If you want to go fast, go alone. If you want to go far, go together.
Hi Friends!
Co-pilot edition #13. Lucky thirteen.
July in Portland is the payoff month. The rain finally clocks out, the berries show up at every farm stand, and the whole city acts like it just got let out of school.
This month has a theme running through it, and I didn't plan it that way. It just kept showing up. In my training rides. In a TV show I can't stop thinking about. In a decision I made about how I'm building this company.
Let's jump in.
- Jess
What I’m Practicing
Not going it alone.
Last June, a friend and I signed up for a 50 mile bike race together. We trained separately but agreed to ride together on race day.
Within the first ten miles, she got a flat tire. I didn't know how to change it. Neither did she. (Lesson learned.)
Then it started to rain. Hard.
She waved me on: "Go without me. I'll get help and catch up." We never rode side by side again.
I finished that race alone, soaked, and eventually without GPS after my phone died. (another lesson learned.) It was brutal. We both crossed the finish line, but we could only laugh about it once our cold, stiff bodies thawed out in the commons afterward.
This August 9th, that same friend and I are riding again. (Cuz I aint going out like that) This time it's a full century. 100 miles. For those of you who know the Enneagram, are you surprised I’m an 8 Challenger? 😆
So this time, we're doing it differently.
We've trained together. She's stronger on the long, steep inclines. I'm faster on flats and recover quicker. No matter what the ride brings us, we've agreed to a no drop policy. We stay together, period.
Could I ride 100 miles alone? Probably. But life is better with someone beside you. Someone to hold you accountable, cheer you on, and keep you honest when you want to quit at mile 70. Which is about when you want to call it.
I'm applying the same principle to Co-pilot. This summer, I’m kicking off my first official Advisory Board for the business 🙌🏼. These are leaders who have built and sold agencies, driven revenue at a global scale, and navigated M&A, from scrappy small companies to multinationals. People who have been down this road before, know me, and can help me scale faster, move with intention and make smarter moves than I ever could on my own. I’m still so honored they said yes.
Two years into building this company, I could keep white-knuckling it solo. Instead, I strategically chose world class training partners.
Again and again, I read versions of “leaders have coaches” or “no one is self-made.” Why would I be any different?
And here's what I know from my work with executives: the same is true for building your brand. You can absolutely figure it out alone. Plenty of people do. But with someone in your corner who knows your voice, steeps themselves in your industry, and shows up every week to push and refine and hold the standard, you build the muscle faster. And you actually stay in it.
So that on race day, whether that's the podcast interview, the board update, or the earnings announcement, you're not winging it. You've been training. Together. And it shows.
August 9th. Wish me luck. 🤞🏼🚴🏻♀️
What I’m Loving
Better Call Saul.
I just finished it. I know, I know. The series wrapped four years ago. I never claimed to be an avid Netflix and chill kind of girl, so I’m late to the game. But, oh boy. I loved this series more than almost any show I've watched to date. Only shy of Handmaid’s Tale and Mad Men.
For all of us who watched Breaking Bad, we knew how Better Call Saul ended before it started. Jimmy McGill becomes Saul Goodman and comes to defend his client, Walter White, the chemistry teacher turned drug dealer. The whole world knows. And I still couldn't look away for six seasons. So good.
By season three, I began paying attention to the credits. Who was behind these two insanely good shows? Vince Gilligan and Peter Gould. They understood something most storytellers (and most brands) never figure out. And here it is in three succinct bullets:
Transformation is the story. Breaking Bad was famously pitched as turning an overqualified high school teacher into Scarface. Saul runs the same play in a sadder key: a charismatic con artist turned attorney who genuinely wants to be good, but loses the fight with his own nature one small compromise at a time. Even Kim, Saul’s wife, begins a slow but insidious decline from a by-the-book, values-driven corporate attorney to eventually end up a Florida suburban wallflower with date nights at Outback to simply avoid ever remembering her past wrongs.
