Last year marked a record-breaking period for small and midsize businesses (SMBs), with over 5 million new business applications submitted. This milestone highlights the passion and entrepreneurial spirit of individuals, something I am quite familiar with. Owning and managing a small business is incredibly fulfilling, yet it comes with its own set of hurdles. My personal journey with a children’s toy and clothing retail business taught me essential lessons that have been crucial in my roles with major brands like LinkedIn, Yahoo!, and now BILL.
At BILL, I frequently engage with SMBs like Dagne Dover and Joe Coffee, organizations that continually inspire through their innovation and resilience. My experiences often take me back to my days as an entrepreneur, pondering what I might have done differently or wished I had known from the start. If you’ve embarked on the entrepreneurial path in the past year, you’re in for an exciting journey, albeit with some challenges. Here are four insights I wish I’d had when I started out:
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Being your own boss offers flexibility—but it’s not always flexible. You might think of entrepreneurship as a ticket to a flexible lifestyle, but running a business can be all-consuming. Without proper systems and safeguards, the burden of decision-making can become overwhelming. When I fell ill and couldn’t open my store, I had to choose between my business and my health. To avoid being trapped in my business, I needed to create a flexible business model, which included building a reliable team, establishing processes that functioned independently of me, and mastering the art of delegation. By putting these systems in place, I could balance my personal life without hindering business growth.
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Building a strong network is crucial. In business, like in life, relationships are everything. I initially underestimated their value but soon realized how crucial they are for growth and success. As I engaged more with the business community, my network became a vital source for recommendations, support, and expanding my customer base through word-of-mouth referrals. Beyond free marketing, this circle of peers provided insights and advice that were invaluable in dealing with customer issues, choosing the right tools, and strategizing community engagement efforts.
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Expect to make mistakes. Mistakes are inevitable, and at times, it felt like I couldn’t get anything right. Although research and planning are important, real-world feedback and experience are invaluable. "Trial and error" is a natural part of any business journey because most of us start without complete information. The greatest lesson I learned was making confident decisions despite incomplete data—a skill that has improved my career significantly. Don’t dwell on what you don’t know; instead, learn to trust your intuition and make informed decisions. Mistakes are part of the process, but repeating them is not. Learn quickly and adapt.
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Innovation doesn’t have to be costly but should be impactful. Staying competitive requires innovation, which can take various forms, especially enhancing customer experiences. It’s more about creativity than massive financial investment. For example, in my business, we launched a loyalty program with physical cards instead of a tech-based solution to test its appeal first. This approach turned out perfectly without needing higher expenses. The key to differentiation lies in understanding evolving customer demands and uniquely meeting those needs.
And as a bonus, the experience of running your own business is unparalleled. While it’s hard work, it’s also hugely rewarding. Managing different roles can be stressful but provides exceptional learning opportunities. This is partly why I joined BILL—my career has been shaped by my experience as a small business owner, and working closely with other SMBs allows me to witness and be inspired by their journeys. Each of those 5.5 million new business applications tells a story of innovation and ambition, stories that I look forward to following for years to come.
