Relationships with Money

We all have a relationship with money whether we want to or not. My relationship with money began at an early age. The knowledge that I could sell something and make money fueled my interests from a young age. Having my own cash to buy what I wanted made absolute sense. From lemonade stands to a cinnamon stick business to babysitting and three jobs by the time I could drive was liberating.

I still remember going to the store and buying my first 10 albums to play on the record player I had purchased along with my incense sticks. Redecorating my bedroom with paint, new bedspreads, and pillows with my own cash was transformative. I was living my own life under the roof of my Mom’s home.

When my parents got divorced is when I really understood money. There was money and then there wasn’t. I was stuck in the middle, too many times, of having to ask my Dad for the check. Money was the white noise in our household. My Grandmother used her wealth to hold power over my Mom who was barely getting by.

Since then I have had my eyes on the prize that money gave you freedom. Funny thing is money gives you freedom but it also can make for strange and strained feelings. I do believe there is a responsibility to giving back and the more you have the more you should give. Understanding taxes, trusts, real estate holdings and passing this on to the next generation is an education in itself with a major responsibility. None of this is as easy as it might look.

I have been thinking about the recent death of Tony Hsieh. At 24, he had sold his first company to Microsoft for $265 million. The ultimate dream? He continued to use his creative brilliant mind to build but at 24 with that kind of cash, who are your peers? Who are you real friends?

I knew Tony through an investment we were in together. We met in person when Fred and I were in Las Vegas for a wedding. He surrounded himself with his crew. They all drank heavily. You could see all the empty bottles in his apartment that we went to. I could see that he had built a wall around himself. Looking back now it makes me sad.

When our lives changed financially it was a big learning moment. I struggled with many things. How do we raise grounded kids who understand the meaning of money and feel comfortable with it? That was my number one concern. Transparency was important too and how much and at what age?

One of my very best friends just sold his company. They worked so hard for a decade and now everything has changed. It is a very weird feeling. Much easier when you are in your late 40’s and early 50’s. Not so much when you are 24.

I recall being at our kids’ school and the woman who ran the main office made a passing comment to me when I was working on something. She said that she didn’t realize how warm and nice I was. I knew what she was saying. That because I had wealth she expected that I would be pompous or snooty.

Very few people talk about their relationships with money and how it has changed relationships, or how they think about it particularly when it comes in like the lottery. That is what we constantly see in the start-up world and it isn’t always that seamless. It is not a conversation people have.

I remember sitting in a “green room” with Scott Belsky talking about this and he commented that nobody talked to him about this and how come. Money is strange. I have had several open conversations with people when they hit the jackpot. I am very honest because the reality is, it has taken me a long time to have a comfortable relationship with money. Sometimes I still struggle.