Workwhile & The Future of Fractional Work | BOSS MODE #020
Wed Jan 28 2026
What if the biggest shift in labor isn't AI replacing workers—but workers finally owning their time? Jarah Euston, CEO of Workwhile, joins your host David Lee, Cofounder of Vanka AI to challenge everything we think we know about employment, from why your employer is holding an interest-free loan of your paycheck to why 80 million Americans working frontline jobs have never had more choice.
This conversation digs deep into the fractional labor revolution, the $800 billion payday loan trap, why CEOs might be replaced before warehouse workers, and what "ownership" really means when your only capital is your own energy and attention.
🔗 Workwhile: https://workwhile.ai
🔗 RISE Pay Index: https://workwhile.ai/rise
🔗 Learn more about Vanka AI: https://vanka.ai
CHAPTERS:
0:00 – Introduction: The tailwinds for blue-collar work
1:30 – What is Workwhile? 1.2M workers, 8M labor hours, zero recruiters
4:45 – Why CEO jobs might be replaced before warehouse workers
6:26 – The shift from salary mindset to ownership mindset
8:08 – What frontline workers actually experience (the point system)
9:45 – Why tech founders don't build for hourly workers
12:18 – "Unemployment Is Dead": The end of one person, one job
14:17 – Pushing back: Workers as owners of their own capital
17:06 – The limits of hourly pay: External factors and market swings
19:09 – Why flexibility alone isn't enough—income adequacy matters
21:40 – The case for simple ownership: Start a dog walking business
24:01 – From Workwhile earnings to buying an Airbnb
25:34 – Challenging the "ownership is hard work" assumption
27:40 – Creativity and depression: Why humans need to create
29:06 – Should workers invest in businesses or index funds?
31:01 – AI-driven efficiency: Eliminating recruiters, reducing waste
34:21 – The payday loan trap: $800B in interest from delayed pay
36:37 – Who's the real villain: Employers or payday lenders?
38:18 – The "In Time" dystopia: Limits of instant pay
41:26 – Forced savings vs. property rights: A philosophical debate
44:45 – The connected C-suite: Blue-collar roots in leadership
48:10 – The 3.5% float: Should it be a line item on paychecks?
52:24 – "You gotta use your own product": Jarah works shifts
54:45 – Creative destruction: AI will create more jobs than it destroys
58:32 – What jobs will AI create? The honest answer: We don't know
1:00:59 – Human provenance: The premium market for craftsmanship
1:02:08 – Hot take: White-collar workers are the tiny minority
1:04:42 – Blue-collar automation is coming faster than we think
1:07:35 – There won't be one solution—all things will be true
1:09:47 – The broader answer: Ownership as the path forward
#futureofwork #bluecollar #labormarket #fractionalwork #Workwhile #AI #entrepreneurship #ownership #gigeconomy #bossmodepodcast #vankaai
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What if the biggest shift in labor isn't AI replacing workers—but workers finally owning their time? Jarah Euston, CEO of Workwhile, joins your host David Lee, Cofounder of Vanka AI to challenge everything we think we know about employment, from why your employer is holding an interest-free loan of your paycheck to why 80 million Americans working frontline jobs have never had more choice. This conversation digs deep into the fractional labor revolution, the $800 billion payday loan trap, why CEOs might be replaced before warehouse workers, and what "ownership" really means when your only capital is your own energy and attention. 🔗 Workwhile: https://workwhile.ai 🔗 RISE Pay Index: https://workwhile.ai/rise 🔗 Learn more about Vanka AI: https://vanka.ai CHAPTERS: 0:00 – Introduction: The tailwinds for blue-collar work 1:30 – What is Workwhile? 1.2M workers, 8M labor hours, zero recruiters 4:45 – Why CEO jobs might be replaced before warehouse workers 6:26 – The shift from salary mindset to ownership mindset 8:08 – What frontline workers actually experience (the point system) 9:45 – Why tech founders don't build for hourly workers 12:18 – "Unemployment Is Dead": The end of one person, one job 14:17 – Pushing back: Workers as owners of their own capital 17:06 – The limits of hourly pay: External factors and market swings 19:09 – Why flexibility alone isn't enough—income adequacy matters 21:40 – The case for simple ownership: Start a dog walking business 24:01 – From Workwhile earnings to buying an Airbnb 25:34 – Challenging the "ownership is hard work" assumption 27:40 – Creativity and depression: Why humans need to create 29:06 – Should workers invest in businesses or index funds? 31:01 – AI-driven efficiency: Eliminating recruiters, reducing waste 34:21 – The payday loan trap: $800B in interest from delayed pay 36:37 – Who's the real villain: Employers or payday lenders? 38:18 – The "In Time" dystopia: Limits of instant pay 41:26 – Forced savings vs. property rights: A philosophical debate 44:45 – The connected C-suite: Blue-collar roots in leadership 48:10 – The 3.5% float: Should it be a line item on paychecks? 52:24 – "You gotta use your own product": Jarah works shifts 54:45 – Creative destruction: AI will create more jobs than it destroys 58:32 – What jobs will AI create? The honest answer: We don't know 1:00:59 – Human provenance: The premium market for craftsmanship 1:02:08 – Hot take: White-collar workers are the tiny minority 1:04:42 – Blue-collar automation is coming faster than we think 1:07:35 – There won't be one solution—all things will be true 1:09:47 – The broader answer: Ownership as the path forward #futureofwork #bluecollar #labormarket #fractionalwork #Workwhile #AI #entrepreneurship #ownership #gigeconomy #bossmodepodcast #vankaai