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Biggest Gift
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
Tiffany Kent
6 days ago2 min read


Power of the Late Launch
Why starting at 48 was my biggest advantage—not my setback. When people learn I launched Wealth Engagement at 48, they always ask the same question: “How did you think about taking the jump?” But that question misses the point. At 48, I wasn't taking a big risk. I was starting with: - 25 years of Wall Street wisdom - A Rolodex built through real relationships - And most importantly, clarity about what actually matters Here’s what nobody tells you about “late” starts: - You de
Tiffany Kent
Nov 212 min read


Life of a Showgirl
The world is constantly giving you feedback. Most of us just don’t slow down long enough to listen. A few weeks ago in Nashville, I put my whole life on hold for Caroline’s audition. And the experience taught me more about lanes, identity, and money than I expected. The Moment Everything Got Quiet The producers kept asking her: “Are you country? Are you pop? What’s your style?” Caroline said the truth — she likes to sing everything and she appreciates all kinds of music. B
Tiffany Kent
Nov 142 min read


The Creative Detour That Led Me Home
Home Coming After months of chasing goals, I had to admit to a friend —I didn’t hit my business target. Not because I wasn’t working, but because I was building my third act. At first, I thought the next chapter was writing another book. But that lesson took a while to set in —I learned I’d need a large social media audience to make it matter. I don’t have that (yet). 2025 Spring break brought reflection. Then trade wars hit in April. My analyst brain kicked back in—position
Tiffany Kent
Oct 313 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 242 min read


What Our Kids Can Teach Us
Driving Caroline to the airport on Saturday morning, I confessed, I sometimes sound/look like my mom or I know I try to control Caroline the way my dad used to try to control me — a family trait I'm trying to let go. She listened closely. I reminded her that, whether we like it or not, we inevitably become our parents in some ways. And I'm trying hard to be self-aware and notice the pattern. What was cool was that she was actually listening instead of tuning me out. Mea
Tiffany Kent
Oct 172 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 102 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 32 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 263 min read
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