The Rideshare Diaries: Riders Share Their Stories

By Byron J Siegal

I didn't start driving for Uber because I wanted to write a book. Still, counting up till January 6, 2023, I've clocked 18,002 Uber trips, starting back in October of 2019. Along the way, I started talking to passengers. Many come in preoccupied with their phones or on a phone call-setting up a date, ordering tickets, calling Mom. If a passenger

• Language: English
• Publisher: Byron Jay Siegal
• Release date: May 6, 2024
• ISBN: 9798990449817

Byron J Siegal

Byron Siegal grew up in Worcester, Massachusetts. He attended Clark University and received a bachelor's degree in 1971. He obtained an MBA from the University of Hartford in 1974. In 1978 he started with Ethan Allen furniture as a district manager for upstate New York and Canada. He was there until he decided to go to law school. He graduated number two in the class from Vermont Law School in 1984 and moved to Portsmouth, New Hampshire to open a law practice. He practiced law in New Hampshire and Maine until 2006. During the time of his law practice he developed a jazz camp for adults which ran for thirty-five years. Participants came from all over the world. Along the way Byron became a flight instructor, CFII and a large part of his life has been flying for enjoyment. In 2017 Byron moved to Boston for medical reasons to be closer to the site of his clinical trial. That's when he started driving for Uber. Two months after the Uber beginning, the idea for a book percolated when he seemed to meet collaterally related people. In one two-day period he met four venture capitalists that invest only in biotech companies. One venture capitalist had invested in a biotech company developing a DNA strand to inject into the ears of genetically deaf people. A month later he ran into a researcher worked on drugs for deaf people. She knew the company working on a DNA strand, Akkuos. It was after these meetings that he decided to write a book.

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PREFACE

I REMEMBER MY DAD HOLDING me with his strong hands over the porcelain sink hanging off the wall so I could pee. I was four. We were staying in a guest house in Misquamicut, Rhode Island. All I remember is that it was dark, weathered, grayish-brown on the outside. We didn’t have access to a toilet all night, just a sink. I told my father I had to go at five in the morning and he gently picked me up and took me to the sink. He told me to go and that it was okay. This did not sit well with me since my potty training was not yet a distant memory. It was my first experience going outside the toilet since I first learned how to use it. That was my introduction to being on vacation.

The vacation was full of beach sand and rolling ocean with waves to body surf in and a strip of buildings. At night the buildings lit up, punctuated by takeout food places: fish ‘n chips, fried clams, clam chowder. The tourists came. The quasi boardwalk was filled with wall-to-wall people walking four abreast. The buildings on the strip all looked the same—white with green roofs. One building caught my attention as we walked by in the evening. The door was open on the side. I looked in.

Musicians in white dinner jackets sat in formation. What caught my attention was the shiny gold-looking metal thing shaped like a sideways S. It was held by a white-jacketed man with black slicked-over hair, and he was blowing into it. At the time I didn’t know what it was, just that it was shiny and made sound. It was loud. Later I learned it was a saxophone. The band played on with a vibrating, joyous beat, the same joy found in a New Orleans Street band.

It was the fifties, and the music of Frank Sinatra, Count Basie, and Duke Ellington were still extending their World War II dominance. Dance halls were populated with foxtrotting, jitterbugging youngsters sweating, jumping, and connecting through the music. Back in the fifties, it was the place to go, the club, the scene.

That was my first exposure to big band music, big band jazz. I will always remember it. Somehow, I was connected to it. Now I think maybe I was a dinner-jacketed musician in a past life. I grew up studying clarinet and saxophone, the shiny-looking instrument I had seen when I was four. I played in a big band at New York University with jazz legend Dave Liebman. In 1984, I started a jazz camp. It lasted for thirty-five years, attracting musicians from all over the world.

I took jazz improvisation lessons with master saxophonist Jerry Bergonzi when he lived in Brighton, MA. I had heard of him and finally got hooked up to study the methods of jazz. At my first lesson, he asked me to play a tune, me on saxophone and Jerry on piano. After a few measures of music, he turned to me with a wry, knowing smile and said, You must have been a musician in a past life. I’ve always believed that. It explains that below-the-surface feeling I had when I was four and didn’t understand any of it. As Yogi Berra said, It’s like déjà vu all over again.

