This is a guest post from Gary Vaynerchuk — well-known entrepreneur, social media innovator, and author of “Jab, Jab, Jab, Right Hook.” See the original post this is adapted from and more like it on his blog.

I’m all about putting out content, becoming a media company, and providing value to your customer.

By giving away great content for free, you’re building up a base of fans and consumers who know that, not only are you good for your word, you also know your shit.

But giving away work for free can be hard. Really hard. You work a long time on something and then it’s difficult to just let it go. I get it. I really do. But the more you do it, the easier it gets. You build up a momentum that can’t be stopped, and it allows you to keep creating.

Giving away my best content for free has been my gateway drug to so many amazing opportunities.

But “best work” needs to be defined for the category you’re in. It’s not going to be the same for everyone, and you need to evaluate what can be given away and what needs to be held on to. For example, I’m blown away by the amount of people who don’t realize that the advice they give daily is exactly what they should turn into free content. So many people have a wealth of ideas that they can pull from and just aren’t doing it.

And then there’s the other side. Maybe you create a very specific product that takes time. If you’re a painter, and your best work is the most amazing painting you ever made, you giving it away for free is a different game. Then again, maybe you strategically gave it away; to an important museum, or to a billionaire that puts it in a prime spot in their home. Could that then become the gateway to more opportunities? Very possibly.

Essentially, any time you are deciding what content to distribute free of cost, it needs to be a strategic decision.

You need to be thinking three steps ahead. Because by giving away something for free, you’re looking to create leverage that allows you to eventually do something for profit, right? Right. So figure out what kind of content will get you what you want, and who needs to see it for that to happen.

Quick side story to illustrate that point:

My video editor DRock got onto my team by offering to make me a video for free. He could have made that first video for someone who isn’t me, and it might not have panned out the same. He might not have received the ROI of doing a video for free. That is how strategy plays into this. Everything I give away for free has strategic purpose. I understand why I’m doing it, and that’s why it becomes so much easier to do.

Now we’re at the really big part of this.

Way too many people do stuff for free and then expect an immediate result; they expect the windfall behind it. Then, when that result is not delivered, they become disappointed; and in that disappointment, they don’t follow up. They don’t try it again. They don’t repeat that same action over and over. It’s sad because it’s actually the repetition of working for free that has more upside than anything else.

Three out of five times, it will bring you some kind of value. Don’t focus on the two out of five. You might miss the other three.

About Gary Vaynerchuk

Gary Vaynerchuk has built businesses all his life: In his 20's, he grew his family liquor store from $3 million to $45 million in 5 years, launching, one of America's first wine e-commerce sites. In 2009, he co-founded VaynerMedia, a social-first digital agency which helps brands market in the year we live in. An angel investor and adviser to some of the most successful tech startups since social media’s early days, Gary has counseled and invested in more than 50 tech startups including Twitter, Tumblr, Medium, BirchBox, Uber and Venmo. In 2014, Gary launched $25 million seed fund VaynerRSE to continue his successful investing career.

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