One of the biggest differences I see between entrepreneurs and most people is how we approach risk. While many contract into fear, constantly worrying about what could go wrong, entrepreneurs acknowledge the risks but tend to focus more on what could go right. Most entrepreneurs, myself included, are naturally optimistic. This doesn’t mean we ignore potential setbacks—we simply stay focused on our vision, confident in our ability to adjust and solve any challenges that come our way.

I’m a big history guy, so let me share a story that illustrates this well. During the Civil War, General George McClellan was known for his meticulous planning. He spent more time preparing his troops than engaging in battle, often fixating on what the Confederate army might do. General Ulysses S. Grant, on the other hand, didn’t get bogged down by fear of what could go wrong – he just focused on his strategy. Today, Grant is widely celebrated for his pivotal role in leading the Union Army to victory.

This is a great representation of how entrepreneurs approach risk. Many people have a low tolerance for ambiguity and want a clear plan before taking action. Entrepreneurs, however, are comfortable with action despite uncertainty. We don’t need all the answers upfront because we trust our ability to figure things out as they unfold.

For example, during Safer Way’s first year, we lost $23,000 – half of the capital we’d started with. Safer Way had been strictly vegetarian and had a very limited product mix. As we thought about our expansion and merger with Clarksville Natural Grocery, we realized we wanted to serve more people. We decided that Whole Foods Market would have a dedicated meat and seafood department, beer and wine, coffee and tea, and a broader product selection. Yes, Safer Way “failed” in some ways, but as an entrepreneur focused on the bigger picture, I saw this as a learning opportunity that helped us grow. This is the entrepreneurial way—we iterate, adapt, and improve rather than letting fear of failure hold us back.

This isn’t to say that planning and caution aren’t important—they absolutely are. But plans are just that: plans. They’re based on predictions, and predictions can be wrong. Planning is essential, but it shouldn’t be rigid. As entrepreneurs, we need to be ready to pivot when circumstances change. Finding the right balance between careful planning and adaptability is key. You can read more about my specific thoughts on balancing entrepreneurship and business planning here.

People often ask me how I work well with others on my team who may be more risk-averse. That’s why it’s crucial to surround yourself with people who balance you out. While entrepreneurs often serve as visionaries pushing forward, we need people around us who are more prudent and detail-oriented. They help us avoid preventable mistakes. This dynamic works both ways — more cautious Team Members need big-picture, optimistic entrepreneurs to have the courage to take action (even if there are risks) and bring ideas to life. 

I’ve always been intentional about surrounding myself with people who keep me grounded. At Whole Foods, this included Glenda Flanagan, A.C. Gallo, Jim Sud, and Walter Robb. I deeply valued their opinions, and they were never afraid to challenge me when they thought I was making a poor decision. They continue to be my trusted sounding board at Love.Life today, along with Betsy Foster.

At the end of the day, it’s all about mindset. Yes, things could go wrong. But what if they don’t? What if everything works out and we create something amazing? That’s what drives me—the belief that we can figure things out, innovate, adapt, and create something incredible, even when the path isn’t perfectly clear. So, if you’re thinking about starting a new venture or taking a leap into the unknown, don’t let fear hold you back. Acknowledge the risks, surround yourself with people who provide the necessary balance, and stay realistic but optimistic. That’s how we make progress and create meaningful change in the world.