35+ Questions Entrepreneurs Must Be Able to Answer

1 C04YZ3Orj72fs1K ll0W4Q

I’ve been asking myself a lot of questions lately. And by lately, I mean at least since I was old enough to remember my internal monologue.

For those that don’t know me well, I’m an aspiring serial startup founder. I love the concept of startups. I’ve wanted to run a business since I was a tween. Between then and now, I got sidetracked by college, grad school, and working as a data scientist.

Throughout it all, I knew a startup was in my future. Then, not too long ago, an opportunity came about to join on as the founder of an industrial analytics startup.

Long story short, I found out that nearly everything I thought I knew about startups was wrong. And it all came down to asking the wrong entrepreneurial questions or assuming I knew answers that I didn’t. This was my first experience with a failed startup.

I asked the wrong questions of my co-founder when he proposed the idea. I asked the wrong questions of my friends and colleagues when I was deciding whether to take the plunge. I asked the wrong questions of myself to determine if I was ready. I asked the wrong questions of google when evaluating the market.

Most importantly, I asked the wrong question of potential clients when validating the idea.

Now don’t get me wrong. I don’t regret doing this. The list of mistakes I made may fill my nightmares for years to come, but I wouldn’t take it back for all the money that’s no longer in my bank account.

A nest egg can be rebuilt, and the experience that comes with trying and failing is worth every penny.

From that experience, I have created this list. These are both the questions I asked then and the questions I wish I had known to ask.

Be confident in your answers — so confident you would be willing to restate them to a room of investors. If you aren’t that confident, consider what that means for your venture.

If this list inspires some second thoughts, I’ll consider it a success. You might come out the other end even more certain of your cause and your abilities, and that is fine. Entrepreneurs need confidence, but it needs to be earned.

This list was created with high-growth startups in mind, but most of the questions are important for any business venture. I’m currently using them for my new writing venture, and they’ve already been a huge boon to me.

Without further ado, here’s the list.


5 Questions About Yourself

We’re going to start things off a bit on the personal side. Are you ready? Good, let’s get going.

  • Am I emotionally ready for this?
  • Am I financially ready for this?
  • Are my loved ones ready for this?
  • Do I have enough passion for this problem and this market?
  • Where do I see myself in 10 years?

11 Questions About Your Co-Founder(s)

The first 5 should look familiar. The rest of the questions are all about your relationship. Not to be cliche, but finding a co-founder is a lot like finding a spouse.

  • Are they emotionally ready for this?
  • Are they financially ready for this?
  • Are their loved ones ready for this?
  • Do they have enough passion for this problem and this market?
  • Where do they see themselves in 10 years?
  • Do I believe in and trust them?
  • Do they believe in and trust me?
  • What do they bring to the table that I don’t?
  • What gaps in my skills, network, or knowledge are they not filling?
  • Do we work well together as equals?
  • Do we agree on who the boss is?

11 Questions About the Problem and Market

This one might contain a couple of terms you aren’t familiar with (TAM/SAM/SOM). That’s fine. I didn’t know them before my first startup either. Be sure to look them up.

  • What problem am I trying to solve?
  • Who feels this pain the most?
  • What is our total addressable market (TAM)?
  • What is our serviceable available market (SAM)?
  • What is our serviceable obtainable market (SOM)
  • Is our SAM niche enough?
  • Is the TAM large enough?
  • How quickly is the market growing (or shrinking?)
  • Who are our competitors?
  • What makes those competitors better than us?
  • How will we acquire customers?

4 Questions About the Solution

Now you know the who and the why… but do you know the what?

  • What would a lean MVP look like?
  • What makes our solution unique?
  • How can we prove that to our first client?
  • How will we make money?

8 Questions About the Company

One last section. How are you doing? Great, let’s finish strong.

  • What does success look like?
  • What is our biggest risk?
  • What is our runway?
  • How soon until we need to start raising money?
  • Do we need to raise money or should we bootstrap?
  • What is our vision?
  • What should our company culture be like?
  • What business type (LLC, C-corp, etc) makes sense for us?

Final Thoughts

Do you feel more ready now? If you were able to answer all of these questions, you are probably more ready than I was for my first startup. This is going to be an exciting journey. I loved it, and I firmly believe that you will too. It will be stressful, but there is not a better experience on this planet.

This is not a definitive list. But it is an evolving list. No entrepreneur has perfected this process, and I harbor no delusions about being the first.

That is where you come in. Tell me what is missing. I’ll take those responses and include them in the list, with your permission and appropriate credit given of course.

Leave a Comment

Your email address will not be published.