America is one of the countries that is home to the biggest businesses in the world. However, starting these businesses has not been without challenges. American businesspeople face challenges like their counterparts in other parts of the world. We sat with some of them to discuss the most significant barrier in their businesses’ initial years and what made overcoming it difficult.
The question we asked them was: What has been the biggest challenge you faced in the first years of building your business and what made overcoming it so difficult?
Here’s what they had to say
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Sara Jane Blumenschine
Title: Founder
Company: Rise Marketing, LLC
Linkedin: https://www.linkedin.com/in/sara-jane-blumenschine-b5685597/
I’ve been working as an online marketing consultant for nearly 4 years now.
I quit my job as a Director of Marketing 2 years ago, and went all-in on my business—but it’s not been without its challenges. Namely, having confidence in myself.
Entrepreneurship is the ultimate leap of faith in oneself. There’s no one there to catch you, but you. So you have to believe that your success is inevitable.
If you don’t, you’re essentially guaranteeing your own failure.
That belief sets the tone for how you show up in your business, each and every day. I’ve definitely noticed a correlation between my confidence levels, and how my business is performing.
My clients have mirrored this back to me as well. I often catch them falling into similar patterns where they can begin to doubt their value.
When you doubt your own value, your boundaries go out the window. You start feeling the need to overdeliver, leading to the classic case of entrepreneurial burnout.
Or it can present as avoidant behaviour, where I see clients start under-delivering because they feel like, why bother, I’ll fail anyway.
Either way, their mindset sabotages their own success. That’s why it’s crucial to work on mindset daily as a business owner.
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Thomas Niemczewski
Title: CEO and Founder
Company: Dream Chasers
Linkedin: https://www.linkedin.com/in/thomas-n-26883b87/
The first few years of building our business were filled with challenges and learning opportunities. We had to learn how to scale our business, how to manage multiple projects at once, and how to make sure that we are not just making a statement but also delivering on it. In the first few years of building our business we faced challenges in many different areas – from finding the right team members to managing time and budgeting and to make sure that they were aligned with our vision and culture. This was a time-consuming process, but it is worth it. The right team members will make your business successful and will help you build a strong foundation for future growth.
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Aaron Rice
Title: Expert Dog Trainer and Co-owner
Company: Stayyy
Linkedin:
There are many challenges that come with building a business, but the biggest one is staying focused on our goals. As we grow our business, it can be easy to get distracted by other opportunities and lose focus on what we initially set out to do. I am constantly thinking about how I can grow the number of clients who enjoy and trust our service and how to improve their experience. It’s easy to get distracted by other opportunities and lose focus on what you initially set out to do.
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Raghu Ravinutala
Title: CEO & Co-founder
Company: Yellow.ai
Linkedin: https://www.linkedin.com/in/raghuravinutala/
When you choose to be on the less traveled path of entrepreneurship, facing hardships becomes akin to a rite of passage. And yes, we did have our fair share of challenges since we started.
Starting in the Conversational AI industry, the first major question to address was – how do you build a platform that enables businesses to engage with customers from across the globe? Conversation comes with so many localized nuances, so the problem is global. To build a global company, we knew we’d have to support many languages. This posed another problem: every company comes with different customers and different approaches to serving them. In conversation, including text and voice, that means different brand-specific diction plus all the different ways conversational AI needs to be modified in pitch and tone to suit the customer’s mood. So, we’d have to build a platform that was highly configurable.
In 2016, Yellow.ai began with a B2C product offering and while we were able to quickly get 50,000 monthly active users with over 20,000 transactions on the platform, the major challenge was creating a complete customer experience package. Getting the technology right (creating a great experience using Conversational AI and automation is a complex problem), customer and business acquisitions… these were all tough tasks. But giving up never crossed our minds–simply because doubting our team’s ability and our vision was not an option. What drove us ahead was our conviction. We knew that the market was a nascent but very large one, we were one of the first movers, and we had customers who came back satisfied and optimistic about the impact of our solutions. That’s when we decided to pivot to B2B. Since then there has been no looking back.
