Revenue Diaries Entry 9

We’ve read to our kids almost every night since they were born. The best part isn’t reading I Broke My Butt for the 50th time (though it’s a classic in its own right). It’s the small conversations we have afterward, right before they fall asleep.

Last night’s conversation began with questions about our upcoming trip to Florida to see family.

“How long will the drive take? Does the hotel have an indoor pool? What about our cat and dog? Are they going to be home alone? Can I bring my Halloween candy?” 

But then, he paused. 

“Will my cousins be there?” 

When I said yes, I watched his gaze drift up to the ceiling as if he were pulling memories from a hidden archive. I could literally see the memories flooding in. 

He smiled and said, “I really like my cousins. I can’t wait to see them.” He closed his eyes, still smiling, and drifted off to sleep.

And just like that, my memory archive was immediately unlocked. I had the same reaction in the 1990s when talking with my parents about our summer trips to Washington to visit my cousins. It was the highlight of my young years. 

It reminded me of how powerful memory recall can be and how wild it is to watch your kids experience the same feeling you did at the same age. I couldn’t help but marvel at the possibility of this same kid having the same experience with his child years from now. 

That led to thinking about the memories we’re creating for our kids and how those might someday shape their future.

As we wrap up this year, I’m holding onto the importance of these moments. What we do today becomes the stories we carry into tomorrow and beyond. I hope this season gives you plenty of memories worth recalling.

❤️ Kyle

On Six Months with No Alcohol

Deep down, in the back of my head, I knew I’d been drinking too much. I wasn’t out of control, but there were moments when I’d think I didn’t need that drink. Or, I shouldn’t drink so much around the kids. But I brushed it off like most of us because it felt normal. Drinking was part of my routine and how I relaxed or connected with people. And as long as everything felt manageable, I didn’t give it much thought.

But now that I haven’t touched alcohol in six months, I know it wasn’t even close to manageable. 

It all came to a head on July 25th when I returned home from Jellyfish’s mid-year Revenue Kickoff and got incredibly sick. I was bedridden for two days, coughing nonstop, running a 102-degree fever, and completely wiped out. My body had just given up on me. I’d been traveling a lot that summer and that last trip was the final straw.

I didn’t drink while I was sick (obviously). Who cracks open a Two-Hearted Ale while coughing up a lung? But something clicked. That week, I realized it was the longest I’d gone without a drink in years. And that felt heavy. Who doesn’t love cracking open a beer at the end of a long day? Or meeting with friends to watch the game or sharing a drink to unwind after work?

Half the reason I drank was for the social side of it. But if I’m being honest, the other half was about how it made me feel. Drinking was a social lubricant for me. I liked to have fun, but having fun while carrying this thin slice of social anxiety meant drinking made everything feel easier.

But the truth was starting to creep in. I felt like I was moving in slow motion through my days. I felt like sh*t. And once I stopped, I realized: It’s not worth it.

There is plenty of content out there on the benefits of stopping, and I’ll tick off the list of benefits I’ve received since stopping the juice: 

• Better Sleep: It’s proven that alcohol disrupts deep sleep cycles. Without it, I wake up feeling genuinely rested.

• More Energy: My body isn’t burning extra fuel processing alcohol, so I feel more energized throughout the day.

• Leaner Body: Those Two-Hearteds weren’t doing my waistline any favors. I was maintaining my weight by working out 6 to 7 days a week, but since I stopped drinking, I’ve dropped 15 pounds and leaned out. As my favorite OrangeTheory coach, Maggie, likes to say, 'I’m faster, stronger, and harder to kill.

But the most impactful benefit? Mental clarity and the energy to write and think creatively daily. My morning routine—5-6 am workout, 6-7:30 am writing or working—has completely transformed. It's easier, more productive, and enjoyable without the weird fog of a Two-Hearted lingering in my brain.

Typing these words right now, I’m struck by a realization: most of this content wouldn’t exist if I had kept drinking. That’s the kind of shift you can’t measure, but it’s monumental.

On Controlling Nagging Doubt

Episode 2 of the Revenue Diaries is officially here. I had the pleasure of sitting down with Jeff Perkins, fellow CMO and bald aficionado and talking about everything other than work. 

We laughed, we debated razors, and we even brainstormed a podcast for bald guys (working title: Bald Guyz).

But the real highlight? Jeff’s take on dealing with “head trash,” the nagging doubts and challenges that pile up when leading a team or navigating a tough season. In the video snippet below, he shares how optimism, a killer team, and a “this is temporary” mindset kept him grounded through turbulent times.

Other knowledge bombs you will get from this episode: 

Springsteen’s Secret Sauce

Jeff is a diehard Bruce Springsteen fan who has attended 34 concerts. He explains why Bruce’s ability to connect deeply with his audience inspires him personally and professionally. Jeff’s marathon playlists feature Born to Run and Badlands to keep him moving.

Running as the Ultimate Reset Button

Running isn’t just exercise for Jeff—it’s therapy. After several missed chances to run the NYC Marathon in his twenties, he finally crossed the finish line years later. Now, he swears by the mental clarity, stress relief, and resilience he gets from hitting the pavement.

Leadership Through Optimism
Jeff shares how he navigated leading ParkMobile during a turbulent time. His secret? Optimism, a killer team, and the mindset that tough times are always temporary. (And yes, he talks about the head trash we all deal with—and how not to let it sink you.)

Good Isn’t Good Enough
Whether building ad campaigns or preparing for board meetings, Jeff is a big believer in not settling. His motto? Push back, iterate, and refine until the work is great. Though painful, you’ll hear why this approach makes all the difference.

Fitness as a Leadership Hack
Jeff credits daily exercise with making him a better leader. Whether running, crushing it on his Peloton, or taking group classes like Orange Theory, fitness gives him energy, focus, and balance in a chaotic world.

