I tend to beat myself up when I review historical records on names I’ve lost at auction. Names that, looking back, I shoulda bucked up and purchased. Names that woulda been great projects to develop. Hell, fun projects to develop (down the road).
But, as I typically self-finance all acquisitions, if a name doesn’t have a clear road-map on how to re-coop its investment within a year (or two), I bail.
That methodology has worked well for me over the years, but it never lessens the sting of a lost asset. Assets which, in my imaginary world, I’ve already acquired, developed, monetized, and I’m sitting at the desk in a private equity firm signing the papers for their acquisition of the property.
To Shane’s question, though, if I had a million bucks, I’da acquired every single one of these.
On that note, let’s review (in no particular order) :

BridgeLoan.com
Sold Date: 9/7/2009
Sale Price: $27,101
By the time this name reached my radar, the bid was above my limit, which woulda been around $8-$10k. But Lawdy, it’s a gold-medal name. Lead-Gen written all over it.

Canyonlands.com
Sold Date: April’ish 2010
Sale Price: $4,188
I fell asleep at the wheel on this one – didn’t even realize it was headed to auction, so I never back-ordered…
oops.
I’m a sucker for the tourism and travel segment, though. I prob woulda bid up to $5k on it.

FlashCards.com
Sold Date: 1/30/2009
Sale Price: $40,200
My pea brain required many (many) flash card exercises growing up. And look at me know!
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The $40k range spooked me though.. And – actually – now that I’m revisiting this, $40k is a bit overpriced, imo. I would’ave liked to grab it for $5k-$10k. Still a neat name, though.

CowboyHat.com
Sold Date: 10/27/2008
Sale Price: $16,801
CowboyHat.com for $16k is like Mad Magazine – CHEAP. The ecommerce angle on this name is as ripe as a Georgia peach. Sling a couple hats here and there, and the investment is paid off. I didn’t even watch the full auction, as I expected it to last for hours and sell north of $30k…

ShotGlass.com
Sold Date: 11/10/2008
Sale Price: $16,655
A name I liked, but was concerned on the flip and/or development at that price.

CarlsbadCaverns.com
Sold Date: 1/14/2008
Sale Price: $15,000
A name I actually bid up to $2,000, then bailed. Again, I’m a sucker for this segment. And I thought this one was a beaut.

KeyWest.net
Sold Date: 2/9/09
Sale Price: $13,800
Yeah yeah, it’s a .net. But Lordy, it’s Key West! One million people visit there every year! I actually bid this one up to $5,050, but chickened out there.

PaintballGun.com
Sold Date: 11/7/2008
Sale Price: $10,299
Again, not necessarily one I’d try to develop, but one I’d potentially try and sell to a paintball gun manufacturer.

WhiskeyBarrels.com
Sold Date: 4/15/2010
Sale Price: $504
Mr. Berkens beat me for this one. I was hoping to snipe it for a couple hundred bucks, but in the end, I bid up to $479, and he won for $504. I’m not a big whiskey drinker, but thought it’d be loads of fun to start some sort of broker / middleman businesses buying and selling these barrels (as they’re re-used & recycled several times over their lifetime). But I can’t now. Mr. Berkens ruined my dream. : )