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The last few days have been beautiful fall weather, and I can't help but wonder – do you ever miss having your Ferrari convertible?


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Although some days are perfect convertible weather, given I barely drove it the last few years I owned it, averaging less than 50 miles a year, I can honestly say, "No." In fact, I cannot even remember the last time I drove it.


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I can't help you with that, but I'll never forget the last day we taught at KIPP Houston High School, and you drove it there. You should've seen the student's faces as you were lowering the top on it.


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Funny thing is I never took the car to KIPP because I did not want anyone to think I was showing off, but I forgot how exciting it is for motorheads to see special cars – whether new or vintage.


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I doubt everyone crowding around your car was a motorhead, but they certainly were excited to see your car. Boys AND girls! At the risk of sounding warm and fuzzy, I think the fact you not only drove a Ferrari, but also raced them, gave the girls a feeling of empowerment, that they really can do anything.


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I guess because I always worked in male-dominated industries, I got used to being the "token" woman. Regardless, I never look at things as being gender-specific.


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That's because you never look at anything like the rest of the world does, or at least most people do. A perfect example of that is you giving Juan a ride in the Ferrari. I doubt many people would have done that.


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It seemed only fair since he tried to make a "deal" with me the day before – a hand of poker or even a flip of a coin. If he wins, he gets a ride in the Ferrari. If I win, he will be my slave for a day. Giving him a ride in the car was a reward for having the chutzpah to try to make a deal with me. And, in the two years we taught at KIPP, of the over 200 students who took our Personal Finance & Life 101 class, he was the only one ever to do that.


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I'll never forget how you also told them that although it may not be the proper definition for the Yiddish word "chutzpah," the real-life definition is "having balls."


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How else would you explain it?


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You should know as many people have used that word to describe you. And it was consistent with the lesson we taught them about how you "confronted" Bob Weinstein (of the movie producing Weinstein Brothers) at a conference in New York. (Granted, it was well before the #MeToo scandal.) You realized you had nothing to lose, not to mention you were well-prepared.


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In most scenarios, if you do not ask for something, you will not receive it. So, what is the risk of asking? Someone may say "no"? The way I see it, you are no worse off than before you asked. So, in reality, there is no downside risk, but there IS upside potential. They may say "yes."


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True. And I laughed, although I wasn't surprised when everyone else started asking for a ride in the Ferrari!


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Except Juan did not just ask for a ride. He tried to negotiate a deal. He structured it so that there was an upside for me if he lost the bet, which obviously would be the downside for him. But, what impressed me the most was that he was proactive and took a chance, albeit a long shot, to get something he wanted.


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And given the smile on his face when you drove off, it obviously paid off. I bet, even though it has been many years, it's something he's never forgotten.


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The lesson or the ride in the Ferrari?


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Both. And I will go out on a limb and say I bet many of the kids standing around the car when you told Juan to jump in, and then explained why, may also remember not only that day but the importance of the lesson.


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Then, it was a perfect day for a convertible ride.
Photo by Aneese on iStock


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Thanks for sending me Natasha's Austin-inspired business plan. But while I know that's her future, I can't help but think about the first time I took her to Austin.


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All I remember is that it was love at first sight.


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It was on our way home from taking Sawyer to camp, and I told her we were making a slight "detour". She was so excited when I pulled up to the hotel as she's always loved hotels. But that night, as we walked onto Congress Avenue Bridge and saw the thousands and thousands of bats fly out into the sunset, she was mesmerized and "in love".
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Underlying photo by Alleko on iStock


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I know that Yom Kippur isn't exactly known as one of the "fun" Jewish holidays, but every year I can't help but laugh at what's easily my number one Yom Kippur memory.


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That is what makes memories … memorable. And, finding something to laugh at on Yom Kippur, the Day of Atonement, which is probably the most important and solemn Jewish holiday, would be memorable.


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I can't believe you're not even curious what it is!?
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I'm still smiling at you letting Sawyer drive your Mercedes G-wagen. Although I know that her dream car's a Ford F-150, I think yours is her "fantasy car".


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I knew the "long way" to drive back to your house, but after asking her if she knew the best way, it seemed easier to have her drive.


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Well, you might have thought of it as efficient, but she thought it was exciting. And she told me that she was honored you trusted her to drive.


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Did she mention that once we got back to your neighborhood, we saw a huge turtle on the road? Moving very slowly, of course, so I was not concerned it would become an unexpected road obstacle.
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