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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Kevin Yu
Title: Founder/CEO
Company: www.sidechef.com
I am a CEO who never wanted to be a CEO and grew up never knowing how to cook but ended up developing an award-winning cooking app and platform, SideChef. Not only can I cook quite well now (you should try my spinach and artichoke dip one day), I am passionate about transforming the food industry and pioneering new ways people cook at home.
The way my life experiences stacked up formed a wonderful combination of events that led me to pursue this venture. I grew up in a first-generation Chinese immigrant family, where education was the paramount value, and as a male, learning cooking in the kitchen was at the tail-end of priorities. Adding to this, post-college, a career in the exploding video game industry, and having the privilege of working with the most creative minds at Blizzard Entertainment on franchises such as World of Warcraft, Diablo, and StarCraft, learning how to cook or becoming a CEO wasn’t even on the horizon.
The tipping point was when I truly realized I did not know how to cook, especially when I really wanted to impress my girlfriend at the time, and the culinary resources at the time were not catering to people who had zero cooking skills like myself. Combining my lack of cooking skills and knowing there are many out there like me with my video game background, I knew I could create a way for anyone to master cooking, just like how you master different skills in video games.
I am now the Founder and CEO of a food tech company with the mission to evolve the way people cook. Some difficulties I’ve faced – Launching a program or product for the first time is always scary and exciting at the same time – because the truth is, as much as we try to predict what will happen next, the results really can vary. When we were doing user research for using SideChef to guide people through making recipes step-by-step, we had a “mommy blogger” ask if she could share the opportunity to participate in the user research under the premise that parents could cook with their kids taking turns on cooking steps. Within 24 hours, we had 1900 applicants!
We weren’t prepared to handle that many interested applicants, but we changed the strategy and to this day it is still one of our most popular user research projects ever. Since then, parents, together with their children have been a core part of our user demographic. At the end of the day, the solutions you are building may solve problems you never knew existed – and that’s okay. Lean into it.
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Lauren Edwards-Williams
Title: Owner and CEO
Company: https://legendipconsulting.com/
One of the biggest difficulties in my journey was not knowing whether I was making the right decision in taking the big step of quitting my steady income and opening my own business.
This was a difficulty, obviously, at the beginning of opening the company, but it was also a difficulty when I would have set backs or if some step in my plan hadn’t gone how I thought it would. Another difficulty I faced was finding people I trust to join my company. I am a perfectionist and very particular about my work, so I needed people that share the same passion and drive to be the best and do the best for our clients.
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Lesley Hensell
Title: Co-owner
Company: https://riverbendconsulting.com/
In my early career, I was a journalist and then became a business/marketing consultant. Then about 10 years ago, I became an Amazon seller when I was looking for a way to earn money, but also stay at home with my two sons, both of whom were dealing with serious health issues and other challenges.
In those days, it was important to have the flexibility that came with being an Amazon seller, because it also gave me time to be there during my son’s chemo treatments, while also providing an income to pay for those treatments as well as my other son’s special needs schooling. Running a business while dealing with the stressors of what my kids were going through taught me so many lessons about patience, perseverance and a broader understanding of the bigger picture. But what started out as a way to earn income out of necessity ended up becoming the pathway to a very successful business idea. From my day to day dealings as an Amazon seller, I was able to see the challenges that ecommerce business owners faced everyday.
I soon became a consultant to others, helping them through those challenges, and that eventually led me and my co-founder to starting Riverbend Consulting. But more importantly, I think the stresses I went through in the beginning helped me understand what my clients are facing. After all, it can be very scary and stressful to have your account suspended, and not be able to make any money, especially when it is your sole source of income.
Today, our company has 60+ employees all over the world who solve critical problems and offer effective growth strategies for sellers on Amazon and other ecommerce platforms. We have helped thousands of sellers get their accounts and/or products reinstated and also offer effective strategies for further growth. My lessons along the way have really helped me identify with other business owners’ challenges, and have helped me work with them in a compassionate and patient way.
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Matt Zavadil
Title: Marketing Coach
Company: https://mattzavadil.com
The biggest challenge I faced early on was the inability to focus. Many entrepreneurs own an “abundance” mindset. While that mindset is necessary, our tendency to have multiple interests can fail us. Early in my career, I started projects. Then, I would start a second or third project before the first project completed.
The advice I give to my clients most often today is this: Don’t start a new company or project until you’ve made a contract with yourself to see it through to completion. Focus. Deal with the inevitable roadblocks and disappointing results early on. See it through. Overcome the obstacles until the job is done. The ability to focus one’s entire capacity regarding energy and commitment isn’t discussed enough in the entrepreneurial world. The tenacity to see the project through is more important than current skills (you will learn more as you go). Focus and never give up.
