These married former Apple execs used lessons learned from Steve Jobs to pivot their small business during Covid

When husband and wife Jim Bean and Christine O’Sullivan realized their dream of owning a Napa Valley winery in January 2019, after decades working at tech giant Apple, they couldn’t imagine the tremendous challenges the Covid-19 pandemic would bring for small businesses just a year later. 

a person posing for the camera: Christine O'Sullivan and husband Jim Bean are former Apple executives who bought Napa Valley's Brand winery in 2019.

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Christine O’Sullivan and husband Jim Bean are former Apple executives who bought Napa Valley’s Brand winery in 2019.

“We started in year one with incredible momentum…then Covid hit,” says O’Sullivan, who with her husband, Bean, is the co-owner of Brand, a high-end winery and vineyard on a 110-acre estate in St. Helena, California that typically turns out about 2,000 cases of wine per year.

a view of a house: Brand features a winery and 15 planted acres of grapes on a 110-acre Napa Valley estate.

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Brand features a winery and 15 planted acres of grapes on a 110-acre Napa Valley estate.

Nearly half wine industry business owners found 2020 to be one of the most challenging years or the most challenging year they’ve ever had, according to a recent survey. But Bean tells CNBC Make It that Covid was actually “a curse and a gift.” That’s because it forced the couple to quickly pivot the business, launching a series of virtual wine tastings aimed at CEOs and executives, as well as creating a direct-to-consumer sales push where customers who buy one bottle of wine can gift a free bottle to a first-responder or a teacher. 


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The change is working. While Bean and O’Sullivan declined to discuss specific revenue figures, “we think we’re going to come out of this year stronger than ever, with our direct-to-consumer base,” Bean says. “We’ve learned a lot of things and we’ve built a lot of great momentum.”

And Bean and O’Sullivan say was their careers at Apple that directly influenced the moves that Brand has made. They were especially inspired by some of the lessons they learned from Apple co-founder Steve Jobs during their time working under him.

The winery is the second chapter in the careers of Bean and O’Sullivan, who met in the late ’90s while both working at Apple. O’Sullivan spent 15 years with the company as an executive on the software engineering team who helped manage the release of the Mac Os X operating system before retiring in 2009 to focus on raising the couple’s two children (their son is a freshman in college and their daughter is a high school senior). Bean, meanwhile, worked at the company for about two decades and spent time as the vice president of finance and then the vice president of retail before retiring in 2018.

After years of visiting Napa Valley on vacation, Bean and O’Sullivan bought a second home there in 2007. They even bought a small vineyard and began what Bean calls “a little family wine project,” which meant growing their own grapes, some of which the family sold to local wineries and some they used to make wine for their own consumption. In that sense, they were following local tradition, according to Bean, who says “everybody in Napa makes wine.”

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Once they had both retired from Apple, the couple decided to move to Napa full time and they felt they had one more big project in them. “[Christine] shipped a lot of operating systems and I sold a lot of iPhones,” Bean says. “But after a while, sometimes you just have a desire to do more with your life.”

Bean and O’Sullivan tapped into their “ample resources” accumulated during their respective careers and bought Brand from the winery’s previous owners in January 2019 for an undisclosed amount.

Lessons from Apple kicked in

“Our Apple background and the concepts that we really brought from Apple to Brand kicked in” early in the pandemic, O’Sullivan says.

Bean vividly remembers first meeting Jobs during his job interview for the company. “I was there in a suit and tie and he had a black t-shirt, cut up army fatigues and his Birkenstocks in his hands,” Bean says. (Jobs was known to favor wearing sandals or bare feet around the office.)

It was Jobs’ “passion and conviction” that he could rebuild Apple that inspired Bean to come along for the ride. (Current Apple CEO Tim Cook has told a similar story about how Jobs convinced him to join the company in 1998 by passionately outlining his vision for turning Apple around.)

