During our summer break, we revisit an episode about resilience, pivots, and transformation. Hear Pete Flint on startup survival, Aaron Holiday on breaking into venture capital, Julie Rice on building SoulCycle, Tamara on her ballet breakthrough, Matteo Franceschetti on sleep innovation, Beverly Parenti on coding in prison, and Windy Chien on creativity through daily practice. Each story reveals how uncertainty can become the catalyst for growth.
Listen to the full episodes here:
- House Broken: Pete Flint on Disrupting Real Estate and Building Trulia
Listen here: Apple | Spotify - Breaking the Bank: Aaron Holiday on 645 ventures' data-driven approach to sourcing deals and bringing the invisible to life
Listen here: Apple | Spotify - Break A Sweat: Building Magic On and Off the Bike with Julie Rice of SoulCycle
Listen here: Apple | Spotify - Breaking Pointe: San Francisco Ballet’s Tamara Rojo with Her Bold Vision for a Vibrant Future
Listen here: Apple | Spotify - Take a Break: Matteo Franceschetti on Breaking Sleep Cycles and Turning Rest into a Competitive Advantage with Eight Sleep
Listen here: Apple | Spotify - Prison Break: The Last Mile's Chris and Beverly Share a Blueprint for Change, Born at San Quentin, Scaling Nationwide
Listen here: Apple | Spotify - Broken Records: Windy Chien on changing paths, tying stories into knots, and designing a new language of possibilities
Listen here: Apple | Spotify
Pete Flint
Pete Flint is a serial entrepreneur and investor who co-founded Trulia, steering the company through its IPO and a multi-billion-dollar merger with Zillow. Today, he's a General Partner at NFX, investing in early-stage companies that leverage network effects and cutting-edge technologies.
Listeners can learn more about Pete Flint at
NFX, and on LinkedIn
@PeteFlint
Aaron Holiday
Aaron Holiday is the Co-Founder and Managing Partner of 645 Ventures, a venture capital firm backing early-stage startups led by visionary, often underestimated founders. With a background that bridges entrepreneurship, systems thinking, and institutional investing, Aaron takes a high-conviction, hands-on approach to venture capital.
Julie Rice
Julie Rice is a serial entrepreneur and community-builder best known as the co-founder of SoulCycle and now Peoplehood, a platform for relational fitness and guided group conversation. Her work centers on designing experiences that build human connection at scale.
Listeners can learn more about Julie Rice through LinkedIn
@julierice
Tamara Rojo
Tamara Rojo is a renowned ballerina and artistic director celebrated for her passion, discipline, and vision in the world of dance. Known for breaking traditional molds, Tamara believes that true achievement in the art form isn’t reserved for the most gifted—but for those who are most honest and disciplined with themselves. In this episode, she reflects on the sacrifices required to be “first” and the inspiration she draws from other art forms, powerful friendships, and exhibitions that remind her of the woman she aspires to be. Her story is a masterclass in resilience, artistry, and leading with heart.
Matteo Franceschetti
Matteo Franceschetti is the Co-Founder and CEO of Eight Sleep, the sleep fitness company.Eight Sleep developed a proprietary technology which is redesigning sleep by developing cutting-edge AI and machine learning models to track bio signals during the night and optimizing body recovery and rest while asleep. The end goal of the Pod is to compress sleep and scan your body while asleep to monitor your health. Eight Sleep is currently used by pro athletes and top performers across multiple industries and was recognized as one of TIME’s “Best Inventions” in 2018 and 2019, was named one of Fast Company’s “Most Innovative Companies” in 2018, and has raised over $150M in funding from leading investors, including Founders Fund, Softbank, Khosla Ventures, Y Combinator, Valor Equity Partners, General Catalyst, Naval Ravikant, and Patrick Collison.
Discover your perfect sleep set up -
Take QuizBeverly Parenti
Beverly Parenti is a veteran tech entrepreneur and innovator who co-founded The Last Mile to empower incarcerated individuals, particularly women, with marketable skills. As the first-generation daughter of Holocaust survivors, Beverly's life has been profoundly shaped by her father's experiences during World War II. Her father's story of survival became a guiding light in her life, instilling in her the values of resourcefulness, resilience, and relentless perseverance.
Learn more about The Last Mile at their
website Windy Chien
Windy Chien is an artist best known for The Year of Knots, a daily practice in 2016 where she learned a new knot each day, culminating in a striking installation of 366 knots. A former Apple music executive turned full-time artist, Windy’s work sits at the intersection of craft, design, and personal ritual. Her artistic process emphasizes discipline, flow state, and transformation—both of material and self. In this episode, she reflects on how teaching herself to tie knots became a journey of self-definition, ultimately claiming the title of “artist” through consistent creative labor.
Resources:
Show Notes:
00:00 – Introduction to Breaking Precedent
00:19 – No Plan, Just a Gut Feeling
02:32 – Space for Something New
02:42 – It Didn’t Look Brave at the Time
03: 18 – "He said, ‘Oh, you want to be a venture capitalist.’ And I said, ‘What is that?’"
04:56 – The Moment Before the Story Starts
05:09 – What Would I Actually Want to Do?
08:09 – Before the Movement, a Feeling
08:16 – Maybe the Moment Finds You
09:40 – Maybe the Moment Finds You
09:48 – Sleep Made Me a Founder
10:42 – Readiness is a Practice
10:50 – Building in the Dark
13:02 – Sometimes You Tiptoe
14:17 – The Break Before the Leap Matters
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Leah Solivan is the host of Breaking Precedent, a podcast that explores the stories of innovators who are pushing societal boundaries and setting new precedents in their fields. Leah is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah has 15 years of experience building and creating technology products that have reached millions of people around the globe. She started her career at IBM as an engineer in the software group, working on Lotus Notes and Domino. In 2008, Leah founded TaskRabbit, the leading on-demand service marketplace in the world.
Connect with Leah: