February 2, 2015

Long before I could drive, I had a fascination with road maps. Growing up in the 1960s, the maps changed every year as the Interstate Highway System expanded across the country. I would study the lines and dots and merely wonder what towns like Pittsfield, Massachusetts even looked like. My mother would look at me quizzically as I suggested a Sunday drive to some otherwise ordinary place, but I just wanted to see it for myself.

Roadside grew out of that fascination. I cared less about the big tourist attractions and more about what made the nation tick at its most basic level. In the Cliff Notes version of its history, I launched it in 1990, and then I sold the debt-laden enterprise to Ball Publishing in 2000.

For the first six months of that year, I listened to the new management tell me I was wrong about everything. I spent the next six months proving that I was right about everything.

In those first six months, I watched in wrenching agony as Ball Publishing staffers mangled the concept. After regaining control, I enjoyed the next six months in near-ecstacy as I retook the reigns, publishing our single, beautiful glossy version. It was the greatest year of my life.

With 25,000 copies of this issue just off the press, with the ink barely dry, George Ball pulled the plug on the project, firing everyone except me. My contract initially saved me, but the 20,000 new subscribers we gained never saw a copy.

Three months later, he trumped up a reason to fire me as well — breaking my contract that still owed me $40,000. Ten years gathering momentum, good will, and personal achievement evaporated.

Maybe I should have sent up an S.O.S., made a bigger deal of it and more publicly appealed for help, but I had confidence that the concept would prevail and my Hollywood ending would come.

Copyright law allowed me to take Roadside back in 2003, but it didn’t give me any budget. I tried to start again with every resource at my disposal. I drafted and redrafted a business plan, changing it every year as the technology evolved. I talked it up to anyone who would listen.

Ball Publishing had budgeted $7 million. My new plan budgeted “only” $1 million, but Don Levy at the Deluxe Town Diner told me straight up, “No one’s going to invest a million dollars in your magazine.” He did suggest that I print up a million copies and include it as an insert in the Sunday New York Times. “Care to help me pay for that?” I asked. He declined.

I held a brainstorming session with close friends to generate ideas for a relaunch, and one of the attendees went home and a month later launched a site featuring most of the ideas we discussed. Why couldn’t we collaborate instead? “It was just something I wanted to do,” he replied.

Then I partnered with a another friend who proposed a consulting business idea that would eventually include a relaunched magazine. Our partnership dissolved in acrimony when he opted to take the business in a direction different than our original plans.

I redrafted the business plan yet again in 2007, honing the budget down to $500,000, focusing even more on new digital media. In the meantime, with blogging now the latest thing, I reached out to kindred spirits to join me in this effort to popularize the American roadside by collaborating Huff Post style. Keep your content, I proposed, but let’s feature it in one place. More eyeballs coming to a single source meant that we could reach traffic levels that might actually pay us something.

My hopes that the “roadside community” would eagerly jump on board proved a fantasy. Wasn’t our collective goal to help popularize these places that we love so much, keeping them viable? That was always my agenda.

The vast majority of blogs paid its authors nada because individual efforts rarely drew enough traffic to generate any quantifiable ad revenue much less garner any real influence. Clustered in one place, the combined entity would become the authoritative source of this information.

Former Roadside contributors who had already launched their own blogs read only by their tiny cliques turned me down without explanation. Some of the new bloggers I recruited made valiant efforts, but most either lost interest too soon or scoffed at the initial checks they earned by the traffic they generated — cash they wouldn’t receive otherwise. One blogger got a call from the Boston Globe but shrugged it off.

The demands of family life meant that I could not pursue this as I did in the beginning. I finally tapped out my network in search of funds to relaunch. Since I could not afford to bootstrap it again, I put Roadside on the back burner, concentrating most of my efforts on the Diner Finder. After more than 20 years nurturing this idea and generating volumes of content, the Diner Finder remained a uniquely authoritative listing. No one else had anything close to it. Perhaps I could use it as the kernel of a revival.

In 2012, a good friend of the magazine and one with solid restaurant credentials urged me to redraft the plan yet one more time. I said to him, “I’m happy to do it, but only if you can assure me that we’ll have a place to pitch it.” He told me not to worry. Hours of what seemed like fruitful, illuminating discussions ultimately went nowhere, because there was, in fact, no place to pitch.

Finally, in that same year, another good friend of the magazine, a subscriber since the early days and one with entrepreneurial experience suggested we build a Diner Finder app. He’d put up the cash and I’d put up the content. I saw this app as the natural evolution of Roadside and could see it growing into something big. He had a developer in mind that would turn this around for us in maybe four months. Thirty months and four developers later, still no app. At least we didn’t have any competition, right?

That changed too. Very recently, a new app and enterprise launched with $2 million in funding that currently has about 40 employees, and is busy “databasing” America’s roadside attractions. They came out of nowhere with connections that saw the value in the idea I always knew was there. They have implemented features in their app and on their website that I first proposed fifteen years ago. From what I can tell, they have a quality database, and it promises to get better.

This, of course, is not a new story in the history of American enterprise, and I accept that and wish them luck. But I would be lying if I told you I wasn’t profoundly disappointed. In retrospect, I should have abandoned this thing right after Ball shut it down and moved on, but I found the potential too compelling. George Ball left money on the table and 20,000 new subscribers in the lurch.

Google my name, and one of the first hits is a posting from 2004(!) on Roadfood stating, “Is this guy angry with the world, or what?” I would challenge anyone sitting in my booth not to feel that anger, except that mine comes from my inability to accept we have done to our landscape, and at those who dismiss the underlying issues that cause the decay and destruction of our culture. This is not a frivolous matter, and I never saw it as such.

And finally, I am angry at someone who promises to help a hopeful man make his dream come true, and then crush that dream for no good reason whatsoever — and taunt him about it years later. Just over a year ago, George Ball sends me an email calling me “human waste” and not worth “a bag of wet extremely rotten potatoes.” There is no circle of Hell torturous enough for such a beast.

What’s next? Beats me, but what would you do? You have mouths to feed and a mortgage to pay. You bet your whole career on an idea that promised to change everything, but you now watch from the bleachers as someone else hits it out of the park.

No one can say I didn’t try my best, but the Hollywood ending only happens in Hollywood. Twenty-five years is more than you can ask of anyone to carry the torch. This is the fire going out.