Cup 27: Clint Greenleaf – Serial entrepreneur, talking head and devoted family dude.

Clint GreenleafThe Place: Kerbey Lane Cafe

The Cup: Iced tea for Clint and coffee for me – and lots of it. Those who know Kerbey Lane, know they are famous for the best pancakes in the known universe, groovy atmosphere and incredibly attentive service. After two hours, we must have had eleven refills.

Background: I broke with tradition for this interview and I’ll do it again 12 more times this year. Normally, I meet my “strangers” via a referral from some trustworthy source or another – typically my last stranger turned friend. This coffee with a stranger concept has the potential to be a lightning rod for crazy if I don’t play my cards right. Learned that the hard way.

For 2013, I decided to create a list of people I hope to interview in the year. Clint was the first one I reached out to and lucky me, he took me up on the wacky offer. I’m so glad he did.

Before we get into the meat and potatoes, I have a confession I’ve got to get off my chest. I make judgements about people based on how they look. I know, I know, bad person. I swear, it’s something I’ve tried, to no avail, to suppress. It’s not like I deliberately say, “OK, let’s examine this guy’s photo and draw some conclusions about his personality. Is he a jerk or will he be nice? If I ask him to have coffee with me, will he laugh and tell me he’s far too important to be bothered with such things?” Of course not. Instead, before the “suspend judgement” instructions make their way to my brain, it’s done, and I know everything I need to know about the guy.

It happens at the grocery store, walking down the street, when I’m watching Chopped.  I just can’t help myself.

As such, before I met Clint for coffee, I had already figured out exactly who I’d be meeting with. I knew he was a timid, soft-spoken, well-mannered midwestern family man. He married his high school sweetheart, and received a full academic scholarship to college, where he created the vision for a different type of publishing company. A company he’d start after two years of research and planning. I knew he was a shy, but nice guy and that because I mentioned a friend we had in common, he’d agree to meet me for coffee.

Wrong, wrong, mostly wrong, wrong, wrong, wrong, wrong, wrong, right, probably wrong. There goes my dreams of becoming an expert jury picker.

Before we get into the truth, here are some:

Common Grounds

  1. What is something you’ll regret not doing if you don’t do it? Staying in shape.
  2. What is your guilty pleasure? Sleeping in, because it rarely happens.
  3. What is your best feature? My sense of humor.
  4. What is your favorite movie? Braveheart. Although Shawshank Redemption, Swingers and National Lampoons Christmas Vacation were top contenders.
  5. What is the best compliment you even received? That I’m a good dad.
  6. What is something you wish you owned? A private jet so I could be home with the family more. (Business puts him on roughly 150 flights a year.)
  7. What is the best gift you’ve be given? My life experience. To which he added, “If I die tomorrow, I’ve lived an amazing life.” *
  8. What’s the best vacation you’ve taken? Lanai, Hawaii
  9. What food can’t you live without? Meat. Bison ribeye is a favorite.

Where did I go wrong in my pre-visit characterization of Clint? As you saw from my scorecard, pretty much everywhere. Here are the specifics.

Clint is a total wise-ass. He cussed less than five minutes into our meeting. And thank God, because I’d given myself a few guidelines prior to walking into the restaurant. OK, really just one guideline. Be lady-like. Which, I realize, is open to interpretation. For me, it means no potty-mouth and don’t order spaghetti. At 8:30 am the spaghetti wasn’t going to be a challenge. Swearing, on the other hand, is fun all hours of the day.

In addition to the cursing, he was opinionated, hilarious and affable. Oh, he also suggested smart, handsome, witty and charming. To which I’d add, humble.

You know how some people swear and that makes what they’ve just said pretty funny? Come on, I can’t be alone in believing a properly placed F-bomb turns the mundane into muahahaha. It’s like that game you play with fortune cookies where you add the words “in bed” to the end of your fortune – transforming them into lively table conversation. Take any regular sentence and throw the F-word (or some derivative) in there. Immediately hilarious. Or, immediately ____ ing hilarious! See? Clint has mastered the craft of saying something already cleverly funny and kicking it up a notch with an expletive. As an aside, see  the asterisks after #7 above? Insert the -ing version of our favorite F-word before amazing and you’ve got the actual quote.

