
In my book that’s coming out next month I talk quite a bit about how executives who want to become entrepreneurs need to change their relationship with money because, when you’re in business for yourself, it doesn’t flow quite as easily as when you’re working for the man.
That got me thinking about the stupid sh*t I squandered money on in my pre-entrepreneurial days. Figuring that if you’re about to take the entrepreneurial plunge you can learn from my spending mistakes and save your money to help fund your survival in business, here’s a list of some of the dumb things I have spent money on. I wasted the money so you don’t have to!
I’m not saying you shouldn’t spend your own money on these particular things: your wasteful spending may be different from mine. But you’ll get the point.
- MONEY PIT #1. We put in a pool when we moved here seven years ago. It’s not a fancy pool: 16-x-32, semi in-ground with a deck around half of it. Total cost with deck around $25,000. Add to that the annual cost of having the pool guy open and close it, and chemicals, and we’re up at around $32,000 (not including forsaken risk-free appreciation I could have had in a CD). In seven year I estimate we have used the pool 70 times for a total of 35 hours. Let’s see, what else can I buy for $900+ an hour! (Eliot Spitzer, any suggestions?)
- MONEY PIT #2 and #3. When I was younger, I kept thinking that if only I had a bigger house, like the other senior executives in the company, then I’d be happy. My wife was happy with our 1200-foot, three-bedroom house on a fifth-acre. Had we stayed there (my wife always described it as her dream house) the mortgage would have been paid off about 10 years ago. But no, I kept wanting more. Soon it was a 4,000-foot house in the same town, then a bigger house in another town. I never felt so stupid as the day I closed on that house and had to write an unexpected check to New York State for $10,000–a “millionaire’s tax” for buying a house that cost over $1 million. We hated the new town and moved back to our old town less than two years later, around the time I started self-employment. Our house (and this is the last one!) is half the size, half the cost, easier to clean. (Still paying off the mortgage, though.)
- MONEY PIT #4. Like any exercise equipment, my treadmill was totally useless all the years I had it! One thousand dollars wasted. How about eating less and walking more? My happiest day was when the basement flooded and I finally got to drag that thing to the curb. Forget treadmills, forget health clubs. Tie some $10 weights to your ankles and get your butt outside!
- MONEY PIT #5+ I long ago gave up buying pens that cost more than $2; suits from anywhere except Men’s Wearhouse; any kind of collectible, like Playboy magazines from the Fifties and Sixties (for the articles, of course), which lost value faster than a Zimbabwean dollar. And so on.
So, now that I have thoroughly embarrassed myself, I ask you, entrepreneurs-in-training: what are your dumbest money-wasting activities you plan to give up when you start your business? Or if you’re well under way with your business, what changed in your spending habits. Don’t leave me hanging here…admit you’ve been as dumb as me.

