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Big Magic
As we head into spring break, I had a small breakthrough. Yesterday I presented to the Harvard Business School Women’s Association. They reached out after I posted an article about my career pivot and the lessons I learned along the way. The title of the talk: From Net-Worth to Self-Worth: What Markets Taught Me About Identity, Loss, and Personal Alpha. I told the truth about the dips and valleys in my life and career. I talked about not avoiding pain — because if you lean in

Tiffany Kent
Feb 272 min read


A Secret I Told Men
New Canaan, CT Men's Club What I Told Men in New Canaan About Their Wives and Money While everyone knows there are two certainties in life: death and taxes. There's a third topic most couples hate discussing even more. Money. Tuesday, I spoke to my dad's men's club (after my snowy run in Old Greenwich) —a room full of retired guys who've spent decades building portfolios. The topic? How to talk to your partner about the stock market and money. I started with a question: Wha

Tiffany Kent
Feb 132 min read


Bringing home the Bacon
early mornin' bacon experience A $2 savings on bacon taught me more about wealth than most finance books. Tuesday morning, I was unpacking my Walmart grocery delivery. Bacon. The microwave-ready kind. $7.98 delivered to my door. At Publix? Same bacon is $10. They pay premium rent. Premium operating costs. Premium prices. But here's what stopped me mid-unpack: The driver who brought my groceries earns maybe $10-15/hr with tips. No leverage. Paid by the hour. Trading time for

Tiffany Kent
Feb 62 min read


Houston, We Have a Problem
My husband told me to go f .. figure it out. I was in Houston. Three young kids. Money in the bank. And I was paralyzed with anxiety about whether I would have enough. On paper, I had nothing to worry about. But in my head, I was back in my childhood crappy Beverly Hills apartment, watching my mom do nothing about her financial future. Next week I'm speaking to my dad's men's club in New Canaan. (Just got postponed due to weather to Feb 10th! ) Topic: How to talk to your wif

Tiffany Kent
Jan 222 min read


Greetings and Happy New Year!
What I’d Tell My 23-Year-Old Self About Money — and Climbing Mountains Greetings from Zermatt. The last time I stood here, I was in college. Same mountains. Same views. Completely different lens. Back then, I thought success was about earning altitude fast. Wall Street. Long hours. Steep climbs. No looking down. What I didn’t understand yet: Work isn’t just about earning — it’s about training for the next ascent. Here’s what the mountain (and money) taught me over 30 years: ⸻

Tiffany Kent
Dec 31, 20252 min read


What Nobody Tells You About Being a Trailing Spouse on Wall Street
(Photo: Henry noticed where my attention was and took one of my 6 CFP books I was reading to pass my Certified Financial Planning exam. ;-) Greenwich → Houston → Atlanta. Each move for Rich's career meant starting over. New city, new schools, zero network. But the real kicker came when Morgan Stanley held Rich's stock plan. As a "courtesy," they assigned us a financial advisor. When Rich kept dodging the guy's calls, he finally said, "Just talk to my wife." I was between ca

Tiffany Kent
Dec 12, 20252 min read


Key to a Happy Family
Caroline at 6 years old On Sat., Feb. 8th, 2014, I gave up my weekend morning to attend a parent education seminar at my daughter’s school — which, honestly, was the last thing I wanted to do with my time. But I went because I was desperately searching for what was missing in my life. The topic was “organizational health” — not for companies, but for families. Married with three kids, living in Houston, my husband’s career was taking off, but I felt stuck. I didn’t believe i

Tiffany Kent
Oct 24, 20252 min read


Good Friends Ask Great Questions
boat to Martha's Vineyard (2019) Six years ago — summer of 2019 — we were having dinner with close friends from Houston on Martha’s...

Tiffany Kent
Oct 10, 20252 min read


Money Is the Matrix. Modeling Is the Way Out
photo is me trying to look tough with my mouse like Trinity from The Matrix Working at my desk, building a financial model, I slipped...

Tiffany Kent
Oct 3, 20252 min read


Skin in the Game
Fearless Girl When I worked at a hedge fund, pitching investment ideas to my boss was an adrenaline rush. I’d research a company, prepare...

Tiffany Kent
Sep 26, 20253 min read


Hedging Against Craziness
Lately, it feels like chaos is everywhere. Trade cases. Court appeals. Volatile markets. Wacky job reports. High inflation. High interest...

Tiffany Kent
Sep 5, 20252 min read


Wall Street Has a Storytelling Problem
Standing next to the Bull on Wall Street, I couldn’t help but think: Every bubble looks different in the moment—but the story is always...

Tiffany Kent
Aug 29, 20253 min read


Building in the Blue Ocean
Block Island Five years ago, I started my own firm—and recently reached a big milestone: becoming SEC-registered. That moment made me...

Tiffany Kent
Aug 22, 20252 min read


Games people play
Forgot to take a photo at MJ, so took one after my daily run Should every day be just a game? Over the last few years, I became an early...

Tiffany Kent
Jul 18, 20252 min read


How to Do Hard Things
(Like parallel park between two Porsches—one worth $700,000) I used to think my childhood struggles were unique. But as I’ve gotten...

Tiffany Kent
Jul 11, 20252 min read


What Yale Taught Me (Even Though I Didn’t Go There)
The original bulldog, ( Handsome Dan XIX) Not having gone to Yale you might have assumed I wouldn’t have had a great time at my husband’s...

Tiffany Kent
May 30, 20252 min read


He's just not that into you
When I was young and single at Harvard, I had a simple rule: if I didn’t sense he was into me, I’d move on. He’s just not that into you....

Tiffany Kent
May 23, 20253 min read


Which game are you playing?
Everyone talks about the rat race. (or the Buckhead Bubble) Escaping it or buying into it? If the system or game we are playing is to...

Tiffany Kent
May 16, 20252 min read


Hustle Culture
On a recent trip to visit Nashville, it was the first time my daughter and I took a trip just the two of us. Caroline loved Vanderbilt...

Tiffany Kent
Mar 28, 20252 min read


How I became ready to make a difference
I love March. Spring is coming, and the weather is getting a little warmer. I grow to miss the cold winter days of my runs because I...

Tiffany Kent
Mar 21, 20254 min read
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