An Open Letter to the Venture Capital Community

Every day since the first of my Don't Be a Fucking Douchebag series was posted, folks have asked me what my plan is to change the increasingly douche-y culture of the startup ecosystem.

Now... to be clear, I don't believe there is any way to turn back now. The past is the past - we cannot return (no matter how hard some politicians might try). I do, however, believe that we can affect the direction we are heading. We might not be able to return to the past - but we can impact where we end up in the future.

In looking at how we got to this awful place, it's pretty clear that one of the easiest ways to impact behavior is going to be through the investors. The big pots of money out here attracted stacks of asshats. And some of them were successful - but even if not successful they were not punished for their general douchebaggery.

And entrepreneurs noticed.
And aped these behaviors - knowing there was no downside.

So how do we change our course?

By punishing startup douchebags.

And how do we punish startup douchebags?

By denying them money.

Because these douchebags are like dung beetles... take away the shit they crave and they'll go somewhere else, looking for another source.


So this is my plea to those investing in technology startups in general - and to Venture Capitalists in particular.

Please stop giving money to douchebags.

Listen... I know you're under pressure from the LPs, and that they only care about returns.
But do you REALLY want to be on a BOD with these fuckers? Life is pretty damn short for that...
I know a lot of you talk about pushing a "no assholes" rule for your portfolio companies. How about you apply this to your own investment decision-making?

And here's the thing... if you stop giving the true douchebags money, the "followers" will stop emulating them. Because you won't be funding the assholes. Which means you'll be dealing with fewer douchebags - while still seeing comparable dealflow.

And at night you'll go home knowing that you've done a little bit to help the world.
You've done a little bit to stem the tide.
And if you do your part - I think it's gonna be that first domino.

We can do this - and YOU can lead us.

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Don't Be a Fucking Douchebag Part Three

This is part three in a three part series on not being a fucking douchebag. You should obviously start with Part One (Choose Your Role Models).

Part Three - Douchebags Like You are Ruining San Francisco

My Mea Culpa: I know that it’s people like me that started this shit show in SF. I moved to The Mission back in the early 90s. I was part of the gentrification that started the whole trend of startups being centered in this neighborhood. I sold a company at the height of the dot-com boom and I did my part to turn SF into the playground for the rich and educated that it’s become. I accept my portion of the blame - and am now trying to do what I can to stop things from getting worse and perhaps even get just a little bit better.

I moved to San Francisco in 1992. I was looking for a job - but I was also looking for a new life and a place that had hope and excitement and which provided a bigger, wider and more diverse world to play in. I found a city made up of wildly different people - of all types - spread across a huge range of little tribal neighborhoods. It was a massive melting pot of values, ethnicities, world views, ages and economic classes.

I fell in love with the city immediately. It was a place for experimentation and reinvention.

During the dot-com boom, the city started to lose some of its soul. Greed started to rule, and the city started to become more and more expensive. The weird craziness started to slip away. Experimentation and reinvention began to vanish as the cost of living in the city became prohibitive for artists and dreamers and anyone who didn’t work in tech.

After the crash, the city recovered a little. We started seeing diversity return. People began to experiment again. Maybe there was no more Red Man, but at least we had Bum Jovi.

And it wasn’t just about the money - for a while.

But now... Now it’s worse than it was in 2000. Now it’s only about the money. Now the only diversity we have left is ethnic diversity. Everyone is rich and privileged and entitled or hustling as hard as they can to become rich and privileged and entitled. A city once defined by people wanting to change the world is now defined by people who just want to be among the world’s richest. A culture that once understood history and tried to create it now has a memory that’s about 2 fiscal quarters long - and a vision that goes as far out as their funding allows.

San Francisco used to be weird. And we were proud of that. Now it's shockingly vanilla and suburban and conformist. It once felt like a city. Now it feels like a suburb.
And that's sad.

