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Want Your Boss's Job? Here's How 8 Employees Became Franchisees. You can learn a lot from their journeys up the ladder.

By Kim Kavin Edited by Frances Dodds

This story appears in the May 2023 issue of Entrepreneur. Subscribe »

Image Credit: Zohar Lazar

At some point in their career, every worker has probably thought: I wish I were the boss.

In franchising, people often achieve that dream. They might start as a cashier, manager, or in some role at the corporate office, and then rise up to buy a unit of a brand themselves.

This is no accident. Franchises are always looking for qualified franchisee candidates who appreciate their brand and are dedicated to its success, and many of them encourage their best employees to pursue that path. It's part of the DNA of franchising. Some brands even have apprenticeship or financing programs to help their team members achieve the dream of business ownership.

So, what's it like to go from employee to boss? And what's required to make the leap? On the following pages, eight people share the biggest lesson they learned — and what enabled them to finally say what so many others want to say: "I'm the boss!"

Related: 10 Tips to Go From Employee to Boss, From Franchisees Who Did It

Lesson 1: Ask for more.

Sam Cleavenger's first job, at age 16, was with Jeremiah's Italian Ice. He worked his way up from prep boy to general manager and then marketing manager for the brand. When he turned 24, he partnered with his dad and opened a store of his own. Today, he's working on opening more stores and has 12 partners underneath him opening stores, too.

"Something that separated me from my peers would be always asking what you can do to excel," he says. "I would always ask my manager what I could do to have more responsibility. Before I became a general manager, I said I felt like I was doing great, and I wanted something more. I said I wanted to take on more leadership. I think it's the simple fact of asking. A lot of people sit back and wait and think people are going to ask them. I think you have to vocalize that you want to grow."

Lesson 2: Be creative, within boundaries.

"Everybody has their own creative style," says Bonnie Alcid. But as she's learned, creativity alone won't drive success. It must be focused and harnessed.

For example, she started her career in design and printing, but really started flourishing once she became the aquatics director for British Swim School. In that role, she says, she was able to think creatively, but toward a very focused goal — helping craft lesson plans for new franchise owners and their aquatics directors. Then she became the school's first franchisee, and creativity took on a whole new meaning.

She learned to hire people who can have fun, and then teach them how to be instructors within the school's boundaries. "I can teach a child how to swim, and I can teach an adult how to deliver a swim lesson," she says, "but it's their personality that's going to be able to come out and connect with kids and make them successful."

Related: Are You Ready to be the Boss of Your Own Restaurant Franchise?

Lesson 3: Grow alongside everyone else.

Tracy Welsh has grown a lot since the pandemic. But she's also realized: If she's the only one growing, she's failing.

Her journey began at Massage Heights, where she was the director of two locations. Both had to shut down at the beginning of the pandemic, and she worried about losing her job. Then, to her great surprise, her boss presented her with a different opportunity: Would Welsh want to buy the franchises where she worked? "I thought, My gosh, there's no way that this could ever happen," Welsh says. She was worried about financing, but after meeting with a bank, she realized she could do it.

"It made me grow in a way that I never thought was possible," she says. Then, as she built her team, she realized she was now in a position to help others grow too. "You can't just grow yourself," she says. "You have to have the mindset that you want to grow other people at the same time, growing employees, growing guests, growing members. Doing the same old thing and never changing it up is not the way to go as an entrepreneur. You have to grow and evolve."

Lesson 4: Make smart lease deals.

Ivette Escobar was assistant to the founder of Sweet Paris Crêperie & Café in 2012, and ultimately became the brand's chief development officer. When she and her husband opened their own location, she knew the lease terms were a key — because if she couldn't control the environment her business was in, she couldn't ensure its success.

