Welcome to Disengaging.

For some business-owning families, there may be conflict that cannot be resolved within the current ownership structure and dynamic. There might be irreconcilable differences in their Shared Purpose or Vision for the future, estate planning that has pitted family members against one another, or some other deep-seated dispute or friction that keeps them from being able to engage as owners. To delve into these situations, More at Stake introduces the concept of Disengaging.

Because in family enterprises there is more at stake than money, and because many enterprise-owning families see their business as a fundamental part of their family’s legacy, there can be a sense of failure or shame associated with a sale, siloing, or splitting-up of the business. But, while these feelings are understandable, there is no shame in accepting that a once-strong Shared Purpose is torn, or that family branches have fundamentally different views of the future.

There is no shame in adapting to changed circumstances with due care and thoughtful planning.

Disengaging—changing your relationship with the business, for yourself and your family—can be a positive step, and one that allows your family and the business to move forward.

But, dry facts and abstract advice about family business conflict can’t tell the whole story of what’s going on. For a more in-depth look, More at Stake offers Disengaging, our series sharing the story of the Cannon family, who find themselves facing disconcertingly bitter and seemingly permanent conflicts about the future of their businesses and their family.

Latest Installments from the Cannons

Disengaging 8 | Rained On

  Grace Portman Lear Wednesday afternoon Matthew and I had our quarterly meeting of the Cannon Springs divisions this afternoon. My mom, Joyce, who is the President of the company, made me head of the Clear Lake vineyard in 2002 after my grandfather, Pete Sr.,...

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Disengaging 7 | The Mortgage

In “The Mortgage,” Peter Cannon is confronted by challenges that come with owning multiple operating businesses—especially if one business provided the seed capital to establish another. How will the Cannons deal with the financial unbalance between their two businesses? What causes the unbalance in the first place? Read "The Mortgage" to find out more. read more

Disengaging 6 | Triangles

The Cannon Springs Farm office at Potter Valley, 3:00 pm Matthew Portman: Mom, when you have a moment I’d like to talk with you about how we’re going to deal with next year’s Muscat crop. I think that we should market it more widely—maybe even out of state. There may...

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Meet the Cannons

The Cannon Family

Meet the Cannon family. Sixty-seven-year-old Joyce Cannon succeeded her powerful and difficult father, Pete Cannon Sr., as the CEO of Cannon Springs Farm, a multigenerational grape-growing business in Northern California. Her brother, Peter Cannon, is CEO of Cannon Bridge Winery, which he and their father founded in 1986.

Fifteen years after Pete Sr.’s death, Cannon Bridge Winery is finally becoming successful, while Cannon Springs Farm faces a growing number of business challenges. Joyce is deeply at odds with her brother over how to best handle the businesses, and with many of their children involved in and working for the businesses, Joyce and Peter find themselves in grave conflict.

Over the coming months, More at Stake subscribers will meet the Cannons and their companies; learn about the business planning, ownership transfers, and estate planning that seeded their conflict decades ago; and watch as they navigate this difficult path.

Should they remain in business together? Or, for the sake of their family relationships, is it time for them to disengage? For the continuing story of the Cannon family, More at Stake will post bi-weekly episodes to our Disengaging column.

Pete Cannon

Pete Cannon

Pete Cannon was born in 1919, the son of successful Californian wheat growers along the western edge of the Sacramento Valley. Together with his wife, Florence, he had two children, Joyce and Peter.

In 1954, Pete founded Cannon Springs Farm on the slopes overlooking Clear Lake, in Lake County, to supply wine grapes to the budding winemaking industry of California. Cannon Springs Farm built an excellent reputation among the mid-market winemakers of the region, and in 1966, Pete was able to establish a second location, in neighboring Mendocino County, in Potter Valley. In 1986, Pete and Peter founded Cannon Bridge Winery in the Mendocino Ridge, with a goal of producing fine varietals. On his 70th birthday, Pete stepped down as President of Cannon Springs Farm and Cannon Bridge Winery, passing leadership on to Joyce and Peter, respectively.

Upon his death in 2002, Pete passed 30% ownership of Cannon Springs Farm to Joyce and Peter each. He gave their biological children the remaining 40%, per stirpes—5% to each of Joyce’s four children, and 20% to Peter’s son, Jacob. Peter received 80% ownership of Cannon Bridge Winery, and Joyce received 20%.

Pete was a tough, opinionated, but loving man, and his fabled intensity was known far and wide.

