long-term relationships between professors, students, and industry contacts. Professors introduce promising students to industry figures, who later become new industry figures. This started the cycle of continually focusing on new and interesting talent and ideas.

Then along that thread a free radical, or radicals, also made their contribution to the local culture. The counterculture movement of the 1960s. These were hippies and lefties who explicitly rejected corporate hierarchies and status symbols. (A practice that still can be found in some now recessed hacker anarchist circles.)

These opposing forces created an unusual equilibrium: egalitarian ideals that flattened traditional hierarchies, combined with engineering precision that demanded accountability for recommendations. The result was a culture that rejected traditional status markers while maintaining standards for credibility.

Enter the Don

The Bay Area engineering culture started to form into it’s own unique business culture with the advent of it’s own financial instrument, venture capital.

Risk capital was nothing new— hell, Mark Twain invested in a experimental typewriter and lost a significant sum of money.

However, Don Valentine at Sequoia Capital, catalyzed this dynamic into something entirely new. Valentine and his contemporaries weren't traditional bankers evaluating collateral and balance sheets. Fun fact: Don Valentine hated lawyers and MBAs.

His insight was that his judgement was betting on people and their potential to build massive companies from nothing was a better funding mechanism than

Unlike the dentist who watched Shark Tank and thinks he can run your business better than you, sophisticated VCs understood their role was calling the direction of the future and network access. This created a high-trust environment where relationships could develop over longer time horizons without constant transactional validation.

Valentine was revolutionary because he formalized the reputation economy that had been emerging organically. When Don wrote you a check, he was lending you his professional credibility to the founders. (In his case, his experience at Fairchild.) This model spread throughout the Valley, creating an ecosystem where your ability to attract quality investors became a proxy for your own quality as an entrepreneur.

Consider Y Combinator, which operates like a debutante ball for startups. Demo Day isn't fundamentally different from a cotillion: young people getting formally introduced to society. You can think of Paul Graham and Jessica Livingston as social sponsors, using their reputational capital to introduce promising entrepreneurs to the broader Silicon Valley establishment. (The companies in YC, more often than not, aren’t great businesses when they debut.)

Take these ingredients with the great regional climate and you get geographic density, compressing these dynamics into a concentrated social ecosystem.

When everyone lives within thirty miles and attends the same dinner parties, reputation travels at cocktail party speed. Unlike other environments… even today… this reputation economy welcomes newcomers in ways that traditional hierarchies cannot. Unlike inherited social standing or accumulated wealth, reputation can be built relatively quickly through demonstrated competence and network building.

The insight here is that anyone can play the game, if you discover the rules. However, to maintain it’s high trust system of vouching, this is why it developed mechanisms for evaluating and transferring it.

This necessity gave birth to the elaborate social habits that govern Silicon Valley today—because when reputation is your primary currency, you need sophisticated ways to prevent counterfeiting. (…and if you note, Theranos didn’t raise from traditionally sophisticated VCs)

Now, let’s talk about the main currency of the valley. Introductions.

How to Conduct an Introduction

Let me tell you about a particular kind of social interaction that reveals something important about how trust operates in Silicon Valley.

You can watch this unfold anytime someone asks for an introduction to an important person. What looks like elaborate politeness is actually a sophisticated mechanism for managing reputational risk in an economy where reputation is the primary currency.

Here's how it works.

Let’s say you knew Jake Cooper, founder of Railway. Your other friend Sarah, would like an introduction to Jake. Your immediate instinct might be to fire off an email connecting them—after all, you know both people, they're both smart, what could go wrong?

Everything.

Let’s think about it from your perspective.

When you introduce two people, you're essentially co-signing on both parties character and professional judgment. If Sarah turns out to be unprepared, or worse, if she misrepresents her intentions to get the meeting, that reflects on your ability to assess people. If Jake has a terrible experience, he remembers that you were the one who vouched for Sarah's worthiness of his time.