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Megan Moore
Title: Founder
Company: https://photography-lighting.com/
One of the difficulties I’ve faced as an entrepreneur is a challenge of having multiple responsibilities.
Not only am I a photographer and videographer, but setting up Photography-Lighting required me to wear several hats as a marketer, content writer, and strategist. Though challenging, I have loved every second of the journey.
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Paige Arnof-Fenn
Title: Founder & CEO
Company: www.MavensAndMoguls.com
My biggest challenge was that the people you start with are not always the ones who grow with you. The hardest lesson I learned when I started my company is not getting rid of weak people earlier than I did in the first few years of my business.
I spent more time managing them than finding new customers. I knew in my gut they were not up to snuff but out of loyalty to them I let them hang around much longer than they should have. It would have been better for everyone to let them go as soon as the signs were there. They became more insecure and threatened as we grew which was not productive for the team.
As soon as I let them go the culture got stronger and the bar higher. “A” team people like to be surrounded by other stars. It is true that you should hire slowly and fire quickly. I did not make that mistake again later on so learned it well the first time. I wish I had known it even earlier though but lesson learned for sure! Another key challenge has been about the importance of focus.
There is so much noise out there with social media, 24/7 news, climate change, etc. that for my clients and me staying focused with all the distractions we are bombarded with on a daily basis can be tough. So my top tip is to learn to give yourself permission to say no. Whether it means passing on joining another committee, delegating to someone on your team to attend the event, sleeping in (no to an alarm clock), meditating, taking a walk, or just turning off my phone and computer (no I will respond later on my own schedule), simple acts of letting myself focus, relax and be present in the moment are the very best gifts I can give myself as an entrepreneur.
Like most small business owners and entrepreneurs there are never enough hours in the day to fit everything in so when something has to give it is usually time I have allocated for myself to think, exercise, read or just relax. What I have come to appreciate and realize in my 50s is that “me time” is not a luxury or pampering like it was in my youth, now it is maintenance! To improve productivity in my experience when you focus and do less you can get more done. I also recommend NOT spending money on things like fancy brochures, letterhead, business cards, etc. Until you know your business is launched I would say to put your budget into things that help fill your pipeline with customers.
Getting your URL and a website up and running is key. I created online stationery for proposals and invoices, ordered my cards online and made downloadable materials as leave behinds for people looking for more information to help me find clients more quickly. I know other business owners who spent thousands of dollars on these things and found it was a waste of money.
Your story will evolve as you find your market, you need to look professional and have a web site to be taken seriously but embossed paper with watermarks and heavy card stock is not going to accelerate your sales cycle. Find those reference customers quickly, use them to get testimonials and referrals. There is plenty of time later to dress things up!
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Rohan Kadam
Title: Owner of Biking Know How
Company: http://bikingknowhow.com/
Hello, I am a marketing consultant and an established entrepreneur.
I run a successful Niche website called Biking Know How.
I would like to share how I quit my job as a banker at JP Morgan Chase and started my blogging business and turned it into a successful business. I started my blog just as a hobby. I scaled my business, especially during the challenging COVID pandemic, and made it profitable in a short period (From the first month itself).
I focused on doubling down my efforts on growing my niche website, which was initially just my passion project. I would say that my online business has helped me stay occupied, motivated, and financially stable. I love the outdoors, biking and camping. I always wanted to share my unique experience with people. Initially, I would maintain a diary and would write about my outdoor camping endeavors. Thanks to social media and my website, my audience over time has increased significantly.
With social media and my website, many more people can access my adventures and plan their own. This gives me immense joy and fulfillment. Some of the details on my blog are as follows.
1. Bikingknowhow.com is my third blog (I run 2 blogs currently, all in different niches. I sold my first blog) that I had started. And it today gets approximately 5,000 monthly unique visitors. I earn money through two Ad-Networks namely, Google AdSense and Media.net which show ads on my website. (I make a minimum of $200 per month with both ad networks combined).
2. I also partnered with Amazon via an affiliate partnership, and I promote the products and services of Amazon on my website (I make approximately $100 per month) by promoting products on my blog.
Challenges/Difficulties: As far as the hardest part or challenges are concerned, I had to face many, but two challenges stand out the most.
They are as follows.
1. Time Management: This was a very significant challenge because I was managing and growing my blog while having a full-time job. I would use my weekends and holidays to educate myself on skills, especially web development and digital marketing. My blog allowed me to have multiple streams of income. As I saw decent cash flow coming in, I was interested to upskill myself on digital marketing and social media. I knew this would require my time and dedication. So, at every opportunity that I got to polish my skills, I made sure that I dedicated my time and attention to get better.
2. Getting Right Education: Well, to educate and polish my skills in digital marketing, I enrolled in many digital marketing and web development courses. I used courses like Authority Lab and Nite Site Project to teach myself affiliate marketing. I started voraciously reading blogs and success stories of affiliate marketers as I found them very inspiring. This helped me get creative and experiment with the growth strategy of my blog.