Also, while investor sentiment for this market was high in 2016, it saw a plunge in 2017-2018 since there were so many similar companies in the market that it was hard for them to differentiate. The market was pretty brittle at that time. However, we wanted to take time to raise the investment. We were absolutely focused on building metrics and proof points, and thankfully, we did not have short term cash problems. In fact, in 2017, we made a 200-250k profit. Considering Conversational AI was a relatively nascent industry, and in such a short amount of time, we had managed to become a part of it! What kept us going was our belief in our product, our technique and most of all our team.
Building Yellow.ai into the company it is today was truly the most transformative thing I have ever done in my career. I’m grateful to be part of the team that helps other companies and professionals transform their own organizations and careers through conversational AI.
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Jensen Lee
Title: Founder and Managing Member
Company: bidetsPLUS, LLC
Linkedin:
When my business first started, I faced many challenges. The biggest challenge I faced was figuring out how to get my business off the ground and find customers. The most significant one was how to get people to know about my business and trust me. I was not sure of what the biggest challenge would be. But as I started to grow, the challenges became bigger and bigger. The first years of building my business were mostly about learning and building a company from scratch. While it is not easy, it is possible with some effort.
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Zach Goldstein
Title: CEO
Company: Public Rec
Linkedin: https://www.linkedin.com/in/zach-goldstein-b7002714/
One thing I did for my business that I almost regret is working as our customer service department alone until we hit seven-figure sales. I stubbornly obsessed over complaints, issues with our product, and other customer feedback by checking my email from waking to sleeping, resolving issues, and speaking to customers directly to encourage the best shopping experiences.
I lost sleep obsessing over micromanaging our brand reputation and meeting customers’ needs from our product. I didn’t want to hand over the reins to anyone else until I was totally sure we were selling a useful and infallible product that could fulfill our brand promise to all of our customers.
Eventually, when I could no longer physically do it alone, we hired a CS team to navigate and triage customer issues. A difficult part of growth, and growing a business specifically, is letting go of some control and giving your investment the room to grow on its own while you do what you can to facilitate it.
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Maria Shriver
Title: Co-founder and CEO
Company: MOSH
Linkedin: https://www.linkedin.com/in/mariashriver/
While I have two decades of experience raising awareness for Alzheimer’s, which disproportionately affects women, many companies I pitched my vision to didn’t seem convinced that an idea brought to them by a woman in her 60s would be viable in today’s marketplace. Additionally, no one I spoke with understood the importance of eating for brain and body health, so they felt consumers wouldn’t be interested either.
My son Patrick said I should accept rejection as an opportunity to bring forth my idea on my own. And as he and I saw a family member slowly lose his mind to Alzheimer’s, we want to do our part to prevent anyone from having to experience this. So we launched a mission-focused company to get everyone thinking more about brain health.
While Patrick brings a wealth of better-for-you CPG industry knowledge, he’s also able to engage people his age and those who are interested in this space. Ironically, many Millennials and Gen Zers are standing up for better brain health. With people living longer these days, these younger generations have also experienced a parent or grandparent with the disease or have struggled with mental health challenges themselves, so they have joined our mission-driven community of brain health warriors.
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Jeff Moriarty
Title: Co-Owner
Company: Moriarty’s Gem Art
Linkedin: https://www.linkedin.com/in/jeffmichaelmoriarty/
Because we sell luxury jewelry, the biggest hurdle was getting people to trust spending $1,000+ online with a company they have never heard of before. In order to combat this, we spoke with the customers that actually made a purchase with us to tell them why they did and what might have caused some hesitation. Based on their answers, we implemented 3rd party customer reviews, more information about our employees, and online videos to increase the trust in our company. It took a very long time to do this, but now customers choose us based on these strategies, and nothing else. We had our most successful year ever in 2021 and it continues now.
