Over the years I’ve seen some startup fails that have made me cringe in pain for the Founders, thinking “No they didn’t!” I truly felt for them. I almost wished the ground would open up and swallow them because that would be less painful.

Several investors over the years have candidly shared faux pas and “no pas” that they strongly recommend avoiding. Here’s just a few of these painful moments and some suggestions on how to avoid falling in to the same traps. Identities have been changed to protect the innocent - and the not so innocent.

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Epic Pitch Fail #1

Not Doing Your Homework

Some startups try the “spray and pray” method, sending cold emails, eventually getting a few meetings. Hey, it can work, and some investors are more responsive to it than others. Others get introduced by a trusted connection and this alone merits a “yes” to a meeting. Either of these and many other methods are fine. Where’s the fail? Not finding our anything about the investor before you ask for an intro, send an email or even before you meet. “Robert” - Managing Partner of a VC told me that one of his favorite questions is “So why do you think we’re the right fit for you?” He’s astounded by how many Founders hemmed and hawwed without an answer. He goes even bolder - “What do you know about us?” - the answers are usually more hemming and hawwing with a series of grunts.

How to Avoid it?

Research the Investor/s BEFORE the meeting - look at their portfolio, do they invest in your area? Great! Use that as an opener. Do you have a direct competitor that they’ve invested in? Don’t meet them! Is there a potential collaboration with one of their portfolio companies? Emphasize this! Find trends and themes to their strategy and bring those up in an email or a meeting to show your knowledge and make them feel like you bothered to learn about them. This, by the way, should be the rule of thumb for any meeting - it’s basically what LinkedIn was invented for...

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Epic Pitch Fail #2

Talking Trash

“Heidi,” a Junior Partner at a VC told me about a time she asked a team about their competition, specifically one pretty direct competitor and the CEO answered “Oh they are no competition for us, they basically suck at what they do.” Heidi smiled a bit sheepishly and then proceeded to tell them that she was on their Advisory Board, not as an investor, rather as someone who had extensive industry knowledge about their field and she thought they were actually quite good. The CEO turned a few different shades of red and needless to say, the meeting was over. Could the CEO have known this before? Maybe… But there’s a better way to avoid it:

How to Avoid it?

Don’t EVER diss your competition! Ever! You never know who knows who, who’s connected to whom. Stay factual - “Well Competitor X does XYZ and actually doing quite well with it based on the $15M Round they just closed. We also do XYZ but with a different approach, set of tools, method, which enables us to also do ABC…” Play off the strengths of your competitors to highlight your strengths and then stress your points of differentiation. Dissing someone reflects badly on you and it signals that if you trash talk about your competition - who else are you talking this way about…?