12 Unexpected Challenges Real Entrepreneurs Overcame

As an entrepreneur, what is one unexpected challenge you faced and how did you overcome it?

To help you learn from unexpected challenges entrepreneurs have successfully dealt with, we asked established entrepreneurs and CEOs for their best insights. From raising capital to delegating tasks effectively, these shared experiences may serve to prepare you for unexpected challenges and how to overcome them as an entrepreneur.

Raising capital

Never underestimate how hard it can be to raise capital at first. Raising capital as you start out will be one of your biggest challenges. You have so much to prove, and probably so little to show potential investors. An effective leader will seek out multiple funding sources in the beginning, building connections and exploring all the available resources. Once you master raising capital, many of your other internal challenges will seem easy.

Carey Wilbur, Charter Capital


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Hiring and managing the right people

A successful entrepreneur knows the importance of hiring and managing the right people. At the same time, that can be easier said than done, especially when you’re just starting out. Like it or not, there’s going to be a bit of trial and error, and your hiring needs are going to evolve. We found that focusing on cultural alignment helped us recruit and maintain the best talent for ours and our clients’ needs.

Jon Schneider, Recruiterie

Developing and maintaining partnerships

In order for your business to thrive, you’re going to have to make a lot of friends. That isn’t as easy as it sounds, mostly because not everyone is aligned with your goals, mission and vision. Research your industry, or even fields adjacent to your own. Examine the companies and people you want to partner with, and then reach out. Developing and maintaining partnerships is an attribute all successful leaders share.

Blake Murphey, American Pipeline Solutions

Dealing with international tastes

Our business is part of the travel industry, and though we were initially focused on the U.S., when we expanded outside our borders, we soon realized that we had a major challenge when it came to marketing in other countries. We did not realize that promotional tastes change when you cross borders, and quickly found out that what worked in the U.S. market did not necessarily work in international ones, resulting in many ineffective campaigns. 

To tackle this issue, we created smaller teams to research desired markets before we entered them, and partnered with local businesses that gave us insight into language, culture, popular trends and other details, in order to tailor our promotional efforts. By taking a global perspective for our marketing efforts, and seeking local insight as opposed to solely using our own national view, we were able to overcome these marketing challenges, and succeed internationally.

Cody Candee, Bounce

Time management

The biggest unexpected challenge for me as an entrepreneur has been time management. When you run your own business, there are a million things to do, and you can’t do them all at once. This is the challenge because you can’t let anything slide. Over time I’ve found that I just need to schedule time for important tasks and make sure those tasks are completed. If a task can be delegated, that’s an ideal solution.

Jane Kallinger, Sewing From Home

Fraud and due diligence

My company became a victim of fraud when a client did not pay us for the services we rendered. I called the client and advised him to pay up. I also pointed out that I was planning to refer the matter to my lawyer. But this didn’t work and I was still short $4,000. I sought information from some friends, and they directed me to a recovery expert. I contacted the expert, and he recovered my money, plus a substantial amount in legal fees. I had to pay a flat 10% of the amount that was recovered and this brought my total payment to $10,000. However, the recovery expert warned me not to fall prey to fraudsters again. He advised me to do a thorough due diligence check on clients before doing business with them, and I have been doing that ever since.

Tomoko Harris, WinnerWinner


Common Mistakes Entrepreneurs Make in Their Business Journey

Values are often tested

Entrepreneurs are always flirting with disaster. Between taking calculated risks and pushing relentlessly toward a distant vision, it comes as no surprise that almost half of all U.S. businesses fail after five years (LendingTree). When leaders are constantly on the edge of success or failure, values come into question. How do you define yourself, and how do you think of success? In the business world, your values and identity are always being tested. Complicated trade-offs that aren’t learned in business school or written in books show up very quickly. The real world is never so black-and-white. The gritty, gut-wrenching moments are real, and you’ll wrestle frequently with your own values. The decisions you make will bring to life what ultimately are the seeds of your company’s values, and your mindset and leadership will need constant tending in order for you to build a healthy, successful organization. Humility is key, patience is paramount and a willingness to learn is critical.

Max Wesman, GoodHire

Health and financial crises

When COVID-19 began, our e-commerce stores were in an extremely difficult position since our core products are marketed toward music festival attendees. These music festivals were canceled or postponed all over the world. Although we had been preparing for a recession for several years, and we had cash built up to survive a revenue hit, we weren’t planning for a health crisis on top of a financial crisis. 

As a result, we pivoted in a couple of ways. First, we steered away from mostly festival clothing, and instead focused on other applications of our clothing like lingerie and loungewear. Second, we started designing face masks, which were a huge hit! So, if your business is struggling, think about the ways you can pivot. Our economy won’t stay shut down forever, and pivoting the right way can help your business survive, and potentially come out stronger.

Brian Lim, iHeartRaves

Not getting traffic to my site

When I started my online business, I literally had no clue on how to get traffic to my site. I could buy the traffic, but that would cost me a lot of money. I spent days doing a variety of things: building backlinks, writing articles and sending emails to people. All I got was a few hundred visitors. That was when I decided to take a step back and try to figure out a long-term strategy. Across the weeks and months, I tried a lot of things and eventually got traffic. It may sound easier than it actually is. And I had to fail a few times before getting it right. But I was willing to stick to my resolution, and that’s how I eventually managed to build up a very successful online business.

Sumeet Sinha, FinLightened

Finding consistent clients

It’s not always easy to find clients and customers especially when you’re offering a service instead of something tangible. As we focus on helping small businesses with their finances, our target audience tends to try to minimize costs as much as possible as they’re starting out. What has helped us immensely at Finance Hire when finding clients is our referral program where existing small businesses endorse our services, show results and explain how beneficial it was for their business and receive a discount for every new client they bring on. This helps not only in getting new clients, but also in retaining our existing clients, too.

Zachary Weiner, Finance Hire


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Providing value to customers as an e-commerce store

While starting my business, I found that providing SEO services to my customers took more than highlighting what my business offers them. I needed to package my services in a way that provided customers with value. After I established tiered packages for my digital marketing services, I also needed to show confidence in the service I was providing. So, I began offering free trials, started an affiliate program, and listed all the feedback I received from customers. With this, I gained more customers and attracted new talent for publishing blog posts. 

Currently, the value I provide customers is clear in every communication with potential customers. From the main page to the “Buy Now” button.

Tony Peacock, LinkDaddy

How to delegate tasks effectively

One of the biggest challenges I faced as an entrepreneur was learning to delegate tasks. When you’re first starting out, it’s easy to try and do everything yourself. As your business grows, it becomes increasingly difficult to manage everything independently. I learned the hard way that it’s important to delegate tasks to others and to trust that they will be able to handle them. Give people clear instructions and guidelines to be successful in their roles. Once I learned how to delegate effectively, it freed up a lot of my time and energy and allowed me to focus on more important things.

Michael Barr, Teleleaf

Terkel creates community-driven content featuring expert insights. Sign up at terkel.io to answer questions and get published. 


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