Life Lessons for the American Gentleman

We’re Moving!

Starting January 1, we will be bringing you a new website on a new platform. The American Gentleman will still be available at but we will have a new and improved website. 

We’re making this move in anticipation of a total revamp of AG. With a new book “New Rules of A Gentlemen” as a step beyond the original 150 lessons, we anticipate that AG will continue to be a starting point for young men (and women) to find important lifestyle, career, dating and life advice that makes them better every day.  

We look forward to the New Year and thank you for reading, commenting, asking questions and striving to make us and yourselves better every day. Your continued support, advice and friendship have made this journey all the more fun. Best wishes in the New Year. Cheers

- John, Editor-in-Chief/Owner, The American Gentleman

Christmas Essential.

Christmas Essential.

Merry Christmas!

Merry Christmas!

Every day.
Be well dressed.
Stock your bar…winter is coming. 

Stock your bar…winter is coming. 

From the Founder of AG comes: The Proposition: A Thriller Novella

This quick matching guide makes mornings easier.

This quick matching guide makes mornings easier.

Six Lessons To Live By

I came across this fantastic post on LinkedIn from Ari Emanuel. If you don’t know Ari Emanuel, he is the basis for the fictional TV character Ari Gold from Entourage. It’s worth a read and worth putting into practice:

The Six Lessons I Live By -  Ari Emanuel Co-CEO at WME

1. Surround yourself with people who are smarter than you and move out of their way.

If you feel like you know everything, you’re wrong. I know what I don’t know and then I find partners who can teach me. A perfect example is my partnership with Patrick Whitesell, my co-CEO at WME. While we take on different roles at the company and focus on different things, we share the same goals and at the end of the day, we’re working toward the same end. That’s been the key to our success.

2. The only constant in business is change. Get comfortable with it.

When I started in the business, there were four broadcast networks and 19 cable networks. Now there are five broadcast networks, 117 cable networks, Netflix, Hulu, YouTube, HBOGo, iTunes, Amazon Prime, VOD – the list goes on and on. Next year there will be more distribution platforms, and in ten years the landscape will have shifted another 180 degrees. The business is changing quickly, and the only way to succeed is to change with it. I always tell my colleagues, there is no such thing as a traditional talent agent anymore. It’s about pushing beyond that 10% commission and finding opportunity where it didn’t exist before.

3. Fail often, fail quickly.

Nobody fucks up like I do, but you’ll never succeed unless you take risks. Big ones. In 2009, we took Endeavor, a company that was doing incredibly well, and merged it with the oldest talent agency in the world. From a cultural and organizational standpoint, it was a big risk. People had their doubts. But we had a vision and a lot of help from very smart people (see #1.) Three years later, our business is stronger, our bench is deeper and smarter, and our deal-making is more innovative. It’s a better company – period. You have to lead by example if you want to promote a culture where risk-taking is rewarded.

4. Your schedule makes you dumber.

Force yourself outside of your daily schedule. Be curious and take time to learn about worlds outside of the one you live in. Watch the news, read the paper, educate yourself. Don’t be afraid to call people you don’t know, start a conversation, and ask for things you need. At the very least, you’ll be more interesting. At the most, you’ll take your business in new and bigger directions.

5. You only get one shot – make it count.

I learned this the painful way. After being hit by a car and lying face-down in the middle of Wilshire Boulevard, I was confronted with a whole lot more than my mortality. Take advantage of each day that’s given to you and do something to move the needle on your business, even if it’s just an inch. You’ve heard it before, but life is not a dress rehearsal. Don’t waste your time (or mine.)

6. Good ideas rule all.

In the end, it’s all about creative ideas and content – it’s the lifeblood of our business. I’m fortunate enough to work with the writers, directors, musicians and actors who are defining culture with their voices. It’s why I come to work in the morning. In 100 years, when the world looks different, and we communicate in new ways, and we have more devices and platforms and distribution methods, I believe great artistry will still matter most.

What the Great Gentlemen of the 20th Century Taught Us About Being Dapper

Looking good is easy enough. Buy a fancy shirt and throw on a clean pair of pants, and you’re pretty much halfway there.  But looking dapper is an art that requires thought and personality. Over the years, a few men have stood out for their polished looks. What is it that makes their look so timelessly appealing - and what can we learn from them?

Cary Grant (1904 – 1986) defines “clean cut.” With hair parted neatly to the side to complement his angular features, he is the sort of man who would look debonair in sweats - a rare feat indeed. Grant had a formula, and he stuck with it. Pressed shirts were paired with monochromatic suit jackets: it was simple, yet effective. He didn’t follow trends, because he didn’t need to. His look was timeless; and transcended location and surroundings. Grant’s name even possesses a clipped and tidy air (a studied choice, as he was born Archibald Alexander Leach and legally changed his name). Thinking of a new vogue haircut or eccentric new fashion statement?  That’s bush league.  Real style is timeless, clean, and transcendent.  Just ask Cary.


Frank Sinatra (1915 - 1998) once sang that “you’ve either got or you haven’t got style, and if you have it, you stand out a mile.”  That was more than a lyric for Sinatra, who was notorious for always being well dressed in fine and expensive suits.  His taste was timeless, favoring tailored suits paired with conservative silk ties or bowties and fedoras. A stickler for the details, Sinatra cared about things like cufflinks and sleeve-lenghts, and where trousers should fall on the shoe line.  Undeniably suave, Sinatra left an image of a gentleman that gave a damn about putting his best foot forward, dazzling the crowds with his vocals and his style.  Sinatra’s lasting style legacy:  Stay conservative, and invest in a good tailor. 


A poet and writer with a devil-may-care attitude, Jack Kerouac’s (1922-1969) personality was contagious. His cavalier approach to life was also reflected in his clothes. He bottled up the “car ride with the windows down” look and infused it into his style. Kerouac was the Beat Generation, and his ensembles showed it. His flannel shirts fit in with the mountains of Washington with the same ease that they did in Brooklyn’s coffee shops. And Kerouac’s bomber jacket was a staple that only looked better with age - its distressed quality was tangible proof of his untamed lifestyle. Kerouac created the art of cool, and it’s a statement that isn’t going anywhere. 


Frank Sinatra once said that Ray Charles (1930 – 2004) was “the only genius in show business.”  His music and his clothes showed it. He was always hovering between a polished look and a relaxed one. His shirts were impossibly elegant - but they were always buttoned down to give off the allusion that he had just worked up a sweat (and let’s be honest… he probably had). Donning his signature black sunglasses, Charles looked dramatic with just a touch of mystery. He toed the line of slapdash style, but he never crossed it. Every poised suit had just a touch of dishevelment to it that said, “I don’t give a damn.” For the man who wants to look good without being predictable, channel Ray.

 Take the cues of yesterday’s finest gentlemen, you can craft a distinctive style that will make a timeless statement. Looking good is a man’s game.  Looking dapper is a gentleman’s style. Dress with thought, tip your hat to the greats of yesterday, and walk dapperly ever after.

 About the Author:

Jake Kaufman lives in Columbus, Ohio and writes on behalf of Bosca.

Founded in 1911, Bosca is the dream of a young Italian immigrant named Hugo.  Surviving wars and a Great Depression, Bosca continues to create luxurious leather goods that introduce the passion of Italian design to the demands of American functionality.  Find out more about Bosca by visiting their website @