Loree:

I’m so excited to talk to you today, and I just really appreciate you taking the time to do this.

 

Anne:

Thank you. It’s a pleasure. And I continue to be in awe of you for just continuing to create new chapters and adventures for yourself. Building on the last chapter, but also just striking out, trying new things and building new valuable entities, and I think your focus on leadership is really timely. And strangely, because there’s a big gap in the conversation today.

 

Loree:

Yeah, no, thank you. I agree. It’s definitely one of the reasons why I wanted to start doing podcasts is to see how important it is to have these conversations. And it’s a topic that’s near and dear to my heart, and I know to yours as well. So I’m excited to learn more about your own leadership journey. And, you know, you work with a lot of leaders now as well as a partner with a firm that’s investing in these young founders and old founders…

 

Anne:

Yeah, yeah, exactly. You know, we’d say the ‘next wave,’ not the next generation.

 

Loree:

I love that. Thank you, and you know, thinking about that it was almost 15 years ago that we first met. I was lucky enough to come work for you at Military.com, and it was just such an amazing team. Such much that like, that team still gets together to this day. We’re still in touch with each other. And I know we were hoping to have a reunion this year, and then Coronavirus, had other plans for us… Personally, I think it just really speaks to the culture that you and Chris created and cultivated at Military.com from the very beginning. So I just wanted to thank you for that because it’s pretty special. You can work for a company and work for a team that has leadership that really creates that type of like almost like it’s like a family.

 

Anne:

Well, you are a big part of that and all the people You hired and inspired and stuff like that. And I, it’s funny because I think of those phrases ‘organizations don’t have culture, they are culture.’ And I think that while leaders can certainly have some role in shaping that and setting context and stuff, but really, I think organizations are less engineered than they are emergent based on the behavior and the interactions that are kind of norms. And so I give credit to the great culture, we had military.com to come to the great team. And the fact that there were lots of culture barons; everyone felt like a cultural baron there in a vocal way. And that made it really good tapestry.

 

Loree:

Yeah, definitely. It was interesting, because, I mean, there were certainly people that had military backgrounds or family members who had been in the military, but there were still plenty of people who didn’t, yet they really identified with the mission of the company, of supporting the active-duty members and veterans.

 

Anne:

Yeah, in that I think it was a real treat because I hadn’t really worked in as much a mission-centric organization before, maybe when I was at the Nabisco. And it was, I mean, fun products, but not exactly the same, although I think you can find meaning in any business. But yeah, it was it was special. And I think that today, people talk a lot about mission-centric businesses back then. I don’t think we talked about it, we think we realized it as much, but it was just kind of embedded.

 

But there were some funny memories that I have at that time. I remember when in kind of the startup world, there was a phrase called ‘the beer test.’ And when you’re interviewing people you think, ‘would you want to go have a beer with this person?’ In retrospect, that was such a bad bar. Right, like we didn’t necessarily subscribe to that or anything like that, but that was pervasive in the culture. And one of the beauties of that team is I think it was pretty diverse across backgrounds and ages and all dimensions, frankly, and partly because the military is so diverse, but we were fortunate, I think, in that era.

 

Loree:

Yeah, you bring up a great point, which is that people tend to want to hang out with people who are like them. And so when you use the beer test as a filter for who you who you want to invite into a company, you’re really not doing yourself any favors. You know, you’re not introducing that diversity that really helps build a better product.

 

Anne:

That’s right. Well, and actually, that’s one of my biggest things with observations about leadership over the years… I think great leaders think about affinity, not identity… meaning how do we get a bunch of people excited about common goals, or common values, even though they approach them from wholly different angles, expertises, backgrounds, and perspectives. And I think good leaders do that now.

 

Loree:

Fantastic. So one of the questions I love to ask my guests is about when they’re growing up… when was the first time you recall that you were able to influence someone to take action?

 

Anne:

So I would say, oddly, a middle school talent show. I was not in the talent show, which is being the challenger onstage is not what I like to do. But I volunteered to be like the CEO of the talent show, and creating like systems and processes and schedules and I loved it, and I felt like I was part of it. And I was very much in the background, but kind of like helping talent flourish. And I realized that could be a very rewarding role.

 

Loree:

It sounds very similar to, you know, the people that you have today.

 

Anne:

Yeah, exactly. But it reminds me of what Ray Dalio wrote in his book, Principles, is sometimes you need to work not just in the business, but on the business. And I felt like… I wasn’t in the show, but I was working on the talent show. Yeah, I think it’s been overlooked a little bit. Like how do you create a system, especially in times like this that are so uncertain… you’re not creating a thing, you’re creating the capability to do whatever is needed.

 

Loree:

Yeah, it reminds me of being in the Navy. We used to talk about how, you know, as pilots, we would go out and fly the missions, but like, everybody on that ship was contributing to that mission getting done. You know, from the cook, who’s peeling potatoes to, you know, the poor Seaman apprentice who’s cleaning the toilets. Everybody is contributing to that effort in one way or the other. And, you know, even though certain parties, sometimes we get the glory for it, or the recognition like it is everybody; everybody has to be on their game.

 

Anne:

Yeah.

 

Loree:

So, when you were growing up, who were some of your role models for leadership?

 

Anne:

So, a friend of mine who now has a business called Collaborative Game; it’s actually a leadership kind of training group. But he says that sometimes the best advice or role models are from dead and distant mentors. And what’s nice about that is like people write books or people that are very distant, but you admire. And I was very fortunate somebody gave me a book about Mary Kay, who started Mary Kay cosmetics. And it is a crazy story. She had a pink Cadillac. And when people who are I think franchisees in the company reached a certain level, they also got pink Cadillacs. And until then, I didn’t even contemplate before that a woman could be an entrepreneur and a founder, and I thought that was wonderful. And I just remember, Wow, she can do that, like maybe I could do something. And so I’m grateful for that because I think that was just outside of my experience, and it was just fun to think about.

I feel like I learned from everybody every day and just trying to admire, you know, of course, my parents. They were really open and encouraging with me to try different things, and I kind of grew up in a small town where you could try things with a great community. And I’m so thankful for many teachers because a lot of teachers just gave it their all. And I think teachers get a bad rap, and I feel just incredibly grateful to those people who cared enough.

 

Loree:

Yeah, and I mean, with teachers the impact that they can have both positive and negative. I can’t tell you how many people I’ve talked to who hate math because of a teacher, which breaks my heart. But there are some people who love a particular topic or even go into that career because they studied that subject and had such an amazing teacher present it to them.

 

Anne:

Right. And I remember the best advice I got in college about courses or something was, ‘it doesn’t matter what you take, it’s who you take that matters.’ And I think that actually is right, especially today… whatever we learn kind of changes; the facts change; things change faster than ever. So the half-life of knowledge is degrading. So just love to learn. Keep doing it.

 

Loree:

What’s the best leadership advice that you’ve been given?