To pay the bills, I started working at a movie theater as an usher at sixteen; moved on to buying in the Boys Department at G. Fox and Co in Hartford, Ct at twenty-three; opened a soft frozen yogurt store in White Plains, New York at twenty-five; did the District Manager gig for Ethan Allen Furniture in upstate New York and Canada at twenty-eight; and went to law school at thirty-four, practicing law for thirty years. Along the way I took flying lessons and became a flight instructor. Yet throughout my life, music was always there, dating back to that shiny gold instrument I saw when I was four. Now I’m an Uber driver. That is the arc of my life. Now every day starts the same.

I roll slowly roll out of bed around 5:45 or 6:00 a.m. Look at the clock. Is it time to get up? Usually, yes. I turn on the water in the bathroom and the kitchen sink so it will get hot. Now, I look for my Little John (portable urinal). I first learned about it and used it while flying, as there are no bathrooms in small airplanes. Little John is my best friend in the car. If I didn’t have it, I would spend all my time looking for a bathroom and a parking space in Boston. Good luck with that. In any event, I have to empty it and rinse it out, the reason for the hot water. When it’s done, I place it on the floor by the door. Step one done.

Step two, I need to collect my vitamins and put them in an old pill bottle so I can take them throughout the day—Zinc (to prevent colds), Vitamin E (for muscles), DHEA to keep the boy juice flowing (testosterone), Vitamin D (because my primary care doctor said so), Drenamin (to support adrenal function), fish oil (for my brain), saw palmetto (from Amazon to support prostate function), thytotropin (to support thyroid function, and last but not least ultraflora (a probiotic for digestive health) and folic acid (to support heart health). Once I have them all on the cutting board, I sweep them off with a grand motion and pour them into the bottle. Step two done.

Step three, look for my prescription medicines, Diltiazem ES (for rapid heartbeat), Toprol XL (for the same), a baby aspirin, and Prilosec (for acid reflux). Once I get them together, I put them in a Glad wrap and fold them. I take both the pill bottle (vitamins) and the squished up Glad wrap and put them on the floor by the door along with the Little John. That way I can eyeball it all before I leave. Step Three done.

I shave, throw my jacket on, and do a final check that I have everything. Vitamins, check; prescriptions, check; Little John, check; apple in bag, check; phones, check. I’m not coming back until I’m done driving (6-9 hours later, depending on the day).

I didn’t start driving for Uber because I wanted to write a book. Still, counting up till January 6, 2023, I’ve clocked 18,002 Uber trips, starting back in October of 2019. Along the way, I started talking to passengers. Many come in preoccupied with their phones or on a phone call—setting up a date, ordering tickets, calling Mom. If a passenger is free to talk, I ask questions. Where are they going? What do they do for work? How does their job work? If in biotech, what drugs are they working on? If an electrical engineer working on a NASA experiment, what part do they play in getting it into orbit?

I asked lots of questions and started to get questions answered. Patterns emerged about how passengers ran their lives. How they were actively successful in their fields and living successful lives. Everyone has a story. In December of 2019, I asked Dave Loverock from Jet Ice outside of Toronto, Ontario if he would agree to be interviewed for my book. He told me he does ice. What the heck was that? Immigration and Customs?

No, it turned out he does ice for all the National Hockey League rinks and the Olympics in South Korea. He was my first interview. I learned how ice was made, why the ice is white, and how the logos get infused into the ice. Dave told me how he went from selling high-end audio equipment to becoming vice-president of Jet Ice. What I really learned was how Dave became who he is—the arc of his life.

From that interview and fifty-four others that followed, I studied the turning points in passengers’ lives. How did they deal with those anxiety-filled, sometimes dark, sometimes light, sometimes terrifying moments that made them who they are? I learned what passengers hold to be important. I created this book to tell their stories, to tell the arc of their lives, and to learn from them the keys to their success. This book has thirty stories out of the fifty-four interviews I conducted. Maybe there will be a book two! These stories inspire me. I hope they will inspire you too.

I’ve organized the book around the concepts that my passengers’ stories manifest: how to be successful, how to be happy, how to know what you should be when you grow up, how we can save the planet, and how riders extend a helping hand.

Many of these interviews occurred during the active phase of the COVID-19 pandemic, pre-vaccines and pre-medication. Some of the stories note the adjustments they had to make during that period. In a few of the stories, I got personally involved. In one case, a passenger bought me dinner. Another passenger offered to do a Tarot card reading, which I accepted. My favorite was being asked to join a mother and daughter at a Red Sox-Yankees game at Fenway Park. It was behind home plate, one row back from the wall!

