13 of the Smartest Questions Investors Ask Entrepreneurs

Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched BusinessCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

What is the smartest question an investor has ever asked you?

1. What’s the Biggest Threat to Your Success?

Andrew ThomasThis question forces you to demonstrate your ability to realistically evaluate your market potential and the maturity to acknowledge that threats exists. The investor is also testing your composure — as this question can cause defensiveness. If asked, take a deep breath and be honest about your threats and how you will address them. This builds confidence and trust instead of a red flag.

– Andrew ThomasSkyBell Video Doorbell

2. What Happens if You Get Hit by a Bus?

John RoodOf course the founder is critical to the enterprise, but especially for small businesses, I’ve found that smart investors want to make sure you have a clear pathway to generating enterprise value that isn’t just you personally working 80 hours for the rest of your life. Luckily, this can help you prioritize delegation, which you should be thinking about anyway.

– John RoodNext Step Test Preparation

3. Why Is This Opportunity Any Different Than Going to Vegas and Throwing It All on Red?

Jonathan LongI’m currently consulting for a new app and they have one investor who is funding the entire program. He jokingly asked me, “Why is this opportunity any different than going to Vegas and throwing it all on red?” While it was more of a joke, it was a legitimate question. You need to be able to sell and defend your concept. If you can’t, why should an investor feel comfortable writing a check?

– Jonathan LongMarket Domination Media

4. What Happens if Facebook Goes Out of Business?

Piyush JainWe were starting out an app idea completely based on Facebook. Investors asked what happens if they go out of business. We went blank. We ended up reshaping the model, though, so it would not be fully dependent on Facebook, and it ended up being a better app. Sometimes we tend to over-rely on big systems which can be more susceptible to failures than we are.

– Piyush JainSIMpalm

5. Why You?

Blair ThomasHaving to answer that very simple question can often stymie even the best stakeholders. Are you different? What do you have to offer that your competitors do not? Why am I investing in you when there are 12 other companies competing for my dollar? It can be a difficult question to answer, and one that you should have an answer for. Be prepared to argue your case as a differentiator.

– Blair ThomasEMerchantBroker

6. Why Now?

Charlie GrahamGreat market timing — more than even team or idea — has traditionally been the best predictor of a company‘s success. Chances are someone else has tried an idea similar to the one you are pitching. What fundamental change has occurred in the market that makes right now (versus 3-6 months ago) the best time to start this company?

– Charlie GrahamShop It To Me, Inc.

7. How Can I Help?

Zoe BarryThis question is a litmus test. Keep in mind not all money is equal shades of green. I’ve found the best investors want to know what my challenges are and where they can add value. Once an investor puts money into your company, their role is to help the management team build a great business. If an investor doesn’t ask you how they can help, don’t take their money.

– Zoe BarryZappRx

8. Why Can’t You Just Bootstrap This Business?

Ross ResnickUntil an investor asked me this question, I was convinced that outside investment was the only way to start a company. Answering his question forced me to analyze my initial product development road map and reimagine it to be immediately cash flow positive and self-sufficiently scalable. This fundamental shift enabled rapid, responsible growth.

– Ross ResnickRoaming Hunger

9. Who Is This For?

Vik PatelWe often develop business ideas by looking at successful models and applying them to a different domain — the Uber-for-X approach. It’s easy to miss the most important point: Who is this for? Being asked that forced me to think concretely about the people for whom I would be solving a problem and make the appropriate changes to the execution of business ideas.

– Vik PatelFuture Hosting

10. What Excites You?

Ty MorseAn investor asked me this to find out what motivated me, and I think that’s what investors need to know. Are you going to pursue this idea until it succeeds? Do you have the drive, the energy, the passion to make this work? This question gets to the core of who you are and lets investors learn a little about who they’re investing in.

– Ty MorseSongwhale

11. How Long Do You Think the Money Will Last?

Vishal ShahThis question forces you to demonstrate your understanding of the revenue streams, cost structure, cash burn and runway. VCs want to know how you plan to spend the money and if what your ask is realistic enough to get you to your next milestone. If you seek to raise too little or expect an unrealistic runway, it indicates that you haven’t thought through how you will scale your business well enough.

– Vishal ShahNoPaperForms

12. Does Your Business Align With Your Experience?

Erik SeveringhausLon Chow asked me why my experience didn’t match the market I was entering, as I left a successful career at IBM to start a B2Ccompany. There’s a lot written about product-market fit, but not enough on founder-market fit. Does the founder truly understand nuances of the industry? What makes it tick? Lon zeroed in on the misalignment in our first meeting and I realized just how right he was.

– Erik SeveringhausSimple Relevance

13. Why Are Other Investors Passing?

Fan BiDon’t take it as a passive-aggressive question and get defensive. You should have a good answer. The best answer you can hope to provide is that they didn’t believe in the market or where it’s going. Different investors have different theses on macro trends and will understand other investors not believing in yours.

– Fan BiBlank Label

Get the Latest Interviews and Insights


About YEC
YEC
Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, YEC recently launched BusinessCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.
View all posts by YEC
  • Michael Rincker

    #2 and #13 would be tricky.