Weekend in Napa for having connected them to an exec they hired. Gift certificate to Masa’s restaurant for helping with a fruitful introduction. Bottle of wine for, well, I don’t remember but people occasionally send me alcohol. All unexpected but appreciated. Generally though, the Valley does a shitty job of gift giving. We’re just not attuned to the nuance and etiquette. In some ways, our culture even rejects the idea. But wow, a well-timed and appropriate “thank you” accompanied by something tangible makes a lasting impression, and actually ends up being a pretty inexpensive way of maintaining relationships.

Oh sure, we know how to offer $10k (or a year of BBQ) as a referral bonus if you find me an engineer. And we’re solid on throwing advisory equity grants around for ongoing access to someone – in some ways, access to funding rounds is our equivalent of the Hollywood muffin basket). But tossing someone some hipster socks, an Uber gift certificate or weekend in Big Sur? We just haven’t mastered the art of the ‘here’s a little something’ like New York or LA. Why?

1. Friction – fewer assistants or underlings to manage this stuff. And who knows peoples addresses for shipping – i can’t even spell or pronounce the last names of good friends (blame email autofill). Maybe mobile gifting via services like Facebook will result in a generosity spike by eliminating the need to do anything outside of clicking a few buttons and entering your credit card.

2. Culture – maybe I’m doing it wrong, but we pride ourselves on being less transactional in the moment and more community oriented. We help out not because we expect immediate recompense but because it’s how one pays into the pool. Later you’ll ask for favors back, drawing on the goodwill. Giving someone a thank you gift may awkwardly recharacterize the interaction. I’m not a prostitute so why are we haggling over price? I don’t want to be indebted to you so don’t try to buy me.

3. Conflict of Interest – simple gestures can look very different when they end with an item of value being exchanged. A gift too valuable or in some cases, even just anything with a price tag turns innocence into questionable ethics. That reference check I did for a friend? Bottle of wine sure makes it seem like “thanks for not telling them about the time I falsified my expense reports.” Unrequested gifts can lead to unexpected problems.

Now all this being said, I’m going to stick to my original premise: we undergift in Silicon Valley. Consider me guilty of infractions on both sides – situations where I feel like a thank you would have been nice but never arrived; and occasions where I should have sent an appreciative package instead of just an email. Here are my unofficial etiquette tips to gift giving within the tech world.

A. Consider making a charitable donation in someone’s name. Removed the obligation and conflict of interest issues. Make sure it’s an organization the recipient cares about, not just one you think is worthy.

B. Avoid cash – or things which smell like cash (iTunes gift cards, AmEx cheques, etc)

C. Go for unique as opposed to showy. I don’t need another iPad but if you find me a small batch whiskey or the best toe nail clipper I’ll remember you. Same thing with experiences – although harder to coordinate, often more memorable.

D. If concerned, ask first – “hey, we wanted to thank you for the great advice the other day. Would you mind if we sent over a small gift?” Most people will respond “Totally not necessary” but you can still send. It’s only if they say “My company doesn’t let me accept gifts” or some variation on “I really wish you wouldn’t” that you can politely back away.