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Hi Playmakers!
At 17, I cold emailed a billionaire and asked him to pay for my college.
He said yes.
That one message changed everything — and taught me something I’ve carried with me ever since:
A cold email isn’t just an ask. It’s a door.
Since then, I’ve used cold emails to land jobs in Silicon Valley, get featured on Good Morning America, book A-list speakers, and launch partnerships with celebrities. I didn’t have connections or credentials — just a “Why not me?” attitude and a willingness to hit send.
Here are the top tips I’ve developed for how to write cold emails that actually work:
Always try to find the person’s direct email. If it’s an investor, you can often guess it based on the firm. If it’s a celebrity, IMDb usually lists a rep. And many billionaires? Shockingly simple Gmail addresses.
Use the subject line to clearly state your ask. I usually start with “Request for” followed by the topic.
Keep it short: two paragraphs max. One is even better. Yes, really.
Be specific and actionable. End with a proposed time to connect. A presumptive close (not if, but when) works like magic.
Never attach anything. Put everything in the body. Most people read emails on their phones — and won’t bother with a deck.
Bonus: If you have a referral, put it in the subject line (“Referred by Jenny Stojkovic”). If it’s real, it works 9 out of 10 times. If it’s not, don’t do it — you’ll blow your shot.
I grew up in a tiny Canadian farm town. Cold emails helped me leap into rooms I was never supposed to be in.
Because the biggest difference between those who make it and those who don’t?
One of them hit send.
That’s why I’m sharing some of my best tips and tricks with you. I’ll be sharing more in future emails.
Forward this email to a friend who needs to see it.
And, as always, drop me a line and tell me what you think!
Jenny
The Play of the Week: Fidji Simo, CEO of Instacart
Fidji’s leap from a French fishing town to Silicon Valley helped her become one of the most powerful women in tech.
Before she led Instacart’s $10 billion IPO and joined OpenAI’s leadership team, Fidji Simo was a girl in southern France, dreaming of a life far beyond the docks her father worked on. Today, she’s the CEO of Instacart, the incoming CEO of Applications at OpenAI, and the founder of a groundbreaking women’s health institute changing how chronic illness is treated.
Her story isn’t one of privilege or shortcuts.
Fidji was born in Sète, a coastal town where few imagined a future in global business. The daughter of a fisherman and a seamstress, she was the first in her family to graduate from high school. She simply asked: “Why not me?”
The Execution Plan: Your Play for the Week
Insights are only valuable if they’re acted on. Let’s turn this knowledge into impact with small but powerful action steps.
This week’s challenge: shoot your shot!
It’s time to take the leap! Send that email detailing why you deserve a promotion. Reach out to someone that seems out of reach asking for a job opportunity. Ask that potentially special someone out on a date. Life’s big wins won’t simply happen to you. You have to get out there and create the opportunity. This is your sign to take action!
Call to Action:
1️⃣ Reach out to one person you’ve been putting off and shoot your shot.
2️⃣ Report back and let me know how it went! Drop a comment or share your post below. The best responses may be featured next week.
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Playmaker’s Spotlight: Real People, Real Wins
Taylor Lorenz dropping the real facts over here as this week’s Playmaker of the Week. As a former East Coaster who lives on the West Coast, it never ceases to amaze me how different the working style is. Have you noticed this, too?
What team are you on: laid-back West Coast or high-energy East Coast?
One thing that sucks about NYC is that it’s a very 9 to 5 city. LA you can make plans with a friend to hang on 2pm on a Tuesday and no one blinks. Here it’s like, everyone is at work during the day
— #Taylor Lorenz (#@TaylorLorenz)
1:40 PM • May 19, 2025
Want to be featured next?
Make sure to tag @Jenny Stojkovic on your post for a chance to be featured.
The Extra Edge: Industry & Success Trends
🔌 Nuclear power is the future, and Germany is starting to get with the program.
☮️ Believe it or not, violent crime is falling rapidly across America.
🏥 Blue Shield of California appoints their first female CEO. Check it out.
👶 A baby is healed with the world’s first personalized gene-editing treatment. It’s an incredible story.
On this day in 1881, Clara Barton founded which nonprofit?
How to Get Involved:
The Wednesday Play isn’t just a newsletter — it’s a community. I’ll be announcing much more in coming weeks and months! For now, let’s connect across social.
