I Married a Serial Entrepreneur

I could practically hear the banjo music as I crept up the dirt road toward the pasture. My objective: snap some pictures of cows and scram before Leatherface chased me down with a chainsaw. It was dusk, and I was alone in rural Oregon getting eyeballed by a herd of dairy cows. Let me be clear; trespassing was not my idea; this was my husband’s plan. “Get closer!” he hollered. Easy for him to say from inside the safety of our minivan.

Not many wives would commit a misdemeanor for their husbands, but this was just another Saturday night for me. Trespassing wasn’t the strangest request my husband had made in 37 years, hell; it wasn’t the strangest request he’d made that week! You see, my husband, Mark, enjoys a certain amount of risk, he likes the adrenaline rush. Please understand, he’s not rock climbing free solo or wingsuiting over the fjords. It’s worse! He’s a serial entrepreneur, someone who enjoys the creative process of assembling the right puzzle pieces and launching a business.

My mother begged me to marry a dentist (she wanted the free dental work) or a plumber, (again, she just wanted free labor). “They make good money, and they’re never out of work,” she said, adding. “It’s just as easy to fall in love with a rich man as a poor one.” My mother’s aspirations aside, I had something completely different in mind. I didn’t want to choose a mate based on a career, lifestyle, or bank account. I wanted to fall in love. True love. And I got it — so be careful what you wish for.

I met my husband, Mark, in 1983, at the University of Oregon. It’s a funny story. He saw me crossing campus, remembered me from high school, and looked me up in the campus directory (before everyone had cell phones and privacy was an issue). He called and invited me out for a cup of coffee. On our first date, I asked him “why me?” Maybe I was fishing for a compliment; what I got was anything but. He said he called because I looked like I “needed a friend.” Wow! Talk about ego-deflating.

I’ll skip ahead, we fell in love and got married. I knew Mark well enough at that point to understand what a life with him might entail. When you fall in love with a man who rejects all typical career paths, choosing instead to forge his own way in the world, you’d best prepare for a bumpy ride. And you’d better pull up your big girl pants and embrace the chaos.

Inherently there’s a lot of risk involved in starting one’s own business. We’ve enjoyed some wealth during our 37 years together, and we’ve landed ass-first in some hideous debt. The entrepreneurial life’s not for the faint of heart. It’s like taming a wild thing; best hunker down and hold on tight for the ride. And what a fantastic ride it’s been.

Mark’s first business operated out of tiny, windowless dirt-cheap offices in the Hillsdale area of Portland, Oregon. Arts Marketing Association aimed at helping performance arts groups grow their paying audience members across the country.

BC (before children), Mark and I operated Black Diamond Films. In the early 90’s it was the second most successful video production company in Portland (you try harder when you’re number two).

Then came the babies.

Our first son was born in 1993, two more sons followed within five years. While I became a full-time mother of three, Mark launched yet another business. His new company, e/y/e/s/c/r/e/a/m interactive, was an online advertising agency that cashed-in big on the dot-com wave. They produced some of the most innovative and creative campaigns of the time and worked with everyone from Disney to P&G. The company was listed as one of the top 20 agencies in the world, according to AdWeek magazine.

Then the dot-com bubble burst and Mark pivoted once again. This time he, and partner Josh Friedman co-founded NedSpace, a coworking space for startups, designers, and founders. NedSpace has been an enormous success and celebrates 12 years in business next February.

Covid-19 changed our lives in 2020. Now that folks are quarantined and working remotely, business is slower at NedSpace, leaving Mark with a little time on his hands.

My husband with time on his hands? (Head slap!) I should have seen this one coming.

In June, we were at the Oregon coast, enjoying our morning coffee, when Mark dropped some news. He wanted me to sign off on a new project; it was something he’d wanted to do for 18 years, but never had enough time to devote to it — until now.

“I’m going to start 31 businesses in 31 days — it sounds crazy, but I know I can do it,” he said, and I believed him. He explained that he wanted to show (through extreme examples) that you don’t need high-interest bank loans or VC’s to fund your business idea, you need to Just Do it (Nike hat tip). Mark wanted to crush the old conventions and show potential founders a different way, maybe even a better way.

Every business Mark’s started since 1989 has been cashflow positive within 90 days or less. He started each with our capital and his (sometimes our) own sweat. Mark’s been successful and has enjoyed coaching startups at NedSpace and helping other founders throughout the Pacific Northwest. But now he wanted to do it on a much bigger scale.

Geez! And here I thought the guy was contemplating retirement — Oy!

Although I didn’t voice my concerns, my stomach churned at the idea. Mark would be wholly consumed and unavailable for an entire month as he rolled out his plans. Here we are in the middle of a global pandemic, and he wanted to take this on? How about baking some bread or gardening?

Crazy time to start 31 businesses? You bet! Did I think Mark could pull it off? You bet I did. I’d seen this man do extraordinary and miraculous things throughout our lives together. If anyone could start 31 business in 31 days, Mark could do it. He had my complete support and cooperation.

To start, Mark would be writing a background story every day to introduce each day’s business. People following his journey on Twitter, LinkedIn, Facebook, and Medium could keep track of what he was doing. Not only that, he’d make available a Google document that outlined each day’s progress. Everything would be 100% transparent. Would there be mistakes? Yes. Would things get messy? Yes. And all of those highs and lows would be documented, for the world to see, in real-time.

The first days were fairly brutal for Mark, and one thing became crystal clear; he needed an editor. He’s a great writer but had no time to devote to editing. Enter his wifey, the writer, to the rescue. Every day, I get the first peek at that day’s business as I edit his articles. They’ve widely varied from custom axe-throwing targets to specialized whiskey koans, hand-blown by Chihuly-trained craftsmen.

Next, he needed photos, a visual to pair with each article as well as documentation. Mark wasn’t keen on using Unsplash or Pixabay as a source for photos — he wanted originals. Enter wifey; the writer turned photographer. As Mark’s wife, I’m used to wearing a lot of different hats. We have run businesses over the years, and while most people shudder at the thought of working with their spouse, we know how to be an incredible team and have a blast doing it.

It’s now August 27th, with four days left in the month. Four more days of copywriting, editing, and photoshoots — four more days of eating, sleeping, and breathing this project. Mark’s been consumed night and day, keeping his head in the game for the past 27 days. Some might say he’s a masochist, but he works best with his feet to the fire, so he’s in his element.

I’m proud of him for attempting something so big and so worth doing. He’s always put himself out there for others. Be it helping women entrepreneurs in Africa grow their businesses or helping local underrepresented founders, women, POC, LGBTQ share their stories. And now he’s using his creative talents to encourage fledgling startups to pursue their dreams in a whole new way.

We’re now in the home stretch of the first leg of the journey, and I’m excited to see what the next four days hold. Join me If you’re interested in playing along at home (I’ll bring the wine and popcorn) and watching as my husband continues this crazy journey.

Tonight, we’re going to the beach at sunset to light a chair on fire.

Next, he’s got 90 days to make each business cash flow positive. Hold on tight, it’s bound to be a wild ride.