Mark Cuban, Barbara Corcoran and Other Successful Entrepreneurs’ Best Small-Business Advice

Mark Cuban
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Mark Cuban is a super-successful serial entrepreneur now, but he started out as a small-business owner with a lot of drive. And it’s important to remember that many of the most successful businesses out there started out small and grew over time. So, how did the people behind these businesses get the motivation to turn their ideas into a reality? I asked Cuban and other successful business owners how they got their inspiration to strike out on their own, and what they learned from their past jobs and experiences that helped them when starting their own thing. Their insights might be the inspiration you need to start that small business you’ve been dreaming of.

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Mark Cuban: Serial Entrepreneur, Dallas Mavericks Owner and ‘Shark Tank’ Shark

“[I was inspired to start my own business by] my parents telling me that if I wanted something, I had to figure out a way to earn the money for [it]. Whether it was selling garbage bags, selling baseball cards to kids in the neighborhood or whatever, I learned early. I learned what not to do from the jobs that didn’t work out for me — how to treat people, how sales cure all, how the fancier a company or person tried to look, the less productive they probably were.”

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Barbara Corcoran: Founder of The Corcoran Group and ‘Shark Tank’ Shark

“A lot of people think you have to have a lot of knowledge to start a business. I had something far more important than that — I had a dream. I had a clear image of who I wanted to be: I wanted to be the queen of New York real estate. The world was owned by the old boys, rich guys that had inherited their businesses from their father and their father before. But somehow in my little mind I thought, ‘I’m going to be the queen of this town in real estate.’ And I moved toward it and moved toward it until one day I was written up in New York magazine, and they called me ‘the queen of New York real estate.'”

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Vera Wang: Founder of Vera Wang

“I always sort of dreamed of being a fashion designer, and I thought, well, if I don’t try it now, I’m never going to be able to do it. So I went to Ralph Lauren through my connections to Vogue and became a design director for all of women’s [clothing] there. When I saw what it takes to build that kind of empire, if I had been sane, I probably would have stopped there. But I scheduled my wedding and I started to look for the dress. I couldn’t find anything I wanted. I was 39, which [today] doesn’t seem that old for weddings but when I got married in 1989, it was. I just felt sort of ridiculous running around bridal departments and things like that. It was my father, who, when he saw me going through this just to find a dress, said, ‘I think there’s probably a serious business opportunity here.’ He encouraged me to leave Ralph and start my own company. Here I am at 40, married and founding my own company and also trying to become a mom. It was wild.” (As told to CNBC)

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Richard Branson: Founder of Virgin

“Like a lot of entrepreneurs, I was never thinking that I was going to become a businessman. My wish was to be editor, not publisher. But if you want to be an editor and you want your magazine to survive, you got to get out there and sell the advertising and worry about the distribution. So in a sense, I became an entrepreneur by mistake just in order to make the magazine survive.” (As told to Inc)

Kathy Cano-Murillo: Founder of Crafty Chica

“When I launched my brand, Crafty Chica, and saw how well it was received and how much I loved working on the business, I knew if I built a financial strategy around it, I could use it as my full-time career.”

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Ric Edelman: Founder of Edelman Financial Engines

“As a young couple in our 20s, my wife Jean and I sought help from a financial advisor in our efforts to buy a home. He told us to lie on our mortgage application — essentially, to commit a felony. That incident 36 years ago is what spurred us to establish our own financial planning firm: to protect others from such experiences.

“Jean and I had some past experiences that actually taught us what not to do in business. That same financial advisor that told us to lie on our mortgage application refused to interact with Jean. He would only deal with me. His sexism was infuriating to both of us. As we developed our own financial planning practice, we committed to working uniformly with couples and treating both spouses with equal respect and attention. We also decided to build our firm around financial education. Back then, the only source of information available to consumers about real estate, credit, investments, mortgages and insurance came from the companies, brokers and agents who were trying to sell that stuff to them. That’s a problem! So Jean and I decided to teach ourselves about personal finance and then show others what we learned. We helped them put their knowledge into action, in a manner serving their best interests. We wanted to provide a safe haven for consumers, a place of protection against the misleading and manipulative sales tactics that are all too common in the financial services industry. We extended that safe haven to the workplace as well. Showing the same care, concern and respect for our planners and staff as we do our clients allowed us to recruit and retain the best employees. And happy employees make sure clients are happy, too — and happy clients and staff tend to never leave. Everyone wins.”

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Sophia Edelstein: Founder of Pair Eyewear, Recognized by Forbes 30 Under 30

“During my senior year of college, my co-founder and I were sitting in my college dorm room when he started telling me about his experience wearing glasses. From his own story, we realized that glasses felt more like a uniform than an accessory that encourages self-expression. In the beginning, we never thought that we were going to start a company, but rather, we wanted to solve the problem of creating a more personalized and affordable glasses product. We began creating prototypes by hand and people started asking us, ‘When can I buy this?’ That was the moment when I felt the pull of entrepreneurship and started thinking that this could become a company. We have grown a lot since then, raising over $13 million in funding and growing to a team of 33 full-time employees.

