4 Biggest Challenges Top CEOs Face (and How You Can Overcome Them as an Entrepreneur)

As an entrepreneur, you face many challenges that demand your time and attention, and can contribute a large burden on your work and how you manage it. We spoke to a number of CEOs running small- to medium-sized companies, many of which have been featured in publications such as Business Insider and Inc., to name a few.

From these conversations, we gained insights into the common challenges entrepreneurs face, and how to rise above them. During our interviews, we noticed four main struggles that a majority of these experienced CEOs have encountered, including:

  • Getting the funds to grow a company
  • Prioritizing competing tasks
  • Putting the customer first
  • Staying motivated

Here, we will dive into these trends and hear from the pros about how they ensured that these obstacles wouldn’t get in the way of their company’s success.

Getting the funds to grow your company

Entrepreneurs are dreamers. They think big and go hard. But like they say, with great power comes great responsibility, and most big dreams need money to soar.

Even if you have an idea for a product or service that has the potential to be the next multimillion dollar company, it doesn’t mean that investors are going to agree from the get-go (just watch “Shark Tank” to see this principle in action).

Thus, you are going to have to really impress investors to get the funds to grow your company. Getting investors to open up their wallet for you not only requires a cutting edge idea that can make them rich, but also a person whom they can count on.

Here is some advice from the pros to help you get those investments to take your company to the next level:

“Invoke your passion in your company before meeting with investors. My passion wins over nerves for me.”

-Vivek Mehra, founder and CEO of ParqEx

“Develop confidence in your product. I used to get so nervous before meetings with investors, but now, I’m so confident in our product and our process, that all I feel is excitement.”

-Ryan Westwood, co-founder and CEO of Simplus

“I battle nerves by remembering that the best person I can be is me. In other words, investors, just like anyone else, can see inauthenticity and nothing will kill a meeting or opportunity quicker than not being who you are. Be yourself. Be prepared.”

-Matt Westgate, co-founder and CEO of Lullabot

“When you’re honest in an investor meeting and ask for constructive criticism from them, even if you don’t get the money, you will learn something you can use to make your next presentation better, or identify part of your business plan that still needs work.”

Kirk Simpson, co-founder and CEO of Wave

“Do not focus on the issue of securing funding immediately. Stop being obsessed with it. Stop for a second and figure (out) what you are trying to do in the marketplace and why your business makes sense. Take time to define and understand so you find something you strongly believe in. Then, the rest of the issues will naturally fall into place and solve themselves.”

-Ariel Cohen, co-founder and CEO of Trip Actions

Additionally, all of the CEOs we interviewed seemed to agree that it is important to have some key takeaways for the investors to remember from your meeting. Write out these objectives and make sure they are included in your presentation before heading into any conversations with potential investors.

Prioritizing competing tasks

There’s only so much that you can accomplish on a daily basis, so how productive you are really comes down to how efficiently you use your time.

So, what are their standpoints on prioritization?

“When a fire is repeating, you should stop for a second and ask what should be changed in the current process, the current product, and the current behavior of the company to prevent and alleviate repeating fires. In short, you should handle the fire and figure out what you should do next time. It is not really a process. Just address current issues to prevent them from happening as opposed to denying them.”

-Ariel Cohen

“Face prioritization challenges head-on and know how to handle them.”

-Ryan Westwood

“I schedule meetings with myself during the week. If it’s on my calendar, then I can’t be booked somewhere else. For instance, I have a quiet-time meeting in the morning, an end-of-week wrap-up meeting on Friday, and Thursdays are completely blocked off, which is my primary focus day.”

-Matt Westgate

“We believe in the old saying that plans are useless, but planning is indispensable. We spend time talking about what the priorities should be, and try to be very conscious of the tradeoffs we’re making.

To manage my time, I personally am a big advocate of the Getting Things Done (GTD) approach by David Allen. That, together with having the world’s best assistant! We start every day with a standup meeting to go through the calendar and priorities. And every quarter I revisit how I’m actually spending my time versus what I wish I was spending based on my priorities, and try to make adjustments.”

-Daniel Chait

“When you’re faced with a prioritization choice, do the math, even if it’s rough, and even if you sometimes need to use gut-level guesses in your calculations. Compare the impact that path A will have on your business outcomes, to path B, C, D and so on, and use that to inform your decisions.”

-Kirk Simpson

Many of the small business owners we spoke with mentioned that they use tools like prioritization templates, Google Calendar, Evernote and Priority Matrix to organize tasks and projects.

Putting the customer first

There’s no way you will get to the top without a dedicated customer base that loves your product or service as much as you do. So, it is vital that you establish a way to receive feedback directly from your customers.

In order for your startup to succeed, it’s critical to prioritize time to ensure that your customer’s wants and needs are being heard:

“I can’t overstate the importance of listening to your customers. And it’s more than doing a survey and compiling answers. You have to talk to them, listen actively to what they’re saying, and also find insights between the lines. What do they need, what causes them pain, what do they wish for — inside your product and apart from it? Know your customer like you know yourself.”

-Kirk Simpson

“When prioritizing, one must put customer needs at the top. Consider: Is this good for the user? Will this (project) create a 10 times better user experience than we have today? Will completing this task make us better than our competitors?”

-Ariel Cohen

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Staying motivated through the ups and downs

No entrepreneur has the perfect path set out for them; there are going to be ups and downs, days you love your job, and days you want to give up. So, it’s important to get back on track when a rough patch hits.

How do you handle those days, weeks or even months that seem to be a little rougher than others? We asked these CEOS to provide one piece of advice they wish they knew before starting their journey:

“Find allies, mentors, peers to network with and share your challenges in confidence. You need those conversations to gather insights, and to use as a sounding board for your own thinking. During hard times (and in general), surround yourself with the best people you can, and give them the power to help you do what needs doing. Don’t put off hard decisions. They don’t get any easier tomorrow.”

-Kirk Simpson

“All CEOs have to sacrifice a lot and put in a lot of work. It takes an unwavering commitment and a passion that runs deep, but it will be rewarding.”

-Danny Loschiavo, co-Founder of BoldLeads

“Just stay focused on solving one problem better than anyone else while still making the impact you want to make. It won’t make you a celebrity, but you’re more likely to have the autonomy, mastery and purpose we all crave.”

-Matt Westgate

“Follow your passion and be persistent! If you are doing what you love, it won’t feel like work and when you get beaten up (it happens a lot), your passion is what will keep you going and not let you give up.”

-Vivek Mehra

“Have conviction to listen to all of the ‘no’s’ you hear, which will be a lot. Focus on understanding the reasoning of the ‘no’s’ versus feeling defeated.”

-Ariel Cohen


There is no doubt that as an entrepreneur, you will have good days and bad days, along with many rewarding moments. Hopefully, the fact that these entrepreneurs and CEOs are continuing to thrive gives you the motivation to hustle harder, even through the slumps. By preparing yourself for those bumps now, you will find yourself one step ahead of the competition.

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