Revenue Diaries Entry 37

I love summer nights in Indiana. There’s a stretch of calm, sometime after 8:30 pm, when the sky decides to show off, turning lavender with hints of orange, and a feeling of contentment…

You’re still damp from the pool. The concrete is warm underfoot. Someone’s dad is talking about the Reds (or travel baseball, take your pick). The older kids are trying flips off the diving board. You hear the lifeguard’s whistle and an impatient “Walk!” with laughter echoing across the water. 

It’s dusk, but no one’s in a hurry to leave. This is summer at the neighborhood poo, and it’s magic.

It’s not just about swimming or sunscreen or overpriced Bomb Pops. It’s the togetherness. A neighborhood in motion. A hundred different families writing tiny, overlapping memories. There’s something about this kind of shared space that reminds you how good it feels just to be somewhere with other people. No agenda. No screens. Just light fading into night and the sound of water.

As a kid, these nights felt infinite. As an adult, they feel fleeting. 

But they still matter. Maybe even more because the world feels pretty chaotic and screwed up. And standing at the edge of the pool, trying to catch the right photo of your kids jumping off the high dive, you remember: not everything has to be so complicated. 

I’ll take this to the grave… the most meaningful moments are the ones you don’t try to manufacture. You just let them happen.

So here’s to Indiana summer nights or wherever you might experience the lavender light. The kind that leaves chlorine in your hair, a smile on your face, and a gentle ache in your chest because you already know you’ll miss it before it's even over.

♥️ kyle

On the Most Honest Conversation I’ve Had About Marketing & Meaning

There’s a moment about halfway through my conversation with Drew Brucker where I realized we were discussing much more than brand versus demand.

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Sure, that’s how it started. Drew and I had a bit of back-and-forth on LinkedIn about brand marketing, measurement, and how to justify creative work within B2B SaaS. But like most good conversations, it turned into something deeper.

Drew is the Head of Brand and Content at Goldcast, but that’s just the day job. He’s also a photographer, a former VP of Marketing who walked away from the traditional ladder, a dad to twin girls, and someone who’s spent a lot of time wrestling with the same career questions many of us are afraid to ask out loud.

Like this one: What if I don’t want to keep climbing the ladder?

The Break (That Wasn’t Really a Break)

At one point, Drew stepped away from a full-time role to explore what AI could mean for creativity. But like most of us, what he called a break was anything but. He was consulting, launching products, building custom brand visuals using Midjourney, and selling enough to prove that his curiosity had real business value.

But what stood out to me wasn’t the projects. It was the intention behind them.

Drew wanted to test a version of work that was more aligned with his creative instincts: less spreadsheets, more storytelling. He wanted to learn, to build, to be curious again. That requires courage. Especially with two-year-old twins at home.

“I had to figure out whether I wanted to keep leading teams or if I was better off going deep into the work itself,” he said. “I realized I was spending more time playing mouthpiece than actually creating anything. And that wasn’t me.”

Sound familiar?

The Solopreneur Myth

Let’s just say it out loud: going solo isn’t easy. And if you're a parent, or a partner, or someone who likes health insurance… it’s a lot.

Drew was clear about how we dealt with the pressure, the self-doubt, and especially the income anxiety. “The first six months were hard,” he told me. “But by the end, I had figured out how I worked best.”

That’s the key: he wasn’t chasing someone else’s playbook. He was writing his own. And he wasn’t doing it for likes or virality. He was doing it because he knew he was best served by following what actually energized him.

Which brings us back to the work.

Brand Is the Work

I’ve been around the block enough to know that “brand” still makes a lot of operators roll their eyes. But Drew’s take is the most compelling I’ve heard in a while:

“Brand is a controllable moat. Features can be copied. Ads can be outbid. But brand? It’s how you get on the shortlist. It’s how you get remembered.”

He’s right. We often over-index on attribution and under-invest in brand and then wonder we are dealing with a leaky bucket of $$$, and conversion rates dropping.

He’s not arguing against revenue accountability. Neither am I. The goal is still the goal. But creative execution (real brand strategy, not just lipstick and logo updates) is how you drive long-term demand.

That said, Drew’s approach is practical. He knows you have to fight for resources. He knows leadership still expects a return. But brand isn’t fluff when it’s done with intent. It’s leverage. It’s the thing that makes demand creation actually work.

Designing a Life That Fits

I asked Drew the same question I ask every guest: How do you think about balance?

He didn’t have a perfect answer (none of us do), but he shared something I’ve heard more and more from guests this season: “I just don’t want my kids to remember me always being on my phone.”

Me neither.

We discussed the power of work blocks, putting the phone in another room, and being more intentional with our time. But what stuck with me was this:

“You don’t always have to be everything. Just be.”

That’s hard in a world that rewards constant motion. But it’s probably the most valuable lesson from our entire conversation.

The AI Shift

Oh… and yes, we did talk about AI. A lot. Drew is deeply embedded in this space, and his point was simple: “If you’re not experimenting with AI right now as a marketer, you’re going to get left behind.”

He uses AI every day to design assets, iterate faster, troubleshoot problems, and even create digital art that has been featured in international exhibits.

I told him we’re living in the early scenes of Her and we both laughed. But there’s truth to it. The best marketers I know are learning, adapting, and shipping faster because of these tools. Not despite them.

When I asked Drew what he’d do if he had a year off, his answer was quick:

“I’d make art.”

Not because it’s profitable. But because it fills him up.

That’s the lesson. Whether it’s brand marketing, parenting, solopreneurship, or photography, if you’re not doing at least some of the work for yourself, it will eventually show up in your output and life.

So here’s the question I’ll leave you with: What’s your version of making art?

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