Developing an Entrepreneurial Mindset with Shama (Keskar) Butala (Podcast & Transcript)
“Either you fail or you succeed when you take a risk. I believe that even if you fail, learn to embrace the failure because look at those as an opportunity. That's going to help you build resilience.” - Shama Keskar
Shama Keskar is a CTO, Founder, and mentor with experience leading engineering teams at Amazon, Google, and LinkedIn. Her background in nuclear physics and education gives her a unique perspective and a keen interest in exploring the power and potential of big data and analytics.
In this episode we discuss:
Shama's principles of leadership
How to turn a "work/life balance" break into a benefit for your career
Lessons learned during her journey as a cofounder
Determining which side hustles are worth pursuing
Learning from a failed startup experience
Strategies for scaling
Transcript has been edited for clarity.
Karen Ko: Hey there. Welcome to Engineer Your Career, a podcast brought to you by WEST, a learning community empowering women technologists through mentorship. Join us as we hear from inspiring women tech leaders who are challenging stereotypes and paving the way for future generations. We hope their career journeys inspire you with new ideas to engineer your career. Let's get started.
Hey, everybody. Welcome to our latest episode of Engineer Your Career. I'm Karen.
Heidi Williams: And I'm Heidi.
Karen: And we're excited to introduce our speaker, Shama Keskar, a seasoned technology leader and a successful entrepreneur. She's currently an advisory CTO for Venture Studio and founder's mentor at OneDay. Welcome to the podcast!
Shama Keskar: Thank you so much, Karen and Heidi. Nice to meet you. Hello, everyone.
Karen: I had the pleasure of meeting Shama recently when she signed up to be a WEST Mentor. I really loved hearing about her story, and that's why we're thrilled to have her on the podcast today.
Heidi: Well, I have not had the chance to hear your story yet, but I am so excited to meet you, Shama. Tell me a little bit, how did you first get into programming? What did you want to be when you grew up?
Shama: While growing up in a conservative society, I had seen my parents growing all odds and working hard to provide their girls with the best education. That taught me the importance of perseverance, as well as its transformative impact of breaking the barriers.
This instilled a can-do attitude, and I believe that teaching is a noble profession that plays a crucial role in shaping individuals as well as the society as a whole. I had seen my mother as a successful teacher professor. Her students remember her even today. Being my role model, I had always a dream of becoming a professor, especially with physics, because I graduated in physics and education, and I love nuclear physics.
However, destiny had something else. As part of my first marriage, I came to the United States, and then I was asked to pursue a career in computer science. So I had joined a community college where I learned the fundamentals of Comp Science, and that's how I started getting more into programming. I got the opportunity to do an internship with Sun Microsystems back in 2003 or 2004, and that's how I learned everything about web development, and that was my first introduction to basic programming.
Heidi: That's super exciting. I have to say, I feel like I wanted to be a teacher growing up as well, and as an engineering leader, I always joke about how even as an engineering leader you still get to do teaching of the folks that are in your team and whatnot, and so hopefully you're able to scratch that itch as an engineering leader, as well. So maybe tell me a little bit what has been a highlight of your career so far?
Shama: I'll take one of the examples from LinkedIn where LinkedIn wanted to completely transition from their legacy application to a modernized mobile application. Strict timelines, very lean team, LinkedIn was growing, so definitely launching it as a mobile application with 99% quality is by far my career highlight.
I was able to leverage, learn, and apply some of the key leadership principles that I personally believe in. One of them is customer obsession or disagree and commit, buys for action or even on trust. So basically, this opportunity gave me a way to work directly with the customer, learn everything about the customer, and think beyond your customer.
A lot of things were undertaken in terms of innovation, pioneering, whether it's processes, frameworks, tools, architecture, a lot of things that were undertaken by the entire organization, including me. Just before the release, there was a fun incident that occurred.
One of our product executives, who is one of my role models, he ended up finding a search-crashing issue. It was late in the night, and the team came together at wee hours, and we resolved that issue with collaboration and going above and beyond, and that taught me the importance of collaboration, how a team can come together and solve any type of challenges.
So I learned a lot of things throughout that overall journey. I learned about quick decisioning, thinking beyond customers, working directly with C-suite leaders, how do they communicate, how do they operate, and execute, and then build that entrepreneurial spirit that helped me throughout my career.
Heidi:
It's so interesting. I feel like very often when folks share their highlight, it's often with a piece of adversity in it where there was some particular challenge, the team had to come together and sort of overcome something or ran into some obstacle. So really interesting that that ended up being your highlight of achieving something, but especially in the face of some sort of challenge along the way. So thank you for sharing that.
Karen: So in our prep call, you had also shared that as you've been moving throughout your long career in tech that you've been developing your tolerance for risk, and I'm curious if you could share a little bit more about that.
