Emma Grede says she was ‘using AI like a 42-year-old woman’ until Mark Cuban gave her a wake-up call

In a rapidly evolving technological landscape, even the most successful entrepreneurs can find themselves feeling behind the curve. Emma Grede, the powerhouse co-founder of Skims and CEO of Good American, recently shared a candid revelation about her journey with artificial intelligence. Despite managing multi-billion dollar empires, Grede admitted that her initial approach to AI was superficial and lacked the strategic depth required for the modern business era. It took a blunt, high-stakes conversation with fellow billionaire and tech enthusiast Mark Cuban to provide the necessary "kick" that transformed her perspective. Grede’s story is a powerful testament to the necessity of lifelong learning and the humility required to pivot when faced with industry-shifting innovations.

Emma Grede realized she was using AI in a basic, non-strategic way—which she described as "using AI like a 42-year-old woman"—after discovering Mark Cuban utilizes over 60 different AI applications to streamline his ventures. This wake-up call led Grede to enroll in AI courses at Wharton and Harvard, and she now implements "AI Days" every six weeks to ensure her brands, including the $5 billion Skims, remain at the forefront of technological integration. By incentivizing her staff with bonuses for AI adoption, Grede has shifted her leadership style from cautious observation to aggressive implementation, labeling the transition as a "do or die" moment for modern founders.

The Blunt Conversation with Mark Cuban

The catalyst for Emma Grede’s technological overhaul was not a dry industry report or a board meeting, but a direct conversation with Mark Cuban. Cuban, known for his early adoption of disruptive technologies from broadcast.com to the current generative AI wave, challenged Grede’s existing methods. During their interaction, it became clear that while Grede was aware of AI, she wasn't living and breathing it the way a tech-forward founder must. Cuban revealed that he currently manages approximately 60 different AI-driven apps on his phone, using them for everything from financial analysis to creative brainstorming. This level of immersion was a far cry from the casual prompts Grede had been experimenting with.

For Grede, the realization was immediate and humbling. She recognized that her current level of engagement was the equivalent of using "dial-up" in a high-speed fiber-optic world. Cuban’s advice was simple but urgent: treat AI not as a peripheral tool, but as a core component of every business function. This interaction served as a "wake-up call" that prompted Grede to reassess not just her personal habits, but the entire operational structure of her companies, including Skims, Good American, and Safely.

What it Means to Use AI Like a 42-Year-Old Woman

The phrase "using AI like a 42-year-old woman" became Grede’s shorthand for a specific type of tech complacency. In her view, it represented using tools like ChatGPT merely for drafting basic emails or asking simple questions—utilizing perhaps 1% of the technology's actual capability. It signifies a generational and professional gap where leaders use new tech through the lens of old habits. Grede recognized that this "safe" approach was actually a liability in an environment where younger, more agile competitors were using AI to automate supply chains, personalize marketing at scale, and predict consumer trends with uncanny accuracy.

By labeling her own behavior this way, Grede highlighted a common trap for successful Gen X and Millennial executives: the belief that their previous success and foundational business knowledge are enough to carry them through the AI revolution. She realized that being a "user" of technology is not the same as being a "master" of it. This self-critique prompted her to step out of her comfort zone and seek formal education to bridge the gap between being a fashion mogul and a tech-literate leader.

The AI Day Strategy: How Grede Stays Ahead

To combat the risk of falling behind again, Emma Grede implemented a rigorous new routine: the "AI Day." Every six weeks, Grede clears her entire schedule to focus exclusively on artificial intelligence. During these dedicated sessions, she explores new software, tests emerging large language models, and analyzes how these tools can be integrated into the specific workflows of her various brands. This isn't just about reading articles; it's a hands-on laboratory approach where she experiments with prompts, data visualization, and automated research tools.

This disciplined approach ensures that her knowledge doesn't become stagnant. In the world of AI, six weeks can represent a lifetime of development. By institutionalizing this learning period, Grede is signaling to her entire organization that technological fluency is a top priority. These AI Days allow her to move beyond the "42-year-old woman" phase and into a space where she can lead her technical teams with a clear understanding of what is possible, rather than just what is popular.

Upskilling at Ivy League Institutions: Harvard and Wharton

Emma Grede didn't stop at self-study. Recognizing that the complexities of machine learning and data ethics required a structured foundation, she enrolled in executive education programs at some of the world’s most prestigious institutions. By attending courses at Harvard and Wharton, she sought to understand the "why" behind the "how" of artificial intelligence. This academic immersion provided her with a framework to evaluate AI vendors and internal projects with the same scrutiny she applies to garment quality or marketing spend.

The move to go back to school while running multiple companies demonstrates a level of humility rarely seen in high-level CEOs. It reinforces the idea that the AI revolution is significant enough to require even the most "self-made" billionaires to become students again. Her time at Harvard and Wharton allowed her to network with tech leaders and academics, further refining her strategy for integrating AI into the $5 billion Skims empire and ensuring the brand’s longevity in a digital-first economy.

Incentivizing Innovation: Cash Bonuses for AI Integration

Transformation cannot happen at the top alone. Emma Grede has taken aggressive steps to ensure her entire workforce is aligned with her new tech-forward vision. One of her most notable strategies is the introduction of cash bonuses for employees who successfully integrate AI into their specific roles. Whether it's a designer using AI to iterate on patterns more quickly or a customer service representative using AI to improve response times and sentiment analysis, Grede is putting her money where her mouth is.

