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Sailing like entrepreneurs: High-seas adventure, education await family of Workbar founder

Ben Jacobson and his mother, Renee Bushey, showed flags of the various countries the family plans to visit.Bill Jacobson

Bill Jacobson wasn’t sure he wanted me to write about his yearlong voyage around most of the planet, which starts this week.

But he may need an experienced mariner or two to join his crew for part of the journey.

So I told him this column might serve as an extended help wanted ad. What if I found him a crew member who’d not only help him cross the Pacific safely, but become a lifelong friend?

“Let me ask my wife,” Jacobson said, wisely. (She gave the go-ahead.)

Jacobson is a serial entrepreneur. A decade ago, he founded Workbar, a network of eight shared office spaces around the Boston area. Before that, he had started a company that enabled online shoppers to pick up their orders at a local retailer, and another that helped publishing companies deliver personalized e-mail newsletters. Both were later acquired.


One of those acquisitions gave Jacobson enough money to buy a long-distance sailing yacht made by J/Boats of Newport, R.I. He named the 46-foot vessel, and upon getting married in 2002, set off to the Caribbean with his spouse, and then to the Mediterranean. The trip spanned 18 months.

The route planned for the Verbena is an estimated distance of 17,000 miles.Bill Jacobson

After having children, Jacobson started thinking about doing a similar voyage with the family. “But work-wise,” he says, “it just wasn’t practical for me or my wife, Renee [Bushey],” a labor attorney at the Boston law firm Feinberg, Campbell & Zack. His son and daughter were fast approaching their teen years. “It looked like it wasn’t going to materialize,” he says.

But in May 2018, Jacobson handed the CEO role at Workbar to Sarah Travers, a former employee of Regus, one of the biggest players in shared offices. He became a board member. Plans started to take shape — often discussed onboard the

“I wanted to sail in the Pacific Ocean,” Jacobson says. “The climate is changing, and the ocean has been changing since our 2002 trip. It will change again by the time my kids do something like this again — if they do. We talked about doing a bunch of ‘citizen science’ projects with the kids along the way,” to learn about climate change and how it affects sea creatures.


Bill JacobsonAram Boghosian for The Boston Globe

As for himself, Jacobson says he wasn’t exactly burned out, but after handing the reins to Travers, it felt like “a good time to clear my head and get some world perspective.”

“The kids at some point were just like, ‘Dad, tell me if we’re doing this or not,’ ” Jacobson says.

He and Bushey looked into how a yearlong trip would affect their children’s school progress. (Both attend Boston Latin School.) Bushey arranged to take a leave from the firm. Jacobson found a used 2007 boat for sale in Denmark that looked suitable for the trip.

“It’s a strong, oceangoing boat, made in Denmark by a company called X-Yachts,” Jacobson told me over lunch in the Back Bay last month, after his trip to Scandinavia to check on the last-minute preparations and some upgrades at the boatyard. Those included new navigational gear and solar- and hydropower generators, both renewable sources of electricity.

He and Bushey rented out their place in Charlestown, sold the family car, and found a caretaker for the cat, Freckles, who didn’t seem to love sailing as much as everyone else did. (They tried.) The four family members arrived in Denmark late last month and took the boat, dubbed Verbena, out for a for a few short shakedown sails.


The plan was to depart from Haderslev, Denmark this week, but stay close in case there was a need to return to the X-Yachts factory. Then, to the Netherlands, England, Spain, and Portugal.

06kirsner - The planned route. The estimated distance is 15,000 nautical miles, or about 17,000 miles. (Bill Jacobson)Bill Jacobson

“What they say about the route is that you go south until the butter starts to melt — to Portugal and the west coast of Africa — and then you turn right,” to head toward the Caribbean, Jacobson explains. From there, the plan includes a trip through the Panama Canal, around January, and visits to the Galapagos Islands, Tahiti, and Fiji. It concludes in Mackay, Australia, near the Great Barrier Reef.

Jacobson hopes to sell the boat in Australia and have everyone back in Boston for the start of the 2020 school year.

Like the entrepreneur (and electrical engineer) that he is, Jacobson has some ideas he wants to develop while at sea. Among them: “Can we make a different style of autopilot for boats that uses the video input from cameras that look at the shape of the sail?” It would make course adjustments the way sailors do, potentially improving on the accuracy of autopilot systems.

And as someone who has built a network of shared workplaces for dozens of people who work on different projects, Jacobson is interested in developing new technology solutions for those heterogeneous workplace communities.


His daughter and son, 12 and 14, will be working on a distance-learning curriculum from a company called Oak Meadow, as well as studying ocean plastic levels, zooplankton, and sea water chemistry by taking surface samples and measurements.

When you’re returning to work after Labor Day, Jacobson and his family are likely to be transiting Germany’s 60-mile Kiel Canal, on their way to Amsterdam.

Jacobson says he’s still on the hunt for an experienced sailor or two to join the family in November, when they cross the Atlantic, and in March, on the trip from the Galapagos to the Marquesas Islands in French Polynesia. Both are at least two-week passages, so Jacobson says “it’s unlikely we’ll do it with someone we don’t already know, but it may be fun to see what comes out of the article.”

He’d also be happy to see friends from the Boston tech community in the various ports they’re visiting. You can follow along, or get in touch, at

Scott Kirsner can be reached at Follow him on Twitter @ScottKirsner.