Welcome to another fun-filled edition of the Revenue Diaries. As before, I will give you a TL;DR because we’ve GOT A LOT to discuss. Here’s what you can expect in this entry:

• Personal: Fighting Back Against the Voice in Your Head

• Personal: Vuori Hitting Peak Dad and Still Loving It

• Growth: Building an AI Version of Myself (And How You Can Too)

• Podcast: Learning to Thrive in Chaos with Natalie Marcotullio

Enjoy!

On Fighting Back Against the Voice in Your Head

I thought it worth sharing the last few sentences of this entry at the very beginning because it’s worth multiple mentions: This isn’t about fixing yourself. You’re not broken. It’s just another way to move through the world with a little less weight on your shoulders.

I know you’ve got a lot on your plate. Maybe it’s work pressure, maybe it’s something in your personal life that won’t let up. We all deal with it. Are you just feeling stuck? No matter what you do, it’s never quite enough. I get it. And I don’t have all the answers, but I have something that might help.

And to be clear, it’s not a magic fix, but it’s a tool that can help you power through moments of anxiety and self-doubt. It’s called the Shadow Tool. And yes, as an annoying marketer, I tried to come up with another name, but to no avail. Sorry.

The idea comes from our friends, Phil Stutz and Barry Michels, authors of The Tools. They are also behind using your deathbed as a driver and practicing gratitude, as we’ve discussed in our last couple of entries over the past month.

It’s simple: we all have a Shadow. It’s the part of us we try to hide, the version of ourselves that makes us cringe, that we’d instead not acknowledge. And we all know ignoring it doesn’t make it go away. It just sits there, running the show in the background. The Shadow Tool helps bring it into the light so you can work with it instead of against it.

I’ve spent many, many hours reading and re-reading the book and dealing with my Shadow. So, I thought it would help if I pulled out five SHADOW DEMONS I deal with and how I’ve incorporated the tool into my daily routine using three parts: The Challenge, Scenario, and Application.

Hopefully, it helps!

1. Leadership & Decision-Making

The Challenge: You’re in a board meeting, and a major decision is on the table. The pressure is intense, and you feel the weight of responsibility. Doubt creeps in.. what if you misread the situation? What if your judgment isn’t as sharp as you think?

Scenario: As discussion swirls around the table, you start replaying a past leadership mistake in your mind. A voice in your head whispers, "What if you get this wrong, too?" Your Shadow makes you hesitate, urging you to defer, delay, or play it safe.

Application: Acknowledge your Shadow instead of resisting it. Say, “I see you, but I’m in charge now.” The presence of doubt doesn’t mean you lack ability; it means you care. Take a breath, trust yourself, and make the call.

2. Sharing Content & Public Speaking

The Challenge: You’ve written something or prepared a talk, but fear sets in before you share it. What if people don’t like it? What if they don’t get it?

Scenario: You’re about to post on LinkedIn or step onto a stage, and suddenly, you think about past times you felt ignored or dismissed. Your Shadow makes you second-guess yourself.

Application: Accept the fear, bring it along, and share your voice anyway.

3. Social Anxiety & Sobriety

The Challenge: You’re in a social situation where drinking used to be your crutch. Without it, you feel exposed, like you don’t know how to navigate the room. Your anxiety is heightened, the discomfort is real, and the old impulse to grab a drink resurfaces.

Scenario: You’re at an event, standing in a circle of people with drinks in their hands. There is a lull in the conversation, and you start feeling self-conscious. You remember how alcohol was used to smooth these moments over. Your Shadow whispers, “This would be easier if you had a drink.”

Application: Acknowledge the urge instead of fighting it. Say, “I see you, but we’re doing this sober.” Let the discomfort be there without letting it decide for you. Confidence comes from stepping through that moment, not numbing it.

4. Parenting (With Your Kids)

The Challenge: You lose patience with your child, and the guilt sets in. You wonder if you’re doing enough, if you’re being enough.

Scenario: Your child is having a meltdown, and despite your best efforts, you snap. Later, you feel like a failure, hearing the voice of your Shadow telling you, "You’re not a good parent."

Application: See your younger self, acknowledge their needs, and give your child what you once needed.

5. Parenting (With Your Own Parents)

The Challenge: A conversation with your parents pulls you back into old patterns. You feel like a kid again… unheard, seeking approval, or frustrated.

Scenario: You visit your parents for the holidays, and they make a comment that instantly makes you defensive. Your Shadow feels like the misunderstood teenager again.

