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#055 | An Easier Way to Run Your Business (and Manage Your Podcast) with Wailin Wong, Co-Host of The Rework Podcast

Date : September 29, 2017 Posted By :James Martell

The Rework PodcastIn this edition of the Podcasting Mastery podcast, your host James Martell, is joined by Wailin Wong, Co-Host and Co-Producer of The Rework Podcast to talk about A Better Way to Work and Run Your Business. The Rework Podcast is a business show by Basecamp, a Chicago based Software Company whose founders wrote the best selling 2010 business book, Rework. William Taylor, founder of Fast Company magazine said, “The brilliance of Rework is that it inspires to rethink everything you thought you knew about strategy, customers and getting things done.”

How Basecamp started its Podcast, The Distance

At the end of 2013 Jason Fried, Co-founder of Basecamp brought Wailin on board at the time he wanted to launch a long form written publication like an online magazine about independent privately held old businesses that were at least 25 year old, that had never taken outside investment. The thinking behind that was to lift up entrepreneurs and start up founders, as these demigods of business figured it all out and they’re growing their business and they’re wildly successful. But they are unheralded, they’re the unsung heroes of the business world because they’re just being heads down working and they’ve been building life style businesses which are sometimes looked down upon in other corners of the business world.

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Jason wanted Wailin to write these well reported long form features about these businesses and about a year into that, they decided to test out audio as there was a lot of enthusiasm around podcasts. So they switched to podcasting, also having understood why podcasters are the new influencers and started The Distance.

The Rework Podcast and its Launch

Just earlier this year, Jason was ready to see if they could take what they had learnt about podcasting and apply it to a different kind of show. Launch a new show and get everybody excited about something different, and do a show that would take the themes from the book Rework. They wanted to increase listener interaction in the process.

ReworkThe Rework podcast interviews small business owners and also people who work at Basecamp including the company’s founders. Their ideal listener is a small business owner or an aspiring entrepreneur, podcaster or someone who wants to work smarter or saner within the company. Wailin sat down with a copy of Rework and pulled out all the themes to build the episodes around. The book was found to be a really good framework for telling interesting personal business stories that all relate back to the Basecamp philosophy. These stories illustrate Basecamp principles in action and it’s kind of getting the Basecamp philosophy out there but in a useful way.

But they’re not totally beholden to following the book page by page; if there’s interesting topics that come out that fit in the Basecamp wheelhouse, they have complete flexibility to build an episode around that. They recently had an episode out, where Wailin interviewed the Co-Founder David Heinemeier Hansson about fighting on Twitter and there’s no chapter in Rework about fighting on Twitter. They also have illuminating conversations about all sorts of things; online debates and what it means to have extreme voices and other stuff.

Listen now as Wailin shares:

  • How they turned the Rework book into a podcast
  • How Basecamp was started
  • The counter narrative nature of Basecamp, against an idea that is popular in Silicon Valley
  • Benefits that come along with staying small
  • How James Martell found Basecamp exactly at the time he needed it most
  • The Poisonous effects of immediacy in a workplace
  • How workplace meetings can be toxic
  • Basecamp’s philosophy of having smaller customers
  • Benefits of embracing simplicity which is a big theme in Basecamp
  • Success stories of Basecamp from the clients’ side


If you’re looking for a better way to work and run your business, while the prevailing successful entrepreneurship tells you to scale fast and raise money, check out podcasts by Basecamp that bring you stories from business owners who have embraced bootstrapping, staying small, and growing slow.

James’ Books on Podcasting

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