Episode 92: Brittany Greenfield

Brittany Greenfield - Episode 92

Intro: [00:00:00] Welcome to the Pretty Powerful Podcast, where powerful women are interviewed every week to share real inspiring stories and incredible insight to help women or anyone break the barriers, be a part of innovation, shatter the glass ceiling, and dominate to the top of their sport, industry, or life's mission.

Join us as we celebrate exceptional women and step into our power. And now here's your host, Angela Gennari.

Angela Gennari: Hello, welcome to another episode of the Pretty Powerful Podcast. My name is Angela Gennari, and today I'm here with Brittany Greenfield. Hi, Brittany. Hey, Angela. Thanks for having me. Absolutely. My pleasure.

So Brittany is the CEO and founder of Wabi. She's a leading force in application security, recognized as a top woman in cyber security by Cyber Defense Magazine and her peers in the Cyber Security Excellence Awards, as well as a 40 under 40 by [00:01:00] Boston Business Journal. She is the CEO and founder of Wabi, backed by investors, including Cisco and Workbench, and has pioneered what is now known as the application security posture management space.

Thanks. Wow. That's a mouthful.

With its continuous security platform that bridges the gap between security and development. And that is a really interesting space that we were just talking about, and I can't wait to dive in. So in recognition of its leadership at the forefront of innovation and cybersecurity, Wabi has been named an RSA innovation sandbox finalist, a best DevSecOps solution and publisher's choice in software development, lifecycle security.

Gosh, you're just there's just so many huge, big, complex words in the whole cyber world.

Brittany Greenfield: And as I was saying, it's an alphabet soup, right? We like to distill them down to a bunch of acronyms.

Angela Gennari: And then the

Brittany Greenfield: acronyms take over and you can't remember what the acronyms stood for. [00:02:00] And you're just like, just move on.

Just somebody don't change it tomorrow anyway.

Angela Gennari: And I love the best DevSecOps solution. I'm like the development secure, like we're just going to make up stuff. And we're just going to assume we know what it means.

Brittany Greenfield: Exactly. There's a point in time where I go, but we can actually spend more time talking about it.

Yeah, sure. Sure. It's an acronym, and ESSECOPS happens to be a particular nitpick of mine, sometimes it's the right time to just go with the flow with what everybody calls it, and I'll tackle that challenge of whether or not that word should exist. I

Angela Gennari: love

Brittany Greenfield: it. I love it.

Angela Gennari: So what made you want to get into the cyber security space?

Brittany Greenfield: Yeah. So I actually I've always been in enterprise software. I got into startups coming out of college before it was a normal thing to do. I actually have to explain to my friends what a startup was, not to mention the added complexity of the fact that I was working at a cloud startup at a time.

Cloud was, and they're like, so you're working [00:03:00] in weather technology? I don't know. Give it five years, you'll know what the cloud is. Yeah. Speaking of things that we just start to accept at some point in time. And I got into cyber I was working, I was doing my MBA and I was working for Cisco, which I think the networking company.

And not the food supplier. I was, there you're talking about perimeters which are our homes, right? We try to make sure our homes are safe with different kind of perimeter devices that we monitor, right? It could be an ADT system. It could be a lock on your front door.

And so as a result, because Cisco is sitting at that interface I spent a lot of time with cybersecurity and it was before it had become, dinner table conversation, right? Once a week, there's some breach that's reported, not that it wasn't happening before, and I just fell in love.

It's an area of a lot of intellectual curiosity. I think it's an area that I always, when I actually grew up in Washington, D. C., so for me, cyber had been a three letter agency thing. Huh, you don't have [00:04:00] to be a hacker sitting in a basement. Fighting the good fight against the bad guys.

And it's a place where people are coming to solve problems. And I just absolutely fell in love with it. And you can't pull me out of it.

Angela Gennari: Yeah. And I, that's fascinating because when you're talking about you were doing the whole cloud thing before people knew what that was.

And I remember hearing it for the first time and I was working for a technology company that had just gone. Bust in that whole tech bus thing. So I, it was my first job out of college and some of my colleagues were, we're going to work in this they were calling it cloud technology. And I was like, that doesn't even make sense.

So I went to TV advertising and I was like, I know what that is. It's a real thing. And what you're doing is not a real thing. It's a hundred

Brittany Greenfield: percent. I remember literally having to, I said, I had to explain the cloud and my friends actually asked the right question. Why is it called the cloud?

I don't know, because it's just up there. It's just an omnipresent. I didn't [00:05:00] come up with it. Let's just move on.

Angela Gennari: And I was like, so you're just going to store things in the abyss of space. That doesn't even make sense. And I just. Couldn't wrap my head around it, but man, looking back, I would have been brilliant to go that route.

Because there was just so much that was going to happen and I couldn't see it. I could just couldn't, I couldn't understand it. It was just too foreign to me.

Brittany Greenfield: If it makes you feel any better, or I am a technologist, I work in this industry. I understand how it works. And I still actually have the mystery of how it works, right? I enjoy the mystery of how it works. It's still I wake up and I go, Oh my gosh, we're living in this world where literally I am collaborating. I'm sitting in California. I'm normally Boston based. I'm collaborating with my market team on a report that's coming out on a document that's stored on the web and that has been transmitted.

Over the air, right? So I still love, I like to look at it with those sort of like big wide eyed eyes because I think that this is [00:06:00] what I love about cyber too, you don't want to get so comfortable with it, right? Yeah. You always want to see some of the amazingness of it that we have that really has advanced us and not just taken for granted.

So I do try to keep, I do try to keep the intellectual part of me and the curious part of me separate on that too. So yeah. So it's still baffles me.

Angela Gennari: I know. And it is a fascinating subject and, cybersecurity back before everybody was talking about cybersecurity, like it was just like a CIA thing Oh, you mean the thing that's monitored by the CIA, like it's information transfer and so therefore it must be monitored by some, three led organization in DC.

And so that's, it's just so fascinating that now it has become so commonplace and it's constantly like this. This pool of like good versus bad, is it the dark web or is it just virus protection software?

Brittany Greenfield: Exactly. And it's the, and it's so complex, right? Like we were talking about with this, there's so many different angles of it.

I think that's where. It's scary to [00:07:00] people. Yeah. And the number one piece of advice I give is, and unfortunately, everybody asks anybody in cyber security what their advice for protecting themselves is. And I'm like, that's actually not my realm.

