[jmduke]

Definitely not _necessary_ — I was more or less resigned to not having the domain, since the sticker price was $170K and my mental "is this _really_ worth it?" number was high five figures.

As for why important: a melange of reasons. I had heard a _lot_ from customers and prospects that they couldn't find the site because they searched for/navigated to buttondown.com; I was faintly worried about SEO/brand impact from using a vanity TLD like `.email`; I was faintly worried about a more well-financed competitor buying it and redirecting to their own property; there are a very real number of legacy pieces of software that do not _accept_ `buttondown.email` as a valid domain, which is important when you're dealing with UGC.

(When I was debating what a reasonable purchase price might be, the framing that helped me make a decision was: "if this helps my overall conversion funnel grow by 2% in perpetuity, is it worth it?", and that answer was yes. Time will tell, of course, to see where that number actually lands!)

[rexreed]

Could you have structured the deal in a more cash favorable way seeing as you are paying for it from cash flow? That way it would have been less of an immediate impact on finances. For purchases like this, a revolving line of credit is helpful, even tho there's cost to that, because it lessens the impact on cash flow.

[jmduke]

Yup, absolutely — you see a lot of the larger brokers do some genre of lease-to-own program (pay us the purchase price plus a near-usurious APY over 24mos and at the end, you can keep the domain.)

My margins are solid and there aren't a lot of competing opportunities to deploy capital besides pulling forward cloud costs or hiring folks (which is a very different value prop altogether), so reasoning about the lump sum was pretty easy, but you're definitely right in that objectively speaking I should have just gotten a line of credit and amortized it that way.

[rexreed]

Thanks for sharing your insights and experiences! I am a fan of bootstrapped SaaS, just keep it going as much as you can and avoid the temptation to sell early, although I am sure that opportunity will present itself.

[V41frQo1SccpfHI]

Maybe a bit of a stupid question, but wouldn't it have been enough to just buy the domain and then configure a redirect to the old domain?

[rexreed]

Not if you want to build SEO authority on the new domain