A Q&A on investor Q&As with pitch coach Nathan Gold

Pitching to investors or an audience is slightly terrifying for just about any entrepreneur. But if you want to enter the game as co-founder of a company, it’s assuredly part of the deal. To keep the bullets of sweat at a minimum, preparation is essential. Fortunately, we got in touch with pitch coach and professional…

Pitching to investors or an audience is slightly terrifying for just about any entrepreneur. But if you want to enter the game as co-founder of a company, it’s assuredly part of the deal. To keep the bullets of sweat at a minimum, preparation is essential.

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Fortunately, we got in touch with pitch coach and professional speaker Nathan Gold, who recently spoke during Global Entrepreneurship Week about all the ways to prep wisely. We corresponded via email to try and absorb as much advice as possible and thankfully, he went above and beyond. Read up and rest easy knowing you won’t need a towel at your next pitch:

What are some keys to answering questions more effectively?

Be prepared. Spend time rehearsing your answers just as you rehearse for your presentation or investor pitch to give you more confidence.

Build a bridge. When you do not know the answer to a question and you need to say, “I do not know” or something like “I am not sure how to answer that without talking to my CFO,” you can use a bridge to something else that adds to the presentation. When you can say something like, “Well, I don’t know. However, what I would like to emphasize is…,” you will be controlling the flow of the conversation and covering information you feel is important at that moment.

Learn to pause. I am talking about pausing for a second or two before answering to show the audience you are being thoughtful, concerned and respectful. A momentary pause before answering a question will build more anticipation and curiosity. So, unless the question is dead simple such as, “How long have you been in business?” be sure to add a pause and you will see a difference in how people react.

No “but.” When you respond to someone by saying, “Yes, but…” or “No, but…” you are in essence negating everything the person just said. This is how we battle in our communications and one reason people have no patience to hear your side. By replacing the that with “Yes, and…” you are telling the listener you agree, acknowledging their point and still allow room to add your point.

 

What’s an important technique entrepreneurs can practice before they reach the day of the presentation?

Prepare for as many questions as you can predict from your audience with the same emphasis and rehearsal as you do for your presentation or pitch. Record yourself answering the question and watch it immediately. By seeing and hearing yourself, you will know if you have a good enough answer.

 

What are some of some of the toughest questions investors dish out that entrepreneurs should run through beforehand?

This all depends on the type of investor you pitch. Angels and venture capital investors sometimes ask different questions, but there is certainly overlap. Here is a list of some of the toughest questions I have seen entrepreneurs be asked. In many cases, these questions can destroy a perfectly timed presentation because they are unpredictable!

  • What is the real problem you are solving?
  • How will you make money?
  • Who cares? Why should I or anyone else care?
  • If this is so great, why hasn’t this been done before?
  • This has been tried before and failed. Why is it going to work this time?
  • Why you and your team?
  • This sounds like a product in search of a problem, isn’t it?
  • What is your biggest differentiation?
  • How many customers have you validated your product/service with?
  • Come on. Move on already. Aren’t you stating the obvious?
  • What is your go-to-market strategy?
  • What are you replacing today with your solution?
  • What are the most important issues you see facing in the next three to six months?
  • Why should we invest in your company?
  • Isn’t this just a feature?
  • Haven’t we seen this before?
  • Why will people fall in love with your product or service?
  • How do you stack up against your competition?
  • What barriers have you put in place to stave off the competition?
  • How big is the market, really?
  • How big is your total addressable market?
  • Why is this technology defensible?
  • How do you compare to _________?
  • Who is desperate or dying for your solution?
  • Aren’t you leaving money on the table?
  • What are your real barriers to entry?
  • What are the top three risks you face in your business right now?
  • What is your exit or acquisition strategy?
  • How many companies have you raised money for?
  • How long do you see yourself remaining in the CEO role?
  • How did your investors make out in your last company?
  • How long before I capitalize on my investment?
  • What’s in it for me?

 

How should entrepreneurs respond if they don’t have a brilliant answer?

If an entrepreneur does not have a brilliant answer for a question, be honest! Do not lie or make up an answer on the spot because people will instinctively know what you are doing. Simply saying you do not know or that you will need some time to get a satisfactory answer is absolutely okay. However, do not stop there. Do not simply say, “I don’t know” and leave it at that. This is your opportunity to build a bridge to the information you think is important at that moment. Also, by not having the answer to a question, it makes you more human and not too perfect. It also gives you an immediate reason for follow up, which might be exactly what you need to keep the process moving in the direction you hope for.

 

What’s the best way to start and wrap up a presentation?

Some people are a fan of asking the audience a question or a set of questions to start a presentation. I am a fan of this approach only if those questions are not obvious ones where all the presenter is doing is getting the audience to raise their hands for the sake of raising their hands. So long as the question or questions are relevant and truly related to the presentation, feel free.

My favorite way to start a presentation is with a personal story related to the talk or something I personally experience through someone else. People relate and remember stories much more than bullet points on slides. The best presentations always begin with a captivating story that is relevant.

With entrepreneurs, the most effective way to start an investor pitch (and this is not a cultural thing as it works all over the world) is to tell the relevant parts of a story that illustrates the problem or unmet need they are solving. The story should not tell what they are doing to solve the pain or problem. It should simply convey to the listener the essence of the big problem so that the rest of the presentation can be used to show how you solve the problem.

To wrap up, my favorite technique is to use The Columbo Close. I invented this close because of my love for the detective in the Columbo TV series. He always cracked the case in the last few minutes of the hour-long show by saying, “By the way, one more thing…” That thing would prove who did it and the show would be another success for Detective Columbo!

Here’s how it worked for a company in Ireland that created a product that veterinarians can use to determine if a horse has an infection and how severe it is. They created a pregnancy-like tester, but for horses. A single drop of the horse’s blood placed on this disposable product can instantly determine if the horse has an infection along with the severity. It does not determine what the infection is. That needs to be done in the lab. But, in the field, the vet can determine whether there is an infection without taking the blood sample to a testing lab. They ended with something along these lines:

“In conclusion, I’d like to leave you with one final thought. As you leave here and drive down our country roads, you may notice a horse standing in the field. When you do, you will remember that today you have seen a technology that will forever change how veterinarians care for those horses right where they stand. Thank you!”

Finishing a talk or pitch with the Columbo Close will usually have a positive effect on your audience. Can you imagine the next time this audience sees a horse? What do you think they will think about at that moment? They may even remember you months or years from now because you tied your technology to something they will notice in their everyday lives.

Alternatively, you can always come back to the story you started with and finish with a part of it they have not heard or simply repeat the main point of that story.

Finally, I recommend you never end on a question and answer. What if that question generates conversation that is not so positive or it may be on a topic totally unrelated to the purpose of your pitch or presentation. Do you want people thinking about the last question when they leave your meeting?

I recommend finishing with the Columbo Close, one more short story or something else that wraps up the meeting, presentation or pitch so people are thinking about what you want them to think about rather than the last question asked.

This story is part of the AIM Archive

This story is part of the AIM Institute Archive on Silicon Prairie News. AIM gifted SPN to the Nebraska Journalism Trust in January 2023. Learn more about SPN’s origin »

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One response to “A Q&A on investor Q&As with pitch coach Nathan Gold”

  1. Matthew W. Marcus Avatar

    This is pure gold (pun intended). Nathan is not only a fantastic pitch/presentation coach, but he’s also one heckuva guy. Thanks for all that you do, Mr. Gold. Entrepreneurs are all the better for it. #muchasgracias

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