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The Harder You Work, the Luckier You Get

An Entrepreneur's Memoir

About The Book

Joe Ricketts, founder of TD Ameritrade, shares the epic inside story of how a working-class kid from the Nebraska prairie took on Wall Street’s clubby brokerage business, busted it open, and walked away a billionaire.

Joe Ricketts always had the gift of seeing what others missed. The son of a house builder, he started life as a part-time janitor, but by the age of thirty-three he saw the chance to challenge the big brokerage firms by offering Americans an inexpensive way to take control of their own stock trading. Nowadays, we take for granted that Main Street is playing right there on Wall Street, but Ricketts made that happen. His company, begun with $12,500 borrowed from friends and family, took off like a rocket thanks to an early embrace of digital technology and irreverent marketing. But Ameritrade also faced a series of near-disasters: the SEC almost shut him down; his partners tried to force him out because of his relentless risk-taking; penny brokers swindled the company; the crash of 1989 nearly cost him everything; and he was almost shut down again when a customer committed massive fraud. By the time of the dot-com bust, he had proven that his strategy based on frontier values could survive just about anything.

The Harder You Work, The Luckier You Get offers a view inside Joe Ricketts’ mind, giving readers a visceral understanding of how entrepreneurs think and act differently from the rest of us—how they see the horizon where we just see a spreadsheet. As unvarnished as the prairie he comes from, Ricketts also talks honestly about his shortcomings as a manager, the career sacrifices his wife made for his business, the complexity of being a father, and the pain of splitting with his mentor and of his brother’s death from AIDS. Overcoming these and other challenges, he built a company now worth $30 billion.

A must-read for anyone who’s ever dreamed of starting their own business, The Harder You Work, The Luckier You Get is the ultimate only-in-America story.


Chapter 1 CHAPTER 1
I remember that day vividly, the smell of wood, the sound of hammers banging, the sawdust scattered on the ground. My father had brought me to a construction site where he and his men were building a new home. I was still a boy, and this was in Nebraska City, where I grew up, a town of a little over seven thousand. The decade was the 1940s, but from the way the men were putting up that house—without electrical power, using only their hand tools and the strength of their muscles—it could have been much longer ago.

Each carpenter wore an apron around his waist, with pockets for the different-size nails he used for different tasks. He would pull out a nail with his left hand, hold it in the spot where it needed to go, and bang, bang, bang it in with the hammer in his right. Construction then was altogether different from the way buildings go up now. Nothing was prefabricated and shipped to them, like the trusses of today. The men had to put up every piece of the building one at a time.

My father had brought my younger brothers and me to the job site and told us to keep out of the way and to pick up trash. When the men finished sawing a board to size and the scrap end fell on the ground, I would pick it up and throw it out. Other than that, I watched. The work was hard and hot. The men got so wet with perspiration that the sawdust stuck to their clothing and their skin. Sometimes they talked with one another about the tasks they were doing, sometimes they joked, but mostly they sawed and hammered without speaking. I remember them as happy—working together, getting something done.

Now here is a mystery. That boy who was brought along to clean up the wood scraps, who grew up in a working-class town with a frontier mentality, would go on to found one of the most disruptive businesses of finance’s computer age. That business would utilize the latest communications and digital technologies to revolutionize and democratize the clubby, old, highly regulated, East Coast–based financial industry—and in the process, the founder of that business would become a billionaire.

I was that boy, but if you had asked me then to share my daydreams and talents, they would have revealed no knowledge of computers or special gift for mathematics, and no visions of vast wealth. My idea of financial success back then went no further than the well-off men of our town—the owner of the drugstore or grocery store, our local dentist and doctor. I had no expectation that I would ever work in the finance industry, let alone help remake its services industry. And in fact, if you had asked my wife, Marlene, who met me in school, she would have told you that I seemed like the other young men. Maybe a bit more of a dreamer, imagining myself in charge of the businesses where I cleaned or clerked, but basically like the others, the sort who grows up to work hard all week to support his family, then goes out on Friday night and feels happy to talk with his friends and drink his fill of beer.

But on the day I’m thinking of, there was something new. My father’s construction company had been able to buy a new tool called a buzz saw. I watched the men lay a board across the sawhorses they used to hold it still, put a mark on it, and then switch on the new electric circular saw. It really did buzz. And that was it—in a moment, the board was cut to the length they needed.