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Marc Lamber
Title: Founder
Company: https://lambergoodnow.com/
Delegating tasks has been the greatest difficulty of my entrepreneurial journey. Ideas have to scale up to become businesses, and with larger operations, it gets harder to do everything yourself so delegating tasks is important. I struggled at delegating the core tasks and responsibilities to my teams since I couldn’t entrust anyone with them.
However, it was not productive and stalled our growth for long. I had to change my management style and subdue the temptation to do everything myself. Instead, I took a monitoring role in my business and let others accomplish objectives. For effective delegating, it is important to define clear roles and responsibilities and rewards for meeting specific targets. Micromanaging people is a bad idea for entrepreneurs. It is good to give your employees some space to use their talents and prove their worth to the company.
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Renee Fry
Title: CEO
Company: www.gentreo.com
One major difficulty in becoming an entrepreneur/CEO is realizing that there is no right time to start a company. You have to make the right time happen. Whether it is the people that you surround yourself with or the time that you put in, you have to make the decision that you are going to make your business thrive.
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Sergio Diaz
Title: CEO
Company: https://keynotespeakers.info/
The biggest challenge I have faced is being able to quickly pivot and adjust when I discovered something new about my business model.
This is my third company and I can tell you for sure the first two years are the hardest because you start the business with certain assumptions, then when you dive into the business you discover new insights about it, and if you cannot quickly pivot and adjust from what you have learned, it can be hard to recover.
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Roberta Perry
Title: Founder/Owner
Company: https://scrubzbody.com
All indicators point towards a long term inflation, how are you preparing your business for the upcoming challenges? Share some practical advice. Because we have both a private label and a retail business, we have always had to be very sure of our margins and allow for fluctuations in the cost of goods.
I managed to keep prices the same for 4 years and only recently had a 8% increase on certain products. We were able to maintain the same price on quite a few items because the margins were better to begin with, so we absorbed the cost and made our customers happy.
Which is what it’s all about anyway. 🙂 As we move forward into long term inflation, I am willing to purchase larger quantities of raw materials, so I save big on shipping as well as enjoying any bulk discounts. I will ask local makers if they want to purchase items together so we save even more. I will streamline systems that need tweaks to make them more efficient which in turn saves money. I will continue to grow my business one customer at a time. And then they bring family and friends.
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Sarah Turner
Title: Founder
Company: http://sarahturneragency.com/
In the beginning, it definitely wasn’t easy. When I was first becoming an entrepreneur, I didn’t think that I could become one or had what it takes or even what that looked like because I certainly wasn’t a ‘risk taker.’
My first business was an event planning business and I just kind of did it because I hated my job so much, but I’m glad I started it because it showed me how easy it was to start a business in the first place whether I had a degree or not. Suffice it to say, I had a lot of imposter syndrome. The next difficulty was money. I utilized a lot of free resources and changed my mindset around money in the process.
The way I’ve overcome both was by easing into everything. I think the thing that helped me overcome both of those difficulties was the realization and understanding that it wasn’t going to just be one big dramatic shift that happened overnight. It was gonna be small, consistent actions that compounded over time.
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Tiffany Burris
Title: Owner
Company: https://squishface.com/
As a way of battling inflation and a possible recession (as well as possible supply chain issues as a result) we’ve prepared for the future by buying larger than normal production runs for our product as well as bringing order fulfillment in-house.
If the economy does take a hit, it’s a lot easier to sell product when you already have it vs. trying to scramble and get more inventory when there’s a good chance lead times will increase as well as unit costs. Further, we’ve brought our order fulfillment in-house and opened our own warehouse so that orders are cheaper and faster to ship out vs. relying on a warehouse to do fulfillment that may or may not have the best shipping prices and who’s priority is their bottom line and not a business’ customers.
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Rogers Healy
Title: Owner/CEO
Company: www.rogershealy.com
Growing up, I felt like I was failing more than I was winning. Even during my early career I sometimes felt like a perpetual failure. When I decided I wanted to become a real estate agent, it took me 22 times to pass the real estate licensing exam.
That might be more times than anyone in the state of Texas has taken it. The biggest struggle of entrepreneurship is maintaining persistence. Remaining tenacious and never giving up is what got me to where I am today. As they say, nothing good comes easy.
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Reece Kresser
Title: Founder & CEO
Company: https://www.zizi.co/
My journey as a Founder & CEO started after I quit my full-time job in investment banking. From there, I sold my family home, staking everything on my startup and a passion for accessible healthcare.
We were finally ready to launch when I realized that our supplement’s manufacturer’s capsules were animal-based and the planet sterols inside weren’t non-GMO certified. Financially, it made sense to move forward. After all, switching to a vegan supplement source would cost thousands, lower our margins, and delay our launch by at least a month.
