All the Right Moves

James Rowley, CEO/cofounder of Woolloomooloo, looks back on a life well lived.

Dear 15-year-old James…Growing up in the late ’70s and ’80s in ’Straya (Australia for non-locals) is a charmed life. Your red brick house among the gum trees, kookaburras laughing in the background, skateboarding in the cul-de-sac, bombing your sisters in the pool, raiding fridges from house to house with best mates Bruce and Richie and leaving a trail of pool water in your wake…it’s the time of your life, kid. Soak it in because this joyous phase can’t be replicated. But know that one day you’ll be 50 and you’ll think, “Man, I had it good.”

In your spare time, your entrepreneurial spirit soon kicks into gear. You repair lawn mowers out of a shipping container on a busy intersection and refurbish golf clubs at a local course. Figuring out how businesses are built and work will become a recurring theme in your future footwear industry career. For now, though, you’re set on becoming a golf champion or, plan B, a tennis pro. You’re cool with whatever happens first.

Apart from schoolwork, life is grand. Somehow you squeak by while prioritizing good times and friends—a quality that, believe it or not, will hold you in good stead in your career. First, though, comes life’s big move No. 1. In 1987, Dad announces the family is shipping off to Seoul, South Korea, for his job with IBM. You’re 16 and quite happy in ’Straya. But once you learn it’s a coed school with no uniforms, you’re on board. What matters now, other than golf and tennis, is meeting girls.

James Rowley is game for whatever life serves up.
James Rowley is game
for whatever life serves up.

You make friends easily—the Aussie accent is a hit! You also pick up Korean quick, speaking with taxi drivers, bartenders (don’t tell Mom and Dad), and hanging out with friends. In a matter of months, you can order from a menu, give directions, get out of trouble, haggle, and swear proficiently. Itaewon is the local shopping mecca/hangout and where you see more sneaker styles than you can ever imagine. Kicks are cool, but you still prefer the social life of a teenager. When it comes to thinking about your future, all you know is it better be fun and, preferably, owned and run by you.

Post high school you fumble around for a couple of years trying different countries and professions. Stops include a marine mechanic followed by a plant manager for a bull bar manufacturer in Australia. Then it’s a tennis coach in Greenwich, CT. In 1996, you take the college route, enrolling in Pace University to study business and marketing while serving as a tennis pro during the summers. It’s at this point that you realize: “I need more money!”

After graduating, you look for any job. With New York at your doorstep, you take a job in communications and marketing at Ogilvy & Mather. Over the next five years, you create and manage 360 Live, an on-site brand and pre-event marketing team. You see a definite career path here. But then a friend from high school mentions he wants to open a shoe store. The opportunity to branch out on your own is too good to pass up. Life’s big move No. 2 is upon you.

In 2001, you ship off to Austin, TX, where you found Two Dots Marketing, a multi-faceted footwear marketing company that, over the next nine years, spans retail, wholesale, and product development arms. It kicks off with Ven Shoe Salon, a high-end women’s boutique. You meet lots of shoepeople and get to know the industry well. The learning curve is steep but exhilarating. You aren’t just selling shoes, you’re learning about what fills the marketplace, how much does marketing matter, the difference between brand and product, what sells and what flops, etc. You then develop a tech-based sales platform servicing seven brands including Robert Zur, Bolo by Born, United Nude, and Kork-Ease.

Two Dots is solid. You’re young, successful, and holding out for someone who’ll challenge and support you through your entrepreneurial endeavors. Enter Elena. Your future wife, who works for Stuart Weitzman, knows more about shoes than you. She is very helpful with Two Dots. By 2005, you expand to three store locations, a wedding date is set, and a new endeavor is dominating your mind space: the relaunch of Kork-Ease. This marks life’s big move No. 3.

What started out as a side hustle quickly dwarfs your retail business and takes your focus to wholesale. Relaunching Kork-Ease is the culmination of all your learnings to date: the importance of brand, relationships, and good ole hard work. In just five quick years, Kork-Ease needs a new parent company to reach its next growth stages. A sale to HH Brown is orchestrated in 2009. You’re back in your old stomping grounds of Greenwich as brand CEO. Over the next seven years the business grows and you take on the role of senior VP of sales and marketing for the Born group.

Then it’s onto new opportunities. Your first stop is managing Geox USA, a common “next stop” for footwear execs, you later discover. Fair warning: life has bumps in the road. Then it’s on to CEO of Mephisto USA, another bump. After 10 years in the corporate world, your entrepreneurial itch is too great to ignore. You miss being fully in charge. This marks life’s big move No. 4: the launch, in 2020, of Woolloomooloo shoes. The Merino wool-based athleisure brand combines your love of kicks, comfort, and carefree ’Straya lifestyle. Launching a brand amid a pandemic, though, is no picnic. (Side tip: invest in surgical mask manufacturers in 2019.) Everything you’ve ever learned is put to the test while a new industry playbook is being written. You find your footing, though! More importantly, your family that now includes your beautiful wife of 21 years, two great kids, a dog, a house, etc., is healthy. Some things are more important than shoes.

It’s been a great ride so far. Know that none of it would’ve been possible without many mentors who’ve guided you on a more direct path of success. Fred Bright, Mickey Rosmarin, Paul Mayer, and Tom McClaskie, to name a few. But nothing tops the endless support from Mom and Dad. Thank them for me.

Until we meet again, keep dreaming and striving. Be grateful and remain optimistic. Life is a journey. Love every turn.

Good on ya mate, James.

The February 2025 Issue

Read Now