5 Challenges Founders Face When First Starting Up

Running a startup isn’t as intuitive as some people think. Like most things, the more experience you have under your belt, the more prepared you will be to tackle the many issues that plague startup founders in any and every industry.

We asked five founders what their biggest challenge was when starting their business and why. Check out their answers below:


Focus is a constant challenge. Entrepreneurs see opportunities left and right and without focus, you spread yourself too thin which ultimately weakens your chances of success.

– Ben Maitland-Lewis, founder of Pretty Instant

Being the Visionary

Once you build your product, the hard work really begins. Having conviction in your idea is one thing, but following through with actions is the scary part. Once you build something you have to undergo a shift in attitude in order to put it all out there and prove it works.

– Jessica Baker, founder of Aligned Signs

Making a Name for Your Business

Gaining trust of my clients was the biggest challenge and I think that most startups experience this. Why should they work with me versus someone who’s already an established brand? You’re a wild-card; an unknown. You might be great to work with, but since you aren’t an established brand, you could also be a catastrophe waiting to happen.

– Steve Buchwald, founder of Buchwald & Associates

Convincing Loved Ones

Coming from a conservative family, my parents especially believed it was important to choose a conservative profession. They wanted me to work an office job and build a steady income. When I had told them I wanted to start a new company, I was met with resistance, but in the end they understood my decision and accepted it.

– AJ Saleem, founder of Suprex Learning

Getting Our First Client

It took ages to get my first medical transcription client, and once we did it was off to the races. It was difficult to tell prospects to just trust me when all they wanted to do was speak to references, which we didn’t have, yet. Once the first office gave us a chance that’s all we needed, because we were able to capitalize on that and grow very quickly.

– Ben Walker, founder of Transcription Outsourcing

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Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. YEC members generate billions of dollars in revenue and have created tens of thousands of jobs.
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