Revenue Diaries Entry 32

Full warning: I don’t know if it’s summer, the Pacers winning last night, or just getting older—but this one’s full of self-reflection.

The Pacers beat the Knicks, and it took me straight back to the late '90s. Reggie Miller. Rik Smits. Watching games with my family like they actually meant something. I’ve been thinking about that a lot lately. How certain moments stick. How most of them don’t.

This week’s entry is about that feeling + some work stuff. Read at your own risk. :)

On Trying to Hold the Moment

I was sitting at a stoplight yesterday morning, listening to my son tell me about two dreams he had the night before. It wasn’t a life-altering moment. Nothing dramatic. But still, memorable.

And I remember thinking, I should record this.

I knew I’d want to stumble across that video ten years from now. I’d want to hear his voice. I’d want to remember how it felt in the car… windows down, coffee in the cup holder, his whole world unfolding in the passenger seat.

It’s been happening a lot lately. I’ve been catching myself trying to hit pause. To capture something—anything—before it fades. To hold onto the ordinary things I know won’t stay ordinary forever.

I try really hard to be present. But sometimes that instinct to capture is followed by a subtle sadness. Like even while I’m living the moment, I can already feel the future version of me missing it.

And I don’t want it to feel like loss or regret. But some days, it’s hard not to focus on the parts that are already slipping away. Other times, it feels more hopeful—a reminder to pay attention. To slow down. To be grateful I even noticed the moment in the first place.

It’s not just a parenting thing either. Sure, there’s something powerful (and frightening) about watching a human grow up in front of you. But this feeling applies to all kinds of moments… sitting with friends late at night, walking out of class with someone you’ll lose touch with, laughing over lunch with coworkers you’ll never work with again.

These moments feel small at the time. Until they don’t.

I keep thinking about future me.

The version of me who will someday want to rewatch that video. Trying to remember what it felt like to be here. To hear my kids talk like that. To see their faces light up when something clicks. To re-experience the sound of their voices before they change.

And even when I’m present, I still feel like I’m trying to grasp it instead of just live it.

It’s a weird mix—trying to be in the moment while also trying to preserve it. Like I’m attempting to burn it into my brain because I know how fleeting it all is.

I don’t know if it’s age, or parenting, or sobriety, or just being human. But I’ve started wondering if part of me is always waiting. Waiting for something to feel final. Or like enough. Or like the right moment to just be here.

Maybe this is what being present actually looks like—not clarity, but a clumsy, imperfect awareness that this matters… and that it’s going to slip away.

I don’t have a tidy lesson to wrap this up. I just know I’m trying and trying to notice more. To pause. And to be grateful for the feeling, because at least it means I’m paying attention.

♥️kyle

On Taking a Hot Shower

If you haven’t heard of it, Diary of a CEO is a long-form podcast hosted by Steven Bartlett, where entrepreneurs, artists, and thinkers unpack their lives and careers. Frankly, it sounds more like therapy than anything else. It’s one of the rare shows where the guest usually drops the persona. I recently watched the episode featuring Jimmy Carr and I loved his take on..

"Life has never been objectively better and subjectively worse."

Carr used the example of a hot shower. A hundred years ago, no one you admire had one. Today, it’s the default. Most of us barely register the feeling. We’ve adapted so quickly to comfort that we’ve lost the ability to notice it.

And yet, many of us feel more anxious, unfulfilled, and overwhelmed than ever.

Carr calls it "life dysmorphia." Just like body dysmorphia warps how someone sees themselves physically, life dysmorphia distorts our perception of how good we actually have it. We’ve adapted so quickly to abundance that we’ve lost perspective. Our baseline for comfort is so high that the only place left to go is envy.

And so the hot shower becomes the symbol. It’s objectively better. It’s subjectively empty. Unless we choose otherwise.

Hello, gratitude. Carr believes it is a discipline. Gratitude, he says, is the antidote. It turns the mundane into meaningful.

Here’s the trick: stand under that hot water and think about the billions of people who never had it. Let that thought interrupt the default settings of your brain.

It’s a reset button. A way to remember that running water, safe neighborhoods, and instant communication are all recent miracles. Most humans who’ve ever lived didn’t get this.

If life has never been objectively better and subjectively worse, maybe it’s time we fix the subjective part.

On Pain is Inevitable. Suffering Isn’t.

I’ve been lucky to know Scott Barker for a while now. If you don’t know Scott Barker, you should.

He recently announced that he’s selling everything he owns and traveling the world for an undetermined amount of time. Not because he’s lost. But because he’s realigned.