Now think about it from Jake’s perspective. He gets dozens of introduction requests weekly, and his time is genuinely scarce. (Try being a CEO one day.) When someone he respects sends him an introduction, he's not just agreeing to a meeting—he's trusting their judgment about whether this conversation will be valuable. If the introducer has repeatedly sent him high-quality connections, Jake will continue taking those introductions seriously. If not, future requests get ignored.

And from Sarah's perspective? She's asking you to spend some of your social capital to get her access to someone she couldn't reach on her own. If she wastes that opportunity or behaves inappropriately, she's not just burning her relationship with Jake—she's damaging your willingness to help her in the future.

This is why the double opt-in process evolved. Instead of immediately connecting Sarah and Jake, you first reach out to Sarah: "I'd be happy to make that introduction. Before I do, can you send me a brief paragraph explaining what you're hoping to discuss with Jake? I want to make sure this will be valuable for both of you."

What you're really doing here is conducting due diligence. If Sarah can't clearly articulate her objectives or sounds unprepared, you can course-correct before anyone's time gets wasted.

Meanwhile, you're reaching out to Jake separately: "Hi Jake, I have a founder in my network building something interesting in the enterprise software space. She's looking for strategic advice on how to approach large enterprise customers. Would you be open to a brief conversation? Happy to send over her background if you're interested."

Notice what you're doing here. You're giving Jake enough context to understand the value proposition while preserving his ability to decline gracefully. You're also managing the power dynamic—Jake can say no without creating social awkwardness, and Sarah doesn't feel like she's being evaluated by the ultimate recipient of her request.

Once both parties express interest, the introduction email follows a specific format. Here's one in the style that I sent recently: (That I asked ChatGPT to jumble up the email, forgive the AIisms)

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Subject: Jessica <> David: Supply Chain Tech Opp.

Hello hello!

Jessica, meet David

David is building the next generation of supply chain infrastructure and has been quietly assembling what might be the most impressive logistics team I've seen. Day 1 he's been focused on solving real problems for enterprise customers while building sustainable unit economics. He's constantly traveling between customer sites, so I hope you can connect during his next SF trip.

David, meet Jessica

Jessica is a Partner at [redacted] who has led investments in three of the most successful B2B infrastructure companies of the past decade. When she's not in back-to-back board meetings, she hosts thoughtful gatherings that bring together the best operators in enterprise software. A former operator herself... Ask her about the early days of cloud infrastructure and what those scaling lessons look like.

David's ask is around advice for his Series A positioning, particularly how to frame his expansion strategy to institutional investors. I think Jessica's perspective on market timing would be invaluable.

Hope you both find time to connect!

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Note the structure… I'm providing context for why these two people should know each other, establishing their credibility through specific accomplishments, and giving them conversation starters that go beyond just business. The tone is casual but notice how I still include their relevant professional background and the specific reason for the connection. It is then expected that the parties BCC the person who introduced the person who that they don’t get any further emails.

The most common mistake people make is giving someone the cold shoulder— after connecting people, I get dead-air, please, please, please reply.

The second most common mistake is when people play super-connector without thinking through what specific value the connection might create. Each introduction should create mutual benefit for both parties, not just expand your network for the sake of expansion.

The double opt-in process ensures nobody feels ambushed by an unwanted conversation while demonstrating that the introducer understands the value of everyone's time. When executed correctly, you do your part in maintaining the high-trust equilibrium that makes Silicon Valley's reputation economy possible.

But what happens if you don’t know anyone? We’ll consider that thought experiment in the next section.

How to Send a Cold Email

Imagine you need advice from someone you've never met—let's say a rising associate at Kleiner Perkins. You have no mutual connections, no warm introduction pathway, and no obvious reason why this person should spend fifteen minutes of their day talking to you. Your only option is a cold email, which puts you in the peculiar position of trying to demonstrate competence in an intentionally opaque social hierarchy.

This creates what you might call the cold email paradox.

The people most worth talking to are precisely the people who receive the most requests for their time, which means your email is competing against dozens of others in their inbox. (…and AI slop.)

