How to Nail Your First Meeting With a Potential Investor
By: Michael Cardamone
Tags: Startup, Investors, Fundraising, Meetings

If I had to quantify the number of first meetings I’ve had with founders, it’d easily fall into the thousands. From video chats and calls with founders around the world, to in-person meetings in all three of our North American locations, I’ve seen quite a bit of it. Amidst those thousands of firsts, only a small portion make it through to a second and we’ve backed just a fraction of those. The buck doesn’t stop there. I’ve worked side-by-side with founders as they prepare for countless firsts with everyone from top tier investment funds to corporate purchasers and Angel investors. You could argue, I and the Acceleprise team have played a part in the production of what’s likely tens of thousands of first meetings. It’s a tough process, where presentation can often mean just as much as the contents of the pitch itself.

Getting the a first meeting is just the first step. Nailing the first meeting is what makes all the difference. You might have 30 minutes on the calendar, but your opportunity to build momentum and trust started when your request for an intro was forwarded.

This post is our digest of what we’ve learned from all of those data points. Here’s what we’ve learned.

Build trust quickly

At any investing stage, writing a check is an act of trust. Due diligence is a tool used by investors to increase their trust interval, but how you communicate is both the foundation and catalyst of trust.

Building trust through communication does two things for you as a founder:

It shows that you are approaching this relationship with the seriousness and honesty required to do business in good faith. It makes it easier to check issues with you instead of letting them fester. If an investor believes they can trust you, they will come to you quickly and often to assuage their concerns. If you don’t build trust, investors will instead rely on their own assumptions or fact checking.

Since you want investors communicating with you and checking their questions or concerns (not making assumptions), here are some tactics that will help you communicate in a way that builds trust.

Be consistent in how you communicate. An investor may email, text, or call, and having different styles for each is fine, but keep your tone and style consistent across the board. This includes things like:

The words you use

How you greet / sign off

Tone you use

Next, ensure consistency in the frequency of communication. This means your very first communications will set a precedent. If you’re known for lightning fast responses, then suddenly taking a day or two may give the investor cause for concern. On the flip side, consistent frequency should also be reasonable — you can’t take a week to respond to an email simply because that’s an expectation you want to set. A good rule of thumb is that all emails should be acknowledged within the same business day. Answer them if they are quick or acknowledge receipt and necessary actions for bigger asks.

This advice may fly in the face of what you’ve heard before about investor meetings, but we advocate complete transparency. Investors know startups are not perfect. They aren’t looking for perfection (not the good ones, anyway). Instead, investors are looking for people they can trust. If you’re hiding things and investors find out, that brings up two major red flags:

It signals to the investor that you’re either hiding from problems or trying to make yourself look better at the expense of your company. It begs the question: what else is being hidden that I haven’t yet found out about?

Being completely transparent also means you must be thorough in responses and do what you say you will. These two things alone provide a solid foundation of trust that, when lacking, cannot be earned in alternative ways. If you’re not doing what you say you will, investors may be scared off of the deal based on the assumption that you aren’t executing. And when you’re not thorough in responses to an investor, they will become concerned that you aren’t learning fast enough or not showing the vulnerability required to make the most of their money.

Finally, be polite to everyone. There’s never an excuse to be rude. And when we say everyone, we mean it. There’s a misconception that VC partners hold all the power and everyone else is an underling. The reality is that most investor partners will actively check how you treat their colleagues. If you get to the diligence stage, chances are an investor may want to talk to employees or customers as well. That’s not to say you can’t be tough, direct, or assertive. In fact, investors want to see that — but you don’t need to be rude to accomplish it.

Before the meeting

Heading into a meeting, you only need to send one email to do two things:

Send the deck ahead of time Confirm your meeting and share a win

1 — Send the deck ahead of time

Where a lot of advice suggests not sending the deck to avoid getting cancelled on, our advice is to send the deck to avoid the trap of a deck-read meeting. One of the fastest ways to kill investor interest is to ask them to enter a meeting totally blind and then spend the first 20 minutes going through your deck. Not only is the person caught unawares about the work your company does, they also are left trying to piece together how they ended up in that meeting — who made the introduction? Why did I initially say yes? Etc.

