Between Miami’s bright colors and New York’s monochrome, from Foursquare nostalgia to ChatGPT struggles, Anna Anisin and Courtney Spritzer swap views on fashion, marketing, and more.
Courtney Spritzer grew up in Riverdale, New York, surrounded by two family businesses: a printing company (her first glimpse of entrepreneurship) and fashion boutiques on her father’s side (a hint of style to come). She studied economics at NYU just as Facebook took off, and early roles in finance and marketing led her to American Express, whose social-media experiments showed that the field could be a career.
“They were innovative with social, and that’s when I realized I wanted a career in it,” Courtney says.
Building Socialfly
A Miami trip introduced her to future co-founder Stephanie Cartin. The first interns came via Craigslist, and office space was bartered from a small print shop: social-media help in exchange for desks in the warehouse. The owner also dragged them to a networking group, where they landed their first retainer clients.
After 18 months, their nights-and-weekends project, Socialfly, became a full-time agency that later served global brands and was acquired in 2024.
“Flash forward 13 years—we sold the agency last year,” she notes.
Entrepreneurista Media & the Power of Podcasting
In 2018, looking for a new platform, Courtney and Stephanie launched The Entrepreneurista Podcast, interviewing women founders about funding and failure. Listeners began DM-ing, swapping tips, forming partnerships.
Three years later, the show became Entrepreneurista Media—a membership community, content hub, and the annual Entrepreneurista 100 list.
“Through the podcast we organically built a community of women entrepreneurs,” she says.
Digital-Marketing Trends & the AI Edge
When Socialfly opened, marketers fussed over Facebook pages and Google+. Now brands juggle organic, paid, influencer, affiliate—and generative AI is rewriting the rules.
“AI has flipped the industry. Everyone’s figuring out how to make work faster and more efficient,” she says. Smaller teams can now produce copy, captions, and UGC-style creative that once required large departments.
Style as Brand Strategy
Launching brands in New York, Courtney and Stephanie ignored the city’s all-black uniform. Their shoots popped with hot pinks and citrus yellows—hues that became Entrepreneurista’s palette.
“If you want to stand out, wear color,” she advises.
Today Courtney splits time between New York (black blazers) and Miami (neon sundresses), but color remains central to her brand.
Summary
In closing, Courtney shared advice for women entrepreneurs and joined Anna for a rapid-fire Q&A.
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