Breaking Precedent

What does it take to quit your job, skip venture capital entirely, and build two seven-figure businesses on relationships alone?

On Breaking Precedent, Leah Solivan talks with Stephanie Cartin, co-founder of Socialfly and Entreprenista, about the day she and co-founder Courtney quit their jobs, May 4, 2012, after ten months of building a social media agency on nights and weekends. Stephanie traces the thread from performing as a child actress in the Washington, DC area, to a Disney Vacation Club presentation at age 11 that led her to Cornell's hotel school and a career at Marriott, to spotting social media's business potential as an early Facebook user. She explains how one networking group, mentor Carrie Kerpen, and the book Built to Sell shaped a fully bootstrapped, all-women agency that grew to seven figures without outside funding.

Stephanie then shares why she split from the agency in 2021 to build Entreprenista into a media company and membership community, the Entreprenista League, now 4,500 members strong, focused on connection, resources, and visibility. She and Leah dig into what still holds women founders back, alternative paths to capital, why AI is leveling the playing field for small businesses, and why she believes real human connection, and in-person community, is the opportunity AI can't replace.

Key Insights

• A calculated leap is different from a reckless one: Stephanie and Courtney built for ten months on the side and made a plan before quitting.
• Relationships compound. A contact from age 11, a friend's mom's old client, and one networking group opened nearly every early door.
• You don't need to be the smartest person in the room. Learn from people who have already built businesses, even in other industries.
• Bootstrapping is a real strategy. Most women-owned businesses are not venture-funded, and debt can work when it funds real growth.
• Build a sellable asset, not just a job for yourself.
• AI can level the playing field on operations, but it can't replace human connection.

Timestamps

00:00 Welcome To Breaking Precedent

00:47 Meet Leah And Stephanie

02:59 Broadway Dreams To Hospitality

05:01 Disney Spark And Cornell Path

07:09 Spotting Social Media Early

10:29 Gut Instinct And Trend Timing

11:40 Theater Skills In Business

13:39 Going All In On Socialfly

16:01 First Clients Through Networking

18:30 Bootstrapping And Women Led Agency

20:36 Mentorship With Carrie Kerpen

22:56 Selling Socialfly Tease

23:17 Building to Sell Mindset

24:49 Why EntrepreNista Started

25:47 Pandemic Pivot and Split

27:32 League Solves Founder Gaps

29:31 Writing a Credibility Book

32:13 What Still Holds Women Back

36:47 AI Tools and Human Connection

39:54 Future Vision and IRL Growth

43:38 Next Gen Rules to Break

45:52 Closing Reflections 

Resources Mentioned

Entreprenista: entreprenista.com

Thank you to our Precedent Breaking Partners!

TaskRabbit: taskrabbit.com

Justworks: justworks.com

Squared Away: gosquaredaway.com/breakingprecedent

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: instagram.com/leah_solivan

X: twitter.com/labunleashed

How do you keep going when your biggest success comes with losing almost everything along the way?

On Breaking Precedent, Kass and Mike Lazerow discuss their book Shoveling Shit: A Love Story and what happens when entrepreneurship and marriage collide, especially while raising three kids. They recount their early entrepreneurial roots, meeting in the mid-’90s internet era, and building Golf.com. They sold it to Chipshot during their honeymoon period, lost access to everything when Chipshot ran out of money, then rebuilt and ultimately sold Golf.com to Time Warner amid Tiger Woods’ rise.

They describe starting Buddy Media in 2007 while juggling a newborn, scaling it, and selling to Salesforce for $745M, yet feeling strained, unhealthy, and disconnected afterward. Now investors, they outline their “Go Gauge” framework for evaluating ideas, argue there’s no perfect time to start, push back on bias against married co-founders, and emphasize embracing the “shoveling” reality while using AI to stay competitive.

Key Insights

• Entrepreneurship is less about avoiding failure and more about learning to keep moving when things fall apart.
• The hardest parts of building a company often happen in the messy middle, when uncertainty, sacrifice, and setbacks become part of the journey.
• Success can look very different behind the scenes, especially when professional achievements come with personal and family costs.
• Complementary strengths between partners can become a powerful advantage when building a company together.
• Setbacks can become turning points when entrepreneurs keep working through the problem instead of staying focused on what went wrong.
• There may never be a “right” time to take the leap.