Shama: Yes, I remember departing FAANG companies when both my career and company were flourishing, for family situations. When my father-in-law or my mother-in-law were on their deathbed, my husband, my family became top priority, and without even a second thought, I decided that family comes first, and I left my roles because that was an unavoidable situation.
I have experienced that people speculate and speak behind your back as they don't understand or realize the gravity of the situation, but the best thing is to ignore them and then stay away from such toxic people. So in this situation, I just focus on my own career goals with a clear vision of what I want to achieve down the line.
Then I believed in self-awareness, which is more assessing what's your level or appetite for risk, and then are you there in terms of financial family support, in terms of market industry, are you at a stage that you can afford to take a risk to achieve something that you have always dreamed about?
And if the answer is yes, then yep, absolutely. So for me, whether it's at work or my entrepreneurial journey, I like to get out of my comfort zone and challenge myself with something new, something different.
One of the examples is when my in-laws needed some sort of reflexology therapy, I just learned it myself. Or I recently launched a side hustle in the food industry because of my passion for cooking. Not that I'm a great cook, but that's another example of going in an industry where I know nothing about.
Either you fail or you succeed when you take a risk. I believe that even if you fail, learn to embrace the failure because look at those as an opportunity. That's going to help you build resilience. I also have role models and mentors who I often seek advice, as I mentioned. I reach out to them, I look at how they have taken risk, how they have shaped their career. I learn from that. So this is how I've always dealt with taking risks and still making a path forward.
Karen: Amazing. Thank you so much for sharing that. I feel like that getting out of your comfort zone sometimes can be so, so hard for folks to get out of where they feel safe and move into a territory where they may not have any control over what's happening next. And I'm curious, as you've been moving through your career and especially founding your first company Nickelytics, I'm curious about what gave you the courage to be able to leave your previous role as the senior engineering manager to take on this new venture?
Shama: Yeah, I had seen some of my role models or some of my former colleagues from Google and LinkedIn, moving more into entrepreneurship, venture capital. I have always been fascinated by having my own business or having my own startup.
I grew up in a society of business-minded. I had seen my brother as I was growing up, taking huge risks and starting his own business. So that business-minded aspect has always been there with me, and that's when I was thinking about starting my own software as a service in test automation, in quality engineering.
That's when Nickelytics happened, and after diving into the advertising space, I loved the whole concept, and I decided to join. It was a huge financial career-wise and, in general, risky undertaking. There were chances of potentially failing or potentially succeeding. However, the way I had approached it is what my passion is, what my interests are, and then I had a good conversation with the family. There was a lot of family support and lot of encouragement from my role models and mentors, and that's how I became part of Nickelytics co-founding journey.
Heidi: That's amazing. You must have had to learn a lot of new things as a co-founder. What did it look like to sort of ramp up on some of those things, or what were some surprising things that you learned as a co-founder?
Shama: So in your career, you do face some situations where you have to learn and then relearn. So I would say as part of entrepreneurial journey, one of the important aspects that I learned is building trust and collaboration, and then building that resilience, especially when we were raising capital or going through the fundraising process, there were a lot of nos that we had received before getting one yes.
So you have to have that resilience, perseverance, and ability to believe in the idea or whatever you are pitching for, and that definitely helped me. The way I learned that is I have my own favorite podcast, or I do a lot of reading. Almost every day. I make sure to read something.
I follow ex-colleagues on LinkedIn or I read through a lot of blogs or newsletters. So some of these aspects actually help me learn how to do the pitch deck, how to go about in a fundraise, what are the expectations during a fundraising process, how to deal with the nos, how to deal with yes, all of these things I learned as part of that process.
I also learned whom to trust, when to trust, how to trust, and how to build that long-sustaining relationships. Who should be your best advisor, how to get your advisory team for your startup.
So some of those aspects of I would say entrepreneurship that I learned and now I'm applying those as part of my VoxAI, which is another co-founding initiative that I'm working with one of my former colleagues from Google. A lot of learnings that I inherited as part of whether spring, Seattle or Nickelytics, I'm definitely applying to VoxAI.
Karen: Heidi, I'm curious, as a co-founder yourself, does this resonate with you?
Heidi: Yes, definitely. I feel like one of the greatest skills you can learn as a founder is resilience because you do get nos and things that you try don't work, and the product you had envisioned doesn't quite resonate with customers, and you have to pivot.
And so certainly, resilience is something that you need to learn along the way, and you need to be scrappy and ready to make those changes, so definitely resonates.
So you mentioned earlier that you've taken several career breaks in your career. What helped you get back into tech, and what advice do you have for others if they're going through something similar in their lives?
Shama: I would say I have a strong work ethic, and it can be a blessing or it can be a curse. Taking breaks has never been part of my personality. I'm always willing to give it all for something that I care about or I'm passionate about. I believe in smart work and perseverance.
