If One of Your Employees Won the Lottery, would they Quit or Keep Working for You?

Jerry Roth
The Startup
Published in
4 min readOct 12, 2019


Author at Work — RockerFeller.Rocks

Barbara didn’t need to work. She and her husband had just spent their anniversary at Caesar’s Tahoe where she put 5 coins in a dollar slot machine and won a million and a half-dollar jackpot. Her husband already knew where he wanted to spend the money. She had reservations about his plans but didn’t think this was a good time to argue about money.

When I arrived at work on Monday, there was a photocopy of the check on top of my desk. Thinking it was a joke, I took the check into the accounting office and found her sitting in her chair, visibly shaking. The rest of the crew were trying not to look at me while snickering.

“Okay, what’s going on?” I asked, but I couldn’t help grinning.

They all looked up at once and said almost in unison, “It’s real! She really won!”

Barbara sheepishly smiled at me and nodded.

I cocked my head, lowered one eyebrow and said, “Wow, congratulations, that’s a lot of money.”

We had 150 employees at the time and Barbara was one of the newest hires. She was also one of the best. By the time she was hired, we had gotten very good at interviewing and determining who would best fit in, who would enjoy our culture, who would treat our customers the way we wanted, and who would show up for work consistently. Barbara passed with flying colors and for the last year and a half had proven to be a perfect example of our system at work.

As she told me the story of her jackpot, I was thinking about how hard it would be to replace her. She finished her story with a recap of her husband’s plans. When I sensed she didn’t agree with him, I asked, “You’re not thrilled with that idea, are you?”

“No, I’m not. In fact, I was hoping you could talk to him. To us. Help us come up with a better plan. I don’t think we should spend it all at once.”

I had to admit, I was flattered. It felt good to know my people trusted me, thought I was the guy who could help them with advice for their future, not just be their boss. I said, “Sure. Of course. If you think he’ll listen. But I’m curious. Should we start looking for your replacement?”

Barbara was the standard by which good employees are measured. I greedily hoped she would stay. On the other hand, what a wonderful stroke of luck for her. How could I possibly compete with a one and half million-dollar jackpot? She would leave and I would support her decision. But I still felt a little gipped. And more than a little envious.

She surprised us all when she said, “No, I’d like to stay and keep working. Is that Okay with you?” She actually asked me if it was Okay if she kept her job!

When I looked both confused and excited, she continued, “After I got past the initial urge to not work anymore, I realized I would miss it. I’d miss you guys, I like it here.” She admitted being excited at first and seriously thought about quitting. The only reason she could think of to quit was, she didn’t need to work. But she enjoyed coming to work. She liked working for us. She wanted to stay because it was fun and she enjoyed the people.

As her boss, I felt a sense of pride. I had worked hard to create a workplace that people wanted to come to. What better test than to have someone who’d just won a lifetime jackpot still want to come to work? It felt good.

If you are a business owner or a manager, how many people, who currently work for you, would stay if they suddenly found a fortune? On the other hand, how many would you hope would leave?

How do you determine who to hire? How do you treat them after you do?

One simple secret I like to use is to treat them like owners. In other words, ask for their opinions and ideas, listen to what they say, include them in decisions, allow them to have fun, treat them with respect, treat them like owners.

If you’re an employee, do you perform like the only reason you’re there is because no one else will hire you? Do you condemn, criticize, and complain most of the time? Or do you contribute to the happiness and success of the team? Would people miss you if you left?

If you were an owner, what would you change? Do you have good ideas that could help improve things? Do you respect your boss and your coworkers? Would you rather be working somewhere else?

Kids grow up to be young adults and have babies of their own. They become parents without taking a class, getting a license, or interviewing for the job.

Why would our society be Okay with this? Why do we allow it?

It’s simple; because they own it — the kid is theirs. And they will treat it differently than a rental car or a minimum wage job.

Are you treating your employees like children? Or owners?…

Would you like to learn more about creating a culture of owners? Click on the link to get my book, “What Would the Boss Do?”

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Jerry Roth
The Startup

It’s only lonely at the top if you're there by yourself. 44 years of management experience I would love to share with you. Visit JerryRoth.com