11 Questions Founders Need to Ask Investors During the First Meeting

Last week we wrote about questions that investors ask founders during investor meetings. This week we are turning the tables and talking about questions that founders need to ask investors.

Most founders spend little time asking investors questions, and that’s too bad. First of all, good investors love it when you ask them questions, because it shows that you are thoughtful and don’t think of them as just a walking wallet.

Secondly, by asking the right questions you can avoid happy ears, avoid a MAYBE, and really qualify investors in your funnel. By asking questions and getting clear answers you minimize the chance of wasting your time with investors who will not invest.

1. Are you interested in potentially investing in my company, and if so, what are the next steps?

No first meeting should end without you asking this question. Be direct. Do not be shy. Whether you are meeting an angel investor or a VC, ask this question before you end the meeting. Every investor, by the end of the meeting, will make up his/her mind.

They will not decide to invest, that almost never happens, or happens very rarely. Most likely though, the investor will decide to pass, because most investors pass on most companies. And some investors will want to continue the conversation.

By asking this simple and direct question, you will know exactly where you stand. If the investor indicates interest in continuing the conversation, then ask about the next steps. Listen carefully to what the investor is saying.

For example, if the investor says “keep me posted,” or “I am traveling for the next few weeks,” or “I have a lot of things I am working on”—this is known as a soft NO or definitely not now. When an investor is vague, assume he / she is not interested.

On the other hand, if the investor proposes to set up a follow-up meeting or a call quickly—in the next week or so, this means there is interest. Listen carefully to what the next steps are and decide if the interest is real.

2. What is your investment process, and how long does it take?

If the investor is interested in taking the next steps, you need to ask about the whole investment process. The process will vary widely depending on the type of investor.

Let’s start with an individual angel investor. Most likely the process will be 2-3 meetings and some diligence and reference calls. It is pretty light, and depending on the check size and where you are in your round, it is totally fine to ask the investor to commit at the end of the second meeting.

Some angels like to co-invest with others and that often prolongs the process. If others are involved this means more pitching and more coordination between the group or a syndicate. Ask how long will this take, what will the total check size be, and actively manage this process. Often times co-investors will drag the process out, and the initial angel may change her mind about investing.

Similarly, angel groups have a clear process that is typically not fast and involves multiple meetings and diligence calls. Typically, a formal angel group will assign a team of angels to an investment committee for each deal. You will need to meet with them at least few times and then, if things go well, present to the entire angel group. After that, there may be more diligence.

The process for Micro VC and VC firms varies, but in general takes 3-4 meetings to arrive at a positive decision. Every firm meets regularly to evaluate the deal flow. When you hear that you will be talked about during the partner meeting this week, this is generally a positive thing but be ready for a quick NO coming out of that meeting.

If the VC is engaged you should be meeting with more and more partners in the firm as the process unfolds. For larger checks you will be invited to present at a partner meeting. That would be a critical meeting for a YES decision. If a firm has a seed program and writes smaller checks, then you might be able to get a positive answer without presenting to the entire partnership. Read 8 Things You Need to Know about Raising Venture Capital for more details about raising from VC.

3. What is your check size?

Another important question to ask is the check size because you want to know your result in case you are successful. Knowing the check size helps influence the timeline, and frankly, the effort you put into this particular pitch. For example, if you are raising a million-dollar round, you can’t spend a ton of time with people who write $25K checks. You simply won’t be able to get to the finish line if you focus on those.

What you are looking for is to start your round with smaller checks but quickly move to bigger ones as you have more and more committed. For a million-dollar round for example, you want to spend most of your time on $50K or $100K and hopefully get one check for $250K or more.

Oftentimes you will hear a range. An angel can invest $25K-$200K, or a VC can invest anywhere from $300K to $5MM. Ranges in general aren’t great because they lack clarity. There maybe complexity or another message behind them. For example, an angel who commits to $25K-$200K may only invest $25K personally and then syndicate out the rest. The syndicate may or may not come through though, so you can’t count on that money.

