Revolutionizing the Private Security Industry with Anna Redmond

Anna Redmond is the Founder of Braav, a trailblazing company set to transform the private security industry through innovative AI technology. Having transitioned from an investor to an entrepreneur, Anna brings a wealth of experience in venture capital — an expertise she cultivated after graduating from Harvard — to her current role. She previously co-founded and led HIPPO Reads, a thought leadership platform for Fortune 500 companies that facilitated interaction between the academic and business communities.

In this episode of the Smart Business Revolution Podcast, John Corcoran sits down with Anna Redmond, the Founder of Braav, as they explore Anna’s unconventional path from investor to entrepreneur. Anna shares the inspirations that led to the founding of Braav, provides insights into the specifics of AI adoption in security tasks, and emphasizes the significance of empowering clients and employees through enhanced security practices

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Here’s a Glimpse of What You’ll Hear:

  • [02:09] How childhood bake sales shaped Anna Redmond’s view of entrepreneurship
  • [[03:31] Anna’s journey and challenges in launching a venture capital career
  • [04:17] The transformation of the venture capital industry
  • [07:28] The power of storytelling and charisma in securing venture investments
  • [13:08] Anna’s strategic decision to bootstrap her start-up, HIPPO Reads
  • [14:22] Anna shares the inspiration behind Braav 
  • [20:51] Integrating impactful uses of AI for better security reporting and protocols
  • [24:55] How AI can prevent potential workplace violence and enhance safety protocols
  • [32:23] Embracing technology to evolve remote security measures and services

Resources Mentioned In This Episode

Sponsor: Rise25

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Episode Transcript

John Corcoran 0:00

Today we’re talking about going from investor to entrepreneur. Usually, it’s the other way around, people go from entrepreneur to investor. But my guest today is Anna Redmond. She’s the Founder of a technology platform that’s transforming the private security business. I’ll tell you more about her in a second. So stay tuned.

Intro 0:17

Welcome to the Smart Business Revolution Podcast where we feature top entrepreneurs, business leaders and thought leaders and ask them how they built key relationships to get where they are today. Now, let’s get started with the show.

John Corcoran 0:34

Alright, welcome, everyone. John Corcoran here. I am the host of this show. And I feel very privileged because every week I get to meet and talk to interesting smart CEOs, founders and entrepreneurs from all kinds of companies. We’ve had Netflix and Kinkos, YPO, EO, Grubhub, LendingTree, OpenTable, Act! Software, and many more. And of course, this episode is brought to you by Rise25, which is our company that helps B2B businesses to get client referrals and strategic partnerships with done-for-you podcasts and content marketing. You can go to, and learn all about what we do right there. 

And my guest here today is Anna Redmond. She is the founder of Braav, which is a company that’s on a mission to revolutionize the private security industry through technology. Like many businesses, it came from a personal experience helping a friend who had a security issue. And she realized that this was a really old industry that hadn’t been revolutionized. There’s no quote Uber for the private security industry. And so she launched it with a background, as previously as an investor and venture capital helped her to get that started. So I’m excited to hop into this topic. But Anna, let’s start with I love to ask people about any entrepreneurial side hustles they had as a kid, and you were very smart, you found some slave labor close by. It was your mother who was really good at baking. And so you had bake sales, but kind of was built on the back of your mom who did a lot of the labor in the kitchen helping with the bake sales on the street. Tell us about that experience.

Anna Redmond 2:09

Yeah, I think as a child, you kind of underestimate how hard some things are. And sometimes your wonderful parents are around to make it seem easier than it is. I have these memories of teaming up with a friend and planning these bake sales. And my mom was co-opted into creating the goods for all of these bake sales. And so she’d be slaving away in the kitchen. And our clients would come by, and they’d be like, oh, this is amazing, this is so good. And it was all profit, right? Because she didn’t think to charge us for the time or the flour or the sugar. So I had a little bit of a rose-colored view of entrepreneurship as a kid. 

John Corcoran 2:51

Yeah, these are hot adult profits, all profit margins. Yeah, I’d love to see that P&L from when you were a kid.

Anna Redmond 2:58

We would have gotten venture investment right away.

John Corcoran 3:00

Absolutely. Look at this, up into the right. And so you actually go to college, you go to Harvard, you went into venture after college, venture capital. First of all, what’s it like starting in venture capital? Because more so often, we hear people that exit a business, and then they end up in venture capital. So what was like kind of, were you like the low person on the totem pole kind of thing doing the grunt work? Or did you find that you were doing interesting work?

Anna Redmond 3:31

Yeah, that’s a great question. You know, I’m totally going to date myself here. Back in the day, it was hard, it was hard to get a venture position right out of college. They were few and far between. And I landed at wrested Kenyan partners in LA, which was fantastic. Because there were a lot of partners that really took the analysts along for the process in the meetings, and it was very much like, throw you in, learn by doing. And then, you know, fast forward to today. And by the way, I remember going to all of these events where I was the youngest person in the room by 20 years, generally one of very few women. 

