Entrepreneurs Reveal Biggest Business Challenges Of 2019

Entrepreneurs share the challenges they face this year along with practical insight on how they plan to (or have already) taken steps toward solutions.

Growing startups and small businesses face a variety of challenges. As a business grows, persistent problems demand agile solutions. Thankfully, most small business challenges can be resolved.

We asked entrepreneurs to share the challenges they face this year along with practical insight on how they plan to (or have already) taken steps toward solutions. Here’s an inside look at practical advice and inspiration to help you tackle your biggest business problems with creativity, passion and a plan. Perhaps you can relate.


1. Humanize our brand with social media

“In this day and age, social media is the best way to connect with customers and expand a business. Yet, … it can be a challenge to grow your following and get people to stop and take notice. In 2019, we are looking to tackle this issue head-on and expand our social media presence.

“Part of this means creating a strong social media team with employees who are creative and passionate; and have a sense of what customers are looking for. It also includes humanizing the brand by selecting brand ambassadors, real people who can relate to the public and demonstrate exactly how and why they use our products.” 

Nate Masterson, CEO of Maple Holistics


2. Onboarding new employees

“As a software startup that’s focused on high growth, bringing new employees up to speed quickly is a very challenging problem. Our company is roughly 30 people and putting other things aside to focus on training is a very challenging thing to do. Our goal as a company is to reduce [training] time from 6 months to 3 months, and by creating repeatable processes around this will help us achieve our milestone.”

Tarek Alaruri, Co-Founder and COO of Fairmarkit


3. Finding qualified trade labor

“It is not news that we are experiencing an extremely acute labor shortage in the trades while at the same time seeing more consumer demand than I’ve ever seen in my 26 years since founding this business. We’ve been recruiting fairly consistently since January of 2015 and only hired three keepers in that time period. 

“In recent years, I’ve responded by working more in the day-to-day of the company to try to keep up while neglecting bigger picture activities and strategizing. I’m committing in 2019 to rekindle my industry involvement, thought leader status, and networking in order to position ourselves for better recruiting. With increased involvement at the industry level, I hope to gain more insight before strategizing on future recruiting efforts.”

Gregory A. Antonioli, GCP, President of Out of the Woods Construction


4. Maintaining share in a saturated market

“When we first got into our niche in 7 years ago, we were on the leading edge. Today, many companies have adopted the technology we focus on, which has been a double-edged sword. As a comparison shopping site, we want there to be more options to compare and contrast, giving our customers and prospects all the more reason to pay attention to our expertise. At the same time, several other industry experts have emerged capitalizing on the  comparison shopping element of our niche.

“It may be tough to continue leading the field, but we plan to: Double down on our reputation as industry leaders, i.e. develop case  studies across all of our market segments (consumers, businesses, government, etc.); Continue spreading awareness, (e.g. creative brand promotion tactics); Continue creating value, positioning ourselves as an industry leader. We’ll use non-gated (i.e. not for lead capture) reports on emerging technologies and companies.” 

Reuben Yonatan, Founder and CEO of GetVOIP


Photo: © Jacob Lund, YFS Magazine


5. Access to qualified local talent

“Since we are headquartered in Detroit (as opposed to Silicon Valley), there aren’t many qualified app developers in our hiring pool. After many local interviews, we still haven’t been able to find the level of quality talent that we need to significantly grow our business. 

“This year, we’ve decided to hire a remote team to address this issue. Already, we are receiving strong applications from individuals in other areas around the country where a background in software development is much more common. By opening up the talent pool to attract employees in other areas, we are confident that we will be able to significantly increase our level of business within the next 12 months.”

Michael Sims, founder and CEO of ThinkLions


6. Compliance with changing laws and regulations

“Every year the government seems to release a new regulation that can spell the end of a small business if you’re not staying up to date. Lately, it’s been the issues with advertising and information security. In the case of advertising, it’s getting harder to create compelling copy with the constant updates on what you can’t say and how you can’t target your audience. While we’ve been successful in working around those changes, it can still make it difficult to grow your business fast and still stay compliant with all the regulations that are being put out.” 

Tim Absalikov, co-founder and CEO of Lasting Trend


7. Creating scalable processes

“We are invested in building scalable processes and technology. But it can be challenging to find the time(and spend time within the business) when cash-flow and revenue requires us to focus on business development and our clients.

“We consistently remind ourselves that we need to build it for ‘an empire’ and not treat any task like we are a mom and pop shop. Tangible solutions have included: hiring junior accountants and leveraging their strong technical expertise and delegating; hiring a virtual assistant to help with administrative tasks; designating specific times in the week for blogging and marketing rather than letting it take over numerous hours each days; and lastly, ensuring we place our qualified team on new engagements and restrict the engagements that we, as co-founders, are actively involved in.

“After all there are only two of us and we didn’t build this business to become freelancers that rent time, rather we are trying to build something bigger. It is rewarding, difficult and will prove to be an eventful 2019 with this in mind.”

Jamie L. Smith, CPA ,CA, MPAcc, Co-founder of Amplify Advisors Inc.


8. Fundraising for an unsexy product

“First off, the Canadian (and particularly Toronto) startup scene has gotten so hot that it’s hard to compete. There are a lot of startups that are much better investments for seed funds or angel investors, either because they’ve already had an exit or they’re already over a half a million in sales. Secondly, and like many others, I don’t necessarily fit the profile of who investors typically look at: I’m a middle-aged mom. My startup is a marketplace, which means it’s not as sexy as an AI or chatbot startup. 

“Realistically, I will continue to try to network my way through the system and find funding. I’m trying out other options like a profit sharing platform. I’ll be applying, along with everyone else, to all the incubators, accelerators and startup schools that I qualify for. Lastly, I’ll be on the lookout for pitch competitions that deliver cash prizes. Truly, this is nothing unique, but when you’re running a startup, you only have the time to disrupt your own industry – not the investment/funding industry as well.”

Catherine Chan, Founder & CEO of FitIn


9. Growing without investors

“Our goal is to double our sales each month for the first quarter. Our game plan, which is already in effect is hiring a small and effective sales team. Given that we are on a tight budget in these beginning stages, their pay will be mostly commission-based. Making sure the team is passionate about fitness and our program will be key.

“We will also incorporate some marketing strategies that are low cost, such as utilizing social media with [useful] created content. Just by taking small bites out of larger content already created we can use this for Instagram, Facebook and Twitter. I am sure a lot of entrepreneurs share our challenge and we can all get over the hump with some creativity, passion and a plan.” 

Cary Williams, CEO of BOXING & BARBELLS, INC


What business challenges do you face this year? Let us know in the comments section below.


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