The Unspoken Rules of Business

The rules I wish someone had taught me at 22.

👋 Hi friends,

It’s been a few weeks since my last issue, as I’ve been traveling.

First, Lofoten, Norway, for fun, then Toronto, where we debuted The Shortlist with Boardy for Toronto Tech Week.

Norway was wonderful. We went to a beautiful, remote part of the country that felt like we were on another planet. And Toronto Tech Week was incredibly well done. Something that the tech community across North America should consider attending every year.

A great few weeks away from New York, but now we’re back for New York Tech Week. See our upcoming events below.

📅 Upcoming Events

• June 3 | 💻 The Non-Engineer’s AI Playbook, hosted by MuleRun (NYC) – Learn how to deploy AI as a work partner (I’ll be speaking!)

• June 4 | 🎉 Tech Extravaganza (NYC) – Our most exciting event of the year. We're taking over one of NYC's largest venues and transforming it into a massive multi-sensory playground.

• June 10 | 🍽️ Junto Founder Dinner (NYC) – Founders and CEOs only.

• June 17 | 🍽️ Junto Founder Dinner (NYC) – Founders and CEOs only.

• June 23 | 💼 The Shortlist: June Founder Showcase (NYC) – Meet the most exciting, fastest-growing startups in New York who are hiring.

• June 25 | 🚀 Founder Breakfast w/ Mark Pincus, Founder of Zynga (NYC) – I’m inviting two dozen founders to have breakfast and an intimate Q&A with Mark.

• June 30 | 🍽️ Extraordinary Founders Dinner (SF) – Hosted at one of the few Michelin-starred steakhouses in the country, known for Japanese A5 wagyu. EXTREMELY LIMITED SPOTS.

• September 18 | 🗽 The OOO Summit (NYC) – Our most important event of the year for entrepreneurs, builders & creators. Big announcement coming soon. Apply for early access.

• • •

A few years ago, I cold DM’d the CTO of Meta. He was a public figure whose work I had been following for years. To my surprise, he replied instantly and offered to meet with me for 15 minutes.

I was 25 at the time. And had barely interacted with executives at that level, let alone the chief exec at one of the largest public tech companies in the world.

I spent months preparing for those 15 minutes. And when the day came, I was insanely nervous. He was 4 minutes late to the call, so we only had 11 minutes. I had time for three questions, I thought to myself.

I panicked. I asked him three questions, which I now realize were unimaginative and boring. He answered in an equally unimaginative way, half-checked out and multitasking. I could tell I had ruined my opportunity to make a lasting impression. And I did. I emailed him again a year later. No response.

I go back to this example every time I think about the concept of “networking” or building relationships.

There are SO many unspoken norms and expectations around developing professional relationships and building social capital that are never taught in schools or in the workplace. In fact, most people I’ve met are oblivious to these rules. But once I learned them, they helped me succeed in both my corporate life and in entrepreneurship.

Today, I want to share those rules with you.

I learned most of these rules from spending time around busy execs, CEOs, and influential decision-makers. It comes from my uncanny habit of hyperanalyzing social dynamics (perhaps to a fault) over the last few years.

Building Your Network

• Build the well before you’re thirsty. This is first because it’s the most important one. Help people and provide value long before you ask for anything. Asking before you’ve given is the fastest way to deplete social capital and burn a bridge before you’ve even built it.

• There are only three ways to ‘network’. 1. Create something that gets people interested in you. 2. Be great at working the room. 3. Or give first, and generously. Better yet, do all three.

• Surround yourself with energy, not drain. Negative people are contagious, and the chronically unhappy are also unlucky. Choose your inner circle deliberately because the wrong people will pull you down. On the contrary, the right people will make you feel like you can run through walls.

• Identify relationships where lifetime value beats short-term gain. Sometimes this means taking a lower salary to work for someone exceptional. It might mean volunteering for a cause or even doing pro-bono work. Many such examples in tech.

