Breaking Precedent

Welcome to Breaking Precedent, the podcast that dives deep into the stories of trailblazers, innovators, and game-changers who are redefining societal precedents. Join us as we sit down with extraordinary individuals who are pushing the boundaries of social norms, challenging precedents, and setting new ones in their fields. Whether it’s in technology, art, social justice, or beyond, Breaking Precedent is your source of inspiration for understanding how precedents are broken and new paths are forged.

Breaking Precedent is a business podcast hosted by Unknown Host, with 65 episodes on record and a Required Pod Score of 80.

Unknown Host hosts Breaking Precedent, a business show with 65 episodes published.

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  Episode #66

  Breaking the 9-to-5: Gary Swart on the Future of Work, Freelance Nation, and Betting on Founders

  Sep 24, 20261h 10m

  What happens when you turn down an early job at Netflix, back when it was still just an idea about mailing DVDs, and then spend the next decade proving that work doesn't have to happen in an office? This episode follows Gary Swart from running a parts middleman business in New Jersey to leading oDesk for nearly ten years, the company that later merged with Elance to become Upwork. He explains the criteria he now uses for big career decisions, why weighing the people differently might have sent him to Netflix, and how oDesk made hiring talent anywhere feel normal long before the pandemic forced the issue. Leah Solivan interviews Gary Swart, now an investor at Polaris Partners, about the forks in the road that shaped his career. Swart recounts auditioning for a sales job at Reed Hastings' Pure Software without knowing how to use a mouse, the "battlefield promotions" that followed, and leaving IBM for a startup so low on cash that he refused to mislead a customer about whether it would survive. He explains how a Sigma Partners investor sent him to oDesk, where he went from COO to CEO within weeks and had to pick between staffing firm and marketplace. Swart shares the frameworks he still leans on: reversible versus irreversible decisions, people, PowerPoint and Excel for evaluating founders, and hiring for personal characteristics before skills. He walks through cutting oDesk's take rate from 30% to 10%, guaranteeing work quality, and Reed Hastings' warning that 90% of CEOs are under-focused. He also looks ahead at a future of work that is atomized, more specialized, and augmented by AI, including the app he built himself in an afternoon. And at an age when many of his peers are winding down, he explains why he's still looking for uncomfortable positions, starting with writing a book. Key Insights • If a decision is reversible, make it. Waiting for certainty usually costs more than being wrong. • The people matter more than the title. Swart says he would take a demotion to work with the smartest people he knows. • Two directions is no direction. A company pulled between two business models has to declare a major. • Customers who won't recommend you because you're their "secret weapon" are telling you something good. • Short-term revenue pain, like cutting a take rate, can buy a position competitors can't undercut. • Hire for personal characteristics first, then motivation, skills, and domain knowledge last. • Most founders are under-focused. The current market is usually big enough. Timestamps 00:00 Welcome to Breaking Precedent 02:35 Turning Down Netflix 06:37 Career Decision Framework 09:51 Early Hustle in Manufacturing 11:30 Moving West Into Tech 13:16 Pure Software Baptism 16:19 Frameworks Built From Mistakes 21:50 Finding oDesk and CEO Leap 23:54 Marketplace Versus Staffing 26:38 Remote Work Unlock and Impact 31:59 Tailwinds Behind Remote Work 35:01 Geography and Global Opportunity 36:28 COVID Validation and E Commerce 37:24 Remote Work After COVID 38:49 AI Atomizes Jobs 39:53 Prototyping With AI 41:07 How Investors Decide 43:20 Scrappy Before Scaling 46:07 Pricing Take Rate Shift 49:10 Fixing Marketplace Trust 51:17 Hiring For Traits First 53:52 Backchannel References 55:57 Founder Mistakes Focus 59:26 On Demand Work Future 01:03:06 Breaking Personal Precedent 01:08:12 Closing Reflections Resources Mentioned Upwork: https://www.upwork.com Polaris Partners: https://www.polarispartners.com Thank you to our Precedent Breaking Partners! TaskRabbit: taskrabbit.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast Justworks: justworks.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast Squared Away: gosquaredaway.com/breakingprecedent?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast 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 Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan 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 Solivan founded TaskRabbit, the leading on-demand service marketplace in the world. Connect with Leah Solivan: Website: breakingprecedent.com/ Instagram: https://www.instagram.com/leah_solivan/ X: https://twitter.com/labunleashed?lang=en

