Welcome back to STACKED, the show about becoming your own best asset. Today I sat down with Courtney Spritzer, Co-Founder of Entrepreneista, a private membership community of more than 3,500 women entrepreneurs across the U.S., Canada, and beyond. Courtney didn't set out to build a community business — she studied economics at NYU with her sights set on Wall Street, graduated in 2009 into one of the worst financial crises in a century, and spent her first two years out of school underwriting insurance policies in rural Massachusetts. A job at American Express in 2011 changed everything. She was in the room while some of the biggest brands in the world were first figuring out Facebook and Twitter, and she realized social media could actually be a career. She and her business partner, Stephanie, built a social media agency, SocialFly, from nothing — nights and weekends, then a leap of faith, then their first $8,000 month. In 2018, almost as an experiment to learn a new platform for their agency clients, they started the Entrepreneista Podcast. By 2020, it had grown into its own private community — one Courtney and Stephanie eventually spun off entirely, selling SocialFly to focus on what it became. In this episode, Courtney breaks down the one rule that built her entire referral engine, how she balances monetizing a community with keeping it authentic, why the face of a brand doesn't have to be its founder, and why she's convinced every founder — herself included — needs to build AI-first from here on out. This is the episode for anyone building something out of a group chat, a podcast, or a side project, and wondering if it could ever be the real business. Key Topics Covered: — Growing up in a family of entrepreneurs — clothing stores in the Bronx — and trying to do the opposite — Studying economics at NYU and graduating into the 2009 financial crisis — Hitting an $8,000 revenue goal in month one — How SocialFly grew into a full-service digital, paid media, and influencer marketing agency — Starting the Entrepreneista Podcast in 2018 to learn a new platform for clients — Balancing authenticity with monetizing a community — Why 40% of new members join through referrals — How AI agents saved a friend's business roughly $250,000 in three weeks — Why Courtney would build an AI-first business if she started over today — Lightning round Timestamps: 00:00 – Welcome + Introducing Courtney Spritzer 03:45 – Growing Up in a Family of Entrepreneurs in the Bronx 05:26 – Meeting Business Partner Stephanie 06:01 – Building the Agency Nights & Weekends 06:50 – The Leap of Faith: Quitting Corporate for Good 07:01 – Hitting the $8,000 Revenue Goal in Month One 10:41 – Trading Social Media Services for Free Office Space 18:18 – Starting the Entrepreneista Podcast in 2018 18:52 – Spinning Entrepreneista Into Its Own Company During the Pandemic 21:05 – Selling SocialFly to Focus Fully on Entrepreneista 29:03 – The Entrepreneista to Entourage Ambassador Program 30:37 – Building a Personal Brand Without Oversharing 40:20 – Why Courtney Would Build Her Next Business AI-First 44:30 – Lightning Round 46:00 – Where to Find Courtney Spritzer & Entrepreneista Tags: Courtney Spritzer, Entrepreneista, SocialFly, women entrepreneurs, women in business, community building, monetizing community, personal branding, founder-led brand, AI for business, agentic AI, LinkedIn growth, Threads growth, referral marketing, membership community, give first mentality, STACKED podcast, Emily Dempsey, Brickell Babes, female founder podcast Disclaimer:The content shared on this page should not be construed as legal, financial, investment, or medical advice. Your viewing and/or use of this information does not create any kind of client, patient, or fiduciary relationship with us. The contents are intended for general informational purposes only, and you are urged to consult your own advisors concerning your situation and specific questions you may have.
