Read Entire First Chapter:
“Where it all Began”
Every morning I watched him. The sun would rise and the long-haired hippie surfer would stand alongside his coffee cart, selling mediocre java to San Diego’s corporate suits.
It was 1994 and my best friend Andy and I had just graduated business school and moved to one of the most ideal cities in the country. With an average yearly temperature of 70.5 degrees and the beach just minutes away, there was little wrong with this picture except that the country was in a recession and we had spent months sending out resumes and going on endless job interviews. Eventually, we both landed jobs at GEICO Insurance, which saved us from having to move back home with our tails between our legs. We were adjusting to our corporate life just fine until we saw the surfer dude.
He stood outside in the courtyard in his sandy flip flops for just a few hours every morning, handing out cappuccinos and coffee to the men and women making one last stop before bustling into work. Who can make it through their nine-to- five without a little extra jolt anyway? It wasn’t that Andy and I wanted so badly to sell coffee like the surfer dude. No, we wanted so badly to have the life that followed the coffee…the beach, the fun, the freedom.
Day in and day out I watched. From behind the glass of the insurance company office window, I saw him pack up the cart and roll it away around 10 o’clock. Then he headed to a day that was all his. I wondered what it would be like. How would it feel to be my own boss? To have the luxury of making my own schedule? To play more than I worked? As the days and months passed, Andy and I knew it was what we had to act on: come up with a business that allowed us to do all of those things.
We thought our business proposal for the Grateful Grape, a wine and organic foods shop we hoped to open back home in Illinois, would be the wings with which we would fly out of the corporate world. So I headed home to Normal, Illinois, where we had grown up, to attend the wedding of two of our best friends and simultaneously make pitches to a couple of local banks for financing. Andy stayed behind.
When I landed at the Peoria Airport, I walked through the terminal with confidence and high expectations for the business meetings to come. My confidence came from the incredible amount of work Andy and I had put into this business plan. Working all day at GEICO, we couldn’t wait for our daily grind to be over so that we could hurry home and work on the Grateful Grape concept. For weeks we spent the majority of our nights and weekends writing a business proposal with the tools we had learned at Illinois State University business school. We had done all of the preparation and followed all of the rules. We went above and beyond, and I was quite confident the banks would love our genius idea.
This was my baby, our baby, and we had arranged for me to get face-to-face with the loan officers, and Andy trusted me to get the job done. I wouldn’t let him down. When I walked into that first meeting, my dad and stepmom accompanying me, I was well prepared and had a comfort that came from hours of rehearsing the night before. I was visibly passionate in my presentation, and my prep work allowed me to field all of their questions and relay the perfect answers. I told them why this town would love our small upscale wine and food shop. We would bring in wines that they didn’t carry in the local liquor stores and do tastings to introduce our customers to the products. We’d have an organic food section and microbrews with offerings you couldn’t get in any grocery store in town. We had all of the distributors in place, two different retail spaces to choose from, and the contractors lined up for the construction. We planned to launch in a temporary space in Eastland Mall for November and December to capitalize on the holiday rush and gain exposure while our permanent location was being built out. My pitch was solid and my dad was beaming with approval.
The second meeting, which I took on alone, was even better than the first. By the time the sun set on the plains of Peoria, I wasn’t worried about which bank would approve the loan. I knew I’d have my choice, and I was going to choose the bank that offered the best terms to launch our first business.
It was a whirlwind weekend: meeting with the bank, attending to my groomsman responsibilities at Dave and Jenny’s wedding, and wooing the woman I would later call my wife and business partner. Even though I’d known Dave and Jenny for years, it wasn’t until the wedding weekend that I met Dave’s little sister, Kristen. She was a bridesmaid, which gave me the opportunity to get to know her in a short amount of time. After dinner I asked her to dance. As we took the dance floor, unending thoughts whirled around in my head about what the bank would decide. What would this mean for mine and Andy’s future? And would I ever again see this beautiful girl, whom I was twirling around the room?
I returned to San Diego after the wedding and all I could think about were the banks. I was waiting for the phone call that would change mine and Andy’s entire lives. Within a few days of being back from the wedding, I followed up with each bank. When I called the first bank, they promptly gave me a flat no. This knocked me back, made me feel dizzy and unsteady. They didn’t like the fact that this was an unproven concept for Bloomington, or the fact that we didn’t have a deep pocket cosigner for the loan. The second bank was my second call and my only hope. They relayed a laundry list of demands that were being made by the underwriters who were reviewing our loan request; we were being asked to submit a substantial amount of additional information. This gave us hope and we spent two painstakingly long days flushing out more details and answering all of their questions. We were confident that this would be exactly what it took to get the approval. Now all we had to do was wait.