John Corcoran 4:14

And not a lot of women also, too. Yeah.

Anna Redmond 4:17

And it was just like a sea of black suits. Right. And, you know, I felt very much out of place. And then you sort of hit a point where venture transformed, I’m sure your listeners are aware, but a lot more venture capital funds sprung up there, and there was this movement around younger venture capital partners. Now, it’s not super, it’s still unusual, but it’s not insane to see someone in their 20s as the partner of a small fund. And so then we hit a point where, you know, not too long ago, I showed up and I was like, wow, I’m one of the older people in the room. Even though you know, back when I was getting started, I now would have been sort of the appropriate age, and there were lots of women, there were lots of diverse people of all sorts of backgrounds. So it’s been interesting to kind of view that transformation.

John Corcoran 5:12

Why do you think that change has happened? I know that a lot of money has flowed into ventures. There’s a lot more money now than the size of the checks, which are much larger than they were even 20 years ago. 

Anna Redmond 5:25

Yeah, I mean, probably the show Silicon Valley. 

John Corcoran 5:32

Seriously? Everyone’s like, I gotta, I gotta enter this show. This is absolute chaos. It is a great show.

Anna Redmond 5:37

Exactly, though it’s fun. It’s such a great question. I think probably a convergence of factors, right, we had all of the press around some of these massive unicorn companies, that I think, you know, gosh, venture really had this rise in visibility in kind of like the late 90s, early 2000s. But it was a different narrative, because we had a sudden rise in then the sharp crash. And then when I got back in, it was just sort of working its way back up. Whereas now, you know, we’ve had years and years of these massive successes, these stories, although within the venture market, for sure, there have been different trajectories, but from the public perspective, you see these massive successes, you see these entrepreneurs that all sorts of different ages, right, like both older and very young, having these massive exits. 

And so I think it’s honestly, it’s been in the public mind’s eye more so than it used to be. And then for sure, you have all this money flowing in, there are these massive mega funds, these funds and funds that are coming into the market. I feel like there are a lot more investment vehicles that are looking into ventures that maybe weren’t quite ready to do so 20 or 30 years ago.

John Corcoran 6:55

And now, you said that you found during this period of time that one thing that really distinguished the entrepreneurs that came in with an idea was those who really had harness the power of storytelling, and those who really had their story dialed in and was able to explain the purpose behind the company, and wrap around a particular story. So tell us a little about how you kind of came to that realization and how you observed that?

Anna Redmond 7:28

Yeah, I mean, it’s funny, you come in, right, in your very early 20s, and really trying to get the lay of the land, both in venture and in business. And so there are probably a lot of things that I had to learn about. But the thing that you don’t have to learn about is when you see one of the partners literally dozing off during the presentation. It doesn’t take a genius or Harvard degree to be like, yeah, that entrepreneurs probably shouldn’t have gone into all of the technical detail on the product, they should have just talked about impact. 

I will say the entrepreneurs that I saw come in and really hold the attention of the room, just deliver with a ton of charisma, even if their idea wasn’t quite as thought out, even if they had to go through other iterations and fail and then come back and succeed later, they really landed on their feet. And there are multiple people I’m thinking about, as I say this, and I won’t throw out names, because there are lots of these stories there. But you know, you and I know so much of business building is about salesmanship, salespersonship. And if you see a person who can do that, the chances that they’re going to be successful are significantly higher.

John Corcoran 8:49

Yeah, it is such a crazy thing. Because, you know, you hear these stories, always in retrospect about some business that was on the edge of failure, or they iterated or they were living on someone’s couch, you know, and they’re on the verge of success. And then to march in with confidence to a team of people who can write a big check and sell them on this big vision of this big idea that will transform the marketplace. It’s really mind-boggling how someone can do that sort of thing. 

Anna Redmond 9:21

Yeah, absolutely. I think you and I are entrepreneurs, still are. Hearing you talking, you probably have this skill in spades and are just being modest. 

John Corcoran 9:36

I’m not sure I do. I mean, I’ve never raised money from venture capital before. So I guess part of my curiosity around it is the fact that I haven’t done it personally. And I have to admit, my palms get a little sweaty, thinking about the idea, that kind of Silicon Valley idea of like coming into a big conference room with a bunch of people in suits. You know, and they’re like, dance monkey dance, right? Tell us your story, like convince us right? You know, that seems pretty intimidating.

Anna Redmond 10:08

I don’t know, I think it helps that I was on the other side of it for so long. And I realized it was less intimidating and more like, people just want to go on a journey with you. Right? You want to take them on a journey where you’re the champion, and they’re backing you. So they’re the champion behind the champion. 

John Corcoran 10:27

Yeah. Now, while you were doing this, you kind of I don’t know if there’s an epiphany as the right word, but you came to the realization that you would like to be kind of on the other side of the hill, you like to be a founder. And you were looking for the right opportunity, which eventually came along? And I believe that was HIPPO Reads, is that the first one that you designed? Okay. And so tell us what that was?