It’s akin to Gourdough’s here in Austin who have managed to take an unquestionably yummy food item, the doughnut, and with a few tweaks, it’s mind blowing! I’m prone to exaggeration, admittedly. Not on this one, my friends! I have removed grains and sugar from my diet (because I am a total lunatic) yet once a year, on my birthday, I will indulge in a Miss Shortcake. It’s that good. Likewise, Clint is that funny.

Where were we? Oh yeah, my list of judgment errors. So, not timid or soft-spoken. “Well-mannered midwestern family man”?  While the first part is open to debate, he’s definitely a family man who hails from Cleveland. He’s such a family man that when I ask about his greatest achievement, he names his family. Then he whips out his iPhone and shows photographic proof of this accomplishment. Adorable! Seriously, magazine cover kind of perfection. Gorgeous (plus successful) wife and three angelic kiddos.

“Married his high school sweetheart” is not true. At all. Clint shares a story about high school that will debunk my earlier idea in short order. He’s 14 years old, 5′ 4″ and 200 pounds. Exiting the shower one morning he got a look at himself in the mirror and his future flashed before his eyes. What he saw looking back at him was not the suave, successful, ladies man he longed to be. Instead, he thought, “This is assistant manager at a gas station, nights and weekends. Not a guy who gets any dates.” In that moment, fueled – we can only assume, mostly by hormones – he set out to change his future.

Clint got into shape and didn’t stop there. He decided that Marines definitely get chicks. He joined the NROTC and went to college on a military scholarship with plans to become a Marine officer. Returning to my list of erred judgment, “got a full academic scholarship to college”, as we have learned, was not quite right, as the scholarship was military, not academic. Next, “where he created the vision for a different type of publishing company” was totally off the mark.

An injured shoulder and military cutbacks meant he’d not be commissioned, but his briefer than anticipated Marine experience would prove invaluable. For one, the uniform did make the ladies swoon, but more importantly, he learned two things that would change his life. How to tie a tie, and how to shine his shoes.

Clint’s major was accounting. Like many college guys, he was more likely to have a beer in his hand, than a book, so when he had six offers for internships from large, reputable firms at graduation, his friends were astonished. They’d studied slightly harder and earned 4.0’s, while Clint may have had a 3.0. Assuming he had some dirt on the people making the offers, his buddies demanded to know his secret. “I tied my tie and shined my shoes. The things the Marines taught me. And it worked.”

Irritated and envious, they challenged, “OK, if you’re so smart, why don’t you write a book?” So he did.

Clint showed me the PDF of the 28 page first edition of Attention to Detail: A Gentleman’s Guide to Professional Appearancecomplete with illustrations Clint himself, drew with a Sharpie marker. He printed 100 copies of the booklet and handed it out to friends and his parents. After his internship, he’d taken a job at Deloitte and Touche, and from the moment his butt hit the chair, he was unhappy and bored. So, at the suggestion of his dad, he decided he’d attempt to sell his book. He made some revisions and put an ad in an industry newsletter, offering the book to anyone who sent him five bucks.

The first day, he found two checks in his PO Box. The next day, seven. 13 on day three and day four and beyond, he consistently pulled between 50-100 $5 checks out the mailbox. At the age of 22, after seven months of accounting, Clint retired. If you’re interested, the book is now in it’s fourth edition and is called The Unwritten Rules of the Workplace: A Guide to Etiquette and Attire for Businessmen. From the looks of it, he hired an illustrator for this version.

