Coffee With A Stranger Cup 120 Roy H. Williams

Cup 120: Roy H. Williams – Advertising wizard, committed writer and collector of everything.

Coffee With A Stranger Cup 120 Roy H. Williams
Roy, coffee in hand, outside of the Chapel Dulcinea.

The Place: The Wizard Academy

The Cup: Regular old coffee (from one of those nifty pod machines) with a little half-and-half for me. The same, with vanilla creamer for Roy.

The Background: The ever-wise and knowing Coffee With A Stranger Cup 86 Ray Bard has talked about his friend Roy a handful of times as we’ve reconvened over the last two years. He gets brought up when we talk about advertising, marketing, writing interesting books, or when we’d chat about teaching methods that are outside of the box. Roy had become a mysterious figure to me, and the more time that went by and the more stories I heard, the more I became fascinated and wanted to meet the man under the cloak.

One day, a long while back, I asked Ray if he thought Roy would be up for having coffee with a stranger. At the time, I can recall getting a very non-answer answer. Something like, mumble, mumble…maybe…mumble, mumble. I dropped it, a bit disappointed. About three weeks ago, out of the clear blue sky, Ray sent me an email asking if I still wanted to interview Roy. Umm…YES! An email or two later, the coffee was set.

Unusual Start

Now having coffee with a wizard is bound to be anything but ordinary. So, it’s no shocker that my coffee with Roy was atypical, from the very start. First off, we skipped the usual coffee shop and met at The Wizard Academy. Which was perfect because part of my curiosity about Roy was related to this adult learning institution he’d created just south of Austin.

The Missing Cape

The next surprise was the lack of cape and cauldron. Admittedly, my wizard references are limited to “the man behind the curtain” in Oz and Gargamel (who you may remember from The Smurfs). Or maybe you didn’t spend the Saturday mornings of your childhood with a bowl of Corn Pops in your lap and your eyes glued to the screen to see what Papa Smurf, Lazy Smurf, Grouchy Smurf and the sensational Smurfette were up to. I can tell you what they were up to — avoiding or outsmarting Gargamel the Evil Wizard. When I laid eyes on Roy, he looked far more like an architect or a philosophy professor than the image of wizard I had in my mind’s eye.


Our first 90 minutes together was a series of surprises, or “Easter eggs” as Roy and his wife and business partner Pennie refer to them. There are well over 100 of these little magical delights hidden all over the campus. As Roy took me around and showed me several buildings, we talked history, literature, art and philosophy, and all the while he was pointing out little surprises. Or something would catch my eye and I’d have to stop him and ask questions.

I can promise that if you walked the campus 50 times, you’d see something new on each pass. And nothing is there by accident. The thoughtfulness and richness of the experience leave you with a palpable sense of wonder. I felt it in the form of goosebumps, at times. At others, a deep reverberation at my core. The place is new and full of curiosities, and yet oddly familiar. It’s a magical place, and because of that, this is one of the most challenging coffee conversations I have the task of sharing.

Truth of it is, I won’t be able to. Not completely, anyhow. If I had all the words and all the time, I could never sum up my experience with Roy, Pennie and Daniel (who is the Vice Chancellor at The Wizard Academy and the man who makes things happen. He also turns happy songs into sad ones (in a good way), is the host of the infamous Tour of Scotland (a favorite treat for students attending the Wizard Academy) and creator of Whiskey Marketing School). The experience of the academy can only happen first-hand. Mine won’t be the same as yours, and because I know some of you will actually read this and find your way there, I will not ruin the surprises by sharing what would be at best, a pale version of the real-life experience. It would be like me humming Purple Rain and expecting you to know what it would have been like to hear Prince perform it live. Not even close.

Roy and I did grab a couple minutes for a few of my standard questions at the end of our grand tour. So without further ado, let’s cover a few:

Common Grounds:

