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Advice for monetizing a newsletter?

Hi hackers!

A few months ago, I asked how to monetize my site http://uxtools.co. A simple suggestion was to start a newsletter, which now has over 1000 subscribers. I've also paired it with a blog that nets anywhere from 10k–40k views per post.

Now, I've been approached about sponsorship in my newsletter and blog. I'm not declared as a business, and I've never received transactional money other than through PayPal when freelancing.

So, how do I accept sponsorship and payment without looking clueless?

Edit: I'm in the US.

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    I've accepted money before (in the US) without incorporating. The main reasons I've incorporated in the past were to to (a) save a small amount on taxes, and (b) avoid liability in case someone decides to sue me.

    As for email sponsorships, during my short 6 month stint selling sponsors for the Indie Hackers newsletter, it appeared to be the wild wild west out there. Regardless of who I talked to — 1000-person companies or solo founder startups — the process was very informal and mostly handled over email. So don't worry about looking clueless :-D

    Side note: I'm interviewing the guys at ScottsCheapFlights.com, and they've managed to monetize their email freemium style. It's free for most people, but they actually charge a small fee to premium subscribers who get an email with more content. I think it's pretty novel, and not something I've personally seen too often. But based on their revenue it's working quite well.

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      Thanks, Cortland.

      The freemium idea is super interesting. I'll put some thought into how I might be able to make that work for me.

      Thanks for the vote of confidence! I'll dive right in and see what happens.

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    Taylor - email newsletters are kind of my thing. There are tons of insights in that interview with Scott and Brian. I have a class (free) on Skillshare (http://skl.sh/2pmrnWL)that might also be useful background (there are other and better ways to monetize beyond sponsorships). You can also hit me up directly if you have questions. tobin@tobinslaven.com

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    This comment was deleted 7 years ago

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      We're talking very low amounts of money (for now!) so that shouldn't be a problem. Good to know that I can file it the same as I would file freelance work. Thanks!