69 Day Giving Challenge – Day 2

Somehow I get the feeling there will be lot’s of “coffee” gifts.  So bear with me.

Yesterday I followed my normal routine of putting my oldest daughter Talia on the bus, and then heading to get my coffee before I start my drive into work.  I noticed something different about the morning, and I remembered why I loved doing the 64 day challenge so much. When you start your day looking for someone to give a gift to, your whole lense on the world changes.  You start to seek the good in the world. You see light and block out dark. It’s a profound shift that I missed since the last time I’d done something likes this.

Let me explain: as I pulled into Dunkin Donuts I looked across the street at the gas station. In the parking lot was a huge truck filling the tanks of the station. Just next to the truck stood a big burly truck driver, arms crossed, Chicago Cubs hat on looking utterly unimpressed with the world around him. I got out of my car thinking nothing of it when it dawned on me what my gift would be. I bought my normal large coffee, with milk, and I added a small coffee with milk and sugar. I mean, who doesn’t love a nice cup of coffee?  I walked out of the Dunkin Donuts, and I walked directly to the man. As I approached him it dawned on me that he may think I’m out of my mind, so I debated telling him why I was giving him a cup of coffee.

He looked up at me and I said.

Hey man, you look bored out of your f-ing mind, I thought you needed a cup of coffee

He looked at me, stunned. Blank look on his face. Heart beat… I broke the silence with

…seriously, here you go, and I handed it to him.

He smiled, looked down at the coffee and replied

thanks!

I quickly turned and began walking away.

It then dawned on me that he may throw out the coffee thinking I urinated in it or something (I don’t know why my brain works this way), but I saw that he had placed it on the bumper of his truck, and was opening it and taking a sip. He placed it back down.

WIN.

As I pulled out I looked over and gave him the peace sign.

Fun way to start the day!

To learn more about why I’m giving a gift every day for 69 days, please read this If you have any ideas where I can give, what I can give, or how I can go about giving please either email me at chrisdessi@silverbacksocial.com, comment  below or find me on Twitter @chrisdessi

Who’s the Coach?

I’m Chris Dessi.

Tech entrepreneur. Author. Talking head.
But before any of that—I’m a builder.

I’ve spent the last 20+ years helping companies grow:
From dot-com chaos to SaaS scale-ups to AI-powered everything.
I’ve sold software across continents. Closed $32M in deals using AI.
Built and exited businesses. Bombed a few too. All of it made me sharper.

Today, I run Torque AI, a marketing automation platform built for the 99%.
Small business owners. Solopreneurs. Operators with too much to do and not enough support.
We give them AI superpowers—without the hype, the jargon, or the BS.

I’m also the founder of AI Summit NYC, where real business owners come to learn how to actually use AI to drive revenue.

When I’m not building, I’m writing books, speaking on national TV, and coaching execs through reinvention—with a baseball bat in one hand and a meditation app in the other.

I believe reinvention is our greatest asset.
I believe AI isn’t the threat—it’s the test.
And I believe if you’re not adapting, you’re eroding.

Let’s build something that matters.

Get weekly insights

We know that life’s challenges are unique and complex for everyone. Coaching is here to help you find yourself and realize your full potential.