Before Cortana, before Siri, before Alexa, even before smart interactive voice response (IVR) systems, there was Microsoft’s Office Assistant, one of the first widely deployed digital assistants that shipped as part of Microsoft Office in 1997. You might remember this feature better as the animated paper clip Clippy, even though Microsoft insists its (his? her?) official name is ClippIt. Doesn’t ring a bell? How about this: “It looks like you’re writing a letter”? Even though Microsoft officially retired Clippy in April 2011, the character continuously resurfaces as a meme in the zeitgeist. Try https://www.reddit.com/r/Clippy/ to see an assortment. Or check out Microsoft Cloud Developer Advocate Chloe Condon’s business card in her tweet (one of our inspirations for making this history): https://twitter.com/chloecondon/status/1098732324622020609?lang=en In this episode, a16z Board Partner and longtime Microsoft executive Steven Sinofsky shares his personal remembrances of Clippy with a16z Operating Partner Frank Chen. They discuss these and many more vignettes from the history of Clippy: - What problem the newly formed Microsoft Office team was trying to solve: https://youtu.be/8bhjNvSSuLM?t=129 - Which Stanford University and Microsoft Research ideas informed the design of the feature: https://youtu.be/8bhjNvSSuLM?t=396 - How the project was approved, what size team worked on it, and what BillG thought of it (warning: f-bomb ahead!): https://youtu.be/8bhjNvSSuLM?t=1121 - What user testing the team did on both the look-and-feel of the feature, as well as the cast of characters that ended up in the gallery (dolphins! geniuses not named Einstein! leprechauns!): https://youtu.be/8bhjNvSSuLM?t=2155 - How a pair of legendary Disney animators inspired the "stage" the characters perform on: https://youtu.be/8bhjNvSSuLM?t=1944 - How the feature got launched and marketed, and early reactions from users and reviewers: https://youtu.be/8bhjNvSSuLM?t=2851 - How Clippy got an elaborate real-world retirement party in San Francisco, complete with a blues song: https://youtu.be/8bhjNvSSuLM?t=3427 - Watch Clippy featured on Conan O'Brien's late night TV show: https://youtu.be/8bhjNvSSuLM?t=3927 - What Clippy can tell us about the future of digital assistants: https://youtu.be/8bhjNvSSuLM?t=4030 - The nature of risk-taking in software product development: https://youtu.be/8bhjNvSSuLM?t=4424 Enjoy watching the full arc of Clippy's life from prototype to retirement to cultural meme. *** The views expressed here are those of the individual AH Capital Management, L.L.C. (“a16z”) personnel quoted and are not the views of a16z or its affiliates. Certain information contained in here has been obtained from third-party sources, including from portfolio companies of funds managed by a16z. While taken from sources believed to be reliable, a16z has not independently verified such information and makes no representations about the enduring accuracy of the information or its appropriateness for a given situation. This content is provided for informational purposes only, and should not be relied upon as legal, business, investment, or tax advice. You should consult your own advisers as to those matters. References to any securities or digital assets are for illustrative purposes only, and do not constitute an investment recommendation or offer to provide investment advisory services. Furthermore, this content is not directed at nor intended for use by any investors or prospective investors, and may not under any circumstances be relied upon when making a decision to invest in any fund managed by a16z. (An offering to invest in an a16z fund will be made only by the private placement memorandum, subscription agreement, and other relevant documentation of any such fund and should be read in their entirety.) Any investments or portfolio companies mentioned, referred to, or described are not representative of all investments in vehicles managed by a16z, and there can be no assurance that the investments will be profitable or that other investments made in the future will have similar characteristics or results. A list of investments made by funds managed by Andreessen Horowitz (excluding investments and certain publicly traded cryptocurrencies/ digital assets for which the issuer has not provided permission for a16z to disclose publicly) is available at https://a16z.com/investments/. Charts and graphs provided within are for informational purposes solely and should not be relied upon when making any investment decision. Past performance is not indicative of future results. The content speaks only as of the date indicated. Any projections, estimates, forecasts, targets, prospects, and/or opinions expressed in these materials are subject to change without notice and may differ or be contrary to opinions expressed by others. Please see https://a16z.com/disclosures for additional important information.