The Secret to Being Very, Very Rich

Paul Ollinger
4 min readAug 25, 2023

Few people have what it takes

“Don’t confuse desire with compulsion.” — Felix Dennis

If you want to be rich, you have to be unreasonable. You have to do things outside the realm of practicality, safety, and politeness. Because to earn vast wealth, you must be compulsively driven toward that singular goal. Nothing else matters.

So claimed Felix Dennis, the late founder of Maxim magazine and Dennis Publishing, in his book How to Get Rich. Dennis doesn’t come at the subject with the typical guidance of other “get rich” authors, almost none of whom enjoys a net worth anywhere near the £400mm Dennis had earned when he published his guide in 2008 (when the GBP was double its current value).

Perhaps that’s why Dennis’ advice feels so savagely authentic. Instead of preaching about dollar-cost-averaging or portfolio diversification, Dennis offers the reader unvarnished insights into building and preserving ownership of a company, aka the only way to go from zero to very rich unless you can monetize your talents like Tom Brady, Taylor Swift, or J.K. Rowling.

As Dennis demonstrates through dozens of anecdotes, maintaining control of any entity worth controlling will drive you beyond the brink of reasonability time and time again. And so he comes to one of his main rules for success: Don’t confuse desire with compulsion. Sure, everybody wants to have a lot of money, but very few people are willing or able to do whatever the hell it takes to fulfill that vision.

Felix Dennis, founder of Maxim Magazine

Being unreasonably compulsive starts with resisting the siren song of a salaried career. Working for someone else — even in the C-suite — might make you very comfortable, but it won’t make you very rich, which he defines as starting around $100 million in liquid assets. Forsaking life as an employee might sound easy, but try turning down a predictable income when you’re living in squalor, and your very patient girlfriend is threatening to walk.

Even if you’re down for this precarious path, you still need an idea that has the potential to grow into a thriving business and the moxie to get the ball rolling. Then you have to go out into the world with the thickest of skins and walk the “narrow, lonely road to get the capital to make it so,” an experience that Dennis found plagued with desperation and vultures.

But our hero’s journey has only just begun. Beyond this, Dennis says, a founder must refuse to give in. You can’t crumble when creditors have you by the bollocks. You must not fold when key employees conspire to wrest away a piece of your enterprise. You have to scrap, improvise, and cajole to make payroll when cash flows trickle. You’ve got to resist the tempting lucre when private equity guys make a juicy offer for 51% of your venture. In short, you positively, absolutely must maintain control, no matter what.

All of this will take a profound toll on your personal life because if you want to achieve mega-wealth, work must trump relationships every single time. “Any distraction whatever can cost you a chance that may not come again,” Dennis explains. “And, for the purposes of this book, family, lovers, and friends are distractions. Plain and simple.”

It made me wonder whether being a billionaire also requires you to be an asshole. I don’t think so, but it seems clear that you need to be willing to have others call you an asshole. Being unreasonably committed to achieving your goals means foregoing a conventional lifestyle and saying no when “good manners” would suggest saying yes.

This will provide ample evidence to others with relatively mediocre financial results that your gains are ill-gotten. 99.8% of people — me very much included — can’t wrap their minds around the monomaniacal focus required to succeed at this scale. And because it’s harder to accept reality than to rationalize this yawning success chasm, expect others to disparage your character, question your commitment to your children, suggest you broke the law or took advantage of others to rise to such heights.

Yes, if you want to be very rich, you’ll need to be okay with people talking shit about you behind your back, to your face, on social media, and in the press. Because once it’s clear you will become crazy wealthy, you also become an inhuman circus freak onto whom others project their insecurities and the bourgeois values to which they are suddenly so committed. There’s no better example of this than the politicians and activists who chant, “Billionaires should not exist.”

Pondering Dennis’ words helps me put my own situation into perspective. Had I stayed in the technology industry for another five years, I probably would have made it to the nine-figure club. But I wasn’t sufficiently unreasonable. I wasn’t having fun; I didn’t want to work so hard; I wanted to help care for my aging parents and to give comedy a full swing. These are all very understandable, very reasonable goals that perfectly demonstrate the difference between desire and compulsion.

So when I find myself coveting the trappings of the super-rich or thinking snarky thoughts about Messrs. Musk or Bezos, I try to remember that their stratospheric success in no way diminishes the work I’ve done or the choices I’ve made. They picked an unreasonable path and reaped unreasonable rewards. Good for them.

Felix Dennis would be proud.

--

--

Paul Ollinger

Comedian. Host of the Crazy Money podcast. Proud former Facebook and Yahoo! sales person/leader. http://PaulOllinger.com/podcast