I love Seattle

Twenty years—how the hell do you capture the ‘moment’ of 20 years in a simple post?

Like every good story starts, “I remember it as if it was yesterday…”

It was around May 2005. I was wrapping up my senior year of college when my roommate, now my co-founder and still my business partner today, said, “I’m not going back to Tri-Cities, Washington.” I tried convincing him with, “We can be a big fish in a small pond,” but he was adamant. He had another year of school left and was already the brain of the operation. Before I even graduated, I hopped into an Infiniti I30 and drove to Downtown Seattle.

My girlfriend at the time (who later became my wife) had just started working in real estate, giving apartment tours to people relocating to Seattle. She printed out a list of eight apartment buildings in the Belltown neighborhood for me to check out. I visited seven of them, frequently calling my family in Tri-Cities, my business partner, and my girlfriend, saying, “There’s nothing in Seattle.” Then, I took a left off Bell Street onto 4th Avenue, and there, on a tree-lined street, I saw Centennial Tower (three-minute load zone). A black concierge named James welcomed me into the building. **James would later become a dear friend. He paid for a meal or two when I was broke, attended my wedding, and was there at many of my business events over the next decade until he passed away last year.

I toured a small 800 sq. ft. penthouse, a third of what was rumored to be Jamie Moyer’s old penthouse when he pitched for the Mariners. The cost: $1,700 a month. I had $12,000 to my name. After first, last, and deposit, I was left with $7,900. I called my parents before signing the lease, and they both said, “$1,700? You’re crazy.” But it felt like home. And it was—for my first two years in Seattle. The views from the 26th floor are still etched in my mind: Elliott Bay to the left, Lake Union to the right, and the Space Needle front and center. So close that during New Year’s celebrations, you could feel the heat from the fireworks—though I never saw them myself. My older brother and business partner did on more than one occasion while I was out of town.

Over the years, that apartment witnessed the birth of our first company, love, countless Sopranos episodes, many parties, new friends, old friends, and endless memories.

Mind you, I had never lived in a city before—only visited many. For the first few weeks, I was so intimidated by the parking garage with its key fob that I’d run down every few hours to feed quarters into the meter or move the car, depending on the zone I was in. Eventually, with James’s help, I moved it into the garage.

One random Friday, I hailed a cab and said, “Take me to the best place in Seattle.” Without hesitation, the driver took me around the block and dropped me off at Flying Fish on 1st and Bell. That’s where I had my first two oysters—nowadays, two dozen go down like chilled shots of vodka. If the apartment was my home, the Flying Fish was my living room. I learned to slurp oysters, drink martinis, and unwind with both familiar and unfamiliar faces almost every night until the restaurant closed five or so years later. The bartenders were Mark and Shane, the proprietor was Christine Keff, and the staff—Thomas, Claire, Guy—were my best friends, whether they knew it or not. I loved Flying Fish so much that when it closed, I even bought the stools. To this day, when I see those familiar faces from over a decade ago, I get teary-eyed, longing for the moments I didn’t realize I was living in, because I was always racing toward the future I knew I’d have—and ultimately did.

Between 2007 and 2012, I moved several times: first to the Cristalla downtown (a building I’d toured and knew I would live in), then to a house for six months in Queen Anne off Lee Street, and eventually to an apartment with my brother on 3rd and Blanchard. When I got engaged, we moved to a loft in Pioneer Square. Each part of the city—mainly Belltown—brought new people, friends, and strangers into my life. Many of those encounters are hazy after a couple of martinis. I loved Seattle! You couldn’t have dragged me away from the city that shaped my 20s and 30s. And yet, here I am, writing this.

The pandemic had a profound effect on me, as it did on many others. Here’s how it changed my life. Our company was growing fast, licensing the hell out of our software worldwide. Then, I got a call from a customer, saying, “I have a huge client for you—100,000 websites…” Our software builds websites at scale. I was in Cartagena, Colombia, at the time and flew home a week early to work on that deal (this was January 2020). By March, we had ironed out the details and sent contracts out for signature. Then, by March 20th, the pandemic had locked down cities. I remember going to Assaggio’s restaurant, my de facto hangout spot after Flying Fish closed in 2010. Several of the staff from neighboring Tom Douglas restaurants came in, crying, saying, “We’ve been let go indefinitely.” I thought, “This is just a snowstorm; it’ll be over by Monday.”

If I told you how sure I was of every day between May 2005 and March 2020, you wouldn’t believe me. I knew exactly what I was doing, why I was doing it, and everything in between. And then, BOOM! The city I loved, the people I loved—everything—stood still. Over the next three years, people moved, disappeared, lost touch, and the culture itself shifted—the world over. No longer was coming into the office necessary. What I once would have flown home for pre-pandemic, I now do on the road, remotely—anywhere. The biggest deals we’ve closed? I’ve done them while lounging in a pool in Arizona.

The question I get most often is, “How’s Seattle?” I have to tell them a lot of what I’ve written here. But there’s more. Unrelated to politics and homelessness, the city itself shifted. No longer are random nights had. No longer are spontaneous moments in office buildings, coffee lines, or lunch queues happening. The city has gone quiet. For three years, I tried to reignite that spark—to open a bar, take over a hotel, create a ‘new’ Flying Fish (even reaching out to the former owner). But nothing happened. Not for lack of trying, but because the pulse of the city was gone. So, every winter, I head to Arizona.

Then, an old spark returned—the same one I’d had since I was 17, the same one that led me to start my own company at 17: New York City. During one of several trips to Manhattan (our company acquired a business in SoHo in 2021, and 40% of our team is now on the East Coast), I started to imagine a life outside of Seattle. If you’d asked me before, I’d have given you 20 reasons why I’d never leave Seattle. But on one of those trips, I told my business partner, “I want to live here.” A few weeks later, I brought my wife, and she fell in love too. Seven months after that, we had our admissions interview for the co-op we’d chosen. Now, we’re in New York City.

I still go back and forth as needed. I still root for Seattle, and our company’s offices are there, along with my wife’s company. But life demanded something different for us. As my wife said in our co-op interview, “New York City is where our next chapter begins.”

So, thank you, Seattle. You taught me everything I need to navigate the Big Apple, and for that, I will love you—forever.

Mark Michael, your fanboy.

Mark Michael and Daniel Rust