Both: So I go

Brittany Greenfield: to just use common sense. What people Relying on is you having some kind of adrenaline reaction.

So that could be that email. You just started a job. And it could be an email from an HR person or the CEO saying, can you share this information with me? Or I was actually talking to somebody that's in cybersecurity, had been in for 15 years, right on the technical side. And she had just started a new job and got a call from her new boss.

That would like her. And hey, I'm just running. Hey, we've got this event today. Can you go grab some gift cards as door prizes? She drove to the CVS. Wow. And she had one in her hand and she said, what are you doing? She got that, but she was caught in that. I've just started this job. I want to make sure I'm on top of it for my [00:08:00] boss.

And she literally called back and called somebody at the office and said, Hey, is, Jen there? Did you want me to pick up the gift cards for this event? And I think the other thing there's a lot of information available publicly about people. So it's not, that's the biggest thing.

So that's why I say cyber security, the best way to protect all of ourselves is common sense. You're not going to avoid it all. But if you just take a moment to apply what you've learned. All that good thinking that you have gotten you to survive this long. You can avoid a lot of the threats out there as an individual.

Angela Gennari: That's fascinating. Cause literally, as soon as I hire somebody, I have to have the talk with them about within two to three weeks, you're going to get a random text from somebody claiming to be me, and they're going to ask you to get gift cards because I'm in a meeting that is not me. I will never ask you for money.

I will never ask you for gift cards. Like we're okay as a company. I don't need you to. To, put the bill on a gift card for us. And I was like, we're, you will never, ever. And I said, if it's not from my number, [00:09:00] if it's not for me, if I have not in person asked you don't do it. And so I have to do that because it is is guaranteed within two or three weeks of

Brittany Greenfield: being hired.

They will go a hundred percent. We actually had one from one of our investors as a founder. They figured it out.

Both: And

Brittany Greenfield: they did like their year in review video. So it was really easy to identify the portfolio companies and get our email and whatever once you do that. And and so sure enough, all the portcos within one day and I picked it up and you go, Oh my God, it's from somebody that I don't talk to.

All of a sudden it doesn't look right. And there were a couple of little things that I forwarded. Okay. Don't forward these emails. Do not don't open that. Yeah. Yeah. Take a screenshot of it. Yeah. And I sent it to my main contact. I said, I don't think this is real. I think you should know about it. Sure. Yeah.

Thank you very much. Yeah. Again, why don't I do this every day? I tell, I give people this advice and it relied on my [00:10:00] adrenaline reaction.

Angela Gennari: Yeah. Yeah. Yeah. It's crazy because yeah, immediately you think, Oh, it's my boss. And then I had one girl who was in Spain. She was on vacation in Spain. And she was getting texts from a company that were somebody who claimed to be me.

And they're like, Hey, can you please pick up some gift cards? I'm in a meeting. I'm really stuck right now. I could really use your help. And she started doing it. And then all of a sudden she had the wherewithal to say, Hey, this isn't your number. Did you get a different number? And I'm like, Oh my gosh, no.

So like when you respond to them, it immediately, it opens the Pandora's box. So

Brittany Greenfield: I always say don't respond. Don't respond. People often ask me about those weird, like you have a DHL or USPS package and don't respond because they're testing to see if the numbers tell it. Yeah. And that and it's funny you talk about this, a lot of smart people that still go through this and this is one of my areas of concern in the world of AI and all the technology and how people put stuff out there [00:11:00] nowadays.

It would be also really easy. For somebody to actually start to look like you, and and I tell everybody don't use those damn online free headshot generators. The subtext of that is they own your picture forever.

Both: And

Brittany Greenfield: our voices are out there. Our pictures, especially you do a podcast, right?

You've been shared in magazines and whatnot, and it's going to become even easier and somebody is going to go, Oh yeah, I know Angela's on the road. So no wonder it's not her standard background or whatever. Yep. They sound like you and people do just trust nowadays, right? We think about. This is even without AI. Let's think about social media. You see somebody have this perfect bedroom or, or whatnot. And you're like, it's a, it's an Instagram filter.

Angela Gennari: Yeah, exactly. Even zoom, there's so many zoom filters now. And I'm like, Oh, what a cool office. Oh wait, that's not an office.

Brittany Greenfield: Everybody got so good at that. I actually [00:12:00] really enjoyed when people took their zoom backgrounds down because you got to know them. Yeah, for sure. What's their personality? What's their style and stuff? I get in the beginning, or, we've all been in places where you go, you do not want to see the mess behind.

It was a humanizing thing, your craving connections. Yeah,

Angela Gennari: for sure. So your platform is different. So you build software and figure out how to create security within the software. Is that what you do? So we

Brittany Greenfield: don't build the software. Other organizations, right? Every company nowadays is a tech company, right?

Yeah. Starbucks, they say we're a tech company. We just have to spit out coffee at the end of our code. Yeah. And and so R and D happens every place. Software development happens every place. And what we are is a platform that helps manage the set of rules by which softwares is developed securely.

That the analogy I like to use is that we don't just build a house and move somebody. The house and we know whether it's a new build or a renovation. We know if it's commercial or [00:13:00] residential or high rise single family. We know that it's in an existing city, so it has its own rules.

And so the same is true in software development, some of those are externally dictated by some of them are internally dictated much like you might say. I prefer a nice gray to a beige y color on my wall. And and so that set of rules gets applied as software is being developed. But to keep up with the speed of development today, you have to leverage orchestration.

It can't just be a conversation. And that's what we manage. And sometimes It's a hey, Angela, can you toss down the level to make sure the cement is even before we put the carpet on because we don't want anybody tripping. Yeah, other times it's full stop, we're going to wait for the inspector to come in, which is another technology tool in our case, the inspector is going to make sure the wiring's okay before we put it.

Not only is it very unsafe to have wiring behind drywall that's not. That's not correct to code. It's also very [00:14:00] expensive to replace. Yeah. And and so that's what we do. And so that's that system of checks and balances or sometimes shoots and ladders. Cause there is no such thing as perfect security.

Nope. And and so it's what happens when we orchestrate, because this is where technology, I'm a big believer. There are no new problems. They're just new applications of old problems. Whereas we create more data, we exceed human capacity. And so we just help the humans do a better job of developing secure code because until, when we got started, it was still being left as an afterthought and it's still is a little bit, but still

Both: is.

