Toussaint Bailey: Aligning Values with Investment


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Aligning investments with personal values is a passion for Toussaint Bailey, and it's the foundation of Uplifting Capital, the investment platform where he is founder and CEO.

The firm was born out of the introspection that followed his processing of George Floyd's death.

“It caused everyone to reflect on where we were personally and as a country," Toussaint says.

His first action was to call an all-hands meeting where the team conducted their normal routine of one-word check-ins about their feelings. His voice shaking, he managed to share the word “distracted."

As the sole Black professional in his firm, he hadn't expected his colleagues to be equally weighed down by the moment, but it opened up productive conversations about racism and workplace bias.

“These were conversations I'd never let into work before, but I became inspired to promote them more," he says.

That led to bringing in speaking and listening therapists and coaches to help facilitate conversations that allowed both parties to speak and receive messages without judgment.

“People were able to move from sympathy, which becomes a conversational disconnect, to empathy and compassion," he says.

Toussaint took a sabbatical to further these conversations through podcasts, which ultimately led him to start Uplifting Capital as a reflection of his values.

As a leader, Toussaint believes the only way to drive fulfillment for clients is to drive fulfillment for the people inside the firm. That has led to a four-pronged approach to engagement. The first level is building loving and trusting relationships, which leads to self-actualization and then co-creation and collective impact.

“If they all go in order, then personal rewards come naturally," he says. “However, a lot of people in our profession put the fourth level, personal gain, first and then try to find the relationships that will bring that. We believe our sequence will ultimately bring fulfillment at work but also in life."

In today's episode, Toussaint talks to Ana and Jamie about how to foster more productive conversations, the industry trend he expects will change in the next 10 years, the top book he would recommend right now and the best sandwich to order at Subway, where he was a sandwich artist in high school (and knew all the off-menu tricks).
You can find show notes and other information at

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