Can you automate LinkedIn outreach to investors?

No. You cannot automate LinkedIn outreach to investors. Someone who invests in different companies can tell in a second whether a message was written by AI, so it has to be extremely authentic. You can systemise the research behind each message. You cannot automate the message itself.

On this call, a head of marketing at a hospitality group asked me exactly this. They knew automated LinkedIn workflows and DMs well, and had ethical doubts about using them for investors. I agreed with them straight away.

Why can't you automate messages to investors?

Think about who you are writing to. Someone who backs different companies, who is at that level of the ladder, can see in a second whether a message is AI or not. One glance. Once they see it, you're done.

There is another reason. There are only so many people who could invest in a business in a particular city and a particular industry. You can't reach out to a thousand. There are probably about 100 people you need to reach. Any one of them could change the trajectory of your future.

You're not signing a small marketing deal with a retailer. You're asking someone for a million dollars or a million euros. That deserves a message written for them alone.

What is the difference between sniper and machine gun marketing?

I look at LinkedIn marketing in two types. The first is sniper marketing. You have a selected group, say 100 individuals to reach over the next three months. You research each one. Then you write each message by hand, very specific to them, their situation or their portfolio of companies.

The second is machine gun marketing. When I want to connect with people who might want a website built in a particular industry, my first message is automated. It talks about their industry and their city. If they're interested, I get on a call with them straight away.

Yes, that outreach is machine made. But it's the same message I would write by hand anyway. The machine just sends it. That's where I draw my moral boundary. Investor outreach is never machine gun work. It's closer to guerrilla tactics.

How do you systemise the research without automating the message?

Your posting strategy matters. You need to talk about the right subjects. Keep that aside for a moment. The outreach itself has two steps.

First, build your lead lists. Use keywords in Sales Navigator to find investors who could realistically back the company. Split them into lists by country, industry, portfolio and type of investor, like PE.

Second, systemise the research about each person. I said systemise, not automate. You can delegate it to a team with a clear checklist: if I'm reaching out to this person, I check these three things on their profile. The team builds a draft message and puts it on a Google Sheet. Someone reviews it before it goes out. No AI writing it. One to one.

The goal is to pinch exactly the thing that will start a conversation. That only happens when you know what they post, the takes they've shared, a quote they gave, the issues that touch them. You build a proper profile of each person before you ever message them.

It also helps to have something ready for when they look you up. For a chef I work with, who was approaching investors, we built a website and recorded a podcast about how he came to be. The podcast doesn't have many views and it does nothing for his Instagram. But someone planning to put money into him wants that background. It sits in his email signature. His feedback was that the way we positioned his story gave a very quick impression to everyone he approached.

What if they don't reply on LinkedIn?

LinkedIn is one step, not the whole system. When I raised money for my own business, American Joint, in 2018, I did the profiling through Facebook first, because it was more common then. If the person was on LinkedIn, I reached out there. If they didn't reply, I sent an email. If that didn't work, the last step was WhatsApp.

And for people I simply couldn't reach, I sent handwritten letters. Nobody did that then. The person I actually took money from called me and asked who on earth sends post. I told him I thought it was the only way he would actually listen to me. That's how we raised Rs. 2 crore for a 10% stake.

I don't believe getting to the right person at the right place at the right time is a matter of chance. It happens because of a lot of factors you keep moving around you.

What results should you expect?

Expect small numbers. For an investor client, we profiled people worldwide and reached out from his own profile. He's very connected, so we couldn't send a random message. I did the whole thing myself. From a lead list of 300 people, we got in-person meetings with three. One of those led to an investment. That's a 0.3% conversion, but it solved the problem we set out to solve.

Not every introduction turns into money. With other people, I've booked calls and got them into the right rooms, and it didn't always pan out the way we hoped. Sometimes it grew into something else.

So I never promise a number of calls before I've done the research. I need the problem statement first: which country, which purpose. Then I can lay out the funnel step by step, what the team does, what I delegate, and where you come in.

“It has to be extremely authentic messaging.”

Said on the call, 12 September 2025