Dolly J. Krishnaswamy of SecurityScorecard: “Watch your mentors ”

Watch your mentors — and remember that mentors can come in many different forms. When I say the word ‘mentor,’ most people jump to thinking about a boss or a teacher, someone in a position of power above them. But that’s not always the case. As a part of my series about “Grit: The Most Overlooked Ingredient of […]

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Watch your mentors — and remember that mentors can come in many different forms. When I say the word ‘mentor,’ most people jump to thinking about a boss or a teacher, someone in a position of power above them. But that’s not always the case.

As a part of my series about “Grit: The Most Overlooked Ingredient of Success” I had the pleasure of interviewing Dolly J. Krishnaswamy.

Dolly J. Krishnaswamy is the Chief of Staff at SecurityScorecard and is responsible for driving innovation projects and key strategic and operational initiatives as a member of the senior leadership team. Prior to SecurityScorecard, she was founder of Scrybersecurity, a cybersecurity consulting company focused on helping financial services clients better understand and communicate cybersecurity requirements. Previously, she worked as Global IP Strategist of a NYC-based managed service provider, helping organizations understand cybersecurity and compliance, and conduct cyber-risk assessments.

Thank you so much for doing this with us! Can you tell us a story about what events have drawn you to this specific career path

There are so many events that have led me here, but at the core, it’s been about a push to constantly grow my skills and apply them to new arenas. I’ve spent my career focused not on the pursuit of particular titles or advancement along a defined professional path but instead on continuously maximizing my learning and looking for the biggest growth opportunities. Experimentation with thousands of petri dishes, writing articles for a magazine on a rapid deadline, building websites and products, managing overseas operations for a tech company, growing and scaling teams, and all the other learning experiences in between ultimately led me here.

Can you share your story about “Grit and Success”? First can you tell us a story about the hard times that you faced when you first started your journey?

I’ve been lucky to lead a fortunate life, and have had my share of defining moments along the way, just like we all do. I remember being new to New York City, deciding literally overnight to move here. I’m a big fan of taking risks that can lead you to new experiences and adventures. The average day for a while was working three jobs and racing to make ends meet while being a couch nomad and thinking about what actually mattered to me. There’s just something about being completely exhausted at 4 a.m. that leaves you thinking about grit. Starting a small company was another time that tested me in all the best ways, but that’s a story for next time!

To talk about the first time I saw grit, it actually wasn’t my own. I’m the child of immigrant parents, and seeing their grit instilled it in me pretty early on. My father is intelligent and educated, but to support our family when I was young, he really had to start from scratch and hustle. He, like so many others at the time, had the typical “came to the States with nothing but a few dollars in my pocket and a dream” kind of story. I remember this one night as a kid, all of us staying up sorting hundreds of videos, blowing dust off the film and putting them back in their boxes. I remember my dad nodding off in the wee hours of the morning and every time he startled awake, he still had all the energy and drive of the moment he started on the tedious task. He showed me that you have to be willing to work hard and do absolutely whatever it takes — and through it all you have to be humble, and never think any job or task is beneath you. That “grit” lesson is one I’ve always carried with me.

My father became a successful entrepreneur, and taught me one thing that stands out above all others: it’s better to be lucky than smart. You can’t just rely on your intelligence. You need to keep working hard with humility, chasing opportunities, and be ready to jump when the right moment approaches.

Where did you get the drive to continue even though things were so hard?

There are three things that ground me, calm me, and drive me on the toughest days. First, tomorrow is always a new day, and no matter what happens today, the sun will set, and I will have a chance to wipe the slate clean. Tomorrow will always be a fresh start, informed by the lessons of the past and with all the promise of the future. Second, I remind myself of “diamond moments.” When a high amount of pressure is applied to a lump of carbon, it can either turn into a diamond or into dust. These high-pressure, hard scenarios that could break us are also the same ones with the capacity to make us resilient, beautiful, and brilliant. Third, I tell myself it’s going to be fine because if I’m standing here, in this moment, then that alone means it’s always been fine up to this point, and so things will have to work out in the end. I truly believe that even when you don’t have the ability to see it in the moment, if you have good intentions and work to bring positivity into the world, good things will happen. You just have to keep pushing forward.

So how did Grit lead to your eventual success? How did Grit turn things around?

I think grit is equal parts determination and flat-out courage.

Courage let me leap straight into new industries and new fields, apply what I’d learned before, and grow to be better. It helped me break from the status quo and repeatedly find shorter paths to success, more exciting opportunities to learn, and pushed me to think of the future more than the past at every turn. Determination made me keep going when things were hard, and it will keep me going when things get hard in the future.

The great thing about grit is that if life allows you to wind up with enough of it, it turns you into a person who delivers and produces impact no matter what obstacle is standing in front of you. If you are all about results, willing to roll up your sleeves and get the work done, you’ll quickly find others with the same grit running through them, and they will magically wind up in your circle. A team of people who can power through anything and deliver — well, that’s the start of something incredible, and a fast track to success.

Based on your experience, can you share 5 pieces of advice about how one can develop Grit?

