What 4 Chicago tech leaders learned from their first jobs

Andreas Rekdal

Do you remember your first job?

My first foray into the working world was at age 13, when I schlepped dead trees with outdated content printed on them around my neighborhood to drop them on people’s doorsteps. While the job itself may not have been very fulfilling, having responsibility and making my own money felt like a big deal at the time.

It got me thinking. Where did Chicago’s tech leaders first cut their teeth in the working world, and what did they learn from their experiences at the bottom rung of the ladder in the world of the gainfully employed?

We reached out to a few of them to find out. Here’s what they said:

Solstice Mobile CEO J Schwan was bitten by the entrepreneurship bug early. At age 12, he co-founded a lawn mowing business — A&J Landscaping — with his buddy, Art.

The best part: “Some great memories,” said Schwan. “We hooked up a trailer to a Craftsman riding lawn mower, put a couple old push mowers and weed wackers in the back and would drive from one customer to another going about 3 mph.”

“It was probably the best advertising we could do,” he added. “We attracted tons of customers who came outside to see what the noise was and walked up and asked us for a quote. The business scaled up very quickly.”

The worst part: “Mowing the lawns!” said Schwan. “The sales outgrew our ability to service them. Many nights we could be found with the riding mower's headlights illuminating the lawns we were push mowing.”

“In hindsight, we knew how to scale sales but not how to scale the delivery of the service. We should have recruited more of our buddies, but wanted all the money for ourselves. We ended up at each other’s throats in frustration, and the business ultimately collapsed. Thankfully we remained good friends, but we learned some valuable lessons.”

What he learned: “That any services industry can be disrupted if you think about new sales and servicing models,” said Schwan.

How the experience shaped his leadership style: “I think every experience shapes us in some way,” said Schwan. “With A&J I learned a lot about the importance of balance in a business, as well as the importance of nailing delivery before scaling sales. That's essentially what we've done at Solstice. We would not have been able to capitalize on the growth we've had these past few years if we hadn't taken the time to perfect our culture, recruiting and delivery models first.”

project44 co-founder Jett McCandless with team members at Tough Mudder

If you’re an investor looking to find Chicago’s next big tech leader, the landscaping industry might be a good place to start. Like Solstice Mobile’s J Schwan, project44 co-founder Jett McCandless also founded his own lawn mowing company when he was 12.

The best part: “Most teenage jobs are transactional, but this one was strategic,” said McCandless. “It had fewer constraints. I was my own boss, and got as much out as was put in. Even at a young age, there was a freedom to it.”

“When problems arose, I was rolling up my sleeves to come up with solutions. If there was a need to increase sales, that meant knocking on more doors and flyering more telephone poles,” he added.

What he learned: “This experience taught me what it meant to invest in an idea and build it into a business,” said McCandless. “It was rewarding to see a concept through to fruition, but it also forced me to understand the costs associated with running my own business. My family didn’t have a lawnmower for me to borrow, so I had to purchase one and take on all the costs to repair and maintain that machine. As a young kid, spending my time outside was a perk, but pushing the lawnmower on hot summer days was tough work.”

How the experience shaped his leadership style: “The biggest takeaway has been to never lose sight of where you came from,” said McCandless. “As someone who grew up with little means, work ethic and a strong determination to succeed are characteristics that I value more than anything. My experience starting companies, even small lawn mowing initiatives, has taught me that these personality traits are an essential component of winning teams.”

McCandless added that building a connected, hard-working team is one of his biggest priorities.

“Every year, the entire team — interns, executives, strategic partners, and even significant others — runs a Tough Mudder together," said McCandless. "It’s a fun but challenging experience. The race forces us to get outside our ‘work comfort zone', recognize each other’s strengths and come together to overcome obstacles.”

At age 12, VISANOW president and CEO Dick Burke got his first job picking blueberries at a small farm in Bridgman, Michigan.

The best part: “My favorite part was making my own money so I could buy records,” said Burke.

The worst part: "My least favorite part was that workers were paid based on production — by how many pounds of blueberries were picked — and not by how many hours were worked,” said Burke. “If you didn’t produce, you didn’t get paid.”

What he learned: “First and foremost, I learned about the importance of productivity,” he said.

How the job shaped his leadership style: “The owner of the farm worked alongside us and treated us fairly and respectfully,” said Burke. “Bosses don’t have to be hostile to be effective.”


Like most other kids, VelocityEHS CEO Glenn Trout had a number of odd jobs growing up — from shoveling snow and mowing lawns to making deliveries for his local pharmacy. But his first “real” job came at age 18, three days after graduating from high school, when Trout headed off to Air Force boot camp.

“We were all in boot camp for the first couple months, but after I went on to Technical School as a wideband communications equipment specialist,” said Trout, describing his  “basically a fancy radio repair guy.”

The best part: “I was from a small town and had never been on a commercial flight before leaving for San Antonio for boot camp, so the whole thing was a bit of a culture shock for me,” said Trout. “I really enjoyed working with people from all of the country and from all walks of life.”

The worst part: “As I’m sure you know from watching TV and movies, the U.S. Armed Forces boot camps put a lot of pressure on people to see how they react under both mental and physical stress,” Trout said. “I enjoyed the physical stress, but the constant mental pressure was new for me. They would constantly test you on small, simple things, and then blow up if you made a mistake to see how you would react. You were in constant fear of being washed back a week or two in training or completely washed out of the program if you made mental mistakes.”

What he learned: “In hindsight, I can see why this mental pressure is so important,” said Trout. “It is critical that our Armed Forces perform well under pressure and pay close attention to detail. You have to challenge people and train them to do the right things, even under pressure. It’s important to remember that many of the people I was training with go on to repair very expensive critical equipment like aircraft, radar and radios, so they need to be able to do these jobs no matter the circumstances, even potentially under fire.”

How the experience shaped his leadership style: “That Air Force experience gave me the opportunity to lead from a very early age,” said Trout. “During Boot Camp, I got the chance to rise from a squad leader to squadron commander at the age of 18, with many of the airmen in my squadron being well into their 20’s and even late 30’s.”

“One huge advantage for me was watching the previous squadron leader's mistakes and being able to learn from that. Over the years I’ve found I often learn as much or more from mistakes than victories.”


Images via listed companies.

Have a tip for us or know of a company that deserves coverage? Shoot us an email or follow us on Twitter @BuiltInChicago.

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