Brittany Greenfield: Recognize they're working on doing better.

Angela Gennari: Yeah. Yeah. It is interesting because there's so many times where you're like, you feel like you're patching things together and I love, that you got your, you're in the process. Like you were saying if you're building a house, you're doing it.

Before we go any further, let's make sure that we do these, the, these really important, critical foundational steps [00:15:00] so that, yeah. We don't have to tear it all back down.

Brittany Greenfield: Exactly. And it's a very human thing. We know sometimes time upfront it may feel like we're slowing down, but it actually saves us time on the tail end.

That's right. Yeah. This is something where I think people, when the world of DevOps one of these other, Alphabet soup names. And so that was the merger of development and operations. So that software could get released more frequently. And right. Because it used to be, I'm going to age myself here, but remember once a year we got an Encarta.

And that was because it took a year to go through all the checks and balances. And so you saw development and operations is more of that back to the house analogy. Hey, does this have four walls? And a door and a window and a closet. Therefore I can call it a bedroom, right? So that's the more sort of binary side of it.

And so when they merged, security was left out of that. We talked about like my least favorite group DevSecOps. And so now security is playing [00:16:00] this catch up. But one of the problems was that as DevOps became the norm of modern software development, like most people don't even really call it DevOps anymore, other than in a specialized function people confused speed and efficiency.

Let me just keep shipping code. Yeah. And that's actually not right. Efficiency and what DevOps is about is about. let me fix the right thing at the right time to save overall time. And it's a bigger picture. It's I I rail on Facebook all the time for popularizing move fast and break things.

You're like no. I

Angela Gennari: know. Along the way. And, your analogy to that is similar to my, a great saw me when people confuse value with price, right? The two things are not the same, right? Are you looking for the best value or the best price? Are you getting, are you low balling and you're just going to take the worst off the shelf crap you can get, or are you getting something that's going to last you and be as much as you need for the job you need done?[00:17:00]

Brittany Greenfield: Exactly. And, oh and that's also the other thing, right? It taps into the what's unique about humans, the psychology of humans. .

.

And it's, I always say a, we all have a pie that we're dividing up and all of, and the composition of our pie is different. And that could be true in a negotiation.

It could be true when you're evaluating a service. This is why, yeah. Bundled cable offerings. We all have a landline that we never use still, right?

Angela Gennari: I only see it pop up on my TV every once in a while. I was like, somebody's calling a number I don't even have a phone for. That's weird.

Brittany Greenfield: But our value is in the package.

It's in the internet. I keep trying to downgrade even my cable package. And they're like, You want your super high speed internet. You're like, cool, fine.

Angela Gennari: I'll keep it. That's

Brittany Greenfield: great. You're going to have every channel and a phone. Congratulations. Yeah, exactly. That's my value pie, high speed internet, high reliability.

And and I think that's something so important, especially in. Starting a company or whether you're an [00:18:00] entrepreneur or whatnot, and you have to really understand there's a reason every investor goes, what's your value prop, right? Yeah, don't ask pricing first. They say, what's your value prop?

How are you going to make somebody's life better? Yes. And it's an exercise, by the way, that's not a one time exercise. It's a constant exercise. Cause from your customers, you've got to be, reintegrating it. And especially when you're in a new market, that's changing quickly as people become educated on it.

Angela Gennari: Yeah, absolutely. So when you're doing cyber which is just this fascinating realm to me, it's like this, the black hole of you could just go on and on. And it's changing so rapidly. How do you keep up? How do you stay engaged and ahead of what's coming?

Brittany Greenfield: It's hard. It's hard, right? In any industry it's hard. This is where newsletters are great and you've got to go find your own. Some of this has always been my personal secret sauce, which is I'm a technologist, but I know better [00:19:00] than to write code. So I like to Stay ahead on market trends, and I actually like to look at the other technologies, right?

So the real goal of cyber, talking about value, the value of cyber is that it allows us to extract maximum value of other technologies. Because if we can't trust them right, then we're never going to get the full value of them. And so I look at. What the other technology trends are right now, basically AI is, yeah.

And right. There's a reason that I have a handful of examples of things that are annoying me about AI and cyber really concerned me right now.

Angela Gennari: AI scares the hell out of me. I'm not even going to lie. Like it's brilliant. Yeah. It's that I'm all for brilliance. I'm all for making my life easier, but there's some things where I'm like this could be like the crazy brilliance where somebody is like a mad scientist is what it feels like.

Brittany Greenfield: And we agreed. And I think there are a bunch of things that are wrong with it. One, everybody's gotten too excited about it too fast. Yes. And you have to remember the dynamics [00:20:00] and I'll talk about it in cyber specifically, the dynamics don't change. There's still an adversary whose job it is to try to get into Angela's computer, whether it's because they don't like you as a person or they're trying to use you against your corporation.

And so when they can take that very personal, It's like a researcher that's researching just one gene, right? Or one disease. Okay. I'm going to find the way to make AI use me versus you, Angela. You don't know where that threat's coming from. So you have to have this broad perimeter defense. Huh.

And so that in cyber, but then we look, I don't know. I just saw it last night for the first time. And I admit it brought a tear to my eye. Have you seen the dove AI image commercial? Share it. And it says, and it has two prompts that it asks. An image generator. Show me beauty and show me. I don't know.

Extraordinary beauty or something like that. And and what caught my attention, I was like, I can't believe I turned the sound on. Can't believe doves using AI generated images. And then I realized what they were doing. They were showing the AI [00:21:00] generated images, but they've actually rolled out some kind of plugin where when you put in with dove, it comes back with real women.

It was unbelievable. And I actually had something, we have AI generated images in some, it's great. That's, and I tried to generate an image of a female CISO for those that aren't familiar with what a CISO it's a chief information security officer. And in cyber, only 25 percent of the workforce is female.

And that. And smaller as you get into the executive ranks

Both: and

Brittany Greenfield: literally the AI image that came back was a kind of feminine face with man's mustache. Oh my gosh, a ponytail. And I was like, I sent it to a CMO friend of mine in cyber. I was like, I can't believe it. I went and reran the prompt several times and then cleared my cache, put in a different inspiration image.

