Many firms were prompted to pivot and adapt to changing market conditions as a result of the pandemic. We spoke with a number of business owners in the United States to learn how some of the country’s most successful entrepreneurs altered their firms and added new product lines or services.
INTERVIEW HOST
The host of this interview was Jed Morley. Jed Morley is the CEO of a leading payment processing service provider called PlatPay.
Table of Contents
The question we asked:
What is the greatest, unexpected challenge you faced with your business, that you’d like to warn new entrepreneurs about? Please share your advice on how to overcome it.?
Wiliam Scott Goldman
Having pioneered the field of Branding Law and working primarily with startups/entrepreneurs for the past thirty years, here are three very common but easily avoidable mistakes:
1. Using a brand name with the mistaken belief that filing as a corp. or LLC with the Secretary of State confers trademark protection.
2. Applying for a trademark and/or using a brand name without properly clearing it first with a thorough database search, including all possible variations, checking for similarities in sound, appearance and meaning.
3. Choosing a trademark that’s generic or descriptive rather than coined, arbitrary or even suggestive as generic marks are unregistrable and descriptive marks are considered ‘weak’ and difficult to enforce. BONUS: Mistakenly believing that hiring an independent contractor confers copyright ownership as a work made for hire.
Instead, the contractor automatically owns copyright unless otherwise assigned by written agreement.
Chris Kille
The greatest unexpected challenges I have faced in my businesses over the years have always been people-related. Daily challenges will occur in day-to-day operations, and usually, those can be anticipated and corrected without much damage.
Employees and talent, however, are a completely different story. Employees can be like the ocean: ever-changing, unpredictable, and even hostile at times. On the other hand, they can also be gentle, warm, and calming. Both perspectives can change without notice.
The past 2 years have been extremely challenging because of what has been going on in the world. People have been laid off and started their own hustle. Some have decided they do not want to go back to work altogether. Some have risen to the top and made the best out of a bad situation.
Now that things appear to be calming down, there are another set of challenges. Who’s coming back? Do we need as big of an office as before? Can people continue to work from home indefinitely? These challenges can be frustrating, but are also some of the most rewarding because building and maintaining a business is one of the most satisfying experiences an entrepreneur can have.
Chris Kille is the Founder and CEO of Payment Pilot- a financial technology company, and Elevate Outsourcing- a global outsourcing agency. He has been an entrepreneur since 2005 and has built and sold multiple businesses for a profit. He currently resides in Charlotte, NC with his wife, Kristen, and their 3 dogs.
Leandro Sandmann
The most unexpected challenge we faced was scaling quickly enough to meet the demand. Since ExitLag was originally created for ourselves and a few friends, we were not prepared for a lot of users to be using the software but word quickly spread and more and more people were interested in signing up for the software.
From payment approval to granting access to the software, everything was done manually. One day, there were suddenly hundreds of clients waiting for their payments to be processed and their accesses to be granted.
I had to spend the entire day grating access to the new clients and processing their payments manually. I learned that business can grow a lot quicker than you anticipate and you need to be ready for that growth.
Christina Russo
Too Much Content – The Right People For The Right Job When my friend Cassie and I started our business, we thought it would be a humble little site that maybe twenty or so thousand people visited a month and we never expected it to grow into the behemoth that it has.
Instead of twenty thousand visitors, our business now attracts more than three million, and as the site grew faster and faster, we had to research and create more and more content, and before we knew it, we were overwhelmed and had to face the truth.
If we were going to stay in business and satiate the appetite of our community, we needed to hire researchers and writers and we need to do it fast. So we reached out to the people who mattered most to us, our community of faces and readers, and within a month we’d recruited a team that knew exactly what kind of content we needed, as they were part of the community that we were trying to appease.
I never imagined that runaway success would ever be an unexpected problem that I’d have to deal with, but it was and I’m eternally grateful that the universe saw fit to throw that problem at us.
Paul Sherman
I never thought that hiring the right team members would be so incredibly difficult. This is especially difficult when you’re small because small businesses often need employees that can wear many different hats as they grow and figure things out.
I would warn entrepreneurs to be very careful about hiring people that are qualified but a poor cultural fit. This is hugely important when you’re a small business because if you have one bad apple in a company of 500, it’s not so bad; if you have one bad apple in a company of three, it’s a real problem.