After two long weeks of anxiously waiting for the bank to come back with a response, we finally got our answer. Andy and I walked into our apartment one afternoon after work, hitting the button on our answering machine as we did our daily unwind. Within a second of listening to the recorded voice, I knew we were being denied our loan. I was overcome with frustration and disappointment that we would never get out of this job and on to a life truly worth living. I remembered the surfer dude and his coffee. In that moment I decided that if we couldn’t quit this job to open a wine shop, then we’d just do what he was doing.
So we picked ourselves up, dusted ourselves off, and began searching out locations for our coffee cart. We scoured the city, looking at everything from beach boardwalks to suburban corporate parks to downtown high rises. We were optimistic that we’d find that perfect spot. To our surprise, we found out we weren’t the only ones envious of the surfer dude, aspiring to be just like him.
Every place we were willing to go already had a coffee cart; the market was saturated, and we had been too naïve to think otherwise. To keep our hope alive we desperately needed to come up with a creative way of getting it done. We’d need to chart our own course to reach the same goal. We would still be like the surfer dude, with our own coffee cart, only we decided to be more mobile. With all of the best locations in the city already taken, we didn’t have much of a choice.
“When are we going to quit? Come on dude. Seriously, when are we going to quit?” I asked Andy, the more conservative of our twenty-three- year duo.
I always thought I’d be the one to make him quit the insurance company once we got our mobile coffee cart up and running. But what I didn’t know then was that he’d be the sole reason I’d leave the doors of GEICO and never have a boss again.
When I think back on that time in my life, it reminds me how much courage and boldness it takes to leave security and embark on a path that is all your own. Starting a business that is all yours, with your rules, your schedule and no manual on how to do it or instruction on how to succeed leaves most people doubting their entrepreneurial abilities…
Fast forward just over a year from getting the disappointing phone call from the bank. Kristen and I were dating. Like Andy and I, she longed to escape the brutal Midwest winters, so she had moved to San Diego to attend graduate school at San Diego State University to study Exercise and Health Science. It was December, and Andy and I were still, yes, still at GEICO, wondering every day when we’d finally leave and never come back. Sadly, the day we left for the holidays would be Andy’s last. Kristen and I headed back to Illinois for Christmas while Andy stayed in San Diego for the week. Andy and I worked in the same group at GEICO, so we had to take turns taking time off for the holidays. He took Thanksgiving off to go home, and I took Christmas.
After the let down from the banks, and the hard work of creating our new plan while working the corporate grind, I couldn’t wait for the holidays to arrive. Christmas break would give me some time to relax and time to celebrate. This would be the first Christmas that Kristen and I were spending together, and we were sharing it with each other’s families.
When Kristen and I finally landed in Chicago, I took her to meet my lifelong friends. These were friends whom Andy and I had grown up together with. She already had the approval of Andy, from whom I’d been inseparable since I was five years old. Now it was time to meet the rest of the gang. We partied long into the night, throwing back beers, sharing old memories with too many laughs to count. Kristen’s dad and stepmom picked us up when the night was over because we were staying at their house for the first leg of our trip.
As the hours crept into the early morning, we decided to turn in for the night. Completely high on the wonderful night I’d had, enjoying my best friends and my girlfriend in the city that would always feel like home, I decided to give Kristen her Christmas present. So as she took off her makeup and changed into her pajamas, I snuck out the gift from my suitcase. It took her by surprise when there was a small velvet box waiting on her pillow. I told her of my promise to her, and the incredibly special place she had in my life. I let her know how much she meant to me as I slipped the sapphire ring on to her finger.
As we were relishing this special moment of our relationship, the phone rang. We looked at each other confused, because it was 3:00 a.m. and no one should have been calling Kristen’s home line at that hour. It was Chris, my other roommate who had moved to San Diego with Andy and me. Chris spoke slowly on the phone, barely able to keep his composure but trying desperately, knowing the gravity of what he was about to tell me. It didn’t take five words before I knew something was seriously wrong. I couldn’t wrap my thoughts around what he had just relayed to me. Reeling with disbelief I tried to process it. A police officer showing up at our door with Andy’s driver’s license? Killed in a car accident? Our boss driving drunk? Are you sure he’s gone?
