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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Adit Jain
Title: CEO, Co-Founder
Company: https://leena.ai/
As you progress through your entrepreneurial journey, the kind of challenges that you face keep changing. For example, right now – almost 4 years since our inception – the biggest challenge I face is scaling our business to $100M in revenue. That said, when we started our journey, there were various issues we faced when it came to sales. We were hardcore techies, straight out of Graduation.
So between us three founders, learning to do sales without the money to hire a team was the first challenge we faced. In the early days, challenges were largely focused around product-market fit, and post that, it was about hiring the best people to build the best solution. That said, hiring the best is a constant challenge throughout a business’s journey. Now, coming to overcoming these challenges. As I mentioned earlier, we were hardcore techies, and sales was something we had to learn from scratch. But we gradually learned.
We understood how to sell to investors and customers. Just to add to that, I was also simultaneously dealing with the fear of “What if someone says no?” But over time, I’ve learnt that you have to be comfortable in your skin 99 out of the 100 times you hear a no. The day you get that lodged, you improve.
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Ajit Soren
Title: Founder @ Ajit Soren Consulting
Company: https://ajitsoren.com/
I have been into executive role, managerial position and even had registered agency. If I had to mention 2 difficulties on the journey, I would say it has to be hurdles in finance and hurdles in having like-minded people in team.
Money is an important factor when you think of scaling and also when you’re not scaling, you need to have the money rotation to keep the day to day work go smooth. Business owners suffer a lot when the threshold payment get stuck or gets delayed for whatever reason. and, another difficulty is not having the right co-partner to work with, there will be times when you don’t agree on certain decision and each one have a valid reason for that. The understanding and trust has to be the foundation if you are choosing someone to go along with you.
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Ankush Sharma
Title: CEO & Co-Founder
Company: https://www.datatobiz.com/
There have been numerous challenges on my path to becoming an entrepreneur, such as assembling the right team with complementary skillsets, always having or devising an alternate plan if something goes wrong, and learning from failure. Finally, making decisions is difficult because it can be stressful.
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Michael Zon
Title: C.E.O
Company: Www.tanjea.com
As inflation rises, finite supply assets (e.g real estate, Bitcoin) continue to become more valuable to offset the decreasing value of the dollar. Tanjea plans to benefit from this inflation hedge due to finite supply assets as it’s in game currency is a limited supply cryptocurrency that is released slowly through the games life cycle. Additionally, our company has intentionally developed our token economic models to ensure the demand for our TNJ token via its in-game utility outpaces any sell pressure from players receiving TNJ rewards.
Since our company holds 15% of all TNJ tokens, which should not suffer from inflation issues given its finite nature, continued funding for operations can come from slowly selling our companies token reserves if our fiat revenue/funding streams become less valuable due to inflation.
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Ihor Prokopenko
Title: Co-founder & CEO at Fulcrum Rocks
Company: https://fulcrum.rocks/
First of all, I must say that to become a successful entrepreneur & start your own company, everybody needs experience and practice. Actually, before turning into success most entrepreneurs fail first. And it’s okay. Any attempt brings extremely valuable insights and experience. For instance, I managed to create Fulcrum Rocks only from the third try.
My first two attempts to create my own product failed, but introduced me lots of challenges alongside valuable lessons. Before Fulcrum, I was working on an e-ticket(card) startup for all Ukrainian students. Our idea was to create an e-ticket which allows students to buy food, tickets etc with a discount. But our main challenge appeared to be a desire to cover a wide scope of services. Instead of focusing only on e-commerce functionality of the ‘card’, we wanted to cover everything at once – discounts, benefits for traveling etc.
Such an approach led us to failure, since each industry, payment system has its own requirements and limitations which we couldn’t consider & handle all at once. It taught me a great lesson – to focus on one thing rather than on everything – which I now apply at Fulcrum. Also, another challenge for me was actually to start doing something.
While I was trying to start my company for three years, I always thought about creating something huge and stuck with planning. But when a crucial moment came, I just had no more time for planning and had to act immediately. That’s how Fulcrum was born – I just decided to start with what I had then. I knew I wanted to be an entrepreneur, I had a tech education, so I looked around for opportunities and found my two other partners. So, basically in 2018 Fulcrum was created by just 3 guys.