Some examples of what it’s like here now:

• if you make $70k a year you’re likely spending half your income on rent.
• you walk down the street and overhear someone saying, “my father had some tax thing so he bought a unit in the top of the Millenium Tower. It’s super cool because this way I don’t need to get a job and can focus on my Google Glass app.”
• you see a standard 2 bedroom, 2nd floor Edwardian flat in the Mission listed for $7500 a month - and then find out that some entrepreneur offered the landlord $8000 a month sight unseen.
• you’re on MUNI and watch a 20 something guy reluctantly give up his seat to an elderly woman and then say loudly to his friends, “I don’t know why old people ride MUNI. If I were old I’d just take Uber.”
• at least 10 times a day you want to murder random people in public because of the fucking stupid shit they say or the horrible ways they act.

And you know... I really wouldn’t mind so much if this was happening in NYC. There is a cultural norm in NYC that supports this kind of douchebaggery. But this is San Francisco. And San Francisco is a special place.

And you’re fucking ruining it.

Nowhere is this more obvious than in The Mission.

When I moved to this neighborhood 20 years ago, I chose it because it was cheap, convenient for someone without a car, and because it wasn’t one of the three neighborhoods I knew I didn’t want to live in. I’d looked around the city and realized that I didn’t want to live in North Beach (drunken frat boys), or the Marina (drunken frat boys and drunken sorority girls) or Noe Valley (stroller brigade). I couldn’t afford to live up in Pacific Heights (and couldn’t cope with the snobbery).

So in the end, The Mission was the answer.

And I found I loved it!

It was an entirely different culture for me - and one that was strong, vibrant and had a deep history and set of values. It was fun and funky and foreign and incredibly cool.

I learned about the history. I learned about the different ethnicities and nationalities that had made up the waves of immigration to the neighborhood. I learned passable menu spanish. I discovered the hidden history of streets like Bartlett and Capp and Shotwell.

I didn’t want to live anywhere else in the city and thought I’d live here as long as I stayed in San Francisco.

But now? Now I’m moving out.

The Mission these days is over-run with the exact same frat boys and sorority girls and mommy bloggers and snobbish rich kids that I moved here to avoid. More than that, however, The Mission is now infested with startup douchebags. You can’t go a fucking block without hearing about someone’s “funding party” or someone else’s “vesting schedule” or overhear a fucking verbal vomit love letter to Pando Daily.

The Mission is now more expensive than Cole Valley.

Last month my new neighbors (4 sorority girls who apparently all work in social media marketing) threw a Cinco de Mayo party complete with straw sombreros, blender margaritas and a lot of shouting of “yo quiero taco bell.” Fucking seriously.

So here is my request to all of you internet, startup, tech folks living in The Mission or thinking of moving to The Mission.

Don’t. Be. Fucking. Douchebags!

It’s really that simple.

Be considerate. That little old hispanic lady at the bus stop? Help her onto the bus instead of loudly bitching about how she’s going to make you late to your meeting at The Creamery.

Be respectful. This neighborhood was here before you and will be here after you leave. It’s not your trashcan, your toilet or your playground. Understand the history and the culture and the people and act in a manner that isn’t stupidly offensive.

Be sensitive. The traditional residents of this neighborhood are not rich and never will be. Flaunting your wealth and your opportunities is a douche move.

Just try to be a decent human being. Is that so much to ask?

As it is, I’ve had to start working hard to dress, look and act like I do not work in tech or startups when I’m out and about in the ‘hood. This way people still smile at me in the bodega, I still get to exchange jokes with folks waiting in line. I get to be treated like a human - not a fucking asshole.

So please... stop ruining it for the rest of us.

Because I love San Francisco. And I love The Mission. And as much as I’m starting to hate you all now - that will be nothing compared to how much I will fucking hate you if you ruin this.

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Don't Be a Fucking Douchebag Part Two

This is part two in a three part series on not being a fucking douchebag. You should read Part One (Choose Your Role Models) first.

Part Two - Confidence Doesn’t Mean What You Think It Means

Being an entrepreneur is a confidence game. “Fake it until you make it” is the rule. We all know that showing fear or doubt is often death and that you need to project a certain amount of irrational confidence to get you through the challenges along the way. Dealing with investors can feel a lot like confronting stray dogs on the street - you kind of know they can smell your fear so you act big, scary and most of all very, very assured.

