GOING BIG! WITH KEVIN GENTRY
EPISODE SUMMARY
Going Big with Bo Ghirardelli & Nicolas Cary: Sky’s the Limit and the American Dream
February 23, 2026

Episode Overview

This episode of Going Big! features a dynamic conversation between host Kevin Gentry and guests Bo Ghirardelli and Nicolas Cary—co-founders of Sky’s the Limit, a digital platform designed to empower low-income, early-stage entrepreneurs with the tools, mentorship, and capital needed to start and grow their businesses. Together, they explore the crisis in the American Dream, the roots and growth of Sky’s the Limit, disruptive forces like AI and crypto, and the transformative power of mentorship and entrepreneurship.

Main Topics & Key Discussion Points

1. The Origins and Mission of Sky’s the Limit

• Bo Ghirardelli introduces Sky’s the Limit as “a digital success platform for low-income, earliest stage entrepreneurs, connecting them with education, networks and capital.” (03:16)
• The initial inspiration: Bo’s Peace Corps experience in Morocco during the Arab Spring, where he was confronted with high unemployment and people with untapped entrepreneurial potential.

  “There wasn't a good place for folks to turn to, to learn about how to start a business... millions of people have talent but don’t know how to channel it into building a business.” (04:07–05:30)

• Demand for entrepreneurship support in the U.S. mirrored international needs; struggles of access, knowledge, and capital are universal.

2. The Problem: Declining Faith in the American Dream

• Nick Cary articulates the broader challenge:

  “People are losing faith, I think, in their ability to succeed on their own merits. And we want to intervene right there at the earliest stages of their entrepreneurial journeys to be partners with them, to be support for them, and ultimately to help them achieve their potential.” (07:39)

• Cites statistics reflecting wealth insecurity and the first generation of Americans with less optimism than their parents.
• The convergence of AI-driven labor disruption, systemic inequalities, and lack of entrepreneurial support.

3. Founders' Backgrounds and Motivations

• Nick’s Story: Grew up with early entrepreneurial ventures (collecting and selling clams at age 13), development of Blockchain.com, and a deep-seated belief in entrepreneurship as empowerment.

  “I believe [entrepreneurship] to be an extraordinary empowering mechanism for people's personal agency...” (18:46)

• Has personally pledged over half of his shares in Blockchain.com to supporting the cause of entrepreneurship.
• Bo’s Story: Multigenerational entrepreneur, influenced by family dinner-table conversations and a focus on purpose; passionate about channeling entrepreneurship toward societal good.

  “That upbringing...focused on living for something greater than yourself. Purpose was a big deal... Sky’s the Limit is an amalgamation of two passions: entrepreneurship and making a difference.” (23:05)

• Brief family history and mythos: descendant of the founder of Ghirardelli Chocolate company, but the family sold it generations ago.
• Emphasis on spending resources for impact, not just personal gain.

4. The Solution: How Sky’s the Limit Works

• Sky’s the Limit started as a brick-and-mortar operation but pivoted to digital after seeing overwhelming demand.
• Combines three core offerings:
  • Entrepreneurial Education: Missions-based, gamified learning accessible anytime.
  • Mentorship & Coaching:
    • Volunteers from leading partner corporations (Accenture, Wells Fargo, etc.).
    • “We’re looking for two types of people: aspiring entrepreneurs and volunteers who want to mentor and advise them.” (30:24)
  • Access to Capital: Pitch competitions, grants, and support, especially for those overlooked by traditional banks.

5. The Power and Process of Mentorship

• Mentorship is central:
  • Bo credits mentors (family, board members, industry leaders like Fabio Rosati) as key to growth and inspiration.
  • Nick:

    “With a mentor, it's almost more like I want to discover something about myself. That requires a relationship where there's a lot of vulnerability... what do they stand for? How do they behave when people aren't looking... what's their character?” (38:40)

  • Distinction between teachers (knowledge transmission) and mentors (personal discovery).
  • Sky’s the Limit applies group events, algorithmic matching, and direct messaging to connect participants and mentors at scale.

