Losing love, finding it again, and flying around the country on a private jet

The last decade of Erica O’Grady’s life has certainly had many ups and downs. She lost someone she loved to a heroin overdose, but then found her husband in the most unlikely of places. Most recently, they traveled the country to connect a presidential candidate with his constituents.

[00:00:16.655] – TAMAR
Hey, everybody. I am so super, super psyched, ecstatic, I don’t know what to say. Exceptionally ecstatic. And I use that word very, very purposefully here. I have my awesome friend Erica O’Grady, who I’ve known for a really long time, but not really a really long time. Oh, maybe, I don’t know, 13, 14 years. Is it more? Yeah, maybe. So whatever it is, I have her [here]. She’s here and I am so happy to have her, you, here. Thank you so much for joining. Where are you? And introduce yourself.

[00:00:50.675] – Erica O’Grady
Thanks, Tamar. I’m excited to be here. I’m actually in Fort Collins, Colorado today. I got there not too long ago and I was living in Boulder before that. So we moved to Fort Collins and I love it. Awesome.

[00:01:01.475] – TAMAR
Awesome. So you say today, do you shift gears or you just moved recently?

[00:01:06.515] – Erica O’Grady
Well, for while you’re traveling quite a bit. And so we’d wake up in a different place every day. One day I think we we woke up in Minneapolis and we had breakfast there. We stopped in Davenport, Iowa for lunch and had dinner in Cheyenne. That’s what happens when you get to have a client with a private jet.

[00:01:26.735] – TAMAR
How many of you were on your private jet?

[00:01:29.205] – Erica O’Grady
It held thirteen.

[00:01:30.215] – TAMAR
Oh, that’s fun. So that’s cool. You were very intimate.

[00:01:33.785] – Erica O’Grady
Yeah, it was. It was awesome actually.

[00:01:35.555] – TAMAR
Cool. I don’t know if you want to talk about that a little bit, but I think that’d be fun. But I guess we’ll kind of go into what you do. And if you want to kind of make a foray into your conversation about the client with private jet, by all means.

[00:01:47.015] – Erica O’Grady
Absolutely. So where should we start?

[00:01:48.785] – TAMAR
Tell me about your career story.

[00:01:52.055] – Erica O’Grady
All right. Well, let’s see. I got started in tech in 2006, and I think you and I probably met somewhere around 2007, 2008, definitely in 2008, because we did the Mashable summer tour together. We did seven cities that year and then started working in tech. I got the first congressman on Twitter. He sent the first tweet from the Oval Office. I was working in social media. I’d been a web designer and developer for years and years, my friend Matt, he started WordPress. My friend Christine had named it. So I’ve been using these tools since like before the dawn of time.

[00:02:21.395] – Erica O’Grady
And at some point, not too long after you and I actually met, I think it was in 2010, my life kind of fell apart. And it was I’ve been in a relationship for seven 1/2 years and that relationship went south in a very scary way, like, you know, “the FBI knocked at my door” kind of way. And so my entire life and everything that I knew as it was went away almost overnight, like it’s a kind of a long story and it involves like stolen money from bank accounts and all kinds of other crazy things we don’t have to get into. But I sat on my couch one day. I woke up and I really didn’t have enough money to buy dog food or toilet paper. And I was sitting on my couch crying, not sure what I was going to do after I built this company and had all these things going so well in my life.

[00:03:04.025] – Erica O’Grady
And I just decided that I was going to start living the digital nomad. So I spent two and a half years traveling around different places. I lived in Paris for a month and his little flat right near the Golden Triangle. And I one of the ways that I kind of financed my trip is I stayed at bed and breakfast and I offer them social media and web design for 30 days in exchange for staying for free. So I stayed all these cute little bed and breakfasts all over.

[00:03:29.255] – Erica O’Grady
And when that was over, I was trying to figure out what I want to do next. And I moved to Boulder and at this point I was two hundred and five