Career Growth Advice from Anneka Gupta, Data Security Leader | Career Tips for Women in Data Security

2B Bolder Podcast – Episode 105
Featuring Anneka Gupta, CPO at Rubrik

Episode Title: #105 Anneka Gupta, the Chief Product Officer at Rubrik takes a transparent look at being a woman in tech

Host: Mary Killelea
Guest: Anneka Gupta



Mary Killelea (Host): Hi there. My name is Mary Killelea. Welcome to the To Be Bolder podcast, providing career insights for the next generation of women in business and tech. To Be Bolder was created out of my love for technology and marketing, my desire to bring together like-minded women, and my hope to be a great role model and source of inspiration for my two girls and other young women like you. Encouraging you guys to show up and to be bolder and to know that anything you guys dream of, it's totally possible. So, sit back, relax and enjoy the conversation.

Hi there. Today it is my great pleasure to have on the show Anneka Gupta. Anika is the chief product officer at Rubrik, the zero trust data security company. Her career spans more than a decade in product and SaaS domain. Anika's journey is totally inspiring with a proven track record of driving revenue growth, navigating expansions to new markets, and overseeing critical diversity, inclusion and belonging initiatives.

Before joining Rubrik, Anneka made significant strides at LiveRamp, where she served as the president and head of product and platforms, leading product development and go to market operations and strategy. Her leadership extends beyond her immediate professional responsibilities, as she also is on the board of directors at Tenuity, contributing her expertise to further their Anika has been named one of the most influential women in business by the San Francisco Business Times in 2021 and a recipient of the Rising Stars Leadership Under 40 Award at the Ad Exchanger Awards in 2020. Among many other awards, it is so exciting to have her here. Her story is a testament to what is possible when talent meets determination, making her an inspiration to women everywhere. Anika, thank you so much for being here.

Anneka Gupta (Guest): Thank you so much for having me. It's a pleasure to meet you.

Mary Killelea: And I know everyone can't see it, but you have just the most amazing podcast audio setup so far of all my guests.

Anneka Gupta: I wish I could take credit for that.

Mary Killelea: Okay, so your career directory is incredible. It's super inspiring. Initially, you drew what drew you in to tech and the SaaS industry. Tell us about how you got your start.

Anneka Gupta: Yeah, so I was born and raised in the Bay Area. Both of my parents immigrated to the US from India for grad school. They were both engineers. They ended up starting their own companies and running their own companies and taking their own companies public. So, I like to say the entrepreneurship is in my blood and technology is in my blood. They really got to see the evolution of Silicon Valley from the very start. And I've heard a lot of their stories, and I lived it as well throughout my childhood and my lifetime living in the Bay Area.

So I think that naturally gave me this interest in technology, in the potential of technology and the rapid innovation of it. And when I graduated from college, it was an obvious choice for me to say, hey, let me go work at a startup. Let me get into technology. Let me see how I can make a very large impact like my parents did.

Mary Killelea: That's awesome. And I can see how that was so influential. So, tell us about your current role and responsibilities at Rubrik.

Anneka Gupta: Yeah, so Rubrik is a data security company. What we do is traditional security has really focused around keeping attackers out of a company's system or organization's data. But the reality is, is that cyber-attacks are becoming more frequent, more common, more impactful. I feel like every week in the news, we're hearing about another significant attack on a very important organization. And the reality is, is that while organizations have made all of these investments in keeping intruders out of their system, attackers are still getting through to the data.

At Rubrik, we focus on cyber resilience. We focus on what happens after attackers get in. How do we minimize the blast radius and the impact to the organization? How do we minimize the downtime and ensure that organizations can recover seamlessly with minimal downtime when they get hit with cyber-attacks? My role at Rubrik as Chief Product Officer is to really usher the product strategy and product roadmap. So really thinking about and working with our customers to understand what are the problems they're facing? What can we uniquely solve for? How do we figure out where we're putting our investments? Because there's so much opportunity out there. There's so many things that we could do figuring out, like, where do we place our chips? Where do we make our bets? And how do we take our customers along with us on that journey?