Application: Recognize your younger self and respond as the person you are now, not the child you once were.

The point of all this? We spend so much time running from the parts of ourselves we don’t like. But they don’t go away. They just get louder. The Shadow Tool is about turning toward them, recognizing them, and saying, “I see you. LFG.”

This isn’t about fixing yourself. You’re not broken. It’s just another way to move through the world with a little less weight on your shoulders.

♥️ kyle

I’m pleased to announce Share Your Genius as our first partner for the newsletter and podcast. I’ve known the team and their CEO for years. They are simply the best creative agency, helping brands build deeper relationships with their audience through binge-worthy podcasts and great content.

On Vuori Hitting Peak Dad. Now What?

I wear Vuori a lot, and I like it. It’s comfortable, fits well, and doesn’t make me look like I’m trying too hard. But at some point, I started noticing something: Vuori isn’t as cool as it used to be.

Maybe it was when I saw my dad wearing it. Maybe it was when I realized half the guys at my local coffee shop were in the same joggers. Maybe it was when the guy in front of me at Whole Foods, wearing a complete Vuori set, drove off in a Rivian with a “Live Laugh Lake” bumper sticker.

I don’t say this as an insult. Vuori makes excellent clothes. But when a brand reaches full suburban dad saturation, it raises a question: what’s next?

The Rise and Plateau of Vuori

Vuori came up as the alternative to Lululemon. You remember. We wanted a brand for guys who didn’t want to be caught in leggings but still wanted premium athleisure. It had that low-key, West Coast vibe: “I could go to the gym, but I also might just have a matcha and take a meeting from my deck.” It was aspirational, but in a relaxed way.

And now? Vuori has made it. It’s in Nordstrom. It’s in every airport. It’s probably what your boss wears when he’s trying to be “off-duty.” That’s great for business, but bad for exclusivity. And I’m a marketer, I value exclusivity. 

So, Is It Time for a New Brand?

I don’t know. Part of me feels like I should be looking for the next Vuori before Vuori turns into the next Lululemon. But part of me also doesn’t care. The clothes are still good. The shorts still fit.

So instead of searching for the next big thing, I’m doubling down. I’m embracing Vuori like their shirts softly embrace me. And if I’m going to do that, I might as well acknowledge what the brand has become and have some fun with it.

I asked our friend, ChatGPT, to come up with an ad campaign based on how Vuori is perceived. Here’s what it came up with:

📍 Scene: A guy in his early 40s steps out of his Tesla, adjusts his Vuori joggers, and stretches like he’s about to run, but instead walks into a café for a cold brew.

📍 Cut to him sitting in an all-white home office, leading a Zoom call. He’s wearing the Vuori Ponto Hoodie. Someone on the call asks if he’s been working out. He hasn’t, but he nods.

📍 Later, he gets a text from his buddy: “Pickleball?”

📍 Slow-motion montage of suburban dads playing pickleball. Sweating just enough. One guy fist-bumps another. Life is good.

📍 Voiceover: “Vuori. For the man who still says ‘bro’… but only at a reasonable volume.”

Hilarious and accurate. 

And yeah, maybe Vuori isn’t as cool as it used to be. But it’s still good. It still fits right. It still feels like a hug from a fabric engineer who understands my needs. And until something better comes along, I’ll keep wearing it.

On Building an AI Version of Me (and How You Can Too)

Vuori aside, let’s get back to the SHADOW version of yourself, it’s time to wax poetic about creating multiple versions of yourself. 

Let’s start here. Have you ever imagined an AI version of yourself? One that generates insights helps you strategize, or pushes creative challenges? 

That’s exactly what Jordan Crawford set out to do: train an AI to think like me. 

I've been following Jordan’s work for a while, and he's my go-to source for everything AI. This past week, I was fortunate to help facilitate a genAI discussion at Chili Piper’s Chilipalooza in Arizona. Let me tell you, the experience was electrifying. One revelation, in particular, blew me away: Jordan built an AI version of me that mirrors my thought process and style so closely it feels almost human.

Frighteningly human. 

So, let’s break it down. How did Jordan do it? If you’re curious about replicating this process for yourself, your team, or even your favorite industry expert, I’ve got you covered.

And if you'd like to see the finished product with prompts and inputs, please click here.

Step 1: Defining the AI Model’s Purpose

The first step in Jordan’s experiment was clarifying why he was doing this. His goals were to:

• Extract my marketing expertise and replicate my strategic thinking.

