• 01.25.11

“If you just understood me, you’d love me” – The Mistake That Can Sabotage Your Investor Pitch

Backupify CEO Rob May discusses how the trials and tribulations of the heart are applicable to finding the right investors.

It has been said that pitching investors is not unlike dating: first impressions matter and confidence is key. There’s a lot of truth in that but the advice is easy to misinterpret. An initial pitch session is very much like a first date in that both scenarios reward confidence and being at ease with yourself. (Also, more often than not, they both end in rejection.) Too many entrepreneurs go into an investor pitch with an attitude that’s just as doomed to failure in business as it is in romance, and it reads like this:


“If you just understood me, you’d love me.”

That may make for a great plotline in a romantic comedy but, in real life, that attitude will end in heartbreak. I speak from experience here.

“Why does anyone want to backup their Twitter account?” The room nodded in agreement at the question while I was raising my first round of funding for Backupify, a cloud data backup company. I tried to explain that some companies in compliance-related industries were using social media for marketing and those people needed to archive these new forms of communications for legal reasons. “Sounds like an outlier use case” was the response from the investor who asked the question. Needless to say, I didn’t raise any money from that group — and I’m very lucky it turned out that way.

Fast forward one month: I had the opportunity to present to some of the most active angel investors in the country at an event called the Open Angel Forum. The attitude was totally different. The first guy to approach me when I was done speaking said something like, “I love it. This isn’t about backup, it’s about all this data going to the cloud and replicating the on-premise experience in the cloud.” These investors got it.  I went from not being able to raise a round to having an oversubscribed round in just a month. My pitch had not changed, the only thing different was the investors I was pitching to.

In my early days as an entrepreneur, I thought the key to raising money was to be convincing. If an investor didn’t like my idea, I would work on a plan to convince him or her why I was right. That approach was entirely wrong.

“If you just understood me, you’d love me.”


The key to raising money is to search for the right investor. You aren’t trying to convince someone your ideas are correct, you are trying to find someone who already believes in what you are doing. You can’t debate someone into loving you, your ideas or your company. They’re into you or they’re not. Pretending otherwise simply doesn’t work.

I can’t stress this axiom enough because the pitching-is-like-dating metaphor has a logical extension. Investing is like getting married.

Your investors are your business spouses. (In the early stages of startups, you’ll often see your cofounders and investors more often than your actual spouses.) You don’t want to find a potential spouse who doesn’t like you and convince him or her that really they do love you. Instead you want to find someone who is a match.

An investor that signs onto your company with reservations is like a spouse that agrees to get married despite lingering doubts. How healthy is that relationship? How likely is it to withstand the sickness and the health, the for-better-or-for-worse that life and business will inevitably throw at you? Not very.

“If you just understood me, you’d love me.”



“You understand me? Let’s talk.”


That good advice for any relationship, business or otherwise.

About the author

Rob started his career as a digital design engineer at Harris Corporation, where he worked on graphics processing chips for the Comanche helicopter. After Harris, Rob taught in the business school at the University of Louisville, then moved on to a business development position for a wireless software startup.