Hats, Villages, and Failures: Report Reveals the Shared Experiences of Entrepreneurs

According to the March 2024 American Express Trendex: Small Business Edition, which surveyed 1,127 financial decision-makers from small businesses, entrepreneurs share a handful of defining experiences. The survey revealed that despite the differences each business owner faces in their unique journey, there are many common growth-mode challenges that exist across industries. To better understand what those challenges look like, I spoke with a few small-business owners who shared their perspectives:

The Necessity of Many Hats

The survey found that a majority (87%) of founders agree that “entrepreneurs wear many hats.”

Small-business owners like Joel Wolfe, president of the outsource customer service agency HiredSupport, concur with this statement. “Juggling multiple responsibilities requires wearing many hats,” says Wolfe. “My hats are engraved with responsibilities such as shortlisting and interviewing candidates and overseeing social media campaigns.”

Erica Easley is founder and CEO of the sock brand Gumball Poodle. As she sees it, small-business owners wear many hats by necessity.

“There are really only two options for owners who want to stay in business,” says Easley. “Wear whatever hat you need to at any given time to keep the business running – this is exhausting – or be so good at wearing a single hat that you build up enough capital and goodwill to hire folks to wear the hats you don't want to or shouldn’t wear – this is very hard.”

In the beginning, you will likely be wearing all the hats, agrees Aron Ezra, chairman of the software company Plan A Technologies. “So many things go into building a company,” he says. “You need to get the word out to potential clients, earn commitments from those clients, and actually do the work. Not to mention all the less flashy items on the agenda, like paperwork, which there is a lot of.”

While juggling many roles can be overwhelming, many entrepreneurs find there are benefits to multi-tasking.

“Wearing multiple hats helps you understand your business, which you must do before you can grow,” says Stella Guan, founder of Path Unbound, a UI/UX design school. “By wearing many hats, you learn very quickly about the needs of your company. Then later, when you have more money, this knowledge becomes crucial in helping you hire the best people.”

Entrepreneurs find that wearing many hats has its challenges, though. This includes struggling with burnout.

“We are all human beings with limitations regarding how much we can do on a given day,” says Guan. “At some point, in order to avoid burnout, you must choose the most important hats to wear and find creative ways to delegate some tasks.”

It Takes a Village to Build a Business

The report showed that nearly 8 in 10 (79%) of small businesses agree it’s a myth that “true entrepreneurs do it alone.”

“It takes a village to build a successful business. No entrepreneur succeeds in isolation,” says Cache Merrill, founder of Zibtek, a custom software development company. “Our village includes dedicated management team members, supportive mentors, and a network of industry peers. Collaborative efforts and diverse insights have been pivotal in helping us navigate challenges and spark innovations with our operations.”

According to Quynh Mai, CEO and founder of Qulture, a digital marketing agency, the idea that entrepreneurs succeed alone is a myth reinforced by society.

“We tend to give all credit and success to the vision of one person,” says Mai. “You don’t hear about their strong management teams or dedicated workers. We may want to idolize successful people, but the truth is that no one gets there alone. To be successful, you need a strong, dedicated, and trusted team to help guide you and grow your company.”

"We may want to idolize successful people, but the truth is that no one gets there alone. To be successful, you need a strong, dedicated, and trusted team to help guide you and grow your company.” —Quynh Mai, CEO and founder, Qulture 

Serial entrepreneur Thomas Phillips has found surrounding himself with the right people to be his key to success.

“Initially, you might handle everything yourself, but as your business grows, that's just not feasible,” says Phillips, founder of Pet Portraits and DTC SEO Agency. “My network includes my core team that manages the day-to-day and extends to mentors and entrepreneurs who offer guidance and inspiration.” 

Delegation may not always be easy for the entrepreneur who starts out solo, but it’s a necessary transition, believes Phillips. “One of the biggest challenges is moving from doing everything yourself to being a leader who empowers a team,” he says. “This shift to delegation is difficult but important.”

Failure Is Necessary for Growth

Survey results show that nearly 7 in 10 (69%) of small businesses agree that “failure is necessary to grow and become resilient.”

For Paul Gunn, founder and CEO of KUOG Corporation, a military supplier, failures experienced with a previous venture helped him succeed with his current company. “The former company I co-founded went through a challenging exit,” says Gunn, an entrepreneur since 2008. “This taught me to move more swiftly and strategically.”

Failure may be painful but “negative experiences can spur positive growth,” agrees Robin Albin, founder and brand strategist at Insurgents, her second branding agency, which she launched seven years ago.

“Failure is a shock that can provide you with the greatest opportunity to leap forward and achieve things you never thought possible. I’ve failed numerous times in business,” says Albin. “My biggest mistakes are often attributed to my overzealous enthusiasm. A few times I’ve pushed clients beyond their comfort zone and they wound up bailing. Since then, I’ve learned to read the room and strongly present without becoming pushy.”

For Sacha Walton, CEO, speaker, and business strategist at SWI Management Group, which provides professional business solutions in event planning, failure may not be welcomed, but it’s necessary to develop a key ingredient to small-business success – resilience.

“There are lessons entrepreneurs can learn from failure, or what I call the catapult,” says Walton, who started her company 20 years ago. “Failure has a way of pulling you back so that you have a clear hindsight view of what went wrong. Resilience is born from the strength found only by failing. When you identify what went wrong and adjust and correct your course accordingly, you soon find what you thought was impossible is possible.”

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