I used to run a popular blog in 2000. The thing I didn't like about blogging, was that if I shut down my blog (which I eventually did), I would lose my entire audience.
So I started letting people sign up for email newsletters back then, just to kind of "own" the contact info of my readers, so I could continue communicating with them, even if I shut down my blog.
Today everyone is a publisher. And with the proliferation of social media, RSS and eventually Twitter came to solve that problem -- even if I don't tweet for a year, I'll still have my followers (assuming people are still using Twitter then, which I think they will be).
However, having the email addresses of your followers & fans still seems a bit more durable, not relying on Twitter or any other service.
So... that's why I built it. Did I think I would sell it so quickly? Originally, no.
What's funny is that right after I posted that blog post about how I use an unusual stack[1], MailChimps CEO sent me this eerily similar blog post about their stack:
http://blog.mailchimp.com/ewww-you-use-php/
I don't personally buy into the "being a single founder is harder" thing. True, if you don't know how to program (or design, or sell, etc) then yeah, it's gonna be easier if you have a co-founder who does. But if you're able to get it done yourself, having other founders around seems like a burden. That said, I've had success and enjoyed working with co-founders on bigger projects. But TinyLetter is simple enough that I didn't need anyone else.
Congrats on the acquisition. You're quite prolific when it comes to churning out the various web apps you produce.
Could you give us some insight into how you come up with the ideas for your apps? What's your thought process for determining whether an idea is worth pursuing or not?
Congrats again. Your success has always been an inspiration to me and is very well deserved.
Every time an idea pops into my head, no matter how silly, I write it down. Then when I think of (or read) something cool that applies to one of my ideas, such as a clever way to market it, I write that down with it.
Do that long enough (I've been at it 15 years -- I'm 35 now) and you'll have pages of notes.
As for which ideas I pursue- the ones I think I can pull off. Simple web apps, for example, versus a plastic stencil-like guide for cutting the hair on the back of your neck (idea #178).
As for doing it solo vs raising money & hiring a big team -- again, whatever way it will have the most success (for the product, and for my happiness).
This is an even sillier question, but how exactly do you keep track of all your ideas? A special notebook? Spreadsheet? What have you found is the best way to keep track of all your ideas on the go, while never losing track of them, etc?
We decided not to disclose acquisition price. I don't remember why we decided that.
I guess it's like telling people your salary -- just a thing people generally don't do. I think that'll change one day tho as stuff becomes more public.
I don't want to speak for MailChimp (read their blog post for that).
But basically, they like TinyLetter. TinyLetter likes MailChimp (srsly, the email business can be slimy as hell but they're totally legit, upstanding, & everyone knows it). TinyLetter has a good brand and a decent amount of users (roughly 500,000 people subscribed to 30,000 newsletters). Both companies recognize an opportunity that we think is large, and buying TinyLetter gives them a head start.
I'll be helping advise TinyLetter for a while, and we both really wanted to work together.
So basically, for these reasons and more, it just "made sense," if that makes sense.
Just out of curiosity (since you said ask me anything) -- How much did you sell TinyLetter for, and will you be joining Mailchimp? (What did the terms of the deal look like for this sort of acquisition?)
Thanks. MailChimp loves TinyLetter also, and will make sure it continues to get even better. Better != more complicated. Keeping it simple is top priority.
As for finding users, everyone who subscribes to a newsletter (~500k) goes through the TinyLetter flow, so that's the best advertising. Just took a couple people to say (tweet, etc), "join my newsletter!" with a link, and the viral-ish loop started.
http://news.ycombinator.org/item?id=2942129