Sending the deck 2–3 days ahead of time (but no more) will give the investor time to read through, do some preliminary research, and come prepared with deeper questions. This is also the time you should confirm your meeting (see #2, below)

If they come into the meeting without reading the deck, that’s a sign that you’re facing an uphill battle with that particular investor. It doesn’t mean you can’t still secure the deal, but you should reset your expectations and buckle down.

2 — Confirm your meeting and share a win

Continuing the theme of being polite to everyone, confirm your meeting a two to three days beforehand, including your deck as an attachment, via email. When you do that, add in a very recent win if you have it.

Some examples of wins to share:

Landing a new customer

A new key hire

Impressive pipeline additions

A really good interaction with a customer that generated a referral or positive feedback

The goal is to create momentum leading up to the meeting. While there was obviously some interest (or they wouldn’t have agreed to the meeting), sharing a win so close to your conversation date will help get them to ‘lean in’ before the meeting even starts.

During the meeting

The meeting is your time to shine. You have about 5 minutes to capture an investors attention to keep them engaged for the remaining 25–40 minutes, so here’s how to make the most of your time.

Lead with your strongest card

In keeping with the principle of transparency, don’t hide your biggest win. If you secured a major enterprise client or poached a top executive, lead with that big win right after the intros. It is more likely to pique a VC’s attention and get them interested in the rest of the conversation.

Don’t have a major win yet? Speak to the size of the opportunity or strength of the team. Every company needs a strong suit to get them over the initial hurdles — lead with yours.

Explain the path

With clarity and conviction, explain how the market is evolving, what it looks like in 5 years and why your company will win in this evolving market. You want the investor to walk about from the meeting feeling like it’s inevitable that this is or will be a massive opportunity and then have confidence that you are the team to execute on it. If the market is expanding, where is it heading and how can you capture it? If the market isn’t expanding, what else has changed that means incumbent market share is easily up for grabs?

Have clarity on who you’re building for

It’s absolutely critical to know who you’re building for. This will identify the market, your marketing strategy, and guide your customer research. It will also heavily inform product development and could even lead to a strategic pivot into a new product or major new features.

As April Dunford talks about in her book on product positioning, you have to know your customers’ true alternative, which sometimes is a very manual process or simply dealing with the pain. If you don’t know as much as possible about your customer, you can’t build for them.

Know why your team will win

Chances are someone else is also thinking about the same problem or working to provide solutions to the same customer base as you. A VC with experience in your space is likely to have even met a few of those other entrepreneurs as well, making them zero-sum competition for VC dollars since most investors won’t invest in competitive products.

To combat this, you need to know your team’s secret weapon — the thing that sets you apart such as a key executive, hard-to-acquire knowledge, or a unique distribution channel. Having the right team — a secret weapon combined with the necessary expertise to execute — is another way that VCs increase their trust interval in a potential investment. Play this card wisely and always make sure it’s one of the strongest, if not the strongest, card in your hand.

Take notes and ask questions

The first meeting is a mutual assessment. You are fundraising and an investor’s job is to deploy capital. You need to know if they will be a good capital partner for your business, so don’t be afraid to ask about their timelines, process, and what they like to see in companies they invest in. Make sure you leave the meeting with a clear understanding of next steps in the process and the timeline of those next steps.

Asking questions (then noting the responses) will also help you with follow up later on, which can help secure the next meeting. In particular, make sure you take notes on what questions they asked and what risks they seem to be most worried about. After the meeting, write out the answers to those questions and get feedback on them from advisors and mentors, so you make sure to mitigate those risks in future meetings.

Own the narrative

A problem or challenge in your business is a chance to own your narrative and impress a potential investor.

Let’s say you’ve just lost a major enterprise client. At nearly any stage, losing a massive client is a bad thing. Instead of being worried that it will kill your investor deal when the investor finds out during diligence, get ahead of it.

