Empathy: The driving force of entrepreneurship

For people facing long odds, an entrepreneurial mind-set matters

About 77 million Americans have a criminal record. Experts expect that number to be 100 million by 2030. For the estimated 600,000 people returning home from incarceration annually, a criminal record creates substantial barriers to obtaining housing, employment, government benefits and continuing education, due to myriad federal and state restrictions. Getting an ID and finding a job — any job — are immediate priorities. No surprise that recidivism rates for returning citizens range from 29% to 59%, depending on the state.

For people facing long odds, an entrepreneurial mind-set matters. That’s why I can’t wait to lead the upcoming fall session of "Project Entrepreneur," a business fundamentals course for entrepreneurs with criminal records at Boston College Law School. Whether our new CEOs launch a full or part-time business, now or in the future, the skills, connections, and confidence they gain while thinking entrepreneurially can be incredibly useful. With a volatile economy, widening income inequality, and the bitter fraying of community in places large and small, entrepreneurialism offers hope. As I dip into another stack of books, I’m thinking a lot about why.

Successful entrepreneurs know and practice empathy. That means seeing an opportunity, the potential customer, and even yourself through fresh eyes. A Second Chance: A Federal Judge Decides Who Deserves It, the recent book by longtime judge Frederic Block, is a compelling example of how this might be done. With the backdrop of the 2018 First Step Act, Block revisits six convictions to see if he got them right. He starts from the empathetic premise that we are all more than the worst thing we’ve ever done. His fascinating and meticulous review of the background, the victims, and the aggravating and mitigating circumstances of each case reflect a keen judicial mind and an unwavering commitment to what both justice and mercy might require. Resilient entrepreneurs know that mistakes happen too. Empathy allows them to experiment, fail, embrace the learning that follows and to encourage others to do the same.

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In fact, the most insightful entrepreneurs lead with empathic mentorship. Venture investor and Tech Stars co-founder Brad Feld captures this spirit in his latest book: Give First: The Power of Mentorship.“Paying it Forward,” Feld explains, feels cliched, obligatory, transactional, and ultimately, insufficient. We’re all better off, he argues, if we think more broadly about giving and benefiting as part of a connected entrepreneurial community. A prolific writer, Feld previously has covered a broad variety of venture, investing, and governance topics in a series of smart, practical, engaging books that I’d highly recommend. This one feels different. In a time of remote work, virtual networking and AI models that supplant and simulate human connection, Feld urges mentors to approach their distinct role with authenticity, humanity and intention, without demanding money or shares upfront.

I’ve seen firsthand the deeply positive effect of authentic mentoring in Project Entrepreneur. Feld’s inspired message is one that few entrepreneurs expect and all of them deserve.

Finally, transforming empathy into disruptive action is the stuff of social entrepreneurship, and if done well, it benefits us all. That means calling out problems and promoting new ideas, even if leaders don’t want to listen.

Georgetown Law professor Brad Snyder's fascinating new book, You Can’t Kill A Man Because of the Books He Reads, offers a timely case in point. Synder details the arrest, conviction and long path to freedom for Angelo Herndon, a Black community organizer and avowed communist arrested in 1930s Atlanta for protesting on behalf of marginalized workers. Herndon was a scrappy and determined activist. Although his entrepreneurial work as publisher was problematic, Herndon certainly knew how to galvanize a community, shape media coverage, and advocate for change. His admirable resilience in vindicating the rights to free speech and peaceable assembly reveal important lessons for today. 

In uncertain times, we all need to lean into community. Embracing empathy-driven entrepreneurship is a great place to start. 

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Larry Gennari is a business lawyer and chief curator of Authors & Innovators, an annual business book and ideas festival. Watch recent interviews with authors here. Gennari also teaches Project Entrepreneur, a business fundamentals bootcamp for returning citizens, at BC Law School.