New Disruptors 63: Failing Upward with Greg Knauss

Greg Knauss is an independent software developer who created Romantimatic, a reminder program for absent-minded sweethearts. You may know him from the early 2000s: from Suck.com and Metababy and Rainy Day Fun and Games for Toddler and Total Bastard, a collection of stories he promoted on what was arguably the first digital book tour. Then for a decade he toiled behind the scenes until he went out on his own. We'll talk today about his expectations, the reality, and fear of failing–and of succeeding!

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Things we mention in this episode:

Greg and I are both so old we remember seeing the launch of Mosaic (in different forms), the very first widely distributed graphical-user interface Web browser. Marc Andreessen and his colleagues at NCSA didn't invent the Web, but they made it accessible.

Ted Nelson gets credit for creating the notion of hypertext, which he always envisioned as two-way links! The original Netscape browser let you edit pages directly. Everpix (the site that I couldn't recall) had to shut down, despite being beloved, because the revenue didn't match up with the cost of providing service.

Kevin Kelly and I discussed 1,000 true fans, distributed collaboration, and his book Cool Tools last week. Greg's essay, "Talking about Failure," covers some of the ground we discuss in this episode. Cabel Sasser's talk about coping with panic at his firm, Panic, when things started heading a direction he didn't want to walk down—and how he got through it. Also watch Christina Xu and Jack Conte talk about similar pressures and outcomes.

A lot of interesting thoughts came out of XOXO 2013. Frank Chimero wrote of "The Inferno of Independence." Leah Reich discussed the value of critique in "The Uncanny Valley of Earnestness."

Romantimatic was given a hard time by Elle, but Mashable was much more fair. Greg was also interviewed by CBC about the app.


The New Disruptors is a podcast about people who make art, things, or connections finding new ways to reach an audience and build a community. Glenn Fleishman is the host, and he talks with new guests every week. Find older episodes at the podcast's home.

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