Consider what this looks like from the recipient's perspective.

I am not important by any stretch of the imagination but when I look at my inbox I think. “Does this person understand my actual areas of expertise?” “Have they done enough homework to make this conversation worthwhile?” “Are they offering something valuable, or just asking me to be their unpaid advisor?”

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The mechanics of getting this right start before you even write the email.

Your email address matters more than most people realize. When you email from metalpony.smith.092399@gmail.com, you're immediately signaling that you don't understand professional conventions.

The firstname.lastname@company.com format indicates that you've invested in basic business infrastructure and understand how serious people communicate. (Or at least have a normal firstname.lastname gmail!)

Your subject line functions like a headline for a news article: it needs to convey enough information for the recipient to understand what they're getting into without being clickbait-y. "Brief question about marketplace unit economics" works because it's specific and professional. "Quick chat" or "Exciting opportunity" sound like spam because, well, that's exactly what spam looks like.

The more specific the ask the better.

Lord knows how many times I wanted to ragequit my inbox when someone wanted to pick my brain.

Let’s assume you listened to a guest on a podcast and you found their email address. They were talking about the topic du-jour… AI.

Something that I would consider a worthy message would be:

“Your podcast comment about AI companies burning cash on GPU clusters while ignoring data quality hit home. We spent six weeks debugging our model only to discover our training data was garbage. I built something that solved this, saving money. Would you be willing to spend 15 minutes trying it out and giving me a quick yay/nay if it helps?”

You start with the context, what you have to offer, with a clear ask.

However, often times, in Silicon Valley: consider who you're actually talking to and what you're trying to accomplish.

The conventional wisdom says to reach out to the most senior person possible, but this often misses how the ecosystem actually functions. Sometimes the most valuable relationships develop with people earlier in their careers who have outsized influence relative to their formal titles.

I've built some of my most important professional relationships through seemingly unrelated cold messages that blossomed over years into meaningful collaborations. A junior investor who remembered an insightful question at a roundtable I asked eventually became senior and made crucial introductions. An engineer I helped with a technical question later founded a company and brought me in for some advisory shares. These relationships succeeded because they were genuine exchanges of value rather than transparent attempts to extract something from someone more senior. (And it’s fun to work with friends.)

The key insight is that successful cold emails operate on reciprocity before they ask for anything. Silicon Valley relationships are fundamentally about value exchange, so your outreach needs to offer something meaningful upfront. This might be an industry insight they haven't considered, an introduction to a potential customer for their portfolio companies, or proprietary research that's relevant to their work. Too much transaction and you’ll rub people the wrong way.

Your milage may vary, but a general rule I try to base my career on is trying to give more than I take.

What makes cold emailing in Silicon Valley different from other business cultures is that it's simultaneously more meritocratic and more unforgiving than traditional hierarchies. Anyone can send an email to anyone else, but the standards for demonstrating competence and understanding social protocols are remarkably high. (And only getting higher with inbox spam.) When you get it right, you can begin conversations that would be impossible in more formal business environments.

Do What You’re Going to Say

We’re already quite long here and there’s much more I could write about but I will leave it here.

Your professional network operates on principles similar to traditional honor culture: reputation is everything, social debts compound over time, and burning bridges in a small world has consequences that last for decades. (but most people are generally forgiving.) That, to me, epitomizes Silicon Valley culture.

You do this by continually closing loops and doing what you are going to say.

The most important lesson I learned, often the hard way, is that your word is your bond in this ecosystem. Early in my career, I made the mistake of overcommitting and underdelivering—promising introductions I couldn't make, agreeing to timelines I couldn't meet. Each small failure to follow through chipped away at my credibility, until default.

The beautiful thing about Silicon Valley's reputation economy is that it's genuinely accessible to anyone willing to understand its underlying mechanics. When you approach networking as relationship building rather than extraction, when you follow through on commitments, and when you respect the social capital that others invest in you, opportunities compound in ways that can surprise you.

Who knows, maybe you'll be the next Don.