Similarly, when a VC names a range, it might actually mean that they fund seed rounds exceptionally rarely. If you dig in you will find out that the only $500K check this particular VC wrote was for a serial founder they knew personally and that their minimum is really $2MM for other investments. This is important to understand because if you are only raising $1MM, then they aren’t the right investor for you right now.

Another thing to keep in mind is ownership targets. This is particularly true for larger VC funds and also for some micro VCs who write larger checks. In addition to check size, you may want to ask if you are aiming to own certain % of the business.

4. How many more investments are you planning to make this year?

Surprisingly for founders, not all investors may be actively investing. Even more surprisingly, they may still take meetings to learn more about your company. Angel investors may be out of cash and tell you they aren’t liquid. Or they could plan for, say six investments per year and have already done five. In that case they would be much harder to get the check from.

The number of investments per year is called pacing, and disciplined investors pay a lot of attention to it because they want to be investing continuously through the year. For example, if a VC has a seed program, and they fund ten deals per year but have already funded all ten, there are no more checks left. With this information, founders should reduce the chance of being funded by this firm to basically zero.

Another, much more subtle issue with VC would be capacity. Some partners just don’t have the bandwidth to take on any more investments. In that case, they would still meet with the founders, but they just can’t invest. Asking about ability to invest upfront saves a lot of time.

5. Who else needs to be involved to make the decision to invest?

The ABC of sales is to find a champion and to find out who can cut the check. Similarly with fundraising, when you are dealing with angel groups and venture firms it is important to understand who will be involved in making the decision.

Some angels tell you that they co-invest with friends. This can be both a good thing or a bad thing. The good is that there may be more capital available if you succeed, the bad is that the decision is distributed. Be sure to meet everyone who is involved in making a decision; don’t let other people present the business on your behalf.

Similar to VC firms, understanding the decision-making process is important. In most VC firms, associates will not be able to make a decision without involving a partner. Which partner is making a decision? Can you meet them? Again, making sure that you meet with the decision maker is critical on the path to getting a YES. Another way to think about this is that if you don’t meet the partner, it is basically a NO.

6. What is the last company backed, and why?

This is a simple but relevant question. You are testing for how quickly the answer comes, how enthusiastic the investor is, and when the investment was made.

It can be quite telling one way or another. Has it been a really long time since the last investment? If so, what does it mean? Is it that this particular investor has set a high bar or is it that they don’t have capital left to invest this year? Ask about the number of planned investments and you will have the answer.

You also want to hear the WHY. What made the investor write the check? Was it an amazing founder, vision, market, or something else entirely? Listen carefully to the answer, as it should be helpful to figure out what the investor will look for in your startup.

7. Have you invested in a competitor, or are you considering doing so?

You should ask this question 100% of the time, because unfortunately, some investors will not tell you this unless you ask.

If an investor has already invested in a competitor, even if it is not a super close competitor, the chance of you getting a check from them is close to zero. It really is zero. VCs don’t invest in competitors, and angels avoid doing it too. The reason is that it is hard to help both companies, since they are competing. It is essentially a conflict of interest.

An investor simply evaluating or considering investing in a competitor is much more subtle. It is typical that when a venture firm is planning to make an investment in the space they do a lot of digging and research. Part of the research they engage in is reaching out to all competitors in an attempt to gather more information. In this case, the VC is trying to do his best to pick the best company in the space.

You may get a call from an associate of a firm saying that the firm is interested in the space and wants to talk. You will be asked a lot of questions and at times even move through the process, only to find out in the end that it was a so-called “brain suck.”

This may seem very unfair to the founders, but it is the reality of what’s happening in the market. To avoid wasting time and getting hurt, ask about competitive investments or research upfront.

8. What are your concerns about our business?

This is a great question that Steve Schlafman from RRE ventures suggested founders ask.

