A while back I wrote an article entitled “Why a $20,000 loss was the best investment I ever made.” It was the story of how I once took a stock tip from a buddy of mine who at the time was working for Jim Cramer. Cramer was very hot on a particular stock. So I, without even hesitating, decided to buy way more of this stock than I should have. It resulted in me losing over 20 grand in a relatively short period of time. It was a pretty big blow. At the time I didn’t exactly have a ton of savings and this loss was way above an acceptable stress level. However, as I regrouped, a huge wave of calm came over me. Up until that point I had been taking tips and here and there, making a little money, etc etc. But one thing that was common whenever I’d “bet” on a stock was that I’d become stressed. However, since I had been “winning” on most of the tips I was getting, I finally decided to bet the farm. And of course, it bit me in the ass. When that loss became reality though, I felt a huge sense of relief. It was as if I had finally given myself permission to go with how I was feeling all along. And how I was feeling was that I never really wanted anyone’s advice or tips, I never wanted to blame anyone else for the money I lost or won for that matter. It was one of the first times I felt true ownership over my stock investments. And from that point on I’ve always taken full responsibility for any investment I’ve ever made, good or bad. Thankfully I’ve turned out to be right more than I’ve been wrong with my portfolio. I truly believe that’s because I do my own research, invest only to the extent I can sleep at night, and try to keep my emotions out of it. But this is just one example of a “bad” investment that wasn’t really bad at all. And folks, “investing” doesn’t always have to be money, It can be time, effort, energy, anything. Here are a couple examples of bad investments I’ve made that in retrospect, weren’t bad at all.
$60,000 in six months
Back when I had a business partner, we made plenty of decisions together but there’s one that sticks out as being one of the worst we ever made. At the time we owned a solid portfolio of websites and we were making good money with ads. However, we were never able to get any direct deals. Most of our ads came from places like Google’s Ad Exchange or other ad networks. In other words, we didn’t have any direct relationships with companies who wanted to advertise on our websites. These deals were tough to come by and we concluded that we needed outside help to try and secure these deals. We knew a guy in our space who we weren’t 100% fond of but we knew he was successful. We had done business with him on a small scale and saw that he had some relationships we were seeking. Long story short, he kind of sweet talked his way into being a “consultant” of ours promising to provide us with as many private ad deals as possible. The deal was we’d pay him $10,000 a month without any kind of end date.
From day 1 he sucked. We knew he wasn’t doing any prospecting whatsoever. He was trying to leverage relationships he already had and was essentially playing us the entire time. While we didn’t officially know how much work he was putting in (actually we didn’t care as long as he earned out), but we knew it was the bare minimum if that. It was as stringy a relationship as you could possibly have. No structure. Our weekly calls were garbage. We just let this guy spew out his bile every week and somehow it lasted 6 months. He promised us the world and he delivered under $10,000 for us. It was pretty pathetic compared to his promises. We held on to him way longer than we should have. But here’s the thing. We learned our lesson. Granted it was a $60,000 lesson but we still learned it. We never liked this guy from the beginning. This simply affirmed that hunch. It taught us about planning, trust, knowing when to cut someone off, having higher standards. The amount of invaluable information we gathered from this 6 months was worth way more than $60,000 and it’s not even close. Of course we were pissed, but that’s just the immediate reaction. Long-term reaction? 100 times smarter and 100 times more rigorous when deciding if we’d ever work with someone.
Know when to fold ’em
So that first story had to do with an investment of money that didn’t pay off. This one has to do with an investment of time and mental energy. It’s something that I think every single one of us can relate to. Amazingly, this story has to do with my own father and his business. I want to begin by saying I have a great relationship with my dad. I always have, and I suspect I always will. We are, however, in very different lines of work. My father is a psychotherapist (as was my mother). He’s been doing it for over 40 years. And in all of those 40 years my dad’s never gotten technologically savvy. The guy still doesn’t use a computer for his work. He literally has file folders upon file folders. Personally, I respect it. If the system still works, why break it? But even my dad knew some years ago he’d have to have an online presence.
So a couple of years ago my dad approached me about building a website for himself. While I may own a bunch of websites, that doesn’t mean I know a hell of a lot about building them, but it’s a safe bet I know more than my dad does. I told my dad I’d be happy to help. He’s asking me all kinds of questions, etc etc. I tell him it’s best he just sets up a simple site. But let me tell you how things went down. We’d have a conversation, he’d get all pumped, and then we wouldn’t talk again for weeks. Then one day we’d sit down again and he’d say that he needs a website. Conversation ends. Weeks go by. Same shit. This happened on and off for at least a year. Nothing happened. I mean nothing. Finally one day I just say to my dad, “I’m done, if you need my help you know where to find me but I’m not getting involved in this anymore.” And I stuck to my guns.
We’ve all had this in our lives. Things that for one reason or another fade. There’s just not enough interest or commitment on one side. But what’s significant about this particular situation was that I decided right then and there that I’d ever allow it to happen again. What I allowed was for me to chase after something that never really existed: commitment from my dad. When I look at myself honestly, my business is doing well and things are fine. I don’t need to be chasing everything and if there’s one thing I know, I can do things my damn self. If someone wants access to my brain and to my help, they’ve got it, but I’m not offering it anymore. It’s that simple. And if I need help? I’m more than happy to seek it out, but the moment I sense hesitation on the other side? I’m moving on. It’s that simple. And I don’t give a shit if it’s my own family.
Since that “breakup” which was a few years ago, things have been great with me and my dad. Not that they were ever even bad, but I had this cloud over me that I had to work with my dad. That I had to help him. No. There’s gotta be effort on both sides but in this case the effort needed to come from him, not me. My father understood this clearly and never put up a fuss about it. And I make this very clear with anyone I’m either in business with or have a relationship with. I just don’t have time for a lack of reciprocation anymore. Life’s too short.
You don’t have to be an optimist
Believe me, I’m definitely not a “glass half full” kind of a guy. Owning up to something doesn’t mean you have to see the good in it. It doesn’t even mean you have to feel good about it. It just means you have to accept it and God forbid even learn from it. In the two examples I gave you I learned to accept things I won’t tolerate and reminded myself to never allow those things into my life. On the flip side there are plenty of feelings that I’ve enjoyed and thought to myself, “more please.” That’s all life really is. Veering towards what you want and staying away from what you don’t. Every day and every experience should get you closer to whatever path you desire.