As soon as I hung up the phone with Chris, I fell into a state of paralyzing shock. I sat myself down as my head started spinning out of control. I simply didn’t believe it. I couldn’t feel a thing. My body was completely numb, but I somehow realized I didn’t have the time to be numb, or confused, or in shock. I couldn’t afford that luxury because I didn’t have any choice but to act, and act quickly. I had to be the one to tell Andy’s parents that their son had been killed.
This meant that Kristen and I needed to drive down to Andy’s parents’ house about two hours south of Chicago, just blocks from my childhood home. Only minutes ago we had been unpacking our bags, completely euphoric from the incredibly fun night we’d just had. Now my entire world had been turned upside down. As we shoved our belongings back into our bags, I got on the phone because I still wasn’t ready to accept the truth. I called the coroner’s office in San Diego to see if this could really be true. They assured me that his identity had been properly verified and that they were processing the death certificate. There wasn’t a shadow of a doubt that someone had gotten this wrong. I called my dad and my mom to tell them the crushing news, borrowed a truck from Kristen’s dad, and we headed out.
During that two hour drive, as the sun came up, I looked at the burst of colors entering the world on the eastern horizon. It was the first of a lifetime of sunrises that I would see and Andy never would. I couldn’t even cry; I was in a state of panic; I just wasn’t ready to accept it yet. At 7:00 a.m. on that frigid December morning, I slowly rolled up in front of the house where Andy grew up and stared at the front door. I sat there, destroyed by grief and heartache, wondering why this had happened to my best friend, why he had been taken away from me. What was I supposed to do without him?
I pulled myself together, because what I was about to do was something that couldn’t be undone. I walked up to the door, just trying to keep one foot in front of the other, and lightly knocked. The door opened and two confused faces stared back at me with desperation in their eyes. I took one step into their house and proceeded to do the single most difficult thing I had ever done.
Drowning in sorrow, I struggled with the loss of my lifetime best friend. There was no way I was going back to a job that left me unfulfilled, a job I used to work alongside my now dead best friend. It just wasn’t going to happen. So, I quit my job and embarked on the entrepreneurial journey of a lifetime with Kristen by my side.
The rest of this story is about the roller-coaster ride I have been on ever since I left Corporate America after that fateful day…and I have never looked back. I have never again filled out a W-4, attended a four-hour meeting that I didn’t call, or asked human resources about the terms of the company benefits package. I have created my own bonuses, determined my own hours, and made my own destiny. The amount of blood, sweat, and tears is without measure. But the freedom, satisfaction, pride, and self-realization have made this roller-coaster ride worth far more than I could have imagined back when Andy and I dreamt of a life of playing more than we worked. Along the way, I have learned many lessons and discovered many principles that I wish I had known from the very beginning. Through story and example I know that you can take away from this tale something that you will find useful in your life, no matter what your goal or situation.
That is what this book is all about. I’m opening our journey of starting and running many small businesses, the highs and the lows, the struggles and the successes, so that you can not only be inspired to make this a decision of your own, but so that you can also have a book of lessons to guide you in accomplishing your dreams. Many of the stories and lessons to be shared with you here are marked with themes of hard work, perseverance, cultivating relationships, and constant innovation. But the end goal gives you all of the freedom in the world. You can live an uncommon lifestyle like the surfer dude, or like the one my wife and I enjoy now. After all, who doesn’t want to do less work but make more money? The advice we have to share comes from over fifteen years of starting more than five different businesses, and making more money every year than we did the year before. And for much of that time we only worked a few days a week or a few months out of the year!
Not everyone who enters the world of self- made business hopes for the same thing. Maybe you want to be your own boss for once. Maybe you are just reeling with great ideas. Maybe you want to spend more time taking trips to the ocean side than you do to the office coffee pot. Maybe climbing the corporate ladder, where you work seventy-hour weeks so you can drive a Mercedes that just sits in the company garage for those same seventy hours, has brought you to your wits’ end. Whatever it means for you to “have it all,” you will have by taking ownership over your business endeavors armed with our story of trials and successes. Do your goals reflect that you are personally ready to dive into your startup company? Do you know how to manifest everything you could possibly want for your business and your life? Would you like to do less work but have more money?