How to Attract Investors: 10 Tips for Investor Meetings

Written by Dave Bailey

Filed under board fundraising scale-up

Chris Sacca, investor

The first step in securing investment is making a good impression. Learn how to charm investors without losing credibility.

I’ve given many hundreds of pitches as an entrepreneur, but it’s only since I’ve become an investor that I’ve actually felt what it’s like to receive a pitch. And it’s actually pretty tough to evaluate a business in under an hour.

Often, the hardest part isn’t the complexity of the business — it’s extracting the information you need from the founders’ heads. Looking back, I must have sometimes been a challenge for investors to deal with. So, here’s the advice I wish an investor had given me when I started. 

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1) Make the deck beautiful

It pays to get your pitch deck professionally designed. Use images to ‘show’ rather than ‘tell’ and look after the styling, fonts and alignment. Recently, I received a pitch deck so beautiful that I met with the founders even though I didn’t understand what they were trying to do. The design just signalled ‘high-potential’.

2) Drop-in your research

Failing to research your target is a rookie mistake. I have LinkedIn and Twitter profiles, a Medium account, and a company website detailing all of our investments. If you congratulate me on a recent deal, I’m going to be impressed. One founder quoted one of my articles in the conversation and, as shallow as it sounds, I can’t help but like this guy. Flattery will get you everywhere.

3) Own the agenda

Good investors allow the entrepreneur to lead the pitch. Sadly, this gives you enough rope to hang yourself. Start the meeting by outlining a clear agenda, and by effectively managing the schedule; you’ll come across as extremely professional. Conversely, diving straight in and running over the scheduled time adds extra stress neither side needs.

4) Get me to relate

Before even mentioning your solution, lead with a relatable story about how people struggle without your product today. In a pitch I recently heard, the founders led with a description of their product and launched straight into its features and distribution channels. But without a story to help visualise their customers, the information had nothing to stick to and I couldn’t help zoning out.

5) Check-in with me

The word pitch implies that information flows in a single direction, but the truth is that no-one likes to be talked at. Don’t forget that you can only communicate as fast as your audience can take in the information. You’d be surprised at how many times I signal that I’m confused, but the founder doesn’t even notice. Remember to check in regularly and address any questions.

6) Embrace silence

Once the business summary is over, I’ll have some quick questions to fill the gaps in my knowledge. Don’t be afraid to answer a question like, ‘How many people are on the team?’ with a simple, ‘Four’. Silence gives me time to process. Filling up that silence with stories is unnecessary and makes it hard for me to process the information — and move on to the ‘good stuff’.

7) Ask for my advice

‘Ask for investment,’ it’s said, ‘and get advice. Ask for advice and get investment.’

You have everything to gain from asking me for advice in an area you know you need it. As well as making you look smart and mature, it puts me on the spot and makes me want to show you how I can add value.

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8) Humour me

When receiving advice, curiosity wins and defensiveness loses. Whether you agree with the advice or not, the smart move is to ask questions like, ‘Have you seen something like this before? I’d love to hear about a specific case.’ To end, you could say, ‘That’s a great idea — we’ve thought about this, but not enough,’ and jot it down in your notebook.

9) Say when you don’t know

Let’s imagine that you haven’t figured out a business model. Don’t do what I did when I was a founder, and present three possibilities, hoping that one of them is right. Instead, present it as something you are actively testing. ‘We’re still working through three potential business models. This is an area where we could use your input.’ This shows you know the value of focus and good advice speaks volumes.

10) Follow up immediately

Follow up immediately after the meeting with a short email. Include your one or two key takeaways and some bullets on next steps. Keep it very short: 35 words maximum. If you help me stay organized even before I do, I’m going to love you for it. That’s why you need to be quick — or I’ll do it to you and gain the upper hand!

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Investors are just people

It’s easy to think that investors are cyborgs and there’s nothing under their skin but circuits and spreadsheets. But we are humans too. Maya Angelou said it best when she said this:

At the end of the day people won’t remember what you said or did, they will remember how you made them feel.”

Continue reading about attracting investors: 

Originally published Mar 13, 2019, last updated Jul 26, 2023

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