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The Anti-Venture Capitalist

By Christopher Thiem


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oing into my first meeting with Jeff, I expected to meet a professional executive. A venture capitalist coming from a business meeting would probably be rather formal and have on a nice suit, or perhaps a navy blue blazer. But when Jeff arrived I was shocked. He drove up in his dented white Ford F-150 truck that runs on propane, allowing him to drive solo in the commuter lane. Not only was he not wearing a suit, he had on a Hawaiian shirt, a pair of plaid shorts, and Reef sandals. I would have guessed the man was headed for vacation, not a stress filled day at a venture capital firm. The truck, the clothes, the casual way he entered, were the first of many clues that Jeff Webber is not your average venture capitalist and that as an individual he has a rich and interesting story to tell.

While many people view

venture capitalism as a cutthroat industry where only the ruthless win, Jeff brings his own style to the job. Outwardly, Jeff appears to be a very humble and laid back man. He declares he is nothing like the venture capitalists seen on the show Shark Tank, and for the record, doesn’t think that Shark Tank is an accurate

Jeff Webber works at his own company, The Entrepeneur’s Fund. The top picture is the entrance to his companies office and the bottom picture is off a funny sign he has in his office.


representation of his business. Jeff enjoys his career and all the toys he has been able to purchase from his success, but remains grounded in reality. He attributes this to his middle class upbringing and the work ethic instilled in him by both his father and his mother. He believes people are his best asset, and this is evidence by his loyal employees, some of who have worked for him for over twenty years. As well, the majority of people he calls friends, he has known for years if not decades, one as far back as seventh grade.

Though currently running his own fast paced venture capital firm, helping fund hi-tech entrepreneurs and focusing on new business development, Jeff earned his undergraduate degree in American Studies at Yale University. While I found this inconsistency strange upon starting this project, after more

Jeff ’s office building is called the Atrium and is a compilation of many small business. His laid back attitude can be seen in this longboarding picture. research, I learned that frequently students major in fields quite different than their eventual career paths.

As a child, everyone thought

that Jeff would be a lawyer when he grew up. He too had aspirations of entering law and


so selected a liberal arts undergraduate degree. However, on a family vacation to New Zealand he spent time contemplating a career in law and how that would match with his interests. He enjoyed working alongside his father at the family business concentrating on finding ways to improve the operations. Realizing he wanted to work in business, he decided that he didn’t want to become a lawyer.

After graduating from Yale,

Jeff ’s first job was at an investment firm where he quickly figured out that working for a large company wasn’t his career path either. He was accepted to the MBA program at Stanford, yet shortly after the first semester started, he dropped out and was, for the third time, without

a direction until he landed at a business management consulting firm. After a few years of working at the firm, Jeff branched out on his own. The excitement of building a company from the ground up challenged him intellectually and fulfilled his creative side, eventually leading him into the world of venture capitalism.

When I first drove into the

parking lot of Jeff ’s office building, I was amazed at it’s size. When I was discussing the interview with him, Jeff told me he ran a small business, yet the building was at least eight floors tall. He had given me his office number, which was on the second floor, and as I walked up I realized this building was just a compilation of small businesses. His entire company is located

behind one door on the second floor. It is comprised of a reception area, a conference room, an open area work space, four offices, and a small kitchen. Jeff ’s office is large and filled with an odd assortment of business and personal keepsakes, random computer parts lying on the desk, stacks of papers on the couch and in the corner a fishing poll. It is clear he is “old school” preferring pen and paper over a computer, as there is no computer on his desk.. He uses his laptop to read email.

Jeff describes himself as the

“anti-venture capitalist”, and in many ways it’s an accurate description. While he does have the materialist possessions due a successful venture capitalist, the vintage cars, vacation homes,


and a staff of employees that keep his personal life in order, he doesn’t flaunt his success. His main house in Healdsburg is secluded from view and visited by only the closest of friends. Located on country road just outside the town, the “ranch” as he calls it, has a mile long driveway bordered by rolling vineyards. While he is no longer a partner and part owner of Longboard Vineyards, he continues to sell his grapes to Longboard, which produces award winning wines. Two private, key-coded gates and a steep incline prohibit “solicitations from random Jehovah’s witnesses and vacuum cleaning salespeople” according to Jeff. It seems his house is a peaceful place for him to unwind and enjoy the quiet, until you meet his four chocolate labs. While professionally trained for duck hunting, these furry guys are sure friendly and love to follow you all throughout the property. His vintage cars, while kept in good shape, almost never leave the garage, as his Ford Explorer and F-150 are his prefered means of travel. It’s here at the ranch or at the duck club where he spends the majority of his free time.

duck marsh is his favorite of all his vacation homes. During the summers, he spends weeks with his children and family friends on his houseboat on Lake Shasta. It’s not a luxurious houseboat. In fact it’s the boat he has owned for over thirty years, and while he certainly has the funds to buy a new one, he continues vacationing on this boat for sentimental reasons.

with the impression that Jeff was a “jerk”, but perhaps would make for an interesting boss. Steve later figured out that this first interview routine was Jeff ’s way of testing whether a potential candidate had the sense of humor and guts to tough it out in his company. They became great friends inside and outside of the workplace. Throughout my entire time with Steve he was constantly laughing, wondering eff ’s rather odd personally not what Jeff ’s reaction would be to only struck me on our first meet- this interview. ing, it also struck Steve Plume, one of Jeff ’s business partners n speaking with Jeff about his for over twenty-five years, on journey from those early college their first meeting. After gradudays at Yale to running his own ating from Yale and working at firm, I asked him what was the random business jobs, Steve had most important advice he could moved to the Bay Area to pursue give me and what he thought his a career in the hi-tech venture greatest achievement to date has capital business. He was quickly been. “Business is all about relacontacted by Jeff who was looktionships” he said. “The phrase, ing to hire Yale graduates. Jeff it’s not what you know, it’s who suggested a time for the two of you know, is the key to success’’. them to meet. After a long day With an American Studies unof unscheduled interviews with dergraduate major from Yale, Jeff several members of Jeff ’s comhad no educational foundation pany, he finally had his meeting for his future career, but what he with “the big boss.” As Steve tells did have was intelligent friends. the story, Jeff started the interBy keeping in touch with them view by intensely studying his and building those relationships, resume, glancing at him from he was able to draw upon all of time to time, then back to intheir education and experiencorn and raised in rural oretensely studying the resume. This es to assist him in building his company. And those relationgon, Jeff ’s hobbies don’t conform continued for what seemed like to what I thought would interest an eternity. Finally, Jeff opened ships he told me, helped him a high powered entrepreneur. He the conversation with, “Why accomplish his greatest achieveshould I hire someone who’s spends from October to Janument; the creation of over 10,000 ary duck hunting at a private done squishy shit all their life?”. jobs for people in companies his duck club, where he has been Steve recalls that he was instant- venture capital firm has funded a part-owner for over twenty ly taken aback by the comment over the years. years. His cabin overlooking the and at the end of the day he left

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