Mary Killelea: I've had a few guests on here in the security space, and all of them have said that the security space is a great field and opportunity for women. Do you find it balanced, men and women in the space? Or do you see it as a great opportunity for women who are pivoting, transitioning, looking at training to start something new? I think security, since it's somewhat new, in the sense that everybody has so much data now, and they're trying to catch up on how to keep it secure, that there is an opportunity. I love your point of view on that.

Anneka Gupta: Yes, it's certainly not balanced today. There are far too few women in security, in IT, then what I think we need, honestly, especially because I think the diversity of perspectives can help us in cyber defense so much. And that's really what's needed. So, I think it's a huge opportunity. I think women should absolutely look into the field. It's rapidly changing. Yes, there are people that are experts. But the reality is, is that most organizations as they're looking to expand their cybersecurity teams have to look outside the experts because the landscape is changing so quickly. And frankly, there just aren't enough trained experts. So, most cybersecurity leaders that I talk to, they're talking about how do I train my workforce? How do I bring people in and grow them? And that's a huge opportunity because you don't have to be an expert coming in. There is a ton of opportunity. There's a ton of growth potential.

There's a lot of really interesting and challenging problems. It's very highly intellectually interesting and exciting because of the pace of change and the pace of innovation. And it's really meaningful. I know like a lot of women look for work that really has an impact. And you know, like you can see the impact, the customers that we're working with, we are saving them from potentially catastrophic organ catastrophic failures. We are helping organizations that serve vital services to people in our country across the world stay up and running so that they can continue to provide those services. It's highly impactful, highly meaningful work as well.

Mary Killelea: I love that you point out that security is meaningful work. And one, there's training and two, there's so much opportunity. And one thing that we were talking about when it first started was every job, whether or not you think of it as a tech job or not, the way the world is changing and evolving with innovation, we are all kind of going towards a tech career. What advice do you have? Or I guess, how can you help agree with that statement? Like, I think some people hesitate to get into tech because they think they need to have such training. And yet I think there's such a big opportunity that women need to understand they don't have to come in with all the chops or that they can't get trained. So I want to talk about that for a minute.

Anneka Gupta: Yeah, I think it's a great observation. And there's all this data out there that say, you know, women will only apply to a job if they meet 100% of the qualifications, while men will apply to the job if they only meet a small percentage of the qualifications, right? So, I think that does inhibit women sometimes from engaging in these fields that are maybe different than where they've traditionally had experiences, either in like through education or in their work experience.

What I would say is that the world is changing so fast, not just in our field, but across the board, that I think the most valuable skill, maybe the biggest piece of advice that I would give to people is that the thing to hone is learning how to learn. If you can learn how to learn, and you can lean into the fact and have confidence that whatever situation you are put into, you will figure it out. I think that mentality and building that skill ultimately can give women the confidence that they can jump into a new field, a new industry, a new company with more ease, not just women, anyone. And I think that's played a really major role in how I think about my own development and careers.

Before, you talked a little bit about my bio, before Rubric, I was in a marketing technology company. I wasn't in the world of IT or security at all. I had some adjacent focuses to it, and I was in the world of data, so I knew that. But I came into a very technical product where I had very few interactions with the CIO before, with the CSO before, and all of a sudden I'm building products for these personas. It was a lot of learning. And what got me through the first six months as I was finding my path and my way was really leaning into the fact that, okay, I know how to learn. I've picked up so many new skills so quickly. I've jumped into new jobs so many times before. Let me apply that framework and that thinking the way that I went to any problem to this new opportunity and new job.

Mary Killelea: That's fantastic and such an important point for our audience to hear. Throughout your career, you've held leadership roles in various capacities. What has been your strategy for scaling the highly successful B2B enterprise from SaaS business across the different functions?

