During my time as a personal financial planner for the extremely wealthy, I learned that rich people also put their pants on one leg at a time.

You: What kind of planning, exactly, were you doing?

I was speaking metaphorically.

You: Yeah, sure you were.

There were some really great clients and some that were, let’s just say, less so. Some clients were extremely down to earth and others were completely full of themselves. After a few years of doing this kind of work, I came up some general rules by which I could accurately predict which client would be which (that is, fun or an a$$hl$#) before I even met them.

In preparation for the meeting, I’d ask my boss how the client had acquired their money. From that one bit of information, I’d be mentally prepared. Like all stereotypes, there’s some risk and I was mistaken at times, but I thought I’d share my mindset at the time. I welcome your thoughts on your experiences.

Here are the six ways to obtain significant wealth and the attitudes that go along with them, in my opinion only:

1. Earn it as an Entrepreneur

Entrepreneurs were my favorite clients. Now that I’m an entrepreneur myself, perhaps that explains part of it; people like people who are similar to them. But I don’t think so. After all, we’d have to sell Beyond Paycheck to Paycheck to each American 10 times to reach a respectable fraction of the level of wealth many of my clients had already achieved.

Rather, I think it was the entrepreneur’s attitude I most enjoyed. They had worked really, really hard for their money, they were glad to have made it, but appreciated that it was just money. They wanted it taken care of, but for many, their journey really wasn’t about the money and it certainly was not their measuring stick. As a result, they didn’t let it define them. In short, they talked to the little people (like me) with the same respect as my boss’ boss. So of course I worked harder on their accounts.

2. Earn it as an Executive of a Large Company

This was the hardest group to stereotype, since I found variability by industry. Those in fast growing industries (like technology) thought they had conquered the world –and some actually had. As such, they were often receptive to new ideas and eager to engage in active discussions. Others, primarily in slowing industries, were understandably more defensive about their wealth, both in terms of their strategies and their attitudes about it.

3. Inherit it

Those who inherit a ton of money are an interesting lot. Many knew they would have a rich adulthood before they went to prom, in a stretch limo. Wearing diamonds. With Bono. But I found many of those extremely wealthy by inheritance to be extremely thoughtful. Old money often brought old multi-generational traditions. Many of those were good things. As a group, they understood a greater sense of place. Managing their legacies was of utmost importance. Many worked very hard without–from a financial perspective–ever needing to do so.

4. Marry it.

These were the clients and conversations I dreaded the most. Unfortunately, many of those who married money felt that they had earned it. But they haven’t. I’m not saying they married for money. After all, how would I know what was really in their hearts? But my own experience with those who had married the extremely affluent was an attitude you could smell a mile away. These were the least receptive folks to any ideas and people. They were much too busy to implement any plans (even the really important ones) despite having no claim to a day job or meaningful volunteer work. I once theorized that one of my clients daytimes was exclusively occupied by playing video games. I couldn’t prove it, but we all agreed that no one in the office had a better theory.

5. Win it.

A great group, at least at the beginning of their wealth cycle. Realizing that they were among life’s most fortunate, those who listened to their advisors typically remained so. Humble too. But those who didn’t heed the advice of experts quickly found themselves out of luck—and out of the offices of firms such as the ones I used to work for.

6. Get it Another Way (Like Through Sports or Entertainment)

I didn’t really work with too many from this group, but I had to put it in here as it’s the most obvious group of people who can obtain a lot of money from a source not yet discussed. It’s telling that there are so few of these people compared to the other groups mentioned – yet they have entire magazines and television shows dedicated to watching their exploits while the other groups only have some older books.

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Thoughts? What kind of person would you like to be? What if you had a bunch of money? How would you be sure the money didn’t change you? Or would you want it to?

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