Revenue Diaries Entry 34

Happy Father’s Day to all the dads out there. Hopefully, you’ve had a good day with your Goodr sunglasses and Vuori shorts. I know I have because I’ve had the chance to be a little reflective this morning as I sip this delicious coffee and take inventory. Or maybe the better word is score. 

How am I doing as a dad? As a leader? What about how I’m evolving in my career? AI is changing everything, am I keeping up? 

I know, I know. BIG QUESTIONS for a Sunday morning (or evening when you receive this). I’ll get to the AI part (evolve or die) in the second part, but let’s start with being a father, a parent. 

I’d LOVE to believe that most days are wins, but my head always tells me different. I could have done better, or said something differently. Reacted with more patience. Smiled more. You know the drill, you feel it too. 

But I keep showing up. And maybe that’s the point. Parenting is rewarding, sure but mostly because it’s damn difficult.

The beautiful thing about the internet is we can share what we’re learning. And sometimes those stories help make sense of the work we’re all trying to do.

So here’s one of mine.

A couple of weeks ago, my kids went to baseball camp at Butler University.

My youngest has played before, but my oldest never really has. But after watching their friends play in an “official” game one night after soccer, they both asked if they could try a summer baseball camp.

So we signed them up.

Since this was more of a “test,” we didn’t go out and buy a bunch of gear. It was a short, three-day camp. They had gloves, but we didn’t have the right bats. No official gear. My oldest wore football cleats.

Well, my dear friends, the kids noticed. And like some kids do, they were a little cruel. 

They didn’t pick him. Made fun of his shoes. He didn’t get accepted like he usually does at basketball or soccer camp.

It was tough. 

Thank the high heavens that I have a partner who has made it a priority to talk openly with our kids and build a relationship of trust. My wife had the first conversation with him.

She really had to pull it out of him and give him space, make room for him to open up. And he did. I’m so grateful for that. It’s one of those reminders that parenting really is a team sport.

Because I’m less tactful than my partner, I found a moment later. One of those rare windows where he wasn’t distracted or defensive. And I told him about the time I went to baseball camp when I was his age.

Same story, different decade. I don’t remember if I had the right gear, but I do remember not being accepted and feeling it. 

He didn’t say much. Just kind of nodded. Then moved on to something else. No hug. No breakthrough. But I know he heard me.

And it reminded me of a lesson from one of my favorite books, Do Better Work by Max Yoder: “Vulnerability isn’t weakness, it’s a show of confidence. It helps teams trust faster and grow stronger.”

That applies at home too. 

I’m learning that being a dad isn’t about solving everything. It’s about showing up with stories and being human. Letting your kids know you’ve been there, even if they don’t say much back.

Sometimes they don’t need advice. They just need to know they’re not alone. That’s the work. That’s love. That’s fatherhood.

♥️kyle

On Reinvention Isn’t Optional: Evolve or Die

Okay. Let’s talk about the robots because AI has been forcing many of us to think a lot about reinvention. Me included… clearly.

Not the kind you plan for. Not the kind you sprinkle into a five-year career roadmap (who has a career roadmap anyway?). I mean the kind that shows up without warning because the world around you has changed so fast, you either adapt or get left behind. 

You either evolve or you die. That’s the moment we’re living in now.

We’re not just watching a new technology take shape. We’re in the middle of a work revolution. The way we write, sell, design, code, manage, and lead is being rewritten in real time. 

And it’s exhausting because the pace is relentless. The gap between how most of us used to work and how we need to work is getting wider by the week… day… hour.

Honestly, it doesn’t matter where you are at in your career. It doesn’t matter if you love technology or can barely tolerate it. AI is changing the way we work and the longer we wait to engage with it, the harder the reinvention becomes. 

And I want to be very, very clear. This isn’t about being trendy. I’m not going to wax poetic about the “wave of AI.” 

It’s more about staying useful, curious, and encouraging. It’s about continuing to grow, even when it’s so much easier not to. I guess that’s life. 

The rules are changing overnight. 

