Revenue Diaries Entry 43

Thursday morning. I’m sitting on a call, and I got one of those calls from my wife. Well, you know, an actual phone call. When it’s an actual phone call, you know it’s serious. Our oldest had been pushed to the ground at school after some words with another kid. Mild bullying. 

By the time I got home from the trip, he was already asleep, and I braced myself for what the next morning would bring. 

I thought Friday morning was going to be a doozy. It was going to be filled with consternation and whining about not wanting to go to school. Instead, it became a reminder of something I too often forget: kids are resilient in ways we don’t give them credit for. 

When he got up, I sat him down at the kitchen table. He looked nervous, but calm. And honestly, he was more concerned with what his brother was watching on the TV than what I was about to say. I told him, “It’s okay to be scared. It’s also important to be brave. You’ve got to face obstacles and problems instead of running from them.” 

Well, that’s probably what I said, with less eloquence than what I’m recalling, but either way, he nodded. No complaints. No, “Dad, I don’t want to go to school.” No whining or whimpering..

And then he stood up, ate his breakfast, strapped on his backpack, and rode his bike to school like it never happened. Courage can be a variety of different things and examples. Sometimes it looks like eating cereal, hopping on a bike, and pedaling to class.

Of course, as a parent, the temptation is to swoop in and protect. But I knew that’s not what he needed. Growth comes when we give them space to face the challenge themselves. My wife suggested he talk to the school therapist, and when the principal asked, he said yes. That simple yes meant more to me than any conversation I could have forced.

There are nights I wake up thinking I’ve failed as a parent. But then moments like this prove otherwise. I’M NOT FAILING! The fact that he wanted to work through his feelings instead of ignoring them is progress. 

And it’s a good reminder for all of us: resilience isn’t about avoiding fear or pain. It’s about showing up. It’s about creating an environment where people feel safe enough to ask for help and brave enough to move forward on their own.

♥️ kyle

On What It Really Takes to Pull Off An Amazing Event

It’s extremely hard to produce an event that actually brings people together in a meaningful way.

I don’t mean different for the sake of being different. Not the “57 speakers in 2 hours” format. Not “no conference rooms allowed.” Not the no-name tags or awkward silent discos.

I’m talking about intention. About prioritizing how people feel over everything else. Because at the end of the day, the only thing that matters is the experience you create for the attendees. 

As a marketer, the only thing that makes you relevant is the experience. 

This week I was in Jackson Hole, WY for Highline, a conference hosted by UserEvidence. And damn, did the team pull it off. I mean, it helps that it’s hosted in a beautiful location, but if you’re wondering what it takes to build ane vent that people can’t stop talking about, here’s what I say, and what attendees shared: 

Build Connection Before the Content

Most events cram in sessions and keynotes before people even know each other’s names. Highline flipped the script.

Day one wasn’t about content marketing, frameworks, or demand gen. It was filled with experiences - horseback rides, whitewater rafting, and hiking. People spent time together as humans first, which made the content that followed the next day infinitely more impactful and interesting. 

As one attendee said: “2/3 time for connections, 1/3 for content.” That ratio might just be the new gold standard.

Pick a Setting that Encourages Openness

Events usually drain introverts and overwhelm extroverts. Highline’s setting, under the Tetons, on rivers, under the stars, created space to breathe, reflect, and actually enjoy being there.

One marketer said the setting reminded them there’s more to life than tech stress and changing channels. That matters because so many of us in this industry are operating under constant pressure. Highline gave people a reset. And damn, I needed one. 

Real Stories Over Frameworks

I absolutely hate the PowerPoint Olympics. So instead, people shared failures, experiments, and stories that matter because they were real! 

From Jen Allen-Knuth explaining the “WeWe problem,” to Devin Reed reminding us “Too Long, Devin Reed” is a mantra marketers should live by, to Silvia Valencia and me sharing the realities of AI experimentation, people left with insights they’ll actually use.

As one person said: “Corporate polish melted away, and we connected on the realest of levels.”

Keep it Small, Intentional, and Human

Mark Huber, VP of Marketing at Highline, didn’t set out to fill a ballroom with hundreds of people. He wanted a curated group of smart, generous marketers who actually wanted to connect.

The details mattered:

• A full pre-day activity instead of the awkward “see you at the bar.”

• Meals that encouraged conversation, not rushing.

• Time built into the agenda to clear Slack or just sit in the sun.

And we all felt the results. Dozens of small moments where conversations shifted from “what do you do?” to “what are you afraid might be slipping away while you’re optimizing everything else?” to “I’m fearful of what’s next.” Real conversations. 

