Dear Nick, About last night… Love always, Jason

So, the big show down in Gotham went down last night and I think we have a split decision. I wasn’t able to KO Nick

Denton, but overall I think we put on a decent show for the hard working folks who paid good money for their seats at

the Apple Store.

Seriously, it was a great discussion and as many of you know Nick and I are, in fact, friends. True, we have had

some tense and awkward moments in the recent past, but at the end of the day we both have the same goal: make

blogging profitable so that writers can get paid and make an even better product.

The great things about last night, for me at least, was that a) so many people showed up, b) so many people

understood the various business models and c) no one seemed to be up in arms about monetizing blogs. Compare

that to a year ago when even saying revenue and blogs in the same sentence meant you would get massively


One of the things I love about speaking gigs these days is that you receive real time, and next day, feedback on

your performance. In the old days I would just rely on what people told me, or second hand feedback. I thought I

would address some of the feedback.


Jeff asks whether the big media companies will be able to crush the small guys. JC says it will “validate” them.

Denton’s not sure, but thinks the only way the media companies will succeed is if they’re willing to take risks and

use “skullfucking” in headlines (ed note, spellchecker doesn’t like “skullfucking”).

I had some feelings on this but was unable to get the words out due to time constraints. Big media will be coming

into our space in a big way”trust me I know this. Of course, big media tends to get new mediums wrong”for a

while”before totally co-opting them. So, if you were planning on making a commercial blog I would get moving on it

because you will have serious competition in 2005.

Jeff: 10 years from now, where are you?

JC: $10MM/year in ad revenue. $2-3MM profits (EBITDA), multiple 2-10, turns into $4-$30MM worth (editor’s math, JC

wasn’t going to commit to a number).

Here is a little more clarity on that. I think that we can do $500 to $5k a month per blog over the next year. I

think we will have 100 blogs by the summer/fall. So, let’s say we do 1-2k per blog over the next year. At that rate

we can do $100k a month, maybe $200k. That is $1.2m to $2.4m a year. That isn’t a lot of money, but it isn’t a little

bit of money”it is somewhere in between the two. It’s good.

Maybe I shouldn’t discuss these numbers in public, but I’m kind of a blunt, up front person. I believe in

transparency. If we can do these kinds of numbers, and that is still an “if,” there should be no reason we can’t

scale up to 200-300 blogs and do even better over the next two years.

Now, what the value of our company will be if we do that is anyone’s guess. I’m not in this for the money,

honestly I’m not. I like building innovative things in publishing. If this is innovative, I can make a living from

it, and hundreds of bloggers can get paid I will consider the Weblogs, Inc. experiment a huge success.

Sometimes I fear that I come across as money obsessed, and Nick certainly tried to make it seem that way. However,

I learned from doing media before that in order to do great things in publishing you need money. It’s not the only

thing you need, but if you want great writers to spend a great deal of time making great things they need a great

paycheck. I want our writers to be over paid. I want them to get more money then they have ever received before for

writing. If we can make writers a ton of money for doing what they love they will love working with us.

Bottom line: I want to give writers the best deal in town. Better than the New York Times, better then Vanity Fair

and better then Nick Denton. That is a lofty goal I know, but if you don’t have goals you don’t get anywhere in



While Nick and Jason alternated between admiring and then slagging each other, I believe Nick came off the best.

Jason still has the sales pitch that I remember from him back in the day. Nick seemed like someone who was happy to

pay the bills and have fun.

Don’t kid yourself, Nick plays a good game at saying he is just in this for the fun, but you can be sure this is a

business for him.

In terms my never-ending sales pitch, you’re right. I do oversell, but it is really just my enthusiasm getting the

better of me. I am really excited about this. In fact, I never stop thinking about how to make WIN better and get

writers a better deal. I’m obsessed with our model and I want to get the word out. I really think we are doing

something revolutionary here, and if the price I pay is that I come off as too much of a sales guy so be it.


The first panel of the night featured Jason Calacanis and Nick Denton. I gather that everyone in the crowd expected

these two to go at it Jerry Springer style, but it never really happened. The two focused on business models for

their respective companies and the relative advantages/disadvantages. Surprisingly, I found myself agreeing with

Jason more than I agreed with Nick, which is weird considering I rarely agreed with anything that came out of Jason’s

mouth during his Silicon Alley Reporter days. I think Jason is on his way to a good start, with at least one

advertiser subsidizing one of his blogs. What I’m concerned about is his company’s ability to scale over time. He

mentioned he expected to have several hundred blogs within a few years’ time. I wonder how ad sales reps will be able

to effectively sell advertising on a web property with such wide-ranging content. Also, I think I’d be pissed if I

were to be working with him, considering he hasn’t hired any ad sales reps yet.

You are a smart man with great insights and tremendous wisdom. 🙂

Seriously, I’m concerned about our ability to scale as well. That is why we are taking it slow. We take one out of

200 bloggers who contact us to join the network. Most of our bloggers are now referrals from people already in the

network (hint, hint… if you want to get into WIN talk to one of the existing bloggers!). One of the great things we

have going for us is that our team of existing bloggers is very vocal and opinionated. If someone were to join the

network and not do a good job I would hear about”trust me on that one.

Now, in terms of advertising sales it actually gets much EASIER as our portfolio grows because we have a blogs in

groups. For example we now have like nine or ten wireless sites. When we talk to someone in the wireless space we can

offer them 200,000 wireless visitors a month, or just the 25,000 blue tooth visitors. Or, we can sell them all

200,000 visitors and have them make different creative for each site (i.e. on ad for a wifi product, another ad

featuring a Bluetooth product). So, more blogs makes a sales person’s job much easier.


(Nick) To Jason, is Mark Cuban an investor in your company? Will he be in the future?

Jason: He is not an investor right now, and in the future I will not disclose my investors (read:yes he will


On Fleshbot

Jason: “I’m not saying you’re a pornographer even though you have a porn site.” SMACK!

I think those were the two best attacks of the night. Nick Denton trying to out our investors and me outing Nick

as a pornographer. I don’t know what’s wrong with me; I used to be so much more aggressive. I found myself feeling a

strange kinship with Nick and not wanting to give him too much of a hard time.

If I did want to give him a hard time I should have asked him about how often his people leave, or why he makes

his writers give “props” to their advertisers every week and then gets all high and mighty about

advertising/editorial integrity (I would never have my writers give props to the advertisers).

But I digress… 🙂

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