  1. Keep building your skills, through success but also through fearless failure. What has helped me most in life is thinking about every career opportunity as a chance to build new skills, whether I ultimately succeed or fail. Skills are forever transferable. I became a good writer when I worked as a journalist, and I’ve taken that into every job since. I became a detail-focused wizard when I worked in cancer research, and that has served me well throughout my career. As you build these skills, have the courage to fail repeatedly. Failure will open up new opportunities and enable you to continue to learn, and the more you fail — and see that failure isn’t always a disastrous outcome, because it can lead to great next steps — the easier it is to push yourself into new and ultimately successful situations. Someone willing to learn and persist with discipline will always eventually outpace someone who is naturally gifted. If you have the capacity to learn and adjust, with no ego, you’ll end up far surpassing those who may have started out ahead.
  2. Focus your energy and time. You can’t power through a hard situation if you’re overwhelmed, or your mind is cluttered. I learned early on that you have to be diligent about your schedule, and keep yourself focused on the right tasks. I am a bit of a productivity nut. I track my time, I try to optimize every moment on my calendar — and ultimately it means I get a heck of a lot more done than I used to and know that my productivity is driving me toward clear outcomes. I put together a few tips and tricks that have helped me over the years — there’s a free excerpt here.
  3. Chase the “impossible”. Grit becomes a muscle. And the easiest way you build that muscle is by tackling the exciting, impossible problems that you want to solve. Every big leap I’ve made in my career has been about seeing something that sounded impossible, and challenging myself to address it. At the core of it, hard problems are fun, and if you’re having fun, you’re bound to succeed.
  4. Don’t let yourself get bored; create an environment where you have to stay on your toes. I’ve been described by some as a serial entrepreneur, and a collector of careers. I never want to let myself get bored, because then summoning the grit to succeed will be that much harder. We work so much harder and so much better when we’re truly fascinated by what we’re doing, learning new things, and pushing our skills to the next level. A big part of this is surrounding yourself with the best and the brightest people to keep things interesting and challenging. If you find that you’re the shiniest, smartest object in the room, change rooms or change the room.
  5. Watch your mentors — and remember that mentors can come in many different forms. When I say the word ‘mentor,’ most people jump to thinking about a boss or a teacher, someone in a position of power above them. But that’s not always the case. Inspiration, lessons, and growth can come from many different places. People more junior than you can have areas of expertise that you don’t, peers may catapult your career, or someone in a different industry might have skills that can help you grow. Learning and mentorship can come from almost any source, and being open to guidance from wherever it might emerge is incredibly important for developing grit and greater skills.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped you when things were tough? Can you share a story about that?

I could probably name a dozen people at every job who have helped me achieve success, and whose wisdom and support I’m so grateful for. I attribute so much of what I’ve been able to accomplish to the people around me, and to list all of their names would take up this entire interview. Instead, I’d say that every day at this point in my career, for almost everything I do I can point back to someone who taught me how to do it, or who made me better at doing it.

But I’m most grateful to the naysayers, to all the people who told me I couldn’t do something. The naysayers are the ones who ultimately give you the shortest path to success; they are the possessors of the most salient feedback that can drive you toward a shortcut to improving yourself and making the impossible a reality. Whenever I come across a naysayer, I try to turn that person into a positive force in my life, to drive me or to build my grit for the future. When someone says you don’t have X or you can’t Y, if you ask them why; they are your most valuable cheat sheet to how to get there even faster. When you absorb their naysaying and use it to drive you to success, you’ll find these naysayers also often turn into your biggest champions.

How have you used your success to bring goodness to the world?

I try my very best to pay it forward. Anytime anyone asks me for help, I do my best to make the time. I really do feel like if I can be a sounding board for someone, help guide them around the holes I’ve previously fallen into, or shortcut their path to success — whatever that means to them — that’s something I am strict about creating time for. It brings me a lot of joy to know that I might be able to have a positive impact on someone’s life — and so I try to do it as much as I can.

Are you working on any exciting new projects now? How do you think that will help people?

At SecurityScorecard, we recently closed our Series E round with $180 million of funding, so there is no shortage of really impactful, exciting projects! Today over five million organizations are monitored and rated by our company, over 1200+ visionary customers, and over 17,000+ engaged companies on our platform. We have been growing rapidly over the past 5 years. There is a massive future opportunity and our story is only beginning to get written. Our data centric approach to measure and communicate security will become the new standard for every company in the world. More about the funding round is in our press release here, but needless to say it’s a very exciting time for the company, and I’m thrilled to be part of it.

What advice would you give to other executives or founders to help their employees to thrive?

Understand their biggest professional passions and find ways to enable them to pursue them in alignment with your company strategic objectives.

Enable them to bring ideas to reality, and to fail fast forward.

Remind them to pause and celebrate how far they’ve come.


You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

At the end of the day, people who know me well know that I’m a really big dreamer. It’s a bit abstract, but I would love to help inspire a world where people can dream without constraint, and be able to pursue the futures they want without limitation. I think so many of us are afraid to dream big, and then for those who manage to, acting on those dreams can seem just out of reach. We get pushed back by reality and that amazing spark ends up dimmed. So I think it would be incredible to find a way to help people push boundaries on whatever they’re most passionate about and make their biggest dreams a feasible reality.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Do what lights your soul on fire”

Life can so easily pass you by — there’s so many things to do, obligations, email threads, inputs, etc. It could be so easy to just go from day to day and have time pass you by.

But — if you choose to do the things that make you wake up with your soul ablaze, passionate about what you decided to do, every moment drives you, and you find almost limitless energy. Passion and grit are such close friends; I’ve found that if you have a lot of the first, the second will naturally follow.

How can our readers follow you on social media?

Feel free to connect with me on LinkedIn: Dolly J. Krishnaswamy | LinkedIn

Thank you so much for joining us. This was very inspirational.

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