Same thing kept happening. Oh my God. And that this is problem with AI [00:22:00] what we have fed it. Yeah. And it doesn't see that out there. So then we become self reinforcing loop. So anyway, this is a long winded way of answering your question. I like to look at the other technologies that are emerging and say, what's the risk, right?

That's how you stay ahead of the curve on it. That's how I came to found Wabi. I was looking at the fact that organizations were finally, on the tail end of completing DevOps transformations and digital transformations. And I went. Hold on one second. When nine out of 10 breaches begin due to defects in code, this is going to start catching up real fast.

So that's how I say, don't look at, by the time you know what a technology is or whatever the thing is in your industry, by the time you know what a widget is, right? Somebody's already looked at the problem. Look at the environment around it. That's driving that change. And then that's where you can go find a problem.

That's really the trend you should stay ahead of.

Angela Gennari: I love that. And it's similar. So with me and my, so I own a [00:23:00] physical security company. So on the flip side, like we could be a really powerful force together. We would really like it. Okay. Protect the whole universe. It would be amazing. But we have this physical security and, for a while people were trying to figure out how is my company growing so fast.

I don't come from law enforcement. I don't come from a large security company. I don't come from anything that you would consider standard. But the reason that we've grown is because I look at things from a completely different lens. And I look at the other aspects that don't include security to, to solve security problems.

And it has helped it has it's transformed, the way people are looking at events now, and it makes a big difference.

Brittany Greenfield: And I'm a big believer. This is why diversity is important. Yes. It's not about the picture, right? It's not about the splash. It's about diversity of experiences, right? I said, I was outside of cyber for longer than I was inside cyber for a while.

I can't attest to that anymore. But yeah, the years have caught up

Both: and [00:24:00]

Brittany Greenfield: But it was, I had a different lens. I came from the IP world, right? So basically accounting, how do you transform massive amounts of data into actionable insights? That was it. And I'm doing the exact same thing in security today.

How do I, when you have one security manager for every 100 developers, and that ratio is not going to change for a variety of reasons, right? And people don't need to be babysat, right? This is where technology is supposed to help us be more productive. They're never going to be able to keep up.

So how can we turn that into actual insights for all stakeholders? The data is out there. We know what's happening. Software is highly monitored. Security is highly monitored. How do we bring the two together? And when you have a slightly different lens on it, because you haven't been in the weeds so much it's so important.

A friend of mine, had been working for one of the big consulting firms and said, this isn't right for me. She bought a dog walking business, small book of business, but she runs it like a business. Other than she had no experience doing it, but she had a different lens in it. And he has a [00:25:00] very successful business now.

So it applies, I think across all things, fresh eyes are always good. And that's why it's important to have lots of different experiences on your team.

Angela Gennari: Absolutely. And I love it when people ask, We were briefly talking about, people coming to us and asking for advice for business advice, and they get a very different.

I think they get what they're not expecting. It was like, oh, go find investors work hard, do this. And I'm always, I take a totally different approach to all of it. Go sacrifice the hell out of your life. And I was like, go learn what real sacrifice is.

Because if you can't learn it from the beginning, when shit hits the fan and you are in the depths of, what you're trying to do, you have to really be able to pull from inside and keep going.

Brittany Greenfield: It is. Nobody talks about

Angela Gennari: that.

Both: No,

Brittany Greenfield: It's become the hollywoodization of entrepreneurship, not just in taxes across the board

Both: or

Brittany Greenfield: and it's a lot of hard work.[00:26:00]

And. And it's one of the things I do as well, right? There's a I lecture at one of the universities on fundraising. And the first thing I put out there is go, you're thinking of entrepreneurship. Here's this big, big, beautiful rose at the end. And I go, this is the journey you think you're on.

And then I pull up a windy, scary road. I was like, and I'm not trying to scare you, but I am a little bit. Cause I want people to know that there is not, there's not a linear path to success in this. And it's exactly that, you've got to prepare yourself for it. And if you don't, right. By the way, even if you do prepare yourself for it, yeah.

And this is the hardest thing you're ever going to do success or no success. And the act of going on this journey is the hardest thing you're going to do. And anybody that does it deserves a massive pat on the back.

Angela Gennari: Absolutely. Absolutely. And you had a quote in one, [00:27:00] in your bio that I had read previously, it said something like entrepreneurship is where like 99 percent of Or overachievers go to fail.

Brittany Greenfield: It's totally true. That's very legit. Exactly. That's we're a special kind of masochist. Things have been going really well. Yeah. I like to fail constantly because,

Angela Gennari: I like to get up every day and get kicked in the teeth. And then wake up the next day and be excited about getting kicked in the teeth again.

That's just what my life is. Somebody

Brittany Greenfield: was asking me, if you asked me a year ago. But I would watch WWE on a regular basis. And my boyfriend got me into it. And what is you're just as obsessed, like you've made fun of me for this. I said, first of all, I'm fascinated by the business model of it.

I think there's something I really appreciate that these people This physically do what I do every day. And it's just the story of entrepreneurship,

Angela Gennari: right? It's so true. Oh my gosh. Yes. So I, [00:28:00] there's, I had some Lyft drivers when I was in LA over the past couple of days, and I've had three of them, cause they're like a small business.

Pseudo entrepreneur, they're independent contractors working for themselves. And so one of the ladies that was driving with me sweet lady, just really smart very like you could tell she, she was going to do be successful, but she's what advice would you give me? Starting out?

Cause she was doing she had a small business and she's should I go get investors? And I was like no, I was like, learn. And I was like, I need you to minimize your life. I want to give you need to give up every Sunday brunch and Friday night out and do that for about six months while you completely get tunnel vision and you disconnect from all things in life because you're going to have to do that.

You're going to have to be comfortable with getting uncomfortable. Cool.

Brittany Greenfield: Correct. And the one thing though, I'm going to put a caveat in that. Yeah, I did that. Yeah. And we actually bootstrapped. We haven't raised a ton of money. We bootstrapped for exactly that reason. [00:29:00] And and we but you still have to find something that you can do.

That gives you the reward you need, right? Yes. I think part of this glamorization of entrepreneurship is, oh, I'm working 24 7. Inherently you are. 'cause your brain's going on whatever, whatever led you to found this company you're passionate about and your brain's constantly yes. On it. And but if you can't do something to reward yourself, especially since you're failing 99%.

