My 3 favorite questions to ask before starting a business

Jonathan Mills Patrick
3 min readDec 31, 2020

Three questions, really? Is that all the questions to ask before starting a business. Well, no. There are a ton of questions to ask before starting a business. However, out of all of those questions there are three that I like people to start with. I have used these same three questions personally. I also use these questions when I am coaching an entrepreneur or when people are looking to join my team.

The reason I like these questions the best, out of all the possible questions a person should consider, is that they help get to the root of your expectations about starting a business. Because the reality is that entrepreneurship isn’t for everyone. It can be brutal. More often than not. When you ask yourself these questions and you answer them directly and honestly you help remove any assumptions you are making. Particularly about the level of success you are expecting and how much work you are willing to put into the business.

The first of two questions to ask before starting a business focus on the amount of effort you are willing to put in.

Question number one is — How many hours per week are you willing and able to put into your business?

I’ve seen people have successful businesses that were only able to put in a few hours per week into their business. But the reality is that the more time you have to offer the better your chances of success. Don’t worry if you only have a few hours a week. You can still be successful. It just means that you are going to have to be very diligent about where you spend your time. The key is that I don’t want you to believe that you can have a successful business without being willing to sacrifice some of your time. There is a big difference between not having the time to work on your business and not being willing to put in the time. You just have to decide what other activities in your life you are willing to put aside in exchange for working on your business. Which leads us to question number two.

Question number two is — How many months are you willing to work on your business before you expect to make any money?

Now we are really getting to the heart of the matter. It is one thing to only have a few hours per week to put into your business. It is an entirely different issue to only have a few hours per week and expect to make money in your first month or even months. Are there entrepreneurs who have made money right away? Sure. Is it normal? No. Especially for some business models that take more time to establish. I always like to hear that entrepreneurs are willing to put in six to twelve months of effort before they even bother looking in the rearview mirror to see their results. Not only does that show dedication, but it also shows that they have realistic expectations.

Our final question is — how much money do you expect to make?

Talk about setting expectations. This particular question is where I lose most entrepreneurs. When given the option of whether they want to make a living or be a millionaire most of the people that apply for my mentorship program choose the latter option. You would think that is what I am looking for. Because it shows that they have real ambition. But that isn’t necessarily the case. Few people become entrepreneurs with a goal of making $5,000, $10,000, $25,000, etc. However, based on my research for my book, “The Ladder or The Grind”, most entrepreneurs are lucky to make a living. Let alone millions of dollars. Should you be ambitious and shoot for the stars? Absolutely. My concern with being overly ambitious is that people tend to quit when things get hard and they aren’t already filthy rich. Go for millions but be grateful if your business produces a secondary income for you. You will be surprised the difference a few extra thousand dollars per years can make.

P.S. Because I enjoy working with young entrepreneurs, and new entrepreneurs, I’ve decided to provide a free mentorship program where I work with one startup every quarter of the year.

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Jonathan Mills Patrick

I’m a former C-level banking exec. and 3x startup founder leading a corporate innovation/product team and have helped companies raise over $800M in funding.