When I was in law school, I frequently could not remember case names, but I always remembered the stories behind the cases. It’s easier to remember stories. Rules and prescriptions, maybe we don’t remember them—there’s nothing to hang on to in them, they are just words put together—but a story, a story filled with drama, feelings, and emotion, you can remember that. A story can pop back into your head when you need it most. I hope the lessons offered by the Uber riders can be helpful to the reader. I hope you enjoy the book.

1. HOW RIDERS

GET

WHAT THEY WANT

PERSISTENCE

I don’t have a Plan B. I’m not poor but I have to work seven days a week to keep going. I’m seventy-four, about to be seventy-five. Who is going to hire me? Through some bad planning and bad luck, I’ve ended up needing to work every day just to have what I need to live. I’m an attorney (retired) and I’m a flight instructor, and yet I drive for Uber to pay the bills.

When I first thought of this book, I was in my car driving an Uber passenger. She had just told me she did research for a pharmaceutical company that worked on drugs for deaf people. I had driven a medical venture capitalist a few days before. They had financed a company working on an injectable DNA sequence that could allow deaf people to hear. Of all the Uber drivers driving in Boston, how is it I was seeing these two people within a few days. Karma? Destiny? Luck? The lightbulb went off: I should write a book!

At this Eureka moment, a comic bubble appeared in my head with the caption, I’ll write a book, I’ll be rich! Not so fast, kiddo. On every project I’ve ever started, I thought because I loved something that everyone else would too. I started a jazz camp for adults after directing the Vermont Law School Community Jazz Ensemble for two years. I thought because I loved jazz and big band that customers would flock to my camp. I planned five weeks the first year and did two.

I thought a classified ad in Downbeat (a jazz magazine) would bring them running! Four participants signed up. My dad, always the gambler, loaned me $3,750 to place an ad in The New York Times travel section. The Times placed it on the wrong page and had to run it again. I was interviewed, and they wrote an article about the camp. I finally had twenty participants.

The Jazz Camp has been much like the book—lots of starts and stops, lots of great ideas that didn’t turn out well. But I kept going. My sister-in-law talked me out of selling the camp in year seven. I got an article placed in AARP, and the internet happened, and we were off and running for thirty-five years.  

With my Jazz Camp, I didn’t quit at the first sign of difficulty, and it’s been the same with this book. I first thought everyone would love stories written about Uber passengers. Why? Because I was writing them, and they were interesting to me. Another one of those, If I love it, everyone else will too. Over two hundred agents and publishers rejected the first version, although I did get some good ideas from a few of them.

I brought someone in to help me find direction for the book and I kept bothering him about how we would redo the table of contents. One of the things I don’t do is research. He pointed me to two articles about best practices for non-fiction books. From those articles, I learned how to structure the book in an acceptable way and how to write an introduction.

Those suggestions forced me into finding a theme for the book that you have before you now, The Rideshare Diaries: Riders Share Their Secrets. These stories were always there. I just hadn’t focused on them in organizing the book. So great, now I had a new template and a new table of contents and a new organizing theme. I started contacting agents again.

Two of them sent me back a message: I like the idea, but the writing didn’t ‘pull me in.’ So now I had to go back and look at that—the writing wasn’t good enough. I contacted several friends and rewrote the introduction. One of my flight students wrote me back, It’s like a history book, and the sentences are too long. I was immediately depressed, and my heart sunk. He followed up with a suggested reading, The Life and Times of the Thunderbolt Kid, by Bill Bryson. I noticed in reading that book that the author had some funny twist every few pages, and so I gave that a try: shorter sentences, and some humorous references every so often.

Resubmitted. My friend the flight student and avid reader liked it! Not a history book anymore, reads more like a novel, he said. It’s a light at the end of the tunnel. Is the light green, blinking yellow, strobe white? Regardless, I had to press forward! That’s what I’m doing now. I keep moving forward, experimenting, modifying, editing, trying other things. As with the jazz camp, so it is with this book: I’m not giving up.

The Uber passenger stories in this chapter are tales of persistence. Matt’s Verta Corporation story is up first. When he went to a career fair at his college, he went to the first table he saw to get the nerves out. He went back three times that day to impress. He got a call back for a second interview the next day. Persistence pays off.

There is one other story in this chapter that demonstrates persistence and the results that can come from it. It’s about Uber passenger Dave Sklowdoska, a project production manager at Gingko Bitotech, whose motto is, Sometimes you have to jump through flaming hoops of bullshit to get what you want. Persistence: it’s not surprising it’s important. George H.W. Bush has been known to use the expression, Ninety percent of life is just showing up. We need to add to that, repeatedly. After all, that’s what persistence is: showing up over and over again.

