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I recently wrote about a LinkedIn message I sent to a CEO and Investor I never had contact with before, that led to a lunch meeting.

Whenever I talk to entrepreneurs who are in the process of raising investors, I hear the same challenge over and over again. “We have tried reaching out to investors through LinkedIn but people rarely respond.”

Every investor is unique, because at the end of the day, it’s people dealing with people. By mentoring over 200 leaders and entrepreneurs over the past years, I have seen what works and what doesn’t work. Here are some of the major reasons why your LinkedIn messages are not getting you the responses you want.


1. You Ask for Money

Imagine you have just identified your ideal partner and go on your first date. Everything seems to be going great. Your romantic dinner is about to start as the waiter opens your favorite bottle of wine.

Then, suddenly, you get down on your knees, reveal a jewel case with a shimmering ring in it, look your date in the eyes and say “Will you marry me?”.

In complete shock, your date gets up and without knowing what to say, runs for the hills.

Dating a potential life partner and dating a potential investor is a very similar process. At the end of the day, you will be in this together for a very long time so you want the relationship to be as valuable and mutually beneficial as possible.

Asking an investor for capital before you even meet in person is like asking somebody on the first date if they will marry you. How do you even know if you want to marry them on the first date?

In their brilliant book “What Every Angel Investor Wants You to Know”, Brian Cohen and John Kador talk about the entrepreneur seeing the investor as an equal. It’s as important for you to ask the investor “Why should I take your money?” as it is for the investor to ask “Why should I invest in your venture?”.

The thing is, before you have met the investor, you just don’t know if this person is right for you. Brian and John rightly point out that a relationship with an investor is a “high touch relationship”.

You can ask for advice or ask the investor something you are curious about in a LinkedIn message. However, don’t ask them to marry you before your first lunch date.


2. It’s All About You

Let’s do a quick assessment. Review the last 2-3 messages you sent to people you wanted to connect with on LinkedIn and check who the message is about. Is it all about you and your brilliant venture? Then you know why you never got a response.

I get these kinds of messages every day. They lack caring. One of my biggest strengths is empathy and that’s why I cringe at messages that only talk about the sender.

How do you feel when somebody sends you an email or message that’s all about them?

That said, it’s ok to talk about you, just not in the first sentence. It’s even important to talk about you in a way that strengthens the purpose of the message. However, each sentence has to be interconnected and seamlessly flow into the next one.

Here’s a good example of a message that got me lunch with a CEO and Investor.


3. You Don’t Answer “Why Should I Care?”

Observe yourself when being approached by others and be aware of the first thing you think when somebody you don’t know contacts you. What’s your first thought?

Most probably, it’s something along the lines of “Why should I care?”. Maybe you use different words but the meaning is similar.

Simon Sinek put this phenomenon perfectly into his famous statement “Start with Why”.

As humans, we want to see purpose in everything we do, no matter how big or small. That’s why this question comes up. And the busier and more popular somebody gets, the better the answer to that question has to be.

Reaching out to me or reaching out to Richard Branson is a very different game.

Before you reach out to an investor, ask yourself “Why should that person care?”. Obsess about that question because if you can’t answer it, the probability for having lunch with that investor is close to zero.

By the way, if your answer is “because they can make 50x their investment back within 5 years”, I recommend going back to the drawing board.

Your reason has to be something personal because that’s the foundation of any successful relationship. Leading with ROI, especially when it’s predicting a future that does not exist yet, is like building your house on a foundation of mud.

Once you come closer to an answer like “Because we are both science-fiction nerds and our favorite book is A Space Odyssey”, the probability for a lunch meeting rises exponentially.


4. Your Message is Fluffy

Fluffy can mean different things. Maybe your message is ways too complex for any normal human being to understand it. Maybe it’s full of formalities. Maybe it’s extremely conceptual and doesn’t really say anything.

A powerful LinkedIn message has to be crystal clear, to the point and only as long as it has to be and not longer. People’s attention span is extremely short. If they have to think about what you are trying to communicate, you have already lost.

The investor has to be able to consume your message in a few seconds in a way that naturally flows. Here’s a great example of a clear, short and to the point message.

Another big issues with a fluffy message is that you are immediately perceived as not being able to communicate in a clear way. Put yourself into the shoes of an investor and ask yourself if you want to invest in an entrepreneur who communicates in a confusing, overly-formal or never-ending way.


5. You Don’t Come Over as Confident

When you write fluffy messages like discussed in the point above, you reflect lack of confidence. A vague pitch, formal talk, lots of “would”, “hope” and “may” or leaving every decision to the investor shows lack of confidence.

Would you want to invest in an entrepreneur who lacks confidence?

To come over confident, it’s essential that you have a crystal clear imagine of your venture’s vision and pitch. You also need to see the investor as an equal and not as some God-like figure. This is your venture and you are in control.

Before you send out a message to an investor, review it, put yourself into the shoes of the investor and ask yourself “Does the person sending this message seem confident?”.

Messages that come over as confident are clear, to the point, relatively short, direct and have a strong call to action. This leads us to the next point.


6. Weak Call to Action

“Looking forward to your feedback” screams for approval and permission. “It would be great to meet you” screams of insecurity and uncertainty.

A weak call to action can be a deal breaker because at the end of the day, that’s what either makes the investor take action on your message or not.

In his famous book “Influence”, Robert B. Cialdini talks about the mental triggers that get people to take action. There is a lot of psychology involved in getting people to say “Yes” to anything. A strong call to action can make a huge difference.

I shared a strong call to action in this article and why it worked so well.

Strong calls to action demonstrate certainty, confidence and clarity. If you reach out to an investor for a meeting, a great call to action already assumes that the meeting will happen.


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