Convincing My Uncle Ted That Running A Business is Worthwhile


Every once in a while, my 96-year-old Uncle Ted will stop by my shop and drop off tools he bought from a garage sale. He has been doing this for many years, going back to when we first started the business almost 30 years ago.

I think he is pretty proud of what we have accomplished with our business. However, he grew up during the Depression era and sometimes I’m not sure he understands why we need all of the equipment and trucks we have. The following is a mashup of various conversations we have had over the years.

How many of you face the same type of questioning from well-meaning friends and family?

Uncle Ted: “Why do you want to have your own business? Wouldn’t you just be better off being a postman?”

Me: “A postman?”

Uncle Ted: “Yes, you know the guy who delivers the….”

Me: “Yes I know what you mean, Uncle Ted, I’m just saying the whole postman thing isn’t my bag.”

Uncle Ted: “Look at all these mowers in here, and trucks, trailers – my gosh, you have equipment everywhere. This all must cost you a fortune. Postmen don’t need all this stuff.”

Me: “Well, I understand that, but I’m building a business here.”

Uncle Ted: “Why would anyone want to do something like that? Sounds too risky, I’d just rather deliver the mail.”

Me: “I understand that delivering the mail is probably a more stable job. Come to think of it, driving that little truck around does seem like fun, but what I am doing here is building a dream.”

Uncle Ted: “Seems like more of a nightmare to me: spending all your money on all this stuff.”

Me: “But that’s the price you pay for having a business. All this equipment is making me money. I know it’s risky, but that’s part of the excitement of running a company. I don’t just go to work every day at a job, I come here to build a business. It’s about more than security. It’s about playing the long game and dealing with the ups and downs. At the end of the day, it’s about building a legacy – something that is bigger than just me and something I can be proud of.”

Uncle Ted: “Did you say something? I couldn’t hear you over the rumbling of that truck over there.”

Me: “I know this doesn’t make a lot of sense to you because you worked hard all your life at the same company for many years and you retired with a nice pension, but that just isn’t the norm anymore.”

Uncle Ted: “Well, I guess so.”

Me: “I’d rather take my chances on myself instead of letting someone else call the shots. Sure, I may lose it all but that is a risk I’m willing to take because I’m betting on myself, and I’m planning on winning.”

Uncle Ted: “Last time I made a bet I lost my shirt.”

Me: “It’s like talking to a wall.”

Uncle Ted: “What?”

Me: “Never mind.”

Uncle Ted: “Well, I picked up some more tools for you while I was out at the garage sales last week.”

Me: “Let me give you a hand getting them out of your trunk.”

Uncle Ted: “At least you will save a little money with these; I got them all for a good price.”

Me: “Those are some nice rakes, Uncle Ted. Thanks.”

Uncle Ted: “No problem, you got a pretty big building here and all these people running around. Looks like you are pretty busy. You just keep up the good work. Um … I mean this building must cost you a fortune to heat; I just don’t know why you need such a big place.”

Me: “I know, Uncle Ted, it’s so expensive. Hey, look, here comes the mail. I’ll bet I got some checks today.”

Uncle Ted: “I sure hope that mailman never gets a crazy idea to start a landscape business.”

Me: “Me too, Uncle Ted, me too.”