Leadership that Let’s People “Cook” 

One of my favorite lessons came from Ray Rhodes, co-founder of UserEvidence. He admitted: if Mark Huber had pitched “beer burros” in a planning meeting, he would’ve killed the idea.

But he didn’t. He trusted his team. He let them cook. And that trust created magic.

That’s true of the best leaders, and the best events: hire smart people, give them ownership, and then get out of the way.

My Takeaway

Highline worked because it wasn’t built on gimmicks. It was built on intention.

• Connection before content.

• A setting that encouraged openness.

• Real stories over polished decks.

• A curated group, not a massive guest list.

• Leadership that trusted creativity.

The UserEvidence team proved that when you focus on how people feel (about themselves, each other, and the work), they’ll remember it long after the flights home.

Events don’t have to be bigger, louder, or flashier. They have to be human. And that’s the hardest thing to get right.

On What You Can Learn From A Single 1:1 

One thing I’ve learned after close to 15 years as a leader, the best ideas for content doesn’t come from books, frameworks, YouTube, or anything else. It comes from conversations with your team. 

Every meeting you have is full of raw material that can be turned into lessons about leadership, strategy, culture, and development. If you listen closely (or have your meeting recorder listen for you) you can turn a single 1:1 into meaningful content. 

Just don’t share anything personal or problematic for your company. 

Here’s an example. I had a call with a teammate last week, and three reminders came out of it:

Feel the pain of your own decisions: When a big decision I made created some workflow confusion for the team, I told them: Don’t shield me from it. If someone’s frustrated, have them message me directly. I need to feel the pain myself. Leaders shouldn’t outsource discomfort; it’s the only way to stay close to reality and make better choices.

Empower with guardrails: I made it clear: if they have ideas, bring them. Nine times out of ten, I’ll say, “Great. Go do it.” That doesn’t mean everything is absolute chaos; it means I trust them. When people know their ideas won’t get shut down, they experiment, move faster, and own the outcomes.

Simplify relentlessly: We spent a big part of the conversation on consolidating software. Not because tools are inherently bad, but because complexity sneaks up on teams. Leaders have to be ruthless about cutting through noise. Simplification is everything. 

The bigger point here: leadership lessons show up in all parts of the day, in the daily grind from a Friday afternoon Zoom call to a quick Slack exchange. 

This call wasn’t just a “a work meeting or 1:1.” It was a reminder that HOW you listen and respond is what shapes the culture of the team. And if you pay attention, those moments also give you great stories to share with others. 

On Why I’m Tired of the Consulting Peanut Gallery

Most sales emails I receive are absolute trash, which still blows my mind in 2025. But every once in a while, a BANGER lands in my inbox. 

This email had so much rizzzzz, I had to post about it.

This one showed up after the Highline event last week, and it checked every box for me as a buyer:

• Relevance: They referenced the conference with real examples. Not scripted.

• Clear value prop: No jargon soup. Just: here’s who we help, here’s how, here’s the impact.

• Social proof: Not random logos. A relatable company with a real story.

• Momentum: They mentioned conversations already happening with my team. Felt less like cold outreach.

• Easy next step: No “60-minute demo.” Just a quick intro. Calendar link included.

• Tone: Friendly, professional, and human.

It was good. Damn good. So I posted it. And then the comments rolled in:

❌ Too long.
❌ Doesn’t scale.
❌ No one reads that much text.

Here’s the irony: I’m the buyer. I’m the one opening the email. I’m the one deciding if it’s worth a meeting. I’m the one signing the check.

And I thought it was good.

Which is why I’m so tired of the peanut gallery. The consultants and “sales gurus” who sit on the sidelines with a thousand opinions and (mostly) lackluster experience. They’re not the ones in my inbox. They’re not the ones evaluating software. They’re not the ones moving budget around to make room for a solution.

DISCLAIMER: Some consultants have a ton of experience, but I still vehemently disagree with them. 

That’s me. But I’ll give them one thing: it’s hard to scale extremely personalized content. 

And here’s where the real balance lies:

• Personalization doesn’t mean writing a novel. It means showing me you know something real about me, my company, or my world. The example above wasn’t “overwritten.” It was relevant.

• Scale doesn’t mean stripping out the human. AI, templates, and sequences are powerful, but if they erase the context, you’ve just automated mediocrity.

• The sweet spot is repeatable personalization. Build frameworks and data sources that let reps personalize quickly: shared event attendance, industry pain points, and social proof mapped to personas. Not every email will be a masterpiece. But every email can feel like it was written for someone, not everyone.

So yes, scalability matters. But it’s useless if what scales doesn’t resonate with buyers. The peanut gallery will keep talking and shit-posting. That’s what they do.

But the only feedback that matters is from the person who can say “yes.” It’s not the consultant writing the check; it’s me.