The men were ecstatic. Dad, though, was calm, quiet. The Rickettses were stoic people. He worked seven days a week, either on the job site or keeping the books. Most days I saw him only at dinner, where it was my mother who would tell us kids if we’d done something well, and my father who would let us know what we had done wrong. He was the disciplinarian. I don’t believe he ever hugged me, and I knew better than to hug him. You never expressed your emotion in that way, or by saying “I love you.” But on that day, I could tell by his body language that he was happy. His shoulders were relaxed, and his movements were easy, jovial. “This is so wonderful, Joe,” he said. “It will allow us to get so much done so fast.”

That was what he wanted me to understand: the effect this tool could have on their work and their lives. In that sense, he had an innovator’s eye, not because he had invented the buzz saw but because he saw the possible benefit in it. I did not need to know the concept of productivity or the term early adopter. I could hear the meaning in my father’s voice and see it in the men’s smiling, sawdust-covered faces.

When I founded my own business, I would push hard, often against intense resistance, for my company to make advances like that one. Part of our success came from new communications and computer technologies that didn’t seem valuable to others back then, and that sound almost like a horse and buggy today—we were innovating with toll-free long-distance phone calls, touch-tone phones, data storage on cardboard punch cards, early personal computers and slow, primitive email. In discount brokerage, as on my father’s construction sites, success came down to how fast you could execute without a loss of quality, so we were always looking for a faster, better way.

Yet I did not grow up to become a midwestern Steve Jobs, some tech geek in a barn. It was never my interest to understand how the machines worked. I had no special enthusiasm for technology. In fact, I had very little exposure to new technology at all. We were one of the last families in Nebraska City to own innovations like air-conditioning or television, because my parents did not count those things among life’s necessities. But maybe because we didn’t have the new machines, I could see better what they could do and what a difference they could make in our lives.

Perhaps it’s surprising that a little boy who was tasked only with keeping the job site clean and staying out of trouble would have been so affected by the new tool the men were trying out or would remember its effects so well. I think there are two reasons I paid such close attention, and they both go back to my parents and my upbringing.

First, I had seen how very hard my father worked, the double pressure he was always under, to keep revenue coming in while sustaining his reputation for quality. I remember once we heard that a tornado had hit a farmhouse and destroyed it. The people whose home was destroyed belonged to our church. We kids were excited because building a farmhouse meant that Dad would take us out to the farm where we could do things we thought were special, like riding horses, though the farm kids had horses around every day and seemed to think they were boring.

One day, as the house was going up, my paternal grandfather came out to look over the work. He was old by then, done with physical labor but still healthy and active in the business. He bid the jobs before the men took them on, and he would come out and review their progress. The carpenters had spent all of that day building a stairway, and when they got to the bottom, they discovered that their measurements were off by a quarter of an inch. Now they had a choice: Did they put a shim under the bottom to fill the gap, along the floor where no one was likely to see it, or did they tear it out and rebuild the whole thing?

My grandfather was the boss of the business right up until he died. A tall, broad-shouldered man with a big waist, his authority was almost military. When he came to inspect that day, Dad was visibly nervous. The men worked for wages, so if they had to build the stairs again, that would cost my grandfather an extra day’s pay. But at the same time, it was the Ricketts reputation that brought in business. A lot of the houses in town had been built by my father and grandfather, and sometimes when they were up for sale you would see a sign on the property: RICKETTS BUILT. That reputation was their method of marketing—if they built well or badly, the whole community was going to hear about it.

When my grandfather saw that the stairway was off a quarter inch, he knew his reputation was at stake. He didn’t want to take that risk. He looked the staircase over, mused for a minute while the men held their breath, and said, “Build it over.”

The second reason I was so affected by that buzz saw was the context I brought to it, based on what I saw and heard at home, where my mother’s parents lived with us. Even as a child, I could feel they were broken people. My maternal grandfather had suffered what adults called a nervous breakdown, and he lived mostly in his own world, out of touch with reality. I never knew him as a healthy man. My grandmother had diabetes back before doctors knew how to treat it, and both her legs had been amputated clear up to the hips. She needed assistance to get in and out of her wheelchair. Although my cousin Mary Ann Weidemann remembers my grandmother affectionately, to me she seemed depressed and mentally absent. They lived until I was in my teens, and the explanation for all this waste and sadness came from my mother.