But it seems like a lot of folks calling themselves entrepreneurs simply don’t understand what “Confidence” really means in this context. Because a lot of you are not acting confident - you’re just acting like fucking douchebags.

Let me explain in a very simple manner what I’m talking about.

Confidence is founded on knowledge, skill and understanding. To illustrate... I’m confident in my ability to taste and analyze flavors. This is based upon a decade working and training as a chef and 5 years spent working in speciality coffee. This is based upon tens of thousands of hours of practice. Does this mean I am right all the time? No... it doesn’t. But it means that I’m right a lot of the time - and when I’m wrong, I learn and my confidence grows.

In the current startup scene, what is being exhibited and displayed by many so-called entrepreneurs is not Confidence - but rather a toxic combination of Arrogance and Ignorance.

I hear a lot of startup folks talking shit about stuff they know nothing about - with a huge amount of delight in their own brilliance. When I question their knowledge, the usual answer tends to be a lot of dismissive talk about “disruption” and “useless old ways of doing things” and “applying startup models to other problems.” And this is seen (by them) as being Confident.

But here is the thing.... to those of us who actually know something about the topic this doesn’t come off as confidence at all - but rather as arrogance coupled with willful ignorance. And, frankly, that makes you look like a fucking douchebag.

So... you want to be a successful entrepreneur.
You understand that doing so requires a lot of confidence.

So fucking learn about the stuff you want to appear confident about. Don’t be lazy. Don’t be stupid. Don’t be arrogant and stop being fucking ignorant.

Do the fucking work.
This is not a game.

Because every fucking time you open your yap in public and start bleating dumbass shit about “disrupting the health insurance industry using Google Glass and Node” you make all the rest of us look bad. And you make folks like me who happen to overhear you want to punch you right in the fucking nuts.


Read Next - Part 3, Douchebags like you are ruining San Francisco

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Don't Be a Fucking Douchebag Part One

This is part one of a three part series. Yes... the issue really does demand it.
This part will cover role models for entrepreneurs. Part two will explore the difference between arrogance and confidence. Part three will discuss the ugliness of today’s San Francisco.

I’ve spent a decent chunk of my career working in agencies. Agencies are, of course, legendary for collecting difficult, annoying and often unpleasant personalities. But compared to what I’m seeing right now in the startup and entrepreneurial community, the vast majority of agency folks are deeply moral, highly sensitive and wonderfully considerate people who are a joy to be around.

Don’t get me wrong. I love working in startups. And for most of my career I’ve loved the kind of people that become entrepreneurs.

I’ve founded, run and/or worked at a half dozen startups over the last 20 years. And I live in San Francisco - in The Mission district in fact. So I’m surrounded by startup employees, entrepreneurs and wantrepreneurs galore and have been so for the last two decades of my life.

For the first time since moving here in 1992, I’ve recently found myself considering getting out. Wanting out of The Mission. Wanting out of San Francisco. And wanting out of startups. Not because I’m getting old (though I am). Not because I’m burnt out (at least not yet). Not because I’m rich (don’t I wish).

I’m tempted to get out because of the people I have to deal with and because of the people I have to associate with and be associated with.

Times have changed and the behavior, attitudes and personalities within the startup scene are no longer acceptable, tolerable or supportable. To put it bluntly... the startup community has become overrun with fucking douchebags. And it’s got to stop.

I’ll give various examples of douchebaggery throughout this series - but to help you understand what I mean by Douchebag I’ll simply point you to the behavior of today’s best example - Sean Parker.





Selfish. Arrogant. Greedy. Self-centered. Entitled. Insufferable. These are the words that describe a douchebag.

