Female Founders on Tradeoffs, Grit, and Building Support Systems
- Stephanie Roulic
- May 18
- 3 min read
At Startup Boston Week 2025, one of the most candid conversations of the week didn’t focus on fundraising tactics or growth hacks. Instead, it tackled something founders often discuss far less publicly: burnout, bias, resilience, and the support systems required to keep building.
The session Real Talk from the Trenches: Female Founders on Tradeoffs, Grit and Support Systems brought together moderator Sheri Palazzo (Founder, Saplings Consulting) alongside Erin Dewicki (CEO, LymeAlert), Cindy Belardo (CEO, Sunny), and Michelle Chao (Advisor, Phoenix Tailings).
Together, the group represented experience across healthcare innovation, femtech, industrial manufacturing, startup operations, and advising early-stage companies - offering the audience a grounded look at what it really takes to lead through uncertainty.
There Is No Straight Line in Startups
Each founder came to entrepreneurship through a different route.
Erin Dewicki built a career in healthcare before launching Lyme Alert, describing herself as someone who originally had no interest in startups.
Michelle Chao started in engineering at Markforged before helping build Phoenix Tailings from a backyard concept into a commercial operation.
Cindy Belardo transitioned from nonprofit health education into building Sunny, maker of the first FDA-cleared menstrual cup and applicator.
Their stories served as a reminder that startup founders rarely follow one predictable path. Many arrive after careers in healthcare, manufacturing, education, or corporate roles.
What Founders Were Most Proud Of
When asked what they were most proud of, none of the panelists mentioned valuation.
Belardo pointed to personal growth after six years of navigating startup highs and lows. Chao highlighted Phoenix Tailings’ pilot facility launch, a milestone years in the making. Dewicki spoke about transforming an idea into a mission-driven company with a team committed to solving a real healthcare problem.
It was a useful contrast to the outside narrative around startups. Often, the most meaningful wins are invisible: growth, resilience, and building something real with others.
Being Underestimated Can Become an Advantage
The panel also tackled gender dynamics in entrepreneurship.
Chao shared that in industrial settings, she was often mistaken for someone junior while male colleagues received immediate authority. Dewicki described pitching investors who interrupted her team’s presentation and questioned why three women from MIT would want to stay together as co-founders. Belardo discussed the additional layer of building in femtech, where founders often must educate investors and audiences on the category itself.
Yet the panelists also noted that being underestimated can create opportunity. Lower expectations can make it easier to surprise rooms, outperform assumptions, and build credibility through execution.
Burnout Is Real and Often Rewarded Until It Isn’t
One of the strongest moments of the discussion came when Chao described burnout during an intense fundraising period.
She spoke candidly about sustaining 16-hour days, skipping meals, relying on coffee, and tying her identity too closely to company outcomes. After years of nonstop building, she eventually stepped away, traveled, and fully disconnected for the first time in years.
Her message was clear: startup culture often celebrates unhealthy extremes until the cost becomes unavoidable.
Dewicki shared a parallel story from healthcare during COVID, where nonstop crisis management and insurance battles pushed her to a breaking point. Rather than walk away entirely, she redirected that frustration into graduate school and eventually startup creation.
Every Founder Needs a Personal Board of Directors
The panel repeatedly returned to one theme: nobody should build alone.
Palazzo described her own “personal board of directors,” a trusted group of people with different strengths she can call depending on the challenge. Belardo pointed to family, advisors, and peers who provide perspective and gut checks. Dewicki called hers a “kitchen sink board of advisors,” people she can text honestly when things get hard.
The takeaway for founders in the room was practical: support systems should be built intentionally, not accidentally.
Culture Starts at the Top
When asked how startups can avoid creating burnout cultures for employees, the panel was direct: leadership behavior matters more than slogans.
Chao admitted that while she verbally encouraged employees to take time off, her own nonstop pace sent a stronger message. Team members mirrored what they saw.
For founders, it was a reminder that culture is rarely what’s written in a handbook. It is what leaders normalize every day.
The Bigger Lesson
The conversation stood out because it replaced startup mythology with reality.
Founders are not machines. Great companies are not built through endless exhaustion. And success often depends less on looking polished from the outside and more on building the right systems, boundaries, and people around you.
At a conference filled with tactical advice, this session delivered something just as valuable: honesty.