• Create the room yourself instead of trying to get through the door. Host the dinner or throw the event. It’s often easier to be the host than to beg for an invite.

• Master the art of the ask. Be specific, be brief, and make it easy. Vague asks (” Can I pick your brain?”) get ignored. Specific asks (” Can I ask three questions about pricing strategy for my b2b app?”) get answered. And actually make the ask!

• Give more physical gifts. Give someone a gift when they refer you business, introduce you to a decision-maker, or do you a favor. Make it memorable enough that they never forget it.

• Treat junior people like senior people. The intern today is the founder in five years. The assistant is the gatekeeper. How you treat people who can’t do anything for you is the truest indicator of your character.

• Play long-term, positive-sum games. The best way to build social capital is to play long-term games with people who play them too. Short-term extraction will always lose.

Building Your Reputation

• Guard your reputation with your life. Robert Greene calls reputation “the cornerstone of power.” It precedes you into every room, every deal, every relationship. One unflattering story spreads faster than a hundred accomplishments. Protect it ferociously.

• Be a person of your word. The easiest way to build your reputation is to do what you say you’ll do. Ideally, do more than what’s expected. The worst thing you can be is someone who never keeps promises.

• Never burn bridges. I made this mistake many times. Even if you don’t like, respect, or admire someone, there’s no upside to burning the bridge. As the saying goes, “If I only worked with people I liked, I’d be broke.” You don’t have to be everyone’s friend.

• Bite your tongue. The hardest part about being in physical + digital proximity to people you dislike is learning to bite your tongue. Heated arguments and emotional emails have no upside beyond a brief moment of relief.

• Don’t double, triple, or quadruple message someone if they don’t respond. It reeks of desperation. Send once, follow up once, then move on.

• You can build genuine trust online. There’s more of a bond to “internet friends” than you might think. Build it by consistently sending emails, engaging on their posts, sharing their work, advocating for them, and adding value through thoughtful public debate.

• Use AI thoughtfully. AI has become a force multiplier that reveals who the most exceptional operators are, while exposing those who are lazy and tasteless. Don’t overslop your cold emails, important communications, or public writing.

• Always do double opt-in introductions. 99% of good introductions are double opt-in. Don’t fire off an introduction if you haven’t vetted both sides. The best introductions benefit both parties.

• Build your reputation around one memorable quality. Don’t try to be everything. Pick one trait and become known for it.

• Don’t be too eager. Like fundraising, like dating, like most things in life, you want to strike a balance. Things that seem abundant or too available feel lower value. This isn’t about playing games but about understanding your self-worth.

• Create public proof of your competency. Publish a blog with your writing or a portfolio of your work. Create proof of your skills that will serve as your public resume.

• Give first. Give generously, but not always altruistically. Time, energy, and resources without expecting an immediate return build a well of goodwill that lasts a lifetime.

Meeting Important and Influential People

• The easiest way to build a relationship with a busy person is to help them.

• As a young, early-career person, you have two advantages when it comes to meeting important people:

  • First, you have time. Most people think ‘help’ comes in the form of advice, connections, or capital, but you can literally help someone by contributing time and effort.

  • Second, everyone – no matter who you are – has insight into their specific corner of the world. Even if you’re a 19-year-old student, you can come to me and say: “Here’s what I’ve observed about my peers. I saw you write about X and Y, so I thought this might be useful to you.” That is value.

• The easiest way to get a public figure’s attention is to engage with their work online. Responding to social media and blog posts is a life hack. Even the most important people are accessible on a platform like Twitter.

• Play the internet lottery. Send out 10 cold messages or emails a week. Potential customers, partners, mentors. You only need a few to land.

Working With a Mentor

• Counterintuitive advice: recurring monthly mentor meetings often don’t work. You end up filling the time with arbitrary questions.

• Opt for a “board of directors” approach instead. Assemble a handful of people you can go to for specific situations, rather than forcing regular check-ins with one person. Different mentors for different problems.

