From YEC: How to Overcome Unexpected Startup Challenges

Getting Others to Take You Seriously!

“Being young was by far the biggest challenge I faced when starting out as a young entrepreneur. People often wouldn’t take me seriously. It’s a tough challenge to overcome. You need to stay persistent, show your full commitment, and most importantly, produce a great result. Build up a reference list of a few happy clients, and they will build the credibility you may be missing.”

Not Knowing My Own Value

“It can be tough to prove yourself to prospective clients when there are so many other players. Unfortunately, you won’t receive respect from others until you respect yourself. As a newbie, it’s natural to feel self-doubt. But my business didn’t really take off until I realized I had something valuable to offer… and began demanding to be paid what I was worth.”

Underestimating the Skill Set Required for Success

“My biggest challenge as an entrepreneur has been acquiring the technical skills I need to be successful. Launching a business online without a technical background was difficult, but I overcame this obstacle by surrounding myself with skilled people, furthering my education and staying persistent.”

Making Time to Start the Business

“I started 3Ring Media as a result of an opportunity to work as an independent contractor with Chicagoland Skydiving Center. I vowed that I’d network my face off and have potential clients lined up by the time the season ended in November. July rolled around and I hadn’t done anything. I panicked. Make time to start your business, but don’t rush it if you get behind.”

The Challenge of Cash Flow

“Until I was in the midst of running my business, I had no idea how crucial cash flow really is. Even if I’m “owed” $5,000 in a certain month, that means nothing if bills need to be paid and the check from my client hasn’t yet arrived. Keeping this in mind and creating safety nets is something that took me a long time, something that is crucial for the success of my business.”

Being Realistic About True Love

“It is very dangerous to fall in love with an idea without having spoken to customers or tested it in the market. When customers tell you that what you built is mediocre or a “nice to have” but not a “must-have”, then you need to start over. Cut the losses, no matter how much time you spent developing that “mediocre” product. Don’t stop until you’ve found the truth: a product that people love.”

Proving That Age is Just a Number

“The biggest unexpected challenge for me when starting my first company was proving that my age was just a number. I was smart, prepared and driven, but I had to be strategic about how I entered an industry that was full of seasoned professionals. My colleagues and future employees were oftentimes decades older than me. I had to learn how to manage and communicate my expectations.”

Realizing I Couldn’t Do It All

“It’s like when you’re a kid and think you are invincible. I started out thinking I could do it all and quickly realized that was a lie. Being creative is one thing but creating a website is another. I spent so much time trying to do that, that it took away from building the business. Know what your strengths and weaknesses are; focus on the strengths and delegate the weakness.”

Getting Those First Customers

“Getting customers is very difficult. You are trying to change someone’s habits and have them give you their hard-earned money — the difficulty of that cannot be understated. You will need to use every available method, from PR, to marketing, to talking to everyone you know and meet, and grinding any way you can. Getting your first customers is tough, so be prepared to work very, very hard at it.”

Learning to Let Go

“In the beginning, I had trouble delegating tasks to other people which is a common problem many entrepreneurs face. What I did not expect was the way to overcome this had nothing to do with me. It had to do with the people around me. As entrepreneurs we have this gut feeling if we can give someone a task and they can run with it on their own. When you find that person, just let go!”

Adopting the Marketing Angle

“I was really passionate about what I had to offer to the world, but I wasn’t sure how to get the word out and sell my services and products. To overcome this, I absorbed everything I could related to online marketing, traditional direct marketing, and social media. It payed off — big time.”

Trying To Grow Strategically

“When I started my last company, I knew I was about to take on a very big workload, but I never expected outgrowing myself so fast. I didn’t have the right systems in place from day one to scale my own time, and that really hampered growth as I was now doing too much fulfilling and now enough selling to continue to grow my business. Never thought that would have been the case getting started.”

Figuring Out How to Scale Well

“From the day I started my business, I wanted to build it up as fast as possible. I’ve had to figure out ways to rein myself back in because there’s just no way to scale up as quickly as I would like — no matter how attractive the idea seems in my head.”

Accepting That Things Take Time

“I had no idea how long everything would take when I first started the business. Everything, from creating a webpage to finding a first customer to hiring an employee, takes 2-5 times longer than you’d expect. The solution: be patient. Good things will come… just not immediately.”



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