15 Questions To Ask an Entrepreneur If You Want To Become One

If you’re constantly asking yourself how long does it take to become an entrepreneur, you may not have the mindset to make it. The good news is that, once you figure out how to not completely suck at becoming an entrepreneur, you’ll see plenty of both types of moments. But when you’re starting out, the latter tend to outweigh the former by a considerable margin.

How to become an entrepreneur

Think it

If you’re trying to come up with your million dollar idea start by thinking about what you enjoy doing. You’ve likely heard the “follow your passion” advice and that can work for many, however, it’s not the only ingredient in the recipe for success.

Spend some time thinking about what you can offer

Consult your friends and family

Do you need additional qualifications?

Once you’ve brainstormed some viable ideas consider if you will need any additional education, certificates, or experiences to start your business.

For instance, if you want to own your own plumbing business you can bet that most of your potential clients will want to know that you’ve got some plumbing credentials under your belt! No one wants to deal with an amateur when their toilet is overflowing.

Find a mentor

If you know someone who you look up to, who has done what you want to do, then reach out to them and ask them how they did it. A good mentor can motivate, inspire, connect and guide you.

They can also help you to avoid a ton of unnecessary mistakes.

Research it

Is this a viable business opportunity?

How much will it cost to get your business going?

To get an estimate of how much it will cost to get started, you’ve really got to calculate your startup costs to breakdown with as much specificity as you can – to generate what your actual real numbers are going to look like.

How will you fund your business?

  • The bank of YOU – Maybe you’ve been dreaming of your entrepreneurial adventures for years and you’ve socked away some cash, time to dip in! If not, you’re young, you have boundless energy – if you can manage it, get a job, or two, or three to help you fund your dreams.
  • Hit up family and friends – Honestly, this one makes me uncomfortable because relationships can go sideways over money, however, if you have family members or friends who are very well to do, or at least have some disposable income to play with, then ask them if they’re interested in investing in you. Just make sure everyone is on the same page when it comes to the terms (when will the money be repaid, are they charging interest, etc.)
  • Personal business loan – If you have a decent credit score you can look into a personal loan to fund your business. Companies such as Prosper offer fixed rate, fully amortizing, unsecured loans from 5000,000 to $40,000. If your business takes off immediately and you start raking in the dough there are no penalties for paying off your Prosper loan early or for making partial prepayments.
  • Credit If you’re looking to gain access to money quickly, then consider a business credit card. Similar to a loan, access to a business credit card is dependent on your personal credit. If you decide to use a credit card to help fund your start-up make sure you check out the interest fees to avoid a hefty and unexpected bill!
  • Crowdfunding – If you have an amazing idea that is going to add tons of value to the public, then why not ask them for donations. Crowdfunding has become popular over the last decade and has helped many entrepreneurs bring their business ideas to fruition.
  • Government grants – Depending on the type of business you’re hoping to open you might qualify for a government grant. A grant provides free money, which is amazing, but they generally have strict criteria and the application process can be tedious.

Test it


Go beyond your friends and family and ask strangers (a.k.a potential clients) if they would purchase your product. If you have a tangible product, take it to a tradeshow. In order to meet people in your particular field of interest, attend a convention or conference.

Join a mastermind

Get involved with a group of like-minded individuals and help each other brainstorm ideas, navigate challenges and share expertise. Entrepreneurship can be lonely, so take some time to find and build your tribe.

Plan it

Create an action plan for your business

Do it

Make a sale

Market yourself

Keep networking

Research conferences, tradeshows and local meet-ups related to your business. There is nothing more valuable than meeting potential clients, partners or possible employees in person. Also, stay active on social media.

Improve it

Embrace criticism



Tips for young entrepreneurs

Don’t quit your day job

Study your competition

Stick it out – there’s no such thing as overnight success

Know your worth

There’s never a “good time” to start, so start now

“My company started as a blog in 2017. I wanted to share what I’ve learned through my own journey to financial freedom, what has worked for me, what did not work for me, and my thoughts on hot financial topics. My friend told me to start a blog to share my tips, resources, and advice.

I didn’t know much about blogging but I created my site and started an Instagram account. When I was sharing my blog posts on social media, I would get a ton of DMs from people asking follow up questions or telling me what they were struggling with. People could relate to my journey and loved the advice I was sharing.

In 2019, I launched my money coaching business and I had 6 1:1 clients within two months of launching. I now have a group coaching program in addition to my 1:1 coaching. I absolutely love what I do. My company is my passion and helping my clients reduce financial anxiety, increase their income, and dream big has been so rewarding for both my clients and myself.

It is not easy and I am constantly learning, but I love it.