    “Finding the right person at the right time is the problem to solve... magic happens, but you gotta work for it.” –Bo (41:47)

6. Leadership, Resilience, and the Entrepreneurial Ethos

• Nick:
  • Good mentors are guides, not prescribers.
  • Entrepreneurship is hard regardless of scale, requiring persistence and a customer-first ethical mindset:

    “I like to describe it as the business code of ethics... always take care of your customer and take care of your customer first.” (45:00)

7. Impact Stories

• Bo shares the story of Brianna:
  • A mission-driven entrepreneur who resurrected her mother’s popcorn company (Katrina’s Popcorn) to create meaningful employment for women who survived trafficking:

    “She's working on placing her popcorn inside... hotels so they can raise awareness about trafficking.” (46:18–48:29)

8. Vision for the Future: Crypto, AI, and Massive Scaling

• Cryptocurrency / Blockchain:
  • Nick, an early innovator in crypto philanthropy, envisions a democratized, decentralized financial system that remedies inequality, but acknowledges it will take a lifetime to achieve full adoption:

    “At the end of the day, just—I believe anyone in the world should be able to pursue entrepreneurship and the work Bo valiantly does... we keep working on this problem set...” (51:46 – 53:03)

• AI as a Tool and Threat:
  • Both see AI as a disruptive force for labor and recognize the need for entrepreneurs and non-profits to adopt AI to stay relevant.
  • Bo to his younger self: “You need to become an AI savant and you need to get on that ASAP...” (56:52–57:39)

9. Philanthropic Leverage, Efficiency, and Scale

• $25,000 enables support for about 370 entrepreneurs this year, a 17x efficiency compared to traditional brick-and-mortar nonprofit programs.

  “Each entrepreneur that we support...they're building products and services. They're going to touch the lives of dozens, hundreds, thousands of customers. The ripple effect is truly powerful.” –Bo (54:07–56:05)

10. Final Words of Encouragement

• Nick:

  “We think this problem is so big that it will require hundreds of millions and someday billions of dollars to intervene. And so we’re on a long-term mission... For anyone that looks up at the sky and sees a better future, we want them to sign up... we're all better off by trusting each other, growing together, and learning together.” (58:21)

• Bo to his younger self:

  • Double-down on messaging, partnership, and AI adoption.

• Nick to future entrepreneurs:

  • Seek community, mentorship, and take the leap—Sky’s the Limit is here to support that journey.

Notable Quotes & Memorable Moments

• “Everyone's chasing all these resume virtues all the time... but at the end of the day, what's put on your gravestone is really a lot more and speaks more to the quality of your character.” – Nick (00:01, reprised at 38:40)
• “We had over 5,000 applicants to our Oakland-based program... obviously, we can't serve 5,000 people from this brick-and-mortar operation — we need technology.” – Bo (28:36)
• “There's no university for entrepreneurship. The only way to learn is to go practice it in the wild, in the real world.” – Nick (30:10)
• “If you take this much risk on, there are big consequences. So make sure you consider a risk-adjusted approach to X, Y, and Z… But it doesn't have to be lonely.” – Nick (43:49)
• “Artificial Intelligence...there’s going to be some reckoning over the next few years.” – Nick (09:51)
• “Investing in an entrepreneur is an incredibly leveraged investment.” – Bo (54:31–56:05)
• “You need to become an AI savant...and leverage that tool to accelerate the impact you can have.” – Bo (56:52)

Timestamps of Key Segments

• [03:16] – Elevator pitch for Sky’s the Limit
• [04:07–05:30] – Story of the Morocco inspiration
• [07:39] – On declining faith in the American Dream
• [14:53–18:50] – Nick’s entrepreneurial and tech background
• [23:05–27:00] – Bo’s family history (Ghirardelli), path to purpose
• [28:36] – Moving from brick-and-mortar to digital
• [30:24] – How Sky’s the Limit works for users and mentors
• [38:40] – Nick’s philosophy on mentorship and character
• [41:47] – Scaling mentorship and matching
• [43:49] – Leadership, resilience, and mentorship nuances
• [46:18–48:29] – Brianna’s story: mission-driven entrepreneurship
• [49:22] – The promise and challenge of crypto adoption
• [54:07–56:05] – Philanthropic leverage and impact metrics
• [56:52] – Bo’s advice to his 18-year-old self: partnerships, clarity, and AI
• [58:21] – Nick’s closing encouragement: long-term vision and community

The Bottom Line

This episode is a compelling call to action—not just for aspiring entrepreneurs but for those who wish to support them. The conversation brings to light the scale of the opportunity gap, the need for scalable, tech-enabled solutions, and the indispensable role of mentorship, resilience, and purpose-driven leadership. Sky’s the Limit embodies a new approach: leveraging networks, technology, and philanthropy to democratize the pursuit of the American Dream.