How I Got My Book on a Times Square Billboard

It was years in the making, and a lesson in why every "yes" counts.

On Monday afternoon, I walked into Times Square and stood in front of the iconic Nasdaq billboard.

It was a strange feeling, knowing what I knew: At exactly 4:25, my book cover would appear there.

So I waited. I paced. Then someone from Nasdaq came to greet me. Then a Nasdaq photographer arrived. And at 4:25, my book was there. We snapped photos.

Then I ran around high-fiving tourists until my moment in the spotlight was up. Watch below — it was hilarious.

Ever since, people have been asking me — how did you do that?

“So many of our authors try to do this without succeeding!” my PR team wrote me.

So, how’d I pull it off? Here’s my answer.

I operate on two guiding principles:1. Say yes as often as possible.

When I was in college, I was a snotty punk kid who often accused his once-favorite bands of “selling out.” That usually meant the band signed a big record deal and went on an awesome tour. In other words, they made money — or in my view, they abandoned the smallness that made them cool.

Then I fell in love with the work of writer Dave Eggers. A Harvard Crimson reporter accused him of selling out, and he responded with an epic rant that, when I read it in college, completely changed how I think. Here’s the part that slammed me in the face:

The thing is, I really like saying yes. I like new things, projects, plans, getting people together and doing something, trying something, even when it’s corny or stupid. I am not good at saying no. And I do not get along with people who say no. When you die, and it really could be this afternoon … you will not be happy about having said no. You will be kicking your ass about all the no’s you’ve said. No to that opportunity, or no to that trip to Nova Scotia or no to that night out, or no to that project or no to that person who wants to be naked with you but you worry about what your friends will say.No is for wimps. No is for pussies. No is to live small and embittered, cherishing the opportunities you missed because they might have sent the wrong message.

I read this and thought: He is right.

Then slowly, over time, I stopped judging others for saying yes, gave myself the freedom to do it too, and then started applying the philosophy of "yes" to almost everything else.

That set me up for the life I have now: I say yes to opportunities, to adventures, to meeting new people. I have built a very wide, almost absurdly random network of people. I do it because it makes me happy. But also, let’s be honest: It’s also helpful.

I like helping them, and they like helping me. Which brings me to...

2. Relationships are better than transactions.

Sometimes, when you ask for something, you will get it.

You might reach out to a stranger, asking them to look at a thing you made. Maybe this stranger will like it and support you. But the chances are low. Strangers have little incentive to look at your thing. Their time is better spent with those they’re invested in. And also, if you only contact your friends when you need something from them, they will start to become strangers to you.

But here’s the thing: When you say yes all the time, you start building more relationships. Those relationships add value to your life, even if you don’t have a favor to ask. The relationships will provide an exchange of ideas and experiences. And then, yes, when you need something, you have a better chance of getting help.

That’s why I will say yes to things, and then wait years before I ask anything in return.

You could call it a long game. That’s fair. But I like to think of it as building friendly momentum. Good things take time, and the greatest opportunities are years in the making.

Which brings us to Times Square.

Back in the early days of the pandemic, someone from Nasdaq asked for my help. They were putting together a virtual conference and hoped that I would develop a session for them.

This may sound cool, but do not forget: Back then, everyone was hosting these conferences. It was never clear how many people tune in, or whether it would be time well spent, and nobody paid anything. I was getting a lot of requests like this, and, with my two little kids stuck at home, I was stretched thin and struggling. Sometimes I’d do a virtual event and like 10 people would watch. I could never tell what was worth my time.

So, would I do this event for Nasdaq? I never hesitated: Of course I would.

Hopefully lots of people would show up, but I figured that’s really beside the point. I was just happy to say yes to Nasdaq. As I recall, the event was a lot of fun.

As a thank you, Nasdaq put my face up on their billboard:

How I Got My Book on a Times Square Billboard

That was awesome, but it also left me feeling a little empty. After all, those were the deep days of Covid. Nobody was in Times Square! And I had temporarily relocated to Colorado at the time, so I wasn’t even around to see it myself.

Still, this was a nice relationship. We stayed in touch. Lots of emails over the years. If this person asked me for something, I was always responsive. And in the meantime, I started writing a book. Roughly six months ago, as I began preparing my promotion, I dropped that Nasdaq contact a line to ask a favor:

Could they put my book cover up there?

It took a lot of follow-ups. As my PR team said, Nasdaq gets asked this all the time. But lucky for me: Years after I first said yes to them, they said yes to me. And I got the photo that everyone wants.

So, here’s the question for you now:

What are you doing today, and who are you connecting with today, that will lead to an amazing opportunity in many tomorrows? You may not know the answer — so just start saying yes.

"Don't Grow Bitter — Grow Better"

How I Got My Book on a Times Square Billboard

I had an incredible talk with the world-renowned brain coach Jim Kwik, who understands exactly how our brains adapt to change, and why it can be so difficult for us to find opportunities in hard times.

That quote I used above is his, and he's right: When things change, we can either grow bitter — or we can grow better. It's our choice.

On his podcast Kwik Brain, we discussed strategies that people can use to move forward and thrive. I've gotten a ton of great feedback on it. You can listen to it here.

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Cover credit: Nasdaq / Fabio García