Anneka Gupta: I could probably talk about this topic for two hours because there's no recipe to it. I think the thing to recognize, and I think this is actually where sometimes a lot of new leaders that come into an organization fail, is that every organization, every business is different. What I tend to focus on is I'm very much like a first principles person. So, I come in and I'm like, what are we trying to do as a business? Like what matters most? What are the existential risks for our business? What are the biggest opportunities in front of us? And how do we make sure that we go solve those things as quickly as possible? And having that clarity and then bringing the stakeholders that clarity of this is what matters most and then working with them to understand why is it that we're not able to go after these opportunities? What's standing in our way? Making everyone part of solutioning that brings people along the journey and helps them stay focused on what is the outcome that we're ultimately trying to drive.

It sounds simple on paper, but it never is, right? You have to meet people where they are and understand what their day to day is and what they're facing. And I've found cross-functional collaboration, it's so much about making those connections in a meaningful way, showing empathy. And empathy is not like, oh, I just care about you. No, I understand the challenges that you're facing. I understand what I'm asking you to do is on top of the hundred things that you already have to do. But if we do this together, it's going to either make your life better on those hundred other things, or it's going to really propel the business forward. And it's worthwhile prioritizing this over everything else.

Mary Killelea: Leadership, especially in tech, requires a blend of vision and action. How do you balance innovation with operational demands in your role?

Anneka Gupta: I think I asked myself this question at least once a month. I'm like, am I spending enough time on innovation versus just doing my day to day? There are a few ways I think about it. One is that I look to my team, as I manage about 70, 75 people at this point. And am I able to get the leverage from my team to be able to then go focus on the things I uniquely am able to do? So, there's some kind of innovations that only I can drive because I have enough visibility and context around everything that we're doing across the business. What is our CEO thinking about? What is our sales team really going to be able to go execute on? Things like that. What are the other startups in the ecosystem that we could potentially acquire to accelerate this vision? So, I'm in a unique place with respect to the rest of my team where I have a lot of context that maybe allows me to go focus on those things. And those are the things I should be focusing on.

Whereas how do I make sure I structure my team such that there is focus around the initiatives and product areas, I lead product, that matter the most? And I'm a big believer that your org structure should be a reflection of your strategy. And if it's not, then your strategy will be dictated by your org structure. Where do you have leaders focusing time? And those people are going to focus time. If you make it their charter to focus on a certain area, then that's what they're going to go do and figure out. And so, in balancing that org structure and saying, okay, there's innovation that needs to be driven at each product within the portfolio at that level, then there's innovation that might be something that's totally new and outside of the purview of my team. And let me focus my attention on that.

And then of course, there's operating the day to day. And I think you can't let go of operating the day to day in the face of innovation. I think actually getting in the weeds on issues and deciding which issues to get involved in because they're important or because they're going to give you context into something in the organization that you want more context on. That's how I approach it. There are things where I'm really rolling on my sleeves and doing a bunch of work myself, but I choose strategically what those things are. And if I'm in a position where I can't choose because maybe I don't have the right person or there's literally no one in that role, then that gives me an opportunity to do the work and then figure out, okay, how do I then offload this to someone else? And again, solve that through the org structure and the leverage I can create there.

Mary Killelea: You're known for prioritizing diversity, inclusion and belonging as part of business culture. Explain your passion behind this. I think it started with, for so many years now, I have been the most senior woman in the organizations that I've been at. And I look around the room and I don't see a lot of people like me. And that doesn't bother me per se, but I see that as an opportunity to say, hey, how can I, given that I'm in a leadership position, how can I change the game? How can I use the fact that I have power in an organization to change the nature of the experiences that other women are having and make systematic changes if those need to be made or systemic changes if those need to be made or even make small changes if those are what's going to move the needle the most.

So, I guess that's where I originally came from. And then as I've gotten more engaged, as I've mentored more people formally and informally, gotten involved in more organizations, I think I've met so many amazing people that are furthering DEI initiatives and are doing such impactful work. But that also gives me energy to say, okay, let me carve out a little bit more time to focus on this and prioritize it.

