I cannot believe it’s been over a year since I started writing this beautiful old newsletter. Big thank you to everyone who subscribed, read, and replied. I love all of it. It makes me a better marketer, partner, and father. 

So thank you. You made 2025 a pretty damn enjoyable year. 

I didn’t start this year with any type of thesis. I didn’t have a grand plan for what I wanted to accomplish. I just did the thing, and it was an interesting year to say the least. 

New homes. New jobs. New experiences. 

A lot of new, but also a lot of the old stuff. And honestly, no outline or grand plan for the themes and content. I just took it day by day, campaign by campaign, night after night. So, I prompted my trusty friend, GPT-5000000, to give me an overview of what it believed I learned in 2025 across leadership, marketing, and parenting… ya know… being human. 

I did not edit the output from GPT-5000000, but I did add my thoughts in red. 

That’s the first entry in this edition of the Revenue Diaries. The second entry? My top-read article of the entire year, #30:

♥️ kyle

What I Think Kyle Learned in 2025

An outsiders view

Watching Kyle move through 2025, the most obvious shift wasn’t professional. It was internal. The year didn’t make him louder, faster, or more ambitious (ahhh thanks, I think). It made him more precise about where his energy goes and more honest about what actually costs him.

Here’s what stood out.

He learned that credibility comes from ownership.

One of the clearest lessons Kyle learned this year is how fragile performance becomes when it’s mistaken for credibility. He’s spent years learning how to sound prepared, how to frame progress, how to manage a room. Those skills still matter. But 2025 exposed their limits (yes, yes it did).

What actually builds trust is ownership. Ownership of the number. Ownership of the tradeoff. Ownership of the part that didn’t work and the part that might not yet.

In boardrooms and leadership meetings, the pattern became hard to ignore. Energy drops when language turns vague. People lean forward when the story is clear and grounded, even if the outcome isn’t perfect. Over time, Kyle learned to resist performing certainty and instead make his thinking legible (huh?). What we know. What we’re testing. What we’re choosing not to do right now.

That shift changed the quality of the conversations. It also changed how he felt walking out of the room. Less defended. Less hollow. More aligned with the work as it actually was.

I still don’t understand what “resist performing certainty” means but it’s 100% true I adjust my communication to be more data and less emotional. It had a MASSIVE impact on how I felt in e-team meetings, board meetings, and executive planning. 

He learned revenue alignment is a relationship discipline above all else.

That same discipline showed up in how Kyle thought about revenue. Earlier in his career, revenue alignment felt like armor. Something marketing needed to survive scrutiny. In 2025, it started to feel more like a shared operating system (which is MASSIVELY IMPORTANT, even though I wouldn’t use the term “shared operating system”).

When expectations are explicit and the math is visible, suspicion has less room to grow. (Better said: Know your sh*t) Pipeline models, forecasts, and conversion rates stopped being reporting artifacts and became tools for coordination. Not proof. Not protection. Coordination.

The real lesson wasn’t about dashboards or attribution models. It was about relationships. Marketing, sales, finance, product. When those groups share the same language about success and risk, the work calms down. Disagreements still happen, but they’re about choices instead of blame.

That calm isn’t accidental. It’s earned through repetition and clarity. Through returning to the same agreements often enough that trust stops needing to be negotiated every quarter.

I can’t stress this point enough. A shared language supported by a shared reporting model is FOUNDATIONAL to a healthy, aligned GTM team. If marketing, sales, CS, and product are all reporting out of different dashboards, it will always and forever be a royal sh*t show. 

He learned that taste is a leadership team’s responsibility.

As the year unfolded, Kyle kept returning to the idea of taste. Not as creative preference, but as judgment. Taste shows up in what you choose to ship and what you choose to leave out. It shows up in how much friction you’re willing to tolerate in service of something lasting.

In a world where tools make it easy to produce more, taste becomes the constraint that keeps the work from dissolving into sameness. (ooooo I like this. So true). 

This became most visible in moments where restraint felt uncomfortable. Killing a feature that distracted from the core story. Slowing down a launch to fix the last ten percent. Saying no to an idea that was clever but hollow. These decisions rarely look impressive in isolation. Over time, they compound into coherence. Customers feel it. Teams feel it. The brand becomes clearer, not louder.

Kyle learned that taste isn’t decorative. It’s structural. And when leaders avoid owning it, someone else will make those decisions by default. Usually badly.

I’ll take this to my marketing grave. I believe good taste is the responsibility of the leadership team. If the leadership team doesn’t understand what it means to have good taste in how you market, promote, and sell your product, you are in for a world of pain. And FWIW, I think it’s tough to learn “good taste.” You either have it or you don’t. 

He learned that his head trash wears a professional costume (a little over-the-top but I agree)

Kyle didn’t struggle with impostor syndrome in the obvious way this year. The fear wasn’t about belonging. It was about performance. About not wanting to look careless, wrong, or premature.

What he learned is that his version of fear prefers silence. Waiting. Overthinking disguised as responsibility.

A new job tends to pull out the loudest vulnerabilities. The head trash will scream and force you to overthink. Don’t let it. 

The shift wasn’t eliminating the noise. It was learning to recognize it. Naming it. Acting before certainty. Shipping thinking instead of waiting for polish.

