At surf camp in Portugal. My career on Wall Street was a bit of a random walk. I started in investment banking because it seemed like the best place to learn about companies and finance without going to business school. And honestly, I liked the people. They were cool nerds. After business school, still not totally sure what I wanted to do, I went back to banking at Goldman Sachs because it seemed like the right path. But eventually I realized something about myself: I didn’t

Georgetown. There's a scene in Mad Men where Peggy Olson watches a focus group of women trying on lipstick. There are dozens of shades sitting on the table. Why? Because every woman wants to find her color. I think about that scene a lot when I think about why my business has grown. Big companies need models. They need systems. They need to create models that clients fit into because that's how you scale. But people don't want to be put into boxes. They want to feel understoo

Houston, TX. When Caroline started violin at 3, it was painful. Private lessons were $25 for 30 minutes—which felt like a lot in 2011—and half the time she was rolling around on the carpet instead of listening to her teacher. I wanted to quit. It was embarrassing. It felt like a complete waste of time and money. But something inside me kept saying: I want her to learn how to do hard things. A few years ago, I thought about this while visiting a dorm at UPenn. I couldn't belie

Nantucket After a fun summer of traveling, visiting friends, and working on building my platform, I'm happy to be back home in Atlanta. This photo was taken outside the Handle Bar on Nantucket, which feels oddly appropriate for this time of year with the kids headed back to school and college. Because as we enter the second half of life, do we really have a handle on what we want? For years, one of my dreams was to own a second home on Nantucket. Nantucket—or ACK—holds some o

Rich and I love rewatching Mad Men. On the surface, it's about a Madison Avenue advertising agency in 1960s New York. But underneath, it's about something much deeper. It's about identity. After years of chasing success, Don Draper walks away. At a retreat in California, he admits he's been living under another man's name, breaking his vows, and pretending to be someone he isn't. Peggy Olson begs him to come back to New York and work on the Coca-Cola account. He does eventual

Boston's Freedom Trail I recently attended my 25th Harvard Business School reunion in Boston. Reunions are funny. We arrive carrying our highlight reels. - Promotions. - Successful businesses. - Impressive titles. - Net worth. It's easy to fall into the trap of keeping up with the Joneses. The problem is that keeping up often requires something else: - A facade. - Looking successful. - Sounding successful. Acting like you have everything figured out. Ten years ago, at my 15th

On Wall Street, traders talk about the "pain trade." It's the outcome nobody wants because they're positioned for something else. Ironically, it's often the direction the market eventually goes. Lately, I've been thinking about how the pain trade applies to life. Ten years ago, during my midlife crisis, I found myself confronting something I had spent decades trying to outrun. Carl Jung called it "the shadow." The hidden part of ourselves we don't want to acknowledge. The fea

If you’ve ever ridden a mechanical bull, you quickly learn one thing: the only way to stay on is to counteract the force. When the bull bucks left, you shift right. When it drives forward, you lean back. You don’t fight it by going rigid, and you certainly don’t just hold on and hope for the best. You read it, react, and play offense. Sound familiar? Riding a bull market is no different. When the market dips, the instinct for many is to panic, sell, and brace for impact — ess

Running through Central Park on the west side of Manhattan — the financial capital of the world, and arguably the easiest city on earth to compare yourself to others. Skyscrapers to your left. Young ambition on the right. And there I was, ten years ago, deeply jealous of a more successful friend. But in investing, we compare companies with one another to see if one is cheaper or more expensive. If there is a catalyst to either short the expensive one and/or buy the cheaper st

A student in the Emory financial planning class asked me in front of everyone: "How should I think about my career if I don't come from money?" I looked at her and said: "Your being poor is your superpower." She looked at me like I had two heads. But also backed it up with the famous line from the 1987 movie Wall Street when Michael Douglas (as Gordon Gekko) tells Bud Fox (Charlie Sheen) to avoid hiring Ivy League graduates, "Most of these Harvard M.B.A. types, they don't add

My husband is from San Diego. The movie Almost Famous is one of our family favorites — a throwback to SD in the 70s. The whole film is about a young journalist who gets the band to reveal their true insecurities. That vulnerability? It made them real. And it made the Rolling Stone article unforgettable. I've been living my own version of this the past few days. First, I spoke to Professor Usha Rackliffe, a financial planning class at Emory's Goizueta Business School my th

Beverly Hills High School Graduation 1991 The Best Lessons Came From What Mom Got Wrong A friend once asked me: "Does your mom find your posts offensive?" I told her the truth: My mom isn't on LinkedIn. But even if she was, she knows — I wouldn't be where I am today without learning what NOT to do from her. She was my anti-role model. And here's what I've come to believe: Humans can learn from others' mistakes. Watching someone else fail is a shortcut. You skip the emotional

NYC last summer I remember when I first got engaged. I loved looking at my diamond ring Two carats. Clear. Beautiful. I felt lucky. I had just started my career on Wall Street, riding the subway every morning as my boss did. After getting married, having babies, a nanny, and a wonderful husband, my career took off. But something funny happened one morning on the subway. I looked down at my ring and thought: Maybe I deserve a bigger one. Around me was the wealth of New York—

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

Last year, Kiki and I stood at the top of Tower Three (a Double Black Diamond run at Jackson Hole). The run looked terrifying — steep drops, trees, rocks, no easy way down. We could've taken the groomed trail. The safe route. Instead, we pointed our skis downhill and went. That's how I've come to see most of life's big choices. Ten years ago, I sat down one night and drew something (A Decision Tree) that quietly shifted everything. Just two possible trajectories on a piece o

Patio at Beverly Hills High School (1998) Life Yearbook signing. Harsh? Maybe. But hear me out. I recently read 𝘐'𝘮 𝘎𝘭𝘢𝘥 𝘔𝘺 𝘔𝘰𝘮 𝘋𝘪𝘦𝘥 by Jennette McCurdy — a raw, honest look at trauma, control, and silence behind closed doors. It made me reflect on my own uncomfortable truth. The custody battles. The power struggles. The courts. Unlike Jennette, I fought back — a lot — with my single mom. Where did that independence come from? At a young age, my mom gave me sma

Homecoming ( guys dress up as cheerleaders, cheerleaders dress up as football players.) Not rich in money. Rich in perspective. We lived in a crappy apartment in Beverly Hills. Just so my mom could feel rich. Just so I could go to Beverly Hills 90210 While classmates drove BMWs, I walked to school. At 15, I was balancing my mom's checkbook, watching her fall for "buy now, pay later" scheme. That Circuit City TV? $19 a month for 5 years on a $700 purchase. While I didn’t

(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

In front of Ben Franklin Alexandra recently asked me: “I just don’t know what I need to know about the stock market for my interviews.” My instinct? “I can talk to you about the market!” I was so eager to help—finally a chance to show off decades of experience. She replies, “I already know what an LBO is and what multiples are…” And she does. But that’s not real money education—and she definitely wasn’t asking for a lecture on what drives stock prices. And then it hit me. The

My mom's failure in life was the biggest gift to me. Rich and I were out in California visiting parents—his in San Diego, my mom up north (I also went to the Big Game). Sitting with my mom on Sunday, watching her struggle with disorganized bills all over the place, I realized something: We don't want to end up like our parents. Harsh? Maybe. But here's what I mean. At 15, I was balancing my mom's checkbook. Learning indirectly, how compound interest worked, quietly observin