.

Brittany Greenfield: ,

you're not gonna be the best person you can be for it. Yeah. And it's, I learned that the hard way. I learned that after almost nine months where I burnt out and hit Yeah. And, and especially, I was a solo producer at the beginning. I was going and doing the market research.

I was building the website. I was doing all of that. And and then I was like, okay, I've got to find a way to reintroduce cooking with my friends, workout, whatever it is, do activities because you do stuff. For yourself, because that negative cycle and they've done research on it.

Yeah. In a negative cycle, that's just how your brain will start to operate. Yeah.

Angela Gennari: Yeah.

Brittany Greenfield: Find the, you've definitely got to find those [00:30:00] endorphin hits. So even sometimes for me, it's the, I got one of those walking pads at home. Yeah. But I feel good cause I'm moving and that is my reward.

And I'm typing, a blog. Yeah. That was like a reward for me. Oh, this is a way that I can do both. Yeah. Yeah. And also If you're honest with your friends, don't be afraid to be vulnerable. I used to host a Christmas dinner and my best friend, who's an investor, she said, we can potluck this.

Angela Gennari: Yes.

Brittany Greenfield: We can potluck wine. We can potluck this. Okay, I didn't have to say anything to her. God knows she had picked up enough sushi dinners where she'd always claim it was, Oh no. It's my turn to buy. Yeah, I knew what she was doing. I appreciate it. So that's the other thing. Let your friends be there for you, whether it's emotional support or throwing ideas out there.

They know you're going through something hard. If you don't share that with them, you're going to feel even more alone.

Angela Gennari: Oh yeah. A hundred percent. And one of the things that I was, encouraging her to do Find a tribe of people who want the same thing or who are trying to [00:31:00] do something similar because it will change how you do business.

And I was like, it will encourage you. It will change your day to day structure and you'll have a support system. And you need that because even the female founders' dinner that I went to this week in la, I'm talking to other female founders, the, these 250 most influential or whatever they call, for Ink Magazine.

And I'm talking to these people and we all have the same issues that we've gone through. Cash flow issues and employee management and how do you market to the masses? And so we all have the same challenges and finding those people and creating that tribe is just a godsend.

Brittany Greenfield: It was one of the pieces of advice I got when I started, right? Being a leader is lonely. Being a founder leader is even lonelier. And the first person that gave me this advice said, don't be afraid to be vulnerable.

Both: And

Brittany Greenfield: I rolled it off. It happened to be a male CEO. And I was like, that's such a weird thing.

And I trust him. I love him. Everything. That's such a weird thing. That must just be like, It was a little chip on the female founder shoulder or [00:32:00] whatnot. And about six months later no, I take that back a couple of weeks later, a female CEO said exactly the same thing to me and I went, okay, hold on one second, still didn't land.

And around the same time that I was burning out, running into the wall, everything, I went, you can't solve your problems if you don't tell anybody about them because there are other people out there. And sometimes it could be, I call it my personal board of advisors, right? My friends. They may not actually understand what I'm going through, but they're sounding bored or with an employee and eventually I, parted ways with the employee and my friend said, don't you remember two months ago you said you saw the early signs and it was driving you nuts and you were trying to give her the benefit of the doubt that, and I gaslit myself.

And and and then there's those communities where they are going through it. I've said I've always said I want to start founders [00:33:00] club. What happens at founders club stays at founders club. I know. So true. I'm happy, right? Let's talk cash flow, what to do, and this is a safe conversation.

Yep. Yep. It's a safe conversation and sometimes it also, it's important with investors, right? I've had other founders call me and go, Hey, what, let me tell you a story, has this been your experience? Yes. Okay.

Angela Gennari: Yeah. And I find that, the great thing about your friends, like your actual close friends is that they may not have. Any business advice to give to you, but they know you and they know your character and they know your value system. And so they will remind you of that. When you feel like you're drowning in the weeds of the business, they'll remind you of who you are and that's, what's important.

And they can give you that reassurance that Hey, you've been through worse. Like you can,

Brittany Greenfield: you're not that, and you know what, we're on the other side. Yeah.

Angela Gennari: Yeah. Yeah. And if you need to drink wine all night on Friday, we're there for that too. [00:34:00] Yes.

Brittany Greenfield: Exactly.

Angela Gennari: Just having that, two different sets of kind of the, that tribe is really, it's really critical.

But yeah, so I agree. And I was telling her, it's important that you learn how to make sacrifices because you're going to do that a lot. And I was like, you're going to have to give up some time. You're going to have to give up some things that you enjoy doing, but you're right.

Do things that you enjoy. Like I still go to the gym every morning because that is my release. That is my time to myself. And it is what I can do to make myself feel like I've accomplished something because sometimes as a founder, you feel like you've worked your ass off for the past 12 hours and you've gotten nothing done.

Brittany Greenfield: Welcome to most weeks. I'm like, Hey, you get to the end of the week. Today's a Friday. Yeah. Like I have been so flat out busy. I cannot tell you what I did. All I can tell you is what I didn't do.

Angela Gennari: And my 17 things on my to do list on Monday have now become 26. And I've crossed off two things.

Brittany Greenfield: Get all these productivity app things.

I was like, [00:35:00] no, these productivities. Apps do not, there are some good ones out there but they do not understand what this to do list looks like.

Angela Gennari: Truly. So I want to talk a little bit about raising money because, as a tech company, you did raise money. You do have some investors including one really large one.

Cisco is pretty huge name. So how did you go about finding investors? So I'll

Brittany Greenfield: talk about a little more philosophically. Huh. So finding investors is a two way street and that's why I was glad you told the entrepreneur to not get investors immediately.

Angela Gennari: Yes.

Brittany Greenfield: Make sure it's somebody that you click with that.

Yeah. They should be working for you just as much as you should be working for them.

Both: And

Brittany Greenfield: right for them and their LPs and whatnot. And that should be it. And it should be, best investors, best advisors are not the ones that call you and say, what did you do for me today? But rather we'll always pick up the phone when you call and say, how can I help you?

Angela Gennari: Yes.

Brittany Greenfield: So that was [00:36:00] the more holistic approach. The more tactical approach is, and it's very tough in cyber, right? Because it is nuanced, you do have to understand the space. In the place we've had trouble getting diversity of investors, because when you have only a 25 percent workforce in cyber people just don't understand it.

