The service, which launched in February, attracted a number of investors, including SV Angel, Accel Partners, Chris Sacca, Josh Kopelman, Max Levchin and others, who put $1.1 million into Gumroad’s seed round. But just three months later, Gumroad is announcing a $7 million Series A investment that is being led by Kleiner Perkins with participation from Crunchfund and existing investors. Kleiner Perkins partner Michael Abbott is joining Gumroad’s board.

Gumroad works by letting sellers post a URL to Gumroad, which creates a unique shortened link that leads back to Gumroad. Or they can upload a file of up to 1 GB in size. Sellers can set their price or leave it open to buyers as to how much over a certain amount they want to pay. Buyers who clicked on the link are presented with a simple product page with a description of the item and a button to buy. To purchase, they just need to enter in their email address and a credit card number. Buyers then get a link as well as an email receipt giving them access to the content.

Sellers are paid monthly via a PayPal account, minus Gumroad’s take, which is 5 percent of the purchase price plus 25 cents. Gumroad can be an attractive way for people to sell directly to users because it allows them to tap the channels they already use to interact with fans and followers such as Facebook and Twitter. Instead of having to set up their own commerce site or submitting their stuff to an existing market that takes a heavy cut, Gumroad offers a pretty streamlined way to sell.

In some ways, it reminds me of Chirpify, a service that lets people transact directly through Twitter. But that service also requires payment through PayPal, which not everyone has and it takes some getting used to buying directly through @replies on Twitter. Gumroad handles its own payments so it doesn’t have to depend on anyone else to complete the transaction.

There are still some questions about Gumroad. For instance, if I sell a link to my YouTube video, there’s still a chance that someone could just go there directly without paying. With a new payment service, you also have to trust that Gumroad is completely secure. And I’m not sure how Gumroad prevents me from monetizing someone else’s link. Lavingia told me that Gumroad monitors downloads to make sure people are not sharing links and it responds quickly to take down requests if someone tries to sell another person’s goods. And he said that the service is fully PCI compliant.

I think Gumroad is another great tool that is helping creators make money by going directly to fans. We’ve seen comedians like Louis CK sell their work online, bypassing some of the existing sales channels. Now, with more options like Gumroad, Chirpify and Kout, they can hold on to a greater portion of the revenue and also serve more savvy online fans who are ready to buy in more non-traditional ways. It doesn’t mean the old selling ways are gone, but these new tools are changing the game for how much freedom artists have to sell their wares.

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Chirpify, which started by focusing on physical goods, is now expanding the platform to include digital content, so companies and artists can sell music, videos and tickets directly to their fans.  Rhymesayers Entertainment, a Minneapolis-based hip-hop label, is one of the first customers to use Chirpify’s new Twitter Commerce for Digital Commerce platform and it will sell music and other goods to its fans over Twitter.

Chirpify works by letting sellers advertise a deal and complete the transaction without leaving Twitter. For instance, a music seller could upload their content to Chirpify’s platform and then push out a tweet asking their followers to buy a certain track by replying with the word “buy” in their tweet. If the consumer already has a Chirpify account, the money will get automatically deducted from the PayPal account that they connected through Chirpify.  If the buyer doesn’t have a Chirpify account, they are prompted to set one up along with a PayPal account if they need one. The transaction is completed through a direct message to the consumer with a link to download the digital content. For physical goods, the seller will send the goods to the address listed on the user’s Chirpify account.

Chris Teso, founder of Chirpify, told me he’s working on lining up other payment options aside from PayPal. And he said there is still a bit of a learning curve for some customers, who are surprised to see how easy it is to buy something through Chirpify. But he said the platform is proving to be popular with Fortune 500 companies, who are able to monetize their social media relationships with fans. The move to expand to digital content was prompted by musicians and artists, who saw a similar opportunity to sell their stuff to their followers. He said there’s also room for authors and comedians to sell their wares directly through Chirpify.

