RE #164: Chris Herd & Jonathan Wasserstrum - A Conversation on Remote Work - Pros & Cons


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By Chris Powers. Discovered by Player FM and our community — copyright is owned by the publisher, not Player FM, and audio is streamed directly from their servers. Hit the Subscribe button to track updates in Player FM, or paste the feed URL into other podcast apps.

Chris Herd is the Founder & CEO at Firstbase, which helps companies build infrastructure with a remote-first mindset. He takes the side of remote work being most beneficial in the future of work.

Jonathan Wasserstrum is the Co-Founder and CEO of SquareFoot, which helps companies find commercial real estate and office space. Jonathan takes the side of in-person work being most beneficial in the future of work.

On this episode, Chris Powers moderates a debate between Chris Herd and Jonathan about which method of running business will lead to greater levels of success. Enjoy!

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Jonathan on Twitter

Chris Herd on Twitter

(02:51) - Jonathan and Chris’ Background and What They’re Doing Today

(05:00) - What does remote work mean to each of you and how do you think about the concept?

(10:09) - Jonathan - Do you define SquareFoot as a remote-first or office-first company?

(12:07) - How are leaders deciding whether they’ll be an office or remote company?

(16:36 ) - Trust Between Employers and Employees

(18:56) - What’s the Cadence of Coming Together as a Team and Being Able to Work Remotely

(25:40) - How does size or prestige of a company impact the ability of employees to influence the decision on remote vs. in person?

(31:20) - Is there any danger to your long term career-worth by choosing to leave a company that’s mandates in-office work?

(35:47 ) - Relationship/Friendship Building In-Office vs. Remote

No Rules Rules by Reed Hastings

(46:27) - What are the signals or data points to see what matters in either taking a company remote or discovering how much time is ‘needed’ in-office over the next 5 years?

(51:03) - Where are a lot of these remote-radicals going to live and work?

(55:27) - Data on Where People Want to Start Technology Companies Pre and Post Covid

(1:01:19) - How do you think about the next generation of workers coming out of school and only understanding a remote-work life. Do they miss out on mentorship or human interaction?

(1:10:08) - How do promotions get delegated on in-person workers and remote?

(1:11:43) - Trust and Tracking within Remote Companies

(1:16:25) - Wrap Up & Closing Statements

The FORT is produced by Straight Up Podcasts

177 episodes