I Dated a Billionaire. One thing Karen McDougal and I have in common.

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atching the Karen McDougal interview I was first stunned and then compelled to write.

You see, not too long ago, I dated a billionaire. The man was immensely rich and showed me around his social circles. We spent New Year’s Eve together at his private club.  I spent a lot of time at several of his mansions.

I’m not a Playboy model or any model for that matter. Far from it. We were introduced by a mutual friend because  T.D. (yes even his initials are the same only reversed) was looking for someone to help him with the details of a memoires he was writing as a Jewish child in Germany. We had great conversations, he invited me to stay over at his Malibu mansion and I fought off his advances because I wanted to keep it professional.

Intellect, it turns out was as much an aphrodisiac as model-status. He thought I was magnetic, inside and out. His idea of a trophy was not a model portfolio but academic credentials, a German background was an added plus …and I filled the bill.

But what really struck me in the Karen McDougal interview is something not discussed on the news and yet for me it stuck out, something I could not get out of my mind. Because, you see, it was the same reason I dated my billionaire. Karen spoke about how she got into the Trump affair in the first place. At the time, she was trying to free herself from a relationship with a man who constantly made her feel she was not enough. No matter what she did, how gorgeous she was, how high she climbed in society, she needed a man to validate her being enough.

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I felt simultaneously stunned and embarrassed.

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Like Karen, I had a ‘stormy’ relationship with an on-and-off again boyfriend at that time, It was a particularly vulnerable time in my life.  Like Karen, I felt defined by ’Not Being Enough.’

When the billionaire showed up, it was an easy way out of the relationship and to prove to myself and the boyfriend that indeed I was ‘enough.’

How many of us have been under the spell of not being enough and only a relationship could make it ‘alright’ or give us the stamp of being worthy, valuable. Wether that relationship was a billionaire or not scarcely makes any difference.

We define ourselves from the outside. We crave validation. Especially when going through vulnerable times as all of us do sooner or later.nNor does it matter how gorgeous, smart, well-spoken, or classy we are. Seek validation from a man.

For Karen as for me, there was the allure in ‘being enough’ more so than his massive wealth it was the validation of being enough for a mega rich billionaire who shows us off in his social circles.

I and of had an awareness of this at the time. In that Malibu mansion, I heard the mighty Pacific ocean waves crashing at the cliffs below the master bedroom. It felt somehow straight out of a Hitchcock movie, ‘Rebecca’ perhaps.

Unlike Karen McDougall, In never was in love with this man. And yet I let him take me out. We went to a five star restaurant. In the afternoons he take me to his drive-in wine cave, custom-built underneath one of his Beverly Hills mansions up the hill at Benedict Canyon The cave stored  thousands of exorbitantly priced wines bottles, worth easily well over several million dollars. He brought his own bottles of wine to the restaurants we frequented. He much preferred to pay the corking fee than settle for a wine he had not previously carefully selected for us. The sommelier’s eyes popping as he get a glimpse of the expensive label.

It was fun and yet I had enough self-preservation to know this was going no where. Nor was I in love with this man.

But back to our story of Karen. I do not judge her. I know exactly how she might have felt.

Karen took all of her self-worth from influential men. And so did I at one point.

People who saw me at that time asked “What happened you? Your eyes look like you saw something marvelous!” And I did, I saw my worth! Only The problem was, I saw my worth filtered through another person.

They didn’t know. Only a handful of people knew of it.

But I knew.

But now I know better.

I was unable to see the worth inside myself that was there all along. Instead I gave my power away to a man, who displayed his staggering wealth.

I do not judge Karen McDougal. My heart goes out to her. This gorgeous woman who tried to escape one relationship where she was not enough, only to get herself head over heels into another that seemed to validate her. Only at the end that affair also let her into the ‘not enough’ trap.

Here is why I am furious. Because women take their self-worth from outside. I think we have been conditioned since we were little girls.

Many times we give up or do not pursue our business and independence because being a girl boss is just not as ‘sexy’ compared to being the mistress of a billionaire.

That is why I’m so passionate about helping women develop their business and entrepreneurship and the identity that comes with it.

That’s the bright side of it. More than ever we have the opportunity not only to be financially independent but to define ourselves from the inside out, by our own measures. And that, my ladies, is the ultimate goal of female entrepreneurship, for us and future generations.



Do you have an inner Dream Whisperer? But you can barely hear her voice because your Dream Killers scream louder? Are these your TWO biggest