We overcame this issue by focusing on word-of-mouth hiring and less on traditional hiring boards. At the time, and still very much today, I felt more comfortable getting a referral from someone I trust because that person knows me and what I’m looking for in an employee. This made it easier to hire people that were cultural fits for the company.
Annie Singer
The biggest surprise to me in launching my own business was the sheer patience it takes to be successful. After launching, it is incredibly common to enter a phase that my business mentor refers to as the “trough of sorrows”. During this phase, your business is growing… one user at a time.
It makes you question everything you know to be true about your business and your product. It might take weeks to get out of this trough — or it might take many months! The best way to persist through this challenging phase of business is to have a strong network of support, including your family, friends, and business mentors.
Anthony Martin
Insurance companies pool money to pay claims. They have a ballpark of the premiums they will receive and the payout they will have to make. The pandemic resulted in a increase in the number of payouts in the form of business interruption claims, travel, cyber liability and trade credit.
This means that payouts have seen a massive spike in a very short period of time. Even though certain insurance companies factor in unexpected events, pandemics are difficult to gauge as they occur rarely and lack historical data. Since we are directly in touch with insurance companies in our line of business, this has affected us as well.
Yuvi Alpert
Our industry typically relies on an in-person experience, as consumers often wish to have a tangible feel for the types of products we offer, so recreating that in a virtual environment was our biggest challenge.
Whenever a business, especially those in the fashion and accessories industry, utilize an ecommerce platform, finding the best ways to instill confidence in the consumer can be a difficult hurdle.
I never anticipated the amount of platforms and programs, content, and service outlets we would need to utilize in order to find that perfect combination. Definitely, recreating the consumer experience in virtual space was the biggest challenge I faced in my business.
Adelle Archer
When we started our business, we knew that our product was unique and rare, and although it touched upon several different market spaces, the greatest challenge was identifying the best ways to communicate that to the public.
The vast majority of startups are entering a well defined market space, where expectations are already set on what is required of a product and service. Ours was a completely new and different concept, and deciding how to promote what we did, both to stakeholders and the public, was more difficult than I had anticipated and presented great challenges. After much work, and some trial and error, we were able to overcome these difficulties and carve out our space.
Joel Jackson
It’s a challenge to find the kinds of people willing to listen. In the entrepreneurial space, you have a lot of talkers, a lot of aggressive salespeople – but not a lot of listeners. I started early at Honest, and no one noticed what we were doing, but we didn’t let that deter us. In the end, the entire diaper industry changed its practices because of what we did.
You can’t let discouragement creep into your head. You have to be willing to put yourself out there. The key is to get your ideas in front of as many people as you can find. If you’re persistent enough and strategic enough, you will find those people who are receptive to your ideas. You never know which conversation will lead to success, so keep finding ways to put your product in front of people.
Gene Caballero
The thing I didn’t expect when starting my business was how lonely the journey would be. Immediate family and a few friends will always be supportive….sharing on social media, writing reviews, actually using your product, bringing food to the office at midnight, etc. Second-tier friends, like your bar buddies and old co-workers, just don’t understand the work it takes to build something from scratch.
They can’t fathom why you are not able to grab a happy hour or grab dinner on a Tuesday because you have to work. Slowly but surely, these friends will eventually quit asking and become mere acquaintances. There are 3 8-hour workdays in 24 hours…pick which two you want to work and you will be successful.
Nakia Whittaker-Woody
I am an entrepreneur, small business for 4 years now, my greatest and most unexpected challenge was Imposter Syndrome. I have been an Administrative Professional for 24 years and I am a ROCK STAR! But when translating those years and skillset to being a business owner, I cowered like it was day 1 of my career.
I would hyperventilate on camera, studied everything I could get my hands on, and still felt incompetent. I had never had any business experience or knew how to be an entrepreneur, so I learned to align myself with like-minded individuals who encouraged and supported me. I invested in some courses, because coming from Corporate, education equaled authority, thus helping my confidence.
I also invested in Mindset Coaching. It was an investment in myself, I was lucky to be associated with a great coach who was growing and testing her program using a Pay What You Can process. It was so instrumental in me learning to celebrate small things in my business, understand the reason for my pricing, and gave me the courage to increase my pricing to my expertise level.
David Jacobs
The greatest, unexpected challenge most successful business owners will face in the lifecycle of their company is successfully exiting from the business. With the success rate of finding a buyer and negotiating a transaction which closes close to 20%, most business owners will be unable to successfully from their companies after years and years of hard work and effort.
