It's Okay To Explore Career Options In Your 20s!
Lisa Winning + Carrie Henderson-McDermott | HeTexted Founders

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Why Should You Care

You might recognize the name HeTexted from their ultra-viral launch a few years ago. Fast-forward to today: HeTexted has transformed into a powerful brand, with a modern-day dating book (think He’s Just Not That Into You for the Facebook generation) and massive traffic to prove it.

This quirky, female-centric advising platform provides both crowd-sourced suggestions and private advice about dating and relationships based on text message screenshots or posted stories.

In their interview, Lisa Winning & Carrie Henderson-McDermott talk about giving up dream jobs to take a risk on an idea, the messy state of dating in the information age, and how to stop comparing your success to that of your friends.


Lisa Winning, founder of HeTexted, is a tech entrepreneur building the destination for relationship advice. Along with co-founder Carrie McDermott, they have built a rapidly growing technology and media platform across web, mobile, book, film and TV.

Winning is an Aussie living in New York City. She is passionate about social innovation, and is on the Board of Pride Live Nation, the Junior Committee for the William J. Clinton Foundation’s Millennium Network, and the Advisory Board of the Annual Youth Assembly at the United Nations.

McDermott comes from Conde Nast, where she was a beauty editor at Glamour magazine. She is currently preparing for the debut of the first HeTexted book, HeTexted: The Ultimate Guide to Decoding Guys.

Made By

Cinematography: Danielle Calodney & Bowie Alexander

Asst Camera: Andreina Velazquez

Edited by: Danielle Calodney

Interviewed by Laura Lehmann

Danielle Calodney

Danielle Calodney has been called the Chief Content Officer for 20to30, and that is the closest she has ever come to a proper title. She produces, shoots, and edits most 20to30 videos while also taking care of the site. She is grateful to live in a time when playing on the internet and making movies can be combined into one job.

In: Tech
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