Prologue

I remember the exact sound my office made when I finally stopped working. It was quiet in a way that felt deliberate, like the building itself had decided it was done with me. The hum of the fluorescent lights, the faint buzz of my computer fan, the distant echo of traffic—it all pressed in at once. I sat there staring at a spreadsheet that no longer meant anything, knowing that if I closed my laptop, I might not open it again. Not tomorrow. Not next week. Maybe never. That was the night I came closest to walking away from everything I had told myself I was building.

Eight months earlier I had walked away from a steady job with $18,000 in savings and a spreadsheet I thought could change an industry. Was I naïve? Maybe. But I believed in what I was building, believed in it with a passion bordering on obsession. I had been in logistics, working for an LTL company with a small but growing fleet of semi-trucks. It was a company that still handled its payroll internally, with thirty-five employees, three middle-managers and a CEO who couldn’t be bothered with details.

 I enjoyed the work but after some time I began to notice a number of inefficiencies: drivers calling in manually for updates and often losing their paper logs; dispatchers overwhelmed. I built a rough system in Excel to track routes and delivery times and thought perhaps I could create software to expand upon my idea. Of course, I didn’t know how to code but I wasn’t about to let that stop me.

I continued to work on this passion project in my spare time, adding functionality and complexity, yet keeping it lean. When I felt I had taken the spreadsheet as far as I could I decided to share it with my immediate manager, Frank Selinsky, to get his opinion. Frank was dismissive at first; but after a few minutes I convinced him to try using it for a week and see if it made a difference in his workflow.

A week later he showed up at my desk. “This worked really well,” he said, laying a handful of documents on my desk. “I made some notes, some ways I think you could build upon what you’ve created. Let me know what you think.”

I spent the next two months working, almost every night, from 9pm to 2am in the morning, teaching myself how to code and building my product at the same time. I was determined to succeed.

Fast forward to the present. I had been rejected by fourteen investors as well as multiple business prospects. The biggest blow? A trucking company had verbally committed…then backed out at the last minute. My bank account was under $2000, my credit cards were maxed, and my aging laptop had begun crashing during demos. My girlfriend had left me, complaining that I was there but never present. I’d lost contact with most of my friends and ignored my family’s pleas to stop chasing this pipe dream and go back to my day job.

But I wasn’t done yet; I wasn’t ready to give up. I had come too far to just let this dream slip away. I knew I could make it work. I knew that with a little luck and the right customer I could take this thing all the way.

Chapter One

I grew up in a blue-collar family in a suburb of Chicago. My father worked as a mechanic at a dealership; my mother, a receptionist at a dental clinic. I had always known I was made for bigger things, for more than what my parents could offer. I didn’t feel guilty about this.

I did well in school, straight A’s, excelling in math and English. I had a close-knit group of friends and a steady run of girlfriends, though none of my relationships became serious. I was right halfback on the school’s soccer team for four years and a long-distance runner on the weekends.

If you had asked my family or one of my friends to describe me in two words or less, they probably would have said I was laser-focused. Obsessed even. I attacked everything I did with high energy and determination, never settling for anything less than the best. I set stretch goals and had lofty business aspirations: I was going to earn an MBA, or even own my own business.

By the time I became a senior I had my heart set on Columbia University; with it’s strong focus on business and in close proximity it seemed like the best choice. My parents were happy I would be close by and I was glad to have the support.

I graduated high school valedictorian and top of my class. I’d already been accepted into Columbia and was looking forward to my remaining summer before college. While my friends planned trips overseas and gap years I waited, patiently, for September to roll around. I was anxious to begin this new direction in my life, to pursue my dreams and show the world what I could do. I spent the summer working at a local building and supply company; they’d hired me when I became a sophomore and I’d worked there every summer since. I was saving my money to use at college; I wanted to be self-sufficient and not have to rely on my parent’s generosity, even though I knew they would have gladly pitched in.

I became very introspective that summer. I read a lot, philosophy and poetry, and thought about my place in the world and the sort of impact I wanted to make. I believed in God but didn’t consider myself a Christian, though I felt very strongly that a person doesn’t make their way in the world by stepping on people. I valued honesty and integrity and was determined to live my life according to those values, something I continue to do to this day.