Good pitch is an optimization, not a win

Why you should never beat yourself up for not making a good pitch

Photo credit: Stefan Vladimirov

For the past 3 years of building Swipes, we’ve made hundreds of pitches. Some bad ones, some really bad ones (like forgetting 2 times the presentation on stage in front of 300 top investors and saying F*ck, F*ck unintentionally) and some darn good ones.

We made pitches to customers, partners, journalists, angels, funds, accelerators, audiences, friends, family…basically to anyone willing to listen. Initially, I was really working myself up for each of these pitches. You see, as an entrepreneur, you are told:

“You’ve got to nail your pitch.”
“You should always be pitching.”
“You should be able to deliver no matter what. Even if someone wakes you up in the middle of the night.” (When did that ever happen?)

Some accelerator programs spend months teaching you how to pitch.

And whereas I agree that making a good presentation is a great thing, making a bad one is not a dead end!

Image credit: https://phasetwolearning.wordpress.com/tag/presentation-skills/

I learned that the hard way. Spending hundreds of hours on preparing for meetings that didn’t matter and beating myself up after each conversation that didn’t lead to a beneficial outcome — what could I have done better, why didn’t I prepare better, what if this, what if that…

Reality is that even if I had done everything perfect, the deal wouldn’t have happened because there was simply not a match. No one invests in you or buys from you because you did a great presentation. It’s not a charity. (unless it is.) Because of a great pitch, you might get people to listen to you longer but at the end of the day, a deal will only be closed if there is a match of their needs — your solution, their interest - your results, powered up with good chemistry on both ends.

All our investors wanted to work with us, as much as we wanted to work with them. Did we hm’ed too much on the pitch? Sure. Did we say tons of wrong things? You bet. Did it matter? No. There was a match.

We never closed a deal with someone who wasn’t excited. We spent tons of time convincing people because they seemed interesting (industry expertise, brand name, big clients), and we were fighting hard for their attention. But looking back in time — this was a waste of time.

Better pitch would have been an optimization, but not a win.

And at the end of the day, only the wins count.


Spending time to perfect a conversation to an interesting but not interested person is a waste of time. Time you could have otherwise put into generating results, making interested people even more interested.

Think about this next time you’re in a dead end meeting with someone who stares at you blankly and dreams to be elsewhere.