Revenue Diaries Entry 31

There’s nothing like today in Indianapolis. 

I was driving to pick up coffee this morning when I noticed dozens of bikers heading down our Cultural Trail. Six miles south lies an oval track that hosts the "Greatest Spectacle in Racing"—the largest single-day sporting event on the planet: the Indy 500.

Over 350,000 people. Completely sold out. 

Generations of families are doing what they’ve always done on the Sunday of Memorial Day weekend.

It’s easy to forget how special today is for Indianapolis. 

People ask where I’m from, and usually… blank stares. “Is that where the Colts are?” “How about ‘em Pacers?”

We’re still a sleepy but mighty Midwest city. But today is different. Today, the world knows where we are. 

The Indy 500 has been running since 1911.

It predates the NFL. It helped invent the rearview mirror.

And it takes place inside a venue so large, you could fit the Rose Bowl, Yankee Stadium, the Roman Colosseum, the White House, the Taj Mahal, the Statue of Liberty, and the Great Pyramid of Giza, inside the infield… with room to spare.

It’s where legends are made, and where Indy becomes the center of the sports universe, if only for a day.

And if you are reading this immediately upon delivery, I’m cheering on our Pacers as we tip off against the Knicks at home, in the playoffs.

My childhood was defined by this rivalry. Reggie Miller jawing with Spike Lee. Eight points in nine seconds. 

Even my international friends and teammates perk up when I mention it.

There’s something electric about a city that wakes up to legacy and goes to bed with the future… racing forward and rising up.

Indy, you showed up today.

❤️ kyle

On Becoming Unemployable Overnight

I don’t usually write about tattoo styles in this newsletter.

But every now and then, I want to spend time recognizing great creative—especially when it stops me in my tracks.

Recently, I came across a style called MexoMexo by Italian tattoo artist Vincent Zattera. One half of the tattoo is fully colored. The other half is just the outline. It’s clean, deliberate, and in-progress.

That tension between what’s complete and what’s still becoming is life.

Parenting. Leading. Building. Figuring things out as you go. Some parts are sharp and fully formed. Others are rough sketches, still taking shape.

We like to present the polished version. The full color. But the outline is just as real. Maybe more.

The MexoMexo style doesn’t try to hide the unfinished parts. It makes them part of the art.

So, hopefully Vincent will take me under his wing at some point in the near future in Rome. I’ll be there because that’s the kind of story I want to wear.

On Becoming Unemployable Overnight

A few days ago, I read a post from someone who has been in IT for over a decade. No performance issues. Solid references. Laid off in January. It’s now May. They’ve had one interview.

And then the zinger, “How did I become unemployable overnight?”

I’ve heard the same thing from friends in marketing, product, and sales. Talented people. Experienced leaders. Folks who used to get recruiter emails every week. Now? Silence.

I see this from the hiring side, too.

At Docebo, we opened a VP of Product Marketing role. We had over 2,000 applicants. Let me repeat that: two thousand.

And it’s been one of the hardest parts of the job, trying to manage expectations with that many people. I try to read everything I can. I try to respond when it makes sense. I try to validate when someone goes the extra mile.

But the reality is: you can’t get to everyone.

The job market is overwhelmed, and I don’t mean just the candidates. Hiring managers, recruiters, founders, and everyone is struggling to keep up.

So what do you do if you’re on the other side of this?

Here’s what I’ve seen work, and what I’ve appreciated most from candidates:

1. Be specific.

“Open to work” isn’t helpful. I want to know what you do well, what kind of company you want to work for, and what problems you love solving.

Example: “I’m a product marketer specializing in messaging and competitive intel. Looking for a Series B-C company focused on PLG. Bonus if your ICP is technical.”

Now I know who to forward that to.

2. Follow up—but make it count.

A thoughtful message goes a long way. A teardown of our product. A point of view on our positioning. A Loom video with your thinking. It doesn’t guarantee anything, but it shows me how you work and what you bring to the table.

And yes, I’ve hired people who’ve done this.