Why wouldn’t you invest in my company? How do you see the risk here? What do you think won’t work / I am doing wrong?

By asking this question directly, you are accomplishing several things. First, you are signaling that you are open to feedback and value it. Secondly, you are indicating that you respect the opinion of this investor.

More importantly, you are likely getting valuable information from the perspective of an investor who sees hundreds of companies each month.

The concerns will range from market size, to acquisition channels, to competition and pricing. Having this information can help you work through the concerns and address them during the investment process.

9. What is your follow-on strategy?

Some investors follow on and put more money into the companies, and some don’t. Both strategies are perfectly fine, but it pays off to know which is which.

Specifically, if you are raising money from angels, and most of your backers do not follow on, this means that you may have a hard time raising your second seed round. Most companies need more capital before they get to series A, and most of this capital comes from insiders—investors who have already invested. If most of your insiders don’t follow on, you will need to go outside to raise more capital. This can be tricky, especially when you are post-seed but before series A.

With VC firms, the dynamic is different. Some VC firms deploy smaller amounts of capital at seed stage with the idea of leading series A. The follow-on strategy is to lead series A. However, there is a potential issue that founders need to be aware of; IF the firm decides not to lead series A, there maybe a signaling issue to the rest of the market. It pays off to connect with other founders that the firm backed to get the color on this dynamic.

10. How do you help companies you back?

Many investors talk about being a value add in addition to money. Ask how exactly this particular investor will help, and ask for specific examples involving companies the investor backed.

Some investors come with a massive network. Some larger VC firms will help you recruit and scale. Some smaller angels are great at pricing and financial modeling. Some investors really understand distribution.

Whatever it is, investor like being asked this question and it is helpful for the founders to know.

11. Who are some of the founders you backed that I can talk to?

Much like investors reference check founders, the founders should reference check investors. Ask for 2-3 founders that this investor has worked with.

You don’t necessarily need to connect with them after your firm’s meeting with the investor, but it is a good question to ask and see what the answer is.

Great investors will have raving references from the founders they supported and less than great investors will be reluctant to name names.

And now we want to hear from you. Founders, please tell us what questions you asked investors during the first meeting that you found helpful.



Fundraising Startup Advice Venture Capital

Alex Iskold View All →

Engineer, Immigrant. Vegan. 3x Founder, Managing Partner @2048vc. Previously ran @techstars in NYC. I write #startuphacks: http://alexiskold.net .

8 Comments Leave a comment

  1. Re the question ‘What is your check size?’ (item 3), it’s important to understand that VCs like to invest when it’s time to add fuel to the fire – i.e. when their money will be used for growing the business, rather than for building the initial product and proving the business concept.

    Therefore, there’s usually no point in pitching VCs if you don’t have clear evidence that you’ve reached product-market fit (i.e. there’s a real fire). They’d usually also want to see clear metrics on the customers’ acquisition cost and life-time value. This helps them validate that the business can scale economically, and thus it makes sense to add fuel to the fire.

    Liked by 1 person

  2. For some of the questions such as *Have you invested in a competitor? OR, What was the last company you backed?, OR even “What is your investment process?”…. is that not typically a part of founders’ homework before they meet an investor?

    So for example, I would rather put my question as “I see that you backed ABCD which is one of our competitor (or they operate in the similar space). So what made you invest in them?”.

    It just shows that founders have done their homework for the meeting. Correct me if I am wrong.

    Liked by 1 person

  3. This is very useful! I have only really had one investor meeting and with only 15 minutes I didn’t plan my time well enough to include these questions! next time


    • I’m not sure why you had only 15 minutes, but as a general tip, I’d avoid one-on-one meetings with investors that are planned in advance for only 15 minutes. A typical meeting with investors is planned for 45-60 minutes. So if someone is only willing to invest 15 minutes of his time in hearing about your company, it’s a signal that he’s not really interested.