The Heart & The Sword
I paced my dorm room practicing what I’d tell her. I tried to remove “likes” and “ums” from my lexicon. I wanted to sound knowledgable but nice, funny but curious. And most of all, I wanted the job. All of my previous jobs required me to take a shower once I returned home. I had to remove the paint from my hair when I was hired to paint the inside of buildings at the University of Bridgeport. I had to scrub off the dried ice cream that would line my forearms after my shift at Ben & Jerry’s. And my shower water would turn into a cascade of coffee as the grinds from my shift at Coffee Tree were washed away. This would be my first real job. In an office. With a desk. And I wanted it, badly.
MoneyHunt was a show on public television, and was a precursor to business shows like Shark Tank and The Profit. Hosted by Miles Spencer, an former investment banker, and Cliff Ennico, a corporate lawyer, they, along with a leader in business, would review business plans of up and coming businesses (mostly dot com start-ups … this was the late 90s). The show’s offices and the studio where they shot it we’re conveniently located a 20-minute drive from my parents’ house, and it would be the perfect summer job for a college kid with an interest in television. And so, I got on the phone with someone named Blair who interviewed me, was happy to see that I was a recommendation from a former MoneyHunt employee, Chris Tar, and offered me the job over the phone.
A few weeks later, and I was walking through the front door of the MoneyHunt offices, dressed, I’m sure, in khakis and a button down shirt - an outfit which would be quickly replaced by a T-shirt and shorts. I met Blair and the small staff I’d be working with, got settled at my desk, and then heard him. From somewhere up above me. A voice, not booming or threatening, but one that commanded attention.
“Longest commute ever,” came the voice.
Carrying a brick-sized laptop under one arm, and a dog leash in the other, Miles appeared at the top of a spiral staircase that lead down to the main office. (Note: The MoneyHunt offices were located in a former cardiologist’s office which was attached to Miles’s house - hence, the line about his commute.)
He descended the stairs, held out his hand at an angle and just said, “Miles Spencer.”
Then he handed me the dog leash and the little Rottweiler puppy attached to it. “This is Scrappy, he’s yours for the summer.”
A few weeks before my first day at MoneyHunt, Miles’s Rottweiler, Netscape (see comment above about it being the late 90s), had a litter of puppies. Everyone on staff was given a puppy to mind during working hours. The runt of the litter, and the one with a malformed hind leg, was named “Scrappy” and the little guy was attached to the leash Miles handed me - effectively turning Scrappy into my charge for the summer. Incidentally, an adorable Rottweiler puppy with a busted leg is the perfect way to meet girls, especially when you walk him through the stores and boutiques along Main Street in Westport. I do, however, still owe an apology to J.Crew for the massive dump Scrappy took on their floor one afternoon.
Not only did I learn a lot about television production that summer, but I learned a lot about business and culture from Miles. We’d play pétanque on work breaks, eat Provence-inspired lunches prepared by Miles in his kitchen, and I’d pick up on the ins and outs of not only investing in companies, but how to run them, too.
This summer job turned into a several year job, and expanded into creating a charity event called "Kayak for a Cause” that gathered hundreds of people together to kayak across Long Island Sound for charity. MoneyHunt only ended because the dot com bubble burst and sent everyone scrambling to figure out their next moves. Miles started a venture capital firm and brought me in as a creative consultant, and we parted amicably once I graduated, moved to New York, and took a job at the Late Show with David Letterman.
But even when I wasn’t working for Miles, he’d ask me to look at companies he was thinking about investing in, helping to raise funds for, or those that needed more creative strategy. Conversely, I’d send him drafts of business proposals I was working on, share ideas on emerging technologies, and talk about life on long walks through Greenwich. At some point, we shifted from the boss/worker dynamic to a friendship. So much so, that when I found myself in Saint-Jean-Cap-Ferrat with my daughter who was recovering from injuries sustained in an accident in Italy, he called to not only make sure she was recovering well, but offered up some of his favorite places and resources in the south of France to make sure our time there was both healing and fun. (A watercolor he painted of Cros Dei Pin, a favorite beach of my daughter’s in SJCF, was waiting for us when we got home and is currently hanging in our living room.)
