Tell you what, though. If you want to sell this thing, what I'd do is, develop it and open source it:

* Enterprises will pay money for open source products. In fact, it's easier for them to pay for open source than to deploy it for free.

* IT people will bring open source stuff in house to play with it, which makes them your shadow sales force.

* It's really easy to qualify accounts for sales; just have an inside sales guy call up and ask if they use your OSS project and like it.

A little confused as to why you, as a sole founder with little hope of securing funding, would choose a direct sales product with a 4 month sales cycle. But, best of luck!

I'm not sure why you don't think I could get a sales guy who owns a chunk of the company. Also conservative, non-ad revenue based products have a better chance of getting investment than the latest chance to make revenue from web services via the oversaturated ad sales market.

But thanks!

I wonder if there's a rule-of-thumb formula that can be applied. "Don't attempt a product with an N-month sales cycle unless you have a company of at least N*M employees."

I suspect M is closer to 10 than 0.25.

If you can leverage contacts to shorten the first few sales then a very small team (2-4 people) can endure the true sales cycle until you pick up momentum.

If your contacts own the budget and purchasing, maybe. Otherwise, you're probably deluding yourself to think that personal relationships are going to cut the sales cycle on an enterprise product. The sales cycle on a securty product at a BigCo includes:

* Weeks of presentations and demos (this part you can cut with relationships)

* Weeks of pilot deployment, which in this guy's case will involve coordination between security, architecture, and server IT.

* Weeks of user education and training (something everybody forgets about).

* Weeks of back-and-forth about missing features and requirements.

* Weeks of negotiation for first PO, assuming all the previous stages went well.

* 3-5 months of delay waiting for receivables.

What friendships will do for you in this process is eliminate the hidden "in-between" steps where people get distracted by their real jobs for 1-3 weeks and don't return your phone calls. But most people don't have friends in BigCo's that can simply cut them checks.

Also, when you try to shop this to VC, most of them aren't going to be impressed by the demo and pilot deployments you've secured with your friends.

Most of the entrepreneurs we work with are over 35, and in many cases know and/or have worked with department managers and senior managers who own a budget and can influence purchasing. For the most part they are not selling applications that are mediated directly by IT in the way that a security app would be so some of the friction is taken out of the process. I do agree that for younger entrepreneurs in the security space you are offering a realistic scenario. My comment was more in response to team size vs. sales cycle than the overall thread, I should have been more specific.