Q&A with Wailin Wong, Co-Producer/Host of The Rework Podcast

Q. You’ve been covering consumer technology and startups for over a decade — previously at the Chicago Tribune and now front and center producing Rework and as part of the Basecamp team. What are two or three distinct differences you’ve noticed about how they operate, how teams operate?

I was initially hired at the Tribune as the Motorola beat reporter. This was at a time when the company was undergoing continual upheaval and painful restructuring to find its footing after the mega success of the Razr. Motorola had the kind of cumbersome corporate structure that gets built up over decades of existence as a global publicly traded company and can become a problem. I wrote a story about what it took internally to produce the Moto X, a phone that was supposed to mark a rebirth for the company, and many employees talked about the struggle of taking a more creative and nimble approach to product development.

I then transitioned from covering Motorola to chronicling Chicago’s incipient startup scene, with Groupon as its (often reluctant or ambivalent) standard bearer. Groupon became a big public company, but from a culture perspective, it was almost the opposite of Motorola. It was goofy and weird! The co-founder and CEO gave wacky quotes! There was an urban legend about a guy named Michael who’d been living in the office before Groupon moved in and an actual “Michael’s Room” at Groupon’s headquarters furnished with a bed and an exercise bike that played Sade’s “Smooth Operator” when pedaled! I am not making any of this up.

It turns out that the companies I spent the most time thinking about during my time at the Tribune represented two ends of a spectrum. On one hand, there were legacy corporations with endless layers of bureaucracy and buttoned-up executives who often sounded like robots, and on the other hand there was a quirky online coupon company leading a local startup renaissance. In the middle were all kinds of startups that had a slightly different sensibility than their Silicon Valley counterparts, given their Midwestern roots, but that also adopted startup tropes like ping pong tables, hoodies, and bro-y social events.

To be fair, at Basecamp, we also have a ping pong table (currently folded up and unused) and hoodies, so we’re not entirely immune from the tech startup monoculture either. I’ve gotten to interview a range of business owners while producing The Distance and Rework for Basecamp, and it’s always good to talk to folks who are doing things a little differently (not chasing hyper growth and outside funding, for example) or who are outside tech altogether.

Q. Basecamp does so many things right when it comes to company culture. On a personal level, do you have a favorite aspect of the culture?

Jason and David are big believers in hiring managers of one — people who can work in a self-directed way. I love the independence I have. It’s reflected on a day-to-day level because I set my own hours, for example, and it’s also been a major part of my role here. When we decided to launch a new podcast, my co-producer and I were the ones who came up with the idea for Rework, and we’re given free rein on how the show sounds and the topics we cover. There’s no micromanagement or top-down editorial directives. It’s a daunting amount of creative and professional freedom, and I wouldn’t have been able to handle it at an earlier stage of my career, but now it’s hard to imagine working any other way.

Q. Do you have a favorite Rework podcast for the Culturati membership? What would be a good introduction for members who don’t know your work?

My favorite is Please Don’t Like This, which lays out an internal debate we were having at Basecamp over a feature in our software. I like it because it offers a lot of food for thought around social media gratification and the “gamification” of work, and also because I got to explore a weird rabbit hole involving the pianist Glenn Gould. Please Don’t Like This is a very Basecamp-focused episode, aside from the Gould stuff. For people looking for an episode that features more interview subjects outside the company, I’d recommend You Need Less Than You Think.

Q. Does anything about corporate culture strike you as “of the moment”? What do you see from a culture perspective that businesses now seem to care about?

I’ll bring this to an unpleasant place and say that the #MeToo movement continues to be very “of the moment,” although it’s difficult to say whether there’s meaningful progress being made. It shouldn’t end with a few high-profile firings and rolling out harassment training programs. Businesses that truly care about making workplaces safe, inclusive, and equitable should also look at closing the wage gap, for example, and improving policies around parental leave and how working parents are treated in general.

Q. We had a debate during the last Culturati Summit about how much team culture depends on face-to-face time. In preparing for the recent episode Temperature Check, what were the big takeaways for you on how remote teams succeed?

My big takeaway, and something I’d been thinking about even before producing the episode, is that you have to put in the work for thoughtful communication. This might sound kind of obvious — presumably very few companies would say they’re not thoughtful about communication — but among remote teams especially, it takes special effort to make sure everyone is being included and heard. It’s hard to be the lone employee in a certain time zone that’s far off from everyone else, for example. At any company, it can be hard to be a new employee or an introvert or the only person (or one of a few) who looks like you. These difficulties can get magnified at a remote company, so it takes deliberate steps to build an inclusive and honest culture. In the Temperature Check episode, both Sarah Park of MeetEdgar and Patrick Filler and Anitra St. Hilaire of Harvest share some very practical things their companies do to facilitate healthy communication.

Wailin Wong

Wailin is the Co-Producer/Host of The Rework Podcast, a podcast based on Jason Fried and David Heinemeier Hansson’s bestselling book of the same name. The themes in Rework are explored through interviews with people at Basecamp, as well as interesting small business owners who have embraced principles like bootstrapping, growing slow, and staying small. Rework releases new episodes every other Tuesday.

Before launching Rework in August 2017, she co-produced and hosted The Distance, a narrative podcast featuring the stories of privately held businesses that are at least 25 years old. (These businesses were not Basecamp customers.) The Distance started as longform written features, added a companion podcast and transitioned to a podcast-only format, releasing stories every two weeks. The Distance was a finalist for the Chicago Headline Club’s 2017 Peter Lisagor Awards, honoring the best in Chicago journalism.

Before joining Basecamp to launch The Distance, Wailin was a business reporter at the Chicago Tribune for six years, covering consumer technology and local startups.

She started her career writing about emerging market economies and Latin America for Dow Jones Newswires in Buenos Aires, Argentina and New York.

Wailin has a BSJ and MSJ from Northwestern University’s Medill School of Journalism and lives in the Chicago area.

Wailin Wong interviewing Patagonia’s Dean Carter and the Obama Foundation’s David Simas (Culturati Summit 2018)




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Culturati Team

Culturati Team

Culturati is a community of CEOs, entrepreneurs, investors and other c-suite leaders who practice & study culture building and share our play books.

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