My mother didn’t tell their story all at once. There were many different parts and versions, and they would come out while she was cleaning the house or painting, home all day with us kids and thirsty for someone to talk to. I can picture her with her sleeves rolled and her hair tied up in a scarf—she reminded me of the wartime poster of Rosie the Riveter, with the slogan “We Can Do It!” Like my father, she was a person resigned to adversity, but she could not talk about her family history without emotion.

My paternal great-great-grandfather, she said, had been born in Germany, but he wanted to come to the United States. He wanted to leave before he was drafted into the Prussian army. His father had died young, though, so the only way he could leave was with his mother’s permission, which she wouldn’t give. Before he turned seventeen, that young man decided he had to leave his country and stow away on a ship because he lacked her approval.

His mother fixed him his Sunday meal every week. The following Sunday, when he didn’t show up for dinner, she took his meal, a waffle, and put the plate on the mantel to wait for him. It stayed there until she died. She was heartbroken. He made it past the Prussian authorities and ultimately immigrated to the United States. I think he became a blacksmith.

In the next generation, my great-grandmother was ambitious and married a banker. This was before federal regulation of banking, so a local banker was like the owner of any small business: He made his own decisions and lived with the consequences. That meant that our family had access to capital. They had seven children and wanted a farm for each. My grandfather was the oldest child, so they bought the first farm for him, taking on a lot of debt. The crops were good, the farm made money, and as soon as they had some equity in it, they borrowed against that and bought another. In time, they owned farms from South Dakota down through Kansas. You could say that for their time and place, my immigrant forebears were very successful entrepreneurs.

My great-grandfather died knowing he had succeeded. My mother grew up on the first of those seven farms. She lived in Manley, Nebraska, in a family that was not only one of the most successful farm families but also one of the prominent families of the community. They were Catholic, and in those days in their church the people who gave the most money got the first pew, and the second biggest donors got the next pew, and so on. My grandfather’s family had the first pew in the church. They bought a new car every few years. Their house was big for its time, with a pillar on each side of the front door, as compared to my father’s family home, which was at that time a log cabin. They covered it with siding, so it looked like a regular house. But it was still a log cabin. Growing up in the 1920s, my mother’s family was not wealthy, but they lived well as proud and prominent members of the community.

One day my grandfather bought a new bull, a major purchase for a cattle farmer, and the family threw a big party. The kitchen tables were brought out into the yard and laden with all kinds of food. There was a lot of competition among the farmers over who could produce the most from an acre of land, display the best animals, grow their crops in the straightest lines, and other tests of agricultural achievement. People were invited to come to this party to admire the new prize bull. It was like their own private county fair. There were games—my aunt used to tell me how guests would place bets on the number of eggs they could balance on a bull’s back before the eggs started falling off—and other kinds of fun that we don’t think about anymore.

Sometime after the party, it was discovered that the new bull was diseased. It might have had tuberculosis or hoof-and-mouth, a deadly infection that could spread through a community and ruin all the farmers around. This was before science understood the transmission of the disease, so to make sure it would not pass beyond my grandfather’s farm, his entire herd had to be destroyed. Once the vet made his diagnosis, my grandfather had no more say in the matter. The state sent men to dig an enormous hole, drive the animals in, slaughter them all, and fill the hole with dirt.

Because his entire herd had been destroyed, my grandfather did not have enough income to make the payment on his farm loan, and over time, as he missed more payments, the extended family defaulted on all the loans that had supported the family’s farms. By now, the Depression had begun. This was before welfare or social security was established, and so my grandparents became paupers. They lost it all.

My grandfather heard that there were jobs at the packinghouse in Nebraska City, so he moved his family there. They left without any assets, and when they arrived, they rented the cheapest home they could find, one with dirt floors. My aunt was so embarrassed to have her boyfriend see where she lived that when he picked her up, she asked him to meet her at the corner.

My grandfather’s plan was to get a factory job because that was the work available to a man with no skills except farming. The packinghouse was tough, dirty work. Today those places are as clean as hospitals, but back then there were blood and guts and feces lying all over.

He tried, but he couldn’t bring himself to go to work in the packinghouse like a boy. His life’s goal had been to become a big cattleman, and before he’d lost his farm, he’d had a big sign on the side of his barn with his name and the phrase “and sons.” That cattle herd had been the worldly representation of all his success and his legacy. Losing it destroyed him. He suffered a breakdown and never worked again. When I knew him, he spent the day in his rocker, looking out the window.