3. Fit still matters.

Being proactive gets you on the radar. But it doesn’t override the role’s expectations. You still have to match the needs of the job. That part hasn’t changed.

There are no shortcuts here. But there are ways to stand out.

This market is hard on everyone. Candidates feel like they’re shouting into a void, hiring teams feel like they’re drowning, and everyone’s trying to manage expectations that feel increasingly unrealistic.

And yet, people are still getting hired. Companies are still building teams. You just might have to work a little harder to be seen.

You didn’t suddenly become less valuable. You’re just stuck in a system not built to see you.

Keep going.

On “Just a Sec,” The Hardest Habit to Break

“Just a sec.” That’s the phrase I hate the most as a parent.

It’s the automatic response when one of my kids asks me to play, and I’m mid-email. Or when we’re cleaning up dinner and I glance at Slack, I should probably respond to that quickly. Just a sec. Just a sec. Just a sec.

Adam Schoenfeld and I discussed this on this week’s episode of Revenue Diaries. It is hard to be fully present when your brain is still chewing on a product update, a broken process, or a board meeting.

We didn’t solve anything. There’s no magic answer here. But damn if it didn’t help to talk about it.

Adam’s building Keyplay, his second or third or maybe fourth startup depending on how you count. He’s a dad. He works from home. And like most of us, he’s just trying to balance the ambition that drives him with the family that keeps him grounded.

We talked about presence, parenting, and how legacy has nothing to do with exits or revenue and everything to do with what your kids remember about you. He talked about the way his grandfather shaped his life through golf, fishing, and quiet lessons on how to live well. He talked about how his daughter is learning to sell on Etsy. He also talked about how sometimes the best thing you can do is not give feedback.

One of the lines that stuck with me was this:

“I don’t think about legacy. I just hope my kids take one good thing from me.”

Same. If I can pass on one thing that sticks, I’ll feel like I did something right.

There’s no blueprint for being a founder, executive, or parent. It’s a lot of screwing up, apologizing, adjusting, and trying again. But conversations like this remind me that we’re all figuring it out as we go.

Listen to the full episode if you need a break from the hustle and want to remember what matters.

Thanks, Adam.

On We Don’t Get the Moments Back

The hardest part about being a parent is wondering whether you’re doing a good enough job. 

I think about it constantly, and even write about it, but I spent a little more time dealing with my internal strife after reading a post from Dave Gerhardt about being present. He was at the pool with his daughter when another dad, there with his teenage kid, walked by and said, “Enjoy it. She barely wants to hang out with me anymore.”

It’s the number one thing I hear from most parents with older kids. 

“It goes fast.”  “Enjoy the little years.” “You’ll miss this someday.”

And yet, I’ve been the dad on his phone during storytime. I’ve said “just a sec” more than I can count. I’ve stared at a screen instead of watching the goal, or the made-up story they were proud of.

Hell, I’m writing this newsletter in my office on Sunday morning while my family is downstairs watching a show or playing a game. 

It’s okay, but it’s important to remember:
We don’t get time back.
We don’t get the summer day back.
We don’t get that one flag football game back.
We don’t get bedtime back.
We don’t get the walk to school back.
We don’t get the hug back.

Presence isn’t just a nice-to-have. It’s the whole game. But being present is also hard, especially when you’re tired, stressed, distracted, or trying to keep up.

And as it relates to my personal story, it’s part of the reason I cut alcohol. The “fun juice” deadens the moments. It dulls the edges of your awareness. It slows your response time to the stuff that matters. And when you string enough of those moments together, it adds up to time you don’t remember or weren’t really in.

So what do we do?

We stop chasing perfect.
We say yes when they ask us to play.
We put the phone down.
We cut the drinks.
We give five minutes of complete attention instead of 30 minutes of half-presence.

Because the metrics that matter won’t show up in a dashboard. They’ll show up when your kid says, “Remember when we…” and you actually do.

That’s the version of me I’m trying to be. The one who was there. Really there.

Because we don’t get that moment back.