Quite frankly, the realm that we're in, they go, what do you mean? My cook the app I put my money in,

Angela Gennari: Cash app is not secure. That's shocking. It's only been hacked like 18 million times.

Brittany Greenfield: So that's a tough conversation to have, right? You feel like you're telling doesn't exist. And but it is a networking, it's a numbers game.

I would make it more akin to sales, right? Like I said. You have, if you're doing a sales process, you have a persona that you know. So understand who your persona is. Now with that, when you go and you market something, you don't say, I'm [00:37:00] only going to target these three people from the outset, right? No, because those three people at the bottom of your funnel, you do a broad.

And so sometimes it is a lot of emails, whatnot. I'd say the biggest thing is being prepared. Putting yourself out there. So one always have a deck one page or video, whatever, ready to go. Keep that updated. Like I am behind and having mine updated and welcome to my weekend project. I always try to keep that up to date with some current cool message to go out.

The second is always be raising.

Both: Ever

Brittany Greenfield: know when you might meet somebody, it could be on a plane. It could be, different people have different motivations for investing and have that conversation. The third is validate. And especially when you get to larger investors, ask for references. Ask what it's been like to work with them like it's going to be harder on angels, right?

Unless they're a super angel, but that's a personal relationship, right? Have coffee, see what it's like, toss some ideas, right? A, [00:38:00] and then the other thing is, how do I put this? Be. Don't be afraid and learn from my mistakes. Don't be afraid to take a little more money than you need.

Both: Oh,

Brittany Greenfield: interesting. I love

Angela Gennari: this is coming from a woman because we notoriously undersell ourselves and under ask.

Brittany Greenfield: Yeah. So I went in, when I first started fundraising. Here is my five year plan. , Excel spreadsheet, all assumptions. Here's what I need now, here's what I need on the next raise.

Whatever. All things that you should be doing. Yes. And I remember first time I fully presented it and get to the end. I get do you have any questions? And I goes, I very well respected investor in my space. Most people just ask us for a couple million dollars. They don't actually have the reason why.

And it was good and bad. And we could talk, this could be a whole other series. And it was like, but I actually [00:39:00] overwhelmed him. Oh, what I said was I need 12 million. I said, I really just need 2 million to get started. Let's think about my journey. We started walking in 2018. We did our first, a small fundraise in 2019 and we were ready to go GA in 2020.

Think about how my fundraising strategy, and by the way, my peers were going out and just asking for 12 million. Yeah.

Both: And

Brittany Greenfield: so you have to be, there is a little bit of you may think two or three is the right number for you to get started, but you do have to be more aware of market conditions.

Cause for better or worse, that's who I was competing with. And they had a bank of 12 million just because I could do more with less, would it have been nice to be able to tap into that earlier? So you've got to also look at the it's not just here's my assumptions and here's how

Angela Gennari: you

Brittany Greenfield: do have to look at the playing field on it.

And I think the other thing is also something that do is I just did a presentation [00:40:00] for mass challenge which is in Boston for some of their founders that are working with department with NATO. And I said, do as I say not as I did the first time. Yeah, marketing is really important because if we look at the product adoption life cycle with, for those that are familiar with the innovators and the early adopters, they're giving a lot and it's mostly a PR game at that point in time, right?

How are you talking about yourself? How are you being an expert and an advisor to them? How are you building a brand? And and you don't have to. It doesn't have to be expensive, but you need to be out there. And one of my concerns have been we don't have the product yet where I don't want to sell vaporware.

And and, but you could still authentically talk about the problem you're solving and that's really what you're doing with marketing, right? Yeah. Coming full circle in the conversation. How can what I want to do, or some cases what I'm doing right now and future going to do as well. How can I deliver value to you?

Angela Gennari: Yeah.

Brittany Greenfield: And [00:41:00] the buyer persona and profiles a little different. Early different on that. And if you mark it and you just put yourself out there, right? There's a reason you go after the competitions you go after the awards you submit yourself for an ink 250. Yeah.

Angela Gennari: Yeah

Brittany Greenfield: It was one day it'll hit and it's great and you gotta be willing to put yourself out there Yeah, and it doesn't have to cost a lot.

Nope And it's the beauty of, this is actually a place where AI is fantastic now. Yeah. Yeah. Oh yeah. It's

Angela Gennari: like my

Brittany Greenfield: own copy

Angela Gennari: editor. Yeah. Branding is just, I don't think people can appreciate how important branding is. And if you're not updating LinkedIn, if you're not, updating all your marketing materials, if you're not out there, if you're not engaging, if you're not publishing content, you, it goes away.

Just as fast as, Technology moves, marketing moves fast too. So we have to stay on top of it.

Brittany Greenfield: And you've got to brand yourself and it's tough. And there are a couple of aspects we can talk about it. You and the company are one, but [00:42:00] you've got to separate that out, not just for your mental stability, but also for build your own credibility.

And that was something that, marketing's never been my sweet spot. And then you also talk about female founders, how we under represent ourselves. A hundred percent. Yeah. So I am 100 percent that. I am a, my work speaks for itself, right? Yeah. Here I am in cyber, it's technical, people get it.

It's not, it doesn't matter since, it's not, it just, it doesn't matter. You still have to go be your own best advocate and start to work on those things. And so that's one of the other things that I do, because remember the founders, the investors are trying to find you too.

Angela Gennari: Yeah. So if you're

Brittany Greenfield: not there, customers can't find your product and investors can't find you.

Angela Gennari: That's the problem. Yeah. And so if we are underselling ourselves and we're not out there promoting ourselves who, what do we expect to go do that for us?

Brittany Greenfield: Like we have to be out there. It's, and that's how Cisco found us, we put ourselves out there and in our industry, the RSA innovation sandbox is where [00:43:00] all the hot companies come out of, we put ourselves out there as a final, somebody saw me present and reached out to me and then we hit it off. And here we go, right? And that's what it was. And that changed, that certainly changed things.

And and if we hadn't put ourselves out there here, I was going, oh, it's the right time to do it. You really only get one shot. They have very specific parameters And we hadn't, who knows how that story would have

Angela Gennari: gone. Absolutely. And with the 40 under 40, like these are things that, because investors don't just buy your company, they buy you as a founder.