His sons went to work in those packinghouses to support the family, and his daughters got jobs in town. My mother was fortunate that she had an aunt who sponsored her to complete high school in Omaha. Her aunt found her a family to live with in exchange for housecleaning and babysitting along the way to earning her diploma. She learned to live as a city girl. After she graduated, she took a job at a five-and-dime store called Hested’s, where she would eventually meet my father’s sister and, through her, my father.

From then on, my mother was very, very conscious of the social standing her family had lost, and she was bound and determined to get back to where they had been. When she left the house, she was always dressed properly—no one but us kids ever saw her dressed for housecleaning. In church, we all had to be neat and clean, my younger brothers and me in our sport coats and freshly ironed shirts. The Latin Mass lasted an hour and I couldn’t understand a word of it, but I knew when to give the proper responses and understood that this was my mother’s social show-off time. There was no choice about being there. It was always very important to her that we put on our best show. I remember when I first started going to school, I came home from kindergarten and she received a phone call from a neighbor who had seen me walking across the street kitty-corner. “People are watching you and they know who you are,” she told me. “You’ve got to act right!”

I understood when she told me how her family had lost their farms that she was again teaching me a lesson in how to act right. If you wanted what she called a nice life, you had to make it yourself. You had to work hard every day, and when you got what you were after, you had to keep working hard because you could lose it all. And so, I understood early that I had to succeed on my own.

These lessons were not meant to be tucked away for the future. I think I was in third grade when the janitor who worked in the courthouse called to speak to my parents. His assistant was on vacation, he explained, and he had observed me in town and judged me to be an enterprising young man, mild-mannered, reliable, and obedient. He asked my parents if I would be interested in assisting him in the afternoons for a couple of weeks.

My mother told me, “You ought to be proud of yourself, Joe, because he called and asked specifically for you. He wants you to work for him because you look like a person of worth. Take the job and prove to him that you are.”

The janitor was a short, thin, gray-haired man, wiry and a bit stooped, close to retirement. He showed me how to sweep the floor thoroughly by tossing oiled sawdust in front of one of those wide brooms, to help pick up the dust and shine the floors. He taught me to empty the wastebaskets in order, so I didn’t work randomly and miss one. He showed me how to clean the bathrooms. After that, we did our work and didn’t say much. And I got money for it. I spent it as I wanted to—it wasn’t a lot. My parents cautioned me not to waste it.

Then I got interested in getting a new bicycle. I suppose I thought my old bike wasn’t good enough. So, I asked my father if I could have a new bike. He said I could have one—I just had to make my own money to pay for it. I asked him how I could go about doing that. He said there were jobs listed in the newspaper, in the section called the want ads. He showed me where they were and promised he would help me understand how to talk when I went for an interview.

I know that plenty of other young people would not have had this reaction, but to me it was like that scene you saw sometimes in adventure movies, where someone opens up the pirate’s chest and everyone’s face brightens with the light reflecting off the treasure inside. You could open up the paper and it showed you where the money was. With this, a whole new era of my life began.

One of my first jobs came not from the want ads but from a family friend, a man named Mr. Verrett, who had some cleaning work he needed done, moving some trash. He paid me with a check, and he said, “Joe, I’m going to take you to the bank,” where he helped me open a savings account. I recognized some of the tellers from church, and one of them gave me a little savings account passbook. Every time I gave them more money, the clerk would write by hand the amount of the deposit and the interest I had earned, so I could see the savings accumulating. I can’t express how important I felt when I handed my couple of dollars through the window and the clerk wrote the amount into my passbook. Some kids got that feeling from sports, but my body never functioned in the way that makes a good athlete. I never knew if that was because I didn’t have the interest in sports, because I didn’t try hard enough, or because I was simply born awkward. Playing sports, I felt like a clumsy kid, but at the bank, I felt like an adult.

I loved seeing the money add up, watching it grow by two, three, four, eight dollars. I kept adding to it. To work, to make money, to watch it grow—that was my secret thrill. None of my friends were doing it. School was not exciting like that. When I was older, in the tenth grade, my algebra teacher took me aside after we had taken an IQ test and she said, “Joe, you can do better. You have an IQ of 120, and that means you can get better grades.” But I had no desire to achieve better grades. If I could get a C and get through the class, that was enough for me. I did have the desire to work, though. I always had a job—first a paper route, then a position as a clerk at the grocery store. I was a carryout boy and stocked shelves and swept floors, and I enjoyed it. If a skill is something you have to learn and a talent is a gift you are given, then working, liking to work, was part of my talent.