Mary Killelea: Well, that's amazing, because we need more women who are in those senior roles to do exactly what you're doing to open up those doors. So, kudos to you for doing that. On this show, I'm certainly trying to help career women overcome struggles that they have and confidence and overcoming self-doubt is something that's kind of consistent that we hear from a lot of our listeners. How have you managed these feelings throughout your career? You seem very confident, and I know having the background that you do and the role models that you had that there was, I guess, support in place. But for those who don't have that support or don't have those role models, what advice do you have for overcoming the self-doubt and building that confidence?

Anneka Gupta: It's a great question. And it's something that I coach a lot of people on, whether it's on my team or otherwise. And it's a challenge that even though I've had these amazing role models, I've certainly felt it many, many times before, where I come into a situation and I'm doubting am I adding enough value? Do the people around me respect me? I think there was something that happened, I think, in my previous job, in my previous role at LiveRamp, and I was there for a very long time. So, I went through many different kinds of career transitions there, where our company got acquired by a much larger and older company with a very, very different culture than ours. And I remember being in the room with all these people that had 35 years more work experience than me. And they were all looking at me and the rest of our team being like, okay, you're coming in here, you're probably going to take all our jobs. It was a very emotionally charged situation. And I was able to build these deep, meaningful connections with people. And in that process, it gave me an appreciation that everyone has something to teach and everyone has something to learn. And when I was able to embrace the fact that even though I was younger than everyone, I still had something to bring to the table and give. And I also had something to learn. It's not like an ego thing. I'm like, I can also learn from all kinds of different people. And there's some nugget there that there's something I can learn from them. When I embraced that, it really changed my perspective.

Now, I think every time I quote someone on this, I'm like, everything I say is it's always easier said than done. It's always easier to say, hey, feel all the emotions, but try to leave them behind when then you actually have to act and do things that get you out of your comfort zone, find your safe environment, try on a different hat. That's another thing I tell people is, again, I've done this because someone gave me this advice where choose once you've established trust within an organization, you can choose to adopt a different personality in a particular context. So, if you see someone on the team, you're like, oh, this person is really assertive. Adopt that personality for a day or for a particular meeting and see how it works out. And it's taking a chance at taking a risk because you're doing something that you're not comfortable with, you're acting with it, you typically wouldn't. But if you're in a place where you've already established a trust, you can afford to take that risk because you're not going to get fired for in one meeting being a little more assertive.

So, there's things like that. There's tips and tricks and things that have really resonated with me. And those aren't necessarily going to resonate with every single person in every situation. But some of those things have actually just really helped me get over those moments. And then I still feel at times that everyone feels it at times that I'm like, oh, I'm in over my head. I don't know what I'm doing. I have self confidence issues. But it practice and just going through this many times makes me realize, okay, I'm going to feel this, you know, let myself feel this for two days. And then I'm going to move on and keep moving forward and not let that feeling change the way I actually show up.

Mary Killelea: I love that. I want to talk about the different types of business as women look to either pivot, like I said before, or just entering into a career path. There's SaaS companies, which I would love for you just to even define that talk about that. And then also like more of a traditional enterprise. And then what's the comparison between like the startup environment versus the non-startup environment, and kind of the personality traits that I think resonate better in certain environments?

Anneka Gupta: Yep.

Mary Killelea: If you know what I mean?

Anneka Gupta: Yeah. Okay, that's a great question. So yeah, I you know, it's interesting, you talked about SaaS versus BB enterprise, I actually have stopped really think like talking about companies with SaaS companies and really said, okay, there's B2C. And then there's, you know, B2B. And then there's B2B enterprise. And B2B enterprise, in my mind is any sort of technology that's being sold to large organizations, this isn't about just like, you know, small organizations or something that's very specific to a particular vertical, like, you know, a specific real estate technology or something like that. I'm talking about like B2B enterprise or something that is multi vertical, like some kind of solution, and typically gets sold into larger enterprises.

So that's that's how I would define it. I think there are different personality traits, as you say, or different strengths that I think are required in an earlier stage versus later stage startup, and then more mature companies. And I've seen like, in my career, I've actually had the opportunity to see all of those. And it's very, it's been very interesting.