But that’s not what Zizi is all about, and it’s not what I wanted for the people who would be looking to us for healthy, science-based ways to lower their cholesterol early and proactively. Instead, we chose a better manufacturer without passing the extra cost onto our customers. We’re proud of the decisions we’ve made thus far, and we intend to keep making business decisions with our customers in mind.
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Maria Burgos
Title: Founder & CEO
Company: https://www.trendyseconds.com/
I’m an immigrant from Venezuela with 4 years living in this country. The first challenge here was to build a strong network. I did that after going through an acceleration program and continue to do so on a weekly basis. Learning how to do this and reach out to people has been a great way to connect and learn from fellow founders.
The second challenge was to launch a tech-enable startup with no technical background. The velocity I have to learn and the costly mistakes along the way have forced me to deep dive in the technical aspects while managing the business as a bootstrapping solo founder. And of course, as a mom of two toddlers I’m always striving to create harmony in all aspects of my personal and professional life, which on its own represents the biggest goal. Back in my country, I started two companies, both failed.
The economical and political situation mixed with the lack of resources for entrepreneurs, makes it more challenging to succeed there. Here in the US, I was able to go from idea to launch within a pandemic year, no technical background, no previous network and two kids at home. It’s challenging, but if you’re curious and learn to be resourceful, doors start opening.
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Ryan Montgomery
Title: Co-CEO
Company: https://www.becomeanything.com/
Second-guessing As the sole business owner, I was supposed to make all the big decisions. And the most challenging part was never knowing if I was right. I second-guessed myself on several occasions and found it hard to cope with that feeling.
The fear of being wrong was a major factor affecting my decisions. Over the years, I have come to terms with this feeling. I have realized that no one, especially an entrepreneur just starting, is capable of making the right decisions all the time.
Being wrong is a part of decision-making and a part of who we are. You must have the confidence to take full responsibility for the outcomes of your decisions. Looking back, I can confirm that I do not regret or second guess any of my decisions, even the bad ones. Entrepreneurs having self-doubt should have some faith in themselves and keep moving forward.
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Trey Langford
Title: Founder, CEO
Company: https://www.buildidaho.com/
All indicators point towards a long term inflation, how are you preparing your business for the upcoming challenges? Share some practical advice. Real estate is already seeing signs that the economy is shifting and now is the time to get in front of it.
The challenge is how to handle it. Do you cut expenses to keep the doors open or increase marketing dollars to sway the fewer available prospects to select your services? We take a two pronged approach: Goals and Budget It is easier to understand how things are going if you have regular check points to compare against. Being able to see units, revenue and expenses against goals and budgets show where you are and where you are headed. Just looking at a P&L may not help identify soon enough that your pipeline is drying up. No matter the strategy, everyone must be committed to it.
The plan must be granular so it is clear what has to happen and who is going to do it. The more detailed the plan, the better. Having an inter-dependent team will become critical as the economy shifts because we need to depend on each other to keep moving forward and maintain stability.
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Warner Quiroga
Title: President/Owner
Company: https://www.prestigehomebuyers.co/
I’ve always wanted to be my boss and lead others, so I knew being a CEO was in my blood. I always had that gnat to go out and be creative and make the most out of what was given to me. I faced many rejections, people who doubted me and mistreated me, but it all shaped me and prepared me for who I am today.
So, I made sure that with each obstacle, I learned something from it, not to commit the same mistake and always to know that there’s someone out there that’s doing the same as me, if not more, and they were given fewer resources at their disposal. I’ve always wanted to have the ability to learn things very quickly as some people do. Instead I have to work twice as much I think to really understand something. I think the benefit to that though is that it has made me very resilient and patient. Because of this, I am always grateful.
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Tim Connon
Title: Founder CEO
Company: https://paramountquote.com/
Self funding my business and developing the mental strength to not give up.
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Shakib Nassiri
Title: Founder and Owner, WAMA Underwear
Company: https://wamaunderwear.com/
If It At First You Don’t Succeed The old maxim about failing and trying again until you get it right? In my case, that’s absolutely true. I’ve always believed that the future of clothing lay with hemp, but it’s taken the rest of the world a decade to catch up with me. When my first business failed, I was despondent and packed my bags and decided that I wanted to travel for a while.
It took around six months for me to start thinking clearly about the next step on my business journey, but while I was hiking in China, everything suddenly fell into place, and within a month, I’d launched WAMA and the rest, as a wise man once said, is history. The path to success is a difficult one and you fall and stumble along the way, just like I did. It will be painful, and until you find that one thing that ignites your entrepreneurial passion, there’ll be more bad days than good. But when you do find it, everything will fall into place and the world will be yours for the taking.
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