The Not-So-Glamorous Side Of Start Ups
Lisa Winning + Carrie Henderson-McDermott | HeTexted Founders

  • Why You Should Care
  • Bio
  • Read It
  • Made By
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.

Read It

Lisa: I always think of that time when we took the phone call with the lawyers, we couldn’t find a conference room basically to take a phone call with our lawyer and the only quiet spot we could find…

Carrie: was the bathroom, so we go into the bathroom and I’m a little claustrophobic and it’s one of those onesies and Lisa slams the door and I’m like it’s so dark in here, and I barely know Lisa and we’re in this little bathroom and there’s like a toilet next to us and I turn the light the fan goes on, and it’s like “rrrrrr”

Hi I’m Lisa Winning and I am the founder of He Texted

And I’m Carrie McDermott and I’m the co-founder of He Texted

L: So when we first built HeTexted we really just wanted to have a place online where women could go and they could ask any kind of dating or relationship question, and they could be anonymous, and get this sort of instant feedback….there’s this sort of crowd-sourced like throw up your question, get advice, from everyone and anyone.

L: I think before Carrie and I launched the site no one particularly, and I don’t think this a unique situation, no one particularly got it…But carrie and I both just had this really strong feeling that this is something that would take off and that people would respond to, there was this genuine human need.

C: I made the decision to leave Glamour to work with Lisa because Lisa was actually, it was a total accident, she came in for a desk side, which is basically when you come to present your product, but most desksides I took were about lipstick and nail polish….I think we marked like 15 minutes and it ended up being an hour and I Was just obsessed with the idea…I Was kind of like Lisa I would leave my job for this…And she’s like don’t leave your job, I have no money for you! I can’t offer you anything. And then I just left. I put in my 2 weeks the next week. And didn’t look back.

L: We literally couldn’t get anyone to see us twice because they’d be like “Oh really?”

C: Or even once. Most people didn’t want to see us once.

L: The people we were meeting with didn’t understand why young women would be interested in a dating and relationship app.

C: Yeah everyone was like, “no girl cares about text messages. Like that’s so, that’s not true, what girl analyzes text messages?” And we were like, “we need a new crowd.” They were like married men in their 40s, they didn’t get it.

L: It really took us launching everything and then getting some traction and then we were like see! we thought girls would be into it.

C: What we didn’t anticipate is everyone covering it the second they saw it. And it went from AllThingsD to Huffington Post to The Today Show to Good Morning America. It was just everywhere really, really quickly. Like I said the article, I okayed it when I was on my honeymoon because I was like no one will see it, it won’t be a big deal, and all of a sudden I spent the next 3 days of my honeymoon trying to schedule like our Good Morning America segment, I mean it was a crazy time. You can’t anticipate going viral, if you do you’ll never go viral.

L: I mean there will be girls in Sweden asking questions, and girls in Thailand also asking how to tell if a guy likes them, Tel Aviv, yeah they really, these questions are coming from everywhere.
C: And then there’s like 40 year old women being like “I’m divorced, I’ve got two kids, I didn’t grow up texting, this is awful. Do I sign the text?” And we’re like “no, don’t sign the text.”

L: Valentine’s Day is a big ole day for us

L: If you’re dating a girl and it’s been going on for any length of time, you have to acknowledge the day or else you are toast.

C: Do something.

L: Whatever you do.

C: don’t not acknowledge it.

C: grab a piece of paper from the office, draw her damn name name on that heart, color it in with sharpie, give it to her, she’ll melt. That’s a really good idea.

L: That is a good idea

C: I would be such a good guy

C: Yes they all have the same issues. That’s what’s nice about the site. Like people mock it and they’re like oh you guys it’s just like a its a joke and no one’s taking it seriously, and that’s fine, everyone’s entitled to their own opinions, but what we get to see is like the nice side where people are all over the world answering each other’s questions genuinely wanting to help them because they’ve been there too.

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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