How It Actually Feels When an Investor Writes a Check at the End of a Coffee Meeting

I was meeting with a young founder shortly after his return from a two week fundraising “road trip” to the Bay Area. I asked him “How’d it go?”

“Not well,” he responded. “We didn’t get any checks.”

“Of course you didn’t,” I replied. “That’s not how fundraising works. This isn’t a movie. People don’t just hand you checks for thousands of dollars at the end of coffee meetings.”

“I know,” he admitted. “But still, I figured we’d at least get someone to propose deal terms.”

I understood his perspective. I used to have the same expectations around fundraising and what “successful” fundraising looked like. Paradoxically, the thing that finally convinced me investors don’t just “write checks” at the end of successful coffee meetings was the one time an investor literally wrote me a check at the end of a successful coffee meeting.

I was raising my initial venture round for whatever startup I was running at the time. Prior to that, I’d raised a small angel round, so I was working on my first round that included professional investors. I had the deal nearly sewn up when I heard about an angel investor coming to town that I’d been friendly with for a few years while living in a different city. I reached out and…