What Vera Wang, the 50-Something Hustle, and My Birthday This Week Have in Common

At some point, birthdays shift from excitement to existential audit. You start thinking less about cake and more about time—how much has passed, how much is left, and whether you’re making the right bets with it.

This year, I’ve been thinking about age. Experience. And what numbers actually light a fire under us.

I’m not the only one.

Vera Wang is 74 and just inked a deal with WHP Global that will take her brand into its next act. Meanwhile, the WSJ ran a piece about investors betting on entrepreneurs in their 50s and 60s—because, statistically, they’re more likely to succeed than their younger counterparts.

The takeaway? We’ve been thinking about careers all wrong.

Let’s break this down.

Vera Wang’s WHP Deal: The Art of the Late-Stage Power Move

Vera Wang didn’t become Vera Wang™ until she was 40. Before that, she was an Olympic-level figure skater who didn’t make the cut, a Vogue editor who didn’t get the top job, and a designer looking for her next move.

Then, she built a bridal empire. But here’s what matters: she didn’t stop there.

At 74, she just partnered with WHP Global—the private equity-backed firm that owns Toys ‘R’ Us, Anne Klein, and Joseph Abboud. Their model? They don’t buy dying brands. They buy legacy brands and supercharge them.

For Wang, this isn’t just another deal. It’s a masterclass in playing the long game.

Why? Because she understands something most founders don’t:
🚀 Owning a brand beats owning a business.
🚀 Licensing and partnerships scale bigger and faster than one-off product lines.
🚀 Reinvention has no age limit.

The woman built a name in bridal, then pivoted into home, fragrance, and mass retail with Kohl’s. Now, she’s setting herself up to go global, at scale, into beauty and beyond.

Meanwhile, a lot of founders my age are still burning themselves out trying to get their DTC businesses to cash flow positive.

The difference? She’s thinking in decades.

The Myth of “Peaking Early”

The WSJ article hit hard because it confirmed what a lot of us already suspect:

📌 The most successful startup founders aren’t fresh-faced 23-year-olds.
📌 The average successful founder? 45 years old.
📌 Founders over 50 are twice as likely to build a high-growth company.

Yet, everything around us glorifies youth. Silicon Valley worships the 25-year-old genius. Corporate America nudges you out past 50. Social media would have you believe that if you haven’t “made it” by 35, you’re doomed.

Total nonsense.

The most valuable asset you have in business? Pattern recognition.
And you don’t get that at 25. You get it from decades of seeing cycles, market shifts, and human behavior repeat itself.

That’s why older entrepreneurs are the real cheat code.

Here’s what you have at 50 that you didn’t at 25:
✅ You’ve seen trends come and go. You know what’s a fad vs. what’s a real opportunity.
✅ You know how to execute. No more fumbling around. You know what works.
✅ You have a network that actually moves the needle. Not just LinkedIn connections—real people who can cut through the noise and get things done.

The most dangerous thing you can do in your career? Tie your ambition to your age.

The game isn’t over at 40, 50, or 60. For most of us, that’s when it’s just getting interesting.

What This Means for the Rest of Us

I’ll be honest: This week, I did the thing where you look at your own life and wonder if you’re behind. If you should have done more, done it sooner, taken different risks.

And then I looked at Vera Wang.

74 and making bigger deals than ever.

I looked at the data.

50-something founders thriving.

And I realized: It’s not about age. It’s about trajectory.

Some people peak early. Some people peak later. The key is never letting yourself think you’ve peaked at all.

Bet on the long game. Build something with staying power. Play like Vera.