These jobs became a kind of parallel schooling for me, not in knowledge but in responsibility. I was fortunate to work for people who honored me by taking an interest in the character of a young man. My boss on the paper route was Mrs. Enright. She saw her role as teaching young boys to understand what it meant to do the job well. She gave us reasons: You have to be here by four in the afternoon and here is the reason why. You have to count your papers, and this is the reason why. You have to remember your bicycle or wagon, and these are the reasons why. She was a caring person who was teaching us responsibility with love and with explanations.

Then I became a clerk at a grocery store, working for Norm Stellick, who was not a gregarious man. He did not use a word if he didn’t have to. He was a good man, but darn it, he never said a nice thing. The floor wasn’t clean enough, the bread wasn’t stacked right—he would always call your attention, very sternly, to what was insufficient. His tone made you think to yourself, Boy, I hope I never get that wrong again. He’d correct with a reprimand or a frown. He used harsh words. In retrospect, I can see that he wasn’t cruel, and that the grocery business was hard work for little money. He hired me when I was in eighth grade, but he expected me to take responsibility like an adult—here’s what you have to do, now do it.

Based on my experience at the grocery store, I was then able to get a prime job: clerk at our local Rexall drugstore. With a job like that, you weren’t out in the Nebraska weather, you didn’t have to get dirty, and you were helping people. It was the crème de la crème for a boy in Nebraska City—none of my friends thought so, of course, but I sure did. My friends Jerry Gress and Jerry Schmitz worked for a while in a grocery store, and they recognized that I had a better job situation than they did, but it wasn’t meaningful to them the way it was to me. Jerry Gress remembers my telling them that one day I would like to be a millionaire—a million dollars was, to us, the epitome of rich.

“Why, Joe?” they asked me.

“It would be an achievement,” I said.

That didn’t seem to mean anything to them.

The owner of the drugstore was a rough, gruff old man named Fred Whit. Big and heavy, he walked around the store passing gas, but he was so old, he didn’t care. Mr. Whit had opened the pharmacy back when the town didn’t have one, so people had to go there to shop, but he made some customers uncomfortable. My mother was one of them. She was afraid I wouldn’t be able to get along with him and also afraid that when she came in, he would embarrass her.

I got along with him fine because he seemed like a step up from Mr. Stellick; when Mr. Whit was disappointed, you could hear the words he was thinking in his head, but at least he didn’t actually say them to you. And working for him, I learned that you couldn’t crap your pants every time someone chewed you out. You have to do your job, and if you get something wrong you just take the criticism and try to make him happy the next time.

One day old Fred Whit passed away, and his younger partner, Lee Jessup, bought the store. In a lot of ways, they were opposites—Mr. Jessup was short, skinny, and well attuned to the fact that his customers could choose to take their business to the competition. He worked with a smile on his face, always deferential, making customers feel good. At a drugstore, you sell awkward things. Ladies came in to buy big boxes of Kotex, so he taught me to speak discreetly and wrap their packages so they felt comfortable carrying that large box out of the store. Men came in to buy prophylactics, and to hide their embarrassment they used slang terms. It was a time when people didn’t talk about such things in public. I had to know what it meant when a fellow asked me in a low voice, “Do you sell raincoats?” Under Mr. Jessup’s more customer-focused management style, the once-struggling store prospered. I absorbed all the experience from using the sales techniques I learned and their effects on customers as if they were passing through the cells of my skin.

Mr. Jessup got sick and passed away while I was still a young man. Bill Carroll, the pharmacist, bought the store. He had gone to Creighton University, the Jesuit school in Omaha, and he was a Catholic. He took a special interest in me, and later, when I was applying for jobs as an adult, he wrote me character reference letters and customized each one to suit the job and place of business to which I was applying.

Each of them, I felt, honored me by taking an interest in me. I learned social skills that many other young men, who knew only school and sports, didn’t learn, and that gave me an advantage. They helped to shape me and also, I would realize later, to shape my ideas on how a business owner should treat their employees.

Every once in a while, as I worked my jobs and made my deposits into my savings account, I’d want to buy something. I would go talk to my dad about it. “You can buy it, Joe,” he would tell me. “It’s your money. You earned it. But understand what that’s going to do to your savings account, and what it’s going to do to you in the future.”

