There are many paths to becoming an entrepreneur. Some people stumble into it, while others have been working towards it their entire lives.
In this interview, we speak with the CEOs and entrepreneurs of different companies to hear their experiences. We asked them about the difficulties they faced on their journey to becoming an entrepreneur and how others can achieve the same success. Hopefully, the interview article will provide valuable advice and tips for anyone who is looking to start their own business.
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Aaron Rice
Title: Expert Dog Trainer/Business Owner
Company: https://stayyy.com/
The journey to becoming a business owner is not easy and requires a lot of work and dedication. It is not an easy feat to achieve even for those who have been in the industry for years. I faced many difficulties on my journey to becoming an entrepreneur.
The most difficult part was finding the right people to work with. I had to find people who share the same vision and have a passion for what they do. I had to overcome a lot of obstacles in order to make it and these obstacles actually made me stronger and more resilient as an individual. I faced many difficulties on my journey but I always believed that anything worth doing was worth doing well.
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Alli Hill
Title: Freelance Writer and Founder of FreelanceSpeak.com
Company: https://www.freelancespeak.com/
Two words: time poverty. When I first started building my writing business, I was working 9-to-5 for someone else while also raising two kids under 2 years old. I’d come home having worked all day, be a mom until bedtime, then hustle and grind until midnight or later.
Repeat the next day. It was exhausting and so hard to be present for my family while I was building my dream. But I was thinking long-term — I wanted this business to be fully sustainable with predictable income before I left my safety net. In less than a year, I had fully replaced my full-time income. Then I revenge-quit my job.
Now, six years later, I still find it hard to say no to new clients and turn down opportunities, but I have learned to be more selective about the projects I take. I’ve now grown my business to include a 3x salary, a 4-day workweek, and the freedom to live life on my own terms. All the result of unwavering tenacity. My advice — keep going if the reward excites you.”
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Calloway Cook
Title: President
Company: https://illuminatelabs.org/
Every successful brand scales in a different way. Some brands use paid ads to quickly scale revenue. Some brands take a primarily social media marketing approach. For our brand, it took over a year to find a marketing channel that worked.
We tried paid ads and failed. We tried influencer marketing and failed. We tried social media ads and failed. Content marketing was incredibly effective for us, because the content we publish is more in-depth and much higher-quality than our competitors. We scaled our site traffic from around 3,000 to over 130,000 in the past year by publishing great content on various health topics.
To other entrepreneurs, I’d recommend that you try every potential marketing channel and fail fast. Don’t invest too much money into any one channel until you see success. You want to give yourself the highest percentage chance of profitability on any one channel, and unless you have a million dollar marketing budget that requires a strategic and lean approach.
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Chris Mitchell
Title: Founder & CEO
Company: https://www.intelusagency.com/
Hands down, my biggest difficulty as a Founder of a marketing agency is growing my business without investors or seed capital. I bootstrapped the entire thing and it’s given me a ton of gray hairs.
For years, I played a balancing act between sales, marketing, and fulfillment and I never could scale past 10 clients at a time until I learned to build step by step processes that anyone can follow and hired people with specific roles in the process. I also learned that no matter what, it’s never ok to stop doing sales & marketing, even when we get an influx of customers. It’s important to keep bringing in new revenue to compensate for churn when customers cancel their subscription.
Another challenge I faced with hiring was with our limited capital, hiring part time freelancers we used many of them like swiss army knives having them do a little bit of everything. When I realized the importance of having everyone’s roles focused on specific areas, everything started to change. Now we have someone dedicated 100% to marketing and lead generation, someone focused on sales, and another person strictly dedicated to customer success, ensuring that customers stay happy with our service. Finally, I can focus on growing the business at a high level without getting bogged down in the daily minutiae.
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Ben Hyman
Title: Co-Founder and CEO
Company: revivalrugs.com
We started our business in 2017 and it was a difficult year. It was just the four of us in the beginning and we had raised money ourselves. It felt like our reputation was on the line, because people were trusting us with their savings.
We had originally planned to do a kickstarter, but three days before it was set to launch our application was rejected. It turned out to be a blessing in disguise, because it became less complicated. We quickly hired a fifth person to head up our operations in Turkey and then we just got started purchasing rugs, designing the brand voice and style, putting together our website, acting as customer service, etc. A lot of blood, sweat, and tears went into the first year, but it was worth it in the end. We’re now thriving.