Joyce Cannon Portman

Joyce Cannon Portman

Joyce Cannon Portman was born in 1949 to Pete and Florence Cannon. She married Tom Portman, an ER doctor, in 1969, and together they have four children—Grace, Matthew, Sara, and Henry.

Joyce grew up alongside Cannon Springs Farm and joined the business as an employee straight out of college. She quickly showed her value as a manager familiar with every facet of grape growing at Cannon Springs Farm, and became VP of the Clear Lake division in 1980. After helping guide CSF to new heights in the 80’s, Joyce became President of the company when her father stepped aside in 1989.

A divide has been growing between Joyce and her brother, Peter, for some time, as the interests of Cannon Springs Farm and Cannon Bridge Winery have diverged. The terms of Pete’s will only served to broaden the chasm: Joyce was left 30% and 20% ownership of CSF and CBW, respectively, compared to Peter’s 30% and 80% shares of ownership. Additionally, her children were each left 5% ownership of CSF, compared to Jacob’s 20%. Joyce feels that her side of the family has put in more work and received less return.

Grace Lear

Grace Lear

Grace Lear was born in 1971, the first child of Joyce and Tom Portman. Just like her mother, Grace has always had a deep connection with Cannon Springs Farm, and, just like her mother, Grace joined the family business straight out of college.

She became VP of CSF Clear Lake in 2002, following the death of her grandfather, Pete, and has run the division superbly despite growing competition and a shifting market. She has a particular talent for nurturing CSF Clear Lake’s growing stock, and is fondly referred to as ‘the vine whisperer’. Grace has been at odds with her Uncle Peter and cousin, Jacob, for some time over the diverging interests of Cannon Springs Farm and Cannon Bridge Winery, and was none too pleased by the terms of her grandfather’s will.

Grace is married to Oliver Lear, and they have three children—Lucy, Elliot, and Sam. She is a 5% shareholder of Cannon Springs Farm.

Jacob Cannon

Jacob Cannon

Jacob Cannon was born in 1991, to Sophia and Peter Cannon. He grew up around Cannon Bridge Winery until Sophia and Peter divorced in 1995, and Jacob moved with his mother to the East Coast. Despite the distance, Jacob and his father remained close, and he came to live with his father for a month each summer, and visited for a week each Christmas.

After graduating high school in 2009, Jacob moved to California. He bounced around several jobs until landing in UC Davis’ Viticulture and Oenology Program for winemaking. After graduating, Jacob joined the Cannon Bridge Winery team full-time, as an Assistant Vintner to Dominic Vargas, Cannon Bridge’s Head Vintner.

Like his father, Jacob has an incredibly creative mind, and he constantly tinkers with the winemaking processes and techniques. This tinkering, paired with his brash attitude and penchant for going against the grain, has made Jacob’s presence in California a source of joy, as well as disturbance, for the family.

Upon Pete Sr.’s death in 2002, Jacob inherited 20% ownership of Cannon Springs Farm.

Mia Cannon

Mia Cannon

Mia Cannon was born in 1997 to David and Chi-Yu Lee. Her father died shortly after the birth of her brother, Jay, in 1999, and Mia and Jay lived with their mother. After Chi-Yu married Peter Cannon in 2001, Peter adopted Mia and Jay.

Mia is a shy and inquisitive girl, hoping to study biology in college. She is currently spending a gap year working for her cousin, Grace, at Cannon Springs Farm – Clear Lake.

Florence Cannon

Florence Cannon

Florence Cannon was born in 1918, the only child of Clarence and Emma Stratford. Her father was a military man who established a successful Midwestern farm equipment manufacturing business after his service, and Florence met her husband, Pete Cannon Sr., when she accompanied her father to California on a business trip. Florence and Pete hit it off immediately and married in 1947. Together they had two children, Joyce and Peter.

In 1954, Florence and Pete founded Cannon Springs Farm, Inc. in Lake County, California. When they expanded to a second location in 1966, the expansion was funded largely by the inheritance left to Florence by her parents.

Florence Cannon passed away in September of 1992. She had always provided the “glue” of the Cannon family, and her mixture of compassion, community spirit, and meticulous attention to detail will leave her mark on the generations to come.

Peter Cannon

Peter Cannon

Peter Cannon, named for his father, was born in 1956. He grew up running the rows of their family’s grape-growing business and swimming the beautiful waters of Clear Lake, alongside his older sister, Joyce.

