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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

How remote work has changed over the last decade

(BUSINESS NEWS) let’s reflect on how remote working and telecommuting has changed in recent years and look to how it will continue to change in the 2020s.



remote at home

As someone who often works remote, it’s interesting to see how much that means for work has evolved. The increase in commonality has been steady, and shows no signs of slowing down. Go Remotely has developed an insightful graphic showing the changes in trends regarding remote work over the years.

“For decades, the established economy dictated that you should pick one job, visit the same office for the next 40 years, and then retire,” reads the graphic’s intro. “However, recent remote working stats suggest the working world might be in for some revolutionary changes.”

From there, the graphic is broken down into five facets: Flexible Workspace Policy, Entrepreneurial Minds, Telecommuting is a Growing Trend, The Role of Companies in the Remote Working World, and The Future of Telecommuting.

With Flexible Workspace Policy, its suggested that telecommuting could be a solution for costly issues including lack of productivity caused by employee distractions, health problems, etc. It is said that employers lose $1.8 trillion annually due to these issues.

The end of 2018 found 35 percent of the US workforce working remotely. This is only expected to climb. Ten percent of employees don’t know if their company offers flexible work policies (this is something to check into!)

Bills and laws for virtual jobs passed by governments reflect the need for accessibility, economic stability, and emigration concerns. Companies with flexible work policies have reported seeing increases in productivity and profits. (Funny those both start with pro, no?)

With Entrepreneurial Minds, a few interesting things found include: remote workers are less likely to take off if they are sick, the majority reports better productivity when working alone, the majority reported lower stress levels. However, there is a problem with not being able to unplug after work which is an issue for some.

Telecommuting is a Growing Trend finds that there has been a seven percent increase between 2012 and 2016, with the majority (80-100 percent) reporting they work remotely. Industries seen embracing remote work include: transportation, computer/information systems/mathematical, arts/design/entertainment/sports/media, finance/insurance/real estate, law or public policy, community/social services, science/engineering/architecture, manufacturing or construction, healthcare, education/training/library, and retail.

The Role of Companies in the Remote Working World finds that the pros to hiring remote workers includes: finding talent outside of your geographic area, improves retention on work/life balance, increases productivity by decreasing commute time, and saves money by requiring less office space. The cons include lack of timeliness when it comes to receiving information from employers.

Finally, the Future of Telecommuting suggests that in 2020 the US mobile worker population will surpass 105 million (and will account for 72 percent of the US workforce). Hiring managers predict that telecommuting will increase tremendously, most skills will become even more niche over the next decade, and many think that 38 percent of their full-time workers will be working remotely in the next decade.

How do you feel about the increase in remote working and telecommuting?

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Business News

ClickUp team productivity app is gorgeous and wildly efficient

(BUSINESS NEWS) Seeking to improve your productivity and speed up your team, ClickUp is an inexpensive option for those obsessed with efficiency.




Back again to obsess over productivity apps – ClickUp, is a project management tool seeking to knock the frustration out of PM. It’s getting some good reviews, so I gave it a try for a week by setting up my current job search as a project and getting a feel for the app. And as you’ve read in my other reviews, we will address features and design.

On the feature front, ClickUp offers a pretty standard set up of tools for a productivity app. What stands out first and foremost are the status options. In general, most productivity statuses are simple: not started, started, in progress, done, etc.

But ClickUp lets you set up custom statuses that match your workflow.

For example, if you’re doing instructional design projects, you may assign projects based on where they are flowing in an ADDIE model, or if you are a Realtor, you may have things cataloged by sold, in negotiation, etc.

Customization is king and custom status is the closest you get to building your own app. And if you like it simple, you don’t have to customize it. The assigned comments feature lets you follow up on specific comments that originate action items – which is useful in team collaborations.

You can also assign changes to multiple tasks at once, including changing statuses (I would bulk assign completion tasks when I finished applications that I did in batches). There a lot of features here, but the best feature is how the app allows you to toggle on and off features that you will or won’t use – once again, customization is front and center for this platform.

In terms of design and intuive use, ClickUp nailed it.

It’s super easy to use, and the concept of space is pretty standard in design thinking. If your organization uses Agile methodology, this app is ready for you.

In terms of view, you can declutter the features, but the three viewing modes (list, box, and board) can help you filter the information and make decisions quickly depending on what role you have on a board or project. There is also a “Me” board that removes all the clutter and focuses on your tasks – a great way to do focused productivity bursts. ClickUp describes itself as beautifully intuitive, and I can’t disagree – both the web app and mobile app are insanely easy to use.

No complaints here.

And the horizon looks good for ClickUp – with new features like image markup, Gannt charts (!!!!!! #nerdalert), and threaded comments for starts.

This application is great, and it’s got a lot of growth coming up to an already rich feature base. It’s free with 100MB of storage, but the $5 fee for team member per month that includes team onboarding and set up (say you’re switching from another platform) and Dropbox/Google Docs integration? That’s a bargain, Charlie.

ClickUp is on the way up and it’s got it all – features, a beautifully accessible UI, relentless customization, and lot of new and upcoming features. If you’re into the productivity platform and you’re looking for a new solution for your team, go check it out.

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Business News

Should you alter your business travel due to the Coronavirus?

(BUSINESS NEWS) Got a business trip coming up? Worried about the coronavirus spoiling those plans? Stay up to date and safe with this cool site!



travel coronavirus

The Center for Systems Science and Engineering (CSSE) at John Hopkins University has created a website that tracks one of the biggest trends of 2020: the coronavirus. Also known as 2019-nCoV, this disease has already spread to over 40,000 confirmed cases worldwide, with over 900 deaths (as of when this article was published, anyway.)

Not to mention, the United States Center for Disease Control and Prevention (CDC) notes that we still don’t know exactly how the virus spreads from person-to-person. In fact, there’s quite a bit we don’t know about this disease and although some people are reported as recovered, it’s only a small fraction compared to how many are sick.

So, what’s so great about this tracker? Well, first of all, it updates in real time, making it easy to keep track of everything we know about confirmed cases of the coronavirus. It’s chock full of statistics and visuals, making the information easy to digest. Plus, with a map front and center, it lets you know exactly where there have been reported outbreaks – and how many people have been diagnosed.

Because the site sticks to cold hard facts like statistics and maps, it also means you can avoid the racism and general panic that’s accompanied news of this outbreak.

This is a great tool for staying informed, but it’s also extremely helpful if you’re going to be traveling for work. As the virus continues to progress, you’ll be able to see just how many cases of coronavirus there are in the areas you’re planning to visit, which will allow you to plan accordingly. Even if you don’t feel the effects, you can still risk passing it to other people.

(In fact, the CDC recommends those traveling from certain areas in China practice “social distancing” when they return to the US, avoiding public spaces like grocery stores, malls and movie theaters.)

Of course, if you have something planned several months from now, don’t cancel your conference plans just yet. A lot can happen in that amount of time, so avoid the urge to check the website every couple hours. It’s supposed to be a tool for staying informed, not staying stressed out.

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