How to Talk with Billionaires


How to Talk with Billionaires

A lot of us can feel a bit intimidated by uber powerful people, but they’re just people. Learn how it's done from a former professional social butterfly.

I used to be a professional social butterfly.

When I worked in finance for Merrill Lynch, part of my job was to attend black tie events three times a week, and schmooze.

From private penthouse parties, to rented-out museums, I honed my social intelligence skills, chatting with the city’s elite. I did this for two years straight, with my business partner, who happened to be the best wingman ever.

At Jaunty we teach how to connect with anyone, anywhere. A lot of us can feel a bit intimidated by uber powerful people, but you know what? They’re just people. 

How to talk to billionaires

Here’s what I learned about networking and connecting with San Francisco’s upper crust:

1. You get qualified, very quickly

The who’s who crowd is great at sizing people up. Sometimes the intentions are good, sometimes not. They embed conversations with things like, “Who did you come with?” “What do you do?” and “Where do you summer/live?” I don’t think it’s to compete so much as qualifying you as “one of us.” Rolling with these questions but then taking the conversation deeper and making them feel good with humor, fun weaving, and even flirtation, really differentiated us at these events.

2. They are competitive between themselves

As we gained clients within this circle, we learned they were relaxed about their finances and retirement, and upbeat about travel and other experiences. But what really stressed them out was how they were doing in relation to their neighbors. There is a definite hierarchy within these groups and they were always trying to ask us how they compared. Keeping up meant asking where the Jones’ had bought their newest property. Being able to recognize the concerns of the people you are talking to, no matter how ridiculous it may seem, can show empathy. Especially since many other people would roll their eyes, when you consistently keep an open mind, you’re perceived as thoughtful.

3. They are not happier than anyone else

According to a Princeton study, we apparently feel happier the more we earn, but only up to an annual household income of around $75k. Beyond that point, more money may not make us any happier. Most happiness is from within. I met a lot of elites who seemed uninterested in their spouse and bored. Even when feeling unexcited about engaging with someone, putting a wedge in this feeling and really paying attention to what the person is saying with their words and their body, can make all the difference. Seriously, when was the last time you asked what someone’s body language or vocal tonality was really trying to convey? This is where we came in and brought some exciting conversation using stories and empathy. They loved it and this is how we created some great relationships with them. 

4. Don’t put anyone on a pedestal

This one can be hard sometimes, especially if you’re talking with someone who’s done something you think is really cool. But really understanding yourself and getting comfortable with people skills, we can feel social freedom with anyone. Also, if you want to talk the lingo, they always say, “Nice to see you.” and never say “Nice to meet you.” when greeting someone new or not. I use this all the time now.

There’s no right or wrong, or good or bad when it comes to external versus internal status in our lives. However as we discuss in our workshops, we’ve found that internal status trumps external status every time. 

Today, start a conversation with someone with high external status that you wouldn’t ordinarily talk to. Maybe it’s your boss’ boss, or a well-dressed stranger on the street. If you’ve come to one of our free workshops you already have some ideas of what to do. If you’ve attended one of our six-week courses you can take the conversation anywhere you like. Have fun and let me know how it goes!


Eric Waisman

Eric Waisman

Founding Instructor

Liked the article?

Help us reach more people