From Failure to Launch

S2E9: From Uncertainty to Impact: Building Community with Allegra Armas

When Allegra Armas graduated from college, she didn’t have a clear path forward—and she felt like she was already falling behind. But over the past decade, she’s carved out a career rooted in community impact, from connecting fans through sports at the Oakland A’s to driving social impact initiatives at Roku.
In this episode, Keira and Allegra talk about the messy reality of navigating those first jobs, why it’s okay not to have it all figured out at 22, and how to keep your passions alive while climbing the career ladder. Allegra shares her journey of finding purpose in the workplace, her proudest moments at Roku (including building their student app design challenge), and why everything really does happen for a reason.
Whether you’re just starting out or rethinking your next step, this conversation is a reminder that “failure to launch” is just the beginning of the story.

S2E8: Failing Fast: Kerry Rupp on Venture Capital, Startups & Stepping Stones

In this episode of From Failure to Launch, host Keira sits down with Kerry Rupp, General Partner at True Wealth Ventures and one of only two women GPs in a venture capital fund in Texas. Kerry’s career path has been anything but linear — from consulting at Accenture and McKinsey, to joining (and leading) multiple startups, to serving as CEO of DreamIt, a Top Ten US accelerator and VC fund. Along the way, she’s held almost every leadership role imaginable and built a reputation as a champion for women-led businesses that are improving human and environmental health.
Kerry shares:
Why leaving McKinsey was one of her best career decisions 
The lessons she learned taking on countless startup roles 
How “failing fast” shaped her mindset as both an entrepreneur and investor 
What it’s like breaking barriers as a woman in venture capital 
Her journey is a testament to rethinking failure — not as an ending, but as a stepping stone to growth, leadership, and impact.
#FailureToLaunch #Podcast #VentureCapital #WomenInBusiness #Leadership

S2E7: Blue Sky Beginnings: Monica Grant Cohen on Purpose, Resilience, and Redefining Access

In this powerful “From Failure to Launch” episode, host Keira sits down with Monica Grant Cohen, whose journey from a low-income, single-parent household to becoming a leader in philanthropy is nothing short of inspiring. As the eldest daughter who lost her father at age six, Monica shares how her mother’s unwavering strength shaped her—and why she honored her mom by adding her mother’s middle name to her college diploma.
A first-generation college graduate who set out to be a guidance counselor, Monica’s path expanded to higher education, nonprofit innovation, and now community investment at DRW. She talks about her “Blue Sky Thinking” approach, the externship program she built from two employers to over fifteen, and her work tackling both headline-making and quiet crises. Along the way, Monica opens up about imposter syndrome, the realities of real access, and the deep influence of her mother on the woman she is today.

S2E6: Soil, Solar & Second Chances: Cameryn Burnette’s Path to Purpose

In this episode of From Failure to Launch, host Keira sits down with Cameryn Burnette — a PhD candidate at MIT in Material Science for Sustainable Development, Howard University alumna, Schwarzman Scholar, and Special Projects Manager at Energicity.
Cameryn opens up about the moments that shaped her: from growing up amidst environmental disasters that ignited her passion for sustainability, to feeling like a failure after college with no plans lined up. Just one month later, she found herself working with Energicity, bringing solar microgrids to rural communities in West Africa.
They explore her groundbreaking research in soil bacteria preservation at MIT, the reality behind international development work, and the importance of dismantling the “savior complex” often projected onto third-world countries. Cameryn also shares her deep pride in her HBCU roots, her founding of the Howard University Water Environment Association, and how she stays grounded through every success and setback.
Her story is a call to action — to use engineering for the good of humanity, to lean on community, and to face hard challenges with resilience and curiosity.
💡 Call to Action: Tackle the hard stuff. Together. And never stop learning.

S2E5: Keelee Moseley on Redefining Failure

In this episode of From Failure to Launch, host Keira sits down with Keelee Moseley, MBA — a software engineer, educator, and mission-driven problem solver whose career has taken her from Pitts, Pennsylvania, all the way to NASA and beyond.
Keelee opens up about starting off at Penn State with dreams of becoming a computer engineer, only to realize that her superpower wasn’t coding—it was curiosity. From teaching programming at ITT to developing software for capturing orbital images at NASA, and now leading patient accessibility initiatives at Merck, Keelee’s story is anything but linear.
She shares how embracing "failure" helped her pivot industries, redefine success, and break barriers as a woman of color in tech. Tune in to hear how Keelee transformed doubt into drive—and why learning, challenging yourself, and staying mission-focused is the ultimate way to launch a meaningful career.