There is never a good time to start so start now. Life will always be hectic. Your week will always be busy. You need to stop making excuses and invest in yourself and your future.”

15 Questions to ask an entrepreneur

1. What inspired you to develop your idea?

Entrepreneurs are individuals who successfully transformed an idea from theory into reality. Executing an idea can require confidence, commitment and determination. Learning what motivated an entrepreneur to take action toward implementing their idea can help you evaluate your own ideas, motivators and challenges.

2. How have your priorities changed from when you first started?

Often, as entrepreneurs explore ways to develop their business, they have one goal in mind: success. In the early stages of an entrepreneur’s career, they may have perceived success differently than they do now. Drawing on your interviewee’s career experience and personal growth can help you evaluate your own priorities.

For example, they may say their priority now is creating happy, productive teams and a healthy work culture. In the beginning, their priorities may have been more centered on growth. They might reveal certain considerations you can incorporate to find earlier success.

3. Knowing what you know now, is there anything you would have done differently when you were first starting out?

Learning what an entrepreneur would have done differently can help you make smarter choices up front. Try to find ways you can incorporate their answer into your early strategy and use them to guide some of your own decisions. They might provide valuable lessons that can help you grow your business and mitigate risks. Maybe they reveal areas where they spent too much time and energy that didn’t generate a positive return, or they could share actions they would have taken sooner.

4. How did you decide where to establish your company?

Where you offer your products and services can have a large impact on your success. Listen for their top considerations when deciding where to market their offerings. They may reveal decision-making factors that influenced their success or explain location aspects they wish they’d known sooner. Whether they market their products remotely or in a physical store, you can learn a lot from their criteria and use it to influence your own deciding factors.

5. What challenges did you have to overcome at the beginning of your journey?

In entrepreneurship, some challenges can be inevitable. However, learning what to expect can help you prepare for challenges before they arise. Not all challenges are negative, learning from early obstacles can help you grow your business, refocus your efforts and teach you important recovery skills. Their answer to this question can also reveal a lot about how much they overcame to achieve their success. Stories like these can serve as inspirational reminders to persevere even when things don’t go the way you expect.

6. What is unique about your business?

A key quality of many entrepreneurs is their innovation, or ability to offer something interesting and new. Their ingenuity can help them rise above the competition and find success in their own, unique way. Learning what unique strategies an entrepreneur employs can help you understand what differentiates successful new businesses from their competitors.

7. What advice would you give to someone who is trying to become an entrepreneur?

Established entrepreneurs likely have experience they can share that may help you on your journey. Asking general questions like this can encourage your interviewee to consider factors you might not think to ask them about. Try to use their response as guidance for creating actionable steps you can apply to achieve your goals.

8. How did you first select your employees?

As companies grow and teams expand, many entrepreneurs find they need help. Deciding who to bring with you in the first part of your journey can have a large impact on the direction your business goes. Especially as a new business with a small team, individual’s contributions can shape your company. By asking what early steps an entrepreneur took to develop his team, you can determine important hiring and partnership considerations.

9. How did you raise funding?

Often, one of the biggest obstacles to starting a new business venture is funding. Finding interested investors and sponsors can take time, patience and persistence. You can learn a lot from experienced fundraisers. Try to find out where they started looking for investors, how they persuaded others to accept their vision and what strategies they took to get started with limited funds. They may provide valuable advice like presentation tips, outreach strategies and budgeting processes.

10. What strategies did you first use to market your business?

For a business to grow, it’s often important for them to connect with and expand their audience. Marketing can be an investment, and using your money wisely can help you raise awareness of a product or service without spending all your resources early on. Incorporating established marketing practices that led others to success can help you focus your efforts and develop marketing plans that accomplish as much as possible.

Key Points for Aspiring Entrepreneurs to Remember

That being said, for all of the perks that the entrepreneurial path offers, it’s far from being all roses. Far from it. Being an entrepreneur means being a warrior. It means being a clever, hungry, often ruthless competitor.

In that sense, I believe that entrepreneurs are not too different from UFC fighters, Spartans. Their fights are not meaningless brawls. They’re a result of being willing to stand for something, to risk everything for a chance of success and to grow in the process and maybe, just maybe, one day get to experience a fleeting, but deeply meaningful moment of glory.

“The price of success is hard work, dedication to the job at hand, and the determination that whether we win or lose, we have applied the best of ourselves to the task at hand.” – Vince Lombardi, head coach of the Green Bay Packers (1959-1967).

By the way, I’m interested in your thoughts. Do you think that entrepreneurship is for everyone? As entrepreneurs, which personal traits and habits do we need to change to reach our goals, and experience fulfillment along the way?

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