I'd say Empire Flippers, too. I haven't sold through them but I've had a couple of discussions with them. They also have a tool that lets you get an idea of what they think your site is worth, depending on net revenues, number of social media followers, how many hours it takes to run the site, how fast you want to sell, etc. I know they've made some changes lately, but I think they take a 15% cut.

This thread should be stickied, it's relevant to everyone. We help people get into making money online but there is little discussion of getting out.

Some ideas to consider even though I am NOT a tax expert, NOT a financial expert and NOT telling you what you should do. I don't know your specifics but some of these might appl.

For people who report web income as personal income
- Look up your tax rates to see what percent you pay per income level?
- Sell your sites over a few years time so that you control the yearly tax level you are in?
- Consider what you will do next in life. if there will be major purchases required to transition, ie: loans required, getting those loans in the same year you report the income may allow a partial writeoff as your site sale revenue is offset with operating debt? (Amazon made billions, paid almost no tax, new debt is partly how)

For people who report web income as part of an LLC or other form of official business
- Pay yourself a reasonable amount if the business is in a higher tax bracket than you are? It lowers the total business profit
- Again, if the LLC sells off assets but purchases new assets, like farm equipment if you want to become a farmer, the debt may offset some or all of the tax due on profits, but only in the same business year.

A combination approach works sometimes too. I've seen a few individuals sell their small online business and they created an LLC AFTER they sold. Why? Because they became consultants at that point. They didn't love the business but they loved helping others in the business, and got paid for it.

I'm really not an expert so absolutely find and consult with a licensed financial expert before doing anything. I've sold sites in the past and know how that worked out for me come tax time but that's the extent of my experience. You might get more ideas from watching how companies like Amazon manage to pay very little tax, for them it's all about timing and costs vs profits management.

Paying tax isn't a bad thing though, it pays for all the nice stuff we enjoy, but paying too much tax is never fun.

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Advice about the sale of a website - don't try to maximize for every dime by absolutely mastering SEO, content, social etc so that you can get the absolute top dollar in a sale. When you do this a potential buyer won't see an opportunity to make major immediate improvements and likely won't make an offer.

This is not my advice, this is from Greg Elfring of Empire Flippers. This is a great interview with lots of juicy tidbits but fast forward to the 22:05 mark to hear how to actually get the most from a sale. [youtube.com...]

Been here 11 years, have to say I don't remember a thread that could literally change a person's (potential family's) life as much as this thread. Definitely might consider making it a sticky.

This a "fork in the road" kind of discussion. One is past the getting started stage, has entered the been found and getting traffic stage, and coming up against the get to the next stage of growth and profitability. Not sure it qualifies as a pinned thread, however. Each experience and metrics involved will produce different results on any given day.