superold

So it’s come down to this. Either I turn my startup site into a successful business, or I’ll wind up working as a Wal-Mart greeter in my 70s or 80s.

That’s only a slight exaggeration. I’m 63, and it turns out my decades of media and journalistic experience are nearly worthless. My pay-the-rent job consists of relentlessly cranking out articles — 1,266 and counting over the past few years — for Demand Media, the oft-maligned content farm. I’ve written pieces like “What to Do When You Stink at Tennis,” “Is Impotence Grounds for Divorce?” and “List of Kriya Yoga Gurus.” I earn $30 an article, which roughly translates to minimum wage.

So it’s time — pretty late in the game, actually — to do what every startup founder wants to do. My dream is to create a successful business, have fun along the way, make tons of money then do whatever I want. Maybe write a few books, live near the beach in San Diego where I can jump on a stand-up paddleboard as the sun sinks toward the horizon, travel, and create an institute for investigative journalism.

Of course, I know how far-fetched that sounds. I wasn’t born yesterday — in fact, when I was a kid, our black-and-white TV could only pick up three stations, and the Internet was a figment of the imagination. I realize the odds of creating a successful startup are long.

In fact, my editor at Pando asked, “Are you crazy?”

Probably.

Nevertheless, starting a media company is, for me, a logical progression. In the past I put together three media properties: a magazine, newsletter, and book.

The trade magazine I edited in Portland, The Oregon Horse, covered the thoroughbred racing and breeding industry in the state. Despite a miniscule budget, we won a couple of national awards for writing and design work.

It grew out of the same Seattle studio that housed The Rocket, a now legendary monthly that focused on the Northwest music scene as well as movies, pop culture, and politics. I covered the 1984 Presidential campaign for The Rocket, writing about Ronald Reagan, Walter Mondale, Gary Hart, and Jesse Jackson.

The talent level was off the charts. Susan Orlean, a New Yorker staff writer who wrote “The Orchid Thief,” which inspired the movie “Adaptation” (Meryl Streep played Orlean) wrote for The Rocket. She also published a story for The Oregon Horse, something she probably doesn’t list among her writing credits. We gave her $100 to play the ponies one day at Portland Meadows and she turned in a wry and funny piece.

Later I published and edited “The Fanatic Reader: Your Guide to the Best of Popular Magazines.” A collection of about 20 volunteers in Seattle and Portland read and recommended magazine articles from more than 100 publications. Our subscribers included a professor in Tokyo and an executive at Amblin Entertainment, the production company of Steven Spielberg. Our cartoonist was Matt Groening. I bought reprints of his rabbit-hopping strip, “Life in Hell,” from his wife for $25 apiece and put them on the back cover. Shortly thereafter Groening created “The Simpsons” and finances were no longer a concern for them.

Unfortunately, my business plan for The Fanatic Reader consisted mainly of a hope and a prayer. The newsletter folded after a year.

In 2000, a few years after traveling with the women’s golf tour for a season and writing a book about the LPGA called “Tee Times: On the Road With the Women’s Professional Golf Tour,” I came up with the basic idea for another publishing venture. It stemmed from my hearing about Stuart Skorman, who met my cousin at the poker tables in San Jose. He had just sold his startup, Reel.com, to Hollywood Video for $100 million, pocketing $20 million.

So I started thinking about what I could do. One day, while walking around my neighborhood in Carlsbad, just north of San Diego, I realized that The Fanatic Reader could be expanded into a giant-sized consumer guide. Instead of recommending magazine articles, we could recommend the good stuff in every category we could think of.

To my surprise, I didn’t come across any sites like it.

Then life intervened.

I became very sick for a few years, suffering from a bizarre illness that was caused by taking way too much of an herbal remedy that I thought was harmless. I moved to Phoenix to live with my father. By the time I began to feel better, his health started to deteriorate. So I stuck around. Eventually he underwent quintuple bypass open-heart surgery at the age of 81. He got back on his feet but was frail and his last two years were difficult.

As any caregiver knows, those years weren’t easy for me either. I was close to my dad, however, and eternally grateful I was around to help.

Then I wandered somewhat aimlessly for several years, trying and failing to sell a book proposal on the promise and peril of alternative medicine. During this time I made a not-so-shocking discovery.

Poverty sucks. And it sucks even more as you get older.

Mine is a lower-middle class type of poverty. I live in an okay apartment in Nevada City, belong to the neighborhood gym, which keeps me somewhat sane. Nevada City, nestled in the foothills of the Sierras between Sacramento and Reno, is a quaint, peaceful, friendly tourist town, a relatively easy place to bunk down.

But I obsess over money and finances. I have no furniture in my living room. Finding a decent-but-cheap can opener — manual, not electric — required prowling local thrift stores for a month. Spending $10 on dinner? Out of the question.

I live from $30 article to $30 article, sweating bullets when a Demand Media copy editor demands a rewrite or rejects an article altogether. Bye-bye grocery money.

Worn down by all this, I returned to my curation-aggregator site idea in 2011, hoping it might, at long last, be my ticket to financial salvation.

I’ll talk about that in my next post, which will publish next Saturday.