I wasn’t working in the 90s and early 2000s when the internet started to change everything. I was in high school. But even then, I could see it happening. You can FEEL massive change like the .com boom. 

The world was shifting. People began using email at work. Companies were building websites for the first time. Entire industries were being redefined by a technology that most of us barely understood.

I guarantee people were scrambling to keep up. I’m sure some learned HTML, built early digital businesses, launched online brands, and careers. Others hesitated. They didn’t see the urgency. They waited. And a few years later, it was crystal clear: the world had moved on without them. 

That was the first time I witnessed what happens when the rules of work change. This moment with AI? It’s the same pattern, only 100x faster.

Now? Back then, you had years to adapt. Now? The tools change weekly. The expectations shift monthly. And what felt like “future-state” six months ago (hell, a month ago) is already being built into workflows across every function.

My fellow readers, we all know this is not a temporary phase. It's not a trend. It’s a new operating system for work. It’s a new mindset. It’s rewriting the rules in real time. 

And it’s stressful AS HELL. 

So, let’s go with a classic. What got you HERE won’t get you THERE. 

Reinvention is fun to talk about. “Welcome to my TED talk, let’s wax poetic about reinvention.” But then, we are all faced with the reality that we HAVE to do it. 

When you’ve been in your role, your industry, or your lane for long enough, you start to develop muscle memory. You know what works. You’ve failed enough times to have a decent playbook. You’ve earned the trust. You’ve built a reputation. 

And then a moment like this shows up and quietly whispers, “Are you willing to start over?” 

Not all the way, of course. You still bring your experience, judgment, and leadership. But you do have to shed some of the certainty. Some of the control. Some of the comfort.

That’s not easy. Especially when your strategies still work. For now.

But the most dangerous mindset is: “What I’ve always done will keep working.” It might. Until it doesn’t. And by the time you notice, the gap is hard to close.

And it’s important to remember, age isn’t the issue, but it’s not irrelevant either. 

Reinvention is hard for everyone. But it gets so much more complicated as you get older. 

When you’re earlier in your career, change is expected. You’re still learning, still building. You don’t have much to lose, and you’ve got plenty of time to bounce back.

But mid-career? You’ve got things to protect. A reputation. A rhythm. A team. A family. A calendar full of responsibility.

And reinvention starts to feel expensive? 

You think twice before looking foolish. You hesitate to adopt a tool you don’t fully understand. You avoid the beginner’s discomfort because you’ve worked hard not to feel it anymore.

I’m going to type this one more time… 

You avoid the beginner’s discomfort because you’ve worked hard not to feel it anymore.

But guess what? Irrelevance costs more than discomfort. Success is not an excuse to stop evolving. It’s a reason to evolve faster and try harder. 

Let’s get uncomfortable. 

This isn’t about turning your life upside down. It’s not about switching careers or chasing the latest AI robot, Lovable, vibe-coding trend.

It looks like experimenting in the middle of your real, messy day-to-day. For me, that means: 

• Using ChatGPT to gut-check messaging or sharpen a headline before I send it to the team.

• Building prompts to summarize feedback from customer interviews, Gong calls, or internal notes. 

• Playing with tools like TOFU, Lovable, and others, so I can understand what modern GTM stack should look like. 

• Blocking time to test AI workflows because I understand the long-term payoff

• Following people doing it right: Jordan Crawford and Kiernan Flanagan are my go-to AI experts

It’s less about “mastering” AI and more about staying in motion. Staying curious.

I don’t have this perfectly figured out. No one does. But I’m in the damned game. And I’m trying as hard as possible to model it for my team, because if I don’t stay close to the shift, I’ll wake up one day and realize the gap between how I think we work and how we actually work is too wide to cross.

You don’t have to be the most technical person on the team. You don’t have to chase every tool.

But you do have to move. You do have to try. You do have to participate in your own reinvention.

And as a leader, you have to lead. The people around you are watching how you respond to change. Are you curious? Dismissive? Quietly panicked?

