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Creatives Ask: What Kind of Web Do We Want, Anyway?

·Contributing Editor

(Photo by Rob Pegoraro/Yahoo Tech)

The Internet has figured out two ways to pay people.

One — doing piecework for one site/app/service or another — is open to almost anyone but doesn’t necessarily yield much. The other can be fantastically lucrative but just as fantastically rare: Win the dot-com lottery by creating a startup whose name becomes a verb.

But what about that large space in the middle? What if you don’t want to be a Mechanical Turk or some other cog in the “gig economy,” but at the same time you don’t want to gamble on the startup life and so grind away all your work-life balance? 

I spent the past weekend at the XOXO conference in Portland, Ore., looking for answers to those questions. Organizers Andy Baio and Andy McMillan started the event in 2012 as a place where independent creative types could learn from each other’s stories. 


That might make XOXO sound like an extended pep talk with breaks to sip local microbrews. But the reality of it was deeper, darker, and sometimes a lot more painful. 

And its lessons don’t apply just to tattooed hipsters speaking earnestly about Their Art: They have implications for all of us who consume creative content of almost any kind. Do we really want to count on large corporations — and lucky startups recycling their money — to inform and enlighten us? This XOXO and the one I attended in 2013 left me more convinced than ever that we’d all be a lot better informed and entertained if the Web wasn’t open only to the equivalent of rock stars and the record labels behind them.

Hell is other people’s money

One of the biggest barriers on the path to independence for creative people: the ads that are supposed to keep their sites in business without readers paying them directly.

XOXO’s talks led off with a cautionary tale from semi-retired blogger Heather Armstrong. She said that, after banner-ad revenue on her site tanked, she began writing sponsored posts; those, in turn, became a “torturous and soul-sucking” exercise when sponsors decided they didn’t want their names associated with posts — especially ones as zesty as some of Armstrong’s — that they couldn’t micromanage.


Heather Armstrong (Photo: Simon & Schuster)

Other speakers at the event had no great answers for that problem. Alex Blumberg said his podcasting company, Gimlet Media, gets “insanely high ad rates,” but he admitted he got a little nervous listening to Armstrong. An onstage reunion of the founders of the late, great Suck.com only served to remind the crowd how good we had it back in the unsustainable dot-com craziness of the late 1990s.

Mallory Ortberg, founder of the feminist-essays site the Toast, didn’t count on any such generosity. Her site launched in 2013 on a $200,000 budget (including money set aside to pay freelance contributors) and turned a profit three months later.

“We still underpay ourselves,” she allowed. But on the upside, they don’t have to “obsessively react to every single cultural trend on the Internet to make money.” That seems a decent definition of achievable success for a publisher — and for readers bored by clickbait.

Funding is no fun

Conversely, XOXO attendees were reminded that taking on investors can raise all kinds of issues of its own. Investor Bryce Roberts summarized one result of getting on the funding track: “Building for investors and not necessarily for customers.” (To that I’d add: See all the startups that don’t include privacy in their “minimum viable product.”)

Roberts’s solution is indie.vc, a fund that’s not looking for billion-dollar “unicorn” startups and will accept a slow payout over time. 

Andy Baio’s own career offers a different warning. He sold his collaborative-calendar site, upcoming.org, to Yahoo in 2005, then watched it get neglected and eventually closed. Last year, Yahoo sold it back to him, and he’s since launched a Kickstarter campaign to revive it.


Crowdfunding is a perennial topic at XOXO; the festival itself began on Kickstarter. Saturday, Iron Circus Comics publisher C. Spike Trotman explained how she has successfully used Kickstarter to fund each new round of titles. Her own definition of making that work: “The tenor of criticism has changed from That Will Never Work to That Doesn’t Count.”

Left unsaid in the funding discussion: The difficulty of standing out on crowdfunding platforms that increasingly function as yet another PR tool, that often leave backers disappointed  — remember the example of video game console developer Ouya, which seemed on track when CEO Julie Uhrman spoke at 2013’s XOXO but closed in July — and that sometimes harbor outright scammers.

Exclusion and inclusion

Finances aren’t the only challenge for independent content creators. Loneliness and self-doubt were recurring themes all weekend. (“Impostor syndrome” should have been the free square in any game of XOXO bingo.) But those aren’t the only nonfinancial hurdles. 

Game developer Zoe Quinn — among the foremost targets of the vile harassment symbolized by the #Gamergate hashtag — spoke with grace about the ongoing death threats she received after suggesting that the game industry could be more inclusive.

“Most people participating in online harassment think they’re the good guys,” Quinn said. It’s the same self-righteousness, she added, that surfaces when people delight in the misery of Ashley Madison subscribers whose data was leaked.

TV and podcast host Veronica Belmont compared the way we talk to Siri, Google Now, or Cortana to the conduct we see too often online: “We’re nicer to our computers and phones than we are to other people on the Internet.”


But it’s not all evil out there. While acknowledging that Gamergate represents the worst of the Web, Web developer Eric Meyer said that the support he received after the death of his daughter Rebecca to cancer on her 6th birthday could be the best.

Meyer asked a tough question: What sort of behavior do we enable with the services and apps we make? Do we enable empathy or abuse? A site may not think about that question when it is setting up its comments system, but it owns the results we all have to live with.

“What we make easy speaks to what we value, and what we make difficult speaks to what we reject,” Meyer said. “We’re building like crazy. It’s far past time we started building wisely.”

Email Rob at rob@robpegoraro.com; follow him on Twitter at @robpegoraro.