And I've heard this over and over again from investors that like, you can have the best concept for a company, but if you're not the right leader, they're not going to invest. Because it's, it really is dependent on who's leading the company, because if they don't believe in you, you're not going to believe in what you're going to be able to accomplish.

Brittany Greenfield: Exactly. A hundred percent. The two things, bring them on your journey. We talked about being a journey. They want to be on the journey with you, right? The company is still just an entity. They want to be on the [00:44:00] journey with you. So make it easy for them to understand who you are.

Angela Gennari: Yeah. And ultimately, an investor's goal is to exit. And so they're going to exit the company, but they're usually going to stick with the founder. So the next thing you do, they're going to follow you and say, okay, where are we making money next? Yeah. Yeah. So who inspires you?

Brittany Greenfield: I will genuinely say anybody that wants to do this journey, like

Both: worry

Brittany Greenfield: about. Your Uber driver are wonderful leaders out there. But anybody that a lot of them came from being that Uber driver that's because I'm trying to get this started. Anybody that's willing to take this journey and shows up for it every day.

Both: Yeah,

Brittany Greenfield: inspires me. Yeah. We were talking about before it's why I love just chatting with people and I'm in, nobody believes that I'm truly an introvert, but I actually love chatting with strangers because you never know. And you just never know. And it's great to hear their [00:45:00] stories.

And I think that's cool. And then it turns out sometimes it's cool because you go, Oh I just do this. I just founded a cybersecurity company, whatever. Yeah. That's so cool. Oh, I gotta go.

You're doing is also a cool thing to show up for right it's not just about being a cyber founder it could be about being a dog walkers or getting being an Uber driver while you start your own business. That's really this kind of like passion that keeps me going out there that yeah. That one others are doing that to hopefully I'm also charting, of course, that helps more other more people to be able to do it, too.

Angela Gennari: Absolutely. So as a female founder, and I think as women in general, we give away our power all the time to people, in business. And, we take criticism that we shouldn't be taking or we give credit to people that they just steal our credit for something. Can you tell me about a time that you gave away your power and another time that you stepped into your power?

So a time, how much time do we have? [00:46:00]

Brittany Greenfield: Oh, I worked for a company where I was hired to do what I do, which I mentioned was my secret sauce is look ahead in the market and say, that's the next problem that we should go solve. And here's how we're going to go get it. And the person that had hired me loved me, the team that I worked with, they gave me that, that, that.

Opportunity to express myself, so to speak. Yeah. And and we had some change up in roles and I was getting more and more backed into a corner

And, I went presented a new pricing product strategy and why would we do this? Why would we do this? And, filed it. And I was, you can't understand.

You can't understand. And they they hired somebody new and it was almost out of an SNL skit and right. If my title was, the director of widget development, his was director of development for widgets, right? Like one of these things, the things that start to take the toll on you.

And I already [00:47:00] but my I was trying to figure out what next. Yeah. So literally, he said, and I knew it was not there. He goes, Hey, I hear you're the expert in pricing, whatnot. But in this whole thing, I hand him my deck, I wouldn't normally do this and my deck, my Excel, my whatever. A week later, he's been there for 10 days.

He goes and presents it much. They accepted it. And I was like, that was actually like both the, I was put into the corner and took my power back in tech. He's been a leader in tech. And he had said to me not long before this, he said, you say it's so crazy there, why are you judging yourself by those, their standards, and you feel you're being told that you're not doing it right. And not doing enough and not blah, blah, blah, blah, blah, blah, blah, blah, blah, And why are you judging yourself by your standards? It was Stockholm syndrome. And that was both the moment that I felt most backed into the corner because I went, I can't believe they hired somebody to do my job when I had been passing this.

Giving them a level that they have [00:48:00] never seen before and they don't know what to do with. Yeah. And then I took it back because I was like, I am correct out. You need that a little bit of that shell shock, right? This is no longer the place. If this is the world that I'm in, I think there have been other times, especially in the founder's journey where you just have people that are jerks to you.

Angela Gennari: Yep.

Brittany Greenfield: And sometimes the taking it back is sitting here in a room by yourself and saying, Can you believe that? I know. Ask them. Move and just moving on. Yeah. And it's sometimes that's the way that you take back power and it's not avoidance. It's, I cannot control this person. And this person has their own thing that they're going for.

And that, and not dictate my life. Cause if I allow it to dictate my Then I will become consumed by it. And my job is to make sure the business succeeds. That's right. And that is irrelevant. And that's just noise. And I think that's one of the, if you can [00:49:00] remind yourself to your point getting, we get into the weeds too much.

We, we, Too often question our instincts that got us here. All the time I say do as I say, not as I do to founders in general, especially female founders. And sometimes you just have to be willing to say F off. Handle this in however I handle this, but I'm going to move on and leave that in the past.

Done. Yeah.

Angela Gennari: Yeah. That's one of the really critical things. Cause you know, I've had those distractions too, where it's I've had somebody who left my company and immediately started a competing company. And, my other employees are like, why aren't you going after him? Why aren't you going after him?

I'm like. Because it's noise. It's just noise. Like he's not going to be more successful. He's going to be mediocre successful because he was a mediocre employee. I already know this. I'm not going to spend my time chasing after a mediocre company when I have much bigger things on the horizon.

Brittany Greenfield: Exactly. And, I let myself be distracted by that.

[00:50:00] Something. For six months. Yep. It feels like in hindsight, it feels like a six months of my life that I lost. Yeah. Yeah. Cause it ate away at me. And, I think some of this also goes to the it's hard to disassociate yourself from your company, but just remember nobody ever looked, if you decide to start a company, you have decided to do so many things. You've decided to sacrifice Yep. You've decided to be part of the job creation mechanism. , there are wins than just having some big exit. Yeah. Whatever happens. And nobody's gonna look at you and say, wow, you are an entrepreneur, but it didn't work out.

Nobody's, and remind yourself of that. And that's where you do have to say, yes, I'm willing to give it all for this company, but I'm gonna keep myself separate because. Because it's not the be all and end all.

Angela Gennari: Yeah, absolutely. So what do you I really enjoyed this conversation, Brittany, and you were just absolutely freaking brilliant.

