In April 2025, McIntire hosted leading founders from across industries for its second annual Founder’s Forum. Taking part in the daylong event’s panels were three trailblazing entrepreneurs—Liv Cleary (Architecture ’20), Windsor Western, and Ashley Young (McIntire ’09). The three offered students and aspiring founders a behind-the-scenes look at how real businesses are born, built, and scaled.
These influential entrepreneurs shared powerful insights, the inspiration behind their startups, the challenges they overcame, and the strategies that helped them scale their brands in competitive markets.
Why They Chose Entrepreneurship: Passion Meets Market Gaps
Cleary, Founder of The Clearly Collective, turned her artistic instincts into a thriving design business that helps brands and communities express their identities through custom visual storytelling.
Her journey began early: “Apparently when I was 4 years old, I took Popsicle sticks and made coasters. I went out one day around my cul-de-sac to every single person’s door and charged $20 a Popsicle stick coaster,” she says, noting that her parents were unaware she had launched this business. “I came back with about a hundred dollars. As a 4-year-old with that much money, they thought I had stolen it from somebody. They were so confused.”
Cleary can’t remember what inspired her to sell her handiwork to neighbors but believes that “as a wildly creative kid who really had no direction, I needed a validation of creating something that was useful to somebody else. That was a driving factor for me.”
Backed by a design-thinking background from her UVA Architecture major and a minor in Entrepreneurship, Cleary transformed her early passion into a business that caters to both direct-to-consumer markets and major corporate clients seeking distinctive brand narratives.
As Co-Founder of Her Campus Media, Western identified a clear gap in digital content tailored for college women as a student at Harvard. “Our friends from other colleges would say, ‘This is amazing. My college does not have a women’s publication. But if I’m interested in lifestyle journalism versus news journalism, there is no publication for me to write for. Can you help me set up a website so I can start this?’” she recalls.
Her Campus became one of the first college-focused media startups created by women, for women—offering relatable content, community, and career resources. “We got enough of these requests that we realized there was a huge gap in the marketplace, not just for on-campus publications for college students by college students, but also for a national media brand that speaks specifically to college women’s experience.”
This approach positioned the platform as a go-to destination for Gen Z women seeking empowerment and connection. She and her two business partners won Harvard’s Business Plan Competition as students and launched their company in their senior year. “By the time we graduated, we were at 25 campuses,” she says.
For Young, entrepreneurship was born from personal frustration while planning her wedding in 2016. She couldn’t find size-inclusive, flattering bridesmaid gowns for her bridal party. “There was nothing form fitting and flattering for my bridesmaids of all shades, shapes, and sizes,” she recalls. “I finally found something, and when my bridesmaids put it on, they literally did not want to take it off.”
Sensing that gap in the market and seeing some viral success after posts about her wedding drove interest in their dresses led Young to launch Bridal Babes, a bold, community-driven brand redefining the bridal fashion industry by offering inclusive and stylish gown options. Her mission-driven approach immediately resonated with underrepresented customers, fueling the brand’s growth.
Bootstrapping Success: Growing Startups Yourself
All three founders emphasized the power and flexibility of bootstrapping their businesses—building them from scratch with minimal external capital—highlighting different paths to success without outside investment.
Young worked lean and strategically since the beginning. Since launching Bridal Babes, she and her husband relied on that disciplined approach through the challenges of the pandemic to build the company’s resilience.
Western sought to leverage the power of competitions. She used startup pitch competitions to refine her business model and gain exposure, regardless of outcome. “I always tell people to enter a business plan competition if they can,” she says. “Because if nothing else, even if you lose or even if you don’t even get considered for the second round, you have to write down your business. Taking it from idea to business plan is the first essential step.”
Putting the bottom line at the top of her list made the difference for Western. Her Campus Media launched with a clear profit-first mindset—no funding, no fluff. “The entrepreneur eating ramen noodles is very real,” she jokes. But this lean phase forced them to monetize early and innovate consistently, enabling Her Campus to scale sustainably from a grassroots blog into a national media company.
Overcoming Challenges
The three entrepreneurs confronted challenges that tested their resolve and momentarily derailed some of their plans, especially during the COVID-19 pandemic—but their pivot strategies defined their success.
Young saw Bridal Babes’ sales slow when the pandemic hit, but she persevered. Her husband and business partner insisted that she continue “to keep pushing through,” she recalls. The business emerged stronger, doubling down on digital community-building and operational agility. They shifted to a drop-shipping model to cut overhead and improve scalability.
Western transformed crisis into opportunity. Guided by the mantra from one of her mentors, “Never waste a crisis,” Her Campus created a virtual graduation experience for students who had their in-person events canceled in 2020. Amassing more than six hours of content that featured celebrity commencement speakers, valedictorian speeches, and performing student groups, the company live streamed a graduation for the Class of 2020, earning them millions of dollars in brand investment support as well as the Adweek Marketing Campaign of the Year.
Though Cleary launched her company after the major global impacts of the pandemic had lessened, she learned hard lessons around operations. A misstep in choosing a cheap logistics provider taught her to invest wisely in professional services: “It’s especially important to spend money on things that you know you’re not good at,” she cautions. “Someone else is good at it for a reason.”
Entrepreneurial Lessons Worth Learning
These stories from Cleary, Western, and Young offer valuable takeaways for aspiring entrepreneurs:
- Identify authentic market needs—especially those rooted in personal experiences.
- Bootstrap intelligently, with a focus on strategic investment and sustainability.
- View failures as stepping stones and challenges as catalysts for innovation.
- Prioritize inclusivity and community impact—consumers reward brands with purpose.
Their entrepreneurial success stories exemplify McIntire’s values of innovation, resilience, and community leadership. As more students look toward launching their own startups, these founders prove that with vision, discipline, and heart, making an idea a viable business is possible and rewarding.
