If you are a fan of audiobooks, as I am, then I highly recommend you purchase economist and podcaster Malcolm Gladwell’s new offering, “The Bomber Mafia“. This is a new audiobook that was conceived and designed to be an audiobook, and not just someone reading a print book into a microphone. In the audiobook there are sound effects (such as exploding bombs), music, and recordings from the World War II era that is the subject of the book. Even if you aren’t that interested in the subject – bombing during WW II – you should still buy the book just to listen to the production, if you like audiobooks.

Author Malcolm Gladwell


At the outset of “The Bomber Mafia”, Gladwell says he has come to the realization that he likes to write about people who are Obsessives. Obsessive people, Gladwell says, are those who are able to block out all of the external noise and distractions in order to move forward with an idea or a goal that they believe will change the world in some way. While obsessive people may accomplish a great deal, their accomplishments will likely be at the expense of interpersonal relationships. Obsessives typically aren’t great managers of people or even life partners because even the people closest to them can get in the way of their obsessions. People who are obsessive typically aren’t fully healthy, either mentally or in some other way.

Are You Obsessive?

Most people aren’t obsessive, and that is probably a good thing for greater society. Can you imagine what our society would be like if most people were obsessed about something? And what if those obsessions came in conflict with one another? I guess that’s how wars start. So, if you are lacking an obsession, that’s ok. However, you may want to look at the concept of obsession as a way to invest your money.

Entrepreneurs Are Obsessives

I would guess that many, but not all, successful companies are started and run by obsessive entrepreneurs who believe they can change the world and want to convince a pack of employees to engage in the quest to do so. Think about the mega-cap companies that are now the most valuable in the world. Do you agree that Bill Gates of Microsoft, Steve Jobs of Apple, Mark Zuckerberg of Facebook, Elon Musk of Tesla, and Bezos of Amazon are or were obsessives with their visions for their respective companies? Most, if not all, did not let interpersonal issues get in the way of their obsessions. Most were considered to be not very nice guys. However, the world wouldn’t be what it is today without any one of them, and our economy wouldn’t have gotten through the pandemic as well as it did without what they have contributed to our economy.

Look For Obsessives

With respect to your own investing, we have been taught by the Warren Buffetts of the world (another obsessive!) that we need to dig deep into the companies, their markets, and their financials in order to make a fundamental decision as to whether or not to invest in those companies. This is all well and good, but I would also add that you need also to look to see that the leadership of that company is obsessed about its mission. This is probably easier to do with larger companies because these larger companies tend to get more press coverage. However, if you like to dabble in mini-cap stocks or even in private equity or private companies, I would make sure that whoever is leading that company has a reasonable and healthy obsession with whatever that company is trying to accomplish. I would guess that most such entrepreneurs will be obsessed to some level. Now it is up to you, the investor, to determine if their obsession can be realized and monetized, and if that entrepreneur is the one who can lead that company to greatness. After all, there have been a lot of obsessed people who have failed either with their vision or their execution. You need to place your money not just with an obsessive, but with one who is able to bring their vision to fruition and make money for their investors in the process. This is what makes investing, or the allocation of capital, such an interesting endeavor.


You don’t have to be obsessive yourself in order to invest in people’s obsessions. If you look top-down at corporate management and determine whether their vision of their mission and their ability to execute it is within reason, then a good part of the battle for you as an investor is won. Building a successful company can be ugly at times but an intense focus on that building process is what is needed for that success. Look for those types of people when you invest your money.