  1. What is the best gift you’ve ever been given? When I began collecting pocket watches, my father, by bizarre accident, opened a safe deposit box that belonged to his mother because she had just died. When he closed it, he felt something slide and hit the back of the box. He opened it again and it was his father’s pocket watch that he’d had when he fell over dead. He died when my dad was 13, so obviously I never met him. The reason it’s so special is because I am Roy H. Williams the 3rd. My son Rex is Roy H. Williams the 4th, our grandson is the 5th. That is the only connection I have to my grandfather (the original Roy H. Williams). So that is probably the most irreplaceable and the unexpected thing that I was ever given.
  2. What’s your motto? Just shut up and do it. I say that to business owners all the time.  
  3. What is the most obscure food you’ve ever eaten? Raccoon. When I was in the steel shop, a guy named Harold shot a raccoon and smoked it. So this smoked raccoon carcass was in the refrigerator and Harold said that anybody that wanted to come and grab a chunk of that raccoon meat could. So the way the raccoon was smoked it would just kind of tear off. So you’d just tear off a strip and go eat while you were working in the steel shop. That’s pretty obscure, isn’t it? {Umm, yes Roy. Definitely obscure!}
  4. What book should be required reading for all humans? My answer to that would change on different days. But I’d say The Poetry of Robert Frost should be required reading. It’s all of his poems in a single volume.
  5. What is something beautiful that you see everyday? My wife. {Pennie is sitting nearby and adds, “That’s because I’m sitting right here.”} To which Roy replies, “I said it in spite of the fact that you’re sitting right here.”
  6. How did you make your first buck? I was 13 and began working in a metal fabrication shop and kept that job until I was 18. I was working 35-40 hours a week while I was in high school. That’s the job I had when I got married. Pennie and I got married at 18. We went to the Sweetheart Banquet at 14. Went to Prom at 18. She had a scholarship to one college. I had a scholarship to another college. I went a day and a half and I said, nah, this isn’t working out for me. {I clarified, “Because you didn’t like the college or because you missed Pennie?”} Because I missed Pennie. So I said to Pennie, ‘Here’s the deal. Why don’t you drop out of college and we’ll get married?’ And she said,  ‘We’re young and poor. Why don’t we wait a couple years?’ So I said, ‘In a couple of years we’re still going to be young and poor.’ She thought that was a good point, so she dropped out of college and we got married.
  7. What smell makes you happy? Vanilla. 
  8. What’s a food you can’t live without? Eggs. Eggs are my primary source of protein. I would eat eggs at every meal if restaurants would simply serve them.
  9. What’s your guilty pleasure? Guilt is not a thing I am familiar with. Let me put it this way — there are many, many, many things I ought to feel guilty about, but I don’t. I have no sense of shame. I would say that the thing I do, that most people would find most difficult to endorse, is I collect more things than make any sense. I have warehouses full of things. Paintings, furnishings, and things. All the stuff you see around here, including that staircase right there, Pennie and I found — typically at auctions. A number of things that we purchase we don’t need right now, but years from now, we’re going to need it. The key is you buy it when you find it. When you find it, you never have a use for it right away. But if you hang onto it, in 7, 10, 15 years you’ll be glad you have it.

Back Home

Roy grew up just outside of Tulsa, OK. He met the love of his life when they were just kids and after nearly 40 years of marriage, two sons and two grandsons (so far), the pair continue to relish the daily adventure of life together. The most significant thing that’s happened in the last 30 days, Roy tells me, is that the number of grandchildren is increasing 33.3% and after all boys, they just learned that for the first time, the family will have a little Princess. As for other significant events that lie ahead, Roy and Pennie are also looking forward to their youngest son getting married in May.

I love hearing how people wind up in Austin, and for Roy and Pennie, the answer is similar to many of us who chose this wonderful place. Roy said, “Austin, at that time, was about the same size as Tulsa, but had a much prettier river and much better restaurants. In our business, with clients everywhere, we can live anywhere. So we moved here on purpose in 1987.” They moved first to Buda, then in 1990 to Austin and in 2004 the Wizard Academy was opened.

Hearts and Minds

Roy’s primary business is Wizard of Ads, where he has 45 partners/branch offices and hundreds of clients all over the world. Roy has a special gift when it comes to understanding people and creating advertising that speaks to them in an authentic voice. It’s this gift that started the business and also the series of Wizard of Ads books he’s written. If you want a sampling of what Roy offers and how he thinks, I highly recommend signing up for his Monday Morning Memo. It’s an email…I suppose. But, like all things Roy, it’s also an adventure full of rabbit holes and nuggets to challenge your thinking. Good stuff.

Something I was surprised to learn about the academy was that just shy of 1000 weddings happened there last year. WHOA! The Chapel Dulcinea is a special place and if you are so inclined, you are welcome to get married there, for free! Curious about the name?  Dulcinea is, according to Don Quixote, the most beautiful woman on earth. Check out this page to learn more.

More or Less

I wonder what Roy wants less of in his life. He tells me it’s bureaucracy.  I ask if he faces it a lot and he says, “It seems like I do. Government regulatory things seem endless when you have a non-profit or a license to serve alcohol or because we have five corporations and we’re constantly being audited either by sales tax people or income tax people. Also, water usage because we’re in Hays County. Legal compliance forces you into a world of non-stop bureaucracy. I’m not saying it’s not necessary. I think it’s probably necessary and it’s probably good. I just wish I had less of it.”

How about something he wishes he had more of? Roy immediately responds, “Free time. There are very few windows of time where we even have a few hours where we can do whatever we want. It’s shockingly rare.”

I go a little deeper with the question, offering a bit of a different angle. I ask Roy to imagine he’s 80 years old and to complete this sentence: I wish I had spent more time on… He says, “Writing.”

How about the sentence, I wish I had spent less time on…? Roy says, “That’s a hard one. Because I don’t make myself do things I really don’t want to do.  I’ve chosen to do everything we’re doing. I did it willingly and by choice. The problem isn’t that there are things I wish I didn’t have to do. The problem is there’s not enough hours in the day. So you just run out of time. The things I really, really wish I didn’t have to do, I usually don’t do. I have to be involved, but it’s a minimal amount. I just wish there was less of it.”