Do you talk loudly on public transit about doing Adderall in Las Vegas and going to a strip club and throwing hundred dollar bills around? You’re a douchebag.
Do you drive your SUV to Valencia on the weekend and unload your brand new fixie for a cruise up and down the street? You’re a douchebag.
Do you describe yourself, publicly, as a guru or a superstar? Douchebag.
Do you retweet any and all compliments tweeted about you? Do you tweet things like, “After flying the Gulfstream G500 I don’t know how you go back to the G4”? You, sir, are a fucking douchebag.

And I’m going to help you become a human again.

Part One - Choose Your Role Models Correctly (and learn how to model behavior)

The tech world has a long history of hugely successful leaders who are assholes. But frankly few of us in the past saw Larry Ellison (for example) as someone to model our behaviors on. Sure - many of us respected his accomplishments and even admired what he built. But actually trying to be the kind of person he is? Hell no.

These days, however, it seems like many of us are choosing role models who are total douchebags. It seems like we’re looking for role models based not on the kind of person they are (and the kind of person we want to be) as well as their success but rather simply based on their success (fame / fortune) alone.

So I have to ask - do you want to be an asshole? Is that why you’re choosing a role model who is an asshole?
Or do you just want to be a success? And if so... what price are you willing to pay for your success?
Are you like the Wall Street fuckers who, if choosing between making $1M where everyone wins or making $1M where everyone else loses, will always chose the option where others lose?
Or do you want to be a success while still being a decent human being?

Because if you want to be a success while not becoming a fucking asshole... there are role models for you to choose from who are successful and are good people. Reid Hastings (Netflix) is a great example. Thor Muller (co-founder of Get Satisfaction and author of “Get Lucky” is an example. Or Lisa Gansky (co-founder of GNN and Ofoto). Or Oren Michels (Mashery, Feedster, Winebid.com). Or Joe Chung (ATG, Redstar). Joshua Schacter, Andy Baio, the list goes on and on.... If you want role models on the investment side, there are great people to model on there as well. Like Bryce Roberts and Andy Weissman and Rob Hayes.

To sum up... if you cannot find a role model who is not an asshole - that says that you probably just want to be an asshole and are looking for an excuse.

Perhaps more importantly even than choosing the right role model... you all really need to learn how to model behavior and what modeling behavior really means. And you all need to get much better at understanding causality.

Let me explain with a little story...

When I was younger I played in bands. In one of my bands the lead guitarist wanted to be a rock star more than anything in the world. In his mind the platonic ideal of “Rock Star” was Keith Richards. So he looked at Keith Richards and thought... “Keith Richards is a rock star. I want to be a rock star. If I become like Keith Richards I will be a rock star. Keith Richards wears a skull ring and is a heroin addict. So if I become a heroin addict and wear a skull ring I will be like Keith Richard and thus will be a rock star.”

I assume you see the flaw here.

But a lot of you seem to be following the same approach as entrepreneurs. “My role model lives in the Mission, wears button down shirts untucked over his $400 designer jeans and doesn’t give a fuck about other people. I’m going to move to the Mission, spend too much money on pants and become a douchebag and next thing you know I’m going to be a gazillionaire!”

Sure... some of you are just fucking assholes and sociopaths who are attracted to the scene because it gives you an excuse to be what you are. And you’ve followed the money, figuring you can always jump back to working at Goldman Sachs or Bain when the bubble bursts. But we know who you are and we hate you and you’re not actually entrepreneurs and all the above is obvious to all of us. We’ll either force you out or wait you out. We’ve done it before.

It’s the rest of you - the true startup folks - who just need to stop being fucking douchebags. It’s creating a toxic environment, it’s making the whole world hate us, and it’s bad for everyone.

There is a brilliant line from a recent Alexis Madrigal piece in the Atlantic that sums all of this up.

“But, of course, that's also part of the new Silicon Valley parable: dream big, privatize the previously public, pay no attention to the rules, build recklessly, enjoy shamelessly, invoke magic, and then pay everybody off.”

It’s time to start being a decent human being first - and a successful entrepreneur second.

Because you all are managing to make even folks like me hate you and the entire scene and community. So just imagine how the rest of the world thinks about you - and me.

Read Next - Part 2, “Confidence” doesn’t mean what you think it means

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