Peter married his first wife, Sophia, in 1989 and they had their only son, Jacob, in 1991. They divorced in 1995 and Jacob went to live with his mother on the East Coast, only occasionally seeing his father.

Peter married Chi-Yu Lee in 2001 and adopted her two children, Mia and Jay, the same year. In 1986, Pete Sr. and Peter established Cannon Bridge Winery, among the misty coastal peaks of Mendocino Ridge. Three years later, Peter became President and CEO of Cannon Bridge Winery when his father stepped aside on his 70th birthday. Peter has led CBW with the mission of producing extraordinary varietals, and the hard work paid off in 2007 when CBW won its first major awards. Since then, the business has been propelled forward, and is a highly-regarded throughout the U.S.

Peter is a deeply technical mind, always brain-storming new ways to improve his growing and vintification processes and, at times, loses the human narrative going on around him. He is completely dedicated to building Cannon Bridge Winery, and some of the business decisions he has made to that purpose have deepened the rift that exists between himself and Joyce’s side of the family.

He remains a 30% share owner of Cannon Springs Farm, and holds 80% ownership of Cannon Bridge Winery

Matthew Portman

Matthew Portman

Matthew Portman was born in 1973, the second child of Tom and Joyce Portman. He received his MBA in Finance, and spent 15 years after graduate school working at a private equity fund in San Francisco. There, he met his wife, Reya, and together they have two children, Pam and Zach.

Matthew’s skills in finance led him back to Cannon Springs Farm as VP of the Potter Valley division in 2013. He brings an openness toward modernization and diversification at Cannon Springs Farm—at times, to the chagrin of his mother and sister, Grace. Matthew’s tenure as VP of CSF Potter Valley has been fraught with hurdles, many of which have been beyond his control, and—like his mother and siblings—Matthew has struggled with his Uncle Peter’s decisions to put Cannon Bridge Winery before Cannon Springs Farm.

Matthew is a 5% shareholder of Cannon Springs Farm.

Chi Yu Cannon

Chi Yu Cannon

Chi-Yu Cannon was born in 1970 in the suburbs of San Francisco. Her parents were first-generation Chinese immigrants who fled conflict in that country. Chi-Yu grew up happily, reading the great American novelists of the 20th century, and became a writer herself after college.

Chi-Yu married her first husband, David Lee, in 1995, and together they had two children, Mia and Jay. David died from a heart attack in 1999, shortly after Jay was born. Peter Cannon, who had always admired Chi-Yu’s work, met Chi-Yu at one of her book signings in 2000. They began dating, and married in 2001. Peter adopted Mia and Jay later that year, and has been an excellent father to them.

Chi-Yu is kind, perceptive, and funny, and a loving mother to her children and her stepson, Jacob. She has made great efforts to support Jacob in his projects and pursuits, and they share a good relationship.

Jay Cannon

Jay Cannon

Jay Cannon was born in 1999 to David and Chi-Yu Lee. His father died shortly after his birth. Jay was adopted by Peter Cannon after Peter married Chi-Yu in 2001.

Jay is an active high school senior, and is a member of his school’s varsity soccer and cross country teams. He is considering following a path similar to his sister’s—taking a gap year between high school and college, to work at Cannon Springs Farm.

Cannon Family Timeline


Pete Cannon Sr. founds Cannon Springs Farm (CSF) at Clear Lake, in Lake County, CA.



CSF expands to a second location at Potter Valley, in Mendocino County, CA.


Cannon Bridge Winery is founded by Pete Cannon Sr. and Peter Cannon in the Mendocino Ridge AVA.


Pete Sr. retires. Joyce Cannon Portman becomes President and CEO of CSF, and Peter becomes President and CEO of CBW.



CBW has its first full harvest, and reduces the number of grapes it sources from CSF.


CBW expands its cultivated acreage.


Pete Sr. dies, leaving 60% ownership of CSF split evenly between his two children, and the remaining 40% among his biological grandchildren, per stirpes. Ownership of CBW is split between Peter and Joyce 80%-20%, respectively. Grace Lear takes over as VP of CSF Clear Lake.


Cannon Bridge Winery wins its first major award—for its 2005 Syrah—propelling the business to a new level of success.


Matthew takes over as VP of CSF Potter Valley. Jacob joins his father at CBW.


The Potter Valley Riesling blocks are hit unexpectedly by an outbreak of crown gall. They will take several years to recover fully.


Cannon Bridge Winery stops buying grapes from Cannon Springs Farm entirely.