We found the first client with a really small project and only then hired our first 3 employees. Financial side of a company could be a problem for us then, but we were lucky to find a team of enthusiasts who focused more on cool experiences than money. Another challenge for me was to grow my connections. When we just entered the industry, there were enough competitors with loud names. But step by step, visiting various meetups, conferences, increasing brand awareness, I could grow my own connections in the tech & business community.
Today, Fulcrum Rocks has almost 100 people aboard, created over 35 projects and continues to grow despite even a horrible war in Ukraine. P.S.
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Ravi Davda
Title: CEO
Company: www.rockstarmarketing.co.uk
I started my first business at 27 years old. Before this, I worked in corporate banking, and was always around people. I’d have a team of people around me, a manager, and people from other teams. We would go out for lunch together, and sometimes, for drinks after work on Friday. When I first started entrepreneurship, this all went away. I was on my own for many hours a day.
My wife was at work, so it was just me and the cat. This is fine for a month or two. I enjoyed the quiet time. But after this, loneliness kicks in. To counteract this, I started working in coffee shops or at the health club I used to exercise in. I would go to networking events and even joined a couple of Masterminds so I could be around people. Now, I make sure I join a co-working space, wherever I am in the world.
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Caitriona McTiernan
Title: Private Tutor and Founder of TPR Teaching
Company: www.tprteaching.com
I think the number one difficulty I faced on the path to entrepreneurship was isolation. It may depend on your type of work, but building a business online, such as a blog, comes with a degree of loneliness and isolation.
You have to give up certain things to achieve your business goals. Usually, this will entail sacrificing days out with family and friends to get your business up and running. While you may get more time when you are established, the first few years takes a lot of work and sacrifice.
Expect it to be a lonely journey unless you find a group that wants to start the business with you. I recommend not completely alienating family and friends but taking time out to be with them, even if it’s just a quick coffee or brunch. Make a conscious effort to surround yourself with people who are a positive influence in your life. They challenge us to be our best selves.
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Tom Greenspan
Title: Founder
Company: https://www.vsmattress.com/
I think I can answer this since I had a rough start as an entrepreneur. Many things didn’t go the way I planned, but my biggest challenge was the lack of planning. Since my teenage years, I was always the impulsive type.
In fact, that is how I started my company. But soon, my business began to falter because I always skipped the planning stage. I had the rude awakening that successful businesses run through planning, not instincts. I had to attend dozens of seminars and watch hours of videos learning the right way of planning. All the areas like sales, development, recruitment, skills shortage, and funding had to be planned to make my new business work. Over the years, I overcame this challenge and made planning integral to my business process. Now, I work to get all the details right, no matter how small.
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Jamie Thomson
Title: CEO
Company: https://rolletna.com.au
There’s no question that becoming an entrepreneur or CEO is a difficult journey. There are many things to consider, from your business idea to your target market to your funding. And, of course, once you’re up and running, there’s the constant pressure to succeed.
But for me, the biggest difficulty was simply taking that first step. It can be incredibly daunting to start something from scratch, especially when it comes to something as important as your career.
But once I took that first step, everything else started falling into place. If you’re thinking about becoming an entrepreneur or CEO, my best advice is just to take that first step. Yes, it’s scary. But it’s also incredibly exciting and rewarding. So go for it! You won’t regret it. —Credit: Jamie Thomson, CEO, Rolletna, rolletna.com.au
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Ben Donovan
Title: Founder
Company: www.brandbuilderuni.com
The biggest difficulty I have faced on my journey to becoming an entrepreneur is learning how to manage money.
Our schooling system doesn’t prepare us for operating a business which presents unique financial challenges and pressures that standard employment would never even scratch the surface of. Learning how to manage cashflow, forecast inventory expenditure, and manage staff salaries is a steep learning curve with dire consequences if mismanaged. Overcoming this has been one of the biggest challenges faced on my journey of entrepreneurship.