The book led him to starting his publishing company, Greenleaf Book Group, which brings us back to the error list where “a company he’d start after two years of research and planning” turns out to be “a company he’d start because he was too young and naive to know any better.” In fact, Clint names starting the publishing company as the best mistake he ever made. He references something he calls “the vision myth” where people look back and edit history. “Oh yes, I had dreams of a company that would challenge the way publishing had been done for eons.” Not so. Clint says he started the company because he wanted to make enough money to impress the ladies. Why do I get the feeling this motivation is the true genesis for more companies than just this one?

While Greenleaf Book Group may have had a selfish beginning, today their philosophy is anything but selfish. In addition to the tie and shoes bits, Clint must have picked up a few leadership lessons from the military as well. Clint has a team of driven, dedicated professionals working for him and together they have turned the world of publishing on his side, if not its head. To learn more about their unique business model, check out this ebook.

I ask Clint about the keys to building a successful business, and without hesitation he tells me it’s about hiring the right folks. And based on the best piece of business advice he ever got, he adds “and take care of your people”. Clint admits he doesn’t always get the hiring part right, but he’s learned to be quick to fix it when he’s messed up. “Firing anyone sucks. Even bad employees. It’s like breaking up with someone but instead of just saying ‘I don’t like you’, you are also saying ‘and now I’m going to take away your livelihood’.” He tells me he’s very generous with severance and his reasoning comes from a level of responsibility I’ve never seen from a business owner. Clint says, “Sure, they sucked at the job, but I hired them. If you look back at any bad relationship you had, you had something to do with it.” Clint takes swift action and his share of the responsibility.

When asked how he’d make a living if happiness were the national currency, he told me he’d start businesses, just as he’s doing now. In addition to the publishing business, Clint also has a successful sports-themed baby clothing business called Bambino Balls. Like many entrepreneurs, he has a headful of business ideas, and as he says, “not all of them suck.” One project he’s excited about is a children’s book and product package featuring the infamous three little pigs aimed at teaching kids about money. I think its a safe bet we’ll see more exciting things from Mr. Greenleaf, born entrepreneur, in the future.

Why does he love business so much? He tells me being a business owner offers the best of everything. Beyond just making a profit, Clint loves creating things. He gets fired up when he identifies a need in the marketplace and figures out a way to fulfill it. He also says that businesses have an opportunity to create happiness for the employees, the customers and the vendors. He says, “It’s a virtuous cycle of wonder.”

Now to my final judgment errors. “I knew he was a shy, but nice guy and that because I mentioned a friend we had in common, he’d agree to meet me for coffee.” Clint is a regular contributing writer for Inc.com, he speaks at conferences and seminars across the country and has been featured in the Wall Street Journal, Inc. Magazine, and Entrepreneur. He is also a regular guest on Fox Business Network. So, shy? Not so much. Frankly, I don’t have a clue why he agreed to meet me for coffee or whether it had anything to do with our common connection, Gary Hoover.

In business, it turns out, judgements are made based on ties and shoes. In my world, judgements (admittedly, racked with flaws) begin before I even meet someone. My redeeming quality in this arena is the mutable nature of those judgments. I allow people to prove me wrong and welcome them to challenge me, hoping they will blow my mind (yay Gourdough’s!).

Have you ever heard you can learn a lot about a person by how they treat their mother?  You can also learn a lot by how they treat waitstaff at a restaurant.  I hope I’ve never been rude to a waiter, but I’m not the most engaging customer. Aside from placing my order and a thank you and a smile at the end, I’m not big on interaction. For as accomplished and well-known as Clint is, he has not let success go to his head. Clint was respectful and courteous in every interaction with our server. He called him by his name, looked him in the eye, smiled, made small talk and joked with the guy. He was kind to me and generous with his time, never making me feel awkward for having asked him to be a part of my project and not once rushing me to wrap things up.

The one judgment I managed to get wholly right turned out to be the only one that really mattered. “Nice guy”. Absolutely. Or, shall I say, abso-____-ing lutley!

To learn more about the amazing life of Clint Greenleaf, check out his site  or follow him on Twitter.

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