At some point—maybe during one of those walks through Greenwich, maybe on a pétanque court, or maybe over a bottle of Infini rosé—we stopped talking about business and started talking about building one together.
But it wasn’t immediate. As I’ve mentioned before, we weren’t chasing the next unicorn or whiteboarding growth hacks over oat milk cortados. We were both busy with our lives, our families, and the projects that paid the bills. Still, the idea of building something—something meaningful—kept surfacing. In conversations. In texts. In a tennis match-like series of blog posts. We didn’t know what the thing was yet. We just knew we wanted it to matter.
What finally did it, what finally tipped us over the edge, was a shared ache. A shared realization, really: that the people we love don’t stay forever. And the memories we have of them… fade faster than we’d like to admit.
We’d both lost people. We’d both felt the sting of remembering too late the questions we should’ve asked. The stories we forgot to record. The voices we wished we could hear one more time—not just in memory, but in conversation.
And so, we started asking:
What if they didn’t have to be gone?
What if we could create a way to hold onto presence—not just photos, not just dusty videos, but something more alive?
That was the spark that became Reflekta.
We didn’t have a playbook. We had a set of values and a shared gut feeling. And thankfully, two very different—but wildly complementary—ways of working.
Miles, in true form, became the sword.
He slices through ambiguity like it owes him money. He’s clear-eyed, ruthlessly pragmatic, and has a built-in BS detector that goes off if someone even thinks about fluffing a deck. When things get messy or political or bogged down in a sea of options, Miles draws the line. He’ll fight for what’s best for the company with a kind of honor that reminds me of a character from an old Kurosawa film—if that samurai also had a beach volleyball habit and a Michelin-starred restaurant obsession.
Me? I’m the heart.
I try to make sure we build this thing with care. That we don’t forget the humans behind the avatars, the families behind the stories, the daughter who just wants to hear her grandmother’s laugh again. I think about how it all feels—how Reflekta lands emotionally, how we communicate, and how we lead. If Miles is out there on the battlefield protecting the company’s future, I’m in the trenches with the team, making sure everyone still feels seen, heard, and valued.
We joke a lot about who the brains are—and I’m pretty sure it’s neither of us. It’s our team. The wild, brilliant minds behind the scenes building the tech, refining the interactions, and giving soul to software. They’re the ones who took our “wouldn’t it be amazing if…” conversations and turned them into something real. As a quick side note, one of the members on our team, and the guy who introduced me to Miles originally, is a brilliant guy named Chris Tar. I’ve known Chris, literally, since the day I was born. He lived in my neighborhood, and his brother Jason was one of my best friends growing up. I’m sure another essay could be written about that 45+ year relationship, too.
People often ask how Miles and I make it work—this whole “friendship into partnership” thing. The truth is, we’ve been training for it for 25 years without knowing it. From my first day at MoneyHunt holding the leash of a wobbly-legged Rottweiler puppy, to fundraising for kayak charities, to debates about the future of memory and AI—we’ve always known how to push each other, how to trust each other, and how to step out of the way when the other is in their element.
That watercolor in my living room of a beach in Saint-Jean-Cap-Ferrat? It’s where my daughter and I spent quiet, healing days after her accident. The painting arrived without fanfare. Just a little piece of thoughtfulness and beauty from a friend who knew what it would mean.
That’s what Reflekta is to me.
Not just a company.
Not just a product.
But a living extension of that kind of grace.
The sword and the heart.
And a team full of brains.
Trying to build something that helps people hold on a little longer… and remember a little deeper.
We’re still at the beginning of this 25 year endeavor, but I like where it’s headed.