• Train AI to respond as I would, based on my past work.

• Put the AI version of me to the test by challenging it to build a brand campaign faster than I could.

If you’re considering building an AI model of yourself (or someone else), the first question to ask is: What problem am I trying to solve? Whether automating content creation, learning from an expert, or just having fun, defining the purpose upfront is key.

Step 2: Collecting Data on Me

To make the AI as accurate as possible, Jordan gathered as much publicly available content on me as he could, including:

• Podcast appearances

• Published articles & books

• Social media posts

• Marketing campaign case studies

• Speaking engagements

If you’re building an AI model, the input data's quality determines the output's quality. The more examples you provide, the more likely the AI is to replicate the subject’s tone, thought process, and expertise.

Step 3: Crafting a Deep Research Prompt

Jordan knew the AI needed to think like me, so he designed a detailed research prompt. It focused on:

• My core marketing philosophies

• My problem-solving approach

• How I develop brand strategies

• My unique approach to marketing

If you’re building an AI version of yourself, think of it as creating a playbook for how you feel and operate. The goal is to give the AI a structured way to analyze and replicate your expertise.

Step 4: Choosing the Right AI Model

To process all this information, Jordan used Claude 3.5 Sonnet and OpenAI’s 01 Pro. These tools allowed him to feed large amounts of content into the AI, helping it understand and mimic my thinking.

If you’re experimenting with AI, here are some tools to consider:

• Claude or OpenAI models for text-based responses.

• MidJourney or Runway AI for visual representations.

• Custom-trained AI agents for brand-specific knowledge.

Step 5: Testing AI’s Output

Once the AI model was trained, Jordan put it to the test:

1. He had AI generate brand strategies in my style.

2. He created a challenge where AI-generated content was compared to my work.

3. He even experimented with creating a Cyborg Kyle using AI-generated imagery (because why not?).

If you’re building an AI version of yourself, test it against your work. See where it gets things right and falls short, then refine it accordingly.

Here… You Try.

Want to create an AI version of yourself, your CMO, or a thought leader in your space? Here’s a simplified roadmap:

1. Define the goal – What do you want AI to do?

2. Gather content – Collect articles, podcasts, and social media posts.

3. Build a research prompt – Outline the expert’s thinking patterns.

4. Choose an AI model – Select the right text, voice, or image generation tool.

5. Test & refine – Compare AI’s responses to real-world examples and tweak as needed.

AI isn’t here to replace human creativity, but it can be a powerful tool for scaling expertise and generating new ideas. Whether you’re a marketer, sales leader, or entrepreneur, experimenting with AI personas might change how you work. Nay, it will.

On Learning to Thrive in Chaos with Natalie Marcotullio

Most marketing leaders know the feeling—wearing a dozen different hats, context switching between strategic planning and execution, all while trying to protect your sanity. Natalie Marcotullio, Head of Growth and Operations at Navattic, gets it.

We sat down for an episode of The Revenue Diaries to talk about everything except work (at least in the traditional sense). Natalie shared lessons from growing up with a father who thrived in high-stakes corporate environments and a mother who mastered the art of empathy as a kindergarten teacher. She also walked me through how she manages burnout, keeps team members from sprinting into exhaustion, and the one non-negotiable in her daily routine—working out.

A few gems from our conversation:

💡 Managing a high-growth role without burning out: Natalie lives by her calendar. She schedules time for deep work, workouts, and breaks—ensuring she’s at her best for her team.

💡 Lessons from family: Watching her dad lead with kindness and balance stress without bringing it home shaped how she manages her own team today. Meanwhile, her mom’s ability to really understand people has made Natalie a better marketer.

💡 The startup mentality: If something breaks (like a laptop in her college side hustle), figure it out. If no one hands you a playbook, write one. Adaptability beats perfection.

💡 New York vs. Florence: She loves the constant energy of NYC but equally appreciates the slow, intentional approach to life in Italy. Balancing both is key.

We also got into her accidental path into running track, what it’s like growing up with ultra-athletic parents, and why startup marketing isn’t for everyone.

If you’re an early-stage marketing leader (or thinking about becoming one), Natalie’s advice is simple: Be honest with yourself about what you want. Startups are rewarding, but they’re also ambiguous, unpredictable, and sometimes lonely. If that excites you, lean in. If not, that’s okay too.

Listen to the full conversation here or your favorite place for podcasts.