Full Court Vision: Round21

Summary

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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)

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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.

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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).

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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)

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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

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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.

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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.

Transcript

[Ben Walter]

Jasmine Maieta is a former pro basketball player and a veteran of giant athletic companies like Reebok, Under Armour and Peloton. She also has another distinction.

[Jasmine Maieta]

I actually pitched the first Web3 brand on Shark Tank with digital physical products.

[Ben Walter]

Thanks to early success with $250,000 of sales in just seven days in partnership with NFT company Bored Ape Yacht, Jasmine spent six figures building out this website.

[Jasmine Maieta]

That looked like a metaverse where you could pull and drag and drop the rotating 3D objects.

[Kathleen]

And how much would you say you spent in aggregate on the Web three metaverse strategy?

[Jasmine Maieta]

Probably half a million dollars. And then it all came crashing down.

[Ben Walter]

Welcome to the Unshakeables from Chase for Business and Ruby Studio from iHeartMedia. I'm Ben Walter, CEO of Chase for Business. On the Unshakeables, we are sharing the daring moments of small business owners facing their crisis points and telling the stories of how they got through it. And Kathleen is here today. Now, I had a personal conflict, so Kathleen stepped in to interview our guest this time. And Kathleen, you're going to share Jasmine's story with us. So thanks for stepping in.

[Kathleen]

I'm no Ben, but I had a.

[Jasmine Maieta]

Good time with her.

[Ben Walter]

Ye I thought you guys would hit it off and I listened to the episode. I thought it was terrific. So let's get going on today's episode. Round 21 from Washington D.C.

[Kathleen]

As we mentioned at the top, Jasmine is an athlete. She played professional basketball in Spain, coached stateside, and stepped into pickup games in the gym later.

[Jasmine Maieta]

It really was my identity as a basketball player that led everything that was me, including my wardrobe, my friend set, etc.

[Kathleen]

And basketball defined her career path. When she was ready for a corporate job, she wanted to stay close to sports. She joined Reebok when she was 26.

[Jasmine Maieta]

I knew I was a fish out of water, but for some reason felt like I just had to be corporate. So I tried to be corporate, but within a couple of weeks I had shifted back to hey, I'm going to work out in the morning and make friends that way. And it worked. I was truly bonding with the senior leaders at Reebok playing pickup basketball.

[Kathleen]

That realization changed her trajectory. Later, she moved to Under Armour. And there was no hesitation.

[Jasmine Maieta]

I was like day two in the gym at 6am recognizing that that is my identity and that's my ability to connect with people.

[Kathleen]

Jasmine was on brand marketing teams throughout her career. During her time at Under Armour, she saw a change in how younger generations look sportswear. No longer satisfied by mere functionality, they.

[Jasmine Maieta]

Wanted more Under Armour was at the time a head to ankle brand. They were trying to break into footwear and we were disproportionately talking to people around the relationship they had with their feet and how sneakers speak. And when sneakers speak, it is a reflection of one's identity. They wanted to know, increasingly not about the technology that Under Armour had become famous for, helping you stay light, dry and fast through an apparel lens. They wanted to know what's the story, what's the colorway, who else is wearing this? Where will it be sold? Those are indicators of image. And image through fashion is identity, and identity is brand.

[Kathleen]

And if you think of a brand that exemplifies this, you might think of Peloton, where Jasmine was global VP of brand. Peloton sells bikes and treads. But the bike wasn't the brand. The people who bought the bike or downloaded the app, the teachers, they loved, they were the brand. And through that brand, a community formed. Jasmine saw that firsthand.

[Jasmine Maieta]

I recognize the power of community. I recognize that, yes, everybody has their own experience, but they do still want to come together. And I had never left that idea and that insight around the people or the brand and really wanting to create a platform that respects diversity.

[Kathleen]

It was at this point that something was coalescing in Jasmine's mind. An idea that would combine all the threads from her professional life, her individuality and love of sports, sportswear as fashion, and the power of community. The thing had a name, round 21, and had a clear brand. It just had to come together. And crucially, this would not just happen through sports, but through art.

[Jasmine Maieta]

I had always been a fan of art, whether it's small galleries and boutiques or even the idea of fashion being representing ideas. And art was going to be a part of round 21 because art has always captured history as it's happening.