And I could probably talk with you all [00:51:00] day. I know. I wish we'd been in California at the same time. I know. Ships passing in the night. I wish we could have connected in LA, but yeah, so you're brilliant. And I Definitely want to chat more at some other point. We're going to find ourselves in the same city at some point.

But what do you wish more people knew about founding, about anything that you think I would say

Brittany Greenfield: I wish more people. And again, this is a do as I say, not as I do. I wish people knew it's just life, right? And go, you've got to go do the things that make you happy. And it's, nothing's so serious that you can't overcome it. All of those things it's going to be okay. And I have to tell myself that sometimes.

Angela Gennari: A lot of times. Talk yourself off the cliff. Talk yourself [00:52:00] off the cliff. I know.

Brittany Greenfield: It's going to be okay. It's going to be okay. Millions of years of people have survived in much worse things, right? Much harder things. And it's going to be okay. And, if you focus on the good things out there. Things will come to you.

And I'm not, I don't sit around talking about this a lot, but it's true, right? Like when you, it's why I've learned to talk about, not just the sacrifice, but making sure that you take time for yourself. Cause if you're also in that negative loop, you're not going to be open to the good things coming in.

You can't absorb. And I said a year ago, I'm tired of being angry, right? Like I'd had some bad experiences. So I'm just, I'm tired of being angry. It's just time to move on. And right, because it had been so much of that negative loop. And it was shortly after SVB. Officially, I cannot control what is going on.

That's right, exactly. And an investor that was supposed to write us a million and [00:53:00] change check that we disappeared. Yikes. And I can't control that. What goes officially to that? You, I want to feel the good back in my life and it's not always going to come from work. And, remember it's going to be okay.

It's all good. And take time for the things that are good for you, whatever that is. That could be cooking. That could be reading. That could be your family. Whatever it is, just make sure you make that time and it's all going to be okay.

Angela Gennari: Yeah, it will. It will all be okay. And, I love that you said, don't get stuck in the negative loop because, I was actually one of the Lyft drivers.

I've taken like 20 lifts in the past.

So we one of the guys was like, he was talking about he was talking about driving and he was saying that, somebody was looking at him and he was on a motorcycle and they were looking at him and not intentionally were driving right at him because they were looking at him. He's whatever you're focused on, whatever you're looking at, you go towards.

And I'm like, that is just such a great, kind of

Both: thing.

Angela Gennari: Life advice, right? Whatever you're focused on, [00:54:00] that's where you're heading. So focus on good things. Cause correct.

Brittany Greenfield: Exactly. And just have a drumbeat because the, I actually always use more of the analogy of a boat, because the tides will change, the waves will change, and this is true also for an organization.

Just make sure you know what that rhythm is, so you're rowing consistently towards the same thing, even if the tides, the winds, the whatever change. You're at least all doing it together or just you're doing it for yourself and aligning the resources around you to do it in your boat. So you'll get there.

You'll get there. Just keep an eye on it. It's there somewhere. There's

Angela Gennari: somewhere. And one last really quick thing. Cause you brought up the whole thing with the rowing and the boat. So I belong to this organization called conscious capitalism. And I we actually had a discussion about a week ago and I brought my whole management team and it was just very timely because my management team is all new in their markets.

And so we're in seven different states right now and we're having a hard time finding [00:55:00] alignment, right? So finding alignment. And so in this conscious capitalism event the lady who was leading the instruction was saying that she read a book called the boys in the boat. And it's about the 19th.

And the movie

Brittany Greenfield: is great too. Yes!

Angela Gennari: So she said the thing that stuck out to her the most was when they were all struggling and this is like the 1936 Olympics or something. And so when they were all struggling to find their rhythm and rowing because rowing is All about rhythm, right? It's all about consistency.

And you had some people who are really strong and some people who are not as strong. And she said, until you want to see the other people on the boat, win as much as you want to see you win, find your rhythm together. And so that has, I sent the boys in the boat book to every one of my managers.

It's

Brittany Greenfield: so funny. I was actually given that book years ago by the president of a board I was sitting on. And I went. And I went, why is she giving us this book? And and I admittedly didn't read it for a year or so. And I finally went [00:56:00] what does this have to do with anything? She didn't do a good job.

She was very, I just read this book. It's great, whatever. And she forgot, she didn't bring the lesson to the table. And then I sat down and I read it and I've used that analogy all the time. And when they get their rhythm and they care about helping the person in front of them and behind them, then they, that's when they start winning.

And that's, it is a rhythm together, even as things may change. And yeah highly recommend it. Very powerful business book. Yeah, because

Angela Gennari: Collective effort where you are unified becomes more powerful than the individual parts. Correct. And so that's really what you're focused on.

Brittany Greenfield: And it doesn't matter if you have a ton of a ton of energy. If you're not all on the same rhythm. I always talk about this in a mission vision conversation.

Both: If

Brittany Greenfield: you're not all paddling the same direction. That's literally chaos, right? And so it doesn't matter how well intentioned everybody is, if you guys [00:57:00] aren't aligned on your efforts and your vision and where you're going, you're never going to get there because one row will counterbalance another one or out Cancel out another one.

Angela Gennari: Absolutely. And sorry, my dogs just went bananas.

Brittany Greenfield: If I was at home, you would have seen a dog up here.

Angela Gennari: So much, Brittany. This has just been an unbelievable conversation. I've really enjoyed it. You are so brilliant. And I just can't wait to see what you do. So thank

Brittany Greenfield: you, Angela. I appreciate you bringing stories out to your audience and look forward to having a glass of wine sometime.

Absolutely.

Angela Gennari: It will happen. All right. Thank you so much again. And I hope everyone has an amazing day. Please check out Brittany. You will find Brittany Greenfield on prettypowerfulpodcast. com. And where else can they find you?

Brittany Greenfield: They can find information about me at brittanygreenfield. com or on LinkedIn, please.

If you reach out to me on LinkedIn, just let me know that you heard me on pretty powerful podcast. And I'm happy to carry on any of these conversations and more with you.

Angela Gennari: Perfect. Thank you so very [00:58:00] much. And I look forward to seeing what else you're doing. All right, everybody have a great day and we will connect later next week.

Thanks so

Intro: much. for joining our guests on the pretty powerful podcast. And we hope you've gained new insight and learn from exceptional women. Remember to subscribe or check out this and all episodes on pretty powerful podcast. com. Visit us next time. And until then step into your own power.