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Christine Bright
Title: Founder
Company: Parenting Game LLC
Linkedin: https://www.linkedin.com/in/christine-m-bright/
The biggest challenge for me was getting my marketing message clear and concise. Initially, I wanted to cast a wide net because I needed every customer, so I thought. However, customers were confused and didn’t understand how I could help them. As a result, closing became difficult because I continually pivoted my marketing message to appeal to everyone. I knew I needed help. Seeing the cost of getting help was a bit overwhelming. However, I did come to realize it was an investment. Getting my messaging right would pay dividends in the long run. Paying to get help was a bit of a hit to my ego. Putting my ego aside and listening to other opinions and thoughts was challenging. But in the end, it has paid dividends as well. Also, as the sole owner, I found great value in having a person to brainstorm with me. All the time and money invested has resulted in clear messaging and finding my niche market. My average closing is now 50%.
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Lizann Lightfoot
Title: Founder of the Seasoned Spouse blog
Company: Seasoned Spouse
Linkedin: https://www.linkedin.com/in/lizann-lightfoot/
When I started my writing LLC in 2016, I faced numerous challenges. In the first month, the biggest frustration was figuring out how to create a website (which would become my Seasoned Spouse blog) and all the technical challenges of connecting plugins and using social media sites for business. I spent many tearful hours watching YouTube videos trying to learn how to establish the technical aspects of a business on my own, since I had no funds for website design or development.
Once I passed that hurdle, the biggest challenge in the first year of my business was finding consistent clients. As a freelance writer, I initially accepted any jobs that were offered in my area of expertise, regardless of pay. For the first year, my writing schedule was inconsistent. Some months, I would do two articles for a particular magazine, but then I might not get another assignment from them for several months. Other companies wanted me to publish several articles in the same week. So it took a lot of pitching and trial and error before I settled into a somewhat predictable schedule and had a steady stream of income from multiple clients.
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David Pressler
Title: Owner / President
Company: D R D Enterprises Inc of Davie
Linkedin: https://www.linkedin.com/in/therealdavidpressler/
Corporation constitutional and Bill of Rights violated by the State of Florida within 60 days of developing a solar powered fish farm.
ONLY the Florida Department of Agriculture and Division of Aquaculture have authority over farms and farm structures in Florida. When DRD Enterprises inc of Davie, a single owned disabled veteran small business, bought a certified fish farm at Arcadia, Florida it expected to be protected by the laws of Florida, they were not!
Within 45 days of buying this certified aquafarm and while recertifying DeSoto County, Florida issues a cease development order on a certified farm and evicts the aquafarm caretaker required by Florida law under the Aquaculture Policy Act. DRD Enterprises inc of Davie had a business plan to have a solar powered fish farm up and running prior to the arrival of President Obama at Arcadia in 2010, this illegal action ruined that plan.
Immediately the Florida Department of Agriculture was notified of these acts. Reply from Mr. Costigan counsel for the Department was that there were no enforcement laws to protect farms like mine? By way of a Special Master order DRD Enterprises inc of Davie was prevented from constructing tornado proof Miami Dade County storage sheds on a certified aquafarm! DeSoto County claim that sheds in process of being built for resale only, this before any were completed and no sales?
In 2011, by Freedom of Information Act, DRD Enterprises inc of Davie found that emails claiming the guilt of DRD Enterprises inc of Davie. Demand for evidence to those claims could not be answered. Further attempts to reveal the violations and the hidden truths committed by the Department of Agriculture and Division of Aquaculture were stone walled. Law firm letter sent to Stephen Hall counsel for the Department of Agriculture demanding evidence of guilt. Mr. Hall reply indicating that tornado proof storage sheds were not farm buildings?
Attempts to hire a law firm to fight State of Florida and six officials including Governor Scott without severe financial loss was not an option. As a representative of the corporation I began filing civil rights and Bill of Rights violations against six officials of Florida.
At some point during the filings State Attorney Bondi request dismissal on grounds that corporations cannot file a civil rights complaint and MUST hire a law firm. Hiring a law firm was the downfall of my complaint.
All my filings and causes only needed to be reviewed and refiled instead the law firm began dealing with the opposing lawyers for the State. Now I know you cannot file a suit against a State, I did not. My suit was against six officials. Once this law firm took over and $6000 later my suit became DRE Enterprises inc of Davie VS Florida Department of Agriculture et al a suit that now could be dismissed and was. $6,000 to ask for evidence of guilt and still none shown?