However, there were situations in my personal life that needed full attention. But to my surprise, career breaks could come as work-life balance, and then it's good for your mental health as well as your wellbeing and fitness. So certainly succeeding after a career break may pose challenges, but with the right approach and mindset, it's entirely achievable.
So one of them is upgrading yourself. Change is the only constant. It's crucial to stay abreast of market shifts, skill development, industry trends.
Throughout my career breaks, I have stayed proactive by continuously learning and exploring some of the side hustles or startup ventures, ensuring I remain updated with market and industry changes.
Then I always think a pause in your career can be an opportunity for you to think about what's next, what should be your next play. I take that opportunity to evaluate my skills, passion, values, and then come back.
And then the third and most important is, I always believe in myself. So, believe in yourself, focus on some of your superpowers, then some of the mistakes or some of the wins in the past, and then practice, practice, practice. Just learn to market yourself, learn to invest in yourself. So these are the things that will help you get back from your career break.
Karen: Thank you so much for sharing that, Shama. So we've heard about two kinds of resilience, as a co-founder and as someone who is taking career breaks. So I'm curious if you've seen that reflected in your leadership style and if you've seen your leadership style shift between being an entrepreneur and while being an engineering manager.
Shama: Yeah, absolutely. I would say that there was a survey article by Forbes. It concluded that women have innate leadership skills for volatile times, but they may risk becoming obsolete without embracing curiosity.
Curiosity is at the heart of whether you are an entrepreneur or you are doing your leadership. So for me, I would say that, as Brené Brown says, leadership is about having the courage to develop the potential in people and processes and being willing to stay up and lean into it.
So when I was just a regular engineering leader, I always embraced curiosity. Being curious and understanding another's perspective and being thoughtful about that was very important.
Creating a culture of inclusivity and then decision becomes part of everyone's life is very important. Another aspect, I would say that as a co-founder, definitely one of the ways to build resiliency is embracing some of the challenges as an opportunity to grow.
So embracing new ideas, perspectives, ready to pivot, especially when you know that this is not working out or based on input or feedback from your peers, from your advisors or your investors. One needs to learn, embracing and then taking this feedback and then acting upon it. That's another way to build resiliency.
That's how I have done it. I always take constructive feedback or any sort of feedback and take actions on those and learn from those, and make sure that I never repeat those mistakes again is a way that I have built resiliency for both the entrepreneurial journey as well as the leadership role that I have been laid.
Karen: Amazing. I think staying curious and how that builds into adaptability and resilience, I think is so key. I feel like when you're staying curious as well, it's also staying humble in some ways. That you're recognizing that you don't know everything there is to know about a certain thing and that there's more to learn, and approaching it with an open mind, which I love.
Heidi: Let's take a quick break to hear from our sponsor.
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Heidi: And now back to our discussion.
Karen: You mentioned earlier that you love starting side hustles and that you've been part of different entrepreneurial opportunities within your career. I'm curious to know how you decide if an idea is just an idea or if it's an idea that's worth pursuing.
Shama: Yeah, that's really a good question. So when an idea is presented or when I have the opportunity to, say, join a company or a team as co-founder, there are a couple of aspects of that journey that I look at.
One is obviously your co-founding team, which is very important. Having that perfect chemistry between the co-founder can then flourish any idea into an actual startup. So that's one definitely important factor that I look at.
When it comes to idea itself, I look at is this idea going to have a good impact on a person's life in a positive way? That's very important to me, how you impact a customer and that customer could be a B2B, B2BC, or a direct consumer. So for me, impact on customer is one that I look at.
Second is, can I resonate with that idea? One of the great examples is when I decided to join Mudita Ventures as advisory CTO, the idea that they had presented, I could resonate with that. I have had personal experience with that initiative, and that was another way to decide that, hey, this is an idea that I want to work for.
And naturally, you want to look at your skills, what you have done so far, what knowledge you're bringing, the expertise you can apply, and an opportunity to learn something new. If you believe that there are things that you have done in your career, you can easily apply to this specific idea or startup initiative. And then you also have the opportunity to learn something new through that process, through that journey, definitely you want to take a risk and then join the team. So that's how I had done it, whether it's VoxAI or an advisory CTO role or my upcoming technology leadership role.
Karen: Amazing. So I'm hearing the co-founding team being super important, looking at the impact on the customer, if you resonate with that idea, and opportunity to learn something new. Great. So harder question, have you explored an idea that failed?
Shama: [Laughter] Yeah.
Karen: How did you bounce back?
Shama: A couple of times when I was working at Google in the advertising space, which is where I started my career, there was one initiative that had come my way. Mobile was brand new during those days, and we wanted to try something in mobile advertising, but we just didn't know how to even proceed with that idea. So naturally, we didn't even pursue. We just talked about it, brainstormed it, and boom, done.