Timestamps

00:00 Welcome 

02:49 On the Entrepreneurial Journey

07:24 Early Hustles And Roots

10:45 Mike Learns Freedom

13:17 Meeting In Web One

18:17 Golf Dot Com Crash

22:24 Shoveling And Lucky Breaks

26:03 Buddy Media Sacrifices

27:53 Credit And Co Founder Balance

31:42 Exit Aftermath Feelings

33:26 Health Wake Up Call

35:31 Writing The Real Story

36:52 From Founders To Investors

39:25 Go Gauge Framework

43:11 Messy Middle Mindset

44:55 AI As Operating System

48:33 Rethinking Venture Rules

51:09 Venture Capital Reset

55:12 Legacy And Precedent

59:57 Closing Thanks 

Resources Mentioned

Shoveling Shit: A Love Story: https://www.shovelingshit.com/

Golf.com: https://golf.com

Salesforce: https://www.salesforce.com

Warner Media: https://www.warnermedia.com

Thank you to our Precedent Breaking Partners!

Squared Away: gosquaredaway.com/breakingprecedent?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

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

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

What happens when a $648 billion market goes uncounted, and who decided it wasn't worth measuring in the first place?

This episode follows Erin Harkless Moore from the breakfast table in San Antonio, through Goldman Sachs, Cambridge Associates, and Princeton's endowment, to Pivotal, the organization founded by Melinda French Gates, where she builds an investment program aimed at the people and markets capital has overlooked. It's a conversation about who gets funded, who gets to decide, and what changes when you start measuring what finance has ignored.

Leah Solivan interviews Erin about starting her career in a Goldman Sachs group with no female partners, earning the CFA so no one could question her technical credibility, and cold-emailing Harvard Business School alumni to find her way to the allocator side of the table. She shares the index card her husband pushed her to write, a single line about changing how capital is allocated and who is in the room, and how it led to a job she half-thought was a prank, interviewing virtually as Seattle became an early COVID epicenter.

Erin explains why reframing the bar isn't the same as lowering it, using the example of GP commitment requirements that can screen out fund managers who don't come from wealth. She walks through Pivotal's approach of using investing, philanthropy, and advocacy together, how DEI headwinds are showing up in fundraising right now, what she has learned from watching Melinda French Gates prepare for every meeting, and where she sees the next overlooked markets, from women's health to women's sports.

She closes with what she'd write on the index card for the next generation of women building where capital hasn't looked yet.

Key Insights

• Reframing the bar isn't lowering it. It's asking whether you're measuring the risk you actually care about.

• A market nobody has measured is easy to dismiss. Sizing it can make it undeniable.

• Diligence rules like large GP commitments can screen out strong managers who didn't start with wealth.

• Writing a one-line purpose down makes it easier to say no to the wrong opportunity.

• No single tool moves a big problem. Investing, philanthropy, and policy work better together.

• When data alone doesn't change minds, a better story often has to.

• Conviction backed by homework and data is what carries you through the doubt.

Timestamps

00:00 Welcome to Breaking Precedent

02:09 Her Grandma’s Index Card

04:20 San Antonio Roots

08:15 Breakfast and Family Rituals

12:40 Math to Wall Street

17:37 Women in Finance Reality Check

22:29 Writing the Career Index Card

26:35 The Call From Pivotal

29:37 Betting on the Care Economy

31:21 Choosing the Leap

34:30 Sizing the Care Economy

37:33 Reframing the Bar

39:41 Living the Thesis

42:16 All Tools Strategy

45:36 DEI Headwinds Returns

49:41 Lessons From Melinda

51:51 Next Invisible Markets

55:21 Breaking Precedent Legacy

57:13 Conviction for Builders

Resources Mentioned

Pivotal Ventures: https://www.pivotalventures.org

Magnify Ventures: https://www.magnifyventures.com

Cambridge Associates: https://www.cambridgeassociates.com

Thank you to our Precedent Breaking Partners!

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

TaskRabbit: taskrabbit.com/?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

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

What does it take to keep building a workwear brand for a decade after a top VC tells you, in writing, that utility doesn't belong in women's clothing?

This episode traces Sali Christeson's path from a childhood split between a South Carolina farm and her father's rug shop in Istanbul's bazaars to building Argent, the workwear brand she's run for a decade, showing how a VC's rejection, a crisis handled in real time, and a refusal to accept easy either/or choices became the foundation for a company built on her own terms.

