Life is fleeting.

It’s been a while since I’ve sent you anything, and for good reason. I’ve drafted many emails, but none felt important enough to send—until today.

Coming into the New Year, I felt refreshed after 13 days off with minimal attention to my inbox. It was lovely: climbing, cleaning, walking, eating good food. I read Tress of the Emerald Sea and most of McConaughey’s Greenlights. I even watched Klaus three times—and could’ve watched it again.

Arriving at work (my second bedroom) on January 2 was exciting. I was ready to get back to it. I had a backlog of emails to catch up on.

One email, with a signed Insertion Order, was sent to me over the holidays and awaited my signature.

At 8:32 AM MST I sent it back signed, with this body:

CSIO attached.

Please send dates ASAP as these are renewals, we can activate fairly quick.

Bet,

Adam

I didn’t address the sender. I didn’t say Happy New Year. I didn’t even notice my spelling error on “best” until writing this email. I was rushing through my inbox catching up on all the things that came in over the break without much time to breathe.

At 8:52 AM, I received a vague email, followed by a call, informing me of the tragic death of William “Billy” DiMaio, 25, in the New Orleans attack on January 1. I realized I hadn’t even addressed him in my earlier email.

Billy took over ADOPTER Media’s business at Audacy after years of us evading them due to pricing and ad delivery we didn’t particularly like.

It was Jan 12, 2024, when I was first introduced to Billy—sort of. Actually, it was our intern who first interacted with Billy when he was CC’d on an email in November 2023 for a vetting request.

My first email I got from Billy:

Good Morning Adam and Happy Friday,

So great to meet you - I look forward to working across these accounts with the team!

Would love to get some time on the calendar for an opportunity to introduce myself and discuss where we can help with these brands. Please let us know of any dates/times that work for you!

Best,

Billy DiMaio

He was so green he didn’t even have a proper email signature at the time. Still, we got on a call. I likely gave him all the blunt reasons we didn’t buy from Audacy and expected him to give up.

To be honest, I thought Audacy was pawning off us to a new seller as a “training ground” of sorts.

For the next four months, several calls and many email volleys were sent my way in hopes of getting tests. We sent some vettings his way with rates they couldn’t meet until eventually we received an email titled: “Audacy x Adopter Media: Episodic Good News!”

That’s an email subject that got me excited and our business changed with them drastically.

Billy fought to get business for and from us. He never complained. He stood his ground. And when there was good business to be done, he came and he was ready.

I’m not going to pretend like I knew Billy well. But I knew him enough to know what I knew about him.

He was kind. Intentional. Thoughtful. Smart. Caring. Genuine. Athletic. Confident. Humble. Patient (you have to be to sell to me, I think).

I bugged him a lot about not getting to meet him in person and that it was going to happen soon. My next NYC trip or hopefully at Podcast Movement. Sadly, this is an opportunity I will miss.

I can’t believe he was only 25.

Reflecting on myself, I know I can be blunt, direct, and challenging for salespeople. I’ve been known to deliver harsh truths without much sugarcoating.

I’ve had two distinct moments on the same night at Podcast Movement in Denver quoted back to me. “__ Network is where good podcasts go to die” is one.

I can be quick with emails. Blunt. Non-negotiable. And positively frustrating at times.

I don’t sugarcoat or waste much time on deals. I’m very, “Here’s what I want and what I can pay for it.” I’m mostly a take-it-or-leave-it guy. But, I promise to be truthful with the results.

Yesterday, Ben Pratt of Blaze Media told me that in his 11+ years of ad sales business, I was the first buyer to come to him saying we can raise the rates on a show because it overperformed—I hope that’s not true in our industry broadly.

I treated Billy like I treated any other seller—he never backed down and instead stepped up. And we became good partners in time.

Perhaps it was his tough lacrosse background that gave him his sheer determination to prove his success. Whatever it was, he worked his ass off to earn our business and he did.

He earned my respect and admiration.

Thanks to Billy, Audacy became a regular topic at ADOPTER among Media Buyers. The campaigns he built and the relationships he fostered became pillars in many of our brand portfolios—I and my clients thank you.

Well done, Billy.

I do not want to use this tragedy to exasperate any unneeded lessons, but I do want to share what I have been wrapping my head around—for my own sake.

Life is fleeting. Memories are not.

We don’t know when or where our lives will end, only that they will. What matters is how we live and the impact we leave on others. I don’t regret my direct style with Billy—I believe he appreciated the honesty—but his loss reminds me to be mindful of how we interact with those around us. We can leave people standing tall or weighed down.

Billy always left me standing tall. Thank you, Billy.

Live as though you will be remembered. And live to be remembered well.

Billy DiMaio was a reader of The Roast—and someone I consider a friend and worthy of remembering. Rest in peace, Billy.

If you’d like to support the family of Billy, they have set up a GoFundMe here: https://www.gofundme.com/f/honoring-billy-dimaio-victim-of-new-orleans-terror-attack