The Remote Show · Tyler Sellhorn, Matthew Hollingsworth

Jesse Chambers, Founder and CEO at wrkfrce

·29 min·2 clips

Jesse Chambers discovered he was a remote worker when he realized the freedom and flexibility he required professionally.

Jesse Chambers brings a founder's origin story. After leaving San Francisco in early 2019 with his wife and dog, he started working full-time from a 27-foot Airstream and building wrkfrce around a plain belief: work should fit life better. Tyler Selhorn asks him to explain the company, then the excerpt turns to the pressure remote workers and hiring managers are feeling now. The target is fake flexibility. Jesse pushes back on companies that moved office habits onto screens and called it remote work, especially when that means eight or nine Zoom meetings a day. That version wears people down. He connects the strain to the great resignation, not as the only reason people leave, but as proof that workers are rethinking what they will put up with. Some people stayed in place during the pandemic for stability. Others, he says, are leaving because employers still have not offered the flexibility people now expect and feel they have earned. Balance keeps coming back. In Jesse's view, the pandemic made many professionals question whether career status should keep outranking wellness, family, and daily life. Tyler keeps the conversation inside remote work. Matt Mullenweg's remote-work levels give them a useful marker. Companies stuck at level one are not redesigning work. They are using remote tools as an office substitute. That matters for hiring. Jesse's warning is direct: employers that do not offer real flexibility may have a hard time keeping people. The close loosens up a bit when Tyler invites more woo-woo into careers, which fits the episode's belief that work can be more humane without becoming less serious.

As heard by us

A grounded case for remote work built around burnout, flexibility, and a founder story that makes the argument concrete.

Remote work here is treated less like a perk and more like a hiring and retention problem, with Jesse Chambers making the case from experience rather than theory.

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Why you'd press play

You want a clear, human case for remote work that ties flexibility to hiring, burnout, and retention.

Read the full recommendation in PlayNext →

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