S2E4: Learning by Doing: Gabriela Rocha on Redefining Education, Leadership & the Future of Work

In this episode of From Failure to Launch, Keira sits down with Gabriela Rocha, cofounder of Laboratoria, to explore her winding journey across continents, languages, and industries — and how she’s helping reshape the future of tech for women across Latin America.
From growing up in Brazil and Los Angeles to co-founding a movement that empowers women from underserved communities to launch tech careers, Gabriela opens up about:
Why she never had a "5-year plan" — and why that’s okay
Building Laboratoria from the ground up
Her belief in learning by doing and student-centered education
Fresh research on gender disparity in tech across Latin America
Maternity penalties, equal pay, and the systems that still need to evolve
What real solutions could look like for working moms and future leaders
Whether you're a founder, a learner, or figuring it all out — this episode is full of honesty, insight, and purpose.

S2E3: From Print Shops to Product Teams: Staci Brookover’s Unconventional Climb

In this inspiring episode of From Failure to Launch, host Keira sits down with her own manager, Staci Brookover, a Project Manager at YETI, whose unconventional journey is anything but ordinary.
Staci shares how she went from barista to daycare worker to spending a decade in printing — climbing from receptionist to production manager — before launching herself into the tech world. Now a seasoned Program Manager at YETI, Staci opens up about leading digital product teams without a college degree, marketing yourself online, and the power of setting clear goals.
With infectious energy and a love for mentoring (including Code2College interns!), Staci talks favorite projects — including building a student-run call center with St. Jude and LeMoyne-Owen College — and offers practical advice on putting in the work to get what you want.
This episode is a masterclass in grit, growth, and redefining success on your own terms.

S2E2: Lead With Love: From Battlefield Intelligence to Bold Investments with Craig Cummings

What happens when a decorated Army intelligence officer, Truman Scholar, and PhD becomes a venture capitalist? You get Craig Cummings — a man whose entire journey has been shaped by leadership, heart, and a deep commitment to service.
In this episode, Craig sits down with Keira to share stories from his time at West Point and 17 years in the military, including how he helped bring the first cellular network to the battlefield. He opens up about meeting his wife at the Truman Scholarship ceremony, the lessons he learned from both leading and following, and how he now uses those insights to back exceptional founders at Moonshots Capital.
This is a conversation about purpose, grit, and the power of leading with love — whether in uniform or in business.
We talk about:
Expectations vs. reality in the military
Leadership that starts with heart
Navigating transitions and reinvention
What he looks for in the founders he invests in
The advice he’d give to his 8-year-old self
If you've ever wondered how to turn discipline into compassion, and success into service — this one’s for you.

S2E1: Redefining Education, Equity, and Innovation with Jeff Livingston

In this immensely anticipated episode of From Failure to Launch, Keira sits down with Jeff Livingston, CEO of EdSolutions and Co-Founder of the Center for Education Market Dynamics (CEMD). Jeff shares his journey from revolutionizing textbooks at McGraw Hill to helping nonprofits and positive-impact organizations reshape education today.
Renowned for his ability to spot talent and his belief in lifelong learning, Jeff dives into why staying on the technological frontier is essential for creating equal opportunities. They also explore the intersection of cultural heritage and access to opportunity, offering insights on how education leaders can adapt to our rapidly changing world. Tune in for a masterclass on innovation, equity, and the future of education.

S1E14: Teaching, Tech & Trust with Kali Peracchia

This week on From Failure to Launch, Keira sits down with Kali Peracchia—AI Instructional Specialist for Denver Public Schools, middle school educator, and PhD candidate at the University of Denver—to explore the intersection of technology, equity, and education. From tackling teacher turnover to building a thriving professional learning community, Kali challenges the scarcity mindset in schools and shares how culturally relevant pedagogy and AI can work hand-in-hand. Tune in for a conversation about reimagining what's possible in the classroom—and what it takes to sustain educators in the process.
Bonus: We also talk hiking, biking, and how nature keeps her grounded!