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Chenadra Washington
Title: CEO, Founder
Company: www.blackorchidspr.com
– I had been in the corporate world since leaving college and had great success. I knew I wanted to be an entrepreneur but had no idea what kind of business to start. I had to take some time off to figure out what that was. I started volunteering in a business community and learned business basics, but most importantly I listened to some of the pain points of my peers. In that, I found a way that I could use my innate skills to serve and also make a profit.
– Another challenged I faced as an African-American business owner is the knowledge around startup capital and leveraging different funding sources to fuel my business. According to Fundera, 44% of Black business owners use their own cash to fund their businesses. I did not want to rob my household to fund my business, so I had to get the help I needed to learn about funding and the importance of having a solid plan to utilize funding.
– There have been many scary days. When starting something new, its important to not get paralyzed by fear. I have to always remind myself that consistency matters and to fight to the finish.
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Christianna Johnson
Title: Founder, chief copywriter, author
Company: Bychristianna.com
My toxic mindset was one of the biggest difficulties I had to overcome to become an entrepreneur. I didn’t think I was one of those people, the kind that had a vision and a purpose and stepped out on crazy faith to make it happen.
The critical voice in my head — which sounded a lot like my mom — could point out every way and reason things could go wrong for me, and why I couldn’t make a business out of writing. It said that I’m not the go-getter type, that I’m lazy. That was something other people did, but no one where I’m from does things like this. It’s very blue collar. I’m a great writer — that’s a fact, not a brag.
I’ve had a talent and passion for storytelling since I was eighteen, and I’ve made an intentional effort to build on my craft. But I couldn’t figure out why my stories weren’t out there or why I couldn’t seem to finish a book or find clients. I didn’t go to school for writing. I made a B in College English. I didn’t know copywriting was an actual job — definitely didn’t know I could do it from home. But I knew I had the gift, and no matter how far into corporate and analytics I went, I still needed a way to be creative. I reached a point in my corporate career where I saw the limit to what I could do there, and what retirement would look like after decades there by looking at my supervisor.
After buying into a course that helped me shift my mindset and give me the framework for entrepreneurship, I worked at changing my negative mindset to a growth mindset. There were still moments of doubt and backtracking, but I created my business in 2020. At the end of 2021, I quit the corporate job and entered full-time entrepreneurship. I no longer allow myself to doubt and wallow for too long, but trust and believe that I am successful and I’m moving toward that every day.
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Christina Russo
Title: Co-Founder & Creative Director of the Kitchen Community
Company: https://thekitchencommunity.org
The biggest difficulty, or hurdle that I had to overcome, was myself. I always wanted to venture out on my own and follow my heart and passion for business, but I was never quite confident enough to make the leap of faith that I needed to in order to make it happen. And the only way I managed to conquer my fear was when I absolutely had to.
After I lost my job, I thought “Well, I can go back to doing exactly what I was before, being unhappy, working punishing hours to make someone else rich or I can see this as an opportunity to actually attempt to make my dream come true”. So, that’s what I did. I called my friend Cassie, explained my idea and we both started talking to investors about the business we wanted to run. Two years later, and that business now has a monthly audience of more than three million people and I’m making a six-figure salary.
And all I had to do to make that happen was to face and defeat my own worst enemy, who as you’ve probably already guessed, was me.
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Jahna Eichel
Title: CEO
Company: https://thecreativeagencyco.com/
Becoming an entrepreneur presented many obstacles. Living and working in NYC started as a dream. Being a woman in Corporate America, I felt welcomed and accepted. Until I became pregnant.
Suddenly, I switched from a serious business woman to the one everyone ignored. Leaving NYC was the best decision I made. Moving to Colorado I felt the potential to be taken seriously again. But I still had to prove it. I had to prove that being a mother wasn’t the issue, it was the stigma around it. Through my own integrity and grit, I was able to not just move past my own mental barriers but push through others as well. Once my clients saw that I could take care of their company as well as I take care of my own children, the obstacles started to clear away. I now own and operate five businesses in the greater Northern Colorado area.
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Ivan Flores
Title: CEO and Founder
Company: www.thebuffalospot.com
“My difficulties in becoming an entrepreneur were all based on lack of knowledge and experience. I never lacked in enthusiasm, passion, or desire, because owning a restaurant had been a childhood dream for many years. When I opened my first restaurant, El Encinal” in 2013, I believed that with enough hard work and determination, the restaurant would be a huge success.
