Even when it comes to B2B, it is better for a service like this to get into enterprise via their geeks than try to appeal to their suits, because Tarsnap's strengths mean nothing to a suit.
I do consulting for hedge funds in NYC. Most of them use an accounting system called 'Advent Geneva'. This particular software solution has a Unix component where the actual accounting data lives. My clients would like to back up this database securely and reliably. Security is extremely important as for a given hedge fund, their trades and positions are extremely sensitive information. Tarsnap is exactly the backup solution these clients would want to use. As a consultant, I don't think I will ever be able to sell Tarsnap in its existing form to these clients. Keeping aside pricing, these clients would want an SLA (and other legal stuff mentioned in the article) for the backup service. These clients are more than willing to pay costs associated with this higher level of service and will benefit tremendously from using Tarsnap.
I do not know any backup solution which is better than Tarsnap and it's unfair that businesses will have to use less-than-ideal technical solutions ONLY BECAUSE Colin doesn't want to adjust 'business side' of his product offering.
Underneath it can all be the same product, just packaged differently depending on who the potential customer is.
See, this is something I have thought a lot about. I can understand the value of the 'enterprise' pricing tiers (and yeah, if I have to do a bunch of paperwork, it's totally fair for me to charge you more.) So I can see where pricing tiers could be a good thing.
However... the bit I'm questioning here is how far you distance your 'enterprise' product from your 'geek' product- Especially if you have a strong 'geek' following already, I would argue that you don't want to start over in the 'enterprise' space. You want to carry over the name. Either, as Patrick suggested, move the 'geek' product to a less-accessible URL and professionalize your primary brand, or build a "tarsnap enterprise business edition" url.
Either way, there is a whole lot of value in a brand valued by nerds. I agree that brand needs to change some (and the product needs to change more) to be marketable to the enterprise, but... the boss basically respects his or her geeks... enough to pay them a lot of money. Sometimes I even find the business folks emulating the geeks when dealing with computers. A MBA where I worked saw how paranoid I was about ESD and asked for one of my wrist straps. He used it while he was typing emails on his mac. The "business edition" of the thing his geeks say is awesome is going to have a lot more pull than just some random new brand.
I normally would agree, don't throw away a perfectly good brand if you can avoid it. But if the customer has never heard of your brand, and wouldn't understand it if they did hear of it, that's one of the few cases where coming up with a new one could make sense.
If they've never heard of the brand, you are right. A good name that your customer hasn't heard is better than a bad name your customer hasn't heard.
But, my belief is that there are a lot of semi-technical "enterprise" or at least "SMB" types on places like hacker news, who likely have heard of tarsnap. And even if not, as I said, management listens to their technical help, often more closely than it seems.
Hell, I've had a few 'enterprise' type companies coming to me, by recommendation of their technical folks. The deal usually falls through because I am not equipped to deal with that sort of thing, but the opportunity was there, because a non-management technical person knew my name. Colin is way closer to being able to support those sorts of customers than I am, and I think he has a much larger technical userbase than I do, too.
>and wouldn't understand it if they did hear of it
I'm a firm believer that how recognized your name is matters a whole lot more than how "good" or "meaningful" your name is. A bad name that your customer has heard before is worth a lot more than a good name that your customer has not heard of.
What does conviva mean? what does akamai mean? Avocent? Cisco? To your average English-speaking monoglot, these are just random strings of letters. Much like 'tarsnap' is a random string of letters to people who aren't crusty sysadmins. The names of companies gain meaning through use.