• Don’t ask for broad, generic advice. “What should I do with my career?” is impossible to answer well. Most people don’t know your exact circumstances or what’s unique to you. Be specific.

• Don’t ask lazy questions. The most thoughtful way to engage a mentor is to think through the problem yourself, land on a few possible solutions, and present them to get their take.

• Put advice to work. Don’t be the person who constantly asks for advice without applying it. Apply it, then share the outcome. This is how you earn more of someone’s time.

• Consider sharing economics with great mentors. If you operate a business or P&L, give your best mentors referral fees or equity. It aligns incentives.

• You may eventually outgrow your mentors, or vice versa. That’s fine.

• • •

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

• Apocalypse No (The AI jobs narrative is BS) by Scott Galloway – Scott argues the AI job apocalypse is being massively overstated. Every generation thinks machines will wipe out work, but historically, technology creates new industries, new roles, and more productivity. The fear spreads because fear sells … and a lot of people benefit from making AI sound scarier than it is.

• If you can’t get a job today, it’s your fault by Auren Hoffman – Pedigree and school prestige no longer matters in the AI first world. Companies now care more about proof of work than credentials. The people standing out are the ones building things, learning in public, and showing initiative.

• The Six Megatrends That Define 2026 by Derek Thompson – Our increasingly anti-social culture, health miracle drugs, AI apocalypse, and geopolitics.

• Your Job Is Changing Faster Than You Think by Elena Verna – A lot of “good enough” knowledge work is about to disappear. AI won’t replace every role, but it will shrink teams and raise the bar for what makes someone valuable. What does ‘valuable’ mean exactly? Elena explains in this post.

• • •

💃 (Sponsored) The cheapest friendship therapy I've ever done

I built a tool that analyzed five years of texts between me and my best friend.

What it found about us surprised me…

He asked me 2x more questions than I asked him (I had no idea I was the worse friend).

73% of our conversations were started by me.

Our average message is 9.4 words. 1 in 3 contains a joke. Our most-talked-about topic is food.

I call it Perel. It analyzes your iMessages with a friend, partner, or family member and tells you what’s working and how to show up better. Built on the work of Esther Perel, one of the world’s most respected relationship therapists.

This is the kind of insight that takes years of introspection to get.

I built it in a day with Perplexity Computer.

Try it on your own iMessages – click here.

P.S. everything in the pictures is dummy data - but try it for yourself.

P.P.S it might work better with partner vs a friend ;)

• • •

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

• 🇺🇸 Looking for help with US immigration? Reply here – I’ll connect you with the attorneys and team I trust for visas, green cards, and all the corporate immigration matters.

• 🚀 Have a startup idea you’re considering building? Builders Between Ventures is a 3-week validation sprint with Forum Ventures’ AI Studio to pressure test your thinking, understand the market, and get clarity on whether it’s worth pursuing. And then pitch them for $250k! Apply here.

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• 👀 Profound just got a MAJOR upgrade with Profound Sheets. Profound Sheets lets you run hundreds of AI agents in parallel, saving you hours of time. Learn more here.

• 🧮 Need a CPA? I’ll introduce you to Alex, with whom I’ve been working for the past three years. He’s excellent and specializes in tax support for high-earning individuals and entrepreneurs. More info here.

• 🤝 Looking to hire fast? My friends at Morpheus Talent specialize in helping you find GTM business and engineering talent at startups. Learn more.

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• 🚴 Equinox – Reply here for a free trial and discounted membership.

• 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

• 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

• What other perks should I include? Let me know.

• • •

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• • •

🖼️ Behind the Scenes

Last week I was in Lofoten, Norway. I’ve never been anywhere like this before. It’s the most bizarre place I’ve ever been.

For one, during the summer, the sun does not set. 24 hours of daylight every day. The locals call it the Midnight Sun.

At 12:00 am, people are still hiking, kids were playing outside.

Five days of consistent daylight put me in an euphoric, trance-like dream state. Highly recommend experiencing this at least once in your life.