Nothing could be further from the truth! I encountered many obstacles simply because I did not know everything about the business side of running a restaurant. We had great food, authentic recipes, and good employees, and I thought that would be enough to succeed. Much too late, I realized I did not know anything about things such as licensing, business permits, state and country regulations, working with suppliers, and much more. I did not have the right attorneys, for instance, who specialized in restaurants, trademarks, and franchising. From attorneys to accountants, not having the right people to guide me was a disaster and the restaurant closed the same year we opened.” “Just about any entrepreneur experiences failure.
The mark of a real entrepreneurial spirit is someone who learns from their mistakes and moves on. Entrepreneurs cannot be afraid to take risks and forge ahead, even if everyone else is telling them to hold back or scrap their plans. Fortunately, when my first restaurant closed, I was determined not to let my childhood dream vanish. I vowed I would succeed again with another restaurant when the timing was right. I knew that I needed to learn more about the industry so that I could capitalize on my mistakes one day.
I talked to other successful restauranteurs, read business books, and networked until I found the right professionals to guide me on my next venture. After a few years, I knew I was ready to open another restaurant.” “In 2013, I opened my first Buffalo Spot restaurant in Long Beach, and it quickly became known for its World-Famous Buffalo Fries. Not buffalo chicken wings, but buffalo chicken served on loaded French fries. This simple concept of marrying chicken with potatoes caught on quickly, and before we knew it, we had franchises springing up on the West Coast and in the Southwest. In 2019, I opened the first Blue Burro Restaurant, serving our guests burritos for breakfast, lunch, and dinner, along with loaded fries and unforgettable milkshakes such as our Blue Horchata.
I went on to open Tacomasa, which specializes in authentic Tijuana recipes, and this restaurant was also a success. Today, I have more than 40 locations in four states with plans to open numerous other locations throughout 2022.” “With determination, resilience, and a commitment to learning as much as I could about the business, everything has fallen into place and it’s been relatively smooth sailing. I am not saying I have not had any difficulties, because that is the nature of any business, as any entrepreneur knows. For example, when I opened the first Buffalo Spot in 2019, I found myself low on cash reserves and was concerned about making payroll and other obligations.
I had a lease pending on a second location at the time, and everyone was advising me not to move forward with the second location because the timing was not right. However, as an entrepreneur, you have to trust your instincts. There is a time to listen to the advice of others, and a time to do what you know in your heart is right. I went ahead with the second location, and the rest is history. The first Buffalo Spot suddenly caught fire and we were swamped with guests who often returned with family and friends.
The success of the second location followed shortly afterwards, and we continued to grow. For anyone who has a dream, a concept, or a good product with hopes of becoming an entrepreneur, my advice is to learn as much as you can prior to launching your business. I wish I had known the right lawyers, accountants, and franchise advisors when I started my first business. Instead, I poured my heart and long hours of work into it, only to see it fail within several months. Always spend time researching your idea, the market, and getting recommendations for professionals who will have your back. Enthusiasm and hard work are very important, but these two things can only carry you so far in the competitive business world.”
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Karen Lee
Title: CEO/Founder
Company: https://shop.glou.co
As the Founder & CEO of Glou Beauty, the difficulties that I faced on my journey to becoming an entrepreneur/CEO is that women-led startups received just 2.3% of VC funding, and being a solo, non-technical female founder makes this 10 times more challenging. The gender bias is real and funders often hinted strongly that having a male co-founder will be to my advantage. I wasted a lot of time looking for that partner and the whole process just held me back from building my business.
Choosing to be a solo founder felt right because people were basically telling me I could not succeed until I found a man to partner with. Having to juggle side hustles to save money to outsource certain elements of development hasn’t been easy, and it’s taken a lot slower than I thought it would, but at the end of the day, I’ve built something I’m proud of on my own, and on my own terms.
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Kaley Medina
Title: Founder & CEO
Company: https://www.livelovesleep.com/
I never imagined myself as an entrepreneur. I grew up in a household that believed that if you worked hard for a corporation, that they will take care of you throughout your career. However, after starting my career as a CPA in the fall of 2008 when the economy was beginning to tank, I quickly learned for myself that this was an old school mentality my parents had.
I was seeing my coworkers laid off after only working for a few months. I continued my corporate career for the next 12 years, working my way into a finance position for an oil and gas company. When my daughter was born, she was the world’s worst sleeper. I returned to my corporate job after my 12 weeks of maternity leave and could barely function with the severe lack of sleep. When I sleep trained her at 6 months old, my life was changed forever. I wanted to give other families the gift of sleep that my daughter and I now had. I was feeling unfulfilled in my corporate job and wanted to do something that truly changed people’s lives.