[Kathleen]

Between 2018 and 2020, round 21 grew on paper, but she didn't make her move.

[Jasmine Maieta]

I think I waited a while because I didn't have to start it. Then it was me benefiting from the idea, being a side hustle in my 40s where I could earn a living and still feel like, okay, I don't have to take on all that risk. But when Covid hit, risk went out the window because the world and our life was at risk.

[Kathleen]

This YOLO urgency and the privacy Covid demanded allowed Jasmine the safest creative conditions to test her vision. For round 21, there was no way to go lower.

[Jasmine Maieta]

It was only upside to try, because if it failed, everybody was working from Home anyway. It would be like, hey, I took time for Covid and I would go back to, I guess, real life.

[Kathleen]

The conditions were set. But Jasmine had no cash.

[Jasmine Maieta]

A startup without any money, without any, I'd say momentum would need to start and capitalize within an authentic place within sports.

[Kathleen]

And she'd spent her career cultivating that authenticity.

[Jasmine Maieta]

Because I had spent so much time in locker rooms, I knew very few people do that. There's a ping pong table in almost every locker room. It's like the world of sports, other favorite sport, and it's completely unbranded. And I thought, what if we transition this place where the players are coming together to the ping pong table, but reimagine it as a canvas for art? And that would be where round 21 would start without any competition. To be honest, if you'll Remember, sports.

[Kathleen]

In 2020, the NBA had a bubble season where all the teams were living in a bubble in Florida. It was the chance she'd been looking for to start round 21. But Jasmine had no idea who to contact. She cold dmed everyone she could find. And finally, Scott O', Neal, former CEO of the 76ers, connected her directly to the NBA.

[Jasmine Maieta]

The order was 72 paddles. I made them by hand. We used hinoki wood from Japan. Like, we went all in on R and D. I felt like I'm betting on myself. Am I doing this or not?

[Kathleen]

So why not bet big? And you may be thinking, why put so much work into ping pong paddles that are going into a locker room when no one will see them?

[Jasmine Maieta]

When I launched round 21, I knew I wanted to try and create a category of one. And I think with ping pong, nothing felt off the table, because how do you create a category of go somewhere people haven't gone?

[Kathleen]

While all of this was going down, something else was happening online. A series of audio apps were leading live streams in digital rooms every day. One of those apps was Clubhouse.

[Jasmine Maieta]

I was listening to Clubhouse, and basically the whole world of art was tuning in and commenting on the power of digital art and tokens and NFTs. I recognized that the art world was paying attention to this decentralized value and ownership. And then NBA and this company called Top Shot Dapper Labs was disproportionately investing in. What are these now? Digital collectibles.

[Kathleen]

If you remember Pokemon cards, these were kind of like that. But online NBA fans or sports collectors buy a pack or a moment from a player in the form of a video clip, and then they'd own that clip.

[Jasmine Maieta]

And I was very sure that no one would compare us to Nike or Wilson or Spalding if we were a digital first company. So I was like, why don't we try this? So the thesis was, how does the art become a digital membership, if you will, for a collector to use to access the physical version?

[Kathleen]

For example, if Jasmine sold a digital limited edition basketball designed by an artist, purchase of that digital asset would give access to get that basketball in real life.

[Jasmine Maieta]

And feeling like you're a part of something is sports. You know, membership to being a Knicks fan is loving the Knicks. Maybe you go to a game, maybe you buy a T shirt, but there is a sense of membership and people still want physical things. So the digital to physical felt like it would be a scalable model.

[Kathleen]

So Jasmine set out to find digital artists to work with.

[Jasmine Maieta]

We were essentially on a listening tour trying to develop what that could mean for our business in 2020. At the holiday time, we did launch a Kickstarter that was supposed to help fund holiday gifts around ping pong paddles for families to come together. So we were still playing that physical card, but we certainly were thinking about how technology would be a key part of what we built.

[Kathleen]

This eye on tech during the building phase led her to another round of cold emails, but this time with the Bored Ape Yacht Club. If you remember the Ape NFTs that were all the rage in 2020, she had an idea to take her hypothetical digital basketball into a real world. Digital and physical basketball. It's not as confusing as it sounds, I promise.