So, starting with startups, like I think in startups, the name of the game is like, you've got to move fast, and make decisions quickly, even without a lot of data and information. And you're going to be reacting quickly, you're going to your priorities are going to be shifting. But it's all about like, hey, how do you test and learn test and learn super quickly to figure out where are you going to get product market fit. And you may make wild swings in the strategy or products because you start one place and then you end somewhere or somewhere totally different. And I think that scrappiness that ability to make a decision that's well informed, but you're not taking tons of time and don't need tons of data to make it like off of one or two conversations, you're making decisions and moving quickly. That's gonna and you're willing to wear many hats as well that you're not locked into saying, hey, my role is just a to B is like, no, I'm going to do everything that it takes to get this done. So that's the kind of like, personality trait, that's the kind of set of skills that I think what someone needs to flourish in an early stage.

When you start talking about companies scaling, and really not no longer early stage, but like, like Rubric, we're high growth, but scaling really quickly, then it goes from kind of that what I call like the maverick personality, like you still want a little bit of that, because you're not your goal is not to just like, be a be a servant to the process, but rather, you have to design the process, you have to design a way to continue to be entrepreneurial, but also scale out and cross functionally collaborate. And if you just have like 1,000 mavericks within your company, like you're actually going to be slower than if you can actually harness some of the like harness people in a more constructive direction. But it's a lot about like designing the right process, knowing when to break that process, knowing when to redesign the process, and still being like very focused on like roll up your sleeves, you're not just designing a system, you actually have to like go and do the work as well. So it's kind of that.

And then I think once you get into a more mature company, it's a lot more focused on data, it's a lot more focused on being really thoughtful, there's more typically more risk aversion, unless you're in some like super innovative group. And even a small decision can have very large impact on your business and on your customers. But that it may feel like a very small improvement. I think that that's just a very different kind of skill set, different kind of rhythm way of operating. And I would say different people I know find energy, more energy in these different stages than others.

Mary Killelea: That was so well put. And that's something that I haven't ever talked about on different on any of the other shows. So I love that you covered that. And success can be defined in many ways. How do you define success, both in your career and personally?

Anneka Gupta: I think that definition has definitely changed throughout my career, because earlier on, I was very much looking at like the next job of like, how can I increase my impact, my scope, how can I get that bigger title. And once I got into the C suite, I think there was less about how do I get the bigger title. And that was like a big change. I was like, well, what do I what do I think about for myself now? And it's not so clear. What do I do next? And what does success look like for me?

I think now I anchor a lot of my success, both personally and professionally, on the personal satisfaction that I'm getting from how I spend my time. And that really changed, I have a 21 month age, and I'm very simple. So, I think after I had my son, that was very clear to me, I was like, okay, I have this other thing outside of work now, not that my husband wasn't someone I wanted to spend a lot of time with, I did. But it was this other thing outside of work that's so meaningful to me, that I could be spending so like as much time on as I spend at work. And I think what it started to make me realize is like, I love my work. And I love the time that I spend at home. I'm really lucky that that's the case. But if as long as I feel that, as long as I feel excited about what I'm doing, how I'm spending my time, the impact that I'm having, both at home, and in the workplace, then to me, that's success at this point. It's, it's, it's feeling that as soon as I get this feeling of like, oh, I don't feel like what I'm doing is worthwhile. And I don't like the way I'm spending my time, I think that that will motivate me to change something in my life to do something different.
Mary Killelea: That's advice we all should take. And what would you say is your superpower?

Anneka Gupta: My superpower is taking things that are very complex and being able to synthesize them and simplify them. I'm really drawn to complexity, whether it's complexity in products, complexity and customer challenges, complexity and operations. I find complex problems very, very interesting, which is why I've been drawn to actually larger and larger scale companies, as opposed to going back to an early stage, because the complexity of the number of signals you're getting and trying to distill that and trying to help the team make sense of that, it gets bigger, the like the bigger the product is, and the more customers you have. And I found that that to be very fulfilling, because I think that is what I really excel at.

Mary Killelea: Have you had a career path since you I mean, not I don't mean career path, a strategy that you knew where you wanted to get, and that you were going to take this route, that route, that route to get there? Or talk to me about your journey as far as strategic approach to it.

