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OB Jacobi: business leader showcase

By getting to know how business leaders tick, we can relate and learn from their experiences to make each of us better leaders ourselves. This interview with OB Jacobi, President of Windermere Real Estate Company is entertaining and inspiring.

ob jacobi

ob jacobi

Tell us about yourself and your work.

I work in a family business, Windermere Real Estate, which makes it hard to define exactly what work entails day to day and week to week. If you’re in a family business, you do whatever it takes at that time to get the job done.

I’ve been at Windermere for 16 years, but it wasn’t my first career, if you will. I owned a bar for nearly three years after I left college. My dad believed that real-life experience is the best way to learn, so that’s what I did.

While I’m listed as president of Windermere Real Estate Company, we really don’t pay much attention to job titles. It’s more important that we just do what needs to get done.

Our executive team also includes my brother-in-law Geoff Wood (chairman) and my sister Jill Jacobi Wood (president, Windermere Services Company), and fortunately, while our passions follow different paths, we complement each other really well.

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Geoff likes to focus on the financial side of the business, Jill is a great people person and I get excited – make that very excited – about technology and how it can change our industry.

This diversity leads to great chemistry that helps us get along in the workplace and enables us to bounce ideas off one another. But in reality, each person is running their own mini-company within the larger Windermere brand.

Walk us through a typical day in your life.

Well, like most people in the real estate industry, it’s sometimes hard to define a ‘typical day,’ but here goes. For me, there are three business elements in every day.

Our family owns six Windermere offices, which means I have all of the opportunities and challenges that any owner faces. On any given day, I may be assisting one of our agents with the business of buying and selling homes.

We also own the franchise division of Windermere Real Estate. So I may be visiting at one of our offices, talking with agents, brokers and owners about different company programs and how they can benefit from them.

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I’m also involved in the technology side of Windermere Real Estate, and that cuts across multiple layers of our overall business. It’s a large part of what I do daily with the company.

All in all, it’s a full day and I try to allocate time every day to each of these two buckets. And like most of us, I find myself looking at financial numbers after dinner because there aren’t enough hours in the day to get everything done.

Where were you raised? Where all have you lived?

I’m a Seattle boy, born and bred, with three biological sisters and two step-sisters. I was born in Laurelhurst, a close-in Seattle neighborhood, and moved to Windermere, a nearby neighborhood, when I was three. When I was 10, my parents got a divorce and I moved to Bainbridge Island, yet another community near Seattle, to live with my Mom.

When I started 7th grade, I moved back to Seattle to live with my Dad. After high school, I moved to Boston and did a couple of internships before going to college. I worked at a radio station and at a child day care program.

I moved back to Seattle to attend University of Washington. While at U-Dub, I realized that school isn’t necessarily my forte – I’m much better working in real life situations. So during my junior and senior years, I had a job in the property management division at Windermere.

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During my senior year, I left Seattle to travel around Europe with friends. When I returned after four months, I was looking at the possibility of returning to the property management job when something interesting came up.

A restaurant and comedy club in downtown Seattle was going out of business and the owners basically had walked away from all of their equipment and furniture. I partnered with a friend who had restaurant experience and we bought the club. Six months later, I bought out my partner.

I ran the place for nearly three years, doing the insane schedule and work hours of the restaurant life until my wife came to me and told me that I was killing myself. She was right. So I sold that business and started a café with her.

After six months, my sister Jill said to me, ‘Why don’t you just join the company?’ So I did, 16 years ago.

How did you get into your current career?

As I said, Windermere is a family business. My dad started the company in 1972 and I was born in 1970. So I’ve lived and breathed real estate my whole life. Once I got that restaurant thing out of my system, it was a natural progression.

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What is something unique that you do to balance work and life?

That’s a great question. For me, I have to get out of Seattle. One of my passions is boating and for two to three weeks each summer, we take off and head north up Puget Sound in our boat. I also love the outdoors. We have a family cabin in Leavenworth, up in the mountains east of Seattle. It’s a great place to go hiking, skiing and river rafting.

What keeps you up at night?

Technology is moving so fast that it’s hard to keep up personally, but even harder to keep up with how it can impact your business, both positively and negatively.

Specific to the real estate business, it’s making sure that my people earn enough to make a good living. Real estate has been so challenging in the past few years that it’s hard for people to make a living. And the possibility of a double-dip recession really makes me nervous.

If you could spend one day in the life of another leader, who would it be? Why?

Bill Gates. I’d love to see how he did it. I’d also love to spend time with anyone who’s done a successful software start-up to learn how they grow a company by taking the right risks. There would be a lot of things to learn that I believe can apply to real estate.

What tools can you not live without?

That’s easy – my iPhone. Frankly, I would love to not have to live with it, but we’re so connected these days that it creates anxiety when I don’t have it. Imagine that – the world has created anxiety over your telephone.

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I love this thing, but the flip side is that I wish I wasn’t connected all the time. That’s one of the reasons that I try to escape by getting out of town – that’s pretty much the only time my iPhone isn’t connected.

At age 15, what did you want to be when you grew up?

Oh my god, no! At age 15, I was rebelling against my parents – something that most of us go through, I think. For as long as I can remember, I’ve always had a job and I actually was working in construction at that time. But I took a summer off when I was 15 and took a NOLS course (National Outdoors Leaderships School) in 1985.

I thought that NOLS was the greatest thing since sliced bread. So at age 15, I wanted to be a fishing guide or a mountaineer.

What about you would most not believe unless they knew you?

I was a cook at Red Robin and I love to cook.

What inspirational quote has stuck with you the longest?

‘What would you be able to achieve if you knew you couldn’t fail?’

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1 Comment

1 Comment

  1. laniar

    August 30, 2012 at 10:04 am

    I love that your rebellion included being a leader. Awesome! Great read, and thank you for sharing with us, OB!

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