How 5 Founders Developed Their Entrepreneurial Mindsets
“I always knew one day I was going to have my own business,” says Janelle Doyle, who left her banking job to start It’s Poppin! Gourmet Kettle Corn, a fast-growing specialty popcorn company located in Charlotte, North Carolina. “I didn’t know what it was going to be, but it would be enough to sustain myself and my family,” she remembers. “I’m not going to work for anyone else for the rest of my life.”
Whether you’re starting a business, changing your business model, or trying to scale, developing an entrepreneurial mindset can help you hit reset so you can achieve what you set out to do, just like Doyle. Today, Doyle has turned her popcorn business into a runaway hit, selling out of popular flavors, landing partnerships, and she’s now eyeing a second location.
What is an entrepreneurial mindset?
Connected to the idea of business resilience, an entrepreneurial mindset is an outlook that enables business owners to succeed. It’s a way of thinking that allows you to see opportunities where others can’t, and spin up creative solutions that solve the problems you started your business to fix.
Developing an entrepreneurial mindset isn’t something you learn in business school — it’s what you pick up when going through the ups and downs of running your own business.
So how do you train yourself to think more like Doyle and other successful business owners?
Developing an entrepreneurial mindset: 6 characteristics
We talked to five entrepreneurs to hear how their thinking has shifted since they started their companies, and their advice to others hoping to level up their entrepreneurial thinking skills.
Staying grateful for the mistakes
When Bethany Dorn first tried to start a business, it didn’t work out. It was only after she was laid off from her recruiting job during the pandemic that she decided to give business ownership another go. And that rocky experience paved the way for Dorn to start Briggs and Brighton, a popular custom jewelry company located in South Carolina.
“Trying and failing that first time … got me to where I am today,” Dorn says. “You learn from [your mistakes], and you’re thankful for those mistakes because you know you won’t make them again.”
Knowing when to let go
Jae Hermann is the owner of Jae Hermann + Co., a consulting business that provides empowerment coaching, motivational speaking, and professional copy editing services. When Hermann first started consulting, she became overwhelmed because she took on too much — so Hermann shifted her mindset to protect more of her time.
“When you’re first starting, it’s like I’ve got to do everything now, I’ve got to do everything yesterday and it’s all on me,” she says. “As I’ve gotten older, releasing attachment to that has helped. The money will always be there.”
Dorn has also had to go through the exercise of cutting back her workload. During the holidays her bracelet company got inundated with orders, and at the time, she was the only employee. “I was staying up until 4 a.m. getting orders done and it was starting to affect my health and my family,” she remembers. “I had to dial it back.”
Hiring employees can help you reset and spend time on the areas with the highest ROI. But it can be difficult to delegate work to others when you used to run the show. “Knowing when it’s time to turn to someone else has been hard for me,” Dorn admits. “But letting go of control and allowing people to help me, and finding the right people to help me, has helped tremendously,” she says.
Supporting other entrepreneurs
Since launching her business, Doyle has had more motivation to support other business owners. “I always used to go to farmers markets, fairs, and festivals, but now almost everything I buy is local,” she says. Supporting local entrepreneurs not only helps you build community in your area or industry, it can also help you discover new opportunities that benefit your bottom line.
For instance, Doyle uses local honey from suppliers in North Carolina along with seasonings from local spice vendors, making her gourmet popcorn even more of a hit. “Now it’s like, I need this, let’s see what the local farmers market has, or a local boutique to get this or that,” she explains.
“That local piece has definitely changed my mindset,” says Doyle. “I encourage everyone to shop local. Keeping the dollars in your local community is the greatest thing ever.”
Another way to support fellow entrepreneurs — and get into an entrepreneurial way of thinking — is by teaming up to reach a common goal. David and Danel Betelu, the owners of tea salon and patisserieMaison Danel, partnered with a beer bar in their building so they could get a permit to build a shared parklet for outdoor seating.
“This is probably something that we wouldn’t have discussed before, like, ‘Oh yeah, we have a lot of seating in our tea salon so have people come over and have sushi or have a beer,’ like that just didn’t make sense,” says David. “But now, those are the conversations we’re having. We’re all small business owners. The more success that we see in the neighborhood, the better it is for everybody.”
“I have always been obsessed with everything business,” says Bethany Dorn from Briggs and Brighton. “I listen to business podcasts, read business books, articles, that kind of thing. I did that even before this took off, and I think that really equipped me with a lot of the knowledge I have to be an entrepreneur now.”
Immersing herself with business content has opened Dorn up to thinking in new ways, and it’s something you can do, too, with a variety of business resources, from tools and templates to perspectives from other business owners. “You never know what you’re going to pick up from using resources like that,” says Dorn. “I’ve definitely used all the tips and tricks I’ve learned over the years in this business.”
Looking for the best-case scenarios
Jae Hermann, the owner of Jae Hermann + Co., encourages entrepreneurial thinking for herself and her clients by borrowing a lesson from the world of improv comedy — the concept of “yes and.” It’s a concept that inspires people to build off of ideas, saying “yes, and …” instead of turning things down.
“I even say that to my clients,” Hermann says. “Like what do you think I should do with it? Let’s try it and see. What’s the worst thing that could happen?” she explains. “I’ve changed that to what’s the best thing, what’s the best-case scenario if you try this? Let’s do it and find out.”
Focusing on the best-case scenario allows you to take risks because you aren’t scared about what happens if your idea doesn’t work. You already have another plan. Like Hermann says to her clients, that mindset shift also allows you to develop an adventurous spirit in knowing that you could achieve something if you simply give it a go.
Centering yourself with your reason for starting up
“I always wanted to be an entrepreneur. I always wanted to work for myself,” says Doyle from It’s Poppin! Gourmet Kettle Corn. “People in my family didn’t have their own businesses, but they encouraged their children to do what we wanted, be who we wanted, and not let anything stop us.”
Having that North Star made Doyle’s decision to start her business easier since it was almost already made. So she was able to jump on the right opportunity when it came up. And when the full-time opportunity to work on It’s Poppin did come up, Doyle quit her job.
“It really did take courage for me to just step up there and say I’m not going to do this anymore. I’m going to depend on myself and nobody else,” she remembers. Her entrepreneurial mindset kicked in when she remembered who she was doing it for. “You’re always going to think, am I making the right decision? But for me, if I’m doing it for me, it is the right decision. And nobody’s going to work harder for my business than I am.”
Hermann also gets into that entrepreneurial mindset by remembering why she’s in business. For each new client or project she takes on, Hermann reminds herself of the value she’s giving and getting out of the relationship, who she’s helping, and why it matters. “So no matter what different business vehicle I’m in, that still remains my core,” she says.
It doesn’t matter if you’re on your first business or tenth, developing an entrepreneurial mindset can help you unlock new ideas and get you out of patterns that slow you and your business down. And like Doyle and the other entrepreneurs we talked to, it can also give you the fire that finally helps you make a big life change.
Square has the tools to run your business — on your own terms. To help celebrate businesses paving their way forward, we partnered with Forbes on the Next 1000 initiative to spotlight bold entrepreneurs and share their most valuable lessons. By sharing firsthand experiences, we’re helping businesses celebrate resilience, build skills, and explore what’s next. See how Square works, and get more expert guidance for the next era of small business.