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

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