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Illustration of the Month: How To Play the Winner’s Game
I’m obsessed with tennis. It’s mostly a healthy obsession, but this time of year, I start to slip. Why? Wimbledon, the finest tennis tournament in the world, is about to begin. It’s steeped in tradition, and yet its host, the All England Lawn and Tennis Club, isn’t afraid of innovation and science.
Whenever there’s a way to combine statistical analysis, tennis, and investing, I’m all over it. That’s why my life was transformed nearly 20 years ago, when Larry Swedroe did exactly that in the brilliant introduction to his first book (emphasis mine):
“After making what I thought was a great shot, a forehand that landed right in the backhand corner of my opponent, my teaching pro said, ‘That shot will be your worst enemy.’ While it was an exceptional shot, he explained, it was not a high percentage shot for a good ‘weekend player.’ Remembering how good that shot felt, I would try to repeat it. Unfortunately, I would be successful on a very infrequent basis. The pro asked me if I wanted to make great shots or would I rather win matches? (I thought that one was the cause of the other.)”
Playing the winner’s game is what the pro was getting at as he cautioned Larry about falling in love with his special and rare shot. Winning calls for consistent and disciplined play. When players go for shots beyond their skills, they’re playing a loser’s game. This decades-old analogy goes back to a book by Dr. Simon Ramo, Extraordinary Tennis for the Ordinary Player.
With this background, you’ll know why the following ad is so meaningful to our firm. As a minor sponsor for the April 2018 Men’s Clay Court Championship, Hill Investment Group was proud to support an event that has been in play for more than a century – and held near our Houston office since 2001. As our sponsorship ad expressed, we enjoy helping investors play a winning game, by embracing a “long view” game plan.

No Pain = No Pain
While the more familiar expression, “no pain, no gain,” may apply to many parts of life (such as my first half-marathon), sometimes pain is just pain, with no gain in sight. When that’s the case, shouldn’t you do something to avoid it?
That’s the point of a recent video produced by our friends at Dimensional Fund Advisors, “Tuning out the noise.” The first minute is admittedly stressful; it evokes the angst many investors feel when they try to navigate nerve-wracking markets on their own. Bear with it though, because you have much to gain from the video’s message: By showing investors how to Take the Long View® with their investments, our aim is to help people tune out the pointless pain, look past the daily fray, and get on with investing toward their lifetime goals.

Check out the video for yourself. Or, if you prefer to read rather than watch, here’s an article Dimensional produced along the same theme. Last but not least, if you could use some rational advice to cut through the clamor, we’re here to listen.
Who Built HIG’s Hill?
When Rick Hill and I founded Hill Investment Group in 2005, we knew we wanted to do something very different from anything you’d find in the traditional financial services landscape. As we set about converting our ideals into reality, we referred to our culture as an island of idealism, rising above the status quo.
Knowing little about branding, we surveyed several St. Louis influencers to help us find a firm to create our logo and tagline. Rick also had one request: He was hoping the firm could include his name.
In the winter of 2005, we selected TOKY Branding + Design to help us with this challenge; we are still their clients to this day.
In hindsight, the rest may seem like a no-brainer. Because they all work so well together, it’s easy to assume that our firm name Hill Investment Group; our hill-shaped logo, our Take the Long View® tagline; and the professional, polished line drawings that now characterize our graphic presentations came together practically overnight.
You’d be mistaken. And we’d be doing a disservice to the visionary souls who have put in countless hours and creative capital helping us shape and refine our now “obvious” brand.
Usually these marketing types labor on unsung behind the scenes, so we thought you might enjoy meeting one of the incredibly talented teams behind our branding: TOKY Branding + Design.

We love how Eric Thoelke and his TOKY team took Rick’s name and helped us connect it with our greater ideals, guiding us on how to meld our identity with our desire to coach people on how to take a higher perspective with their wealth. In his own words, here are Eric’s thoughts about our collaboration (and, yes, Eric’s last name is pronounced the same as his firm’s simpler spelling of the same: toe-kee):
“Back in 2005, I got to spend a couple of leisurely lunches with Rick and Matt, talking about their nascent business, and how their investment philosophy and deeply personal service would set them apart. It was immediately obvious these were true differences, not just distinctions in style. Our goal was finding a way to articulate those differences by integrating the firm’s name, logo and positioning.
The best brands encircle a target audience with messages that are meaningful and distinctive. It’s like pointing all the engines on a rocket in the same direction; alignment creates the greatest thrust. In working with Hill Investment Group, I never get tired of the rush that fires up all their branding engines and targets them in the same direction.”