Tag Archives: risk

On fear, entrepreneurship, and wealth: Felix Dennis

Felix Dennis who comes from humble beginnings:

An art college drop out, Dennis left home before his sixteenth birthday, and lived in a number of bedsits. Dennis started his career in publishing with Oz magazine, the Sixties counterculture magazine, initially as a successful seller, through which editor Richard Neville realized Dennis’ potential business acumen. Dennis had earlier contributed to a television discussion on the counterculture, which Oz reprinted; the first magazines Dennis sold had been Neville’s only available means of compensating him for using this material.

Oz was prosecuted for obscenity in 1971. All three editors were found guilty of corrupting children, and given jail terms with hard labour, although Dennis himself was given a shorter sentence because the judge, Justice Michael Argyle, considered Dennis “very much less intelligent” — and therefore less responsible — than his co-accused. It was such a cutting remark that it allegedly drove Dennis to create a business empire to prove the judge wrong.

Revenge empire? Interesting, if true.

Some quotes from this article, which somehow manages to be simultaneously annoying, enlightening, and heartening. Probably quite a bit like Dennis himself, if his writing is a window into who he is as a person.

The key, I think, is confidence. Confidence and an unshakeable belief it can be done and that you are the one to do it.

Tunnel vision helps. Being a bit of a shit helps. A thick skin helps. Stamina is crucial, as is a capacity to work so hard that your best friends mock you, your lovers despair and the rest of your acquaintances watch furtively from the sidelines, half in awe and half in contempt.


If you wish to be rich, however, you must grow a carapace. A mental armour. Not so thick as to blind you to well-constructed criticism and advice, especially from those you trust. Nor so thick as to cut you off from friends and family. But thick enough to shrug off the inevitable sniggering and malicious mockery that will follow your inevitable failures. Not to mention the poorly hidden envy that will accompany your eventual success.

Consider carefully this shortlist:

  • If you are unwilling to fail, sometimes publicly, and even catastrophically, you stand little chance of ever getting rich.
  • If you care what the neighbours think, you will never get rich.
  • If you cannot bear the thought of causing worry to your family, spouse or lover while you plough a lonely, dangerous road rather than taking the safe option of a regular job, you will never get rich.
  • If you have artistic inclinations and fear that the search for wealth will coarsen such talents, you will never get rich. (Because your fear, in this instance, is well justified.)
  • If you are not prepared to work longer hours than almost anyone you know, despite the jibes of colleagues and friends, you are unlikely to get rich.
  • If you cannot convince yourself that you are “good enough” to be rich, you will never get rich.
  • If you cannot treat your quest to get rich as a game, you will never be rich.
  • If you cannot face up to your fear of failure, you will never be rich.

On risk: Ann Winblad

Ann is the co-founder of Hummer Winblad Venture Partners which opened its doors in 1989. It was the first VC firm to focus exclusively on software. Since that time, 45 of its portfolio companies have been acquired or gone public. She began her career as a systems programmer at the Federal Reserve Bank. In 1976 Ann co-founded Open Systems, Inc., a top selling accounting software company, with a $500 investment. She operated Open Systems profitably for six years and then sold it for over $15 million.

$15 million in 1982 dollars is worth approximately $50 million today using GPD per capita measure, which is the appropriate metric for this kind of thing.

From page 299 of Founders at Work: Stories of Startups’ Early Days:

When I went there, it was the first real business experience I had — although I had had part time jobs. I’d never been in a corporation, and it felt so glamorous to have a cubicle. Minneapolis is a bright city. There’s the Nicollet Mall and you were right downtown in the city. It’s like getting a job in San Francisco.

But it just wasn’t inspiring. No one was chomping at the bit. I actually can’t remember — I knew I was going to quit, but I can’t remember the moment where I thought, “I’ll quit and start a company.” I still felt very empowered, like, “This isn’t this hard a job. This is a big job and I’ve already gotten promoted once in the first 3 months and I know I can earn money. I can always come back to this, so why don’t I break out?” So the three guys from the Federal Reserve that started the company with me — one guy did quit his job and the other two took a year sabbatical, just in case this didn’t work. They held on to the safety ring.

There were not a bunch of people saying, “Start a company, start a company. Let’s do this. Let’s build something from scratch.” It’s so long ago now that I just remember the general feeling that there was very little to risk. I was somehow already fully trained for anything that might confront me. Of course, all that is false; there’s a lot of risk and you are never fully equipped to… you just have to be very adaptable. It turned out that I was adaptable. I didn’t know that until I did that, but it was just a feeling of fearlessness. “What’s the risk? What will I have to lose? I’m sure I can do this.” It was not cockiness, just that moment you feel in your youthfulness that you are sort of empowered to achieve.

I think what does separate some entrepreneurs from other entrepreneurs is we’re not handwringers. We don’t worry about the unknown. We don’t really worry about the risk points ahead. As you get older and you get more experience, you train yourself to think ahead about the risk points versus just to take the next hill. But non-risk-takers and non-entrepreneurs would have really big headaches about this. They would need some level of comfort and safety.

That’s something that we look for in entrepreneurs — that they have the courage to do the job. That they’ll have the ability to judge the business situation. They’ll have the ability to lead people. They’ll have the ability to interact with the marketplace and to really build confidence into strategy.

On risk: Paul Graham

I’ve been doing a lot of reading lately, and today I was reading “Hiring is obsolete” by Paul Graham. I loved it, and the section on risk really stood out to me, and I’d like to highlight some specific bits.

So what you should invest in depends on how soon you need the money. If you’re young, you should take the riskiest investments you can find.

All this talk about investing may seem very theoretical. Most undergrads probably have more debts than assets. They may feel they have nothing to invest. But that’s not true: they have their time to invest, and the same rule about risk applies there. Your early twenties are exactly the time to take insane career risks.

The reason risk is always proportionate to reward is that market forces make it so. People will pay extra for stability. So if you choose stability– by buying bonds, or by going to work for a big company– it’s going to cost you.

Riskier career moves pay better on average, because there is less demand for them. Extreme choices like starting a startup are so frightening that most people won’t even try. So you don’t end up having as much competition as you might expect, considering the prizes at stake.

But it’s not necessarily a mistake to try something that has a 90% chance of failing, if you can afford the risk. Failing at 40, when you have a family to support, could be serious. But if you fail at 22, so what? If you try to start a startup right out of college and it tanks, you’ll end up at 23 broke and a lot smarter. Which, if you think about it, is roughly what you hope to get from a graduate program.

Even if your startup does tank, you won’t harm your prospects with employers. To make sure I asked some friends who work for big companies. I asked managers at Yahoo, Google, Amazon, Cisco and Microsoft how they’d feel about two candidates, both 24, with equal ability, one who’d tried to start a startup that tanked, and another who’d spent the two years since college working as a developer at a big company. Every one responded that they’d prefer the guy who’d tried to start his own company. Zod Nazem, who’s in charge of engineering at Yahoo, said:

I actually put more value on the guy with the failed startup. And you can quote me!

So there you have it. Want to get hired by Yahoo? Start your own company.

The entire essay is absolutely worth reading for anyone interested in starting their own business.