When two or more officials conspire to conceal the truth if violates the Conspiracy Act of 1964. Six Florida officials conspired to protect DeSoto County from prosecution. Will YOU let them get away with violating the Constitution of these United States and your Bill of Rights? Let your congress person know about my story.
DRD Enterprises inc of Davie eventually leased the aquafarm so as to make mortgage payments. Currently offering tornado proof homes and still the backyard tornado proof storage sheds.
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Judie Shepherd-Gore
Title: Executive Director
Company: InnerCity Collaborative CDC
Linkedin: Judie Martin
Financing the dream and gaining the support of the InnerCity youth that made this dream possible. The rampant gun violence that permeates our City and the country gives me a sense of urgency to show them their worth! That education is vital for them to see themselves out of darkness and into the mainstream of Society.
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Drewbie Wilson
Title: Vice President
Company: Break Free Academy
Linkedin: https://www.linkedin.com/in/drewbiewilson
The biggest challenge I faced in the first years of starting my business was learning to respect and control my time. It wasn’t until I learned how to manage time and build boundaries in my personal and professional life that I was able to get what I was worth in the marketplace. Learn to use the calendar as a tool and not a prison. Instead of reacting to everything that comes your way during the day, learn to prioritize your time on the projects that are required to reach your goals. When you’re able to focus all of your expertise on one project at a time, you find that you’ll get more accomplished and still have time to enjoy the benefits of your entrepreneurial spirit! Plan out those personal and professional priorities on the calendar, then check each one off the list as you go through the day.
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Tim Kerin
Title: Owner
Company: Facility Partner Services Inc / CORE Networking / Essence of Dreams Costa Rica
Linkedin: www.linkedin.com/in/tim-kerin-2ba66
Accountability. Taking ownership and responsibility for your actions. That is what accountability means. Now how many entrepreneurs look in the mirror and can’t blame anyone else but who is in the mirror. It is your business, your dream, your goal and you are all in. But everyone else has their own rules to play by, and no mirror to look at themselves. You risk everything to start a business and need honesty and reliable professionals around you. It is sad that today so many people are non-accountable and that this takes time away from the business to read through and pivot from this. It is rampant, your professional services of banking, accounting, lawyers that are supposed to be your trusted support staff. Your vendors, clients and even you own staff. You have to push through all this and keep moving forward no matter what.
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Yuvi Alpert
Title: CEO
Company: Noemie
Linkedin: https://www.linkedin.com/in/yuvi-alpert-3b865148/
Our market generally relies on an in-person experience, as customers want to have a tangible feel of the products we offer, so recreating that experience in a virtual space was our biggest challenge. Whenever a business in the fashion and accessories market uses an ecommerce platform, finding effective ways to instill confidence in the consumer can be a difficult obstacle.
I did not anticipate the amount of different platforms, app programs, content, and service apparatuses we would require in order to find the perfect combination to provide our customers that brick and mortar store feel. Without question, recreating the consumer experience in virtual space was the biggest challenge I faced in my business and one we needed to overcome to reach the success we now enjoy.
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Cody Candee
Title: CEO
Company: Bounce
Linkedin: https://www.linkedin.com/in/codycandee/
We are part of the travel industry, thus, our business does not only encompass the US, but international regions, and it was because of this, we faced our biggest challenge, which was designing promotional campaigns for foreign markets. Marketing tastes change when you leave the country and what works in the US market may not necessarily work in other countries, thus, failure to adjust led to ineffective campaigns.
Therefore, through much trial and error, we learned by sending small teams to investigate desired markets, and partnering with synergistic businesses in those regions, we were able to learn about the local culture, and adjust our campaign accordingly. Yet, marketing for many different tastes was, and continues to be, one of greatest challenges and requires a great deal of resources to conquer.
