I pitched 150+ entities over the years as both a start-up exec and a founder. And I guess maybe I’ve been on the other side of 150 meetings, too.

Nothing in fundraising really phased me as a founder — for the most part. Except one set of meetings.

Raising money is selling stock. It’s sales. You have to expect No’s, Maybe’s, Possibly IF’s, etc. If you can’t have 50 doors slammed on you to get to one Yes, one closed deal, if you can’t take that without taking it personally — then sales isn’t for you.

So roll with it, and I rolled with it.

Except the one time, I had 2 top-tier VC firms lined up. We did the first pitch in the morning. It genuinely went well. All the partners came (always a strong sign), and there was a bunch of talk on deal size and structure, etc. before we left. We shook hands, had some lunch on Sand Hill, and then went to our second meeting a few hours later.

When we walked into the second VC pitch, the partners were all smiles. Why? They’d “already talked to” the last firm from that morning and “were very excited to dig in.”

That seeming collusion did shake me. Sales is sales, and prospects should be able to call each other and even team up, perhaps. But it felt like a challenging, then-opaque system was rigged against me.

In the end, neither firm got us a term sheet. That’s OK of course. But I think in the end, each of their valid concerns likely compounded each other, and one firm talked the other out of it, and vice-versa. But it doesn’t matter.

The second hardest part of VC pitching is that it is sales, and for 99.9% of us, a really tough sale.

Feeling the deck is further stacked against you is what made it the worst of 150 for me.

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