The Unshakeables: “Full Court Vision: Round21”

Podcast: The Unshakeables (Chase for Business and iHeartPodcasts)
Date: December 16, 2025
Host: Ben Walter
Guest: Jasmine Maieta (Founder, Round21), Kathleen (co-host/interviewer)

Episode Overview

This episode features Jasmine Maieta, former pro basketball player and founder of Round21, an innovative sports/art brand. The discussion follows Jasmine’s journey from athlete and major sportswear executive to entrepreneur navigating boom-and-bust business models—including Web3, NFTs, and the mission-driven physical goods of today. Jasmine opens up about tough pivots, resilience, and the ongoing challenge of balancing bold innovation with practical business realities.

Key Discussion Points and Insights

Jasmine’s Athletic and Corporate Origins

• Jasmine’s identity was deeply rooted in basketball, influencing all aspects of her life (01:54).
• Transition from playing professionally in Spain to brand marketing roles at Reebok and Under Armour.
• Learned the value of authentic connection in corporate culture—“I was truly bonding with the senior leaders at Reebok playing pickup basketball.” (02:13, Jasmine)

Trends in Sportswear: Identity & Community

• Shift from product function (e.g., Under Armour’s performance tech) to products as expressions of identity and community.
• “They wanted to know, increasingly, not about the technology... They wanted to know what’s the story, what’s the colorway, who else is wearing this?” (03:04, Jasmine)
• At Peloton, Jasmine witnessed how a brand flourishes when the community becomes its defining feature.

Building Round21: Genesis & Vision

• During the pandemic, Jasmine acted on the “upside to try” (05:51), launching Round21 with the philosophy that sports objects (like ping pong paddles) could be canvases for art, starting with the NBA bubble season (07:11).
• “How do you create a category? Go somewhere people haven’t gone.” (07:34, Jasmine)

The Digital Pivot: Web3, NFTs, and Bored Ape Yacht Club

• Inspired by Clubhouse and the NFT craze, Jasmine engaged digital artists and communities, experimenting with the idea of digital-first collectibles tied to real-world products (08:28–09:02).
• “Purchase of that digital asset would give access to get that basketball in real life.” (09:02, Kathleen)
• Major success: $250,000 in sales in 7 days with the Bored Ape Yacht Club collab.
• “Let’s just do this 50 times a year.” (10:24, Jasmine)

The “Outrageous Ask” and Entrepreneurial Grit

• Jasmine was lauded for her courage in reaching out to big figures and brands, spurring a segment where Kathleen shares her own “outrageous ask” to Warren Buffett (12:08).
• Insight on entrepreneurial asks: balancing the “foot in the door” versus “door in the face” techniques (13:38, Ben)

Shark Tank & Dual Business Models

• Jasmine pitched on Shark Tank with her unique digital-physical model, finding validation for her vision (15:15).
• For a time, Round21 operated dual physical and digital businesses, emphasizing constant learning and adaptability.

NFT Crash, Sunk Costs, and the Difficult Pivot

• By 2022, heavy investment in Web3 and NFTs began to look perilous as the NFT market faltered (16:37).
• Despite strong community engagement, Round21’s future rested on its physical products and partnerships.
• Advised by her business-savvy cousin, Jasmine shut down the NFT side:
  • “If it’s not working, kill it.” (18:42, Jasmine quoting her cousin)
• Nearly $500,000 spent on the Web3 pivot—no regrets, only lessons learned.
• “What are you going to do with the information you have? ...I still don’t regret. I would probably do the exact same thing because of all of the lessons it taught us.” (19:53, Jasmine)

Lessons on Letting Go: Assets, Liabilities & Moving On

• Clear advice on differentiating assets vs. liabilities—don’t resuscitate failing projects just because of emotional attachment (20:32).
• Jessica’s biggest brand inflection points came from aligning product-market fit, e.g., WNBA partnerships.
• “When it doesn’t feel that way, it is a liability. And as a founder, understanding the difference between those two took me a very long time, but I’m finally there.” (21:54, Jasmine)

The Current Era of Round21

• "Era one was Web3, era two has been women’s sports, and now we’re on to era three, harnessing the creative side of sports." (26:00, Jasmine)
• Company reinvesting in people, process, and supply chain sophistication; staff of 11+.
• Laser focus on women’s sports and the WNBA as both a mission and a business driver (27:10).
• Innovation is tethered to genuine community curation: “We stay with the times—or ahead of trends, or create trends—through the art community.” (28:07, Jasmine)
• Jasmine likens Round21 to an art gallery, balancing curation and discovery for customers (29:38).

Notable Quotes and Memorable Moments

• “It was only upside to try, because if it failed, everybody was working from home anyway.”
  — Jasmine Maieta (05:51)

• “If it’s not working, kill it.”
  — Jasmine Maieta quoting her cousin (18:42)

• “Does that still hurt?” “No...I would probably do the exact same thing because of all of the lessons it taught us.”
  — Jasmine Maieta (19:49–19:53)

• “That failed. That experiment or pilot failed. You didn’t fail.”
  — Kathleen (25:46)

• “The advice I would give is that you understand your, like, immovable core...define your core but how you bring it to market being as open as your imagination because you just never know what might hit.”
  — Jasmine Maieta (30:36)

Timestamps for Key Segments

• Jasmine’s basketball/corporate backstory: 01:43–03:45
• Peloton, the power of community: 03:45–04:27
• COVID as tipping point for entrepreneurship: 05:09–06:07
• NBA bubble, ping pong paddles, first product: 06:48–07:25
• Web3 and Clubhouse inspiration: 07:58–08:28
• NFTs, Bored Ape Yacht Club partnership: 10:00–10:24
• Outrageous asks and making big pitches: 12:08–13:38
• Shark Tank & dual business models: 15:15–16:37
• NFT crash, tough decisions: 16:37–17:16
• Sunsetting digital business, sunk cost lessons: 19:44–20:32
• Turning point—WNBA partnership, product-market fit: 20:32–21:54
• Era Three: The Creative Side of Sports: 26:00–28:07
• Community art curation and scaling individuality: 28:07–30:27
• Final advice for entrepreneurs: 30:36

Final Takeaways

• Jasmine’s journey exemplifies entrepreneurial adaptability: knowing when to dive in fearlessly and, crucially, when to walk away.
• Emotional resilience is as vital as strategic insight—don’t let sunk cost or ego dictate your future moves.
• Focus on your core mission, embrace experimentation, and let your community help guide your evolution.
• Jasmine’s story shows that “failing” a business experiment doesn’t mean founder failure—but the courage to pivot can be your greatest asset.

This episode is a candid, inspiring look at risk, reinvention, and the power of believing in your vision—right up to the point where you know it’s time to build what’s truly next.