Why Vera Wang Fired Her Boss at 40 (And Your Million Dollar Lesson in Her Pivot)

I’ve had a great week. Three different potential corporate partners - major brands - expressed interest in working with me - sponsoring this newsletter, engaging me for media, etc.

Why not you too?

I’m telling you this not to impress you, but to impress upon you that you should have corporate partners and fat corporate contracts too! I am openeing up 3 spots in my one-on-one corporate contracts coaching program right now. 6 weeks, hands on, you and me, and the end result? Getting you a juicy, fun, life-changing deal with a big corporation. If you’re interested, email me at [email protected] with the subject “Coaching” and let’s chat!

Your big "failure" is often just a sign that you just might be playing the wrong game.

I’ve always been fascinated by people who bloom late. We live in a culture that worships the 22-year-old tech founder, but the real wisdom, the hard-won-lessons, comes after you’ve taken a few punches.

Vera Wang is the patron saint of that second act.

Opening Curtain

By 1987, Vera was a powerhouse, but she was a powerhouse on someone else’s payroll. She had been a world-class figure skater who narrowly missed the Olympic team. She spent 15 years as a senior editor at Vogue. She was the ultimate insider.

But then, she hit the wall.

Vera was passed over for the Editor-in-Chief position (the job famously went to Anna Wintour). After fifteen years of giving her best ideas to a corporate masthead, she was out. She took a job at Ralph Lauren, but the fire-in-the-belly was gone.

Vera was a 40-year-old "expert" who felt like she had nowhere left to climb.

Breakthrough!

Her breakthrough happened because of a personal headache. Vera was getting married and went looking for a dress. What she found was depressing. The bridal industry in the late 80s was a sea of “meringue” dresses: Poofy, frilly, and stuck in a 1950s time warp. There was zero sophistication.

Vera realized that while she had "failed" to get the top job at Vogue, she had walked away with something far more valuable: An Editor’s Eye.

Her “failure” had perfectly set her up for her breakthough (funny how that works!)

Vera realized that modern women wanted to look like themselves, not like a cake topper. She saw a gap in the bridal market where authority and style were completely missing.

Vera’s Big Bet

At age 40, with no experience in retail or manufacturing, having never been an entrepreneur before, Vera decided to stop being a worker bee and to instead become the Queen.

When Vera opened the doors of her first boutique - inside the famous Carlyle Hotel on Madison Ave - she wasn't just launching a store, she was launching a rebellion against the "meringue" and the "poof" of 1980s bridal fashion.

The shop was tiny, but the stakes were massive.

Vera had used her father’s money to secure the most prestigious real estate in New York, betting that if she positioned herself as an elite editor rather than a common retailer, the market would follow her lead.

While the experts said she was too niche, Vera leaned into the exclusivity of the Carlyle, and her Vogue background, and her editor’s eye, and curated a selection that looked more like a high-end gallery than a wedding shop.

Shortly after the first few socialites walked through the door, the word had gotten out: Vera Wang hadn't just opened a boutique, she had redefined the category of the modern bride.

The Big Payoff

Today, Vera Wang is a multi-billion dollar global brand.

(And for us, Vera didn't just change weddings; she proved that your history, even the parts that felt like a dead end, can be the raw material for your empire.)

Here is what my most recent Corporate Contract Coaching client (one of your fellow Notes readers!) had to say about our work together:

“Like many small business owners, getting to the next stage requires making decisions and learning go of obstacles.

Steve Strauss is a talented coach. With an eye toward reaching our goals, he guided me through a small detail, big picture process envisioning my future business. I trusted his advice - it made sense.

Steve knows business and understands what motivates people. Looking back, I’m amazed at how my perceived obstacles vanished- I was having such a good time creating my future. I highly recommend working with Steve.  —-Joanne Miller

I am openeing up 3 spots in my one-on-one Corporate Contracts Coaching program right now. 6 weeks, hands on, you and me, and the end result? Getting you a juicy, fun, life-changing deal with a big corporation. If you’re interested, email me at [email protected] with the subject “Coaching” and let’s chat!

The Takeaway

If you feel stuck, it’s not because you lack talent. It’s possibly because you are still trying to win a game that was designed for someone else (you entrepreneur you!) Sometimes, often even, the million-dollar breakthrough happens when you stop auditioning for the "experts" and start owning your unique selling point.

What can you do that no one else can?

Do that.

Steal This Strategy

🛠️ Tool — Business Model Canvas Use the official Strategyzer template to map out your pivot. Vera Wang didn't just change her job; she changed her business model from "Employee" to "Owner."

📖 Read — Late-Life Career Transitions A Forbes breakdown on why starting a venture later in life—like Vera did—is often a power move fueled by "accumulated human capital."

🛠️ Tool – The Burts Branding Blueprint™
This week’s free guide for Notes readers. Build a real brand without busting the budget.

📖 Book — The Small Business Bible My definitive guide for building a business that thrives. See Chapter 1 for how to launch a business that makes a difference.

About Steve

Steve Strauss is the best-selling author of The Small Business Bible (and 17 other books), Inc.’s small business columnist, a lawyer (non-practicing), and an entrepreneur. He sold his last venture, TheSelfEmployed.com to Mark Cuban & Zen Business. Need a ghostwriter or a newsletter for your business? Contact Steve!