Expert Roundup: Experts Reveal Their Biggest Business Start Up Challenges

Alayna Okerlund

Last Updated: February 24th, 2020

Business Owner with Head in HandsThis is part four of our small business owner expert roundup series.

Creating a successful business from the ground up definitely comes with challenges. It can be anything from not having enough funding to not getting the right customers. You have to put in hard work, countless hours, and make several sacrifices just to keep your business running.

For this final article in our expert roundup series, we asked the experts what their biggest challenges were when they first started their businesses.

Here's what they said.

Having several new responsibilities and limited time

“The biggest challenge when starting my own small business was learning to navigate the myriad of legal responsibilities that a small business must abide by. Thankfully there are many new companies out there geared towards small business solutions — ad hoc legal services, payment processing companies, and payroll providers, for example — that make it much easier to navigate these complex spaces.” — Jhonn Thomassen, Owner of Marine Park Coffee
“My biggest challenge was finding time to work and do everything exactly as I wanted to. That's one of the main obstacles for new business owners; you can't quit your full-time job (either in the workforce or as a stay at home parent!) but in order to succeed, you have to put 100% into your business. The only answer I have found to this challenge is creativity and coffee.” — Denise Stern, CEO of Let Mommy Sleep
“The biggest challenge I had was being overwhelmed. When I started, I had a mile-long to-do list. In time, I learned that the list doesn’t become smaller, but it does become more manageable when you do one thing at a time.” — Jen Teague, Owner of Jen Teague, LLC
“There's so much to do at once that you can't always devote the time to everything to make it perfect. Sometimes you just have to say 'good enough,' cross it off your list, and move on to the next thing. That was really hard for me. It might be your baby, but you can't afford to get so bogged down designing the website that you don't get anything else done.” — Lindsey Myers, Founder of Concrete Blonde Consulting

Not knowing the everything

“The biggest challenge I have had is navigating the unknown, especially when it comes to things like income tax. For the most part, I just keep track of my expenditures and work hard to be very organized.” — Ashlyn Biedebach, By The Brook Birth Doula
“Conversion rates on our website. They were abysmal. The e-commerce average is somewhere around 2.3%. Ours was 0.25%. We really had no clue what the metric was at first and we struggled literally for a year to get our heads around why nobody was buying anything.” — Mark Aselstine, Founder of Uncorked Ventures
“The biggest challenge was developing structure — putting the puzzle together, deciding how different tasks played to different people's strengths.” — Emily Wood, CEO and Creative Director of Raise Vegan Inc.
“Having to figure out how to get things accomplished with little money and limited resources.” — V. Michael Santoro, Co-Founder of Vaetas, LLC

Trying to build and maintain a customer base

“Getting business! It is hard to network with credibility and prove you know what you are doing before you have actually done it. It really goes back to the who you know. Service type businesses are lucky because you know when you need a plumber, but in something like ours where we are creating video content and helping businesses understand how to develop a video program, it is tough. A lot of businesses don’t even know they need a video program, so it becomes a build and teach business. We create the business and then have to teach consumers how to use it. The challenge is to do all of that in a seamless, cohesive way to get their business.” — Kayla Flam, COO of Social Snacks
“Making a website, learning SEO to get noticed, waiting for clients to call, and then dealing with the different personalities and expectations of clients.” — Jess Perna, Owner of
“The biggest challenge we had when we started our own business was finding how to cope with the number of new customers all at once. Sometimes when we are starting a new company we focus so hard on how to get to success, we don’t know how to handle the success when it comes. Planning ahead for almost any situation will get you in the perfect business mindset.” — Michael Russell, Ratchet Straps USA

Dealing with money and payments

“Keeping an even flow of revenue. Again, you have to stay on top of the sales pipeline and keep cash moving in quickly and profitably to ensure you have the money to maintain and grow your business.” — Gary Romano, President and CEO of Civitas Strategies, LLC
“Getting paid on time! My biggest clients also took the longest to pay — much longer than the terms that we initially agreed upon. So while initially had an urge to go ballistic on them, I had to pull back because they owed me (and continue to owe me) a significant amount of money each month.” — Rafe Gomez, Co-Owner of VC Inc. Marketing

Having to make the tough decisions

“Making tough decisions. Starting a business requires you to make impossibly tough decisions — decisions that you just can't tell are right or wrong to make. It's not like a math problem that can be solved or reasoned out. Instead, these business decisions require you to go with your gut and trust your instincts, which was something that I, as a more analytical and cautious type of person, had to get used to.” — Peter Yang, Co-Founder and CEO of Resume Writing Services


Top of Page chevron_right

Read Reviews for Top Merchant Account Services Companies

Compare Top Companies

Was this content helpful?
thumb_up Yes thumb_down No

The Top Merchant Account Services Companies

Cayan Logo
#1 Cayan chevron_right
6.9 Overall Score
star star star star star_half
Dharma Logo
#3 Dharma chevron_right
6.5 Overall Score
star star star star star_half

Related Articles

Get Our Newsletter – Be in the Know

Sign up below to receive a monthly newsletter containing relevant news, resources and expert tips on Merchant Account Services and other products and services.

We promise not to spam you. Unsubscribe at any time. Privacy Policy