The 7 Deadly Sins of Startups

1. Wrath | Without Action

In life, wrath is generally bad, but while starting up a business wrath can be a great motivator – if paired with action. Wrath can come from getting spit on your whole life, feeling unhappy or being told you can’t do something. This creates righteous wrath, I’ve often experienced it myself (most recent was direct at these rat bastards.) The thing that will cripple you is allowing that wrath to occur and then not acting on it.


  • Wrath: Argh, why can’t people gather together to get better deals on products/services… Action:
  • Wrath: There are no good men in this city who are professional like me … Action: It’s Just Lunch
  • Wrath: Why can’t would be entrepreneurs in other countries get the money they need to help them make their situation better… Action:

2. Greed | With No End Point

You almost have to be a little greedy, at first, when you start up your own business. You ought to have grand ideas about what the world will look like when you crush your enemies, build the next Facebook and never have to work another day in your life.

But remember to always know your number (exit $$) or even better have a clear idea of the end goal. What will ruin you and possibly your start up is doing it only for money or material gain, 9 times out of 10 the most successful businesses and people are motivated by things greater than cash, be it revenge, true love or changing the world for the better. So have a monetary goal you want to meet with each endeavor and a larger goal (this gets me closer to proposing to Denise, this will allow me to go on missions to Africa, this will change the way the world communicates online).

Greed, for the sake of greed will debilitate your business and one day you’ll turn down a massive opportunity in search of ‘more’ and you’ll realize later that it was the last train out.

3. Sloth | The Curse of Good Enough

I’ll be perfectly honestly with you, this is the n. 1 startup sin I struggle with. I’m not sure if it’s genetic or I’m just a really lazy bastard, but I constantly fight my inner fat-guy-on-a-couch whenever I’m trying to start something or reach extraordinary lengths.

The reason that the popular axiom of “5% of the population holds 95% of the wealth” is mostly because they didn’t settle for good enough. So when you start to feel yourself getting lazy, when  you feel yourself starting to quit before it really hurts (or pushes you far beyond your comfort zone) – don’t do it. Keep going, push on until you surprise yourself.

Being ‘good enough’ is never good enough if you want to start a business that will change your life and reach extraordinary heights.

4. Pride | Before and After You’ve Earned It

Nothing annoys me more than people that act bigger than their britches and nothing is a better marker of a sure fire sinking ship. People who are prideful, arrogant and full of themselves in business will likely fail in an extravagant and embarrassing way.

Everyone is the same, more or less. If you learn this lesson and treat the guy who washes your car the same as the head of Sony you’ll go far in life. Don’t ever think you aren’t good enough for someone and never think you’re too good for another. In my youth I learned this the hard way, now I strive to treat everyone the same and I want to actually get more humble with success vs. the other way around.

5. Lust | For Another’s Business Model

“Daaaaaamn…. did you check out the cash on that business model?”. That happens all too often when new start up entrepreneurs hear of other’s successes… they become envious of other people’s business model and get suckered into the notion that all they have to do to make $23,000 like Pat Flynn is to just copy him.

NO. That’s wrong! You’re envying and you’re committing a mortal and start up crushing sin. Pat got to where he is by BEING different, he has innovated, led and taught. You can pay homage to his efforts, you can follow his advice but you cannot reach those same heights by just lusting after his business model & not trying to innovate your own.

People who do well get there because they do something different, they try harder, work longer or are smarter. Copying someone elses business model outright just doesn’t work – look at all the Fiverr clones if you don’t believe me.

6. Envy | Keeping up with the Facebook’s

Ever hear of “keeping up with the Joneses'”? Startups are especially plagued with this deadly sin but instead of merely trying to keep up with a flashy neighbor they try to outdo Twitter or live like Tim Ferriss before they’ve put in the hard work that earned them that right.

While you’re starting up keep costs desperately low, pay yourself in ramen and hostel it while traveling. Don’t try to put on airs and “trick” people into thinking you are more successful than you are. This will bite you in the butt – promise. Plus when you envy you lose precious time and energy you could be using to make your business better, never think about another’s startup when you could be using that time to dwell on helping yours succeed.

7. Gluttony | Don’t Over Indulge on Ideas

Are you an idea glutton? I am, or at least, I used to be. I would fill up with wonderful, amazing ideas for business, projects and start ups – then I would try to execute on all of them at once.

Gluttony in startup-ville is not being laser focused on a project and instead chasing down several different paths like so many zig-zaggy butterflies. This. Will. Kill. You.

I have fallen into this pit more times than I can count. I like to pontificate it’s because us entrepreneurs like to think that every idea we have is so brilliant it would be a crime not to share it with the world – but that is hardly the case and often when you try to do more than one thing at a time you lose momentum and all the spinning plates come crashing down.

If you want to build a successful startup, business or blog – focus on just that – one at a time.

If you’re suffering from one of the above…

Feel free to check out my business coaching. In 2010 I was so happy to get a flood of emails and letters from people who I’d helped via consulting and I want to do the same for anyone else who is out there and in need of some guidance.

**Bonus points for anyone who can name the partial painting featured in this post