“Both my co-founder and I started Pair as students at Stanford. While we didn’t have many previous full-time job experiences to pull from, I loved the interdisciplinary nature of Stanford’s curriculum. In group projects as an undergraduate, I could be paired up with an engineer, a sociology major and a biologist. I wanted to create a similar environment at Pair where cross-functional teamwork was core to our product innovation. We highly encourage horizontal collaboration of our staff, bringing together design, marketing and customer service through regular breakouts and brainstorms daily.”

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Kathy Goughenour: Business Coach, Trainer and Founder of Virtual Expert Training

“I was 40 years old and had invested nearly 20 years in a Fortune 500 telecommunications company where I was continuously overlooked for promotions. At one point, I asked what I needed to do to be considered and they told me I needed an MBA, so late in my 30s I went back to school to get that degree. I was overlooked again, and this time for someone who didn’t have that degree. That person was also younger, and so I began to think ageism was also at play.

“When I inquired about being overlooked at that time, my boss finally told me the real reason I would never be promoted was because I laughed and smiled too much and no one took me seriously. This kind of environment, and the stress and unhappiness of this corporate job began to take its toll.

“I began having chronic debilitating migraines which landed me in the ER multiple times. On one of those ER trips that was particularly terrible, I thought, ‘I need to do something else or this job will kill me.’ Before that moment, I hadn’t considered the entrepreneurial path. I thought the only secure work was to stay at a corporation until retirement. But with continuously being overlooked and undervalued, made to feel I was only capable of certain things, feeling awful about myself as a result and the added declining state of my health, I decided it was time to take charge of my own destiny and create success on my own terms. So six months after that pivotal ER visit, I walked into my boss’s office, handed over my resignation and walked out to start my own business.”

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Adam Green: Co-Founder and CEO at YieldX and Co-Founder of Moneylion

“There wasn’t one specific spark that led me down this path, but rather a framework or perspective that brought me to where I am today. I was always intrigued by people that carved a unique path in their field. I don’t view the entrepreneurial mindset as something exclusively related to business. I am a huge fan of the creative arts — especially music — and was always drawn to artists who took an innovative and distinct approach to cultivate their unique value proposition. I happen to be driven by the problem-solving components of the business world and therefore my entrepreneurial medium is starting companies that help solve big problems in markets I understand.

“The most impactful experiences I’ve had in the past are the ones that I do not want to replicate in the future. You can read any number of bestselling books about how businesses succeed at a certain point in time in a certain market cycle, but culture drives companies in ways that can’t possibly be effectively captured in narrative form. Seeing models or behaviors that don’t work has influenced my success and enabled me to avoid pitfalls and retain flexibility.”

Read: Where 51 CEOs Went to College

Colin Walsh: Founder of Varo Bank

“I was inspired to become an entrepreneur after over two decades working in larger banks and financial services companies. I saw firsthand that the banking system only works well for people who already have money. People without high income or wealth are often left behind and shoulder the bulk of the transaction fees and charges at banks. I knew that technology, a better business model and a core social impact mission could make a real difference for millions of American consumers — so Varo was born.

“Building from my past experience, I was able to leverage how to build products and digital experiences that customers love, how to rapidly grow and scale a business, how to attract and retain the best talent, and how to navigate the regulatory process. All of these have been key to Varo’s remarkable success since launching in 2017.”

Ksenia Yudnia: Founder of UNest

“I never thought I’d be an entrepreneur and I certainly didn’t take the traditional path. I started UNest because I saw a real need from a personal and professional standpoint. While working as a financial advisor, I realized that parents’ number one priority is saving for their children, but the industry failed to recognize this. There wasn’t a simple, affordable solution available to all parents, regardless of income or background, and as someone who graduated with $180,000 in student debt, I understood the problem on a personal level. That’s what prompted me to start UNest.

“When I was working as a financial advisor, friends and family were constantly asking me how to open accounts to save for their kids’ education. I would hand them pages of paperwork, and the majority of the time they didn’t end up opening an account. Young parents are accustomed to using apps like Venmo or Robinhood, and the current system is majorly outdated. I knew I wanted to create a solution that was mobile-first, simple and affordable for anyone.”

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Gabrielle Olya contributed to the reporting for this article.

Last updated: June 30, 2021

About the Author

With eight years of experience working in the personal finance space at GOBankingRates, Jaime Catmull has amassed an extensive network of financial influencers and experts. Now, she’s tapping that network to get the real scoop on how you can live your best financial life and increase your wealth.

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