How do you change the narrative when the system was never designed to include you?

In this episode of Breaking Precedent, Soledad O'Brien joins the show to discuss her illustrious career in journalism, covering critical events from wars to hurricanes, and sharing the humorous contrast between her on-screen cooking segments and her real-life kitchen skills. O'Brien delves into her upbringing as the daughter of an interracial couple in a time when such marriages were illegal, shaping her perspective on education and resilience. Her journey from a production assistant to starting the Starfish Media Group highlights her commitment to centering authentic stories and challenging traditional narratives in media. The conversation covers the impact of storytelling in crises like Hurricane Katrina, the shifts needed in journalistic practices, and the importance of representation in media.

Soledad O’Brien is an award-winning journalist, producer, and media entrepreneur known for centering truth, context, and underreported voices in American storytelling. A former CNN anchor and correspondent, she led groundbreaking documentary series including Black in America, Latino in America, and In America, reshaping how media covers race, policy, and power.

Listeners can learn more about Soledad O’Brien at SoledadProductions and on Instagram @soledadobrien and LinkedIn @Soledadproduction

Resources:

Matter of Fact with Soledad O’Brien

Stand Your Ground Laws

San Quentin State Prison

Show Notes:

00:00 Welcome to Breaking Precedent!

00:30 Soledad's unexpected cooking skills

02:30 Growing up in an interracial family

04:09 “Education is the one thing no one can ever take from you.”

04:30 Early life and sibling dynamics

05:30 Journalistic beginnings and work ethic

14:30 Breaking media norms and covering major events

18:30 Challenges in modern journalism

25:00 Navigating leadership and integrity in journalism

26:00 Navigating authority and career challenges

27:00 Experiences at MSNBC and A KON TV

27:30 Handling criticism and proving oneself

31:00 Starting Starfish Media and breaking new ground

32:30 Telling compelling stories and documentaries

34:00 Balancing career and family life

43:00 The future of media and journalism

49:00 Promoting new documentaries and storytelling

51:00 Representation and impact in journalism

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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:

Website: breakingprecedent.com/

Instagram: @leah_solivan

X: @labunleashed

What would it take to make healthcare massively better?

In this episode of Breaking Precedent, Leah Solivan sits down with Halle Tecco, founder of Rock Health, to unpack why the U.S. healthcare system remains so hard to change—and what it will actually take to fix it.

Drawing from her upbringing in the Midwest, decades of experience across healthcare, investing, public health, and education, and her new book Massively Better Healthcare, Halle explains how incentives, power dynamics, and regulatory capture shape outcomes far more than technology alone. From Medicaid disparities and data misuse to venture capital timelines and the myth of “innovation solves everything,” she challenges founders and leaders to see healthcare as a system—not just a product opportunity.

Together, Leah and Halle explore why healthcare resists scale, how evidence differs from proof of impact, and why founders must often become advocates—not just builders. Halle shares lessons from Rock Health, insights from teaching at Columbia and Harvard, and hard truths about incumbents, misaligned incentives, and what meaningful progress actually looks like.

Halle Tecco is a healthcare investor, educator, and author focused on improving outcomes, access, and equity across the healthcare system. She is the founder of Rock Health, an early-stage venture firm supporting digital health startups, and the author of Massively Better Healthcare: The Innovator’s Guide to Tackling Healthcare’s Biggest Challenges. Her work spans investing, public health, teaching, and policy advocacy, with a mission to make healthcare meaningfully better for more people.

Massively Better Healthcare (Book): https://www.halletecco.com/book
Rock Health: https://rockhealth.com
Cost Plus Drugs (Mark Cuban): https://costplusdrugs.com
Epic Systems (EHR): https://www.epic.com
Cleveland Clinic: https://my.clevelandclinic.org
National Academy of Medicine (Social Determinants of Health context): https://nam.edu
Centers for Medicare & Medicaid Services (CMS): https://www.cms.gov
Menlo Ventures – AI in Healthcare Report: https://menlovc.com/perspective/ai-in-healthcare/

Shownotes
00:00 Welcome to Breaking Precedent
02:10 Icebreaker: A Personal Moment That Changed Halle’s View on Healthcare
06:30 Growing Up in the Midwest and Early Healthcare Experiences
10:45 Fairness, Access, and Social Determinants of Health
15:20 Questioning Systems from the Inside and Outside
19:40 Founding Rock Health and Early Digital Health Investing
24:10 Why Healthcare Resists Scale
28:30 Data, AI, and the Future of Healthcare
33:10 Incentives, Power, and Misalignment
37:20 Writing Massively Better Healthcare
41:00 What Needs to Change and What Innovators Can Do Next
44:30 Final Thoughts

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:

Website: breakingprecedent.com/
Instagram: leah_solivan
X: @labunleashed

What happens when difference becomes a competitive advantage?

In this episode of Breaking Precedent, Leah Solivan sits down with Samara Hernandez, founder of Chingona Ventures, to explore how identity, constraint, and culture can shape leadership in venture capital. From growing up in Mexico to building a venture fund in the United States, Samara reflects on how limited resources, discipline, and an early love of math forged resilience and clarity—and how being underestimated became a source of strength.

Tracing her path from engineering at the University of Michigan to finance at Goldman Sachs, and ultimately to launching her own fund, Samara shares how she learned to turn difference into a competitive edge. Now a venture capitalist and engineer backing bold founders, she brings a philosophy of doing more with less—working to close access gaps, expand opportunity, and redefine leadership in an industry built on pattern-matching.

Samara Hernandez is a venture capitalist and engineer focused on backing bold founders building the future. Born in Mexico and raised in Chicago, her career spans engineering, finance, and early-stage investing, shaped by a philosophy of doing more with less. Through Chingona Ventures, she works to close capital gaps and expand opportunity for underrepresented founders across the innovation economy.

Learn more at chingonaventures.com, and follow Samara on Instagram @chingonaventures and LinkedIn.

Resources

National Venture Capital Association (NVCA)

Venture Forward

SAFE (Simple Agreement for Future Equity)

Show Notes
00:00 Welcome to Breaking Precedent!
02:03 Icebreaker: Turning Differences into Superpowers

03:43 Samara's Childhood and Education

06:59 From Mexico to Chicago: A Family's Journey

07:21 The Significance of Qana Ventures

08:32 Celebrating Hispanic Heritage

09:59 The Power of Community and Upbringing

11:48 Discovering a Passion for Math

13:30 Navigating Education as an Immigrant

17:39 Choosing Engineering and University Life

24:13 From Engineering to Wall Street

26:08 Learning and Growing at Goldman Sachs

30:39 The Intensity of Sales and Moving On

31:12 Mentorship and Business School Journey

32:18 Discovering Venture Capital by Accident

34:13 First Steps in Venture Capital

35:37 Building a Venture Firm from Scratch

36:48 Challenges and Opportunities in Venture Capital

40:31 Scaling Chingona Ventures

44:44 The Power of Representation and Impact

51:07 Investing in the New Majority

57:01 Redefining Success in Venture Capital

01:03:16 Final Thoughts and Advice for Founders

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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:

Website: breakingprecedent.com/
Instagram: leah_solivan
X: @labunleashed