Bart and Barb O'Brien in the Cabernet Sauvignon Vineyard
Barb and Bart got married the year after they met, had 2 children (Emily and Mason), and Bart pursued a career starting various companies..
He told Barb he was an entrepreneur when they met. Her response was "I am going to have to marry you because all my sisters are married to Irish entrepreneurs".
Barb had signed up for quite an adventure. They bought a house together in Piedmont when she became pregnant with Emily, then the house was sold after Emily was born to finance a temporary Halloween theme park venture called Scaregrounds.
After Scaregrounds failed, Bart went back to high tech and joined Bill Paseman to found Calico Commerce, a software company to configure complex products such as computers for the new sales channel called the internet.
After seven long years of living in rental property that was constantly being sold from underneath them, Bart's first software startup, RSA Data Security, was acquired by Security Dynamics for $250 million. Bart had sold most of the stock to finance their wedding, honeymoon, and the purchase of their first house, but fortunately just enough stock was left to purchase their second house in Los Altos Hills in 1997.
Then Calico Commerce went public in 1999 at a valuation of $1.8 billion (based on closing price day of IPO).
Bart only sold a small portion of his stock before the high tech crash of 2000 and subsequent failure of Calico, but this was enough for a down payment to purchase the Costello Vineyard to make Barb's "dream of owning land in Napa Valley" come true.
On the property are 33 acres of vineyards, a bonded winery, and their home. When you visit, you will be treated to an intimate experience in their backyard sitting at picnic tables under oak trees.
Make sure you see the Romantic Portfolio and Romantic Trio wine gift sets. Perfect for unique wedding gifts, they tell a wonderful story of romance through wine.
Bart and Barb live on the estate with their two children, Emily (21) who is attending Napa College, their son Mason (19) who is attending Cal Poly San Luis Obispo, and their five cats Motor, Hobbes, Chicharrón, Malcolm XX, and Gemini. Sasha, our Hungarian Viszhla, who many people met at the winery, recently passed away at the age of 12 from cancer.
Sasha, who modeled for the Wine Dogs of Napa Valley book, was the only professional model in the O'Brien family even though everyone agreed she looked like a dog.