Trailblazer

One

Beginnings

The Benioffs of San Francisco

Here are two surprising personal tidbits about me: I graduated from college. Not only that, I majored in business.

Among my peers in the tech sector, those résumé points are something of a novelty. Countless Silicon Valley founders and CEOs proudly confess to quitting school to pursue their dreams. It’s no secret why the story of the “dropout billionaire” is so predominant. It’s the kind of compelling personal narrative that magazine editors and Hollywood screenwriters love. It also props up the old mythology that in America, a person’s success is largely a matter of sheer determination and will. A genuine hero is someone who learns about business by building one.

I’m a big believer in the enlightening, civilizing powers of higher education, full stop. But I’m not convinced that attending college makes you a superior entrepreneur. The courses I took at the University of Southern California made me a more well-­rounded and curious person, but the toughest business challenges I’ve faced, especially lately, are those that my professors in the 1980s simply couldn’t have anticipated.

There’s one way in which I do fit the profile of the archetypal tech entrepreneur, however. My first, most formative business classroom wasn’t a classroom at all.

It wasn’t my basement computer lab, or my first job, or the boardrooms where I made those early, tentative pitches to potential Salesforce investors. My classroom sat on four radial tires and ran on leaded gas. It was my father’s 1970 Buick station wagon.

The Benioff family Buick was a whale of an automobile nearly 19 feet long with simulated wood paneling. Driving around with my dad on hot summer afternoons, my bare legs stuck to the vinyl seats. Most of the time our trusty wagon was just a means of getting my parents, my two sisters, and me from point A to point B. Sundays were different, though. On Sundays it became a delivery vehicle.

My father, Russell, owned a chain of dress shops called Stuart’s Apparel. On weekends, he’d run a circuit around the San Francisco Bay Area transferring merchandise between his six locations, and he often brought me along to help. We’d park the Buick near the stockroom door, lower the tailgate, and march in and out with bolts of wool, linen, rayon, cotton, poplin, and polyester draped in our arms.

His shops were scattered all over the Bay Area, sometimes up to an hour’s drive from San Francisco; so our Sunday ritual often consumed the better part of a day. When I wasn’t staring out the window lost in my interior world, I passed the time thinking about how my father worked.

During the week, Dad would gather all the data on what items were selling and transfer the most popular merchandise to the best-­performing stores. I’d overhear him say things like “We need pink angora sweaters at Valley Fair” and off he’d dash, leaving his half-­eaten dinner behind. At one point in the 1970s, fox and rabbit coats took off, and for more evenings in a row than I could count, so did Dad. He’d get the call from one of his managers, hang his merchandise on a metal bar he’d installed in the Buick’s cargo space, and roar off.

It’s fair to say that my dad wasn’t bursting with personality. He was a giant at six foot seven, not unlike myself, but a decidedly gentle one: affable, down-­to-­earth, impeccably polite, and always caring, but like many men of his generation, emotionally restrained. Having lived through the Great Depression, he was frugal throughout his life. He shopped for clothes mostly on sale racks at big-­and-­tall stores, and every car he bought—­including the Buick—­was used.

Dad’s father, Fred Benioff, was one of three Benioff brothers who immigrated with their father to San Francisco from Kiev (then part of the Russian Empire) in the late nineteenth century to enter the fur trade. Beyond that, I know very little about Fred; he left his wife and kids when my dad was young and they never spoke again. Dad’s mother, Helen, eventually managed to wrestle away control of the Benioff fur business from her ex-­husband and ran it herself. The business had outlets all over the West, which forced her to work grueling hours, so my dad and his brother were raised with the help of family friends.

In 1966, the year I turned two, Dad decided to quit the family business to strike out on his own—­and before long he was not only the CEO of Stuart’s Apparel, but also the CFO, chief buyer, director of marketing, and head of sales. This meant that most nights, when he wasn’t traveling to Los Angeles or New York—­as he often did to scour their garment districts for new styles—­he sat at the kitchen table until eleven o’clock, doing the books by hand. Because he managed the inventory for all six stores himself, his weekends were mostly consumed by shuttling dresses and sportswear from one location to another. His only indulgences were playing dominoes and occasionally going fishing or hunting.