Patience is a flex. These shows moved slowly. Long wordless stretches. Entire episodes about one court case. They trusted the audience to do the work, and the audience repaid that trust with fierce loyalty. In fact, the shows weren’t really about drugs and Mexican cartels at all. They were about the subtle building of characters, over time, who let you figure it out.
Nothing is wasted. A choice in season one (which you’ve long forgotten about) detonates in season five. Actions have trade offs and no character is without multiple flaws. And at the same time, you are rooting for it to work out. Every word in those scripts was toiled over. You feel it.
Now here's why this belongs in a newsletter about executive brands.
Your professional brand is a character arc, told in public, over years. The leaders people trust most are the ones whose story compounds. Where the post from 2024 still squares with the podcast interview in 2026. Where patience and consistency beat volume. Where specificity in a story beats complex corporate vocabulary.
One more thing. Gilligan spent seven years writing on The X-Files before he got to build his own universe. Then he spent fifteen years building it. The long game is the whole game.
Binge accordingly. ⭐️⭐️⭐️⭐️⭐️
Shining a Light
This month I'm shining a light on The Path Forward, the new vodcast from my friends at UiPath. Five episodes are out now, and they're tackling the question every business leader is chewing on: How do you turn AI momentum into something that actually creates real, meaningful change inside your company and with your customers?
My favorite episode features Zack Kass, Global AI Advisor and former Head of Go-to-Market at OpenAI, alongside Michael Atalla, CMO at UiPath. They take the wide view: is AI just another technology cycle, or the beginning of a deeper shift in how people work, lead, and drive value? And as AI gets more capable, what becomes more important about being human?
A few moments worth highlighting:
On what we should really be worried about, from Zack:
"The biggest misconception is that we keep asking, are we going to be poor, instead of are we going to be happy?"
On who wins the next five years, also Zack (and I didn’t pay to have him say this):
"Storytelling continues to win out. As differentiation collapses, you really will start to have more brand preference."
And a practical challenge from Michael that I've already started using:
"Ask AI to do something you don’t think it can do, as opposed to asking it to do the thing you’re watching every day.”
That last one is homework, by the way.
🎧 Watch my favorite episode here: https://youtu.be/jzKtJ76qKPw
ICYMI
The front door of the internet is moving.
My smarter than I could ever write it read this month is Shiv Singh's piece, "The Front Door Moves."
For twenty-five years, digital marketing ran on a simple pattern: people searched, links appeared, brands fought for the click. That contract is breaking. When someone asks ChatGPT, Gemini, Claude, or Google AI Mode what to buy or whom to trust, the brand no longer gets the first word. The model does. Shiv was quoted in The New York Times calling the shift "like an earthquake nobody expected."
I heard another person on a call just this morning say “Chat GPT AKA Old Google”
AI visibility is becoming the new search visibility. Brands used to compete for clicks. Now they compete to be recommended.
And this is already personal. Here's a snapshot of things I asked Claude this past month that I would have Googled a year ago:
Here’s your homework this month: Ask the models about yourself and your company. You might be surprised what the new front door already believes.
📖 Read the full article here.
I also recommend reading my friend Debra Aho Williamson’s Substack, where she’s written extensively on how AI is shifting how we search, found here.
Who’s with Jess? 🐾🐾
First, June's winner: Jen Whelan correctly identified last month's photo from Scottsdale, Arizona. Slightly unfair advantage given she was IN the photo. 😄 Congrats, Jen!
Now for a plot twist. This month we're pivoting from "Where's Jess?" to "Who's with Jess?"
Meet the newest member of the Jensen family: a 3-year-old black lab rescue with big paws and zero respect for my cream carpet. All my hopes of keeping it clean are officially out the window.
Can you guess his name? Hint: he's named after a good guy from Star Wars.
Reply with your answer. First correct guess gets a shoutout in the August edition.
Thank you for being here. See you in August. 💛
— Jess
Bet on yourself.
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