[Jasmine Maieta]

I emailed the founders and I was like, yo, do you want to do this? Seven days later we launched. It was amazing. They got access to buy the board eight basketball and having the token gave you access to buy it. And in seven days, a quarter of a million dollars worth of physical goods sold to an NFT community. But it was physical goods. I'm like, let's just do this 50 times a year.

[Ben Walter]

Kathleen, how was your first interview? Scary? Fun? Intimidating? None of the above.

[Kathleen]

Jasmine was just so dynamic. I saw so much of myself in her story because she was a corporate soldier. She had had really senior at huge companies.

[Ben Walter]

Was she super tall?

[Kathleen]

She read super tall and she did the whole interview standing. So she was a looming presence. Yeah, I felt like I needed a standing.

[Ben Walter]

I was just listening, going, I bet she's really tall. Yeah.

[Kathleen]

You know, and she represents what a lot of people do, where you do all the right things and then you're looking to make the leap. Start your own Business.

[Ben Walter]

My first reaction was, this woman is brave. She's not afraid to try stuff. She's not afraid to bet on herself.

[Kathleen]

One of the things I wanted to talk to you about is, which I think is a unique dynamic when you've worked in the corporate world or you've worked with big brands. So you're not as intimidated. That she did particularly well is she went out and started pitching big brands to partner with. She did like out of the gate. And I have a tool that I like to use. They're called outrageous asks, which I want to come back to. But essentially the idea is you think of something that you could ask someone to partner with you that makes you seem certifiably crazy because they're like, you are so punching above your weight right now. But she did a few of those with sending cold emails.

[Ben Walter]

And the woman has moxie. Yeah, chutzpah, whatever you wanna call it.

[Kathleen]

And got these responses. And then there were kind of these exponential outsize returns with this. I did one of these with Warren Buffett. I had seen his documentary Becoming Warren Buffett on the plane and I was like, I need to see this guy. And so my outrageous ask to him was, can I fly from New York City to Omaha, Nebraska for five minutes of your time? But the kicker was I found out that he went to McDonald's drive thru every single morning for six decades. So I said, I'll get in at the beginning of the drive thru and out at the end of the drive thru. So there's no added time to your day. I got a not now. But it wasn't a no, it wasn't a never. And I say that to say some of the things that helped propel my small business forward. Early days were reaching out to really big brands or very well known people to mentor, et cetera, who ultimately said yes.

[Ben Walter]

I'll tell you what it reminds me of. It's a good know thyself thing as well. I remember someone who worked in the fundraising business told me there's basically two, two ways you can ask for money. Which asking for money as a not for profit is the same as asking for a piece of business as a for profit business. And he said, you either go with the foot in the door technique or the door in the face technique. And I said, say more? Yeah, say more. And I said, well, the foot in the door technique is you meet someone and you say, I have this great cause I'm saving, you know, kittens with one leg. Would you give me five dollars? Sure. I could Give you five dollars? Well, if you'd give me five, could you give me ten? You could save two cats? Sure, I could give you 10. Listen, my final ask. Could we make it a hundred? You ramp it up over time. I got my foot in the door, and then I slowly push the door. And then there's the door in the face technique where you give the same pitch about how you should save these cats with one leg. And then you say, my only ask, could you donate $5,000? $5,000, and someone starts to slam the door in your face and you say, oh, I'm sorry, I'm sorry. How about just a hundred dollars? Okay, I could do a hundred. I ended up at the same a hundred dollars and one is the foot in the door and the other is the door in the face. I can think of examples in my professional life or with my clients where both of those techniques have worked. Where your ask starts small and builds over time, or where your ask is outrageous and then ratchets back. It's a good opportunity to think about what you're asking for and also what your personality is and what you think you can deliver. Because I can think of situations where both of those might be appropriate. If I go back to the conversation you had with Jasmine, I think she really was more foot in the door. She didn't ask for anything unreasonable, but she was brave enough to ask.

[Kathleen]

To ask. Yeah. And I think that's something anyone who's listening can think about. Like, what are you sitting on? That is an ask you want to make, but you think you're not ready. You know, you're not big enough. Like, go make it. Go make that ask.