From my view, this was one of the most consequential lessons of the year. Kyle learned that credibility doesn’t come from having the cleanest answer. It comes from being willing to show the work in motion.

He learned that AI changes the shape of work, not the responsibility.

AI hovered over all of this. It changed how fast teams could move and how much surface area one person could cover. It flattened roles and exposed where work had been padded by process rather than purpose. (I’m particularly proud of this post “How AI is reshaping marketing teams”) 

But it didn’t absolve anyone of responsibility (no way). If anything, it raised the bar. When execution gets cheaper, judgment gets more expensive. Leaders are still responsible for deciding what deserves attention and what doesn’t.

What AI did provide was speed. Speed to test. Speed to learn. Speed to see where thinking was weak. The teams that benefited most weren’t the ones chasing every new capability. They were the ones willing to run small experiments and name the results honestly. Some worked. Most didn’t. The value was in the learning loop, not the artifact.

That distinction mattered. It separated curiosity from theater.

I’m very proud of what the marketing team accomplished this year related to our AI tooling and testing. We have invested a ton of energy and it’s paid off. The best example? Our work in AEO. And who better to tell you about it than the great Kyle Poyar: How to Turn GPT into Your Best Pipeline Source) 

He learned that meaning comes from presence.

Running parallel to all of this was a quieter education happening at home. Parenting has a way of collapsing abstractions (understatement of the year). Kids don’t care how busy you are or how good the quarter was. They care whether you’re present.

This year made it harder for Kyle to ignore how easily momentum crowds out attention. How often optimization shows up when patience is what’s actually needed.

Sobriety sharpened that lesson. Without the buffer, there was nowhere to hide from discomfort. The upside was clarity. Not the dramatic kind. The steady kind. Better sleep. Better mornings. More capacity to sit with a hard thought without rushing to resolve it. Writing became easier because his head was quieter. The work benefited from that quiet too.

There were transitions that landed harder than expected. Standing in an empty house after a move. Watching his kids ride off without looking back. Those moments carried a strange mix of gratitude and loss. They made it clear that progress doesn’t always feel like forward motion. Sometimes it feels like letting go of a version of yourself that worked for a long time.

This interpretation was 100% on point. No notes. 

What I believe Kyle is carrying forward. 

By the end of the year, Kyle wasn’t chasing new answers as much as refining old ones.

• Credibility comes from ownership.

• Alignment comes from shared language.

• Taste comes from restraint.

• Tools change the shape of work, not the need for judgment.

• Meaning comes from presence.

None of this feels finished. That’s probably the point (it's 100% the point). 

The work continues, just with a little less noise and a little more intention. The clearest throughline in what Kyle learned in 2025 is that clarity isn’t something you declare. It’s something you earn slowly, by staying close to the work and honest about the tradeoffs.

That feels like enough to carry forward.

Couldn’t have said it better myself. Here’s to a great 2026! 

MY MOST READ: On There’s No Substitute for Context

Six weeks. Sixteen flights. Three countries. Twenty dinners.
One crash course in becoming the CMO of a global (public) company.

Most executives onboard. I decided to on board. (Yes, I haven’t lost my creative flair.)

The past six weeks have been a blur of time zones, team meetings, and solo work crammed between flights, from our customer conference in Orlando, to dinners in Milan, to sunrises in Maui.

Here’s the itinerary:

• Week 1: Orlando for Inspire, our customer conference

• Week 2: Atlanta and Athens, GA, for team meetings

• Week 3: Back home to Indianapolis to catch my breath

• Week 4: London for LTUK and to meet EMEA customers

• Week 5: Milan and Biassono for internal planning and our board meeting

• Week 6: Maui for President’s Club

The punchline? It was exhausting. And 100% worth it.

Because when you’re new in a role (especially an executive one), there’s no substitute for context. And context comes faster when you show up in person.

Here’s what six weeks on the move taught me:

1. Nothing replaces face time

Slack is fast, and Zoom is functional, but trust moves faster in person. A hallway chat in London, a long dinner in Milan, a beachside coffee in Maui, these moments build relationships.

In-person doesn’t scale, but it compounds.

2. People want permission to simplify

When companies move fast, complexity creeps in. Layers build. Processes tangle. Alignment falters. I’ve heard this again and again: “Can we just make this easier?”

The best-performing teams reduce complexity. The real leadership unlock is giving your team permission to stop overengineering and start simplifying.

Clarity isn’t a luxury; it’s a must-have.

3. Leaders have to listen before they lead

It’s tempting to jump in with big ideas especially when you’re hired to drive change.
But teams don’t follow slide decks. They follow people who listen and understand the history, context, pain points, and progress that came before them.

Listening is leading. Especially at the beginning.

4. Your energy is your message

I fully support this message because culture isn’t a slide. It’s not a quote on the wall. It’s what people feel when you walk into a room.

And when you’re six flights in and running on fumes? That energy still speaks.

Are you present or distracted? Curious or defensive? Calm or frantic?

Because people notice, they always do.

In leadership, your energy becomes your message long before you send a single email. You set the temperature, model the culture, and show people what matters based on what you prioritize, how you show up, and the tone you carry, especially when it’s hard.

That’s not pressure. It’s a privilege. One I try to treat with care.