I decided to get certified as a Pediatric Sleep Consultant and start a side hustle while working full time. I believed that it was the safest option to start a business while continuing to work a full time job, as a good majority of small businesses don’t succeed. My biggest challenge when starting off was how to find my target market. I needed to figure out how to let tired parents know that there was help available. And I was overwhelmed with how many different channels there were to market. Should I try SEO with Google, social media, networking with local professionals? I wanted to do them all but felt like I was spreading myself thin and wasn’t very good at any.
So I decided to focus on just one form of marketing to get really good at that, before deciding to embark on another path of marketing. I learned how to get ranked on Google and put all my marketing efforts there for several months until I started to see success. It was only at that point that I decided to move on to social media. And when it came to social media, I didn’t know how to use it for business. I had used it personally for many years but didn’t know how to monetize it. So I decided to invest in a business coach who could teach me what I needed to learn about social media for business. My advice to new entrepreneurs is to be confident with making investments to grow your business. It does pay off if you put in the effort.
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Irete Hamdani
Title: Entrepreneur and Founder
Company: https://www.askbelynda.com/
Everything I’m doing is new to me. From developing the product to vetting the companies to making executive decisions and hiring the right team. It can sometimes be overwhelming.
At the beginning I had a co-founder who was the right choice then, but as time went by I realized they didn’t have the time and budget to invest in the startup and that that was holding me back. We eventually dissolved the partnership. I also had a marketing consultant that wasn’t with a great fit and we discontinued the work. Now I feel I’m on the right track, I have an amazing team, I’m getting the right support and its very exciting!
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Jon Zacharias
Title: Co-Founder
Company: https://gr0.com/
The biggest hurdle I faced in my path to becoming an entrepreneur, in addition to my life more generally, was getting sober. In November 2016 I checked myself into a residential drug rehab center with the goal of getting my life back on track. Not only did the program do what it was intended to, but I met the co-founder of GR0, Kevin Miller, there.
The takeaway from that is that sobriety, for both Kevin and myself, was the driving force behind finding success not only in business, but in our personal lives as well.
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Jaclyn Strauss, CPA
Title: CEO and Co-Founder
Company: https://2ndvault.com
I am a perfectionist and needed to get over myself to be successful. When I launched my own company that I had in development for three years, I needed to put aside some areas that needed work personally to become a successful CEO.
Three years of working on getting everything perfect and the time that I likely lost from getting objective feedback from my consumers and potential clients was lost because I got caught up working to make everything perfect. Little did I know that the most valuable feedback was going to come from the market itself. The only way to receive that feedback was to launch and put the service out there. I used the rule of 3’s to help guide me as to when it was needed to update my product offering.
To elaborate a bit on that, if I heard the same feedback three times, I knew it was a trend and one I had to incorporate. Pivoting the direction the company was going which was originally a B:C to a B:B:C company cost me a great deal both emotionally and financially. I wish I knew what I didn’t know from the start as I would have built my technology differently from inception. My vision was too narrow when I started and I would suggest that anyone starting a company carefully draw out your vision board with everything and anything on it, even if it seems impossible to achieve. You could end up saving yourself down the road.
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Jordan Fulmer
Title: Real Estate Investor
Company: https://www.momentumpropertysolution.com/
As our business grows, it is extremely difficult to maintain a work-life balance. The largest reason for this is that I am still working a full-time job in tandem with running our business.
I am in uncharted territory trying to determine the proper time to leave my job and focus on our business full-time. I know that doing so would significantly free up my time and allow me to grow the business more quickly, but it would also be trading a steady income stream for something more sporadic. Even though it is tough to balance everything, I’m excited to see what the future holds for our business!
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Katie Lyon
Title: Co-Founder
Company: showallegiance.com
At the start of 2020 was when we really started to take off as a company. While we had a massive influx of orders, we didn’t have the product to fulfill them. This was also right as COVID-19 hit, so the American supply chain pretty much came to a halt. I remember having this terrible pit in my stomach every time we saw a purchase come in worrying, “how will we get this customer what they paid for?”
Thanks to our incredible team who didn’t sleep for a few months, we figured it out. The experience made us stronger in the long run, but at the time it was particularly challenging.
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