Chapter 1

1. Eyes on the Prize

If I knew anything about it back when I was selling my first business, I would have been an original EXITpreneur. I could have known myself better, set my business up for the next owner, and watched for the right time to sell—both from a market standpoint and my own interest level. I would have moved on earlier, instead of holding the company back when the next steps fell outside of my comfort zone. But I thought I was just an entrepreneur, and I thought that entrepreneurs were supposed to hold onto their creations until the bitter end.

Owning a business was my inevitable path in life. I had the childhood many business owners can relate to—mowing lawns and running paper routes and finding ways to make some extra cash wherever I could. I was always working on something bigger, too, like the worm farm my dad let me set up in the basement in junior high. Since we lived on one of the central streets in our town in Maine, a “Nightcrawlers for Sale” sign out front brought fishermen knocking on the door looking for bait. I’d bag them up, then go out with a flashlight at night to find more to replenish my stash. My muddy grasp on supply and demand opportunities started young and never left me alone.

I did attempt to take other routes. During my undergrad at Northeastern University, I participated in a co-op program that split the year’s work between school and on-the-job experience. For the first nine months, I tried my hand at corporate life. I can’t lie—I felt like a big shot with my secondhand-store suit and briefcase filled only with lunch. But as soon as I realized I was just a cog in a wheel, I was done. It was going to take more than the allure of money to hold my interest.

For a little while, working as an assistant manager for an upstart fast food franchise scratched the itch.1 When the twenty-something-year-old who hired me asked, “Do you like beer?” during the interview, I was immediately hooked on small business life. The corporate world this was not. We worked hard and played hard, and that was all there was to it. I loved it for what it was, and kept my eyes open for what might be next. That opportunity looked like a guy named Michael Hackel, wearing a beat-up leather jacket, jeans, and an Oxford dress shirt and carrying an old leather briefcase, hoping to get our restaurant on board with his restaurant delivery service.

The idea was simple, but for a Cajun fast food restaurant in the late ’80s, it was revolutionary: customers wanted food delivered, and restaurants weren’t doing it. Michael’s company—DiningIn—would keep menus for any of their participating restaurants, take the order over the phone, fax the order to the restaurant, then pick up and deliver the food. After Michael made his sales pitch and left, I told the co-owner I wanted in. More specifically, I told him I wanted to do it myself. The entrepreneur in me couldn’t resist a good opportunity. He thought it was a smart enough idea and offered some backing if I wanted to give it a shot. We shook hands and became fifty-fifty partners on the spot.

Michael’s model had been carefully built, modified, and branded for high-end restaurants—all of his drivers wore tuxedos and made it feel like “dining in” a fancy restaurant.

Mine was named during a brainstorming session with a roommate, another roommate’s girlfriend, and the assistance of a smokable herb that is now legal in most states in the US. We came up with “The Wrong Number,” because how funny would it be to answer the phone and say “wrong number” when it wasn’t wrong? (I know—not so bright.)

Needless to say, we weren’t going to encroach on Michael’s high-end market. We stuck to the foods that college kids wanted delivered, and within a week I had five restaurants on board. Why? There was a real need for the service, and it removed all of the pain points for the restaurant owners. I also hustled and just knew the idea made sense. Even with a dumb name.

I launched The Wrong Number while maintaining my full-time student status at Northeastern. I worked eight to ten hours a night, seven nights a week, for months, and somehow didn’t let my grades suffer. It was a blast.

Clearly, between the name and the workload, I wasn’t thinking about the eventual exit. I kept the business going for nearly six months, then quit after Christmas break. I quickly learned that lifestyle is important to me, and I had no intention of working that much for however many years it would take to make The Wrong Number worthwhile.

Not too long after closing up shop I applied for and became a driver for DiningIn. I was still a kid, a student, and an eventual entrepreneur. I made more money as a driver than as an owner. But I knew I’d still run my own business someday.

After I graduated and moved on, I watched from a distance and learned as Michael grew the business, invested in technology, expanded to other cities, and eventually exited well to a company that we would all come to know and love—Grubhub.

In the years that followed, I kicked around in the corporate world again, played with a couple of business ideas, and even tried to be a brick-and-mortar business broker for a little while. Each new venture taught me a little more about what I did and didn’t want. None of them felt quite right and it was great to narrow things down by process of elimination.

On a cold Saturday in January of 1994, I finally hit it off with another interviewer who was young, hip, and pretty casual. It was a Saturday—moving day for the company—and the person who hired me was wearing sweats! I had my ten-cent suit on, bought at the Buffalo Exchange in San Francisco a few months back, and I became employee number thirty-four.

I loved the small-but-rapidly-growing entrepreneurial atmosphere at that company. As we grew from $17 million in revenue in 1994 to $101 million in 1997, my role was always changing, from sales rep to manager to media buyer. But the more the company grew, the more restrictive the environment became. I stayed until the company fully outgrew me, which, to be completely transparent, looked like me trying to resign but getting let go instead, complete with the head of HR escorting me out the door.

This was exactly what I needed. Within a few weeks, I had opened my own radio-based direct response media-buying agency. I was finally settling in as an entrepreneur, where it seemed I was always going to be. However, just like in college, I worked forty-plus hours a week as a sales rep for a call center nights and weekends while launching and building my media-buying business during the day.

Over the next fifteen years, there were plenty of ups and downs and lessons to be learned—some of which I’ll cover in the next chapter, and some of which can only properly be told over a beer. The bottom line is that I survived, thrived, and evolved. My business morphed from traditional media buying to launching my own brands on radio and television, producing two TV infomercials, co-hosting one, and ultimately moving to a 100 percent online business model in 2005.

I ran my e-commerce business through the best and worst of the economy. And I emerged on the other side—more tired than victorious. In 2010, I woke up one morning and decided I would sell. No planning, no prep work. I was bored, I was done, and I wanted out right then.

Years later, when refining the EXITpreneur process, I realized we had to differentiate between deciding to sell a business and planning to sell it. Because far too many people decide to sell like I did, when a plan could have ensured their success.

An EXITpreneur doesn’t have to set a timeframe when, ready or not, it’s time to sell. But most entrepreneurs will eventually want out one day, whether or not the business is ready. Planning for that day from the start (or from wherever you are in this moment) can set you up for fewer headaches and a greater chance at success.

Planning to exit is about realistic expectations. It’s knowing that the time will come to move on, even if you don’t know exactly when that will happen. It’s creating the underlying structure that allows you to sell then, instead of waiting until you’re emotionally spent. By that point, the window to exit well has probably closed.

My exit from my e-commerce business was years too late. The signs had all been there. Well before the financial crisis hit, I had emotionally checked out. I wasn’t interested in the details anymore, and my disconnect began to take its toll. Had I planned then—better yet, trained and gained knowledge from the beginning—I...