That’s interesting and gets me wondering if anyone ever says, at the end of their life, “I spent my time doing only the things I wanted to do. I didn’t get the to bottom of the endless list, but I did the things I loved and put checkmarks next to the things that mattered most.” As I look over my calendar of the last month, I can say I’m doing better than I have in years past. And still, I have some work to do.

God Talk

What does Roy believe that everyone else thinks is crazy? He tells me, “I believe in a personal God and that Jesus was, in fact, who he said he was. And that is shockingly rare these days. I’m not what you’d think of as the Christian Right. As a matter of fact I detest the Christian Right. Christians involved in politics or Republicans masquerading as Christians, or Christians who confuse patriotism with Jesus really piss me off. Like very few things in life piss me off. People are shocked, number one, that I’m a believer, and number two, that I’m as traditional as I am in my faith. I think the church in America, the church in the West, got derailed when they started teaching Christianity instead of teaching Christ. When they decided to mix faith with politics, which Jesus said explicitly not to do. And yet people sign God’s name to checks God didn’t write. And when you say you speak on behalf of God, that really pisses me off.”


Something Roy says he is ridiculously good at is writing. He tells me, “I am a shockingly good writer. Embarrassingly good. And I say that with the most profound humility. I get up at 3:30am and I write until about 8:30 or 9 every day, seven days a week. So I spend about six hours a day, seven days a week, and that’s before I start writing for clients. I probably write 30 or more hours a week.”

I want to know how Roy celebrates. He tells me, “By staying home. Pennie and I say that people who love to travel, just haven’t done enough of it yet. When you have travelled as many weeks of your life as I have had to, being at home is the great celebration. A favorite part of the day for Pennie and I, just about the time the sun comes up, we go sit on the back porch and talk for a while. Watch the birds in the bird feeder and the squirrels, doing squirrel things.”

A daily habit Roy believes contributes to his overall success and well-being has to do with letting go. He says, “I steal time for myself and I do it very well. Whenever there is more to be done than can possibly be done, and I could be breathlessly frantic all day, I choose never to do that. I will stop and say, ‘Screw it.’ And my phrase is, though I don’t say it aloud, ‘Let planets collide; let millions die. I’m done.’ Regardless of what the consequences are, I’m stopping. I’m going to go eat lunch, I’m going to go drink a glass of wine, I’m going to go watch that thing right there. Consequently, I’ve always been able to fall asleep easily. When I go home, it takes me about 10 minutes to forget what I do for a living. It’s something I wish I could give to Pennie. I can just unplug — no worries. Most people, at the end of the day, review the events of the day. And in so doing, they rehearse their problems and their anxieties, and all the unfinished tasks. Like picking up a meat cleaver, I can say, ‘I’m done’ and then pick it up tomorrow. I’ve often wished I could give the skill to people.”

Love Is Thicker Than Blood

The life that had the greatest impact on Roy was Pennie’s father. Roy explains, “Because my dad was absent, I never really had a stable male figure in my life until Pennie and I started dating. He was very much a surrogate dad to me. He was a really, really, really great man. Pennie has three older sisters and two of them will be celebrating their 50th wedding anniversary this year, one will be celebrating 42 years this year and we’ll celebrate 40 years. All four daughters still married to their original husbands. And all four daughters work with their husbands. Pennie’s family had such a good sense of what family is. Of all the people who’ve had an impact on me, I’d say Paul Compton had the most. My oldest son Rex lucked out with a similar kind of a father-in-law.”

The Unexpected

If Roy had just 30 seconds to make a speech to the world his message, he says, would be on the dangers of predictability. Roy says, “I’ve heard this before, but not enough people repeat it: ‘Traditional wisdom is usually more tradition than wisdom.’ And that idea of predictability and orthodoxy — it’s almost always a mistake. Like with music..what’s the very, very last thing a person would expect to hear in this song? And how can we make that fit? Whenever you do the new, the surprising and the different, you gain attention, you hold attention and you do that whether you are a painter, a sculptor, a writer, a singer, or a retailer. It has been the mark of every innovator who left their fingerprints on the world. Doing something completely different from what people expect. If you say what people expect you to say, they’re bored. If you do what people expect, they’re bored. The only way to hold someone’s interest is to do and say something other than what they expected.”

My day with the Wizard (and guests) at the spectacular Wizard Academy was anything but expected. As I already explained, it was nothing like what I imagined it would be. Roy was less wizard and cape and more dude in jeans and a button-down shirt. The Academy was less learning institution and more place of wonder and delight. My day here was many, many things. Expected was not one of them!

Did I go overboard with my description of the day and the experience with Roy at the Wizard Academy? If I were you I’d assume so. But since I’m me, and I was there, I will promise you this special place requires no exaggeration. It’s love, and devotion, and mystery, and inspiration, and joy, and community, and solitude and whimsy, and whisky, and wine…all bottled up and served in your favorite glass with the warm sun shining on your bare shoulders and making you feel alive. So go. If you get the chance, just go.

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