It is typically for successful business owners to receive unsolicited offers from time to time. While it is possible for a cold inquiry to result in a sale and a lucrative exit, most end up as wasted weeks or months spent supplying highly confidential materials for a due diligence process to a buyer who ultimately walks away. This happens because buyers reach out to hundreds of potential business owners per year but only make 1-2 acquisitions. After a few of these failed deals, many buyers conclude their business can’t be sold.
The most reliable path to a successful business exit is to find an advisor who understands your industry and can create a competitive auction between the potential buyers. The competition not only pushes up the transaction value, it also keeps deal structures and terms reasonable. A good intermediary will be able to properly package up your business for sale and then attract a large number of potential buyers quickly in order to create the needed competition.
Shaunak Amin
SnackMagic launched in 2019 and scaled rapidly. Our team now consists of in-house, hybrid, and remote employees across the globe. While flexible schedules offer a better work/life balance, we quickly discovered that good team collaboration doesn’t come down to workers being available at all hours.
Round-the-clock communications can put a significant amount of pressure on your team and lead to lower productivity and higher staff turnover. Fostering a good work/life balance for hybrid and remote employees across time zones comes down to managers and team members being mindful of everyone’s designated hours.
As projects require a significant amount of interaction, workers must be conscientious of when and how they contact their teammates to avoid a constant sense of urgency. We find that being considerate of time zones keeps the stress levels of our employees lower and reduces the chances of human error.
Becky Brown
One of the greatest business challenges that I had to face was learning how to set up, organize, and manage a remote workforce. As an executive, working remotely comes down to so much more than “work-from-home using a computer.”
First, it was the technology — I had to research, develop, optimize, and manage all of the technology necessary to run an efficient remote business. After all of that, I had to learn how remote management and leadership so that my whole team was up and running efficiently. If you are considering working remotely, you should be ready and prepared to do your research and optimization to make it all work. I hope that helps!
Zach Letter
Taking a passion and converting it to a business requires viewing that market differently, and making the transition from enthusiastic participant to a business creator represented my greatest challenge. It is very simple to critique a business from afar, passing judgement while not fully understanding the complexities they face.
]When taking my passion into a business model, I began to realize some of my unrealistic expectations, forcing me to make adjustments and thinking about modifications I never considered. Being able to merge my vision with the reality of business, and picking and choosing where I could realistically meet my goals was my biggest challenge.
Omer Reiner
The greatest challenge we experienced with our business was cash flow. We underestimated the importance of keeping healthy cash reserves in the bank to cover months where cash was not flowing in steadily, but the expenses, on the other hand, did not stop flowing out.
So we learned the hard way, and now we try to keep at least 3-4 months of operating expenses in a separate savings account just in case we have slow revenue months.
Jaclyn Strauss
Be aware that you don’t know what you don’t know. As entrepreneurs, we plan to launch our new company and feel quite confident that we have dotted every “I” and crossed every “T.” However, the truth is that you will have no way of knowing what the market desires until you launch your product or service.
Every entrepreneur should have completed numerous potential customer interviews, received feedback from a BETA version, or had a fresh set of eyes and ears on the concept and/or the product pre-launch. Before launch, these are all must-do items; however, the real valuable stuff comes in after the service or product is on the market. Be ready and willing to change paths, incorporate new ideas, change your target market, adjust your product/service for better market fit.
Do NOT resist what the market is telling you, or you will fail. We must be willing to listen, take the feedback as a gift and continue moving forward. Thinking that I had all of the answers and not quickly releasing this belief would not have been a recipe for my company’s success since the launch of my company. I am solving a real problem, but the way I am solving it looks different and feels different from what I initially thought it would be.
Overcoming the hurdle by being flexible and receptive to embracing the feedback has been the most valuable shift I have made on my entrepreneurial journey.
Nikhil Arun
Developing testing and vaccination products for governments, corporations, and communities in need during a pandemic was the hardest challenge we’ve faced. We were able to accomplish this by spending a lot of time understanding our customers and the intricacies of the issues in the pandemic to understand exactly what would help our customers.
When you do that, you recognize patterns and build solutions that address many problems at one. Doing this, we were able to deliver the first at-home saliva test, a way for organizations to launch their own tests, and a simple way for organizations to track and report vaccinations.