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Imran Ali
Title: CEO
Company: Nexum LLC
Linkedin: https://www.linkedin.com/company/nexumdate
One of the greatest challenges we’ve faced during the first years of building our business is ensuring that we had a solid grasp on how to perform for a marketing standpoint! As more technical minded founders, we found it difficult to understand and grasp the marketing side of business and how to manage on that front. In terms of solutions to this issue, we’ve been proactive in educating ourselves through books, media and primarily other smart people. The overcoming of this process via the solution is particularly difficult as it forces us to take time and effort away from the business and more primarily on how to operate the business. Striking the balance between the two continues to be the struggle we continue to solve as the business continues.
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Rishi Narayan
Title: Co-Founder, Chief Revenue Officer
Company: Underground Printing
Linkedin: https://www.linkedin.com/in/rishinarayan/
After finishing grad school, Ryan and I decided to stay with the business and make it our main focus. We had a big decision to make for the direction we wanted take our business in. We could go completely virtual or open physical stores. To keep the focus on customer service, we started developing the idea of opening a retail storefront in order to reach our customers in a more meaningful way. While our competitors were moving exclusively online, we opened our first store on South University in early 2008. Our first store location, which was less than 200 square feet generated over $1M after its first year. We quickly opened a second Ann Arbor location and that grew quickly too. Eventually we were able to take advantage of the downturn in the economy during the late 2000s to expand into vacant storefronts on several college campuses. We continued with this growth strategy and expanded throughout the Big Ten and began opening store locations with bigger footprints that not only provided custom printing but also began offering printed collegiate merchandise for a more traditional retail shopping experience.
Through this, I’ve definitely learned just how important it is to stay organized and on top of things. A lot of the tools I use are particularly good for that. Something that is helpful to learn is that things are not going to just get easier. You need to keep working and keep pushing yourself in your work and you need to push your company to be of the highest standard possible. All of us involved with UGP keep applying that every day to continue and put out the highest quality possible apparel while maintaining a strong focus on customer service.
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Ronald Williams
Title: Founder
Company: BestPeopleFinder
Linkedin: https://www.linkedin.com/in/ronald-williams-627239233/
Proving a real cost-benefit of our products/services was one of the biggest challenges in the first years of my business; i.e., to show the consumer the exact value. And by value, I mean not just how much that product or solution will cost, but its advantages over the competition. Three particular things related to this challenge bothered me a lot, and they were
· What are the service differentials?
· How does it solve the client’s problems?
· Does it really meet the client’s needs?
Though overcoming this challenge is pretty tough even for the seasoned professional, analytic and soft skills such as communication, organization, and presentation are the most important because with these skills you can effectively advocate your product or solution. My best advice, in this context, is to have patience, educate your audience, and let your audience decide unbiasedly. Don’t influence the opinion of your client, rather focus on showing the differential.
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Nick Jordan
Title: Founder and CEO
Company: Workello
Linkedin: https://www.linkedin.com/in/nickfromseattle/
Getting Investments
Obtaining financial backing for the company was easily the most difficult obstacle for me to overcome as a startup founder. Finding investors is a long, arduous process that involves numerous applications, pitch sessions, and rejections.
I did some research in order to have an understanding of the funding options that are most suitable for the company. I investigated the business angels or fundraising circles you are applying to and tailored my pitch to appeal to them.
For the sake of your mental health, while you are searching for funding, you should focus on maintaining a healthy lifestyle by attending to your diet, maintaining an exercise routine, and getting a sufficient amount of sleep. It will make it easier for your brain to maintain concentration. You will have a greater sense of confidence in your ability to handle the barrage of interviews, rejections, and interrogations that you will be experiencing.
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Benjamin Stenson
Title: Owner
Company: Norsemen Home Remodeling
Linkedin: https://www.linkedin.com/company/norsemen-company/
Financial planning
Poor financial planning is one of the most typical blunders committed by beginning companies. During the early months and years of my business, underestimating the initial expenditures and ongoing expenses, as well as wrongly pricing products and services, almost crippled my business.
The best advice I can give you comes from my own personal experience: do your homework to get a realistic picture of costs and include every possible expense in your budget from the outset. Subscriptions, registration fees, and delivery charges, in addition to the more substantial costs (offices, staff, inventory, etc.), can soon add up.
