From CEO of Asset Management Firm To Ranch Owner

When Derek Webb, CEO of Webb Asset Management, lost almost everything in the stock market crash of 2008, he decided to take his life and career in a completely different direction and begin renovating and restoring historic event venues in Northern California. He acquired Spring Ranch in Mendocino in 2000 and Triple S Ranch in Napa Valley in 2011.

Starting completely over in a new industry was a blessing for me,” Webb says, “I came into it without any biases or preconceived notions. It forced me to be creative and resourceful.

Spring Ranch has been open since 2010 and Triple S opened in 2015. Both properties, which were essentially in ruins at the time of purchase, sell out almost every weekend for private events such as corporate retreats and weddings since they’ve been under Webb’s stewardship. He devoted himself to restoring them to their former glory – and then some – sourcing period appropriate architectural salvage and antiques from around the world, including a Victorian barn that he shipped piece by piece from Canada to add to Spring Ranch’s grounds.

Triple S Ranch is Like Summer Camp for Grown Ups

Triple S Ranch, just outside Calistoga in Napa Valley, had a long history as a working ranch, restaurant, and family resort before falling into disrepair. Since Webb re-opened it in 2015, companies including Cloudera, Modsy, Just Give, Capital Advisors, Waggl, Shramsberg Vineyards and Chateau Montelena Winery, as well as hundreds of wedding parties, have held events at the ranch. The property is on 20-acres filled with old growth trees and orchards, including a 175-year-old walnut tree that has long been a traditional spot for locals to marry. The property has a perfectly preserved modernized Victorian house, plus 14 cottages, allowing 50 to sleep onsite. There are more than 10,000 square feet of entertaining space, including a former dairy barn that has been converted into a 2,400 square foot event space, as well as multiple patios and redwood decks. The addition of a pool, gym, and 25-person infinity hot tub make the ranch, which requires a full buyout, an experience akin to an idealized summer camp for adults. Clients bring in their own vendors, which can keep costs very low compared to similar event venues.

Spring Ranch is Ideal for an Intimate Wedding

Spring Ranch is located on the 350-acre oceanfront Spring Ranch Agricultural Preserve on the Mendocino Coast, about three hours north of San Francisco. It is one of the oldest complete coastal ranches in California, anchored by a renovated 5,500 square foot Carpenter Gothic Victorian mansion where 21 people can sleep. An ocean view suite that sleeps two has been added on top of the original Carriage Barn. The 1840s barn that was imported from Canada has room for 120 to dine and an outdoor patio that accommodates 200 guests. As with Triple S Ranch, clients provide their own vendors.

“After 30 years of working in finance, I was fortunate enough to figure out what was important to me,” Webb says. “Reinventing these properties that have been at the center of communities since the 19th century and transporting people back to those times in comfort and luxury – these things give me the ultimate satisfaction.”

Triple S Almost Lost to Wine Country Fires

When the fires tore through Napa last fall, Webb, his employees and a few neighbors fought alongside one another to save Triple S Ranch. After a grueling nine hours of effort, the ranch was still standing. Two other historic resorts down the road were lost in the fires, while Triple S Ranch was lucky enough to defy the odds and survive – much like its owner.

Derek would be happy to chat with you further about how he transformed both of his ranches into what he calls mini-Shangri-Las, and found his true calling along the way.

For more information on Triple S Ranch and Spring Ranch, please visit and