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Begin the Begin Podcast by Jeff Hilimire
How the hardest day’s work I’ve ever had shaped my life forever
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-4:49

How the hardest day’s work I’ve ever had shaped my life forever

My dad, his wife (the amazing Grandma Dee!), and I at a 48in48 event.

It was a little after 5 pm when we got home. I said hi to my mother as I climbed the stairs to the main level of our house.

“How was it?” she asked, referring to my first day working with my father.

“It was great, but I’m a little tired. I’m going to go lay down in my room, will you wake me when dinner is ready?” I asked.

“Sure, should be about an hour.”

I went into my room, walked up to my bed, and plopped down face-first onto it. Shoes on, feet hanging off the end. Time to get a quick nap in before dinner. I was beat.


It all started the week before when, at dinner one night, I asked my father what he did all day. My dad had a vending company — he was the first entrepreneur I knew, and likely the reason I became one later in life — and he would leave early and come back that night, usually by dinner time but sometimes later. I knew the gist of what he did, but I was curious about what exactly he was up to for that long.

Given that it was the summer, I asked if I could work with him for a few days the following week. It sounded like fun, plus I could use a little spending money.

And that is how I found myself leaving with my dad at 5 am the following Monday. We quietly left the house, trying not to wake up my mother and three sisters, and climbed into his van. A friend had asked me if I was worried about working such a long day. I confidently replied, “Are you kidding? I’m 16-years old, and he’s an old man. You don’t think I can keep up with him?”

We had a great time. The job essentially consists of driving to the warehouse where all the product is stored — cases of soda (I can say soda, I was born in Chicago) and boxes of chips, crackers, and candy bars — and loading them into the truck. Then you drive to the first stop and make your way to the places where they have their vending machines.

Sometimes there would be a note taped to the machine, explaining some grievance or another (I pushed the Coke button but a Diet Coke came out, the change shorted me $.05, etc.), but most of the time it’s a simple job. Open the machine and assess what needs to be replaced, remove the cash/coins, go back to the truck and load up the product on a rolling dolly, bring the product back to the machines, and fill ’em up.

And that’s what we did all day. I remember impatiently waiting for my dad to announce it was time for lunch, not wanting to share with him that I was extremely hungry, whereas he didn’t seem to be hungry at all. He didn’t have breakfast, how was he not starving?! When we finally did stop it was at his favorite sub place on that side of town, and it was glorious :)

A lot of the job is driving. You drive from one location to the other, all day long. Lots of downtime, with me in the passenger seat, probably jabbering all day while my dad drove, asking him all sorts of questions about anything that would pop into my head.

That’s how it went for a full 12 hours. When we got home that night, I was tired (though it turns out I didn’t know how tired) but glad I did it. And I was ready for dinner!


I could feel my mom lightly tapping me on the shoulder, saying my name.

“Jeffrey, it’s time to get up.” She, and my family, call me Jeffrey instead of Jeff. Actually, to all of them, it’s either J or Jeffrey. Even my wife calls me Jeffrey, something she learned to do when calling my house (we are high school sweethearts #howcute) and realizing that when she asked for Jeff, they’d put my dad on the phone (we share the same name.)

I could feel my mom poking me. “Mom, I think I’m going to skip dinner, I’m too wiped,” I said through the pillow, my face half submerged.

“Honey, it’s not time for dinner.” She said, “It’s 4:45 in the morning. You need to get up to leave with your dad for work in 15 minutes.”

That’s right. I came home, laid on my bed, clothes and shoes on, and didn’t move for 12 HOURS! Apparently, she had tried to wake me up for dinner but I was unresponsive, so she gave up, thinking I’d wake up at some point and make my way to the kitchen.

Here I was, a strong, healthy young man, and one day of working with my father required 12 hours of sleep just to be ready for the next day. And he did that, every day, usually six days a week.

That has always stuck with me. It takes a great deal of work to accomplish your dreams. And in the early days of my first company, Spunlogic, I worked like that. We had to because we were in our early 20’s and had no idea what we were doing. And it’s mighty hard to get a business off the ground.

Raj Choudhury and me, in my parent’s basement, in the summer of 1999. We were 23 and worked like mad to get our business off the ground.

I learned a lot of lessons from my father working with him that summer. But I think the biggest one for me was this: If you want to accomplish your dreams and goals, you have to put your head down and go about the job. Accomplishing something amazing takes hard work and there’s no way around it. An overnight success is usually years and years in the making. Years and years of hard, honest work. There are no shortcuts.

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