And when it comes to their time at Apple as inspiration during the pandemic, Bean points back to their early years at Apple, shortly after Silicon Valley was reeling from the 2000 dotcom bubble bursting. “Tech companies were laying off people and just trying to cut expenses … and, Steve said, ‘We’re not going to do that,'” Bean recalls.

In fact, Jobs later said that Apple declined to do widespread layoffs in the early 2000s because he felt his employees were too valuable to let go, and he instead opted to increase the company’s research and development budget “so that we would be ahead of our competitors when the downturn was over,” Jobs told Fortune in 2008.

“Those were the days when [Apple] invented the iPhone and the iTunes store and a lot of other things that led to the longer term success of Apple,” says Bean, who adds that he and O’Sullivan wanted to take a similar path during the pandemic by pivoting to new ways of bringing in extra revenue that could keep Brand’s staff of four full-time workers employed. Bean and O’Sullivan say they have not had to lay anyone off.

“In the long term, our primary goal was to keep our staff employed …  And we might never go back to normal. What is that? So we’ve got to figure out how we can go through ebbs and flows and figure out how to survive,” O’Sullivan says.

“We knew we had to pivot quickly. We had to think very differently. And we had to focus,” she adds. Here, O’Sullivan even points to a famous Jobs quote about how focusing means “saying ‘no'” to a lot of good ideas that aren’t right for your business so that you can carefully zero in on the right ideas.

a close up of a knife: Brand's cabernet sauvignon is the Napa Valley winery's flagship wine.

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Brand’s cabernet sauvignon is the Napa Valley winery’s flagship wine.

“What that allowed us to do was to, kind of, slow down and … really go deep into some things that have paid off this year and that are also going to pay off in the future,” he says.

One pivot the winery made creating a program called #FromBrandWithLove, where customers pay $150 for a 2016 bottle of Brand’s Napa Valley BRIO, “an estate-produced Bordeaux-style red blend of Cabernet Sauvignon, Cabernet Franc and Petit Verdot,” according to the winery’s website, and Brand sends a free bottle to a teacher or first-responder of the customer’s choice. The $150 package has a $300 value, the business says.


The program has had “tremendous support and feedback from the community,” while exposing new customers to Brand’s wines, says O’Sullivan, who declined to share sales figures but says the program has shipped Brand wine to 37 states and 70 different zip codes.

In March, Brand started offering “professional” virtual tastings, specifically targeting CEOs and executives, especially from the nearby tech industry in Silicon Valley.

O’Sullivan says the idea came after she heard customers from the business world complain that the new social-distancing guidelines were making it impossible to have in-person business meetings. Despite the advent of video meetings, customers said a missing element was a more relaxed setting where deals could be closed outside of the virtual boardroom.

“‘Going from the boardroom to the dining room is gone,'” O’Sullivan says she was told.

Bean and O’Sullivan work with the executive hosts to curate the events, with the host buying the wine for their guests while Brand packages a selection of bottles. Because the virtual events are curated and tailored to each customer, Bean and O’Sullivan say that pricing varies, but a virtual tasting for executives can start at $785 per attendee and that includes “an in-depth guided tasting and four bottles of wine for each attendee,” according to the winery.

While Bean and O’Sullivan won’t reveal the names of any participants, they say at least some of the participants are from Fortune 500 companies, and one company recently closed its largest deal ever during a tasting.

Lasting impact

While success in 2020 has meant simply treading water versus the type of annual growth Bean and O’Sullivan hoped for, the couple still feel that their new offerings will continue bringing in extra revenue into the future.

They’re already anticipating a boost from virtual holiday parties for some of the corporate customers Brand has picked up through its professional virtual tastings. And Bean and O’Sullivan hope that the new customers their products have reached will also return to their online shop to buy bottles of wine as gifts for the holidays as well as further down the road.

“We would love to be in a much better place than we’re at,” O’Sullivan says. “But, we haven’t lost ground and, I think, for us that was a huge thing.”

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