"We will not take a location that will not let us do our facade," she says. "If they just want us to put up a sign, we say no." If you're looking for a space yourself, she has advice: Ask for tenant-improvement money to upgrade the space. "If it's a second-generation space, they give you less money, but that's where you have to have a really good broker to negotiate and advocate for you, to show them what you'll be doing for them and the traffic you'll be bringing, so their investment will pay off. If it's a first-generation space where it's brand-new construction, or a shell with four walls and you're going to be doing absolutely everything inside the space, that's where you can negotiate more."

Image Credit: Zohar Lazar

Lesson 5: Be the start of a virtuous cycle.

Joe Jaros started delivering for a Marco's Pizza in high school, became a shift manager at 18, and told the owner he wanted to become a franchisee at 21. Eventually, they became partners — and Jaros now owns five stores. Now he wants to keep the cycle going, by being the boss that helps the next generation of franchise owners thrive.

"I decided that I was going to have my own apprenticeship program where I take great operators and turn them into franchisees," he says. But he does it in a very particular way: He selects some of his best employees and helps them buy a piece of his own stores. To him, it's just good business. "If it's going to take me seven years to pay off a store, and the average general manager lasts about a year, I'm taking a lot of chances," he says. "If I know I have a great operator to last the whole seven years, my risk factor is much lower. I figured, if I just make a little less on each store, but I mitigate my risk, I'm going to come out ahead in the end."

Related: Is Business Ownership Right for Me? 4 Questions to Consider Before Taking the Plunge.

Lesson 6: Take smart risks.

Kelli Amrein had spent years in childcare, including director positions where her job was to manage teachers and schedules. After she joined the staff of Celebree School in 2011, she eventually got to see the business side. "They gave us full access to payroll and budgeting and all the financial reports that we could analyze to see where the business was growing," she says. "I really liked that challenge."

When Celebree started franchising, she was 41 with three kids — but she took a chance and became the brand's fourth franchisee. "I really would not have taken this leap if it was in an industry that I didn't know enough about," she says. "I knew all of the risks that happen inside the building, outside the building, the marketing, how many hours a day it would take to do things. I knew I'd have to be available to answer questions after-hours — I knew the risks, I knew the industry."

Lesson 7: Ask for help when others won't.

Matt Peters was 16 when a friend got him a job knocking on doors, offering homeowners a free estimate for Weed Man's fertilizer and weed control. At first, it was a bust — he was too socially awkward and didn't know how to sell. "I had to fall flat on my face a number of times," he says.

Instead of giving up, he started asking others for help. That included talking a lot to the supervisor who drove him and his fellow salespeople around. By taking their advice, Peters blossomed into a winning salesman — and at 24, he bought his first franchise. Today he's 32 and owns two locations. "I still see other people that I think are much more talented than I am," he says, "but I learned from good people who were patient enough to teach me and cared enough to give me advice and feedback and coaching. They either saw potential in me or encouraged me to do it and supported me."

Lesson 8: Make data-driven decisions.

Austin Clark was playing college football and had just finished his kinesiology degree when he had a career-ending wrist injury. So he changed paths: He got an MBA, became general manager at D1 Training's headquarters, and then eventually went on to become a D1 multi-unit franchisee.

How does he grow his business? By constantly tracking key performance indicators: "Say, marketing: I know what my cost per lead is, my cost per 1,000 impressions, my funnel converts, the percentage of my customers that come through the marketing funnel and end up scheduling with us. By tracking those KPIs in the data, and being in a franchise system with other people tracking those same things, I can see the areas where we're struggling. I can lean into the franchise and see who has figured those marketing pieces out. Who's done a really good job generating more leads for less dollars on Facebook and Instagram? I can then go and look for people who are great at that."

Related: Find Out Which Brands Have Ranked on the Franchise 500 for Longest, Earning a Spot In our New 'Hall of Fame'

Kim Kavin was an editorial staffer at newspapers and magazines for a decade before going full-time freelance in 2003. She has written for The Washington Post, NBC’s ThinkThe Hill and more about the need to protect independent contractor careers. She co-founded the grassroots, nonpartisan, self-funded group Fight For Freelancers.

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