Miles Jennings

personal site & blog

An overly professional bio website for Miles Jennings


The Many INsane Jobs of Miles Jennings

My kids often make fun of me for the many rather unusual jobs that I have held. However, I'm sure of three things: 1.) It's not that unusual, 2.) they have no right to make of fun of me (hear that, kids?) and 3.) these jobs somehow accumulated the right kinds of experiences in order for me to be now doing what I love, which is building tech companies.

So, this page is called "The Many Insane Jobs of Miles Jennings," but I could have instead called it: "It Was All Worth It." 

I had every job here before the age of about 23, when I realized that I loved sales and business. Below is the rather insane list of jobs recorded here for posterity.

Paper Boy

Do they even have paper boys, or more accurately paper people any more? A. No one reads the paper and B. Grown ups with cars take all the gigs. I had a suspected drug dealer on my route that would take out a massive roll of bills when I came around to collect, and would give me the occasional $20 (much-appreciated) tip. 



Lawn Mower


I thought I was pretty cool by printing out flyers and under-cutting any reasonable professional lawn service. I illicitly blanketed the neighborhood with those flyers and soon my phone was ringing off the hook. When you charge $10 no matter how big the job is, you tend to do pretty well.


Shrink Wrapper

You know those beautiful gift baskets with towers of fruit and nuts? You know how there is a tight plastic coating holding everything together and making it shine? Shrink wrap doesn't just shrink itself, you know. My job was to take a hair dryer and, holding it at the proper distance, heat the plastic into the proper form. Hold it too close, and boom - you have a hole. 

Garden Furniture Straightener

My job as a store clerk mostly involved wearing a purple vest and walking up and down the aisles, looking informed and helpful to the customers. Secondarily, my job was to straighten inventory so that everything looked inviting for purchase. We had zero training, and if you headed to the game aisle, the other employees were playing games in the aisles.


Bagel Cutter

Boston clientele are serious about their bagels. We made delicious fresh bagels and served them with every conceivable combination of cream cheese, lox, lettuce, tomatoes, and various meats. In front of a customer, I slipped with a long bagel knife and nearly cut my finger off. She screamed, but did not flee the store. She came for a bagel sandwich and left with one. A new one, of course.


The kid I was babysitting loved peanut butter and honey sandwiches. But he also refused any kind of drink and swore that his mother let him do that. "You'll choke," I said. And he did, almost. If I ever have to defend my life in the afterlife, as they do in the movie, I may point to this act as my redemption.


I proactively applied to a charity as an intern. Each time I went in, they invented some new mundane task for me, such as stapling a thousand documents together, or designing a postcard flyer in Illustrator. At the end of the summer, they wrote me a letter of thanks saying, "We never know we needed an intern before you came." High praise, indeed. I created a need, and then left them.

Ran Painting Company

One summer, I ran a painting company through College Pro. I wrote about it on Entrepreneur. After my various other jobs, it was a wake up to hire people, run payroll, do sales, and invoicing. The hardest part was facing my fear of heights and climbing up on ladders. I also faced one of my most difficult personnel issues to date, when a painter I hired showed up on acid.

Propane Denier

I worked the phones for a propane delivery company. Customers would call up, desperate for propane to heat their houses, demanding to speak to management. The manager would gesture wildly to me that he was not there. One learning opportunity as well: if you see propane trucks on the highway, give them a wide berth. I understood the drivers to have rarely slept before their shifts.

Ran Painting Company

Propane Denier

Microfilm Salesman

Bookstore Clerk

Late Night Snack Vendor

Endless Rubber Belt Maker


Restaurant Manager

Website o' Miles Jennings

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