Ben Orenstein - From Developer To CEO of Tuple

[00:02:09] Ben takes us thorough his career journey starting off as a programmer.

[00:05:45] Ben explains how things have changed since he became a CEO and about the transition with Tuple. 

[00:06:35] Chris wonders if Ben’s had any struggles now that he’s interviewing and managing people, and he explains how he’s had to learn more in this process.

[00:09:12] Ben tells us how hiring and figuring out ways to document all the things they’ve been doing has been playing out.  

[00:10:56] Tuple is a mac app, but Andrew wants to know what the Rails app is doing in there, if it interfaces with the mac desktop client, and if there were any issues with the recent macOS Monterey upgrade. 

[00:13:33] Jason wonders if Ben misses coding, if he does any side projects to stay coding, and if he still does a lot of writing in vim. Also, Andrew tells us about Obsidian. 

[00:17:09] Jason brings up Ben’s Refactoring Rails Course.

[00:18:28] We hear Ben’s thought process and how he decided to start Tuple.

[00:22:17] Chris wonders if Ben considers Tuple as primarily marketing towards developers and peer programming.


[00:26:18] Since Ben is working on a Linux version for Tuple, he explains how much work goes into it. 

[00:30:05] Ben announces he’s looking to hire a Linux App Developer at Tuple and what led Ben to do Linux before Windows.

[00:34:41] Chris wonders if Ben is worried about the effect of speed of shipping new features with the growth of the product.


[00:36:46] Ben explains “shipping is less than you think you need to.” 

[00:41:48] Andrew brings up a guide that Ben wrote about why pairing is so important, and we hear Ben’s thoughts on pairing. 

[00:44:05] We hear about some cool things coming soon for Tuple, and if you’re interested in working for Tuple, Ben tells us the positions he’s looking to fill.

[00:46:25] Find out where you can follow and reach out to Ben online.


Jason Charnes

Chris Oliver

Andrew Mason


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Refactoring Rails Course

Jobs at Tuple

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