Live Historic: The Start-Up Adventure Starts To Get Real

If the National Association of Realtors has re-sold America on the joys of homeownership after a brutal real estate recession someone still needs to sell us on the joys of moving. For the past three weeks we’ve been living in day-to-day contingency limbo surrounded by three tons of life in U-Haul boxes. We’re scheduled to close in ten days and have been eating take-out for a week so we don’t get our stove dirty.

For those of you who have been following our Live Historic adventure so far in our recent Live Historic blogs, selling our current historic house is the first big step of our journey. Buying a vintage Airstream comes next, followed by a four month architect-inspired, nautically-crafted renovation. We’re hitting the road this winter no matter what.

If this all sounds simple, it’s not.

Contrary to everything you were told when you were young—that you could do anything you want when you grow up—being a dreamer isn’t natural for most of us. We all realize sooner than later that we’re not athletic enough to be a professional hockey goalie (like I wanted to be). In high school everyone eventually specializes in something; I knew by 10th grade I was never going to be a mathematician. Then you wake up two decades later and find yourself doing something for a living that you never even knew existed when you were young. Dreams don’t come with implementation manuals for adults either—and therein lies the most precarious part. Even if you remember how to dream about re-inventing yourself no one can tell you how to get you there.

Dreaming big in your 40s is one of the biggest gambles of all. Right when you’re supposed to be hitting your prime earning potential you tell your friends and family that you’re getting your mid-life crisis over with early and taking your new online business on the road in a 28’, satellite-connected (and very tricked-out) aluminum tube. Most dreams fall apart not because they aren’t inspiring enough or they are too expensive to justify. They are slowly blood-letted by too many people telling you that you’re crazy to ruin your life.

I’ve learned from experience that dreams are worth all of the hype—and the doubt—when they finally start becoming real. Little things begin to matter because they build momentum. Outlandish ideas validate themselves out of nowhere. And then all of sudden, when all of the fairy dust you’ve been selling for months actually looks possible, the people who were thrilled to tell you that you’re ruining your life somehow find your story inspiring. Our Live Historic adventure finally feels like timing is on its side.

Dreams—or more accurately the implementation of them—are also complicated, brutally practical, and often expensive. In the case of our Live Historic Airstream renovation, it requires architects, interior designers, yacht builders, boatyards, and big checks. Since we’re planning on running our start-up business full-time from the road it also requires big data wireless internet capability 24/7 in places that are fifty miles from the last analog cell tower. That’s another big check. Fortunately for my wife that means we’ll be able to stream the Real House Wives from any campground in North America as well.

And by putting this whole cross-country Airstream circus on television with our two dogs, we’re now putting a film crew in tow. Be careful what you dream for. It could get hilarious. Stay tuned for more updates to come next week since things are breaking fast but here are the juiciest details to date:

1.     The Television Series: The most exciting news always comes first. We’ve signed our television development deal with one of Manhattan’s most respected production companies, Silent Crow Arts, who has had its hands in award-winning reality shows like ‘Deadliest Catch’ and ‘Storage Wars’ for more then a decade. I’ve always joked that I’m going to pimp my wife and dogs out for television. Reality television has finally caught up with me. We’re shooting pitch footage next month.

2.     The Airstream: Our vintage Airstream renovation is two months away from starting and we’re already shopping. The even better news is that 2015 HGTV Dream Home and award-winning architect Patrick Ahearn has agreed to design our Live Historic Airstream and guide its careful renovation including numerous tricks we’re adapting from the custom yacht world. How could we run this whole enterprise on the road with two dogs without a built-in vacuum cleaner, a washer and dryer, and 24/7 satellite communications? Not coincidentally, Campbell’s Boatyards from Oxford, Maryland, one of the Eastern Shore’s premiere custom yacht builders, will be doing all of the renovation work under Ahearn’s direction (and my wife’s control). More on Patrick Ahearn and Campbell’s coming shortly

3.     The Plan: I realized that the Live Historic dream is becoming real when I asked my wife two nights ago where she wants to spend the winter. If there’s an undiscovered corner in America or untold story we’re on a mission to find it, photograph it, and tell it over the next year—and hopefully do so at the axis of where it’s always 75 degrees and sunny every day. We’re starting to map out our preliminary itinerary together but here are a few teasers: urban exploration in one of the country’s oldest cities, Low Country hospitality/the desert high-life, private islands and Hollywood mansions, and one of America’s most historic communes

4.     The Relationship: Remember when I said none of this is easy? Case in point: To make this dream happen, we are selling our 2400 square foot historic home and downsizing to our 1100 square foot Gothic Revival brick cottage on Maryland’s Eastern Shore. That’s the same amount of people, dogs, and stuff in half the space. In my mind it’s an Airstream practice round for all of us. In six months, we’ll be living in 600 square feet of mobile Airstream chic. That’s the same amount of people (and dogs) in half the space yet again.

We’re already wondering how many marriages—that also includes working together full-time—have survived this before? But that’s for an upcoming blog.

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