Anna Piñol, partner at NFX, takes us on a candid journey from expanding Amazon in Spain to founding Jupiter and ultimately discovering her true calling in venture capital. She shares powerful reflections on finding alignment, navigating pivots, and riding the waves of technological change, most notably, the rise of AI. Anna’s insights are grounded in personal transformation and professional resilience, urging us to choose curiosity over convention and to build with intention in an age when we can infinitely leverage technology. Whether you're an aspiring founder, builder, or investor, Her story offers both a mirror and a roadmap.

Samir Vasavada, co-founder and CEO of Vise, shares his inspiring journey from launching an AI-powered asset management startup as a teenager to raising more than  $130M from top VCs like Sequoia and Founders Fund. Vasavada discusses navigating the “dark side” of venture funding, the lessons learned from hiring seasoned executives too early, and why the best leaders often come from within. His reflections offer a candid look at staying focused amid hype, aligning incentives, and building a category-defining company where you stay committed to your vision while responding to customer feedback.

Founded by supermodel Karlie Kloss, Kode With Klossy teaches young women and gender expansive youth how to code. The organization supports a community of 11,000 from 100-plus countries over more than a decade to ensure their education is effective. CEO Osi Imeokparia shares how long-term support and mentorship for diverse young coders can lead to success in computer science majors and careers in technology. She and Dani Lucas of McKinsey & Company also address the need for shifts in the industry to tackle the "broken rung" of the tech career ladder, which results in women and underrepresented workers facing challenges in promotions and upward advancement.

Garrett Lord started Handshake to make it easier for students from all backgrounds to find internships. Lord discusses his own experience studying computer science at Michigan Tech and the disparities that leave so many students without exposure to recruiters at their campuses. In democratizing the job search, Lord talks about identifying a two-way marketplace and how to scale helping one student at a time.

Vinay Hiremath shares his entrepreneurial journey as the co-founder of LoomAI, a video messaging platform that grew to 30 million users and was acquired by Atlassian for nearly $1 billion. Vinay chronicles his entrepreneurial journey and its many pivots and adaptations – as well as his post-acquisition period of profound questioning and self-discovery. 

This talk includes references to mental health challenges and substance use. The 988 Suicide and Crisis Lifeline (also at 988lifeline.org) is a hotline for individuals in crisis or for those looking to help someone else. The Crisis Text Line is a texting service for emotional crisis support, text SAVE to 741741. It is free, available 24/7, and confidential.

(EDS NOTE: THIS EPISODE INCLUDES EXPLICIT LANGUAGE.)

Stanley Tang was a junior at Stanford when he started to explore technology solutions for small businesses. Working with local shops got him thinking about food delivery, and while at first the idea didn’t seem scalable, the ingredients for DoorDash began to come together. Recounting how DoorDash’s growth spanned many ups and downs including global crises, Tang shares how resilience is built from pivotal moments, and how leaning on core values in times of stress was instrumental in the success of what is now a $75 billion company.

In this 2016 conversation, Bonny Simi—Olympian, airline pilot, venture capitalist, and entrepreneur—explains how success is built on curiosity, creativity, and the courage to take risks. While in her role with JetBlue, Simi shared how setting bold intentions, building transferable skills, and leveraging parallel career moves shaped her unconventional career. Her insights aren’t just for entrepreneurs—they serve as a reminder that this mindset can be applied to any area of life. With advice like taking risks with confidence and being open to non-traditional paths, Simi—now the president of operations for Joby Aviation—highlights the power of small steps, resilience, and trusting the journey.

Payal Kadakia's 2022 conversation feels as relevant as ever, highlighting the enduring importance of authenticity in strong leadership. In this episode, the founder of ClassPass and the Sa Dance Company shares how integrating her full identity—as both a dancer and a business leader—was crucial to her success. Kadakia discusses the importance of listening to your calling, making values-driven decisions, and resisting the pressure to conform to conventional paths. Her insights on aligning passion with purpose, overcoming failure, and redefining success make this episode a must-listen for anyone aiming to build something meaningful while staying true to themselves.

The episode first aired on February 16, 2022

Justin Kan is an entrepreneur and investor best known as the co-founder of Twitch. In this conversation from 2021, Kan shares candid insights on the highs and lows of entrepreneurship, emphasizing the importance of resilience, self-awareness, and personal well-being. Reflecting on his journey—from founding Twitch to reassessing his motivations—he discusses the challenges of chasing external success and the shift toward finding fulfillment in daily habits, mindfulness, and meaningful work. His perspective highlights how true satisfaction comes not just from achievements, but from aligning one’s work with personal values and well-being.

The episode first aired on October 6, 2021.

In this compelling talk from 2016, Astro Teller, director of Alphabet’s moonshot factory, X, explores how embracing failure fuels groundbreaking innovation. He shares how a culture that rewards audacity and transparency can systematically drive progress, turning ambitious ideas into reality. Teller discusses the importance of pre-mortems, rewarding teams for shutting down projects, and creating an environment where failure is seen as an opportunity for learning rather than a setback. As we revisit this talk, its lessons remain as relevant as ever, offering valuable insights for anyone looking to foster bold thinking and transformative breakthroughs.

The episode first aired on April 20, 2016