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  Episode #64

  Breaking the Code: Anne Wojcicki on Genetics, Reinvention, and Rewriting Consumer Health

  Sep 10, 20261h 10m

  What did Anne Wojcicki see in healthcare that made her leave Wall Street and risk challenging an entire industry to put power back in patients’ hands? Welcome to the brand new season of Breaking Precedent where Leah Solivan interviews 23andMe founder Anne Wojcicki about breaking medical “gatekeeping” by giving consumers direct access to their genetic information and using that data to drive research and prevention. Solivan shares learning she did not carry BRCA2 while pregnant, and Wojcicki recounts motivations shaped by her mother’s fierce self-advocacy, a Stanford community of inquiry, and an immigrant family history that emphasized purpose over materialism. After Yale (biology and a year of hockey) and a Wall Street career that exposed ethical problems in healthcare, Wojcicki drew inspiration from HIV patient advocates to build a platform for people to advocate for themselves. She describes co-founding 23andMe in 2006 with Linda Avey and Paul Cusenza, early public skepticism, the unexpected power of ancestry, medical resistance to broad genetic testing, and how COVID-era telehealth and AI enable new prevention tools. Wojcicki explains buying 23andMe back via a nonprofit to better align incentives, scale research access, and build a subscription product integrating genetics with medical records, self-report data, wearables, and updated insights for personalized risk prediction and guidance. Key Insights • Questioning the status quo can become a foundation for leadership and innovation. • Unexpected experiences can reveal what truly matters and shape a person’s direction. • Advocacy can inspire people to create systems that empower others to speak for themselves. • Different perspectives can come together to create a more powerful and holistic idea. • Breaking precedent often requires challenging assumptions that others accept as normal. • Innovation requires understanding how people actually respond, not just what founders expect. • Responsible innovation means considering the ethical consequences of new technology. • Personal values can become the foundation of a larger mission to empower people and improve systems. • Purpose becomes more powerful when it extends beyond personal success and creates impact for others. Timestamps: 00:00 Welcome to Breaking Precedent 00:42 Anne Wojcicki Introduction 01:58 BRCA2 Midnight Results 03:28 Why 23andMe Started 04:34 Biggest Unanswered Question 06:15 Mom Taught Advocacy 09:22 Rebellious Teacher Mindset 11:12 Debate And Free Thinking 13:52 Stanford Campus Community 15:58 Immigrant Roots And Purpose 18:53 Yale Hockey And Skating 21:30 Culture Shock And Wall Street 22:32 Job Fair Detour 23:10 Swedish Finance Mentors 23:53 Hedge Funds Moral Shock 26:12 HIV Activists Inspire 29:42 Founding 23andMe 32:47 Early Adoption Surprises 36:30 Prevention Meets AI 39:39 Nonprofit Mission Reset 41:44 Drug Discovery Reality 44:26 Genetics For Everyone 47:17 Subscription Future Vision 49:44 Closing Reflections Resources HIV Activist Movement: https://www.hiv.gov?utm_source=chatgpt.com The Michael J. Fox Foundation: https://www.michaeljfox.org?utm_source=chatgpt.com 23andMe Research Institute: https://www.23andme.org/about/?utm_source=chatgpt.com 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 Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan 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 Solivan founded TaskRabbit, the leading on-demand service marketplace in the world. Thank you to our Precedent Breaking Partners! TaskRabbit: taskrabbit.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast Justworks: justworks.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast Squared Away: gosquaredaway.com/breakingprecedent?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast Connect with Leah Solivan: Website: breakingprecedent.com/ Instagram: @leah_solivan X: @labunleashed

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  Episode #63

  Breaking the Script - Season 3

  Sep 3, 20262 min

  Season 3 of Breaking Precedent is here. This season, Leah sits down with founders, athletes, and builders who refused to accept the world as it was handed to them. From a card game that turns into hard business questions, to rewriting the script for life after sports, to reimagining what healthcare could look like if someone actually believed in you — these are conversations about challenging inherited beliefs, collecting skills, and taking your future into your own hands. Welcome to Season 3. Connect with Leah Solivan Website: breakingprecedent.com Instagram: @leah_solivan X: @labunleashed

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  Episode #62

  Breaking the Bank: Aaron Holiday on 645 ventures' data-driven approach to sourcing deals and bringing the invisible to life [Replay]

