Like many hurdles with startups, the first of everything is always the hardest. The first money is always the hardest to raise, the first employees are always the hardest to find, and the first advertiser is always the hardest. We’ve already covered how we’re selling advertising on our startup.

Now, these days, advertising is the lifeblood of web startups. Many startups have no other business model than banner advertising, so advertising can be an important factor in whether or not the majority of startups 1) make it off the ground and 2) actually become successful.

Just Get Points on the Board

In football, when a team is struggling, often one of the best motivators is getting some initial points on the board. Many times, when a team is driving down the field and they get down within the 10 yard line, the coach calls in the kicking team on 4th down. And, the majority of fans probably boo over this decision, the true football minds realize this is the correct move to make.

For a team, seeing a big goose egg on the scoreboard can be very debilitating, but, looking up and seeing that “3″ on the scoreboard, it makes things seem a lot more doable. Suddenly you “have a chance” in the game, and I don’t think we have to go over the numerous comebacks in history, all spurred by a simple field goal.

Like football, advertising on your site is a similar concept. With no advertisers, it may seem near impossible to get someone signed up, so you may be more desperate or lose faith more easily than you should. This biggest hurdle you need to overcome is just getting over the mental barrier of that first advertiser, and just getting 1 contract setup can change your whole direction.

Why Is the First So Important?

When trying to sell anything, it’s always easier when someone else has already gone before you. Remember the first people to buy hybrid cars? Everyone claimed they wouldn’t pay for themselves, would break down, etc. and today we have dealerships buying BACK hybrids and reselling them for their same value they had when they were new. Suddenly a depreciating asset is worth more two years later??

When trying to sell advertising, it’s the same concept. Your potential clients don’t want to be the only ones driving around these silly hybrids. They want to know someone else has already “taken the risk,” of advertising on your site, and that they won’t get burned if they choose to advertise on your site.

Also, once you already have an advertiser on board, you have an opportunity to create scarcity and drive up prices or increase urgency. Say I have 10 advertising spaces on my site, one of which has already been sold. First, I have a rational for charging a set price for the spot (whatever my first client paid), and second, I can create urgency on the client. With no advertisers on the site, my timetable for selling the ads is essentially limitless. Once I have a first client on the site, suddenly I have a sell-by date that will mean I have to begin my first client’s advertisement on a certain date.

If I have any empty spaces after that date, I’ll be losing money everyday, as the space will go unsold, and I’ll possibly open myself up to my first client asking for discounts, more impressions, etc. Selling this first space creates an urgency for myself, the startup, and also for potential clients. You tell em, “the ads are going up on oct. 1, you have until sep. 15 to make a decision or I’m selling the spot to someone else.”

Advertisers don’t know that you don’t have anyone else to fill the spot after the 15th of September, but with that beginning date, you have a timetable and create instant action from potential advertisers. Getting your first advertising sale is of paramount importance for trying to sell out your advertising inventory, so when beginning to sell ads, don’t go for a home run with the first sale, just look to MAKE that first sale, and everything will get easier from that point forward.

Advertisers, Advertisers, Everywhere

So you say getting the first advertiser is the most important? Well what if you don’t have anyone in mind or for some reason can’t actually SELL the space?

Well, you can look at doing advertising trades, revenue-shares or simple bluffs.

Simply putting a free banner on your site can make it appear to other advertisers that you already have an ad deal in place. The widget above is an American Apparel promotional widget that anyone can easily insert into their site. Then, when talking to other advertisers, instead of blatantly lying and saying American Apparel bought a spot, you can simply point them to your site, tell them to check it out, they’ll see the American Apparel stuff, and suddenly they’ll get a lot more interested.

They’ll think, “what does American Apparel know that I don’t?” Suddenly the urgency might be there, and advertisers will think they might not have an opportunity to advertise if they don’t act now. Remember, the goal of advertisers is to …ADVERTISE. They need to put their banners somewhere, so why not your site?

Say you don’t want to go this route. What about your friends startup that he’s trying to launch from Y Combinator? Why not trade banners with him? You each get some value from the cross-promotional plus it looks like you have strong relationships with other up and coming sites in your demographic.

Don’t have any friends with startups? Start contacting startups that are similar to you. Ask them if they’d be interested in a cross-promotional banner exchange. Give them a limited length on contract and tell them, if you sell an ad, you have to take theirs down. Now, you have, “advertisers,” on your site and you don’t have any unused inventory, and once you sell an ad, you can immediately put it up.

Advertising is Easy, You Just Need to Learn the Ropes

Advertising can seem really daunting when you’re first starting up, but like anything, it definitely gets easier. Remember when you thought it would be impossible to convince an investor to put $25,000 into your startup? Now you’re looking at multi-million dollar investments like it’s nothing (we hope).

The same principle applies to advertising. The first advertiser is the hardest, and soon after that, you’ll have to choose WHO will be advertising on your site, and begin to turn away potential clients.

So when you start to begin your advertising sales, make sure you get the first advertiser on board, by any means necessary, and from there just leverage that first sale as much as possible.

Do you have any tips for getting those first advertisers on board?

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