The Makers Among Us
More than a century before today’s entrepreneurs were building businesses from kitchen tables and coffee shops, Isabella Ross built something far less common: a village newspaper—and a voice of her own.
Founders are often remembered for what they create. Less often are they remembered for the moments that test them. When Isabella Ross launched The Lake Bluff Chat in 1909, she wasn’t simply publishing a newspaper. She was also serving as Lake Bluff’s postmistress, managing two demanding roles while giving the village something it had never had before—a publication devoted entirely to its people. She was, in every sense of the word, a founder. Founders are rarely remembered only for their successes but the moments that test them.
Only months after launching The Chat, Ross found herself at the center of public scrutiny. Federal inspectors discovered shortages in the post office accounts, and newspapers across Chicago quickly picked up the story. Headlines questioned her bookkeeping and, in some cases, her competence. Ross did not deny that mistakes had been made. In an interview published at the time, she candidly admitted that bookkeeping had never been her strength.
“I’m no shark,” she said with her signature honesty, explaining that she had been learning on the job and had even used her own money to correct one accounting error once she discovered it. But she refused to let others write the final chapter. Instead, she turned to the pages of The Lake Bluff Chat.
“Isabella confessed she wasn’t much of a bookkeeper, which gave me enormous relief. If Isabella and I have anything in common, I assume it’s this: we didn’t get into newspapers because we were good at math.” - Megan Paszczykowski, Editor of the Chat, New Series
Writing directly to her readers, Ross explained the circumstances, accepted responsibility where she believed it belonged, and defended her integrity. She asked subscribers for patience, transparency, and understanding—not sympathy. Then she wrote something that feels incredibly modern: Some newspapers, she argued, were willing to “peddle a human soul” simply to sell a few more copies.
As both a newspaper editor and the subject of newspaper headlines, Ross understood something few people ever experience from both sides: words have power. Headlines shape reputations. Stories can inform—or they can exploit. More than a century later, it is tempting to remember Isabella Ross only for the controversy. But perhaps that misses the larger story. She was a woman who saw possibility where others saw limitations. She believed a village deserved its own newspaper, and she built one. She made mistakes, acknowledged them, learned from them, and continued publishing. She understood that creating something meaningful requires not only curiosity, but resilience—the willingness to keep moving forward when the path becomes more difficult than expected.
Today, Lake Bluff continues to be shaped by women with that same instinct.
(Modern) Makers Among Us
Annie Pezza and Kate Jackson on seeking, solving and squashing self-doubt
When most people return from a trip, they unpack their suitcase, scroll through a few photos, tell the same stories to family and friends and move on. Bluffer Annie Pezza wondered what happened to those stories after that. She believed they deserved a place to live. That idea eventually became Pinerary (a blend of the words pin and itinerary), a platform where travelers share the experiences that changed them and inspire others planning adventures of their own. “I didn’t realize this when we first launched,” she says. “I thought it was all about sharing travel.” It turned out to be something much bigger.
Today, Annie describes Pinerary as a community built on generosity, where travelers don’t simply post itineraries; they preserve memories that help someone else discover a place they may never have considered. “What we really want from you is your travel story,” she says. “We all have them.” Those stories serve as a lasting digital travel journal that can be revisited years later, shared with friends or even turned into a photo book. Just as importantly, they help someone else travel a little more thoughtfully.
Starting Pinerary wasn’t easy. In fact, Annie calls it one of the scariest things she’s ever done. She first shared the idea with her husband, Paul, on their anniversary in 2018. While he was working toward his MBA, he encouraged her to take the leap. During the pandemic, Annie immersed herself in the travel industry, researching trends, reaching out to founders, networking and attending conferences but there were inevitable setbacks. After spending a year building the first version of the platform, the project fell apart. “I almost gave up,” she admits. Instead, new connections led her to a different development team, and Pinerary officially launched in July 2024. Building the platform in public has been intimidating. “It’s a community,” she says. “And when you build a community, it usually has to begin with your own.”
Annie describes herself as a seeker. She’s the person who’s always curious about what’s behind the locked door or around the corner with the “Do Not Enter” sign. “That probably got me into trouble as a teenager,” she says with a laugh. “I’ve never been satisfied with a simple, ‘No, you cannot.’ I ask, I find a way, and I usually get my answer.” That curiosity has shaped the way she thinks about travel. She believes the most memorable trips aren’t defined by a checklist of luxury or tourist attractions but by the moments that stay with us long after we return home. “Pinerary is a home for those stories.” She also discovered an unexpected lesson after launch. At first, she asked friends to upload their itineraries. “It sounded like homework,” she laughs. She quickly realized that wasn’t what people wanted to share. Instead, they wanted to tell stories about the meal they still think about years later or the tiny café they stumbled across with the sweet owner. Pinerary takes those stories and turns them into structured itineraries that others can actually use. “I have hundreds saved,” she says. “Usually, it’s a combination of the destination, identifying with the traveler, the photos they shared and how the place impacted them.”
Like many entrepreneurs, she’s wrestled with self-doubt and imposter syndrome. She’s learned to let go of worrying about judgment and focus instead on the value she’s creating. “We’re celebrating some of the best moments of life,” she says. Her family reminds her how far she’s come whenever she begins to question herself. “They’re proud of me for doing something daring.” If Pinerary disappeared tomorrow, Annie says she’d miss the people most of all. The travelers, founders and overall hospitality community that has welcomed her along the way. “I learn every day,” she says. Whether she’s building a travel startup or someday greeting guests as a barista or restaurant hostess, the mission would stay the same. “I want people to feel seen and welcome.”
Every founder begins with a question. For Bluffer Kate Jackson, it started in a classroom. An entrepreneurship lecturer at Northwestern University, Jackson noticed something she couldn’t ignore. After the pandemic, fewer young women were enrolling in her classes. Curious why, she began asking. “The answers kept sounding the same,” she recalls. “Entrepreneurship is for guys.” “Guys are the ones who get funded.” “Startups weren’t built for people like me.”
Jackson understood where those beliefs came from, but she also knew they weren’t true. “The question was never whether these young women were capable,” she says. “I was watching them and I knew they were.”
What was missing wasn’t talent. It was visibility. “If you’ve never watched a woman stand up in a room full of investors and make her case, it’s awfully hard to picture yourself doing it.” That realization became the foundation for Girl Gonna Launch, a nonprofit designed to help girls see themselves as founders, innovators, and leaders before the world tells them otherwise. The organization teaches more than entrepreneurship. Participants learn to think like investors, solve problems creatively, and build confidence through experience. “You have to believe you can do it before you’ll ever try,” Jackson says. “That belief doesn’t come out of nowhere. It gets built.”
For Jackson, success isn’t measured by how many companies' participants eventually launch. She hopes they become women who stay curious, take risks, recover from failure, and trust themselves enough to speak up—even when they’re the only woman in the room. “I want to raise up a generation of girls who understand, without anybody having to tell them, that they belong in every room they walk into,” she says. “Not as guests. Not as the exception. As people who are supposed to be there.”
Her optimism is backed by evidence. Research shows that for every dollar of funding received, startups founded by women generate more revenue than those founded by men - a reminder that the challenge has never been ability, but opportunity. Yet Jackson believes the greatest return isn’t measured in dollars. It’s watching a girl realize she’s capable of building something the world has never seen before.