This incentive structure serves two purposes. First, it alleviates the common fear that AI is coming to "replace" jobs by framing it as a tool that "enhances" performance and rewards initiative. Second, it turns her hundreds of employees into a massive research and development team. By encouraging experimentation across all departments, Grede ensures that the most practical and efficient AI use cases bubble up to the surface, allowing the company to scale its successes rapidly. This cultural shift ensures that "AI Literacy" becomes a core competency for everyone in her organization.

The Business Case for AI in Fashion and Retail

For a brand like Skims, which has grown into a broad lifestyle and beauty name valued at $5 billion, the applications for AI are limitless. Grede is looking at AI through several key lenses that directly impact the bottom line:

• Supply Chain Optimization: Predicting demand to reduce overstock and minimize the environmental impact of unsold inventory.
• Personalized Marketing: Using data to deliver individual-level recommendations that increase conversion rates and brand loyalty.
• Creative Iteration: Utilizing AI image generators to explore color palettes and silhouettes before a single physical sample is produced.
• Customer Experience: Implementing sophisticated AI agents that can handle complex inquiries with the same nuance as a human representative.

By applying the lessons learned from her "wake-up call," Grede is transforming Skims from a celebrity-backed brand into a tech-enabled powerhouse. This focus on efficiency and data-driven decision-making is a major reason why the company is on track to top $1 billion in sales this year. In the competitive world of retail, the ability to pivot quickly based on AI-generated insights is the ultimate competitive advantage.

Business Area	AI Implementation Strategy
Product Design	Using generative AI for rapid prototyping and trend forecasting.
Marketing	Hyper-personalized ad targeting and AI-driven content creation.
Operations	Automated inventory management and predictive logistics.
Talent Management	Skill-based training and bonuses for AI proficiency.

Mark Cuban’s 60 AI Apps: A Benchmark for Entrepreneurs

The specific detail that shocked Grede—Mark Cuban’s use of 60 AI apps—serves as a benchmark for what "immersion" looks like in the current era. Cuban’s philosophy is that if you aren't "playing" with these tools every day, you are essentially forfeiting your future as an entrepreneur. For Cuban, AI isn't a single software package; it's an ecosystem of specialized tools that handle everything from coding and legal review to nutritional tracking and sentiment analysis of social media trends.

This level of engagement allows a founder to see connections and opportunities that others miss. It turns AI into a "mentor" or a "staff of a thousand business professors," as Cuban often describes it. For Grede, following this lead meant moving beyond the "one-app" mindset. It meant building a "tech stack" that works in harmony to provide a 360-degree view of her business and the market at large. This shift from casual user to power user is the defining characteristic of the "wake-up call" she received.

Why AI Literacy is "Do or Die" for Modern Founders

Emma Grede’s sense of urgency stems from a sobering reality: the divide between AI-literate businesses and those that ignore it is becoming an unbridgeable chasm. She has described this moment as "do or die." Research supports her stance, with reports suggesting that AI skills can lead to significant pay boosts for individuals and massive efficiency gains for corporations. Conversely, companies that fail to upskill their leadership and workforce risk obsolescence in a world where AI can automate the mundane and supercharge the creative.

For founders, AI literacy is no longer a "nice-to-have" skill for the IT department; it is a foundational requirement for leadership. Grede’s journey shows that it is never too late to start, but that the start must be serious and sustained. By moving from a state of "using AI like a 42-year-old woman" to being a tech-forward visionary, she has secured her place as a leader who is not just reacting to the future, but actively shaping it. Her story serves as a call to action for every leader to evaluate their own tech habits and ask if they, too, need a Mark Cuban-style wake-up call.

Frequently Asked Questions

Q: What did Emma Grede mean by "using AI like a 42-year-old woman"?
A: She meant she was using the technology in a very basic, non-strategic way, such as only using ChatGPT for simple tasks, rather than integrating AI deeply into her business operations and strategy.

Q: How many AI apps does Mark Cuban have on his phone?
A: According to Emma Grede, Mark Cuban has approximately 60 different AI applications that he uses to stay ahead in business and technology.

Q: What is an "AI Day" in Emma Grede's schedule?
A: It is a dedicated day every six weeks where she clears her calendar to focus entirely on learning about new AI tools, developments, and strategies for her brands.

Q: Where did Emma Grede take courses to learn about AI?
A: She enrolled in executive education programs at Wharton and Harvard to gain a more technical and strategic understanding of artificial intelligence.

Q: How does Emma Grede encourage her staff to use AI?
A: She offers cash bonuses to employees who successfully find ways to incorporate AI into their work to improve efficiency and innovation.

Conclusion

Emma Grede’s evolution from a casual AI user to a dedicated tech-driven leader is a blueprint for modern entrepreneurship. By acknowledging her shortcomings and seeking guidance from mentors like Mark Cuban, she transformed a potential liability into a significant business advantage. Her commitment to education through Harvard and Wharton, combined with practical strategies like "AI Days" and employee incentives, ensures that her $5 billion brand, Skims, is prepared for a future where AI is the primary engine of growth. Grede’s story reminds us that the greatest risk in business isn't the technology itself, but the refusal to adapt to it. As she continues to scale her empire, her "wake-up call" stands as a vital lesson for leaders everywhere: in the age of AI, curiosity and continuous learning are the only paths to survival.

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