BYRON’S RULES FOR PERSISTENCE

1. Commit yourself to a goal

1. Keep doing things that will lead you to your goal and do them repeatedly

Matt—Skyscraper Crane

Maintenance Engineer

I am 5’5, 145 pounds, and I’m stocky. I’ve got long brown hair that’s always in a bun and big blue eyes. My eyes are the first comment I get from new people, especially women."¹

Rider Lesson #1: insert yourself into situations that you desire.

Matt grew up in the Iron Range in Minnesota, the biggest deposit of iron ore in the world. Virginia, Minnesota was a town of about one thousand. It was four miles to the nearest store and about a one-hour drive to Duluth, Minnesota. Matt grew up building stuff and working on bikes. He was an avid dirt bike rider. At sixteen he started going on road trips and attended the Somerset Festival in Wisconsin. He fell in love with the freedom of the road. He spent as much time as he could making money so he could take trips and go camping. When he was later offered a job that involved nationwide travel five days a week—not to mention the chance to work at the top of tall buildings—there was clearly no other choice.

Matt studied mechanical engineering in college. While he was there, a custom motorcycle shop opened in Virginia, MN named Malicious Cycles, and he started frequenting the shop, hanging out, talking to the owner. He would go on a Monday, return Thursday, show up on the weekend. Every day he had the chance, he just kept going back, showing up, offering to help, learning what he could about custom bikes.

In his junior year at Minnesota State University in Mankanto, MN, he had to do an internship. The University offered him an internship working on a machine that would automatically debeak chickens. Matt was a gearhead, not a chicken-head. Matt went back to the Malicious Cycles and talked the owner into allowing him to do his internship there, building custom bikes and traveling all over with a dyno machine that measured the performance of motorcycles at speed. (A dyno (or dynamometer machine) is like a treadmill for cars and motorcycles with attached electronics.) That became his life—traveling on weekends and in the summer to motorcycle shows and working with bike owners to improve performance on their motorcycles. His persistent presence at Malicious Cycles throughout his junior year made his ask for an internship a no-brainer for the shop. Persistence at work.

When they were not building custom bikes at the shop or going to shows, they would take scrap metal and weld them into sculptures. They brought these sculptures to the shows and gave them to motorcyclists as trophies for the most improved performance of the bikes at that show. Matt had become a certified welder in the process. Matt had inserted himself into the Malicious Cycles biz.

In the spring of his junior year there was a job fair scheduled for an upcoming weekend. The Minnesota State students and their teachers took the job fair seriously. They practiced at mock interviews and researched the companies they wanted to interview with. In Matt’s case, that meant library time looking at Caterpillar, Polaris, and Bobcat, all manufacturers specializing in mechanical vehicles and engines. The day of the job fair came.

Matt was nervous, but as he walked into the conference center, an idea bubbled into his consciousness. I’ll just go interview with any company to get the nerves out. As he entered the door, he turned to his right to be greeted by a large map of the United States taking up the entire wall of the display space. Okay, this looks good, I don’t know who they are, but a good place to start. He walked to the table.

This was Verta Corp. He spoke with the company representative, Dan, who told him that if he worked for them, he would be traveling five days a week, it would be nationwide, and he would work at the top of tall buildings. Matt’s eyes went wide as saucers. He left the table thinking, That’s the job I want! He proceeded to talk to his previously researched companies, Polaris and Caterpillar, but came back to Verta to talk to Dan again.

After the second visit, he thought, I’ve got this really cool air engine back in my dorm room, I want to show it to Dan. (An air engine is a reciprocating engine powered by air.) He ran back to the dorm, got the engine, ran back to the conference hall, and showed it to Dan. Dan thought it was the best thing since sliced bread. Later that day, Matt went back and helped Dan break down his exhibit.

Matt left the conference hall hoping that Verta Corp. would call him back. He had done everything he could to not be forgotten. The next morning, Dan got a call from Verta. They wanted him to come to Minneapolis to see how he handles the heights. The day after, Matt was on a plane to Minneapolis, and early in the morning he was sent out with a crew to a seventy-story building. He went up to the roof with the crew. This building had a crane on it that had an articulating arm that extended over the edge of the building. The crew strapped Matt onto the articulating arm of the crane and sent him one hundred feet out over the edge of the building, seven hundred feet