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Jacquelyn Son
Title: Astrologer & Business Coach
Company: https://www.divinehealingcircle.com/
One difficulty I faced was the challenge of learning when to let go and when to keep going. When I was younger, I started multiple businesses that didn’t work out because I didn’t start them with the right intention.
I was allowing my ego to lead instead of my intuition. As I gained more experience, I gradually learned how my intuition sounded and learned to pivot quicker when strategies weren’t working. It’s important to not attach your worth to the success of your business. It doesn’t matter how much time you’ve invested into something, sometimes when it’s not working, you just gotta let go and try something new.
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Pee Phirasukprasert
Title: Founder
Company: https://cvproffs.se/
I grew up being surrounded by entrepreneurs so I was naturally a bit more exposed to the life of business owners than most people. It wasn’t a question of if I am going to become an entrepreneur but when. I fondly remembered 2019 when I was starting my very first ‘real’ business in e-commerce.
I had zero clue about what I was doing. I spent hundreds of dollars on advertisements with nothing to show for it. And still to this day, it’s very normal to waste a lot of time and money on things that will never work out. I would say I failed 95% of the time. Can you imagine failing an exam 95 times before you pass it? It’s tough. But the difficulties I experienced over the past few years have taught me to persevere through the hardship. It’s not enough to just “kinda” want it if you are looking to become an entrepreneur.
You have to be, to put it frankly, stubborn to a ridiculous degree. And to do that you will need a solid life goal. This will help you during the rough days and keep you working towards the goal. Another thing to keep in mind is that you should never let other people decide how you live. By becoming an entrepreneur you choose to be different, to be the “weird” kid so to speak.
Many people will give their genuine, well-intended advice like “Why not go get a job at ABC Big Company?”, “If you had taken the job offer you would have made $XXX K by now” etc. Because in their mind, that’s what their perfect life looks like. So to summarize, nothing in business will ever go your way 95% of the time. You will be doubting yourself many times and that’s why it’s important to become a bit emotionally detached from your business. Try to make decisions based on facts and not feelings. This will prevent many mistakes. Lastly, this is YOUR journey and not someone else’s, so don’t let other people’s words affect your decisions. Good luck with your entrepreneurial pursuit.
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Sam Browne
Title: CEO
Company: https://www.haroseo.co/
Here’s how I managed to become an entrepreneur despite the impasses. 1. Failure is inevitable Entrepreneurial success always boils down to having a progressive mindset—it’s never going to be a black-and-white lens.
Most days, you stumble—other days, you bring the trophy home. Accept the fact that failure is inevitable, and use it as a trampoline to bounce back and paint the silver lining to map out how you’re going to reach success.
The difficulty always stems from the beginning—how starting is coined with an influx of setbacks because you lack people. Meanwhile, always remember that when venturing into entrepreneurship, it’s an accumulated effort that blooms like a flower in the future—you cannot grow one overnight. 2. Stoicism thinking Stoicism promotes self-control and fortitude as a method of conquering negative emotions; oftentimes, emotions—like the feeling of failures, get the best of us. Further, emotion has always plagued every entrepreneur’s life, especially when facing difficulties.
Applying this principle to entrepreneurship, such a philosophy claims that becoming a clear and unbiased thinker permits one to comprehend the universal reason of why he or she is pursuing entrepreneurship. In entrepreneurship, there’s going to be a lot of pain, and stoicism portrays one’s capability to bear pain or suffering without complaining. It’s completely reasonable to take rests from time to time, but don’t let it lead to permanence. A successful entrepreneur knows how to draw the line between failure and taking a rest to look back and see the picture from a more comprehensive lens.
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Kevin Mercier
Title: CEO
Company: https://www.kevmrc.com/
Social Rejection Starting my own business made it hard for me to maintain social connections. I did not have any co-workers to chat with, and my friends and family did not understand the unconventional route I had taken.
Plus, with how hard I was working, it was difficult to get out and meet new people or maintain relationships with those I already knew. Luckily, there were other young entrepreneurs out there in the same predicament. I started attending meet-ups with these entrepreneurs, where we would support each other’s ideas and values. Mentally It makes a big difference to have others build you up instead of tearing you down. Focusing on the positive individuals in my life made it much easier for me to put in my best effort.
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