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Yes. There's a technology lesson -- deploying and maintaining client software [software that is installed on individual users' machines] is really hard. There is also a lesson in the desirability of finding a real problem, a real need, and satisfying it. Finding a need is a more straightforward job than inventing a need. It's a tricky balancing act though, because there's always a little bit of creation of need involved: At the same as you address a new problem, you are creating new opportunities. Brightmail is out to do both -- our initial products are aimed at solving a very obvious problem. But future products will address the opportunities that we create by solving that problem.

Can you talk more about those future products?

Unfortunately we're not really ready to talk right now about future products. But they are all oriented toward improving e-mail, making e-mail a more useful medium than it already is. The overall strategy of the company is to introduce spam control and use that as a beginning for many other services in the same way as other companies like Yahoo and Netscape and Amazon used their first very simple product -- a directory, a browser, book sales -- as a way to build up the market, build a brand name, build awareness, and then layer other products on top of that.

You say that one of the things you've learned is that deploying client software is really difficult. With Brightmail, you are primarily targeting Internet service providers as customers for your software. Are ISPs a big-enough market for striking it rich?

In the spam business? We know that spam is a real problem and it costs a lot of money for ISPs and corporations. We estimate something like a billion dollars a year is lost due to spam. A one-million-person ISP will typically lose about $7.7 million a year because of spam. Is that opportunity big? Yes. Is it capped? Yes also -- but between here and that capped opportunity is a lot of revenue. We see an opportunity to go grab a pretty reasonable, healthy stake of revenue, and create a core business big enough to build a lot of relationships.

And then leverage those relationships with your new products?

Exactly.

One of your closest relationships is with Sendmail, the open-source software company. Right now, your software is proprietary. Do you see any threat from the open-source software development model, as far as Brightmail's prospects are concerned? Could the open-source community develop its own spam-control methods?

That's an interesting question. It would take a massive coordination, and while the Internet helps coordination in an asynchronous mode, its pretty hard to do in a synchronous mode. Part of the value that open-source software companies like Red Hat offer is that they add a layer of support on top of this asynchronous coordination of writing software. Similarly, what we basically do is that kind of support. We are the ones that are accountable, we're the ones that are writing the spam-filtering "rules" on a minute-by-minute basis -- and it's expensive to run a 24-7 operation like ours. It would be pretty difficult to do what we do in an open-source manner.

There's a saying in Silicon Valley these days that there is no shame in being involved in a failed start-up -- on the contrary, I've heard it said that venture capitalists look favorably on entrepreneurs who've failed a few times -- they are supposed to have learned from their mistakes and have a better idea of what it takes to succeed. It's hard to know whether to call FreeLoader a success or failure -- you certainly picked up a nice chunk of change, but the company itself was closed down and the product doesn't exist. Did that help you or hurt you the second time around? Is it true that failure looks good on a Silicon Valley résumé?

I don't know. It's true and it's untrue. I've heard people say that -- but there's a difference to pay attention to. Did you try with gusto? Or did you just whimper along? I see lots of companies and I interview people who just sort of puttered along and didn't really go for it, and I don't think anybody respects that. I guess if they end up being a big success people respect that. But what people really like to see -- and by people I mean investors and employees and people you're doing a joint effort with -- is that you are willing to swing for the fences. If you don't quite get there or if you struck out once before, that isn't necessarily such a terrible sign.
salon.com | Nov. 1, 1999

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