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