There are plenty of podcasts that will tell you how the latest tech gadget or “innovation” will affect the tech landscape tomorrow, but there aren’t that many concerned with the potential impact of that tech in a decade—much less a century. In a culture obsessed with now, how can we make choices with a view for tomorrow, next year, and beyond?

Winning Slowly ran for 9 seasons from 2014–2020. It might come back someday!

Indefinite Hiatus


The Hosts

Chris Krycho is a software engineer, podcaster, writer, and occasional composer. He lives with his family in Colorado.

Stephen Carradini is a digital media scholar and professor, writer, editor, and songwriter. He lives with his family in Arizona.


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Previous Seasons

Season 8: The Winning Slowly Epistemology Book (and Film) Club →

A whole series dedicated to discussing books! We’d pick out highlight episodes, but… really, this whole thing was an enormous amount of fun.

The big idea: read widely—everything from Plato to Ray Kurzweil, from Jurassic Park to Ursula Franklin, from analyzing technology’s connection to race to gushing about Zeynep Tufekçi, and not least wrapping up with Robin Sloan’s delightful Mr. Penumbra’s 24-Hour Bookstore.

Season 7: Tech Criticism… and Hope →

If we’re going to avoid the “inevitable” future (as we talked about in Season 6) we need to be able to imagine a better one. That means rejecting techno-utopianism and techno-despair. In Season 7, we took a swing at doing just that—by way of small interventions, friction, and policy statements, among other things. We even tried a grand experiment in imagining a non-technocratic future!

We concluded the with a meta-discussion of the limits of our approach. In the end, we argue that while some technology problems can be greatly improved through improved ethics and wise actions, all problems of technology go deeper than just technology alone.

The essential episodes:

Season 6: Rejecting the Inevitable Future →

We are often told that particular visions of the future are inevitabilities. We have long said: not so! And here we took on the task of articulating when and how we might reject some of the technologies profferred by Silicon Valley giants and prognosticators of the future.

The absolute essentials:

Season 5: Structure and Agency →

A deep dive on the "structure/agency" problem, or: how individuals and systems relate. This one had a quirk to it, though: we recorded the first nine episodes in the fall of 2016, then the last three in the fall of 2017. (Stephen finishing his Ph.D. and moving across the country, and Chris finishing his M. Div. and moving across the country... had consequences.)

Episodes of particular interest include:

Season 4: Globalization →

In our spring 2016 season, we took a long look at globalization: the good, the bad, the ugly. This was also the first time we planned a season start to finish before we kicked it off, and it shows.

We talked about everything from international business (4.08: A Ghost in Singapore) to Star Wars (4.03: The Podcast Awakens and 4.04: But Was It a Good Movie?) and from social media in a populist era ( 4.10: The Ancient Wisdom of Usenet) to the challenges of global benevolence ( 4.01: Unambiguously Meh, 4.02: Helpiness, and 4.09: We’re Idealist Realists)

Along the way, we developed an important distinction between the reasonable and the justifiable: a way to help us bridge the gap with people we disagree with, while still disagreeing with them—sometimes fervently.

Season 3 →

Season 3 was our first attempt at doing a more topical season, with an emphasis on the relationship between advertising, business interests, and capitalism and human flourishing.

We kicked off the season with 3.01: The Ad-Driven Web, Part I and 3.02: The Ad-Driven Web, Part II on July 21 and 28, 2015, respectively, and concluded with some lightning round-style episodes in 3.14: Smorgasbord, Part I and 3.15: Smorgasbord, Part II on October 27 and November 3, 2015, respectively. The season also included our first interview: 3.09: Many Beautiful Things, with Ryan O’Neal of Sleeping at Last.

Season 1 →

Our first “official” season—the one that was not a “beta”—started on July 15, 2014, with 1.01: Massive Emotional Contagion, and wrapped up with the release of 1.18: Keep On Keepin’ On on November 18, 2014.

The main hiccup in Season 1? Stephen’s audio. It varies like crazy week to week, for reasons that eluded us. We blame grumpy, grumpy gremlins.

Season 0: This Is In Beta! →

Our first season: “This is a beta; bear with us!”—in which we spent a few months just figuring out what we were doing, ran from January 28, 2014 until May 20, 2014. Seriously: we had no idea what we were doing; we just knew we had a good idea for a show and wanted to figure out how to make it work. There is good content here, but we have kept this around mostly for historical interest—it’s rough.

Episodes ranged in length from over 45 minutes to under 20 minutes as we figured out our approach to the show, solicited regular feedback, and general got a handle on the whole thing. By the final episode, 0.14: Deep In Their Bones, we had found our basic formula and settled into a nice rhythm, which we were then able to carry into Season 1.