He’s stepping away from the endless cycle of more—more stuff, more work, more chasing, and choosing to redesign his relationship with success, fulfillment, and work itself. Launching a podcast. Exploring wellness. Building something new when it’s time but not before.

He shared a post last week about a meditation retreat he attended at the Esalen Institute, and I knew I had to write about it.

Scott shared a Buddhist parable I hadn’t heard before: the story of the two arrows.

The first arrow is life’s unavoidable pain—loss, aging, failure, heartbreak. That one’s coming for all of us.

The second arrow is the one we shoot ourselves. Rumination. Self-judgment. “Why me?” thinking. The pain we layer on top.

Scott wrote: “We can still feel the first arrow but we don’t have to shoot the second.”

Love it, because I’ve been noticing how often I’m the one reloading the bow.

This year’s been full of shifts… some small, some significant. Cutting alcohol. New job. Rethinking how I use time. Trying to be more present with my family. Saying no more often.

And yes, much of my stress has been self-created.

• I sprial after tough calls.

• I have an internal scoreboard that is never "up and to the right."

• I'll always pressure myself to be "on."

• The anxiety to hit a number that isn’t even due yet

• The thought loop after one awkward conversation

• The pressure to outperform even when you’re already exhausted

None of that is the first arrow. That’s the second. And I’ve been firing it for years. Scott’s post was a reminder that most of us are carrying weight we don’t need to carry.

And then he left us with this zinger… after just a few days off the grid, he felt more connected to strangers than some people he’s worked with for years.

That’s not a critique. It’s a reflection of how rarely we slow down, individually or as teams. We optimize, we iterate, we push. But how often do we pause?

Not for performative wellness. Just for a minute of honest inventory. Because the second arrow never fixes the first. It just keeps us stuck.

On Gaming the System Isn’t the Problem

I was in a conversation with a fellow revenue leader the other day, tossing around ideas to improve pipeline conversion.

We got into comp models, handoff processes, and redefining what counts as a “qualified” lead. And then we landed on the “issue:”

“We’re hesitant to change the criteria. I’m worried the BDRs and AEs will game the system.”

It’s a common hesitation.

You roll out a new comp plan or tweak a definition, and suddenly the fear creeps in:
What if reps bend the rules?

But let’s be real… most don’t. Most BDRs and AEs want to win the right way. They care about the craft. They care about hitting goals and helping the business.

This isn’t a people problem. It’s a system problem.

When someone games the system, it doesn’t mean the goal was wrong. It means the system wasn’t strong (or clear) enough.

And if fear of being gamed keeps you from evolving? You’re not leading the system. The system is leading you.

What is the system?

It’s not just your Salesforce instance. It’s not just attribution models or dashboards. The system is the combination of your:

• Definitions (What counts as success?)

• Accountability (Who owns what, and what happens when it breaks?)

• Visibility (Can leaders actually see what’s happening?)

• Culture (What behaviors are rewarded, tolerated, or ignored?)

You can’t build high-performing teams (across marketing, sales, and business development) without getting those four things right.

Where does it break down?

In most orgs, it’s the AE/BDR handoff where things start to fall apart.
Marketing generates a lead.
BDR takes a meeting.
AE says it’s junk.
BDR says they hit their number.
Everyone shrugs.

So, who owns the outcome? Who’s accountable when that meeting doesn’t convert? How do we know if that was a one-off or a pattern?

If you can’t answer those questions quickly and confidently, you don’t have a system. You have a scoreboard with no refs. No bueno.

Start with the system:

Align definitions across teams: Work backwards from what actually converts to revenue, not what’s easy to track. A “qualified lead” or “qualified meeting” should mean the same thing to Marketing, SDRs, and AEs.

Make conversion a shared metric: Instead of just MQLs or meeting volume, tie compensation or goals to pipeline progression or revenue contribution. If everyone owns conversion, people stop throwing junk over the fence.

Instrument visibility into behavior: Surface leading indicators, not just lagging metrics. Can you see meeting attendance? Talk time? Repeat meetings with the same contact? Abuse hides in the gaps. Make it visible.

Create feedback loops, fast: Don’t wait for quarterly reviews to figure out something’s off. Set weekly deal reviews, AE–SDR standups, and manager call listening. Fix issues in days, not months.

Reward what matters: Celebrate the behaviors that lead to trust, not just volume. A rep who books fewer—but higher quality—meetings should be lifted up, not penalized. That sets the tone.

Aggressive goals aren't the problem. Weak systems are.

If you're avoiding stretch targets because of a few bad actors, you’re solving the wrong problem. Build a system strong enough to surface manipulation early, and clear enough that nobody needs to ask what success looks like.

Bold goals and accountability can (and should) coexist. But only if you lead the system, not just the scoreboard.