As we enter a new decade, fast-paced changes in the business world—and the technology advancements driving many of those changes—will only bring new business challenges and opportunities.


We asked entrepreneurs the top challenge they’re facing in 2020, and how they plan to confront it. Here’s how they responded:


Generating new customers

My biggest challenge this year is customer acquisition. Most markets are saturated with businesses or artists that offer similar products or services as mine. I have to find a way to get attention and stand out. I have hired a business coach who is teaching me the art of stepping outside my comfort zone. I am learning how to reach out to potential customers to show them the benefits of my products as opposed to the passive advertising I relied on in 2019.

Charles Olden, owner, Woldens Woodcraft, Stafford, Virginia


Improving social media advertising results

Right now, our biggest challenge is the variability in advertising results via Facebook and Instagram ads. To combat the variability, and to ensure our business is not wholly dependent on one channel, we are branching out to different channels this year. We are exploring Pinterest, an Instagram native shop, as well as going big on Amazon.

Kelly Reddington, founder, Big Wick Candle, Buffalo, New York


Scaling up prudently

The biggest business challenge we anticipate this year is learning how to appropriately scale our business as we grow. Being a project-based business, our revenue varies from month to month, and at times can be quite unpredictable. When our company reaches a peak in projects, we have to determine if it is viable to hire more people. However, when projects end and things slow down, we can be overstaffed and have to determine what actions need to be taken. The course of action we feel will provide us with the best outcome is to only hire another full-time person when every employee currently on staff is consistently working full days.  

Jake Hay, partner and head of development, PopShorts, Newport Beach, California


Increasing innovation—staying ahead of competition

The problems that I’m tackling in 2020 are all centered around innovation and being disruptive, so that I never find myself in a situation where we don’t have a stack of new ideas on tap. This year, we are scheduling more brainstorming sessions, and employees’ ideas will be rewarded with incentives. This should allow us to offer our customers exciting new features and keep at least two steps ahead of the competition.

Andrea Loubier, CEO, Mailbird, Palo Alto, California


Prioritizing initiatives more strategically

In 2020, our goal is to do fewer things, better. Last year, we tried to tackle a lot of different things, but the reality was that we didn’t have the resources to do them all well. We did many things “ok” instead of really nailing a few things. To support this, we now have monthly marketing meetings where we use our “Start/Stop/Continue” approach to be more disciplined about where our efforts are. Each month we evaluate our marketing and decide what we will start doing (new projects, tests or approaches), what we will stop doing (things that are not performing) and what we will continue to do. This provides discipline—especially by choosing to stop the things that aren’t working.

Krista Neher, CEO, Boot Camp Digital, Cincinnati


“Recession proofing” the business

As a scaffolding company, our business is closely tied to the performance of the economy, due to the majority of our work being construction related. As such, our main challenge this year is to “recession proof” our business model by lowering our overhead burden, eliminating debt and diversifying our client base to include industrial and commercial projects. With the economy being so reflexive and dynamic, we never know how close we are to the bottom falling out, so we want to make sure we are prepared not only to survive, but also to maintain growth during the next downturn.

Robert Lewis, president, Peak Access Solutions, Plant City, Florida

Overcoming the home-based business stigma

As a home-based business owner, people often don’t see my company as legitimate, despite that it’s over a decade old. They think I’m some small mom-and-pop or stay-at-home-mom-type business that can’t handle big jobs. Additionally, people are hesitant to come to my house for the first time to pick up an order. Getting over the “novice”or “hobby” label will mean sharing testimonials and examples of the work I’ve done via my website, social media and customer emails.

Glenna Nail, owner, Embellished Embroidery & Screen Printing, Jacksonville, Florida


Managing risk and growth in an unpredictable economy

Our challenge is determining whether to grow conservatively or aggressively. We’re making business decisions in a booming economy, but strategically we must decide what level of risk to assume. It’s easy to forget how much harder life is when the economy isn’t booming. Should we invest in a larger office space and equipment? Higher fixed costs are no big deal now—but what if there’s a recession? What will happen if a new president gets elected this year? We have some soul-searching to do. We’ll make a spreadsheet—or three—and do a sensitivity analysis. Ultimately, we have to weigh whether the cost of missing out is greater than the risk of getting wiped out in a bad economy.

Rob Misheloff, founder and CEO, Smarter Finance USA, Las Vegas


What’s the top business challenge your company faces in the year ahead? Share your insights in the comments section below!


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