If you’re into running, leadership, or just better-managing life, you'll love this episode. Listen here. 

On Part 3 of the $750M Content Marketing Framework

Last week, we dove into the first part of the CREATE framework: Crafting the Story. It’s all about defining your narrative, starting with your audience and focusing on their outcomes. Whether you tell how your product helps teams ship faster or give tips on managing a highly productive team, the goal is clarity and connection.

Let’s review the CREATE framework again:

This framework helps you and your team approach content creation with purpose, from defining the story to measuring its impact. By following CREATE, you can build campaigns that align with business goals and engage your audience effectively.

Here’s where we left off. The building of two types of stories: relational and operational with sub-stories under each one. Here’s the example from last week:

Before we get into the R (researching with customers) part of the CREATE Framework, it’s important to take crafting the story one step further: theming the stories. And what’s great, is genAI tools like chatgpt are perfect for this phase of the project.

Take one of the sub-stories. For the sake of the example I’m going t povercoming internal resistance..

Now, the next step—and the first within Research with Customers—is building out each sub-theme. It’s time to tell the stories within the story!

And here’s the key. We want to involve our customers for two reasons. 

1. They are the end consumers. They’ll relate if the story fits their experience.

2. We want their involvement in the final content. Making our customers the heroes of the story inspires them to promote it.

Key point: When I use "customers" here, I mean customers and prospects. Involving prospects in content production has dual benefits: You gather valuable insights while supporting their growth. It's a win-win!

Validation of the Themes

To validate relational and operational themes, identify at least ten customers or prospects for interviews. Here’s how to approach it:

1. Identity Customers & Prospects

   1. Select 10+ individuals across industries and company sizes for diverse perspectives.

   2. Prioritize those with existing relationships for better engagement.

2. Prepare a Stories Guide

   1. Develop a discussion guide with open-ended questions tailored to relational and operational aspects.

   2. Allow room for participants to surface unanticipated insights.

3. Conduct the Interviews

   1. Use video calls or in-person meetings for depth, keeping sessions under 45 minutes.

   2. Record (with consent) and transcribe interviews for analysis.

4. Organize Takeaways 

   1. Categorize feedback into relational and operational buckets. Note which themes resonate most and why.

5. Use Data to Craft Stories

   1. Use GenAI tools like ChatGPT to synthesize data into digestible narratives.

Let’s look at the Stories Guide. What questions should we ask during the interviews? Here are some I’ve used in past iterations of this framework. They are designed to explore experiences, priorities, and pain points, and relational and operational themes align with their day-to-day experiences.

General Context

1. What’s the most rewarding and challenging part of your role as a (persona)?

2. When you think about leading your team, what keeps you up at night?

Relational Themes

3. How do you manage team dynamics, especially when there’s resistance to new ideas or initiatives?

4. What are your biggest challenges when balancing your leadership role with personal priorities or work-life balance?

5. Can you share an example of how you’ve built alignment across teams or departments?

Operational Themes

6. How do you measure success for initiatives like (operational theme 1) or (operational theme 2)?

7. What operational challenges slow down your team’s ability to execute marketing strategies?

8. How do you prioritize using technology or tools to streamline your marketing operations?

Theme Validation

9. Do these themes—relational (human aspects of leadership) and operational (execution and measurement)—resonate with your experience as a (persona)?

10. Are there specific areas under these themes that feel particularly relevant or missing?

Storytelling

11. If we were to tell a story about overcoming one of these challenges, what would make it compelling to you?

12. Who in your network or organization would you recommend should also hear this story?

Now that you’ve gathered a mountain of data and insights, it’s time to transform all that information into meaningful narratives for each sub-theme. This is where tools like ChatGPT (or Claude) can become your secret weapon.

If you’re not leveraging genAI tools to review data and create consumable formats, you’re leaving a ton of value on the table. These tools make the task of summarizing and organizing your themes not only faster but smarter.

Here’s the exact prompt I’d use to generate concise, 3-5 sentence descriptions of the relational and operational themes we mapped out during Crafting the Story:

I’ve uploaded a series of Gong calls featuring customer interviews focused on operational and relational stories from their jobs. Please review the transcripts and identify the most compelling stories based on the following criteria:

1. Situations where customers overcame a significant challenge

2. Unique or surprising outcomes they achieved with our product.

3. Relatable or emotional moments that showcase their professional struggles or wins.

4. Stories that highlight measurable results or transformation (e.g., increased efficiency, saved time, improved collaboration).

Once you identify the best stories, summarize them in 3–5 sentences. Keep the tone conversational and direct, and include enough detail to make the story feel authentic and relatable. If additional context is needed to make the story stand out, suggest clarifying questions I can ask the customer in a follow-up.

With this prompt, you’ll have AI help you break down the raw data into bite-sized narratives that resonate. For example: 

Becky, the VP of Marketing at a high-growth SaaS company, knew her bold new campaign—positioning their software as "the ultimate team accelerator"—would ruffle feathers internally. During the pitch to the leadership team, the VP of Sales pushed back, fearing it might misalign their pipeline messaging. Instead of digging in, Becky leaned on customer data she’d gathered, showing how real users described their success stories similarly. She invited Sales to co-develop enablement materials, framing it as a shared win. The collaboration diffused resistance and strengthened alignment, and the campaign launched to rave reviews. Six months later, both teams celebrated a 20% increase in conversions.

Organize all the stories into a consumable format and prepare them for use in the next part of the CREATE Framework: Execute. 

Stories start with clarity and connection but thrive when shared and co-created. As we work through the CREATE framework, remember that storytelling isn’t just about narratives—it’s about making customers the heroes and reflecting on their experiences. When we amplify their voices, we amplify our impact. Let’s work on the next set of stories that drive results.