I wasn’t told no. I was reminded that I could do with my money what I wanted, but I was also given some direction. Sometimes, when I told my mother about a new job and the money I had made, she would say, “That’s what you’re going to use to go to college. We can’t afford to send you. You’re going to have to do it yourself.” And that was why I didn’t buy the bicycle or the gun or whatever I was thinking about.

My friends would ask me why I wasn’t playing baseball, why I wasn’t playing basketball. I told them, “I got a job. I prefer to work.” My parents had never discouraged me from playing sports, but they did encourage me to make money. And my friends didn’t understand that I did not have the urge to do what they did. It hurt sometimes that my peers rejected what I cared about. Especially with girls—it seemed the girls all went after athletes, but I was carrying newspapers, clerking in a drugstore. None of the girls seemed to care about boys with jobs.

My best friend would ask me, “Don’t you feel bad that you’re giving up all this fun? Sports?”

I said, “No, I enjoy what I’m doing.”

Senior year, though, they needed a fifth man for the school basketball team, and I had gotten tall. I quit my job and joined the team, but I was never a good athlete. There was only one guy bigger than me, but I was not a good basketball player, and I didn’t really care for it. I never seemed to have that physical gift that athletic kids have. One summer, I tried to work for my dad as a carpenter’s apprentice, but I was no good at it. He fired me.

I know that some kids imagined I didn’t care for fun, but that wasn’t true. I liked having a good time as much as the next person, and Nebraska City was really quite wonderful for a kid growing up. I feel now like I grew up in heaven and didn’t know it. In the summertime, when I was still little, my mother would pack me a lunch in a sack and I’d tell her I was going to the park or what we called the camp, a place in the woods that was good for playing and fishing, and then she wouldn’t see me until suppertime. For a boy growing up, you couldn’t ask for anything better. You had your fun and you went home, and you didn’t tell your parents what you did. Maybe you had a scratch, and your mother would ask, “What happened?” And you’d say, “I got in a fight with Bob.” And that was the end of it.

She never worried about me all day long because everyone in town knew who I was, and there were eyes everywhere, watching me. Every once in a while, somebody in town would call her because they saw me doing something I shouldn’t, like tipping over somebody’s garbage cans. We always had that awareness: Gee, no matter what I do wrong, I might get in trouble here. It was nice from a parent’s point of view, and it was nice from a kid’s point of view because it allowed for a lot of exercise in judgment and character development.

When I was in the Boy Scouts, for example, we had to cross a bridge to get to the meetings. We used to bring eggs with us, hide under the bridge, and throw the eggs at passing cars. We thought we were smart and that no one knew who was doing it. Then one day we went into the police station to get a drink of water, and the police officer called out to us, “Quit throwing the eggs at the cars! It ruins the paint!” And that was the end of that.

Most of all, I loved the Boy Scouts. We had a wonderful scout leader who didn’t worry about merit badges, he just let us run free and have fun. Generally, that meant fighting with the other camp. We’d have a sort of war. We’d see who could collapse the most tents by pulling up the stakes, who could pour water in the other camp’s sleeping bags, who could beat up the most guys—just wasting time and playing tricks like that. I can remember sneaking up on their campsite at night, with all the guys standing and singing in front of their bonfire, and tossing a cherry bomb into the flames. That stopped the singing right away. After the explosion, the whole group came after us, and we ran away through the forest, laughing.

At Boy Scout camp, it felt like we were a thousand miles away from home and church and all the rules, with nobody to oversee us. There was still somebody keeping an eye out though, so if a kid broke a leg, somebody was going to take care of it. I still remember our troop leader. He lived in the neighborhood and everybody knew and respected him. He was a bachelor, and later some people got upset because he was rumored to be a homosexual. He was made to leave the organization. We kids never had any idea about that, and he never did anything he shouldn’t have. He was a great scout leader—I can’t imagine anyone better as an ideal for young men—and I thought his being asked to leave was a tragedy. It made me sad.

As I got older, of course, I had to give up that kind of freedom. And by the time I was a senior in high school, I knew that what I wanted was to go away to college, not stay in town and get a job. As one of my friends from Nebraska City liked to say, it was a great place to grow up and then a great place to get away from. I’d had enough of a place where everybody knew everybody else, where there were eyes and expectations everywhere.

