Hi Playmakers,

My old boss Ron Conway once said something that completely changed my investment thesis. After auditing 500+ companies he'd invested in, he found that 77% failed during the dot-com bubble. The survivors? They weren't the ones who got there first. They were the ones who watched the first movers burn through cash, make costly mistakes, and then came in with a better strategy. Google wasn't first. PayPal wasn't first. But they won.

Ron was the founder I worked for early in my career, and this lesson shaped everything I look for as a VC today.

Here's the thing about being first: you pay for every mistake with real money and real time. You're basically paying to educate the market on what doesn't work.

Then someone comes along, watches you struggle, learns from your expensive lessons, and builds something better.

Friendster had 3 million users before Facebook existed. MySpace was worth $12 billion at its peak. But both got cluttered and slow. Facebook watched, learned, and kept things clean.

Google wasn't the first search engine — Yahoo, AltaVista, and Ask Jeeves were. The iPhone wasn't the first smartphone — BlackBerry and Palm were. But Google and Apple learned from their predecessors' mistakes and built something radically better.

Being first means you're the crash test dummy.

And here's where it gets interesting for women founders.

Women entrepreneurs almost never get to be first movers. They get told "no" by investors. They get dismissed in boardrooms. They watch men with similar ideas get funded while they're bootstrapping.

But that disadvantage? It's actually an advantage.

Whitney Wolfe Herd wasn't first to dating apps, but she watched Tinder create toxic dynamics and built Bumble where women make the first move. Today, Bumble is worth billions.

Sara Blakely wasn't first to shapewear, but she watched competitors make uncomfortable products and built Spanx — something women actually wanted to wear. She became the youngest self-made female billionaire.

These women didn't just build great companies. They built smarter companies.

When you're underestimated and underfunded, you can't afford to make the same mistakes the first movers made. You have to watch, learn, and execute flawlessly.

Which is exactly what I talk about in my new keynote.

This March, I'm taking my viral series Women Founder Wednesday — which has generated 40 million impressions — off the platform and onto company stages for Women's History Month.

My new keynote "Women Who Built The Impossible" gives your team what billion-dollar founders know: how to build visibility, turn barriers into competitive advantages, and convert ambition into measurable success.

50 minutes. Virtual or in-person. Stories customized to your industry. Get a feel for my keynotes here.

Here's what I need from you:

If you work somewhere that books speakers — or you know someone who does — I have very limited March availability. March dates are filling fast.

Reply to this email if you’re interested.

Because here's the truth: being underestimated isn't a disadvantage. It's the ultimate competitive advantage. You just have to know how to use it.

Jenny

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Born in Cairo, Egypt and raised in Texas as an immigrant, Dina Powell McCormick rose through the White House and Wall Street.

She went on to become the first woman to ever serve as President of Meta.

Meet Dina Powell McCormick.

Stop waiting for permission to be first.

This week's challenge: Find one area where you've been waiting for the "right time" or the "perfect moment" to make a move. Then ask yourself—what can I learn from the people who already tried and failed?

Maybe it's launching that side project. Asking for the promotion. Pitching your idea. Whatever it is, stop waiting for permission to be first. Instead, be smarter.

Watch. Learn. Then build something better.

Danica Simic (aka @codingmermaid.ai) is one of my favorite follows on Instagram. She’s a master at breaking down every single detail that you need to know to thrive in AI.

Check out this latest post on how to get yourself up to speed on AI for 2026.

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