Powerful Insights and Wisdom from Top Middle-Market CEOs: The Early Years – First Jobs and Leadership Experiences

In Leadership Resources by Brandt A. HandleyLeave a Comment

On ROI’s Into the Corner Office podcast, we have interviewed over 150 leading middle-market CEOs from companies across industries, and the advice and wisdom they have shared with us is unparalleled. We are excited to share some of these insights with you in a new form!

One of my favorite things about interviewing our guests is hearing their backstories: Where were they born? What was their family life like? Who were their mentors? Were they entrepreneurs or business-oriented at a young age?

Every CEO got a start somewhere, and I always enjoy hearing about first jobs and leadership experiences and learning more about the origins of my guests’ interests in founding and/or leading a company.

The Ubiquitous Paper Route

Many of the guests on the show got their entrepreneurial start in the business world with a paper route, either for spending money or to save up for something big like a car or college tuition. Sean Taylor, CEO of Up To Par Management and Taylor Hospitality, remembers getting up at “five o’clock in the morning [to] deliver to probably about one hundred families” in his neighborhood, an achievement he was particularly proud of because he started with sixty families–impressive growth!

Marc Jourlait, CEO of SCRAM Systems, also remembers waking up at “an ungodly hour” to deliver newspapers in his native Toronto, an endeavor that required him to deliver papers in all weathers, but one that allowed him to make “one hundred Canadian dollars a month, which made [him] the richest man on the block.” That and other early jobs gave him “an appreciation for work and the reward of work, which is not only pride and intellectual stimulation” but also an appreciation of earning a paycheck, which, as Marc notes, “is nice.”

Paper Route Alternatives

A paper route wasn’t available to Skyler Ditchfield, CEO of GeoLinks, since he grew up in a rural area–although he told me he really did want one–so he did what any other enterprising youth would do: sold things. His cousin had a similar entrepreneurial bent, so they “sold things on the side of the road, whether it was lemonade, hot dogs, or Kool-Aid. We painted the little oak balls off trees … you name it, we sold it!” He continued his salesmanship experience selling candy, used laptops, and worked for other people–eventually deciding he preferred working for himself over others because working for yourself allows you to “really get to control your own destiny versus working for someone very much.” Entrepreneurship and being his own boss obviously suit him!

Brett Beveridge, CEO of The Revenue Optimization Companies, also did not sling papers for pocket money, but he participated in another common youth employment option: mowing lawns. Which, as he notes, was a lucrative business in his native Florida, since “grass grows fast!” Brett also was deeply impacted by the book “The Richest Man in Babylon,” which his dad asked him and his brother to read one summer. The lessons he learned from that book like pay yourself first, compounding interest, how to live within you means,” stuck with [him} and [he] recommends that book to all ages to this day.”

Regardless of how a CEO gets their start–delivering papers, selling candy, mowing lawns, working at the local fast-food joint–I enjoy hearing how they got their taste for business. It’s a privilege to hear the lessons and experiences that have a lasting impact on each of these amazing leaders. For more compelling stories, you can find the full archive of the Into the Corner Office podcast here or subscribe via iTunes or your favorite podcast player.

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