Side Hustle

When I Win the Lottery

In Colorado, there is no shortage of gambling opportunities. Just 45 minutes up the road in Blackhawk and Central City, we have large casinos that rival most Indian reservations. We have legalized bingo halls all over town. But the dream is to win the lotto.

Where the Dream Comes From

I think everyone has a list of “if I win the lotto” ideas. One of my friends told me that winning the Power Ball is his retirement plan. He also owes me a 1968 Cherry Red Chevy Camaro if he wins.

After recent epic winnings in the Power Ball, I got to thinking about my lotto list.

Dreams of Unlimited Money

If I had virtually unlimited money, what would I do?


I would buy a massive mansion in my hometown, Denver, or a giant Penthouse downtown. I would have a vacation home in the mountains, probably in Beaver Creek. I would buy a beachfront home in Miami overlooking South Beach. I would buy two apartments in the Old City in Jerusalem (one for Passover, one for the rest of the year). Oh yeah, and I can’t forget the Manhattan penthouse.


I always talk about my practical car, which I love, but who would want a McClaren F1? That is the top of my list. I also want a Tesla Roadster, 1968 Camaro, a James Bond decked out Aston Martin, a shiny new Ferrari Scaglietti, and a Bugatti (not too picky on the model).


Honestly, my many homes would be empty most of the year. My real home would be the entire world. I want to travel and see every place that I can safely see that I have never been. I would love to be able to hop on a plane at my leisure to visit the most beautiful and cultured places in the world.

What I Would Really Do

If I really were to win a windfall lottery income, I would probably be a little more thrifty with my money than the list above.

I really would have a comfortable home in Denver and an apartment in Jerusalem. The others are negotiable.

I really would have to buy a McClaren F1 if I had over $100,000,000, but beyond that I would probably stick with a luxury sedan for my daily driving and an SUV for the Colorado winter.

I would really travel the world. I want to see everywhere, and having an extra nine figures in the bank would make that dream come true.

I would also donate generously to the organizations that have given me so much and ones that help people who really need it. I would also make sure my parents and sister lived incredibly comfortably for the rest of their lives.

Most importantly, I would invest and secure my fortune in a way that ensured I would have enough money to live comfortably for the rest of my life.

The Pitfalls of Instant Fortune

I have read stories of people winning $300 million jackpots and struggling with drug addiction and bankruptcy just a few years later.

The best example of this is Jack Whittaker. Whittaker was a successful construction manager with a great family life. One day, he walked into a store for a sandwich, gas fill up, and a lottery ticket. He won the largest lottery in United States history at that point ($315 million) and took home a lump sum of $113.4 million.

Within four years he was robbed several times, arrested, sued, and been implicit in the death of his Granddaughter and two of her friends (separate incidents) related to drug use. After a string of legal problems, nearly ending up in bankruptcy, and burying his grandchild, he said that “if he could do it all over again, he would have just filled up his tank, bought a sandwich and gone on his merry way.”

My Plan to Win the Lottery

I am going to win the lotto, I should probably buy a ticket. Doing the math, however, shows that putting money into an index fund has a much higher rate of return than the predicted average income from the lottery. I will put my dollars into a sound investment instead. I guess this is one dream that will never come true.

2 thoughts on “When I Win the Lottery”

    1. It is always great to dream, but I would rather create a positive ROI and dream about what I am going to do with the return. Is that the accountant in me talking? 

Comments are closed.

Scroll to Top