Hustle The Most Episode 3: Betting against the odds!

Episode 3 Betting Against The Odds: How my dad hustled me and bet against his own son based on his past learnings of having 4 kids before me.

We all have ideas on a daily basis. Some of the idea are probably amazing and some of them are the exact opposite. What happens when you don’t follow through? What about the ideas that you forget about? My dad bet against me and even cheered me on to move forward with an idea that he thought was a pipe dream.

I had a chance to go to California was I was 12. One of my good friends in the neighborhood his dad lived somewhere around San Diego. He was going out there so visit him and he asked me to go with him. I was 12 and had never really been anywhere other than Cedar Point which is this amazing amusement park in Sandusky Ohio. I was pretty siked about this and was thinking that this would be the trip of a lifetime. I had never been on a plane or even driven anywhere far away so I this seemed like a cool idea.

So I sat down with my dad and I timed this conversation pretty strategically. I started to tell him about how I had this amazing opportunity. It was very much a “what do I have to do to put you in this used car today” type conversation. I asked my dad If I could go and he was like “yeah of course, that sounds awesome”. Like he agreed right away with almost no questions asked. My dad even said it would give me $100 to spend while I was there. This was awesome to 12 year old me. But thinking back on he answered almost too quickly. It was kind of like when your friend would be like  “I’ll be you a hundred bucks I can jump over that creek and your response is I’ll be you a thousand buck” because you were sooo confident that we would never make it. This was 1990 so $100 went a lot farther than it does today.

I remember at the time my parents absolutely forbid me to be anywhere near a skateboard. They didn’t want another huge hospital bill coming to the house and I don’t think my mouth could handle another curbing. My dad was a little more forgiving than my mom plus I was the last of 5 kids so my brothers and sisters kind of paved the way for me. I had this conversation with my Dad about a week after he agrees to let me go to california about me getting a skateboard. Again this was supposed to be a persuasive conversation to obviously go in my favor.

It went something like. Dad California is known for skateboarding. If I go to california I want to be able to enjoy myself and make the most of my time there. Which means I want to be a good skateboarder when I get there, I don’t want to be there and just learning. I think I should get a skateboard and learn to skate before going to california. I must have sold it pretty hard because my dad agreed. He said you can have a skateboard but only on 2 conditions, First you can not tell you mom and second, I am not buying it for you.

I had my conditional approval. This is where I started learning about trading stuff and kind of perceived value over monetary value. For years before this I had been returning soda and beer cans and used most of that money to buy candy and baseball cards. I used to hang out on the porch and trade cards with kids in the neighborhood. There were a lot of all day trading sessions around 1989 tops and fleer cards. Once in a while kids would show up with some crazy new cards that they got from a card show. It was pretty cool.

A lot of kids go through these phases where they collect cards, then get into different stuff as they get older. I went from cards to comics and back to cards and just kind of dabbled in between.. I had a good amount of both and knew a lot about both of them. There was cool card shop that we used to ride our bikes to called Mike’s Upper Deck. It was a small shop that was just packed with cards. I don’t remember much about the guy that owned it other than he didn’t care much for Jose Canseco. I remember they had these 12” player kind of figures that were like a hundred bucks and I really wanted the Canseco. It was like I want that Canseco one and they owner said to me



”Aw man, Conceco is a putz, take Gibson” which was the next figure over he was playing for the Dodgers the time but he was a michigan native and and ex Detroit Tiger so they were big fans. Either way we spend a lot time up there but today was about  how I was going to get this a skateboard so I could practice for my big upcoming trip to the west coast!


I started with my baseball cards it was the only thing I really had that was worth anything. I knew a kid up the street that used to collect comics and went to cards kind of like but just flip flopped like me. I humped a few monsterboxes and books full of cards up to his house and we started swapping. We swapped mainly Cards for comics. This was the start of a plan. There were some other kids in the neighborhood that had all the skate stuff you could ever want. These guys got into skating early and just started collecting skate stuff.

I think they would just get new stuff and never get rid of the old stuff. They were also into comics, baseball and basketball cards. I ended up swapping cards for comics and comics for skateboard parts. When it was all said and done I ended up with a set of blue Venture Trucks, some Bullet Coffin Cut Wheels and a spoon nose Billy Ruff Pro model. It was not pretty. It was all used and somewhat beat up but it was mine.


I will give you a spoiler here, I never made it to California that summer.


It’s funny looking back there was probably a 3% chance that I would have made it to California. I mean tickets then were probably $200-$400 and we always had Zero dollars I don’t know how we would have ever afforded a ticket. The only way then to buy a ticket was at a travel agency or at the airport. There were no deals to be found on priceline or expedia. I would have a better chance of riding my new skateboard all the way to california than flying there.

My dad kind of played me little. He knew that I would probably get over it, he knew that it was just a flash in the pan idea and I would probably just forget about it. I think this happens with kids and even adults, a good idea today doesn’t always mean you follow through with it tomorrow. But sometimes you just can’t contain that initial excitement.

Thinking back on it My dad really just played the odds and just told me of course I could go and I’ll even give you money. He knew I wasn’t going, he knew I would forget about it. Rather than make me upset he took a chance and let it all ride on the fact that I would just forget about it and he was right.


My dad hustled me.

So what did I learn from all this?

I learned that you have to know your content. When you are selling and hustling anything you have to know what you are selling, what you are buying and what’s it’s worth. You have to do the research. Understand the landscape if you don’t there is a good chance you will get burned.

I also learned that Value doesn’t always mean valuable. Think about your favorite things in this world they probably aren’t things that are very expensive but they have value to you. Personal value. If someone broke into your house and stole your TV you would be mad but you can replace that. If they broke in a stole a $10 ring that your dad gave you when he passed away your world could potentially come crashing down.

Lastly, I think I think that we will always be learning so have to be open to it. My dad only bet on the odds because he had 4 kids before me and learned how to navigate these situations. He knew the landscape, he thought that they odds were in his favor based on experience…

And he was right.



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