Dan Waldschmidt

by Dan Waldschmidt

March 26, 2018


Let’s be honest, you can spend years of your life wondering why you aren’t in a job that makes you happy. Why you wake up every day in business relationships that are negative — draining you of your ambition and joy.

By now you might think that you have to settle for a depressed, angry future. Where you just end up going through the motions — grabbing a paycheck and hoping that you outlast the new boss with big ideas.


It’s time you started thinking about your business situation a bit differently.

The truth is that you might not be doing anything wrong if you have had dozens of jobs in your life so far — and none of them have stuck. Especially if you’re an entrepreneur. In fact, you are in really good company. 

Tony Hsieh had a whole list of careers under his belt before he even graduated high school. 

From trying to start a worm farm in grade school, to having garage sales and newspaper routes, a greeting card company, a button-making business, working as a spotlight operator for the local community theater, a video game tester, and working at a computer programming company –Tony just couldn’t figure out what he wanted to do with his life.

He just knew he liked doing his own thing. 

College posed less of an obstacle for a very determined Tony.

He catered weddings, tended bar, worked as a computer programmer — and was even a member of the Boston chapter of Guardian Angels where he helped patrol the dangerous subways and alleyways of Boston keeping an eye out for trouble.  

He finally settled into his last two years at Harvard running the Quincy House Grille. A dining area in his dorm. 

It was a business that started with Tony making daily treks to the nearest McDonald’s to buy frozen beef patties and buns and carting them back to Quincy House to heat them up and put them together– selling them for a $2 profit per burger.

He soon found himself exhausted and not making the amount of money he had hoped for with his ingenious idea. 

So he ditched the burgers, took $2,000 from his profits and bought some pizza ovens for the dorm eatery.

He recorded MTV music videos, cut out the commercials, and played music nonstop in his new pizzeria.

The students flocked to his establishment — buying pizzas for $10 each and selling them by the slice. He had figured out how to make money in business. 

But graduation was soon approaching and Tony still had no idea what he was going to do after college.

He followed his fellow graduates like a lost sheep to a job fair. He visited all the hiring tables and tried to figure out which job he could make the most amount of money doing the least amount of work.

He admittedly had finessed his way through college and was hoping he could do the same in life. At least for a little while.  

As luck would have it, Tony landed his first real job at a place called Oracle, where he was paid $40k a year to sit at a desk and run tests from his computer all day.

Tests that took 3 hours each. Tests that he did not have to be there for.

So he would come in late. Start the test. Leave for lunch. Go home. Take a nap. Come back. Start the next test. Talk to friends. And pretty much waste the day away. 

At first, he really loved it. He couldn’t believe he was getting paid a lot more than his fellow graduates who were working a lot harder.

But after a while, the entrepreneurial bug that had been lying dormant inside him woke up. And it was hungry. 

Tony found himself hitting the snooze button over and over before finally crawling out of bed and heading to work. The same thing he used to do in college when he dreaded a class. Lunches got longer. Work became more and more problematic to him. 

Finally, he and his coworker and roommate, Sanjay, decided to do some brainstorming.

They were living in the middle of the internet boom. And they were smart.

So they started trying to come up with ways to get in on the web. Idea after idea was ruled out.

Until one day, they stumbled upon a crazy idea that they thought just might work. 

Internet Banner Ads on web pages. 

They eventually called their new company LinkExchange.

After they perfected the idea a little bit more, both roommates quit their jobs. Sanjay would have to build the program they would use. Tony would sell the banner ads and websites to local businesses.

They had enough in savings from their college endeavors that they could live for almost a year without having to work.

And so they worked on their big idea. 

It was an idea that took off. People loved the internet ads they were creating. People loved the websites they were creating.

In less than 5 months, they received an offer to buy their company for $1m. They counter offered with $2m, but the party backed out. 

But they didn’t care. They were having fun with their business. They didn’t dread work anymore. They enjoyed it. They were happy to keep running their new business. 

For six more months that is. 

When Microsoft outbid Netscape to buy them for $265 million. In cash.

Tony and Sanjay weren’t even 25 years old yet and they were gazillionaires. 

Part of the deal included the partners would stay on at LinkExchange for a year or lose 20% of their buyout.

As the days passed, Tony grew impatient to leave. 

Not long after, he sent a farewell email to his employees and friends and left the company he had started. Leaving millions of dollars on the table.

He had everything he could want. An apartment above a movie theater — that was only a couple blocks away from Taco Bell. And he was a millionaire.

Tony and his old college classmate, Alfred, who was now his neighbor above the theater, decided to use some of their cash flow to invest in startups. 

Together, they had invested in numerous startups already when a little shoe company came on their radar. It was an online shoe company.

Not unlike the catalog ordering programs of the time, this shoe company would showcase its stock on the internet and you would pick the size and style and it would be shipped to your house.

Tony was unsure.

Until he learned that the shoe business was a $40 billion business — and that even 5% of that, which is what they aimed to claim online, was more $2 billion.

He was in.

After a short while, he became the CEO and started putting all of his prior work experiences into practice. 

He bet on creating an employee culture that would keep people happy and content at work. He strived to create not just a work-life balance, but a work-life-integration system. 


And so, Tony Hsieh and Zappos created a culture that produced awesome people.

It all started with the hiring process.

Which is less of a recruitment and more like the beginning of a love affair.

There are numerous dates that consist of the prospect meeting numerous employees to see if they will fit into the mix. This usually happens at a party or gathering. Sometimes more than one over three or four months. 

If the potential hire doesn’t pass the “cultural fit interview” they don’t make it to the next level.

If they do make it, however, and get hired — no matter the position — every employee is trained in the call center for three to four weeks.

Because they take the hiring process so seriously, Zappos does not hire temps for the holidays and busy seasons. Instead, they require every employee to work 10 hours per week in the call center during peak seasons.

If the call center is not your cup of tea at the end of the training, Zappos will pay you $2,000 plus your salary to go away. No hard feelings. 

But if you take the money, you can never try to work at Zappos again. 

They’ve only written one check in the last couple years.

Once people get hired they don’t want to go anywhere. Mostly because they have a sense of freedom.

There are no scripts in the call center. Employees are encouraged to use their better judgment and creativity for customer retention.

And it works. More than seventy-five percent of Zappos customers are returning customers. 

And managers, well, they get to spend 10-20% of their time working on team building exercises with their department to ensure a healthy work environment. 

On top of all that, the company sponsors a couple of family events each year that include a summer picnic, a vendor party for employees and families, movies, bowling, easter egg hunts, and an annual party at Tony Hsieh’s house every January.

So you get to hang out with your co-workers and their families thus forging an even stronger bond among the collective group. 

Tony has said that his employee culture is “about giving employees permission and encouraging them to be themselves”. As he sees it, his company, Zappos.com, is not just a website but “a lifestyle delivering happiness to everyone including us.” 

As it turns out, most of us want to be happy at work. Sure, making money is good, but being able to support your family while being happy on the job is the ultimate goal. 

And you can make it happen. You can take steps like Tony to move from boring to compelling. From doing a chore to living your life’s mission.

Try offering suggestions to the company you work for. 

Or you can turn your crazy idea into a transformative lifestyle — like Tony did.

You already have the experience and you may already have an idea.

What’s stopping you? Your previous failures? Your burnout?

Take all the things that are wrong with every place you have ever worked — and turn them into something new and inspiring that you pioneer next.

Sure, you may get crazy looks at first, but it may be the start of a billion-dollar business — like Zappos.

That starts with you being willing to jump around and get it wrong — until you figure out what awesome looks like.

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.