I never liked the idea of killing anything, but I spent many days as a boy with a 12-­gauge shotgun over my shoulder. Hunting ducks, doves, deer, and even wild pigs with my father in the orange groves of California’s San Joaquin Valley, and fishing in the Truckee River near Lake Tahoe, were as much a part of my childhood as hauling around women’s slacks and blouses. I didn’t particularly enjoy these activities—­or like them at all, really—­but these were the activities I could do with my dad.

Those Sundays in the car shuttling merchandise from store to store were long and tedious. But they did help me realize early on that I was not a fan of the retail business, one of several glaring differences between my father and me. Russell Benioff was an outdoorsman and a wizard with tools and lumber, but he wasn’t technically-­minded. I, on the other hand, was so fascinated by electronic equipment that, according to my mother, Joelle, I took the family telephone apart and put it back together at the age of four. Every time my maternal grandmother visited, I begged her to take me to Radio Shack.

As far back as I can remember, I was the shy kid who rarely had play dates, avoided group activities, and preferred the company of my golden retriever, Brandy, to that of just about any human being. My dad wasn’t the type to express concern over my social development, but my behavior worried my mother. She couldn’t get me to play baseball or even come out to say hello to her friends when they visited. I wasn’t particularly motivated by school, either: Once, when a kindergarten teacher asked me to draw a circle, I looked her straight in the eye and defiantly drew a line. Even though Mom left countless teacher meetings in tears, she continued to give me a long leash to pursue my passions, which certainly weren’t in the classroom.

When I was twelve, I packed up my second-­floor bedroom and moved down to the basement, where I could pursue my singular passion free of interruption. I bought my first computer, a TRS-­80 from Radio Shack, two years later and immediately withdrew from the analog world. After learning the basics of coding at fifteen, I wrote a simple program called “How to Juggle.” I sent it to a computer magazine and they paid me $75 for it. Suffice it to say that by that point, I was hooked.

On my sixteenth birthday, I traded my TRS-­80 in for an Atari 800 with a freestanding disc drive and a printer. That summer, I started working part time at ComputerLand and in my off hours founded my first company, which I christened with an outrageously sexy name: Basic Computers, after the BASIC programming language with which I had fallen in love.

I began writing reviews of computer games; when I noticed some games had software bugs, I wrote to the developers and offered to fix them for free. Soon I started programming games of my own. My first creation, Quest for Power, had a convoluted plot involving King Arthur and Sir Galahad and required players to vanquish a series of foes in pursuit of the Scroll of Truth.

This game, and many more that I created, helped me earn more than $5,000 in six months, which was a fortune for someone my age. I used the money to buy my first car, a black Toyota Supra, and vanity plates that read MRB 82. The money I earned from those games over the years eventually paid for college.

Looking back, I continue to marvel at the fact that my parents not only tolerated my eccentric behavior, but gave me enough independence to fully indulge it. When I tell people about how I was allowed to turn our basement into my own private residence at age twelve, they are always (justifiably) astonished. In retrospect, I imagine my mother was less than thrilled when I announced, on the very day I got my driver’s license, that I needed to make a business trip to a computer company in Mountain View, much farther than I had ever driven on my own. But she let me go. And that summer, when I asked if I could fly to England, alone, to research castles for my games, Mom gave me her blessing, so long as I stayed with friends of hers in Leeds and promised to call home every night.

My mother claims that she indulged me because she knew I was stubborn and wouldn’t take no for an answer. The truth, I know, is that she saw something in me that others didn’t and allowed me to pursue it, even if doing so made it nearly impossible for her to get a good night’s sleep. Neither she nor my father fully understood what I found so fascinating about computers, but they respected my drive, my strong will, and my unwavering commitment to things I cared about, and sensed that these values would serve me well when I got older. They turned out to be right.