The 7 Cardinal Sins of Startup Founders

Cardinal Sin #1: Delusions of Grandeur

The worst kind of founder is one who thinks they are the second coming of Christ. NO, your company isn’t going to be worth billions. NO, your idea won’t change the world and feed the poor or stop climate change or bring peace to the Middle East or save the fucking whales. NO, your idea isn’t the next “Uber” or “Airbnb” of this or that.

In reality, your idea has as much merit as a Justin Bieber love potion or a testicle scratcher.

Just remember: you and your startup are not hot shit until it’s actually hot shit.

What you should do instead:

Leave your ego at the door and be prepared because I have a ridiculously oversized revolver that I am ready to use. And if you send me a bad pitch, you better hope I use it on myself first before I can use it on you. And if you somehow managed to dupe another VC to invest in you, remind me to shoot them instead.

Cardinal Sin #2: Being A Phony

I hate suck ups. I always get ambiguous emails from people who read my articles and it somehow magically changed their life enough to “reach out” to me. But it always turns out to be a bunch of BS because what they really want is my money. I can’t stand it when people beat around the bush about wanting funding because unclear intentions are a waste of my time.

There are dozens of articles that tell entrepreneurs to commiserate or praise in order to build rapport with VC’s, but that’s just awful advice because I already know all the tricks in the book. This isn’t a god damn high school romance where you are being shy and stuffing love notes in your crush’s locker.

What you should do instead:

Just stop being such a sycophant and grow some balls. Tell me about your startup and that you need funding. Just be straight with me and I will do the same.

Cardinal Sin #3: Not Paying Attention

If you look at my contact page, I have 3 simple steps that I require all founders sending me pitches to follow. There’s a problem though: out of the hundreds of email pitches I get every week, I have yet to receive one from someone who followed every single instruction.

You ask for a short pitch but get the National fucking Archive instead.

News flash: adding more words to your email won’t make you or your startup sound any better and it sure as hell won’t help convince me to give you my money.

If anything, I am deeply insulted every time this happens.


? Because it shows me that you don’t respect my intelligence. It’s almost as if you are saying “my guidelines are obviously better than yours so I’m going to send you this pitch MY WAY and ignore everything you said”.

I am not trying to be some kind of pitch nazi here but there is a good reason why I put these guidelines in place; I get too many emails. Time is a valuable commodity and I rather use it to focus on, oh gee, I dunno, STARTUPS THAT DON’T ACTUALLY SUCK???!

Besides obvious time constraints, the thing that also buggers me is the fact that you don’t care enough to read and listen. If you can’t listen to me, how will you be able to listen to your customers? What about your board? Your inability to listen makes me wonder about your character and how capable you are of being a CEO/leader.

Cardinal Sin #4: Growth hacking and Getting Sassy with SaaSing

I can’t stand buzzwords – it’s almost as if founders are purposely trying to confuse the fuck out of me in order to trick me into investing in their fancy tech startup.


For the record, I am as tech savvy as the next guy but my croc brain just can’t register all that techie terminology. If you can’t even tell me in plain English what your startup does, how the hell are you going to explain it to your laymen customers?

What you should do instead:

Pretend you are talking with a simpleton (which shouldn’t be too hard because most VC’s are “simple”) and speak more slowwwly in order for the investor to understand.

Cardinal Sin #5: Moving too fast

One thing that drives me nuts is when founders try to get a meeting with me or to talk on the phone without even fully pitching their idea to me first. Listen, I am all for hearing your ideas but only if I can see the initial value in them or else my schedule would be swamped with useless meetings.

I am not some kind of floosie investor either; you gotta wine and dine me first before I considering hopping in the sack with you.

Besides, if you can’t grab my attention in the first email, there is no way you can do it in real life or on the phone. Oh and by the way, your crappy startup won’t somehow magically sound better in person or on the phone even if you happen to have a confidently smooth Morgan Freeman type voice.

What’s even worse is that sometimes I get emails from random business people who just want to “meet”. But for all I know, you could be a Chinese organ thief or serial rapist so for the sake of my genitalia and precious kidneys, I won’t take a meeting with you especially when I don’t know what the context is.

What you should do instead:

You really have to approach VC’s the same way you would approach a cute girl at a bar. Be confident but non-invasive. Be professional and make your intentions clear.

Cardinal Sin #6: Fudging the numbers

When founders present questionable numbers or data to me, I usually assume 2 things:

1. You are a product of the US education system and failed spectacularly at math.

2. You are a numbers weasel who is deliberately trying to fudge the numbers to make your startup seem better than it really is.

I can’t speak for all VC’s but I obsessively fact check. And it’s not just a simple Google search either because unlike lazy startup founders, I know how to READ. I will dig up studies and read them from top to bottom. I will even email the people who made the studies to double check the numbers.

If you have even one number that is off, I will know.

Cardinal Sin #7: Being a sheep

Out of all the cardinal sins I’ve listed so far, this is probably the most egregious. What makes it really insidious is that startup founders don’t even know that it’s happening.

Think about it: how many startups out there are doing truly disruptive and unique things? I’ve seen too many startups being created off the backs of other ones – old ideas being recreated into supposedly “new and innovative” ones.

Oh sure, you got that ONE fancy feature that the other guy doesn’t have, but is that suppose to make a difference? Is that suppose to compel me to fork over millions of my dollars to fund an idea that came from the same stinking heap pile of perpetual craptitude?

There is no more creativity now. No more outlandish ideas and remarkability, no new ways of looking at things.

Startups can’t even come up with good startup names because they are content with doing whatever the hell everyone is doing. And how many startup websites have you come across that look exactly the same?

For a industry that prides itself on funding “disruption” and innovation, it’s become increasingly difficult to see any evidence of that.