The Art of Investing
A professional runner turned investor wunderkind, Cack Wilhelm, ’14, shares lessons she’s learned from competitive racing, venture capital, and business school.
The Art of Investing
Hugh Cole came out as a gay man in 1980 after leaving his hometown of Chicago to attend university. It was a time when few came out—no one else from his community ever had. But in a new setting, and after years of hiding, Cole felt emboldened to freely express himself.
“I started to challenge the mental model I held of nonbelonging and shifted toward celebrating and taking pride in who I was,” says Cole, adjunct assistant professor of leadership. “It called for me to be brave and true to myself in ways that were transformative. That continues in the work that I do at Booth.”
Since 2022, he has taught the course Interpersonal Dynamics. Cole, who also serves as a psychotherapist at the Chicago Pride Center, says that his class is a celebration of diversity. It’s also an opportunity to foster inclusivity and acceptance among the business leaders of tomorrow, no matter who they are and what identities they hold.
Evening MBA student Jason Antwi says the interpersonal skills he developed in the course wildly surpassed his expectations. “I gained a strong sense of belonging among classmates of different backgrounds and lived experiences, a deeper understanding of how my emotions added to—or detracted from—the connections I engaged in, and a renewed understanding of the value of my experiences as a Black man in my personal and professional interactions.”
Cole says his passion for Interpersonal Dynamics has grown out of his personal journey and his commitment to connecting across differences. “What I love about the model of Interpersonal Dynamics at Booth is that we try to make the experience of these differences speakable,” he says, “teaching business leaders how to self-manage their feelings and express themselves more effectively, especially in moments they are feeling disconnection or other negative feelings.”
“I started to challenge the mental model I held of nonbelonging and shifted toward celebrating and taking pride in who I was. It called for me to be brave and true to myself in ways that were transformative. That continues in the work that I do at Booth.”
After Cole came out as gay, he embarked on a decades-long journey of service and found his own sense of belonging in the LGBTQ+ community.
Cole was working as an actor in New York in 1988 when he started volunteering with the AIDS service organization Gay Men’s Health Crisis (now GMHC) during the AIDS epidemic. He was partnered with men who were scared and dying, often abandoned by others.
In these times, long before he became a psychotherapist, Cole saw the transformational power of simply being with someone and listening to understand how that person feels. No bias, no defensiveness, simply shared moments of humanity.
“That impacted the trajectory of my life in profound ways,” Cole says. “It trained me to be brave in vulnerable situations, and it taught me this concept of the beginner’s mind, which I now try to bring to everything I do: Can I show up as though I’ve never met this moment before?”
After years away from home, Cole returned to Chicago to reconnect with his family in the early 2000s. For the first time, he felt comfortable as himself around them—it allowed him to connect with them in a new way.
During this time, Cole took his first social work class at Harold Washington College and was fascinated—he learned concepts that described what he had experienced throughout his life and volunteer work. Realizing he could use his personal journey to help even more people, he pursued a master of social work degree.
In 2007, Cole began working at the LGBTQ+ healthcare and social services provider Howard Brown in Chicago, supporting people with substance abuse problems. He led group therapy sessions and saw how powerful it could be when members openly expressed their feelings to a supportive group. It reinforced his belief that connecting across differences cultivates a sense of belonging in the world.
“I’ve learned that not only do I belong, but to a certain degree, belonging was always a choice that I didn’t see was available to me,” Cole says. “This is so transformative for people who have learned in subtle ways—and not so subtle ways—that they don’t belong.”
“For our students at Booth, it’s such a brave thing to think about the biases they hold and how they can reach past them. . . . It’s my wish that we can all connect through our differences with interest, curiosity, and acceptance.”
At Booth, Cole loves that students, professors, and faculty embrace differences and honor dissenting views.
“This goes back to the idea of being enriched and strengthened by being curious about a different perspective,” Cole says. “We don’t have to be threatened by it.”
Cole wants to drive this point home more deeply in Interpersonal Dynamics, where he teaches students frameworks to foster understanding and connection. Full-Time MBA student Neha Saxena says that now, whenever her relationships get hard, she can draw on those lessons.
“The key lesson I learned is that assuming things about others creates distance between us,” Saxena says. “People’s outward behavior is influenced by their complex past experiences, which we often don’t fully grasp. To foster true connection and belonging, we should understand each other’s intentions, check our assumptions, and engage in open communication.”
Cole believes these lessons translate perfectly to business leadership. If leaders can allow for differences and make their experience more speakable with other people, they can more deeply understand themselves and the world. They can accept others as they are and foster a culture of belonging in their organization that creates a brave space for risks and innovation.
“It’s a rich win–win opportunity all the way around,” Cole says. “But it also calls us to look at the biases that we hold and ask, ‘How are my choices working for me in my leadership? In my organization?’ It calls us to have the humility to invite dissenting opinions and be challenged by them, so you can think in an expansive way.”
Cole hopes that these ideas and his class can be brought to as many people as possible. In a world that often feels divided, he believes that embracing difference is what the world needs.
“For our students at Booth, it’s such a brave thing to think about the biases they hold and how they can reach past them,” Cole says. “Some of the students that I’ve worked with have been transformed in their thinking and feeling, and that will continue after Booth. It’s my wish that we can all connect through our differences with interest, curiosity, and acceptance.”
A professional runner turned investor wunderkind, Cack Wilhelm, ’14, shares lessons she’s learned from competitive racing, venture capital, and business school.
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