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8 Big Risks Entrepreneurs Took Over the Course of Their Careers

YEC (Young Entrepreneur Council) surveyed some folks about the biggest risks they took in their careers. Here are their responses.

What is the biggest risk you ever took in your career?


1. Joining a Startup With Over 100K in Debt

Imagine a recent MBA grad on a student Visa with over $100K in debt declining a well-paying job offer to join a startup when the startup had not raised a single penny. It was the risk of a lifetime. However, I had faith in my co-founder who was taking an even bigger risk, and that gave me enough confidence. The risk paid off, and we raised our seed round soon after.
– Ashu Dubey, 12 Labs

2. Deferring my First Job to Travel

When I graduated from college, I had a great job offer. Instead of taking that job, I went to Taiwan to teach English and learn Chinese. At 22-years-old, this felt like a huge risk, but I had an amazing, life-transforming year. In the long run, this taught me to take risks. Life isn’t about checking boxes on the way to retirement. It’s about experiences and challenges.
– Mitch Gordon, Go Overseas

3. Risking Everything for my Own Firm

I was called crazy and people laughed at my face when I announced I was leaving Wall Street to form my own company. It was outlandish enough for a woman to be an executive in finance, but considered absolutely nuts to own your own firm (I’m still one of the only women-owned ones in the nation). I also had absolutely no funding to back my company, so I was risking everything by starting LexION Capital.
– Elle Kaplan, LexION Capital

4. Dropping our Biggest Customer

We had a customer who accounted for 40 percent of our revenue and 100 percent of our frustration. This customer was making everyone unhappy, and I felt it was stifling growth. We decided to let them go in hopes we would actually make up the 40 percent loss and then some. The risk paid off big-time. We experienced a growth spurt that is attributed to this decision.
– Jere Simpson, KITEWIRE INC

5. Creating a Freemium Product That Could Cannibalize Our Premium Product

In 2009, I was running a business called InstantPresenter, which sold web conferencing. As that market grew, I decided that the way to hyper-growth was to tap into freemium, at the risk of losing paying customers. It was all about execution, so we created a separate brand and started offering free services, which ultimately fueled our pivot, got us investor funding and over 800K users. Win!
– Costin Tuculescu, AnyMeeting

6. Starting a Company With a Partner

I started my company with a partner back in 2008 that eventually took a turn for the worst. Putting your career into someone else’s hands is a huge risk. You can take every precaution when finding and taking on a partner, yet there will always be a liability. My company seems to be better off without the addition, yet partnerships are beneficial in many ways. My final words: proceed with caution.
– Joey Kercher, Air Fresh Marketing

7. Quitting Barnes & Noble and Buying a Bounce House

I read the “Rich Dad Poor Dad” book while working at Barnes & Noble and realized I needed income producing assets yesterday. After looking at what I could afford from saving a few months’ pay, I witnessed a man deliver a bounce house for the same price I made in a week. Bingo! I bought one bounce house to start my first company, Sky High Party Rentals. One became two and we are now up to 50 employees.
– Robert De Los Santos, Sky High Party Rentals

8. Working for Free

When I was just out of school, I found the company I wanted to work for, and I walked in and offered to work for free for a month. They hired me on the spot.
– Mollie Elkman, Group Two Advertising




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Young Entrepreneur Council

Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched BusinessCollective (, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

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