C-Suite to Main Street: A Masterclass in Navigating Uncertainty

Every entrepreneur faces uncertainty at some point in their journey. The challenge lies in knowing when to push forward and when to let go, as well as how to navigate the messy middle.

In this installment of CO—’s C-Suite to Main Street series, Editor-in-Chief Jeanette Mulvey sat down with serial entrepreneur Andy Dunn to discuss what it really takes to build a business in times of uncertainty. Drawing on his own journey — from launching Bonobos and Pie to navigating the mental health challenges of entrepreneurship — Dunn offered his candid insights on risk, resilience, and letting go.

In uncertain markets, test small and do your research

Starting a business is inherently uncertain, especially when operating under an untested business model. However, thoughtful testing and customer-centric research can turn a promising idea into a viable brand.

This was the case when Dunn and co-founder Brian Spaly launched Bonobos, one of the first direct-to-consumer e-commerce retailers, in 2007. However, Dunn believed in the business because he personally experienced its value.

“I can remember putting my first pair of Bonobos on … and [feeling] a little more attractive, a little more confident,” shared Dunn. “That was the beginning of knowing that people will like this, because I did.”

To validate their concept, the duo turned to an unconventional setting: a house party. That day, they sold $16,000 worth of pants to their guests.

“That’s where this concept of [launching online] was born,” said Dunn. “People would ask me … ‘Who’s built a brand online?’ The answer was, no one had, and that was a fun challenge to embark on.”

To increase the odds of success in uncharted waters, the duo did their research. Dunn recalls studying the business models of Lands’ End and Zappos for inspiration and adaptation, prioritizing customer service as a differentiator. This not only helped address anticipated e-commerce pain points — like not being able to try on clothes — but also helped the brand gain traction early on.

[Read more: 5 Ways to Expand and Diversify your E-Commerce Business]

Take calculated risks and regularly evaluate your direction

With uncertainty being a part of doing business, some risk is also inevitable. Dunn says taking the right risks is crucial to achieving “asymmetric outcomes” — opportunities where the potential upside significantly outweighs the potential downside.

“My boss at Walmart [after] we sold Bonobos … [was] an amazing entrepreneur named Mark Lore … [who] said most people don’t realize, professionally, how much more risk they can be taking,” recalled Dunn.

Dunn has adopted this mindset with his new startup, Pie. The app aims to target a global, scalable problem — social isolation among young adults — and uses AI, large language models, and community input to connect users through in-person events.

“I want to take a huge swing because if it works, it can make a bigger difference,” Dunn said. “Nothing ventured, nothing gained.”

Beyond taking calculated professional risks, thriving in an unpredictable market also requires a sharp focus on your business’s direction. Dunn encourages entrepreneurs to conduct regular re-evaluations — “definitely once a quarter, and certainly annually” — to cut what’s “vestigial” and tend to what matters most. This may mean saying no to great ideas that don’t serve your current strategy.

“Just because something is a good idea, doesn’t mean it’s a good idea right now,” he added.

[Read more: How Creative Pivots Can Transform a Small Business]

Protect your mental health while building your business

Though rewarding, running a business can take a significant toll on mental health. Dunn has been open about his own experience with mental health and entrepreneurship, including navigating a diagnosis of bipolar I disorder while building Bonobos.

“I was riding two rollercoasters: the entrepreneurial roller coaster and all the highs and lows, as well as a mood disorder that affects [about] 2 to 3% of American adults, but 11% of entrepreneurs,” shared Dunn.

Dunn’s “journey of getting healthy” required him to make several life changes, including giving up alcohol, taking medication, and prioritizing sleep and therapy. This discipline has not only strengthened his willpower but has also helped clarify his priorities.

“Sometimes, I have to abstract away from [the business] and say … ‘It’s just a company,” said Dunn. “If it doesn’t work, it’s going to be OK.”

He also encourages entrepreneurs facing setbacks to separate their self-worth from their business outcomes — a task made easier with professional support.

“When we have suffered a professional loss, we probably can’t deal with that ourselves [or] put that all on our spouse or our best friend,” Dunn advised. “In these periods of crisis … I really advocate for spending [time] with a trained mental health professional who can help us … come out of those challenges on top.”

[Read more: 4 Causes of Entrepreneurial Burnout (And How to Avoid Them)]

Click here to see recaps of past events and information about upcoming dates in our C-Suite to Main Street series.

CO— aims to bring you inspiration from leading respected experts. However, before making any business decision, you should consult a professional who can advise you based on your individual situation.