To ensure that you’ll be able to pay your expenditures and make a profit, you’ll need to know all of your costs first. And always have contingency plans in place for any unexpected issues that may arise in any part of the business.
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Pavel Stepanov
Title: Founder and CEO of Virtudesk
Company: Virtudesk
Linkedin: https://www.linkedin.com/in/pavelgstepanov/
“In the last 5 years of operation, we have come far. However, some of the major challenges we have faced are finding and retaining good talent and good leadership. It can be hard to find people who think similarly to you and want to see the company go in the same direction, understand the company’s mission, and have only the company’s interests in mind. It’s also been a challenge to find good leaders who can lead by example, be good trainers and mentors, and build up team morale and productivity.
Despite these hardships, we have steadily and proudly grown every year we have been in business. We have done a lot of hiring lately and have brought on a lot of great new team members that are extremely talented, hardworking, ambitious, and eager to learn. They have tremendously helped the company increase lead generation, client sign-ups, and getting us into new industries.
As a CEO and leader myself, I’ve learned through this process that it’s essential to hire people with a diversity of talents so that everyone on your team can complement one another.” – Pavel Stepanov, CEO of Virtudesk
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Kim Abrams
Title: CEO
Company: Abrams Roofing
Linkedin: https://www.facebook.com/abramsroofingky
Talent and people
Your startup’s success or failure will be greatly influenced by the people you bring on board. I recommend that you spend some time searching for the best prospects and being mindful about recruiting a team that will function well together.
As the founder of our company, I can attest to the need of working closely with new hires to learn about their individual strengths and weaknesses. Your team may assist develop ideas, discover potential weaknesses in plans, and serve as an effective sounding board if you establish open and frequent communication amongst yourself and the rest of your team.
If a member of your team decides to depart, be sure to find someone to take their place. When a retiring employee’s job is simply shared among the rest of the team, it can have a detrimental influence on morale and burden the remaining team members.
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Ray Leon
Title: CEO
Company: Pet Insurance Review
Linkedin: https://www.linkedin.com/in/rayleoniii/
Staying consistent over long periods of time has been the biggest challenge for me. I found out quickly that when starting a business, you need to exert more effort, over an extended period of time to stay competitive. Maintaining this sustained level of productivity has oftentimes led to stress and occasional burnout. Overcoming this can be difficult because the pressures of success and taking care of the many responsibilities as a business owner can have a firm grip on your mind.
Fortunately, I was able to overcome this challenge by keeping a rock-solid network around me. My network of colleagues, family, friends, employees, and business partners all helped keep me grounded and focused on my vision for success in their own ways. This alignment of support helped me sustain my productivity and long-term effort to build a profitable company.
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Lee Cristina Beaser
Title: Founder, The Career Counter
Company: The Career Counter
Linkedin: https://www.linkedin.com/in/leebeaser/
The biggest challenge I’ve faced as an entrepreneur / blogger has been figuring out my target audience. In other words, who specifically do I want to help and what is their biggest problem that I can help solve?
I learned from taking several courses on how to build a successful, profitable online business that you need to figure out who exactly you’re trying to help. If you’re talking to everyone, you’re talking to nobody.
At first, I thought I would focus on helping college students land jobs, because I worked for many years as a college career coach. However, I quickly realized that the population I wanted to help was moms re-entering the workforce after a career pause. I am also a mom who has had to leave and re-enter the workforce several times, so this topic was very personal to me.
Picking a population I could relate to and knew personally was instrumental in being able to build my brand and career products and interventions. Although I’ve been able to create many targeted products and write targeted blog articles for my niche audience, I still struggle with keeping my focus solely on moms. But I’ve also come to realize that’s ok. I can help moms, and I can also create resources that help other populations like students and mid-career changers.
The biggest thing I’ve learned is that it does help (at least initially) to focus on a more specific population when you’re starting out with building your business. If you’re trying to help everyone you can easily lose focus and get overwhelmed.
