How to Overcome Entrepreneurial Challenges

Learning from failure and turning setbacks into success are valuable skills for any entrepreneur. To find practical insights into entrepreneurial resilience, I tapped into the experiences of three entrepreneurs in very different industries – Andy Hunter, founder and CEO of Bookshop.org, an online retailer where every purchase financially supports local, independent bookstores; Ayo Balogun, the chef and owner behind Brooklyn restaurants Dept of Culture and Radio Kwara; and Pat Lore, the Guilford, Connecticut-based author, speaker, and owner of video agency Headline Productions. Keep reading to see what you can discover from their generous and hard-earned wisdom.

Navigating Uncertainty Through Strategic Collaboration 

Andy Hunter – also the co-creator of Literary Hub, a website for literary culture – remembers waking up at 3 a.m. in a state of anxiety not long before Bookshop.org launched, calculating how many customers he'd need for the business to break even: roughly 375,000, and he had just six months of cash reserves.

“How on Earth am I going to get that many customers?" he wondered. “I didn't fall back to sleep that night. Instead, I worked out a strategy – to use the power of small communities, partnering with nonprofits, magazines, small bookstores, and authors. This meant thousands of partners, none of them huge. But each would bring their own audience to our platform.”

And that's what Bookshop.org did – by creating its affiliate program, and by partnering with more than 1,000 small bookstores in its first year. “For months, we walked the walk,” Hunter says, describing the process of having to earn trust within the bookseller community. “We listened to bookstores, built our business around their needs, and demonstrated that we were who we said we were: a benefit corporation [B-corp] with a mission to help them. I learned that trust had to be earned, and we earned it over time … we've [now] put over $31 million in the pockets of booksellers in the U.S.” 

Recalling that sleepless night, Hunter takes pride in exceeding his then-goal of 375,000 customers. Bookshop.org ended that year with over a million. 

Looking further back to when he was trying to raise seed investment for Bookshop.org, Hunter says, “I remember a day when I was traversing New York City, pitching potential investors, all of whom were skeptical. I didn't have a co-founder; Bookshop.org was just a slide presentation; it was just me and my idea, which no one believed in but me. When I was traveling home that day, I felt an acute sense of loneliness and near-hopelessness. But I learned a long time ago how important it is to behave as if there's hope even if you don't feel it at the time. I kept going.”

Adapting Your Strategy Through Mitigating Risk

According to Ayo Balogun, he has an estranged real estate investor-developer to thank for the success of his most acclaimed restaurant. “We’ve been quite lucky, in a way. If he didn’t illegally evict us [from one of my previous restaurants], I wouldn’t have opened Dept of Culture. At the time, getting displaced seemed like the end of the world. But at the end of the day, you dig into what you do – for me, that’s working with food – and you find another expression. You find a slightly different way to mitigate risk. Rather than starting another high-cost restaurant immediately after that lawsuit, I came back by expressing myself differently, through a pop-up.” 

Born out of that pop-up dinner series, Dept of Culture was nominated for the James Beard Foundation’s prestigious “Best New Restaurant” award in 2023. At Dept of Culture, he cooks nightly for 16 people seated at a communal table in Bed-Stuy, Brooklyn, while sharing family stories behind the tasting menu, inspired by north-central Nigerian cooking. 

And then there was that time a car crashed into one of his Brooklyn restaurants. “Again, that's a thing you don't plan for,” Balogun says. “It was very distressing. We had to shut the place down for a while. The initial response to something like that is panic – whether you show it, you’re panicking inside. But if you have insurance in place, and you have backup funds in addition to that, you can deal with it and move forward.”

Building Resilience Through Vulnerability 

Pat Lore's departure from the TV business underscores the power of vulnerability in building authentic connections and credibility. Headline Productions, her video production agency, was born after she “suffered from a serious bout of impostor syndrome as a television reporter,” she says. 

"I learned a long time ago how important it is to behave as if there's hope even if you don't feel it at the time. I kept going.” — Andy Hunter, founder and CEO, Bookshop.org 

This pivot away from her longtime industry was accompanied by deep shame around her sudden fear of public speaking. “But when I started talking about my fear, it bolstered my credibility and deepened my relationships with clients,” she says. “As a producer behind the scenes, I was able to coach my interviewees through their nerves and share how I had been in their shoes.”   

As a result of this evolution, in 2019 Lore created the online course, “Be Authentic on Video." Through this program, she helped entrepreneurs learn to be natural on camera. The course – which created a passive income stream for Lore right before the global pandemic, when one hundred percent of her in-person video production work disappeared – also led to the publication of her first book in 2021. In addition to generating revenue, the book and course also led Lore to offer another new ongoing service: video coaching.

All these business leaders used the core strategies and skills needed to overcome challenges in entrepreneurship: adaptability, calculated risk-taking, strategic alliance-building, and innovating with courage, among them. The unexpected obstacles will keep coming – and so will the stories of resilient entrepreneurs always growing in experience and wisdom. 

Photo: Getty Images