Stay on the Trail to Avoid Snakes and Swindlers


“Billy Diamond,” a 77-year-old cowboy, was our horseback riding guide during a recent family vacation to Arizona. A dust-covered white hat gave shade to his tanned leather face and squinting eyes. A guarded smile quickly yielded to a big toothy grin when he greeted us, “Howdy, Partners!” We hopped into his diesel “dually” pick-up truck for a short ride to the ranch where we signed the usual “you could die during this adventure, but you can’t sue us” liability-release forms. We then got all saddled up and ready to ride.  


Sharp Rocks: The sun was warm, and the air was fresh and cool. As we trotted along, my mind wandered and I imagined we were on a cattle drive. A shout from Billy brought me back to reality, “Stay on the trail!” I pulled on the reins to bring my horse’s nose out of a bush and back onto the trail. “The ‘beaten path’ is beaten for a reason,” Billy wryly added. “You’ll find rattlesnakes, badger holes, and sharp rocks off the trail. It is safer for you and the horse to stay on the trail.”  


Snake Oil:So, what do you do back in your world?” Billy asked. I told him I was a financial planner and, with a toothy grin of my own, let him know that he wasn’t the only one with a few decades of experience. He liked that, and then breaking routine, he shared a painful story that didn’t have anything to do with Indians, cattle or the Wild West. “My wife inherited $280,000 back in 2006. That was quite a windfall for us because ropin’ and ridin’ don’t pay much. We figured on turnin’ that money into somethin’ for our retirement. We met a fella who told us we could earn a bunch without any chance of losin’ money. It turned out to be a scam. My wife says it wasn’t my fault, but I stared at the ceilin’ every night for a whole year wishin’ I’d done somethin’ different. That snake oil salesman ended up in jail for five years. Good thing for him, too, ‘cause if I’d gotten my hands on him, I’da strangled him.”


A Faster Draw:What would you have done differently?” I had to ask. Billy leaned forward in his saddle, “I shoulda known you can’t make a lot without some amount of danger. I shoulda looked at more options and not put all the money in one thing. I shoulda checked the guy out before turnin’ all our money over to him. I shoulda stayed on the ‘beaten path’ myself. There ain’t nothin’ but swindlers, rustlers, and thieves off the trail. I know that now, but it don’t help much. So, I’m gonna keep ridin’ until the doctor or my body says to stop. Tell others not to make the same mistake that I did.”


Billy’s words made me think. Veering off the trail could be exciting, but there was also risk associated with that decision. Billy had veered off the trail and lost his wife’s inheritance as a result. Heed Billy’s warning and stay on the trail most traveled. The “beaten path” really is beaten for a reason.




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David D. Holland, a CERTIFIED FINANCIAL PLANNER™ practitioner, hosts a weekday radio show at 9AM on AM1380 Ormond Beach, AM1230 New Smyrna Beach and AM1490 Deland. He has also authored two books in his Confessions of a Financial Planner series. Holland offers investment advice through Holland Advisory Services, Inc., a registered investment adviser in Ormond Beach. He can be contacted at (386) 671-7526. Email your financial questions to