[Ben Walter]

And also, if you're shy, get over it. Right? Because she said she DMed everyone she could think of on LinkedIn and just like sprayed and prayed and she eventually got through to some guy from one of the NBA teams. And she just was relentless.

[Kathleen]

That's right. Okay. She's got her foot in the door and now she's going even bigger. She had a date with some sharks. So Shark Tank. Okay, so we're in the tank. I know what a rigorous process it is to get in there. Know those guys?

[Jasmine Maieta]

Well, there was a sense from the Sharks that there's something here. I was definitely validated that self expression and creativity and fashion through sports had never been articulated this way. And the business was balanced. Very, very lucky. We had essentially come into 2020 with physical goods. And then I had been listening and learning the digital side. So I knew that we're Not a digital company. How did the digital and the physical work together? And by the time the taping was happening, we had just had a major win.

[Kathleen]

The bored ape drop we talked about earlier.

[Jasmine Maieta]

My narrative was true and so I guess the that diversification within our business has paid off. Even though sometimes we were working essentially on two different companies at the same time.

[Kathleen]

During the rest of the year they continued operating these two companies, one physical, one digital. We've got the NFT explosion happening in the background. You're riding that wave. You're seeing tremendous results. You've just come off Shark Tank pitching that this is at least part of the business and an investable proposition. When are you saying, oh no, white knuckle, we have gone too far?

[Jasmine Maieta]

Definitely by the end of 2022, the beginning of 23, we were playing digital to physical. And the entire, I'd say ecosystem or industry around NFTs was really leaning into membership. And I was witnessing how many of those communities that had leaned all the way into that were struggling to manage the voices in a way that felt constructive. And we launched our membership holiday 2021. And by being a member you received a mini hoop. But we didn't make anybody pay to be a member, thank goodness.

[Kathleen]

What are you seeing with your community? Are they turning away from it too? And are you seeing the trend shift in that way?

[Jasmine Maieta]

Not really, because NFT owners and Web3 kind of people are very committed to that lifestyle and considering a decentralized world as like the future.

[Kathleen]

But the present for round 21 was all about the physical goods.

[Jasmine Maieta]

All of our physical goods were working. We had the WNBA Players association deal with Brittney Griner working. We had a US Women's National Team World cup program working with Dick's Sporting Goods. There were all of these indicators that the physical world and the business was there and that the nft, the membership, we didn't need to serve to build the business and stay true to the mission of standing for diversity and bringing more voices through sports.

[Kathleen]

But Jasmine had spent most of 2022 investing in NFTs and this Web3 strategy.

[Jasmine Maieta]

And we in 22 had over invested in it. Meaning I had a Web3 agency helping us build tech. I had a person completely focused on loyalty and membership. And I get into 2023 and I am completely personally questioning all of this at this time.

[Kathleen]

We've got a gut that's screaming no, we've got an agency burn rate that's significant. What do you do?

[Jasmine Maieta]

I got advice from a family member of mine who just is extremely savvy on business. Like, just understands business. It is not personal. He is not a personal decision maker when it comes to business. And he was like, if it's not working, kill it.

[Kathleen]

Jasmine's a great strategist and knew there was truth to what her cousin was saying, but it was still really hard to walk away.

[Jasmine Maieta]

And I was really, really clear. And I knew all the money and I knew all of the brand reputation in Web3 and NFTs was valuable, but it just meant, like, psychologically I could not see the data or the trend that this is where the future was really going. And I was convincing myself that it was.

[Kathleen]

After a lot of back and forth, Jasmine quietly sunsetted the digital piece of round 21. And how much would you say you spent in aggregate on the web three metaverse strategy?

[Jasmine Maieta]

Probably 350 to half a million dollars.

[Ben Walter]

Whoa.

[Kathleen]

Does that still hurt?

[Jasmine Maieta]

No.

[Ben Walter]

Okay.

[Jasmine Maieta]

My parents have really taught me, like, what are you going to do with the information you have? Or look back to learn? What did you learn and apply? I think there's something about the culture of round 21 as well, that we're builders. We don't necessarily focus on what' behind us. I still don't regret. I would probably do the exact same thing because of all of the lessons it taught us and that diversification, who knows if that is the future? And so we still have that tech stack. If it comes back, I'd love you.

