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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.

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.

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.

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.

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.

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?’

The American Genius is news, insights, tools, and inspiration for business owners and professionals. AG condenses information on technology, business, social media, startups, economics and more, so you don’t have to.

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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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Business News

Why a well-crafted rejection email can save your brand, and your time

(BUSINESS NEWS) Job hunting is exhausting on both sides, and rejection sucks, but crafting a genuine, helpful rejection email can help ease the process for everyone.



Woman sitting at computer with fingers steepled, awaiting a rejection email or any response from HR at all.

Nobody likes to hear “no” for an answer when applying for jobs. But even fewer people like to be left in the dark, wondering what happened.

On the employer side, taking on a new hire is a time-consuming process. And like a box of chocolates, you never know what you’re going to get when you put out ads for a position. So once you find the right person for the role, it’s tempting to move along without further ado.

Benn Rosales, the CEO and co-founder of American Genius, offers an example of why that is a very bad call.

Imagine a hypothetical candidate for a job opening at Coca Cola – someone who’s particularly interested in the job, because they grew up as a big Coke fan. If they get no response to their application at all, despite being qualified and sending follow-up emails, their personal opinion of the brand is sure to sour.

“Do you know how much effort and dollars advertising and marketing spent to make [them] a fan over all of those years, and this is how it ends?” Rosales explains. This person has come away from their experience thinking “Bleep you, I’ll have tea.”

To avoid this issue, crafting a warm and helpful rejection email is the perfect place to start. If you need inspiration, the hiring consultants at Dover recently compiled a list of 36 top-quality rejection emails, taken from companies that know how to say “no” gracefully: Apple, Facebook, Google, NPR, and more.

Here’s a few takeaways from that list to keep in mind when constructing a rejection email of your own…

Include details about their resume to show they were duly considered. This shows candidates that their time, interests, and experience are all valued, particularly with candidates who came close to making the cut or have a lot of future promise.

Keep their information on file, and let them know this rejection only means “not right now.” That way, next time you need to make a hire, you will have a handy list of people to call who you know have an interest in working for you and relevant skills.

Provide some feedback, such as common reasons why applicants may not succeed in your particular application process.

And be nice! A lack of courtesy can ruin a person’s impression of your brand, whether they are a customer or not. Keep in mind, that impression can be blasted on social media as well. If your rejections are alienating, you’re sabotaging your business.

Any good business owner knows how much the details matter.

Incorporating an empathetic rejection process is an often-overlooked opportunity to humanize your business and build a positive relationship with your community, particularly when impersonal online applications have become the norm.

And if nothing else, this simple courtesy will prevent your inbox from filling up with circle-backs and follow-up emails once you’ve made your decision.

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Business News

Are Gen Z more fickle in their shopping, or do brands just need to keep up?

(BUSINESS NEWS) As the world keep changing, brands and businesses have to change along with it. Some say Gen Z is fickle, but others say it is the nature of change.



Gen Z woman shopping outside on a laptop.

We all know that if you stop adapting to the world around you, you’re going to be left behind. A recently published article decided to point out that the “fickle” Gen Z generation are liable to leave a poor digitally run site and never return. Now of course we’ve got some statistics here… They did do some kind of due diligence.

This generation, whose life has been online from almost day one, puts high stakes on their experiences online. It is how they interact with the world. It’s keyed into their self-worth and their livelihoods, for some. You want to sell online, get your shit together.

They have little to no tolerance for anything untoward. 80% of Gen Zers reported that they are willing to try new brands since the pandemic. Brand loyalty, based on in-person interaction, is almost a thing of the past. When brands are moved from around the world at the touch of your fingertips there’s nothing to stop you. If a company screws up an order, or doesn’t get back to you? Why should you stick with them? When it comes to these issues, 38% of Gen Zers say they only give a brand 1 second chance to fix things. Three-quarters of the surveyed responded saying that they’ll gladly find another retailer if the store is just out of stock.

This study goes even further though and discusses not just those interactions but also the platforms themselves. If a website isn’t easy to navigate, why should I use it? Why should I spend my time when I can flit to another and get exactly what I need instead of getting frustrated? There isn’t a single company in the world that shouldn’t take their webpage development seriously. It’s the new face of their company and brand. How they show that face is what will determine if they are a Rembrandt or a toddlers noodle art.

The new age of online shopping has been blasted into the atmosphere by the pandemic. Online shopping has boosted far and above expected numbers for obvious reasons. When the majority of your populace is told to stay home. What else are they going to do? Brands that have been around for decades have gone out of business because they didn’t change to an online format either. Keep moving forward.

Now as a side note here, as someone who falls only just outside the Gen Z zone the articles description of fickle is pompous. The stories I’ve heard of baby boomers getting waiters fired, or boycotting stores because of a certain shopkeeper are just as fickle and pointed. Nothing has changed in the people, just how they interact with the world. Trying to single out a single generation based on how the world has changed is a shallow view of the world.

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Chasing Clubhouse success? How the audio chat room trend affects products

(BUSINESS NEWS) It is inevitable that when a new successful trend comes along, other companies will try to make lightning strike twice. Will the audio chat room catch on?



Smiling woman seated in dark room illuminated by lamp and phone light, participating in audio chat room.

Businesses are always about the hot new thing. People are the always looking for the easiest dollar with the least amount of effort these days. It tends to lead to products that are shoddy and horribly maintained with the least amount of flexibility in pleasing their customers. However, you also have to look at the customer base for this as well. You follow where the money is because that’s where its being spent. It’s like a merry-go-round, constantly chasing the next thing. And the latest of these is the audio chat room.

During the pandemic the entire world saw an eruption of social audio investments. Silicon Valley has gone crazy with this new endeavor. On the 18th of April this year, Clubhouse said it closed on some new funding, which was valued at $4 billion for a live audio app. This thing is still in beta without a single penny of revenue!

The list of other companies who have pursued new audio suites (either through purchase or creation) include:

  • Facebook
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This whole new audio fad is still in its infancy. These social media and tech giants are all jumping headlong into it with who knows how much forethought. A number of them have their own issues to deal with, but they’ve put things aside to try and grab these audio chat room coattails that are running by. It’s a mix of feelings about the situation honestly. They are trying to survive and keep their customers.

If a competitor creates this new capability and they stay stagnant then they lose customers. If they do this however without dealing with their current issues then they could also lose people. It’s an interesting catch 22 for people out there. Which group do you fall in? Are you antsy for a new toy or are you waiting for one of these lovely sites to fix a problem? It’s another day in capitalism.

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