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9 Business Founders on the Lessons Learned From Their First Jobs

Aja McClanahan

Contributor at Fundera
Aja McClanahan is a financial writer who blogs regularly at and also writes for other online publications covering personal finance, entrepreneurship, travel and general lifestyle topics.
Editorial Note: Fundera exists to help you make better business decisions. That’s why we make sure our editorial integrity isn’t influenced by our own business. The opinions, analyses, reviews, or recommendations in this article are those of our editorial team alone.

When you think of your first job, what comes to mind? Some might remember drudgery, mindless tasks, and small paychecks. Others may remember the feeling of empowerment and independence upon receiving their first paycheck.

Whatever kind of job you had, there’s surely something you remember about it and there’s probably even more you learned from it. Lessons of perseverance, dependability, discipline, and even financial savvy can come from our first jobs.

We might even learn more about the type of work we’d like to avoid for life. After all, a summer of flipping burgers can be pretty motivating (or demotivating) in and of itself.

We spoke to nine business founders about the first jobs they had and what they learned that still serves them today. No matter the job, background, or type of business they have, each admits they learned something from their very first job experience.

1. Chris-Tia Donaldson, Thank God I’m Natural

Recently named one of Chicago’s 40 under 40, Chris-Tia is a lawyer turned natural hair care specialist and entrepreneur. Her million-dollar company, Thank God I’m Natural, sells hair-care products online and in major retail chains like Target. Though she still maintains her job as an attorney, she remembers what her first job taught her in the legal field.

First job: I worked as a file clerk for an attorney who specializes in social security and disability claims.”

Lesson learned: “I learned that it takes a team to get things done and that it is important to have people on the ground who can execute, keep you organized, and handle the everyday tasks that make a company run. I worked for a successful lawyer, but it was his secretary, who was extremely hardworking, who helped to keep the operation running smoothly.”

2. Pat Flynn, Smart Passive Income

This internet marketing guru is one of the web’s most inspiring success stories. Pat started his company, Smart Passive Income, after deciding to teach others to duplicate his success generating passive income online. Though his monthly income reports top out at $100,000-$200,000 per month, he hasn’t forgotten his humble roots in the “picnic industry.”

First job: “I worked at a company called Picnic People. We hosted corporate picnics. It was my first experience with customer service.”

Lesson learned: “I learned that the smallest gesture can mean the biggest difference to someone. Going an extra mile to make sure someone’s experience was great, even if it didn’t seem like they needed it. It made a great impression, and my small ‘little extras’ often made their way up to my manager, and that felt great!”

3. Allen Walton, SpyGuy Security

Allen is the man you want to call when you need spy gadgets. His company, SpyGuy Security, is an online platform that sells surveillance cameras and other security products. His seven-figure business was started three years after he left a well-paying job.

First job: “I worked as a cashier for an electronics retail store called MicroCenter (akin to Best Buy).”

Lesson learned: “The job you currently have is an audition for your next job. I was able to meet all kinds of great people as a cashier—including the kind of person that might hire you. So, do the best you can. It’ll pay off in the end.”

4. John Lee Dumas, Entrepreneur on Fire

John Lee Dumas is the founder the Entrepreneur on Fire website and host of the popular podcast with the same name. He also provides help to people wanting to start their own podcasts. His show entails interviewing people who are “killing it” in business and using novel, innovative ideas to do it.

First job: “I was an officer in the U.S. Army.”

Lesson learned: “Discipline. It’s something U.S. Army officers must have to survive and something that I found so many entrepreneurs lack. Commitment to discipline has been the differentiator to my success.”

5. Amber Swenor, Strategic Partners Marketing

Named among Brava’s 2017 list of Women to Watch, Amber runs a successful boutique ad agency, Strategies That Pay, for small and medium-size businesses. She also provides general business consulting services to entrepreneurs to help them with marketing and branding.  

First job: “My first professional job was as a telemarketer (ew, right?!) However, it taught me the foundational steps needed to later build a very successful sales career.”

Lesson Learned: Always be making calls. Always have leads in the funnel. Learn to listen and sell to customers’ needs.”

6. Nathan Barry, ConvertKit

Nathan Barry founded one of the fastest growing email service providers (ESP) for internet entrepreneurs and markets, ConvertKit. After a few successful book launches, he could never quite find an ESP that met his needs, so he created one.

First job: “My first job was at Wendy’s.”

Lesson learned: “The most important thing I learned there was how to work quickly. Working at the drive-through during a lunch rush, the goal was to get each car through in under 70 seconds on average. That meant constantly refining our systems to be more efficient.

“I later applied that to web design as I learned to code. I always pushed to reuse code and well-defined patterns so that I could write great code faster than co-workers.”

7. Allison Matulli, Legal Kid

Allison Matulli, a lawyer, is the co-founder of Legal Kid, whose goal is to empower every kid to know the law and to foster conscious young citizens.

First job: “I was a tutor-counselor for underprivileged kids in rural Pennsylvania.”

Lesson learned: “Being humble is always at the forefront of any partnership or human connection in life or in business. It has served me well in life and in business alike.”

8. Carrie Seibert, Soap Commander

Carrie and her husband created a natural line of men’s shaving products that include things like shaving cream, aftershave balm, and lip balm. The throwback packaging and all-natural ingredients are reminiscent of old-timey barbershops, setting the Soap Commander brand apart from competitors.

First job: “My first job was working in the market section of a family-run orchard where I did many different jobs, most of which involved customer interaction.”

Lesson learned: “The main lesson I learned was that no matter how busy we got, I needed to make the customer I was assisting my priority, and to ensure that he or she felt that way.

“Today, my husband and I continue that tradition by ensuring that we interact with each customer in a focused, one-on-one, customer-centered approach, whether that be in person, via email, or through the handwritten cards we include with every order.”

9. Danielle Kunkle, Boomer Benefits

Danielle is the founder of Boomer Benefits, an insurance agency specializing in helping baby boomers find the right type of health care insurance for their needs. 

First job: “My first job was working at Subway as a sandwich artist in high school.”

Lesson learned: “My manager at Subway was a high-school dropout who often wrote orders for us on the board that were full of grammar and spelling errors. I thought he would be a real dunce to work for, but he turned out to be a great manager with a knack for making people want to excel at their job.

“My lesson learned was that everyone has something to offer and don’t assume that someone is an idiot just because they don’t excel at the same things you do. Find what’s great about them and let them know that you see that in them; they will love working for you.

“Even though your first job will not likely be your final destination, it can still provide a foundation for things you’ll do later in life. Thinking back on your first job, what did you learn that still has an impact on you today?”

Aja McClanahan

Contributor at Fundera
Aja McClanahan is a financial writer who blogs regularly at and also writes for other online publications covering personal finance, entrepreneurship, travel and general lifestyle topics.