Anneka Gupta: I didn't, I definitely did not. I, when I graduated from college, I wanted to go to a startup company, because I didn't know what I wanted to do exactly. And I wanted to get more visibility into what all functions did in the company. And I started in software engineering, because I had enough of a background that I was able to go into that. And it was easier to get an entry level role in software engineering than in some other function within a business. And so that was that was my entry point, but I was super interested in what other people were doing in the organization.

Over time, I found myself gravitating towards product and gravitating towards this intersection of what's the technology we're building and what are the customer problems we're solving? And how do we take those? How do we take that to market? All of that was very interesting to me. And so I think I naturally started gravitating towards that. And then I started getting into more leadership positions. And at LiveRamp, I took on a lot of other functions beyond product management over the years. And it was just that those were all new experiences. But I kind of just let my curiosity and my interests and passions drive my career journey.

When I decided to leave LiveRamp, I was very deliberate, though, about how I thought about what was next, because I was there for 11 years, basically from like when I was a new grad out of college, all the way through like, you know, being the president of the company. And so, it was a big career change to just move on to something else. And what I decided to optimize for was diversifying my experiences. And I thought that that was going to set me up better for whatever I wanted to do in the future. And I had a lot of clarity that that's what I was focused on. But I was very open to how that would manifest. So I talked to so many different types of companies at so many different kinds of stages to really figure out. And again, I just let my like, let the process go and like, let it see how it developed and what I was really drawn to, and where I felt like it was going to be a good fit. And that brought me to Rubric.

Mary Killelea: That is so insightful. Thank you for sharing that. And, okay, so you touched on, you know, when you graduated, you went to Stanford, and you got your undergrad and post grad learning there, and, and you lecture there, what is the biggest takeaway? And what, first of all, what's it like to teach at the school where you went to? And then what is the biggest takeaway that you try to have your students get?

Anneka Gupta: So, I started engaging at the business school at Stanford, I didn't go to the business school, I went to undergrad at Stanford, I did some other, other programs through the business school, but didn't do an official MBA. But I started teaching or engaging in classes as part of the business school, probably six or seven years ago now, as one of the lecturers, there was building a product management class, and one was looking for guest speakers and case studies. So, I had the opportunity to start participating in that. And that was really interesting.

Then about four, three or four years ago, I actually engaged with a professor who was trying to develop a new kind of product management class that was an experiential learning class, and he wanted to co-teach it with a practitioner and co-design the class with a practitioner. And so, I had this amazing opportunity to work with him on designing this, this product management class for MBA students at Stanford. I think like all these experiences, what's been most interesting has been, first of all, just seeing over seven years, how students understanding of what product management is, has changed, because product management is still a fairly nascent field. And now students are like, what come in, have a way better understanding, many of them have interned in product management, maybe they worked in product management before business school, where that wasn't the case before. So, it's really amazing to kind of be able to see that in the academic setting.

I think the impact that it's had on me is in order to teach something, you have to know it very well. And thinking about how to communicate the concepts of product management to students has made me a better, I think it's made me a better leader, honestly, in my job. And then the thing I try to impart to them, specifically for product management, is that they're always looking for the formula. What's the formula for how I do customer interviews? What's the formula for how I decide what to prioritize? And my message to them is there is no formula. There are things that you can think about, things to consider, but everything is dependent on your organization, your product, and helping them realize that I'm giving them skills and tools, but they have to assemble those tools in a way that makes sense for the job that they're in. And they don't always love that answer from me, honestly, because they're like, there's got to be an answer, right? There's got to be a way to get that A, right? And I'm like, well, the answer is you've got to be adaptive. You've got to figure it out. And there are a lot of tips and tricks and tools and ways to handle these situations that you can rely on, but there's not one way to do things. And that's typically what I want them to leave the class understanding is that you have to be adaptive and you have to be comfortable with ambiguity because that's what this job is all about.

