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Destination Weddings

At this rate I might as well re-name this section, “content from LinkedIn.”

I’m sure many of you can relate to this. It’s inspired by the common things so many of us come across. Bachelor or bachelorette parties, baby showers, retirement parties, weddings, or any notable event that can crush your savings.

Am I the only one who thinks that some of these things have gotten out of hand?

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DM-ing is an Art, Not a Science

We live in a world where you can reach almost anybody, anytime. Most people have push notifications on, or at least get an email when they’re DMed. They might not reply…but trust me, they saw it.

That’s the game we’re all in: competing for attention in a world that’s loud as hell.

I’m a big believer in the butterfly effect. One DM can change everything. I once cold-DM’d a fintech exec, one month later we Zoom’d, he made an intro, and that intro led to our biggest sale yet. Another time, I DM’d one of the first investor’s in Carta. He invited me to breakfast and eventually intro’d me to one of our first angel investors.

So…I’m a DM specialist or at least a seasoned vet. For the past three years, I’ve spent every day firing off emails and DMs to investors, users, advisors, partners, and everyone in between. Many go nowhere. But at least most of them trigger a response.

Today I’m going to focus on angel investors & VC funds, but in the weeks to come I’ll cover the others.

Think Bigger (Or Don’t Bother)

First and foremost, most VCs and angels are hunting for their next billion-dollar payoff. If you’re telling people “yeah, I think we could sell this” or “we’ll grow this to $10M in revenue,” you’re not thinking big enough. Or at least, it probably doesn’t fit the model of raising capital.

VC math only works if they believe your thing can go really big. These days, if they don’t get in before a $25M valuation, the math doesn’t math to make a sizeable enough return for their LPs. They’re betting on 10 startups, hoping one is a grand slam.

So if you’re raising capital, you need to play in the billion-dollar sandbox. That doesn’t mean puffing your chest with fake numbers. It means knowing your unfair advantage, your secret sauce, and articulating why this could be the one.

Also—don’t raise a single dollar until you’ve read Venture Deals. (I’ve got notes in my Linktree if you want the main points.)

The Absurdity of Fundraising

Let me paint you a picture:

• One time, I pitched an angel for $15k at 7am, two hours into a 14-hour road trip. My girlfriend was in the passenger seat, our terrified cat was howling like it was the end of days, and I’m trying to sell a vision over spotty bluetooth. Spoiler: it didn’t work out.

• Another time, I hopped onto a Zoom with an angel group, 15 people, all cameras off. First words out of the moderators mouth? “Impress us.” Like it was Shark Tank but somehow worse.

• I once flew across the country, shook hands with an angel who said yes to a $25k check on the spot… and then waited eight months before actually wiring the money.

• I’ve had countless people say yes and never pull through. Countless people blow me off mid-meeting. Countless people say “stay in touch.”

• I’ve had someone accidentally email me saying they only met with me to get intel on another startup.

• I’ve had VCs demand I call them at 4pm on a Saturday… only for them to pick up from their boat with a garbage connection.

• And one of my favorites: an angel bragging about “writing $100k checks.” After a couple old fashioneds, he admitted he’d only made one investment in the past five years—for $5k.

This is the reality. Raising isn’t glamorous. It’s half rejection, half chaos, and the occasional “yes” that keeps you going.

My Outreach Playbook

Here’s how I’ve done it:

LinkedIn DMs: I avoid sales navigator at all times. Whether the motivation is sales oriented or raising capital, it’s all about relationships. People don’t like to be sold to, and that’s no way to kick off a relationship.

Cold emails: Short, punchy, and straight to the point. We all get spam, but VCs and angels get blasted more than anyone I know. Because everyone wants an investment, everyone wants their product sold to their portco’s, and everyone wants their access.

City blitzes – I’ll book a random trip to LA, BOS, NYC, SF, or Chicago and email every notable fund or angel I can find, asking to meet while I’m there.

The trick is always the same: dangle why someone should care about you, the problem you’re solving, and—most importantly—why now.

If you can’t answer why now, then no DM template in the world is going to save you.

Networking Build a Relationship

I really don’t like the term “networking.” It makes me think of sad corporate mixers with bad finger food, forced small talk, and everyone debating if that third drink is worth the headache.

But in startups, the world is way smaller than you’d expect—and I’ve seen too many people fumble at the one-yard line. Most folks play the short game: chase the sale, beg for intros, or grab whatever quick win they can.

The truth? The most effective way I’ve found to use your network is to forget about yourself for a second. Help other people with what they need—without asking for anything in return. It may not be instant, but it compounds. And in this game, compounding is everything.

Raising money is an endurance sport with no rulebook. You’ll get ghosted, lied to, strung along, and humbled. But if you’re relentless, sharp, think long term, and a little bit crazy, you’ll eventually find the ones who say yes.

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What’s Coming Next?

I’ll be diving into sales and the strategies we use to scale.

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