And then in 2013, I actually thought that I should do something, and that's when I launched Novena Plus, which was more as a software as a service for test engineering, test automation, quality engineering, whatever, with one of my former colleagues.
And during that process, we prepared the business plan, we started building a website, we put together all the material, everything that is needed to go in front of the angel investor or whoever help that we needed from.
We were able to even crack the industry and then get some customers too. And then we did the work for the customer, we got paid, but then we just didn't know how to scale this. We knew that this is going to work, but we didn't really understand how are we going to scale that software as a service beyond a certain geographical location. Naturally, we failed there. We couldn't really continue on that path.
So during that process, the one thing that I learned is scalability is equally important. Thinking about scalability as soon as you start thinking about your idea is equally critical because at some point, if this idea is going to flourish, you need to start thinking about how are you going to scale? How are you going to get that last customer, and how are you going to get customers that are not just your friends and family? That's really important. If you can get a customer beyond your friends and family, I think that itself gives you a lot of encouragement and motivation to continue on that path.
Karen: Amazing. Thank you so much. I also have a question about scaling. What are some strategies for scaling that has worked for you in the past?
Shama: There are three things that I usually leverage. One is being a visionary and empathetic leader. I always believe in having crystal clear vision and then sharing that vision with the team, the organization, or stakeholder peers, and getting their perspective, getting their inputs, and reshaping your overall vision is critical.
The vision is something that will help you navigate through blockers or navigate through some of the tough situations that are going on in the market. So definitely vision is one.
Then having crystal clear goals, I use OKR or GSM, which are two of my favorite frameworks. One is Google's Objective and Key Result, which I learned at Google. And another one is also Google's GSM, which is Goal, Signal, and Metric. That has helped me understand the company's mission, business goals, and create the goals for my team, my organization, or for collaborating with my partners.
So having those crystal clear goals help you structure your team in such a way that then you can have small teams that work independently, and then you just have to equip them with whatever resources they need that helps with overall scaling.
And the third thing is, naturally, your customer. Having the good customer feedback loop is very critical. Bringing customers' input at every stage of your scaling is equally critical because then you can shape some KPI, you can have some measures. So having those KPI measures will help you understand how are you scaling, what are the areas that you need to work on, what are the things that you need to revisit, do you need to revisit your overall strategy? So all of these things help.
Karen: Thank you. So scaling as an empathetic leader, having a crystal clear vision, good customer feedback, and being strategic about your decisions. I love all of those things that you just shared with us. Thank you for that.
I'm curious if you have any favorite books or resources that you'd like to recommend when it comes to entrepreneurship or being a CEO?
Shama: Yeah, absolutely. I recently read a book called Rewired. It's a McKinsey guide to outcomings in the age of digital and artificial intelligence. So definitely that one I would recommend.
Then Measuring What Matters. As I mentioned, measures or KPIs are very critical, especially if you're a leader, individual contributor, co-founder, entrepreneur, whatever it is, you need to know how you're going to measure your own success, whether the company's product, customer, your team, everything.
Then there is one more. The Manager's Path. That's very helpful, no matter what level of career you are in, whether you are just starting as a new leader, whether you are a seasoned leader. Even today, I've read it a couple of times, and I continue to read that book whenever I come across any situation.
And in general, I read a lot. There is one more book that I recently read is Zero to One. That's a good book. I have had the opportunity to take initiatives from zero to one, and that book has helped me through my career journey.
Heidi: What a great list. Thank you for sharing all of those. So maybe one last question before we wrap up. Opportunity to spotlight anything that you're excited about, anything upcoming that you'd like to share about?
Shama: Yeah, absolutely. As I mentioned, VoxAI, which is startup initiative that me and my former colleague Jesse are working on using some of the latest technologies like large language models or artificial intelligence machine learning. It's all about social behavior analysis. And that's coming towards June. That's the initial prototype.
Another aspect I will talk about is I've been part of OneDay, which is an entrepreneur-in-residence program. At OneDay, we are democratizing entrepreneurship, guiding early-stage founders to launch a business and earn an accredited MBA. So I'm part of that group as entrepreneur in residence, more of a founder's mentor. So those are the couple of things that I would share.
Heidi: Fantastic. Thank you so much. Well, congratulations and good luck with VoxAI, and thank you so much for your time and all of your insights. It's been great hearing all of your stories. Thank you, Shama.
Shama: Thank you, Heidi. Thank you, Karen.
Karen: Thank you, Shama.
And that wraps up another great episode of Engineer Your Career. Engineer Your career is produced by WEST, a learning community that empowers women technologists through mentorship.
Special thanks to our audio production team, Heidi Williams, Amanda Beaty, and yours truly, Karen Ko. If you enjoy our work, we encourage you to share this episode with a friend. Want to hear more from Engineer Your Career? Subscribe on your favorite podcasting app. We look forward to having you back for our next episode. Thanks for tuning in.