Mary Killelea: I love that. And I love to talk about the importance, shifting gears a little bit to personal brand and how it's an opportunity for us as women or anyone to write their own narrative and really put themselves out there and attract others by what they're putting out there. Any advice on building a personal brand?

Anneka Gupta: Yes. I think the first time someone suggested that I needed to build a personal brand, I had an almost like allergic reaction to that because I was like, oh, like, I don't want to be out there like talking about myself and doing all these things that don't feel real to me. And so, it was a struggle at first for me to figure out what does that mean for me? I think what I've leaned on is it's got to be authentic. It's got to feel like something that's natural. What works for someone else, like someone might start a blog, may not work for you. And someone might focus on speaking stuff, someone might focus on social media. There's a lot of different things that one can do to build your personal brand and get yourself out there. But whatever it is that you decide to focus on, don't do it for the reason of building a personal brand per se. Do it because it feels authentic and you get joy from it. And for me, it's like, I love connecting with people. I love mentoring people. And that's what I've gravitated towards.

That's how I ended up gravitating towards teaching as well. And just making myself open to those opportunities, making time for those, that over the course of four or five, six years has really developed into a lot of extracurricular activities that I do outside of work that have the side benefit of building my personal brand. But they feel super authentic to me. And I've tried various things. There are things that I've tried to build my personal brand and I'll experiment with some stuff. And if it doesn't feel authentic to me, I'm not going to keep it up, then I'm not going to keep it up. But it's, I have found that to me, it really comes down to like, I get so much value out of helping people that if I just focus on that and then the personal brand piece will come with it over time, if that's what I anchor on and make time for outside of day-to-day work. I think the important thing is you do have to carve out the time outside of your day-to-day work.

Mary Killelea: Yeah, I agree with you on that. What would you tell your 20-year-old self?

Anneka Gupta: Probably be patient. Even though I never had a specific career path in mind, I've always been like very ambitious and anxious about what's next and what am I doing and am I growing fast enough and am I having enough impact. And now I feel like I've kind of grown into patience and I truly feel it and I embody it. But it took me a long time to get there. And I would say there were times in my 20s especially where I was incredibly stressed out by my job to the point where I was up for like four hours in the middle of the night, four nights a week, and I was just like not eating well. And I was doing all these things that were really taking a physical and mental toll on me. And it was because I was just so stressed about stuff that I didn't necessarily need to stress out to that level about. And a lot of it came down to patience.

Over time, I figured out how to manage myself better and not get to that state as often. I mean, it's never perfect. But I think having patience and recognizing that not every problem needs to be solved today. And it's also important to manage your own energy levels such that you could be on your career marathon and you're not constantly sprinting and burning out, sprinting and burning out.

Mary Killelea: What does to be bolder mean to you?

Anneka Gupta: To be bolder really means acting even in the face of fear. I think as women, you know, sometimes we see these phrases be bold and it's like, oh, does that mean that I'm not supposed to be afraid of what's going to happen if I take this action? But the reality is, is that there's always that fear and courage and being bold is about acting in the face of that fear as opposed to in the absence of it.

Mary Killelea:I love that. Okay, before I let you go, I've got to do a fast round. Okay, you're ready?

Anneka Gupta: Yes.

Mary Killelea: Coffee or tea?

Anneka Gupta: Coffee in the morning, tea in the afternoon.

Mary Killelea: Summer or winter?

Anneka Gupta: Summer, for sure.

Mary Killelea: Pizza or pasta?

Anneka Gupta: It's a hard one. Probably pasta.

Mary Killelea: Beach or mountains?

Anneka Gupta: Both.

Mary Killelea: Dogs or cats?

Anneka Gupta: Dogs.

Mary Killelea: That's it. We have flown through this and I can't thank you enough. You taught me a lot and I love your story and I appreciate you coming on and sharing your career story with everyone here.

AG: Thanks so much for having me. This was really, really fun.

Mary Killelea: Thanks for listening to the episode today. It was really fun chatting with my guest. If you liked our show, please like it and share it with your friends. If you want to learn what we're up to, please go check out our website at 2bbolder.com. That's the number two, little b, bolder.com.