Taking Chances with Shaun Coe
Taking Chances with Shaun Coe
Shaun Coe
Taking Chances Returns: Entrepreneurship, Instawork & the Future of Work
47 minutes Posted Nov 22, 2025 at 12:00 am.
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Taking Chances is back — and it’s evolving.

In its first run, the show highlighted people willing to bet on themselves.


From here on out, Taking Chances is a show about entrepreneurs, for entrepreneurs — the builders and operators reshaping how we work.

In this first episode back, host Shaun Coe sets the stage with his own journey: relocating from Europe back to the U.S., getting married, living through two hurricanes and four moves, and stepping into his role as CEO and founder of HC-Resource and Ascendium Tech. That chaos, resilience, and reinvention frame a new, sharper focus on entrepreneurship, staffing, AI, and the labor market.

To bridge the past and the future of the show, Shaun brings back Jeremy Friedman of Instawork — a leading tech-based staffing marketplace — for a candid conversation on how recruitment and hourly work are being rebuilt in real time.

They dive into:

  • How Instawork built a tech-first staffing marketplace and workforce solution
  • Where AI, automation, and smarter vetting are changing recruitment speed and quality
  • Why “the system is broken” for both workers and employers — and what it looks like to fix it
  • The role of feedback loops in improving the experience for workers, operators, and platforms
  • The rise of flexible scheduling and what today’s workforce is really asking for
  • How Ascendium Tech is designing tools to automate hourly recruiting at scale
  • Why informed consent and transparency will define the future of recruitment

If you’re an entrepreneur, founder, or operator in staffing, HR tech, or workforce solutions, this episode is your on-ramp into the new era of Taking Chances — and a preview of where the labor market is headed.

Follow the show, share this episode with a fellow builder, and tap into the community we’re creating to fix what’s broken in work.