Mad Men and the Idea of Business

Last Updated on August 31, 2023 by David

Timeless quotes to help a business win.

I’ve literally watched the beloved series, Mad Men, 5 times. It’s easily my favorite period-show of all time and any entrepreneur should do themselves a favor and watch it (if not for the amazing cinematography and wardrobe selections).

Several business related themes always pop out at me:


Never be afraid to invent or reinvent yourself.

The founding team portrayed in Mad Men has had to start and restart many times throughout the series, much like startups and their pivots of today. Aspiring entrepreneurs need to embrace change when they’re faced with it.


Opportunities are created and reserved only for those who’re prepared.

The main character of Mad Men, Don Draper, is a self-made man in the most literal sense of the word. Don was never satisfied with the status-quo, always looking out to get to 100%. Even with his flaws, Don is a meticulous preparer, thinker, and strategist. Business owners can learn a thing or two about the way Don thinks.


Learn to recognize talent and character

People join and leave Don’s advertising agency throughout the series but only a handful of people are truly trusted and given the opportunity to grow and come along for a new venture. Not only do the people you surround yourself with need to be talented but also have a strong sense of moral character. They are the centerpieces of your business culture.


Growth culture is important and the people you lead need to know

Your team needs to know there is room for them to grow and thrive in a chosen career. The prime example is Don’s previous secretary, Peggy Olson, turned Senior Copy Writer. Business owners need to establish and grow a culture of self worth and taking initiative in order to grow that worth. It’s a win-win for everyone.


Here are some of my favorite quotes that inspire business owners to think differently and bravely.

“Go home, take a paper bag and cut some eye holes in it. Put it over your head and look at yourself in the mirror. Really evaluate where your strengths and weaknesses are, and be honest.” — Joan Holloway

Any self respecting founder or leader will take it upon themselves to self evaluate/diagnose and be comfortable doing so. Lying to yourself and living in ignorance won’t get you very far.

“The day you sign a client is the day you start losing one.” — Roger Sterling

“My Father used to say this is the greatest job in the world except for one thing: the clients.” — Roger Sterling

There should always be a sense of urgency when it comes to growing your business because churn and loss are bound to happen even when great relationships are present. The only way to combat churn is to grow faster.

“Even though success is a reality, its effects are temporary.” — Don Draper

Businesses need to celebrate small wins more frequently because success is really a never-ending pursuit.

“People want to be told what to do so badly that they’ll listen to anyone.” — Don Draper

“The truth is people may see things differently, but they don’t really want to.” — Don Draper

This says something about good copy and the much needed confidence in shipping new features or updates. It doesn’t mean to cheat and scam your customers but to espouse enough confidence about your business so they know they’re in good hands.

“It’s your life. You don’t know how it’s gonna last, but you know it doesn’t end well. You’ve gotta move forward as soon as you can figure out what that means.”

As morbid as this feels, I’ve always found inspiration from it. Life is short and often rough. If you know what you want, it’s best to start now and do something that makes you happy. If that is to start your own business, then do it.

“If you don’t like what’s being said, change the conversation.” — Don Draper

This is probably the most famous Don Draper quote. Never play into the hands of your competitors. Always form your own story and forge your own path. Playing back hand to things that are disadvantageous to you is effort spent on the wrong priorities.

“We all try. We don’t always make it.” — Don Draper

Not all businesses succeed. Try and try again. That’s the entrepreneurial spirit.

“Sometimes when people get what they want, they realize how limited their goals were.” — Joan Holloway

Aim high. Think big. Execute flawlessly (as much as possible at least).

“Just think about it. Deeply. Then forget it. And an idea will jump up in your face.” — Don Draper

For when you’re running lean on inspiration.


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