Leah Solivan interviews Argent founder and CEO Sali Christeson about building a workwear company outside the traditional venture path after a top-tier VC rejected her pitch in writing with the line that would become fuel for everything that followed: utility doesn't belong in women's clothing. Christeson recounts a childhood shaped by a mother who insisted she build her own career and a father who ran a rug shop in Istanbul's bazaars, an MBA and a rotational program at Cisco that exposed her to gender inequity in real time, and the decision to quit and start a fashion company with no fashion background.

She describes building her own cap table out of values-aligned investors rather than chasing the roughly two percent of venture funding that goes to female founders, being eight months pregnant when COVID hit in March 2020 and closing all four Argent stores within days, and turning a warehouse of unsold hot pink suits into a partnership with Supermajority that sold out in twenty-four hours. Christeson also discusses the decision to pull a planned partnership with Planned Parenthood, finding the right creative partner after years of holding on too tightly, and what a new generation of Gen Z customers is teaching her about Argent's next chapter.

Ten years in, she gives her most honest answer yet to whether anything has actually gotten better for women at work.

Key Insights

• A rejection can be the clearest signal you're onto something: a VC calling an idea overdone often means the market is real and nobody has solved it yet.

• Building a brand as a movement, not just a product, is what keeps customers coming back for a decade instead of a season.

• Being chronically underfunded can sharpen a business by forcing more disciplined decisions than a well-capitalized competitor has to make.

• Fast, decisive action under pressure, like closing every store within days of a crisis, protects the business you're trying to save.

• Timing and story can move product faster than the product itself.

• Knowing when to walk away from a partnership that no longer fits matters as much as knowing when to commit to one.

• Ten years in, the honest answer to "have things gotten better" is rarely a simple yes or no.

Timestamps

00:00 Welcome to Breaking Precedent

00:17 Meet Leah And Sally

02:20 Roots And Style

03:44 Work Ethic And Early Hustles

06:10 Confidence Empathy And Ambition

09:32 Structured Path To Founder

12:18 Cisco Sparks The Idea

15:15 Quitting To Build Argent

17:18 VC Bias And Pocketgate

19:31 Rewriting Fundraising Rules

22:18 World Building The Brand

26:07 Scrappy Funding Advantage

28:50 COVID Shutdown Decisions

31:53 Viral Pink Suit Campaign

33:16 Finding Creative Partner

35:07 Doubling Down Mission

39:01 Gen Z And Community

40:46 Authenticity Over Tradeoffs

42:53 Advice For Women Founders

44:35 Money And Investing Power

46:27 Messy Middle Survival

49:46 Closing Reflections

Resources Mentioned

Supermajority: https://supermajority.com?utm_source

Planned Parenthood: https://www.plannedparenthood.org?utm_source

Thank you to our Precedent Breaking Partners!

TaskRabbit: https://taskrabbit.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Justworks: https://justworks.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Squared Away: https://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

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 Meet Anne Wojcicki

01:58 BRCA Midnight Results

03:27 Ashkenazi Screening Gaps

04:32 Question Everything

06:12 Mom the Advocate

09:17 Rebel Teacher Mindset

12:05 Debate and Free Thinking

14:46 Stanford Community Roots

16:52 Immigrant Purpose Drive

19:42 Yale Hockey and Culture Shock

24:25 Wall Street Detour

26:13 Healthcare Ethics Wakeup

28:21 HIV Activists Inspire

31:24 Founding 23andMe

34:55 Selling Genetics DTC

38:36 Prevention Meets AI

41:45 Nonprofit Mission Shift

43:50 Drug Discovery Reality

46:31 Paying for Prevention

53:00 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

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

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

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

What happens when healthcare innovation stops chasing disruption and starts earning trust?

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 Halle Tecco to explore healthcare as one of the most complex, resistant, and consequential systems in American life.

Halle Tecco is a founder, investor, educator, and system-level thinker who has spent her career seeing around corners in healthcare. From founding Rock Health to backing health innovators, building companies, teaching, writing, and pushing the industry to prove what actually works, Halle has been asking the questions healthcare often avoids: who gets care, who gets left behind, who benefits from complexity, and what would it take to build something meaningfully better?

