The editor’s own story about being in a weird money situation.

I told this story to Chelsea, the author above, when she was writing her etiquette of economically diverse friendships piece and her response was: “Great story. But I don’t think that’s common.”

One night a very-successful former coworker invited me to a steak dinner with friends. I was excited to go, but also some part of me thought the night might turn into an expensive adventure.

I think adventures are fine and fun. In tech right now there’s definitely a wrong way to party. It’s always been the wrong way and now there’s a much stronger spotlight on the people that still party this way. But there’s still also time for the right way to party. I thought this crew was capable of “the right way” — dudes on a no-grope, no-cat-call, alcohol fueled adventure.

I literally said to my partner Sarah, “I wouldn’t be surprised if we end up in Vegas. Maybe I should set a budget for myself.”

My finances are that in terms of liquidity and savings “I am fine.” and that’s how I tend to look at things. I do hold three live lottery tickets in the form of options in living startups that I think will survive. But I try not to think about those.

So, “I’m fine.” But I’m not dripping with liquidity. When I went to think of a budget I decided on $1500. That’s A TON OF MONEY to go out with friends for a steak dinner. But it’s also a reasonable amount of money to spend on a once-in-a-lifetime adventure.

Here’s how the dinner shook out in terms of net worth. There was one billionaire. There were three other exited-their-startup millionaires. And one more VP who’d just gone through an IPO. And me. That’s six of us total.

I was 100% committed to carrying my own financial weight and assumed I would be splitting the bill on an expensive meal. First estimate, I was in for $150.

The initial indication that the night was going to get more expensive was that the Billionaire guy asked for a bottle of wine from 1986.

Now, I hate thinking of this guy as “The Billionaire Guy.” The reason I was at the dinner is because in almost all situations I am legit friends with those people and normally have a peer relationship where we are talking about new products and early-stage startups. “The Billionaire Guy” is also my friend of ten years.

But this is the reason I asked Chelsea to write the article I’m responding to. When you are friends with people in different financial brackets you end up in weird situations that are defined by money.

Anyway. I’m pretty sure this bottle of wine was super expensive. I never knew the exact price. But the request to the sommelier wasn’t “Do you have any cheap bottles of wine from the 80s?”

This is the first moment that created a bit of a weird dynamic at the table. My reaction was “I can’t pay for that.”

And then I noticed eyebrows raised at the table. I’m pretty sure that’s when the rest of the table started assuming that the Billionaire guy (i.e. my good friend of ten years) was going to treat for dinner.

And in terms of etiquette, the Billionaire absolutely should have treated and in the end, he did. But more importantly, that would have been a great time to turn to us and say, “Dinner is my treat.”

I’m not telling you this story because of the expensive wine though.

At the end of the meal, someone broached the idea of going to Vegas. Exactly as I predicted.

Someone else said that they’d just put down the membership fee for BlackJet (now defunct), an Uber for private jets app.

And so we had to know. How much would it cost to charter a jet to Vegas that night? $9,000.

My budget was $1500. There were six people at dinner. In other words, it was exactly my budget to fly to Vegas and then not have any way to get home.

Here’s where I turn to another friend, a fund manager in NYC, who is my example of leading on the etiquette of money. She sits in the middle of an eclectic group of friends. Some are other fund managers. Some are artists. Others are chefs. Others are friends she met in the bleachers watching Yankees games. Sarah and I are her tech friends.

And she is the master at setting expectations up front about what she can pay for and what other people are gong to pay for. From her perspective, money has allowed her freedom. She doesn’t want to get taken advantage of, but she also doesn’t want to not be able to share the best experiences with the most interesting people.

I went on a group trip with her to Egypt and we ended up eating a home-cooked meal in the home of the most famous chef from Egypt’s version of The Food Network. This Egyptian chef had grown up watching one of the chefs on our tour on the actual Food Network. That’s a pretty unique experience for everyone involved, set up by not making net-worth a requirement for who was on the trip.

And I think that’s why people with a lot of money want to treat. It’s not about generosity or feeling sorry for their poor friends. It’s just about using money to live the life they want to live.

I think it can be hard on your pride to be friends with richer people. What does it mean about your value as a person when they try to pay for something? But I’ve come to just realize that my richer friends are trying to live their best life and accepting their generosity is mostly about not blocking the life they want to live. It’s not about me in other words (beyond the wonderful fact that they legit like spending time with me).

So — back to my dinner. That table debated pretty heavily about wether to go to Vegas on a chartered flight. And I think they were absolutely entitled to spend their money on that sort of adventure.

As the debate got closer to a decision, I knew I just had to say something clear about my own budget. My line, prepped and ready to go was, “Guys, I’d love to go. But my budget for the night is $1500 and this looks like it’s more than I can afford.”

I’m 95% certain that if I had been clear about my budget that my flight would have been comped and I would have then been asked to drop $1500 on drinks and gambling. And that would have been fine.

Unfortunately — the men at this table are just hitting that life stage where they also have real responsibility. Everyone had a little grey in their hair. And most everyone had kids to get back to. So we didn’t go to Vegas. But we were really damn close.

Written by

Human potential busy body. Founded @coachdotme, @bttrHumans, @bttrMarketing. Helped @medium @calm. Current work focus: Habit Coach Certification.

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