They take their cues from you. So when you lean into learning, they feel safe doing the same. When you model experimentation, they follow. When you admit you don’t have it all figured out, they trust you more, not less.

Reinvention isn’t just a personal decision. It’s a cultural signal.

And the best thing leaders can do right now? Normalize exploration. Reward risk. Celebrate people who raise their hands and say, “What if we tried something different?”

It’s all exhausting and exhilarating at the same time. It’s not about becoming someone new. It’s about remembering you’re not done yet. You’re still capable of learning. Still capable of growth. Still capable of surprising yourself.

That’s the mindset that will carry us through the next wave of change. That’s the mindset that will keep you relevant, sharp, and fulfilled. So wherever you are in your career, start small. Start curious. Start now.

Because reinvention isn’t optional. And it’s never too late to begin again.

On Embracing the Mixology of Life: Lessons from LeTísha Shaw

Okay. Let’s talk about the robots because AI has been forcing many of us to think a lot about reinvention. Me included… clearly.

Failure is a loaded word. Some people avoid it entirely, others treat it as a badge of honor. But for LeTísha Shaw, a transformational marketer currently at UserTesting, it's not even part of her vocabulary. Instead, she sees every setback as just another ingredient in the recipe of life—one that's best embraced with curiosity and a dash of experimentation.

I recently sat down with LeTísha for an episode of the Revenue Diaries podcast. From her nonlinear career path that zigzagged from mechanical engineering to product marketing, to her wide array of hobbies and passions—ranging from quantum physics to gluten-free baking—we explored the many layers that define her remarkable journey.

Failure Isn’t the End—It's Just a Data Point

Early on in our conversation, LeTísha shared a powerful insight: “Failure is not a word that I use very often. It's not even a word that comes up in my negative self-talk.”

Damn straight. How often do we let the fear of failure limit our growth? Instead of viewing moments of setback as endpoints, LeTísha reframes them as data points… opportunities to learn, pivot, and refine. Whether it’s navigating career transitions or perfecting a gluten-free Belgian waffle recipe (delish), experimentation is core to her approach.

The Nonlinear Path to Success

LeTísha’s career path didn’t follow a straight line, and she's better for it. Starting in mechanical engineering, she later pivoted into marketing, eventually shaping early digital strategies at Disney and eventually product marketing at UserTesting.

This winding path taught her something important: authenticity and adaptability are far more valuable than rigid adherence to a plan. The result? She's built a career marked by growth, curiosity, and continuous reinvention.

Parenting with Authenticity

As we shifted our conversation toward parenting, LeTísha shared her thoughtful approach to raising her daughter. She emphasizes authenticity over perfection, teaching her child the value of genuine self-expression.

"I want her to embrace growth without chasing perfection," she said. It's a parenting style born from LeTísha’s own experiences—accepting herself fully, flaws and all, and empowering her daughter to do the same.

Becoming a Mixologist of Life

One of my favorite moments came when LeTísha described herself as a “mixologist of life.” Whether she’s mastering salsa dancing, experimenting with hot yoga, or discovering bath bomb hacks for boosting productivity, she's constantly mixing elements from diverse parts of life into something uniquely fulfilling.

This joyful chaos isn’t accidental. It’s intentional, rooted in curiosity and a commitment to personal growth. LeTísha isn’t just living life—she’s crafting it, intentionally blending her passions, experiments, and interests into something greater than the sum of its parts.

Lessons from the Mixology Lab

As marketers, leaders, or simply humans navigating our paths, there’s a lot we can learn from LeTísha’s philosophy:

• Redefine setbacks as learning moments rather than permanent labels.

• Embrace nonlinearity in your career and life choices; it opens doors to unexpected opportunities.

• Prioritize authenticity over perfection, both personally and professionally.

• Mix and match diverse experiences, interests, and ideas to create a fulfilling, holistic life.

Life, after all, is an experiment. And as LeTísha shows us, we’re all capable of becoming great mixologists if we're willing to embrace the chaos, trust the process, and have a little fun along the way.

Listen to the full interview here or watch it!