Buddy Teaster did not set out to write a book. As the president and CEO of Soles4Souls (S4S), a nonprofit that turns shoes and clothing into opportunities, he’s used to talking about impact, but a request to give a different kind of presentation planted a seed.
“It was an unexpected invitation to make a presentation, but not about the usual S4S work,” Buddy says. “They wanted something broader than just what we had done, but how could others learn from those experiences. The talk went well, and it started to percolate. And then, about 18 months later, we decided to pursue the book.”
That book became From Tailspin to Tailwind: Leadership Lessons for Turning Crisis into Clarity, a deeply personal and practical reflection on leadership, resilience, and the winding path of transforming a struggling nonprofit into a thriving, purpose-driven organization. The title itself carries weight.
“I think those are both phrases that people know, use, and intuitively understand,” he explains. “With just two words, there’s an entire arc to a story. And I liked the alliteration.”
Telling that story required honesty. While transparency is one of the organization’s core values, Buddy admits there were parts that weren’t easy to share. “There are two parts that we did wrestle with. First was what’s going on in Transnistria with our partner there, who is still in jail for absolutely no reason other than being successful at building a business that helps so many people. The second is that the two people the book is dedicated to, David Graben and Robert Adams-Ghee, both passed away in the last few years. They were so central to the S4S tailspin to tailwind story that it was just sad for them not to be here to know where we are now.”
At the heart of the book is a hard-earned truth Buddy learned not in boardrooms, but out on long-distance ultramarathon trails. “It’s not explicit in the book, but it’s a lesson I learned from my years of ultrarunning: ‘It never always gets worse.’ Even at some of our lowest points, financially and emotionally, we could find ways to keep going. That’s almost always true, and I know it’s kept me going many, many times.”
Buddy’s leadership style has been shaped by a commitment to aligning purpose and profit—two forces often seen as being at odds. “Like many folks, for many years, I thought those things were somehow mutually exclusive. My time at S4S has shown me, over and over and in so many different ways, how aligned they can be. Because we’re so clear on our purpose—creating opportunities for people through shoes and clothes—I am totally comfortable with earning a profit that we plow back into our purpose. Each reinforces the other.”
When the inevitable tension arises between mission and business demands, Buddy returns to that central clarity. “Always, always come back to the purpose. It’s often so clarifying that the clash goes away. That could change, right? For example, we could hit a tough economic patch that would create a lot more tension. So, I don’t mean to imply we have it figured out. Only when we have been through hard times—the pandemic, the death of two of our key executive team members—we were able to turn to our purpose and our values. And that’s what helped us navigate.”
His advice to other leaders going through “tailspin” moments? “Don’t do it alone. There are (I hope!) people who love you and want you to pull out of the nosedive. But you must have the courage to ask for help, tell them and yourself the truth and listen. That pause between thought and action is the whole game.”
Despite the serious subject matter, Buddy insists the most rewarding part of the work is how often he sees its impact. “Are you kidding!?!?!? It’s nearly every day. Talking to an entrepreneur who bought her first house and another who sent one of her children to university with the income from selling shoes is just as powerful as seeing one of our team members figure out how he can be vulnerable and successful at the same time.”
That sense of purpose and a dose of humility have kept him grounded. “First, I have three incredible women in my life—my wife, Becca and two daughters in their 20s. I never get away with too much ego! Working with many people in different situations, I am also acutely aware of the sheer randomness and luck of it all. That’s the most humbling thing in the world.”
If he could go back and give his younger self a single piece of advice, it would be this: “Notice all the amazing people and things around you, then be way more grateful for them more often.”
“Even at some of our lowest points, financially and emotionally, we could find ways to keep going.”
“Always, always come back to the purpose. It’s often so clarifying that the clash between profit and mission goes away.”