Disclose the loss (again, transparency), but frame it this way: This loss happened. We did a post mortem that suggested the main cause of the loss was ABC. We believe XYZ systems were the root cause of ABC issue. We’re implementing DEF process to fix XYZ, which we believe will get rid of ABC issue, so we won’t have any more of this loss. Further, we’re trying QRS strategy to win back the client, showing them how we’re eliminating the issue that caused them to churn.

Extrapolating that out to a step-by-step:

Disclose the loss Explain the causes of the loss based on your post mortem Describe what you’re doing to mitigate or eliminate the causes of the loss so it won’t happen again Add in if you’re able to take any action to re-acquire the loss or make back the loss in another way

Have confidence and vulnerability

These two words — confidence and vulnerability — are often thrown around and have become buzzwords. Here’s what we mean by them:

Confidence is the knowledge that you have a legitimate opportunity to win. It’s a bold statement that you’re the one to take the gold.

Vulnerability is the source of your confidence. It’s the data you’re citing, the experience you’re bringing up, or the lessons learned from mistakes that make you believe you have it right this time. It’s also the part of you that is aware of the gaps in your own confidence and is open to taking in more data to fill those gaps.

After the meeting

Remember: the point of the first meeting is to get the second. Very few, if any, investment deals get done after only one meeting. If you met with a non-partner, in most cases they will have to develop a brief or investment memo to sell the partners of the fund on the investment. If you met with a partner, they will still need to sell the deal to their colleagues.

In this case, the best thing you can do is arm the person you met with any knowledge they need to make a case on your behalf. An investor developing a brief will need to show:

Why your space is exciting

What you’re doing in the space

Why they believe you can win

What risks or obstacles you’re facing — and how you will overcome them

The overall opportunity

This is where asking questions and taking notes during the meeting will come in handy.

Make sure to follow up on all questions and concerns they brought up. If they had a question, they will need an answer before submitting a brief. If you don’t send anything, they will do some quick googling and attach whatever they find. Chances are that won’t put your company in the best light, since you’re likely making a bet based on knowledge that not everyone has easy access to. Instead, send a thorough follow up with any relevant data points or stories so they can use the data you provided in their brief.

Further, send them a human-readable summary of your company. Chances are the other partners don’t have time — or won’t — read multiple pages up front. If you can provide an easy-to-read summary with key points, you make the investor’s work on your behalf a lot easier and more impactful for you. It’s yet another chance to own your narrative.

If the investor follows up asking for access to your data room, it may be a good idea to ask them what specifics they are looking for and share those documents manually. This will give you some more insight into what they are looking for. This is also stage-dependent and tends to work better the earlier the round is.

Investment is a process, but it can go very quickly

This guide offers you the tips necessary to nail your first investor meeting, but realize you’re still battling a miniscule conversion rate from meeting to funding. Not everything will work out, even if you did an amazing job in the meeting. Across all the rounds we have seen, first time founders on average need about 40 first meetings to get to a term sheet.

One way to tell if the deal has potential, though, is the speed with which investors move after the first meeting. Since investors are in the business of deploying capital, if they feel that your investment is worth making then they will move very quickly. As a rule of thumb, if you have an investor communicating with you almost daily to follow up, book next meetings, or ask for more information, that’s a great sign. The process itself still may take a few weeks since people’s schedules can be hard to pin down, the speed and frequency of communication after your first meeting is a good barometer of investor interest.

If the investor is dragging their feet, there may be something else at play. For example, they may be running it by other people in their network who know the market better than they do, or they may be running it by a portfolio company who could be a customer. But if you’re facing an investor moving slowly, keep going with your fundraising process, continue following up for their next steps and time frame, and continue to engage with positive updates as they happen.

Still not getting much from an investor after a few friendly follow ups? Move on. If you have a regular (monthly) newsletter for investors to keep them up to date about progress, ask the investor if you can put them on it to stay in touch. Otherwise, continue to be polite — you never know when you’ll run into them again and it will be the right time to talk.