Dan Waldschmidt

by Dan Waldschmidt

June 16, 2018


Although he came from a family with significant money, George Steinbrenner’s strict German father, Henry, refused to just hand everything to George on a silver platter. 

Not even an allowance. 

When George was nine, his father did start paying him for chores done around the house. In chickens. 

Chickens weren’t the kind of thing you could take to the store and spend on a bike. He had to take care of them. Clean up after them. Feed them. Make sure they had water.

And when they finally started laying eggs, George started his own company — the George Company.

He went door to door in his Ohio neighborhood selling eggs to anyone who would buy.

And George’s egg company turned into a fruitful business over the next five years.

When George had to leave to go to military school, he left the egg company to his sisters and they continued to run it for the next few years. 

That was George’s first taste of being a real businessman. 

George didn’t participate in any business ventures while in school. He did however participate in sports. He became a track and field star in college.

And when he graduated, he joined the Air Force. 

While in the Air Force, George’s love of sports and money came rushing at him full force. He ran the sports program on base and also ran a mobile coffee shop — out of a truck.

His coffee business was so successful that he eventually worked his way up to having six trucks. 

When he was discharged from the Air Force in 1954, instead of running home to work for the family shipping business, George went back to school to get his Masters in Physical Education.

And he worked coaching football. He couldn’t get enough sports. 

But George’s father, Henry, was done watching his son waste his time on sports and pressured him to come back to the family shipping business where he belonged. 

George was loyal to his family, and he respected — and feared — his father, so he returned to Ohio.

HIs love of sports could not be stifled, though. And with the money he made from working with his father, George bought a minor league basketball team.

The team ended up failing and costing George over $25 million in the long run.

Bruised but not broken, George shrugged it off as a loss and went right back to work. 

Instead of dumping any more money into another sports team at the time, George decided to take his money and dump it into a shipping company of his own. He bought shares, became president and then ended up buying the whole company. 

He turned the failing company around and made millions. George took those millions and bought another sports team. 

This time a major league baseball team — The New York Yankees. 

In 1973, the team was declining. They had won some championships, but they were slowly falling apart. George spent obscene amounts of money to bring the best players he could find to revamp the Yankees. 

People thought he was crazy for spending $2.5 million on a single player. But George brought his business savvy to baseball and his belief that you had to spend money to make money.

And if players were the key to winning baseball games, he would spend money on players.

Because George Steinbrenner would do whatever it took to win. In baseball and in life. 

George was the man Major League Baseball loved to hate. He was the most successful team owner in all of professional sports.

To be honest, most people hated him for being better at the job of team ownership than anyone else in his sport. He spent his money to win however he saw fit — even if it got him in trouble with the law and kicked out of the league temporarily.

He did whatever he wanted. And he wasn’t detached from reality. Winning was everything. He was fiercely loyal to his Yankees family and his fan base. 

Even though George Steinbrenner didn’t have the typical rags to riches story people like to hear about, he worked each day like he was broke. It was raw obsession.

Before every single home game, George would get to the stadium at least an hour before the gates opened to make sure that the place was in pristine condition.

He walked every inch of Yankee Stadium, including all the bathrooms, to make sure they were clean and ready for fans. 

When he ran into young fans, he showered them with attention and conversation.

When children would walk up to him with their old, tattered or cheap baseball caps and ask him to sign them, he would.

And then he would ask their parents’ for their home address and send them a brand new autographed team cap, a uniform, and some tickets to a home game. That’s how much he loved the fans and the kids. 

And he loved his baseball family just as much.

When George received a note from the wife of an ex-player named Joe Pepitone asking George to help her husband, George was quick to help.

Pepitone had played for New York before George even bought the team, but he believed that the team was a family.

And Joe Pepitone was forever family.  

He hired Joe as a hitting coach for his minor league team. But before long he was a major league hitting coach — and his life would never be the same again. All due to George’s giving nature. 

It doesn’t matter how you get where you are going. You don’t have to have suffered and started at the bottom to be considered a success.


You don’t have to have struggled to be valuable. You don’t have to have failed and lost to be able to deliver awesomeness. 

People just want to know that you can empathize with them. People want to know that you don’t think you are better than them just because you have more zeros in your bank account.

They want you to be relatable and caring. 

How are you helping? Who are you mentoring? Who are you hiring? 

George was a giver. He was always supporting youth activities, donating to hospitals and the arts. He made a name for himself, not only in baseball, but in the lives of millions of fans. 

The last home game George ever attended he looked on at the crowd as they gave him a standing ovation for 35 years of ups and downs.

Tears rolled down George’s cheeks trying to absorb all the love in that stadium. Despite never winning a World Series, his fans were still rooting for him. They still adored him. 

Because he was one of them. 

When George Steinbrenner passed away eight months later his Yankees had won 7 World Series titles and 11 pennants. That’s why they called him “The Boss”.

About the author

Dan Waldschmidt

Dan Waldschmidt doesn’t just talk about leveling up. He’s obsessed with it. He's set records as an ultra-runner and been the personal strategist for the leading business leaders of our time. He wrote a book, called EDGY Conversations that accidentally became a worldwide bestseller and continues to share his insights from the stage as a keynote speaker and on the blogs and podcasts you will find here. Most days, you'll find Dan heads-down, working on breakthrough strategies for his clients at EDGY Inc, a highly-focused, invite-only, business strategy execution company based out of Silicon Valley.