[Kathleen]

To talk about that. Because I think a lot of people within our listening base are just sitting on things that they don't know whether they should whack a mole it or keep it going. And the deliberation is overwhelming.

[Jasmine Maieta]

I think the distinction is, is it an asset or is it a liability? And as a founder, if you create anything I think you think of as an asset, there is a shelf life to that. My cousin definitely cuts bait. There is no emotional connection he has to anything in his business. He's like, we tried that. It didn't work. We moved on. And to me, it feels like, what if it was just the wrong time or what? He's like, the time you're taking to try and resuscitate and give CPR to something. All of this is market research and you know, when you hit it. And I think that's what I had not felt for a long time, because that one time was the one time with the drop in 21. And so once I started to have some of these hits, I mean, the WNBA changed the trajectory of the business. We got The WNBA license in Caitlin Clark's first year and Camilla Cardozo and Angel Reese. And we were ready. We had apparel infrastructure, we had great brand partners. I spent 20 years in the space. We had retailers and distribution partners ready to work with us. And we've been at the forefront that really changed the trajectory of the brand. I was like, oh, this is what product market fit feels like, you know. And 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.

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[Ben Walter]

With the scale of adjustment and adaptation and pivot that she had to do because she jumped on that NFT bandwagon. I'm going to be really honest with people. I didn't get NFTs when they came out. I still don't get it. I don't know what people are talking about. I understand crypto, I understand stablecoins, I understand blockchain, but I didn't get it.

[Kathleen]

If it doesn't make sense to you, it doesn't make sense. But yeah, she was like out of the gate. Had listened to a few conversations on Clubhouse and then she just decided to go hit this area hard and had such crazy meteoric success with selling the nft. Within a few days she was making six figures. So all of a sudden you're thinking, wow, there's a there there.

[Ben Walter]

I mean it was the NFT moment. I remember it didn't last long.

[Kathleen]

Yeah, she threaded that needle for sure. And then the crash.

[Ben Walter]

So the concept that I wanted to pull out of that story, though, it's something that anybody who has an MBA has learned. And that's the idea of sunk cost, I think most of our listeners know. But sunk cost is when you've spent something, you've already spent it, and then it doesn't go your way, but it's already gone. You can't get it back. And I remember you asked her, does that still bother you that you spent all that money? And she said, no, she had moved on. She learned from it.

[Kathleen]

Still bothers me.

[Jasmine Maieta]

She lost all that money.

[Ben Walter]

And her view was, I can't unspend it. Yeah, I've spent it. So as long as I learn from it, I'm going to make the best decision I can. And the idea behind sunk cost is you can only make decisions going forward. You can't make decisions going backwards.

[Kathleen]

Yeah. And I'm so glad you brought that up, because so many folks just keep spending good money after bad after bad after bad because there's that emotional attachment. Right. And she was good. She just pulled the plug on it.

[Ben Walter]

And she talked about her cousin who advised her, who never made an emotional decision about business in his life, which I think is an extreme point of view. Yeah, sometimes it is emotional.

[Kathleen]

I think we all need a cousin or we need someone in our life like this. I think right now there's been this, like, sprawl where you're doing a lot and you really don't know what the core line of business is that is, like, profitable and driving for you. And so I think there's now this retraction where people are trying to take a more sober look at everything it is they're doing and saying, am I just emotionally attached to this or do I really actually need to shut this down? This is more of a passion point, or this is a facet of my business where I'm break even but not making money. Like, you need to do an honest appraisal of that every now and then.

[Ben Walter]

Yeah. And I think there's such a stigma in American culture in general, but in entrepreneurial circles in particular, around giving up. And there's a difference between throwing in the towel and giving up. Giving up and saying, I'm doing four things and these two are working really well and these other two aren't working, and I'm going to give up on the two that aren't working. And Double down on the two that are. That's not giving up. You have to have some grit and some tenacity to be an entrepreneur. But that doesn't mean that you don't ever recognize when something's not worth further investment.

[Kathleen]

And that failed. That experiment or pilot failed. You didn't fail.

[Ben Walter]

Right?

[Kathleen]

You didn't fail. Like, that's the distinction. Let's get back to Jasmine, who is in the next era of her company.

