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Entrepreneurship through the eyes of a young CEO

Entrepreneurship is a challenging proposition – one often filled with literal blood, sweat, and tears, but tremendous rewards as well. Let us look at entrepreneurship through the eyes of a young CEO.

jordan fliegel

jordan fliegel

Entrepreneurship is rewarding and challenging

Niccolo Machiavelli once said, “Entrepreneurs are simply those who understand that there is little difference between obstacle and opportunity and are able to turn both to their advantage.”

Ronald Reagan’s assertion that entrepreneurs and their small enterprises are responsible for almost all the economic growth in the United States still holds true today.

More and more, young people are starting companies well before their 30th birthday, and brands are realizing the value of injecting young talent into top positions. But what are the challenges and rewards of entrepreneurship when a company leader is so young?

Jordan Fliegel, CEO of CoachUp, a Boston-based tech company that connects private coaches with athletes of all ages and skill levels, shares with us below his top five challenges and rewards of entrepreneurship through the eyes of a 28 year old:

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Top 5 Challenges:

1. Having to make really tough decisions with limited information. As a leader, it’s really important to make quick decisions. You never have enough time to get all the data, and delaying decisions can have a very negative impact on overall performance and morale on your team.

2. Having to let people go. This is definitely the most emotionally challenging part of being an entrepreneur.

3. Managing your stress levels. When you have no boss, there is no one telling you that its ok to go home. It can be really challenging separating work the rest of your life.

4. Striking the right balance between bottom-up and top-down decisions. Although you have a vision, and want to execute on that vision, you need to balance that roadmap with learning that comes from your colleagues and from your customers.

5. Working really, really long hours. Starting a company is not a 9-5 proposition.

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Top 5 Rewards:

1. Working on a problem that you are truly passionate about solving. There is no greater reward than changing the world in a way that is personally very meaningful to you.

2. Working with a team of incredible people that you help bring together. Entrepreneurship is really all about teamwork and unselfishness. The true measure of a successful entrepreneur is the quality of the team that surrounds them, and the culture that results.

3. Being able to make quick, impactful decisions. Its so fun to see an opportunity, and be able to quickly execute a plan to take advantage of it without needing to play “politics” or wait for management’s approval.

4. Building a culture at work that makes people excited to show up every day. Entrepreneurship is about the journey, not the exit. Its about working hard every day, but also having the time of your life with your teammates.

5. Being really invested and engaged with your work. Loving what you do, and believing in the value of what you do, is priceless – we aren’t going to be around forever… we need to make the most of the precious time that we have!

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The takeaway

While cultural challenges remain for young entrepreneurs, did you notice that the ten points made above are universal? Entrepreneurship has less to do with age and more to do with attitude. There is a dying stigma surrounding youth in the work environment, and Fliegel’s observations above are proof that he could be 28, 48 or 68 and share similar sentiments.

Entrepreneurship is hard work but insanely rewarding, no matter the age of the entrepreneur.

Written By

Marti Trewe reports on business and technology news, chasing his passion for helping entrepreneurs and small businesses to stay well informed in the fast paced 140-character world. Marti rarely sleeps and thrives on reader news tips, especially about startups and big moves in leadership.

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