What Yale Taught Me (Even Though I Didn’t Go There)
- Tiffany Kent
- May 30
- 2 min read

Not having gone to Yale you might have assumed I wouldn’t have had a great time at my husband’s college reunion.
But instead, I had a fabulous time.
Why? I didn’t have to impress anyone.
No one else wanted to try to impress others either!!
Some were searching for the Second Mountain or what’s next in life.
When we are young, money is our primary driver.
But then Money becomes our Kryptonite.
Money holds us back from taking risk,
pivoting or figuring out which new game to play.
But what got them here won’t get them where they want to go.
Not everyone wants to start over and start at the bottom like Andre Agassi.
But this is where the death and rebirth happens.
In the book Open by Andre Agassi, (My favorite book ever)
Agassi needed to change his game. So Agassi hires Brad Gilbert, who wrote the book Winning Ugly.
What got [Agassi] to the pros doesn’t work in the pros, Brad says.
He’s been stuck at a local maximum his entire pro career.
“Stop thinking about yourself and your own game,” Gilbert told him, “and remember that the guy on the other side of the net has weaknesses.
Attack his weaknesses.”
At the 1994 U.S. Open, for the first time in his pro career, Agassi was unseeded. He reached the final, where he faced Michael Stich, recent Wimbledon Champion and the fourth-ranked player in the world, who had a weakness: his forehand.
Throughout the final, Agassi hits his weakness and wins.
The first unseeded player in 28 years to win the U.S. Open - Thanks to Billy Oppenheimer, who wrote about this in his recent newsletter.
In one small group session at Yale, I shared my own turning point —
Running on a track in hot Houston, at the time,
I was lost and unsure of my net worth.
and somewhere in that uncomfortable place —
the bottom, the blank slate —
It's where the magic happens.
I stopped thinking about myself and the money I used to make and started thinking about who I wanted to serve.
Because it’s about your story. Your why
And how you write or play your next chapter.
If you need help with your next play, please reach out!
Thanks for reading!
Tiffany Kent
Your Friendly Wealth Engagement Guide
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