  Aug 27, 20261h 11m

  This summer, Breaking Precedent is revisiting conversations that feel just as resonant now as when they were first recorded. In this episode, Leah Solivan sits down with Aaron Holiday to explore what it means to challenge the systems and assumptions that determine who gets access to opportunity. Aaron is the co-founder and Managing Partner at 645 Ventures. He oversees the firm’s investing approach, strategy, investor relations, and governance. Since founding 645 Ventures in 2014, Aaron has worked closely with portfolio company founders to strengthen, grow, and scale businesses. Aaron led 645 Ventures early-stage investments in several breakout successes, including Goldbelly, Iterable, FiscalNote, Squire, Resident/Nectar Sleep, FLY Labs (acquired by Google), Source3 (acquired by Facebook), and several other category-defining companies. In 2021, Aaron made the Midas Brink List of VC investor up-and-comers to watch for his involvement and investments in startup companies that have scaled to hundreds of millions in revenues and unicorn status. The conversation traces Aaron’s path from growing up in New Orleans and imagining a different future to studying computer science, working on Wall Street, entering venture capital, and building 645 Ventures. Leah and Aaron explore access to opportunity, mentorship, technology, data-driven investing, the limitations of traditional venture networks, and why finding the best founders requires looking beyond established circles. They also discuss experimentation, giving people a shot, and what it takes to build new systems when the old ones were never designed to include everyone. Relaunch Context This episode originally captured a moment when venture capital was beginning to confront the limitations of traditional networks, narrow sourcing models, and the assumptions about where great founders and companies come from. The replay is preserved because those questions have only become more relevant: how to uncover talent beyond established circles, how technology and data can expand access to opportunity, and how to build investment systems that can see what others overlook. Aaron Holiday’s journey with 645 Ventures offers a powerful look at what happens when you challenge the conventional model and build a new way to bring the invisible to life. Key Insights Growing up in New Orleans taught Aaron to imagine a different world and question the assumptions that define the one around him. Breaking precedent often starts with finding people who can show you what is possible beyond the world you already know. Access to information, knowledge, and resources can dramatically change the trajectory of talented people, regardless of where they come from. Aaron saw that venture capital's traditional reliance on established networks could miss promising founders and companies outside those circles. The rapid growth of startup formation created a larger pool of companies that traditional venture firms were not necessarily equipped to discover. Data and software could expand a venture firm's reach by identifying high-potential companies beyond its existing network. 645 Ventures developed a different approach to early-stage investing by combining proprietary software, outbound sourcing, and a new mentality around due diligence. The firm's original fund was designed as a proof of concept for a fundamentally different model of early-stage venture capital. Technology can create societal impact at scale by making products more efficient, expanding their reach, and changing the number of lives they touch. Experimentation is central to innovation, but founders and investors also need systems that protect people when an experiment does not work. The venture industry can reproduce its own limitations when successful firms continue using the same strategies and networks that worked in the past. Opening networks is not simply a diversity strategy—it can be a fundamental requirement for finding the strongest companies in an expanding startup ecosystem. Breaking precedent requires more than identifying what is wrong with an existing system; it requires building a credible alternative and proving that it can work. Timestamps 00:00 Welcome Back to Breaking Precedent 01:20 Meet Aaron Holliday 04:20 New Orleans Roots 05:00 Dreaming Beyond Reality 06:40 Morehouse Leap 08:10 Choosing Computer Science 12:30 Learning Through Collaboration 13:20 Hustleman Origin Story 16:30 Breaking Into Internships 20:20 Goldman Trading Algorithms 24:20 From Goldman to GFI 26:40 Discovering Venture Capital 28:50 Cornell Venture Fund 33:00 Advice To Work With Founders 33:20 Blip TV and Early Web Video 34:20 First VC Role: DFJ Gotham 36:30 Cornell Tech Leap 39:30 Inventing Startup Pedagogy 41:40 Why 645 Was Needed 45:10 Data-Driven Deal Sourcing 48:40 Fund One Proof of Concept 53:30 Scaling Funds Two and Three 58:40 Power Law and The Invisible 01:01:50 New Manager Survival 01:05:40 Rapid Fire: Values and Legacy 01:09:00 Closing Reflections and Outro About the Guest Aaron Holiday is the Founder and Managing Director of 645 Ventures, an early-stage venture capital firm focused on discovering promising founders beyond traditional networks. His journey began in New Orleans and took him through computer science, Wall Street, technology, and venture capital. Aaron co-founded 645 Ventures around a data-driven approach to sourcing startups, using software and technology to identify high-potential companies that might otherwise remain outside established venture networks. His work reflects his belief in expanding access to opportunity and rethinking how the venture industry discovers and supports the next generation of founders. Connect with Leah Solivan Website: breakingprecedent.com Instagram: @leah_solivan X: @labunleashed

