Eating Shit, Humility, & The We/I Rule
I’ll be the first to say it. I don’t go around calling myself a “leader.”
But – I have been doing this for over two decades—building teams, launching products, hiring great people.
And after that much time in the game, you do start to develop a kind of pattern recognition.
You see what works, what doesn’t, and what’s truly inspiring.
And sure, a lot of this applies to founders, CEOs, and C-suites —but don’t let titles fool you.
Leadership isn’t exclusive to the corner office or tech bruhs with the most followers.
It shows up in parenting, coaching, teaching, working the register, managing a shift.
Really, it’s just about being a decent human who helps other people thrive.
Eating $15 million of shit
Let’s flashback about ten years ago at The Motley Fool.
We kicked off a massive campaign with a $30 million sales goal – a truly monster swing.
End result: we landed somewhere around $15 million.
Not exactly great – a $15 million miss is…noticeable.
And guess who was leading marketing at the time?
Yup. Yours truly.
And that miss wasn’t just a number on a spreadsheet.
It was the kind of thing that echoed through the halls—especially when you had to explain it in front of the whole company.
Every month, we had an all-hands meeting called the Huddle.
Picture 300 employees – IRL – jammed into a room listening to updates, roadmap reveals, the occasional hype session (and bi-annual bringing into the office of zoo animals).
When marketing crushed it, we’d get up there and take a bow. Boom. 💥
So naturally, after a $15 million miss, I couldn’t just hide in a corner and pray for the sweet release of death.
I had to face it – figure out my story, my angle…
Ultimately, I didn’t sugarcoat it. I built a super tight deck – broke down the whole thing—slide by slide, dug into what we did wrong.
I still remember the gist: we grew the front end of our funnel like mother effers. But then we got temporarily short-sighted — focused too hard on upsells and neglected the middle of the funnel. The part where you build trust, educate people, and get them ready for the big-boy products.
So, we ultimately sabotaged ourselves a bit.
I got up in front of 300 people and walked through every mistake, in full transparency.
Accountability. Analysis. Action. (look at that alliteration, 8th grade English)
Afterward? I got more compliments from that one talk than I’ve ever received for any “win.”
It was shocking, tbh.
Before that day, I had a bit of a reputation—intense, maybe a little sharp around the edges. 😁
Unintentionally, that presentation helped shift how some people saw me – made me more human, more approachable.
Years later—no joke—I’d start a new project and someone would go, “Hey, I remember that mid-funnel presentation from years ago.”
Turns out, eating shit sticks (pun).
Show some damn humility (if you’re great at what you do, it shows)
You don’t need to run around showboating.
In reality, the louder someone screams about how awesome they are, the more it screams insecurity.
The real leaders at your company? They’re getting shit done, making their teams better, and not wasting time angling for credit.
Yeah, every once in a while you’ll have to advocate for yourself—especially if some donkey is taking your work and putting their name on it.
But most of the time, if you’re consistently being uber productive and you’re fun to work with, people notice.
As a CEO, I’ve seen it play out over and over:
The “me me me” folks are a pain in the ass and require more attention and more atta boys and more 1:1s. When they get constructive feedback, they’re more sensitive and more distraught.
The quiet, team-first killers?
They’re the ones who are most interested in the quality of their work, on improving and iterating… they’re the ones I want around me.
Which brings me to one of the best rules I ever learned.
The We/I Rule
Credit to my friend Anand Sanwal of CB Insights, one of the sharpest advisors I’ve ever had.
I was writing a memo to my co-founders—basic stuff: P&L summary, month-end closed books, some roadmap updates. I sent it to Anand to take a look.
He replies: “Have you ever heard of the We/I Rule?”
Here it is:
- Wins? Always frame them as we.
- Mistakes? Always frame them as I.
For example: “We beat our marketing forecast and grew revenue 35% month-over-month.”
Versus: “Expenses came in a bit high—I should’ve anticipated facilitator costs better.”
Tiny change. Massive impact.
I went back and ran my last few memos through ChatGPT using that rule – I was surprised, at least two or three tweaks popped up.
Here’s the takeaway:
When you write like that, you’re sending a crystal-clear message—
I’ve got this. I’m building a team that can win. And I take full responsibility when we don’t.
I know this may seem obvious, and it may seem like a really small thing.
But try it for a week – the next time you write to your team, your boss, or your board.
Run it through the We/I Rule.
See what shows up.
If you liked Chapter 1, don’t forget to check out Chapter 2 and Chapter 3 as well.
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