Losing more than a million dollars

Let me tell you about the best mistake I ever made. To view this email as a web page, [click here]() Why I try to fail Let me tell you about the best mistake I ever made. [My mom and me at graduation] My mom and me at graduation When I was in high school, my parents told me that if I wanted to go to college, I'd need to pay for it with scholarships. So like a good Indian son, I started applying ... and applying and applying. In the end, I applied for about 60 scholarships and won hundreds of thousands of dollars. The best scholarship I received was the first one — an award for $2,000. The organization wrote a check directly to me. I was thrilled! And since it was 1999/2000, like everyone else, I thought I was a genius. So I took it and invested it in the stock market … and immediately lost half my money. Oops! There is a happy ending to my story. I call that loss the best mistake I ever made because while I lost that money, it did spark my interest in personal finance — and led to me starting IWT. Over the years, I’ve had dozens of failures like this. I want to share a couple more. As you read, see if you can figure out what these failures have in common. Losing more than $1 millionA few years ago, I spent $2,000,000 to make $793,084 — in other words, I lost over $1 million. And that $2 million doesn’t even include the cost of building the team of copywriters, designers, and a data analyst. I got impatient with our subscriber growth. We were growing steadily, but I wanted to go faster. I got jealous of all the numbers I saw being thrown around, like people getting 10,000 new subscribers a week, spending a dollar and making two, making $3k profit every day, and so on. I worried I was missing out on the next big thing. So I decided I had to find out how they were doing it. This is where (1) being jealous and (2) having the money to execute becomes a dangerous combination. Basically, we spent a shitload of time and money (and we got really good) at all of these strategies to grow faster. [Optimization Team] When our analyst called a special meeting and started slide 2 with “Unfortunately…” I knew we were in trouble. Yes, the numbers looked good on the surface. Some of the strategies made us money, even a decent amount. Unfortunately, none of these new strategies beat the system we’d already built over the last five years. Not even close. Yes, traffic was at an all-time high. Yes, we’d been able to dramatically scale our number of email subscribers. Unfortunately, most of the new subscribers never bought a thing! That sinking feeling was me realizing we’d made a huge mistake. All those damn gurus, all those rumors I’d followed … when you actually run the numbers, a lot of them don’t pan out. We paid millions to learn that we need buyers, not subscribers. Spending hundreds — but ending up with NeutrogenaI like to try tiny experiments to see what I care about. It’s one way I continue to refine my [Money Dials](). Recently, I tried a bunch of expensive skin creams and shampoos and realized that none of them made a difference for me at all. Great! That cost me a few hundred bucks and now I can happily buy Neutrogena for the rest of my life. * * * OK, enough of my failures or I’m going to start crying. Looking back at the stories I shared, what do you notice? Here’s something I notice: These failures both served as tests. I tried something, it didn’t work, and I learned from it. I put it behind me and moved on, though sometimes that process took longer in some tests than others. The way I think about testing is that I’m going to get the opportunity to do certain things many, many times in my life. I want to find the best possible answer, the best possible route home, the best possible solution. I could sit back and think I’m the smartest person in the world, that I know exactly how to craft that perfect answer, or that perfect headline, or that perfect design. Or I can be humble enough to say, “You know what? I probably don’t know the answer. I think I have a rough sense. I could probably choose three different options, but I have no idea which one is going to work or not.” To me it boggles the mind that many of us go our entire lives not testing things we do every single day. What we wear, the route we take to get home, the number of hours we sleep, different ways to motivate ourselves to get to the gym. Why do people do this? Because they don’t have this testing mentality. They’re afraid of failing, which is ironic because they are already failing by not testing. Trial and error is necessary. I really believe in making more mistakes, and learning faster, than anyone else. 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