This post is about the best lesson I learned this year. And to tell you it, I’ve got to tell you a story…

Today is Amazon Prime Day and Amazon Prime Day is made up. It’s not a thing - it doesn’t commemorate anything and neither 21 or 621 are even Prime numbers. I checked.

I have no idea how or why it started but here’s how I imagine that first meeting going:

Today’s post will help you raise money from non-VCs for your early stage startup. The current approach…

1. Spend 100 hours on a pitch deck

2. Send it to lots of people

3. Hope

On my first day at business school I tucked my polo shirt into khaki shorts.

I was 24 and had decided to leave a finance job in NYC to go to UNC Chapel Hill, and despite never having tucked a polo shirt into khaki shorts before, a few happy hours leading up to the first day made it crystal clear that that’s what people did here. Social proof is a hell of a drug. We’ll get back to that.

To be exceptional at anything, you need to benefit from asymmetric upside.

I find it helpful to put this in hourly terms. Your “average hour” needs to move you significantly closer to a goal than someone else’s average hour. If it doesn’t, you’ll just spend your life treading water alongside everyone else.

Your startup (and lots of other very important things in your life) will depend on moments. These moments seem, and often are, serendipitous. You get a job because you bump into someone at a wedding, you meet your spouse in line at Whole Foods, your startup gets funded because the kid of an investor you’re pitching loves your product.

These moments drive everything. Yet we leave them to chance.

My best friend growing up lived about 5 houses down from me. He moved there in 3rd grade, coming from a far away land called "Long Island" that to 3rd grade Brian sounded very exotic.

The first time I heard about The Da Vinci Code, a thriller written by Dan Brown and released in 2003, was from a kid in my dorm at Union College.

He was a strange kid. He spent most of his days watching CHiPs reruns in a bathrobe.

My college basketball coach was a real asshole.

Note: I learned after college he isn’t actually an asshole, we’re close now, but that’s not as strong of an intro.

My coach did two things college kids don’t care for all that much — he told us the truth and he held us accountable.

Why do you watch Schitt’s Creek?

Because it’s a good show? Sure — it’s funny. I’m 4 seasons in.

But it’s not a great show. I’d argue (successfully) that it’s not even the best show with the word Creek in the title.

Jerry Seinfeld used to hang pictures of the Hubble Telescope in the Seinfeld writers room.

Judd Apatow, interviewing Seinfeld for his book on comedians, Sick in the Head, asked why.

“That would calm me when I would start to think that what I was doing was important. You look at some pictures from the Hubble Telescope and you snap out of it.”

Want to own the shoes Michael Jordan wore in the 1988 dunk contest?

I sure do. And I can… sort of. Rally, a company that makes “the investments of the rich available to all,” lets you a buy “share” of expensive, rare things as if they were a stock. Things like 1968 Ferraris, one-of-a-kind Rolexes, and Birkin bags. If the value goes up, you, as the “investor,” make a profit.

I instinctively didn’t like Tony Robbins.

I had no reason to have an opinion on Tony Robbins, but I’d seen clips of him holding people in his massive hands with his massive jaw sticking out strolling barefoot across red hot coals and it all just seemed like a lot.

Quibi launched on April 6th and immediately signed up 1.7 million customers. The company is run by entertainment and tech royalty, and has raised $1.8 billion dollars.

Unfortunately, Quibi is already dead. They won’t be around in 18 months. Luckily, your startup can be.

I used to hate dancing at weddings.

I’m tall, goofy, and an awful dancer. Triple threat.

Growing up, I was unbeatable at H-O-R-S-E, the basketball game kids play when there’s just a few of them around and only one hoop on hand.

There are about 8k people on my newsletter list. That’s not a ton of people — your email list may have 5x that. But these are my people. I love them. It feels like I’ve scratched and clawed for each one, and I don’t want to lose any. Every unsubscribe feels like a dagger.

There are two types of people in this world, or at least in my New York City neighborhood: Those who get bagels from David’s, and those who get bagels from Bagel Boss.

I’m leaving Tacklebox to start a restaurant. It’s called “Baguette About It,” and I’m psyched.

Founders ask me this all the time, but it’s the wrong question. Whether an idea is “good”or not is impossible to answer. The right question is “do I have a chance to make this startup idea work?”