Brook Wineland: AI Needs EI – The Heartbeat of Machine Learning


In the bustling realm of artificial intelligence (AI), where algorithms reign supreme and data is king, there exists a unique advocate for the infusion of humanity into the cold, binary world of machines. Brook Wineland, a seasoned professional with over a decade of experience in the field and a CEO of three companies, is not your typical tech luminary. Rather than focusing solely on the technical intricacies of machine learning, Wineland is on a mission to restore empathy, kindness, and a sense of humanity to the heart of AI.

In a candid and compelling interview, Wineland shared her passion for the cause, shedding light on the challenges she has faced while championing the integration of Emotional Intelligence (EI) into the world of machine learning. The conversation begins with a seemingly lighthearted note as Wineland talks about her tradition of “T-shirt Day” at the office, a unique initiative born out of her desire to inject a sense of fun and camaraderie into the often serious world of technology.

“It’s a shirt, maybe for a line of 2. It’s a shirt,” Wineland chuckles, setting the tone for a conversation that seamlessly weaves between the personal and the professional. As she proudly displays her collection of T-shirts, each with a story of its own, it becomes evident that Wineland is not just a tech executive but a visionary seeking to create a workplace culture that transcends the confines of code and algorithms.

The conversation takes a thought-provoking turn as Wineland delves into the heart of her mission – the integration of empathy into AI algorithms. Holding up a T-shirt with the words “Love Your Nearest Neighbor,” Wineland introduces us to an AI algorithm that groups data into neighborhoods based on similarity. The irony, she points out, lies in the fact that the algorithm, while creating these neighborhoods, remains indifferent to the concept of love. It’s a poignant example of the very issue Wineland is determined to address – the lack of emotional understanding in the world of AI.

“This issue cuts deep for me,” Wineland admits, her tone becoming more serious. Recalling instances where her attempts to collect data on happiness and empathy were dismissed as jokes in the tech industry, she highlights the prevailing perception that emotions have no place in the business of AI. “I don’t know what it is about the IT industry, but it comes across as a joke. And it’s defeating and humiliating for me because I’m serious when I say it. It’s not a joke,” she emphasizes.

Wineland’s passion intensifies as she draws attention to the critical issue of mental health, a topic often overlooked in the pursuit of technological advancement. “Things like mental health are not a joke,” she asserts, underlining the gravity of incorporating basic humanity into the coding of AI. The dismissive attitude she encounters – being labeled as “cute” for caring about feelings in a business context – serves as a stark reminder of the uphill battle she faces in her mission.

Her frustration with the prevalent mindset within the industry becomes palpable as she challenges the notion that metrics related to happiness are somehow less “real” than other performance indicators. “What do you mean? This isn’t real. This is important,” Wineland passionately retorts, emphasizing the significance of considering emotional well-being in the development of AI.

As the conversation delves deeper, Wineland articulates a profound concern – the prospect of building AI that disregards human emotions and values. The scenario she paints is chilling: AI measuring only the quantitative metrics, oblivious to the impact it has on the lives of those who interact with it. “I can’t build more AI without taking these things in. I can’t go to any more of my friends’ funerals and then show up for work to build another AI that just measures the click-throughs on our email marketing campaign because happiness is for girls,” Wineland asserts, highlighting the ethical dilemma that lies at the intersection of technology and humanity.

However, Wineland’s passion is not just fueled by a desire to rectify the negatives. She firmly believes in the transformative power of incorporating emotional intelligence into AI. Drawing on her experience, she presents a compelling case – one that goes beyond theory and ventures into tangible, real-world impact.

“When we incorporate things like happiness, humanity, kindness, empathy, leadership, and teamwork into the AI, we have the potential to make people’s lives better and drive revenue,” Wineland enthuses. Her optimism finds expression in a simple yet powerful example – the impact of a T-shirt on employee engagement and retention. The statistics may back it up, but Wineland’s conviction lies in the intangible: the sense of value, acknowledgment, and belonging that a simple act like gifting a T-shirt can create.

“You buy a recruit or a new hire a T-shirt. Send it to them in the mail. They open it. That person is 70% more engaged, and more productive, and they will stay twice as long. So retention doubles,” Wineland explains, underscoring the direct correlation between emotional well-being and professional success. It’s a testament to the fact that the integration of humanity into AI is not just an altruistic pursuit but a strategic one that can yield tangible benefits for businesses.

In conclusion, Brook Wineland emerges not just as a tech executive but as a visionary with a mission – a mission to infuse the heartbeat of humanity into the algorithms that increasingly shape our world. In her unwavering pursuit of emotional intelligence in AI, Wineland challenges the status quo, confronts dismissive attitudes, and presents a compelling case for a future where technology enhances, rather than diminishes, our shared humanity. As she aptly puts it, “Everyone loves a good T-shirt,” but perhaps, what we need even more is a tech industry that loves and prioritizes the well-being of the humans it serves.