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10 Questions to Ask an Entrepreneur

Written by:

Carolyn Young is a business writer who focuses on entrepreneurial concepts and the business formation. She has over 25 years of experience in business roles, and has authored several entrepreneurship textbooks.

Edited by:

David has been writing and learning about business, finance and globalization for a quarter-century, starting with a small New York consulting firm in the 1990s.

10 Questions to Ask an Entrepreneur

If you’re thinking of launching a business for the first time, it helps to prepare yourself with as much entrepreneurial insight as possible. The more you know, the better your chances of success. 

You can take classes and read books about entrepreneurship, but the best guidance will likely come from an experienced entrepreneur. If you do have a chance to speak to one, here are 10 questions likely to result in responses that are full of invaluable entrepreneurial wisdom. 

1. How Did You Come Up with Your Idea?

business person holding paper sheet with question mark

Many people have entrepreneurial aspirations, but they have trouble coming up with a great business idea. If you ask an entrepreneur this question, one answer you might get is that their idea came from a need to “scratch their own itch”, meaning that they had a problem and decided to create a new solution for it. It also might be that they were following their passion or simply decided to do something they know – like a hobby turned into a business. In any case, their story might jumpstart your thinking. 

2. What Inspired You to Be an Entrepreneur?

businessman raising hand to ask question

The motivation to be an entrepreneur can come from anywhere. Very few will say “I wanted to make lots of money”. Making a living is usually a factor, but most entrepreneurs want to build something of real and lasting value and have great passion and a clear vision. The responses you receive might help you explore your own entrepreneurial inspiration and make sure you’re doing it for the right reasons.

3. How Did You Overcome the Fear of the Risk You Were Taking?

thoughtful businessman planning future project

Entrepreneurs often seem fearless, but they are human, just like everybody else. When they take business risks they are not immune to anxieties. You’ll likely find that the entrepreneur had to do some serious thinking before taking the plunge, and you may well learn some lessons that will help you overcome concerns and worries about your own business. 

4. Did You Quit Your Job Right Away?

unemployment man leaving the building

Many entrepreneurs struggle with the decision of when to quit their job to work on their dream venture and their personal story is likely to provide some valuable insight. Quitting to embark on a new venture is a huge risk, so many entrepreneurs start their business as a side hustle. Either way, the entrepreneur should be able to detail how they managed their time and made the transition. Planning your own transition is an important part of your preparation. You’ll be making a huge lifestyle change, so you’ll want to find the best transitional path. 

5. How Did You Raise Startup Funding?

start up funding business idea concept

Ah, the age-old question. How in the world can I get money to start my business? Raising capital for a startup can be a monumental challenge. Most are too early in the process to attract investor interest, and even bank funding can be hard to come by. Many entrepreneurs give up all their assets to pursue their dream, while others get funding from friends and family. Some entrepreneurs find creative ways to obtain resources. Every entrepreneur has a different story, so you may find options for your business that you haven’t thought of. 

6. How Did You Build Your Team?

teambuilding activity at group meeting

Entrepreneurs usually build a team from the start, rather than go it alone. Some entrepreneurs outsource many functions, while others take on a partner with complementary skills. Some hire one or two key people to take the journey with them until they can build a full team. It all depends on your capabilities and your type of business, but another person’s experience can help you craft a more sensible plan. 

7. What Keeps You Motivated?

confident young businesswoman

Entrepreneurship is rarely easy. You’ll likely have to eat, drink, and sleep your business to be successful, and it’s easy to get burned out. You might start asking yourself why you began this arduous journey. Something has to keep you going, and that thing is different for everyone. Hearing a successful entrepreneur’s motivations might give you some insight into your own and provide a boost as you face new challenges. 

8. What Do You Think Was the Key to Your Success?

business team corporate concept

Many entrepreneurs are able to point to a single moment or decision that put them on the road to success – a certain hire, a tweak to their main product, acquiring VC funding. Whatever their answer, it could spark some ideas that help drive you toward success. 

9. What Mistakes Did You Make?

unhappy businesswoman working on paper work

This may well be the most important question of all, and one answer that you are highly unlikely to receive is “none.” Every entrepreneur makes mistakes, but the successful ones learn from them and improve. Knowing the mistakes an entrepreneur made might help you avoid a few of your own. You can also find out how they overcame the mistakes and kept the business going. How you deal with small failures can make or break your business. 

10. Do You Have Any Regrets?

businessman thinking over company future

This question should come with some interesting answers, but if the entrepreneur is satisfied with where they are at this point, they may tell you “no”.  If everything they did, mistakes and all, lead to success, they might not want to go back and change anything. Others may have some regrets, but they probably don’t have regrets about taking the journey. 

Entrepreneurial success offers so many rewards that the challenges and tough times are worth it. The response you get to this question could determine your answer to the crucial question: “Should I become an entrepreneur?”


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10 Questions to Ask an Entrepreneur