Emma Grede’s AI Awakening: How Shark Tank’s Mark Cuban Sparked a Tech Revolution in Her Business Strategy

Emma Grede, the British-born entrepreneur behind Kim Kardashian’s $5 billion shapewear brand Skims and the CEO of Good American denim, has long been a visionary in spotting cultural trends before they explode. Known for redefining inclusion in retail and making history as the first Black female investor on Shark Tank, Grede recently shared how a conversation with fellow Shark Tank star Mark Cuban ignited a new urgency in her AI adoption.

This shift matters because it highlights how even the most successful business leaders recognize the need to evolve with technology. Grede’s candid admission about her AI learning curve and her proactive steps to integrate AI into strategic decision-making offer a blueprint for entrepreneurs navigating the fast-changing digital landscape.

The Mark Cuban Moment That Changed Everything

In an exclusive 2025 interview with Fortune, Grede revealed how a podcast episode with Mark Cuban, where they compared AI usage, was a turning point. Cuban’s staggering use of 60 AI apps on his phone gave her a much-needed push. “He gave me a kick,” Grede said, prompting her to enroll in AI courses at Wharton and Harvard to catch up.

Leading AI Adoption Before Realizing She Was Behind

Grede was no stranger to AI in the workplace. Two years ago, she incentivized her team with cash bonuses for integrating AI into their work, sparking a cultural shift in her office. Marketing and finance teams especially embraced AI, transforming how they presented and executed tasks. Yet, Grede admits she relied too heavily on her younger staff, using AI more like a search engine herself.

• Offered cash bonuses to employees using AI
• Saw immediate improvements in work quality and creativity
• Realized she needed to deepen her own AI skills
• Started formal AI education at top business schools

Why AI Isn’t About More Productivity for Grede

Despite her reputation as one of America’s most productive self-made women, Grede doesn’t see AI as a tool to squeeze more hours out of her day. Instead, she views AI as a way to enhance strategic decision-making. “There’s no amount of AI that can help me with high-stakes decisions,” she explained, but it can provide data-driven insights to optimize those choices.

“So much of my job is about making really big bets and decisions. And so if I can put data in places to optimize that decision making, I think that’s probably where I’m going to be using it most.”—Emma Grede

A Stark Warning from Mark Cuban to Entrepreneurs

During their podcast, Cuban delivered a blunt message to founders hesitant about AI: ignoring it is like refusing to use a PC or the internet decades ago. He urged entrepreneurs to experiment with AI tools, describing it as having “an entire staff of 1,000 business professors” at your fingertips.

“You’re f–ked… If you’re an entrepreneur, or want to be an entrepreneur, start playing with it to get a sense for how it works, how to prompt.”—Mark Cuban

Looking Ahead: How AI Will Shape Grede’s Leadership

Grede’s journey from AI novice to proactive learner underscores a broader trend among CEOs racing to future-proof their businesses. She envisions AI reshaping her role as a merchant and planner, enabling smarter bets and more informed leadership. As AI continues to evolve, Grede’s story serves as a powerful reminder that embracing technology is essential—not optional—for sustained success.