The conversation traces Halle's path from a practical Midwest upbringing to the early days of digital health, the rise of Rock Health, the pandemic's impact on healthcare technology, and the ideas behind her book, Massively Better Healthcare. Leah and Halle explore access, trust, data, incentives, patient power, women in healthcare leadership, founder responsibility, and why healthcare needs builders who are willing to understand the whole system, not just the product they are trying to sell.

## Relaunch Context

This episode originally captured a moment when healthcare innovation was moving from early digital health optimism into a more serious conversation about proof, trust, outcomes, and responsibility. The replay is preserved because those questions have only become more urgent: how to use technology without losing humanity, how to fix incentives that reward the wrong outcomes, and how to build healthcare systems that serve more people instead of simply extracting more value from them.

Key Insights
Healthcare access is shaped by income, geography, race, job, literacy, time, and support, not only by clinical care.
Engagement with the healthcare system is itself a privilege.
Healthcare innovation has to confront fairness, not just efficiency.
Rock Health was built around the belief that technology talent and healthcare institutions needed a bridge.
The pandemic forced healthcare organizations to adopt technology faster than they had before, and some of that innovation muscle remained.
Healthcare has a data problem in both directions: data is underused for outcomes and misused or exposed through security failures.
Proof of concept is not the same as proof of impact.
Healthcare often has an implementation problem, not an innovation problem.
Founders need to understand when a problem is technological, regulatory, behavioral, or structural.
Medication adherence cannot be solved only with better apps if the biggest barrier is the high cost of prescriptions.
Healthcare deserves beautiful, impressive technology, but it only matters if it improves outcomes, access, cost, or experience.
Venture timelines can conflict with healthcare timelines when investors push growth before evidence is ready.
Patient data, pricing, and options are still too often controlled through information asymmetry.
Annual insurance enrollment creates a short-term incentive system for problems that need long-term solutions.
Massively better healthcare means better access, better continuity, and better alignment between effort and outcome for more people.
Breaking precedent in healthcare means moving wisely, proving what works, and building systems that actually serve.

Timestamps

00:00 Welcome back to Breaking Precedent
00:21 Why Halle Tecco's healthcare insights still matter
01:00 Leah introduces Halle Tecco
02:40 Halle joins the conversation
03:00 Icebreaker: the life experience that changed how Halle thinks about healthcare
03:40 Healthcare as a system of haves and have-nots
05:10 Growing up in a practical Midwest family
07:20 Learning to question systems and fairness
08:40 Seeing healthcare beyond medicine
10:20 Calling out bad actors from outside the system
11:20 Women, leadership, and paternalism in healthcare
13:00 The origin of Rock Health
14:20 Seeing the digital health opportunity before it was obvious
15:00 Bridging Silicon Valley startups and healthcare institutions
16:00 What traditional healthcare got wrong about startups
16:50 How the pandemic forced healthcare technology adoption
18:00 AI adoption, healthcare data, and the next frontier
19:40 Underused data, misused data, and cybersecurity risk
20:30 Healthcare's proof problem
21:30 Proof of concept versus proof of impact
22:40 Myths healthcare founders need to unlearn
23:20 Medication adherence and the real barrier of drug cost
24:20 Why founders need to advocate beyond their own product
25:40 Impressive technology versus meaningful outcomes
27:00 Venture timelines and healthcare evidence
28:40 The danger of grow-at-all-costs thinking in healthcare
29:20 The most dangerous precedent healthcare treats as inevitable
30:00 Paternalism, patient data, and information asymmetry
31:00 Healthcare pricing and the lack of transparency
32:40 Misaligned incentives across payment and outcomes
35:10 Halle's book, Massively Better Healthcare
36:40 Why now is the moment for better healthcare tools
37:00 What "massively better" means
38:00 Who the book is for
39:10 Big precedents, small precedents, and ripple effects
41:20 The uncomfortable truth about incumbents and fairness
42:30 What Halle wants readers to do after finishing the book
45:00 Closing reflection

About the Guest

Halle Tecco is a founder, investor, educator, writer, and healthcare innovation leader. She founded Rock Health, one of the earliest organizations focused on digital health startups, and has spent more than a decade helping builders, funders, and institutions understand how healthcare can change.

Her work sits at the intersection of technology, public health, venture, patient access, and system design. Through investing, teaching, podcasting, writing, and her book Massively Better Healthcare, Halle challenges innovators to move beyond incremental optimization and build healthcare that is meaningfully better for more people.

Connect with Leah

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