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Free to Work: Andrew Crapuchettes on Building Pro-Freedom Workplaces in Today’s Economy
The Joy of Living Podcast with Barry Shore
Free to Work, Free to Thrive: Andrew Crapuchettes on Purpose-Driven Business, Courage at Work, and Building RedBalloon
What if work wasn’t just about a paycheck—but about purpose, freedom, and becoming your best self?
In this powerful and soul-stirring episode of The JOY of LIVING, Barry Shore sits down with serial entrepreneur and cultural innovator Andrew Crapuchettes, the founder of RedBalloon.work—America’s leading pro-freedom job board. From being labeled a failure in kindergarten to building companies that bless entire communities, Andrew’s story is one of grit, grace, and conviction.
They dive deep into the future of work, the dignity of labor, and why standing up for your values in today’s climate is an act of leadership. Andrew shares hard truths from the front lines of hiring, courageous stories of transformation, and a blueprint for building businesses that bless everyone involved—customers, employees, and investors.
If you’re tired of workplace politics, hungry for meaning in your career, or curious how capitalism can actually heal, this episode will expand your mind and touch your heart.
Listen closely—this isn’t just a conversation, it’s a movement.
You’ll Discover:
- Why Andrew believes work is good for the soul—and how to reclaim joy at work
- The secret behind RedBalloon’s explosive growth—and the lives it’s changing
- How gossip-free cultures supercharge innovation and retention
- What happened when one executive was punished for displaying an American flag
- Why courage is contagious—and why now is the time to live your values out loud
- The three blessings that should guide every business decision
- And the deeply personal legacy Andrew hopes to leave for generations to come
Let this episode remind you: when you live with purpose and choose to serve others, joy finds you—and stays.
Share it with someone who’s ready to break free and find meaningful work.
Listen Here (click here to watch episode)
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Show Notes:
[10.00] From Kindergarten Rejection to Tech Success
- Andrew shares how his kindergarten teacher labeled him a lost cause—setting the stage for a lifelong journey of resilience and reinvention.
- Homeschooled by a mom who believed in him, he nurtured a love for jokes, learning, and defying expectations.
- He chased the dot-com dream—traveling globally and grinding 80-hour weeks by age 22, only to realize success without balance is empty.
- A decision to leave the Bay Area for rural Idaho wasn’t just about geography—it was a pivot toward purpose.
- When his company shut down, Andrew didn’t just find a new job—he built new companies to create jobs for others.
- His labor market data company sought to empower people with career clarity—helping them navigate economic decisions with precision.
- Andrew’s first business goal? Get 50 locals in his small town earning over $50K—a mission of real-world impact rooted in dignity through work.
[17.30] Purpose, Capitalism, and the Birth of RedBalloon
- Barry and Andrew unpack the moral beauty of “conscious capitalism”—business as a vehicle for creating prosperity and purpose.
- Barry’s childhood snow-shoveling story becomes a metaphor for service-driven entrepreneurship: put “you” before “I” in “business.”
- Andrew’s passion to scale impact sparks the creation of RedBalloon—a pro-freedom job board with a values-first ethos.
- Naming it “.work” instead of “.com” wasn’t just branding—it was a statement against the creep of collectivism into free enterprise.
- RedBalloon is more than a job site—it’s a lifeline for people who want to work with joy, purpose, and freedom.
- From helping 1,000 to helping millions—Andrew’s dream is fueled by the belief that dignity and prosperity go hand in hand.
- He believes that hard work, not handouts, is what gives life meaning—and RedBalloon is built to restore that principle to the workplace.
[26.00] Freedom to Work: A RedBalloon Revolution
- A hot air balloon ride becomes the perfect metaphor for today’s job search—quiet, directionless, and vulnerable to unseen winds.
- RedBalloon flips the script: it gives job seekers direction and dignity by connecting them with employers who honor merit over politics.
- Employers frustrated by DEI mandates and woke culture find a sanctuary at RedBalloon—where values and performance matter most.
- The platform now hosts millions of job seekers and thousands of pro-freedom employers nationwide.
- Andrew describes getting daily thank-you notes—testimonies of lives changed, marriages saved, and joy restored through meaningful work.
- It’s not just a job—it’s the chance to thrive in a place where you don’t have to check your beliefs at the door.
- RedBalloon isn’t about rebellion—it’s about restoring sanity, honor, and joy to the American workplace.
[33.00] The Three Blessings That Build Culture
- Andrew’s businesses run on a principle-driven framework: bless customers, bless employees, and then bless shareholders.
- Real leadership means pouring into people—not extracting from them—and cultivating cultures of trust and growth.
- A struggling sales rep was told to stop selling and start blessing—and in doing so, became a top performer.
- Gossip is outlawed in Andrew’s companies; instead, direct, respectful feedback is the norm, leading to innovation and safety.
- When employees know they’re being invested in, not just used, they show up with loyalty and energy.
- The result? Off-the-charts retention, high performance, and a deep sense of shared mission.
- Biblical principles like honoring authority, blessing others, and choosing honesty shape not just policy—but culture and outcomes.
[42.00] Courage, Conviction, and the Future of Work
- Stories pour in from workers freed by RedBalloon—like the Microsoft exec rebuked for having an American flag background on Zoom.
- The tyranny of silence is real—but courage is contagious, and one person speaking up can awaken an entire office.
- RedBalloon helps employers avoid hiring lawsuits and culture clashes by matching them with values-aligned, high-integrity talent.
- With a 90%+ success rate, their recruitment service delivers quality, fit, and peace of mind—at a flat, fair price.
- Barry calls Andrew an “SOB”—a Source Of Blessing—and it’s not a joke: RedBalloon is restoring humanity to hiring.
- Work should be more than a paycheck; it should be a place where you bring your whole self and grow into your best self.
- Andrew’s fervent desire? That his kids and grandkids remain faithful, resilient, and driven to do even more good than he ever could.
Insider Tips:
Nicole Iny is the Executive Director of Grants and Consumer Education at FAIR Health, a national, independent nonprofit organization that qualifies as a public charity under section 501(c)(3) of the federal tax code. FAIR Health possesses the nation’s largest collection of private healthcare claims data, which includes over 47 billion claim records. It is dedicated to bringing transparency and integrity to healthcare costs and health insurance information through data products, consumer resources and health systems research support.
Topics:
- What is FAIR Health?
- What types of tools and resources are offered on FAIRHealthOlderAdults.org?
- What obstacles do older adults and family caregivers face when navigating the healthcare system, and what strategies can they use to find the services and support they need?
- Have you received any feedback from patients and/or their caregivers about the shared decision-making resources available on the FAIR Health consumer website?
- Where can patients, family caregivers and healthcare providers find more information?
Important Links:
About Andrew Crapuchettes
Mr. Crapuchettes began his career as a young Silicon Valley entrepreneur, building business process automation and selling 3D modeling software.
In 2001, Mr. Crapuchettes became a founding member and later CEO of Emsi (now Lightcast), which he transformed from a little-known consulting company of three employees to an international economic data firm with over 250 employees worldwide.
Mr. Crapuchettes not only pioneered the operational tenets that rocketed Emsi to success, but led the company through four successful transitions to two private equity firms, a strategic buyer, and a national non-profit, with each transition producing significant returns for the investors.