I had saved a few thousand dollars, but Creighton University was expensive, and after my first year all the money I had saved up back home was gone. One of the first things I did when I got to Creighton was look for work. I became the dormitory janitor, cleaning the bathrooms so I could have a free room, and the busboy in the Jesuit dining room so I could have free meals. Then my friend Clark Smith told me about a job opening at a bread factory that paid more than two dollars an hour, and I thought that sounded great. I worked twenty or thirty hours a week, off and on, mostly evenings and weekends, and those were the dollars I used to pay my tuition and buy my beer.

Sometimes they would get big orders at the factory before a holiday weekend. Once, I worked twenty-four hours straight. The first eight hours I got the regular wage, two dollars and twenty-five cents an hour, and I thought that was high. The second eight hours, I got time and a half, which was great. But the third eight hours, I got double time, four dollars and fifty cents an hour, and I couldn’t pass that up. The unionized employees wouldn’t work three shifts in a row, but to me it was an opportunity.

For meals, they only had vending machines with candy bars. To get energy, we’d take a bottle of honey, steal a loaf of bread, break off a piece, dip it in the honey, and eat it. I got sick to my stomach eating so much bread. Sometimes I worked while I was close to throwing up. And it was hard—really hard, exhausting work in very hot spaces. The older people there were very tough. Once, there was an accident and a worker lost a finger in one of the machines. Only after they’d gotten him to the hospital did someone think to ask: Where’d the finger go? It wasn’t on the ground outside. It wasn’t on the factory floor. It wasn’t in the machine. We went out to the docks, where there were three semitrucks full of packaged bread, and we realized the finger was in there somewhere on one of those trucks. Then the manager said, “Hey, ship it.” So, the bread was shipped, and some customer found a finger in her loaf. To this day, the smell of a bread factory reminds me of working those long hours with an upset stomach. It makes me feel sick.

Thrilled as I was to have that factory income, I learned that I was going to have to find another way to be thrilled, because the work was not the kind I wanted. That was further motivation to get through college, even though the classes were difficult for me and my progress was slowing. I kept shifting time away from earning credit hours so I could earn more money to pay for them, which meant I fell behind the other students.

One Sunday morning, after I’d been working all night on the production line, the sun was coming up, ushering in a bright, beautiful day. We didn’t have any windows we could see out of, but there were windows near the ceiling. Later, I climbed up on some of the huge pans to look out, and I could see young people in convertibles going on picnics or to the beach. They were having a nice, leisurely day. I thought, Boy, you know, that looks fun. I want to make enough money so I don’t have to work on Sunday and I can go to the beach too. I felt what it would be like to get out of that factory and make sure I could have a good job, a house in a nice neighborhood, a car, and some leisure time.

I could claim that at that moment it all became clear. “That’s what I want someday! And I want my kids to have that too.” I could say that this vision inspired me for all I achieved later. It would make a great story, but the truth is that with all the money I earned later on, I never bought myself a convertible. My son Todd eventually gave me one, a Mercedes 280 SL, a beautiful classic car. He said, “You’re never going to buy it for yourself, so I bought it for you.” I enjoyed that he bought it for me, and I enjoyed driving it, but did I drive it to the beach like I imagined that morning in the factory? Never. I’ve been to the beach once or twice, but the truth is that to me, things like cars and seaside vacations are pleasant, fun now and then, but not deeply satisfying.

For me, it’s the getting there. It’s the competition, the problem-solving. It’s being right when no one thought you were right and winning when the stakes are high. Even after I had more money than I could spend, I went on working forty to sixty hours a week. I still wanted to succeed at business, not for the increased buying power that success would earn me, but for the pleasure of making a business succeed.

To me, looking out that factory window at the beautiful convertible, the open road, the day that could take me anywhere, was a vision of freedom. To know that I have earned the freedom to do something, that feels glorious. But actually doing it? That’s not the point. Rewards, for me, were the wrong motivation. I wanted to work hard, make money, give it everything I had, and build something that would last for myself, my children, and the people who worked for me. I just didn’t know, yet, what to build.

About The Author

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Joe Ricketts is the founder, former CEO, and retired chairman of online brokerage TD Ameritrade, and the author of The Harder You Work, The Luckier You Get.

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"Good reading for budding businesspeople."
- Kirkus Reviews

"[Joe Ricketts's] story of building his business through acquisitions and by adopting new technologies from the 1970s until its merger with TD Waterhouse in 2006 will give the reader a candid look at an entrepreneur in action."

"As inspiring as it is instructive."
- The Federalist

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