Kevin O’Leary of Shark Tank fame tells a fascinating story of his mother’s passing and the drama that ensued. After her husband died tragically at a relatively young age, Georgette O’Leary raised her son Kevin as a single mom and working professional. She was not wealthy, but she was a woman of taste, who sounds like the original gangster when it comes to building an investment wardrobe. Each year, she purchased exactly two Chanel suits. She would save up for six months to buy the first and then another six months to buy the second. After doing this for decades, she had quietly accumulated a one-of-a-kind couture time capsule by the time of her death. With Kevin named as the executor of his mother’s estate, he was left as the unfortunate mediator between the women in the family vying to become the lucky heiress of Georgette’s priceless Chanel collection (and, no doubt, the envy of all her friends and acquaintances).
This story has stayed with me for some time, possibly because I too dream of building such a wardrobe over time, but also because it, and stories like it, seem to strike a note in my mind. It reminds me of the time Ivanka Trump wore her mother’s gown to an event, channeling Ivana’s distinct style. Regardless of anyone’s political thoughts, there is something unique about wearing a gown owned by an ancestor. Not only because it is rare to have something so well-made it can last decades and still be wearable, but also because the things we own today are so disposable to us.
And this chord is broader than clothing. A similarly potent emotion arises when I pull out my great grandmother’s 120-year-old china set. The set itself isn’t worth any significant amount of money. Regardless, I have found there is innate value in knowing four generations of women in my family have served their family meals on it, carefully washed it by hand, and cringed as their children chipped it against the hard countertop, just as I have done. They are the dishes I reach for when hosting our Thanksgiving dinner, not because they are the most beautiful, but because they serve as a rare, almost spiritual reminder of women long since gone whose hands touched these same plates.
I am aware not everyone is lucky enough to have a grandmother with a closet stuffed full of vintage Chanel (a category to which I begrudgingly belong), but in an age where we have access to almost everything created, there is something beautiful about limiting our possessions to the things we truly love, things which may endure longer than we do. While subscriptions let us listen to more music than we can possibly get to in a lifetime, there is beauty found in a father’s favorite CD collection, a collection built over decades and composed of songs you grew up dancing to in the living room. Or the hardback edition of Pride & Prejudice where you first fell in love with Mr. Darcy and dog-eared page 186 after going back countless times to read your favorite quote.
As someone who is not generally sentimental over things, it is a unique position to be writing about possessions having inherent value beyond their market price. Perhaps my daughter’s unexpected question about whether or not she will get to wear my clothes when she gets older has planted a tender seed in the hostile ground of my economics-degree-and-spreadsheet-loving heart. No matter the cause, it has me considering what my physical legacy can and should be.
Do I think I’m going to start buying a Chanel suit every six months? Hard pass on the pink tweed. And I have no desire to leave behind a house full of things which feel more like a burden than a blessing. I think of my sweet grandmother, who kept forty-eight pink glass goblets tucked carefully in her curio, twelve for each of her children to take when they married. No one took them. No one wanted them. They sat, untouched and dusty, for forty years before being sold off at an estate sale. However, we all kept a canvas or two of the oil paintings she labored over but never felt were "quite good enough" to hang.
So if not Chanel, what are the heirlooms I can give my children over the next few decades? What are the things I will build, use, and love; things I would be proud to pass down?
A few weeks ago, I was speaking with a marketing firm, and they asked if my ultimate goal was to scale Martindale and sell it to private equity. I recoiled. Partly because private equity has a way of stripping the soul out of the things it touches, but mostly because I carry a quieter vision, one I’ve almost been afraid to acknowledge. It sits silently in the corner of my mind, and I fear if I say its name, it will vanish into vapor.
A vision of building something that endures. Something my children might one day choose to step into. A legacy they could see me in long after I’m gone. Something I poured myself into, cried over, spoke about with love, and slowly, thoughtfully, shared with them over time.
I’m also aware that a parent’s dream can easily become a child’s burden. I won’t force my children to love design or fashion. But I can show them what I love. I can invite them into it.
And in building something with care, I can give it a kind of value that goes far beyond a price tag or a revenue multiplier, something shaped by memory, by effort, by meaning. Something that, if I’ve done it well, might endure long after I do.
Until next time,
Elise