“We were focused on the physical implementation for brands but we backed into the digital commerce. But it makes way more sense. If you sell on iTunes, they don’t get data back. They don’t know who they’re selling to. But they have Twitter followers so we just let them sell directly to them,” Teso said.

Chirpify members also seem to find the service useful. Though Teso won’t say how many people are on the platform, he said 50 percent of members have transacted on the platform. In addition to an e-commerce platform, Chirpify also enables peer-to-peer payments and donations as well.

The company is opening up a lot of opportunities for companies and artists to really starting making money through social media. As we’ve seen with comedian Louis CK, there’s a lot of money to be made by selling directly to fans. It won’t work for every product: Teso said they’re figuring out how to tackle things like sizes and customization, which is harder to handle over Twitter. But I think this is still a pretty awesome way to sell and cut out some middle men along the way.

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Chirpify, formerly known as Sell Simply, is today unveiling its Twitter commerce platform, an all-in-one tool that taps PayPal and allows users to monetize their tweets. The company said it’s the first one to turn Twitter into a direct sales channel. Chirpify has signed up its first brand, PowerBar, which will sell products directly through Twitter.

There are actually three ways to use Chirpify. There’s Chirpify Commerce for brands, Chirpify Payments for peer-to-peer transactions and Chirpify Donations for charitable organizations looking to raise funds. Sell Simply, which quietly rolled out in July, offered a basic version of the service, primarily for peer-to-peer payments. But now, the platform is ready for a formal launch as it fills out its offering as a commerce service.

Here’s how it works: A brand with a following on Twitter can connect its PayPal business account to Chirpify and then start tweeting out items for sale through a simple dashboard. This could be time-sensitive deals or highlighted items that are on sale or need to be moved. The tweet could say something like “Sale on X item. Reply ‘buy’ to purchase X.” When the user replies with a tweet saying they want to buy the product, the money will get deducted from their PayPal account. Chirpify parses the tweet and then will fulfill the transaction if the user has connected their PayPal account to Chirpify using a quick OAuth permission. If the buyer doesn’t have a PayPal account, they are prompted to set one up and connect to Chirpify.

Chirpify will take 4 percent of transactions from recipients who use the free account. For $49 a month, sellers and recipients can lower the fee to 2 percent. And for bigger brands, they can pay $500 for no fees and deep integration into their back office software. Right now, Chirpify can work with ecommerce software Magento, allowing sellers to list and manage items on Twitter from Magento.

“Brands are already tweeting about products, but those are just broadcast ads trying to lure consumers from Twitter to a five-step checkout process,” said Chris Teso, founder of Chirpify. “We eliminate that and make commerce frictionless.”

Chirpify is interesting because it brings payment and commerce functionality to a platform that wasn’t designed for it. But Twitter is increasingly where people are hanging out, following friends, celebrities and brands too. Being able to sell directly through Twitter allows a brand to not just push out advertising messages through a popular channel, but actually do some business. If pursued with moderation, it could be a powerful way to reach out directly to consumers and could result in a lot of impulse buying. And because it’s built atop Twitter, a popular item or sale could go viral, especially with the right supporters.

Brands are trying to also leverage Facebook, but many try to divert consumers away to their own sites. Chirpify would keep people right inside Twitter. That could be helpful for some companies that have built good consumer engagement through Twitter or have seen their email open rates for newsletters and daily deals decline.

But if taken too far, this could sour some users on a brand if they push too much of a hard sell. The items or sales will need to have some significant value, or users may find the Twitter relationship suddenly very pushy. Also, brands will need to be selective about what they sell, choosing straightforward items that can be described in a few words with perhaps an accompanying picture. And consumers will need to sign up for Chirpify and connect their Twitter and PayPal accounts, which is pretty painless but still requires a couple steps.

But I think this could still be pretty powerful if consumers sign up for Chirpify. Nonprofits could rake in a lot of money with a simple appeal. Celebrities could go directly to their fans with an exclusive deal or sale.

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