Let me just start with the ending: I got the job.
2009. At The Motley Fool. The company that I was quite literally obsessed with.
At 25 years old, it felt like the only place I was meant to work. I had an offer in-hand from The World Bank—something that once felt prestigious—but I knew deep down that I’d dread it.
For me, it had quickly become The Motley Fool or bust.
The Cold Email That Sparked It All
So how did I get the interview in the first place?
This story involves a bad stock pick, a rogue deck, and about 20 guessed email addresses.
At the time, I was in grad school and had a stock pitch project due for my investing class. I was also aggressively trying to land a job at the Fool.
I had already gone the traditional route: submitted my resume through their website, wrote a thoughtful cover letter, checked for alumni connections. Crickets.
I remember thinking: f*ck me, I can’t even get them to reach out & reject me.
In hindsight, it’s not surprising. Great companies get buried in applications. And even if you’re qualified, your resume is just one of hundreds in a massive digital pile.
But there was no chance I was giving up.
Life Gave Me a Stock Tip…
One day I clicked on a Motley Fool ad and promptly entered my email. Got the report or whatever it was that i was fishing for, and moved on.
And then the next day, I got one of their marketing emails pitching a stock to buy—National Oilwell Varco (NYSE: NOV).
The email was signed, “Kate Ward, Publisher.”
That’s when I had an idea.
Instead of just agreeing with their stock pick—or worse, ignoring it—I decided to do my class project on why NOV was actually a bad investment.
And I’d pitch a different stock instead – I threw in some charts, wrote a half-witty analysis.
It was part snark, part financial thesis, part “please notice me.”
Hacking the Ole’ Inbox
I built the slide deck. Now I just needed someone to send it to.
So I went looking for Kate.
The problem was, obviously I didn’t have her email address.
So I guessed.
I sat there one afternoon typing out 15–20 versions of what I thought her email could be: :
- kate.ward@fool.com
- kward@fool.com
- ward.kate@fool.com
- katew@fool.com
- etc.
Some probably bounced. But one of them worked.
I never heard from her directly—but someone must’ve opened it.
Because a week or two later, I got an email from Kara Chambers, who worked in HR at the Fool and would later become a colleague for decades.
She said their hiring manager would be reviewing my application. (!!!)
I was pumped – but not content to let it sit.
The Follow-Up Blitz
I followed up. And followed up again.
I sent Kara a thank-you.
Then another follow-up telling her I was “insanely interested” in the position.
Then another message with more context I “forgot to include.”
Was it too much? Probably. Was it borderline stalker vibes? Mos def.
But the truth was, I didn’t just want “a” job – I wanted that job.
And when you want something that badly, you don’t wait politely in the lobby, hoping someone stumbles on your shitty resume or decides to call you up out of the blue.
You knock. Then you knock again. Then you wedge your foot in the door before it closes.
Eventually, I got the interview.
And eventually, I got hired (I actually got rejected from the first role I wanted – and didn’t leave them alone until I got the next one).
What Actually Got Me Hired?
The truth is, I was definitely a bit underqualified at the time.
I didn’t have years of investing experience. I didn’t spend time as an analyst or as an editor at another financial publication.
I didn’t know anyone at the company, and my resume was fine, but def not winning awards.
But I stood out. Not just with a gimmick, but with a reversal of expectations.
They pitched me a stock. I challenged their thesis and gave them something else.
And I did it in a way that felt aligned with their brand—irreverent, curious, a little bold.
It was a risk. They could’ve thought I was obnoxious or condescending. But they didn’t.
They saw someone who understood the game, had conviction, and wasn’t afraid to do something different.
That project ended up being the thing that got me in the door—not my GPA or LinkedIn profile.
The Power of Showing, Not Telling
Too many job applications are just noise:
“I’m analytical.”
“I’m a self-starter.”
“I’m passionate.”
Cool story bruh.
Show me. Make something. Write something. Analyze something. Build something.
Show me how your brain works.
Especially if you’re trying to break into a competitive company, or shift industries, or punch above your experience level—you need to close that gap with creativity and productivity and clarity.
It’s never been easier to apply. Which means it’s never been harder to stand out.
The shortcut isn’t sending a million cover letters—it’s doing some actual work.
Summing It Up
I worked at The Motley Fool for over a decade.
I grew into roles I never imagined I’d hold. I met some of the smartest people I’ve ever worked with. It changed the trajectory of my career, and my life.
But I’m not sure any of it would’ve happened if I hadn’t opened that marketing email, taken the risk, and sent a cold pitch into the void.
The stock I pitched? Who knows if it did well. The exact wording of my email? Long gone.
What mattered was I didn’t wait and I didn’t ask for permission.
If you’re trying to break in—especially to a dream job—don’t wait for a formal invite.
Do something unusual, but smart.
Make the first move. Show how you think. Go around the default systems.
People remember creativity and courage.
And if all else fails… guess 20 email addresses and throw a hail mary.
P.S. If you want a good laugh, you can check out my original deck here. Don’t be a hater when you check out Slide 3— the aggressively bad stock photo choice. I was young. I didn’t know any better.