[Jasmine Maieta]

So era one was web three, era two has been women's sports. And now we're on to era three, harnessing the creative side of sports. So September 2021 was a big month for round 21. It was when we were filming Shark Tank and I had just closed my first and only so far round of funding and that gave me capital to make our first hires. So that was important. Sure, you can curate artists and teams, leagues and athletes, but one person can't do it all. And when we've taken that funding in 21, I've actually completely reinvested it in, into people and process. As we've grown, I've not taken more funding and we're still growing. I'm really proud of that. There's 11 of us now, you know, curating freelancers and contractors, but who are all dedicated to round 21. We have publicly on the team said women's sports is our number one priority. At the top of that list is the wnba. So everything we do first starts with how is this serving our WNBA fan and community community, or how is this building on the foundation of our WMBA business? And we just continued to focus where the community was telling us they wanted to be, which has not ever failed us. From there, I think we have to build process. I am increasingly and intentionally focused on if Jasmine was taken out of this meeting or this process, could it continue? And we're putting resources towards that, whether it is something, you know, hunters and farmers within the sales pipeline. Because what Round 21 has become is a sports fashion house articulating the art on forms and formats that people want to wear. And we have a very high bar of how our community wants to see themselves through products. And that supply chain needs to be robust and it needs to work at the speed of culture. So those are the two places that we are investing along with the team.

[Kathleen]

So you're innovating in terms of fandoms and engaging with sports fans and working with pro teams. How are you thinking about innovation and how do you stay ahead of trends?

[Jasmine Maieta]

We stay with the times or with trends. Or ahead of trends, or create trends through the art community. Define artists however you want to, but there is something about somebody defining themselves as an artist that is a position of power around. I create my own world. And artists in our community typically have a lived experience and their own community that is highly creative and experimental. And we love that. When artists are experimenting, they're experimenting in all forms and formats. Nail art, tattoo art style clothes, cut and sew, diy. They are creating things. And I think we do have a good curation. We certainly see something in the wild with one of our artist partners. Just happened with ties. Heather Salvadar was making WNBA ties. I hit Heather. I'm like, do you want to do this for real, girl? You're bootlegging over here. And we worked with the wnba and now Heather is going to be able to do her thing, and we're going to be the license partner. So that's really what keeps us, I think, fresh. It also keeps us in a place where a fan can come and just kind of peek in and see what's new and next. And maybe at that point, nothing's for them. Or maybe at that point they're like, oh, my gosh, I can't believe what Round 21 just did. But they'll certainly see something that feels new.

[Kathleen]

We talked about individuality within the context of belonging. How do you scale individuality? Because, again, it's one of those things that you think is antithetical to scaling.

[Jasmine Maieta]

So we think of ourselves in the way that you're asking, a little bit like an art gallery. So if you think of an art gallery, let's just choose the louvre or the MoMA, some of the most respected. There is a spirit of curation and the responsibility that the gallery has. So that's what we feel with the curation of the artists and the teams, leagues and athletes that we work with. We try to find a way to balance this gallery of offerings for people. That is the personal piece that there's this spirit of exploration and discovery and choice that you have. But from the perspective of art and sport and creative expression, we want the artist to have a bit of a story designed for you, and you get to choose if that's right for you. That's really the approach that we're taking.

[Kathleen]

So we always wrap by asking for your best piece of advice for fellow entrepreneurs, aspiring entrepreneurs. What would it be for you?

[Jasmine Maieta]

The advice I would give is that you understand your, like, immovable core. What are the characteristics that taking the product out you would never change. But potentially productizing that in a few ways before you strike that product market fit and that allows you to stay diversified in case one of them doesn't work. But it teaches you so much where that fifth way actually might be the way. So I would definitely consider defining your core but how you bring it to market being as open as your imagination because you just never know what might hit.

[Kathleen]

Thank you so much for coming on and sharing your wisdom and hopefully inspiring a whole new wave of women and men and everyone to get into sport.

[Jasmine Maieta]

Thank you so much for the opportunity. It was a blast.

[Ben Walter]

Thanks so much for listening to this episode of the Unshakables. If you liked this episode please rate and review it. We'll be back with new episodes soon so keep an on eye eye on the feed. I'm Ben Walter and this is the Unshakables from Chase for Business and Ruby Studio from iHeartMedia. We'll see you back here soon.