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  Episode #61

  Summer Break: How They Broke Precedent - The Origin Stories

  Aug 20, 202645 min

  This special compilation of Breaking Precedent brings together origin stories from people who have each broken precedent in a different way. Across leadership, entrepreneurship, education, music, and social mobility, the episode explores how financial constraints, family sacrifices, limited access, and unfamiliar environments can shape the people who learn to challenge what came before them. Stacy Brown-Philpot reflects on stepping into leadership without initially seeking it and the lessons her family taught her about generosity, self-advocacy, and responsibility. Samara Hernandez shares how growing up with limited resources taught her to make more out of less and find support through community. D-Nice (Derrick Jones) describes how curiosity, creative exploration, and losing everything pushed him to reinvent himself across music, photography, technology, and business. Shiza Shahid discusses breaking precedents because many of them simply did not exist for her. Bianca Gates connects her childhood experiences of exclusion and belonging to the communities she builds today. Bismarck Lepe reflects on the sacrifices his parents made to create opportunities for their children, while Aaron Holiday shares what it meant to leave New Orleans and enter a new environment where few people from his hometown had gone before him. Alejandra Campoverdi explores the complicated emotional experience of being a “first and only,” from social mobility and dual rejection to becoming both a precedent breaker and precedent setter. Together, these stories challenge the myth that success follows a clean, linear path—and show how what people were denied can become the very thing that helps them see, create, and build differently. Key Insights • Constraints can become the training ground for leadership, creativity, and resilience. • Leadership often emerges before people consciously seek leadership roles. • Scarcity can teach people to recognize possibilities and make more out of less. • Curiosity can become a powerful tool for navigating uncertainty and reinvention. • Breaking precedent often means creating a path where no clear precedent exists. • Family sacrifice can become an invisible foundation for future opportunity. • Being a “first” or “only” can involve both breaking old patterns and setting new ones. • Origin stories are rarely linear; the meaningful parts often exist between the traditional markers of success. • Community can provide the support and belonging needed to navigate unfamiliar systems. • The experiences people are forced to navigate can eventually become resources they use to help others. • Changing a cycle is not only about personal achievement—it can make the path easier for the next generation. • Art, entrepreneurship, education, and leadership can all become ways of transforming constraint into possibility. Timestamps: 00:00 Introduction to Breaking precedent 00:54 Accidental Leadership 02:14 Matriarch Lessons 03:54 Only One in Room 06:01 Proving Them Wrong 07:08 Scarcity to Strategy 07:33 Samara Makes More 09:52 D-Nice Reinvention 11:32 Bronx Childhood Curiosity 14:19 Hip Hop to Tech Pivot 16:57 Shiza Breaks Precedent 18:53 Pakistan Childhood Turbulence 20:37 Activism in Pakistan 21:52 Parents and Empowerment 23:37 Accidental Stanford Path 25:51 Purpose at Stanford 26:43 Bianca Gates Origins 27:55 Latina Outsider Experience 29:31 Izmir Family Sacrifice 31:00 Leaving Home for Morehouse 32:13 First Gen Anti Memoir 35:02 Dual Rejection Explained 36:48 Costume Changes and Belonging 38:19 Pride in Being First 41:36 First Gen Fund Launch 44:12 Closing Reflections Featured Voices: Stacy Brown-Philpot, Samara Hernandez, D-Nice (Derrick Jones), Shiza Shahid, Bianca Gates, Bismarck Lepe, Aaron Holiday, Alejandra Campoverdi Resources First Gen Fund : https://www.firstgen.org/?utm_source=chatgpt.com Taskrabbit : https://www.taskrabbit.com/?utm_source=chatgpt.com Morehouse College : https://morehouse.edu/?utm_source=chatgpt.com 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 Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan 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 Solivan founded TaskRabbit, the leading on-demand service marketplace in the world. Connect with Leah Solivan: Website: breakingprecedent.com/ Instagram: @leah_solivan X: @labunleashed

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