Episode Description: Holly Diamond arrived in New York with $400 and a dream, faced the heartbreak of job searching during the 2009 recession, and eventually opened a restaurant during the pandemic to employ her parents. Now she's the CEO of Work Onward, a map-based hiring platform connecting small businesses with local workers, especially in immigrant-owned businesses and blue-collar industries.
What You'll Learn:
How to turn personal struggles into scalable solutions
The power of taking action before you feel ready
Creating dignity in employment for overlooked populations
Building technology that serves vulnerable communities
Balancing profit with social impact in business
Key Timestamps:
[00:00] Introduction and Holly's nomination
[01:30] What is Work Onward and how it works
[04:30] The restaurant origin story during COVID
[10:45] Holly's "Just Do It" philosophy
[12:30] The concept of dignity in employment
[18:30] Self-care and taking care of your wellbeing
[24:15] Who Holly nominates for the show
Key Takeaways:
Sometimes the craziest-sounding decisions are exactly what the moment requires
Your personal struggles can become your professional superpowers
Technology should make opportunities visible, not create more barriers
Dignity in work starts with how we see and treat each other
Community and collaboration are essential for creating lasting change
Resource Links:
Work Onward: [Platform information]
Holly's Restaurant: [Location details]
Connect with Holly: [Professional contact information]
Guest Bio: Holly Diamond is the CEO of Work Onward, a map-based hiring platform that connects small businesses with local hourly workers. Originally from South Korea, she moved to New York in 2009 and has spent over 10 years as a recruiter specializing in blue-collar industries. In 2020, she opened a restaurant to employ her parents during the pandemic, which became the inspiration for Work Onward's mission to create more inclusive hiring practices.
Host Bio: Aransas Savas is a researcher, coach, and host of The Uplifters Podcast. Connect with her:
Instagram: @aransas_savas
Podcast Instagram: @the_uplifters_podcast
TikTok: @theuplifterspodcast
Website: www.theuplifterspodcast.com
Keywords: career transition, immigrant entrepreneurs, job search platform, social impact business, small business hiring, dignity in work, pandemic pivots, family entrepreneurship, tech for good, inclusive hiring












