We had the good fortune of connecting with Kelly O’Grady and we’ve shared our conversation below.
Hi Kelly, what role has risk played in your life or career?
I consider risk taking necessary to progress. If I am not taking a risk, then I am becoming complacent. I have learned that it is extremely easy to be lured in by the promise of the familiar, and the stability of following a path others perceive as impressive. There are clear markers of success and there is a comfort in knowing the steps you need to take in order to achieve your goal. Up until a few years ago, I existed squarely within that trap. I had spent my life achieving things in service of this coveted life I mapped out in my mind, without ever evaluating if I truly wanted them; an MBA from Harvard Business School, the management consulting job etc. That does not mean that I didn’t work hard or learn anything during these experiences – far from it. But I was suppressing the little voice inside that would urge me, “you’re meant for something different.” I continued to do so until it became so overwhelmingly loud that I couldn’t think or feel anything else. So despite the fear, the judgement from friends and colleagues and the complete lack of security, I took a risk and embraced my yearning to be a storyteller. Are there moments where I question myself? Undoubtedly. But do I also feel like I am on the right path towards my definition of success? Absolutely. I firmly believe not taking a risk ends up being the greatest risk of all.
Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
It was difficult to pick one category to define myself by – currently I serve as the Chief Host & Correspondent and Head of Video. In that role, I wear multiple hats, as one often does in the startup world! I serve as a storyteller, giving a face and voice to change makers in the space. I serve as on-air talent, evaluating and opining on key developments in the tech and media industries. And I also serve as the business force behind our video operation. I call myself a creative because my core focus is being that on-air storyteller. Growing up, I found countless sources of inspiration in all forms of art – in a figure skating performance, in a strong film character or in an interview from Katie Couric to name a few. Storytelling is an extremely powerful thing – it allows us as the viewers to connect and imagine ourselves in a different way. What excites me most is that I am in a career where I can uniquely provide that source of inspiration and familiarity given my blended background for others who are searching for direction and motivation. Is it easy? HA! Like most, I have faced a lot of challenges in pursuit of my goals, but two stand out as the defining lessons for me thus far. The first challenge was reconciling two very different aspects of myself. For most of my career, I have cultivated my skills in business – I received an undergraduate degree from Harvard University, and an MBA from Harvard Business School. I have worked as a management consultant for McKinsey, and served on Disney’s M&A and strategy team, working on everything from the Maker Studios deal to their direct-to-consumer efforts. But I also have an extremely creative side. I spent a year as Miss Massachusetts USA, as a TV reporter for NESN, New England’s premier sports network, and I’m a model. Finding a way to accept and celebrate that I wanted a more creative career for myself that drew from my business background was something I struggled with from day one. To believe it was possible to still be “successful” in a less stable profession and to take that leap off a cliff to really give it my all was the most agonizing challenge I have ever faced (and still face). That being said, learning to believe that I deserve a career that blends both intellectual challenge and passion, so long as I am willing to fight for it without hesitation has been the most powerful lesson. If you have ever felt like there is something you are born to do, and you are betraying a part of yourself by not doing… you know exactly what I mean. The second challenge has sadly centered on women tearing each other down. I cannot count the number of times assumptions have been made about my intelligence, my drive and my all around value as a human being – mainly by my female colleagues and acquaintances. I’ll call out the elephant in the (now virtual) room: I am a former pageant queen and there certainly exist many stereotypes around women who compete in that industry regarding their ability to contribute little more to society than what they look like. I myself was skeptical about starting down that path halfway through business school, but found that those stereotypes could not be farther from the truth. The recent surge in focus on female empowerment seems to stop short when it comes to women truly supporting women. It often feels like as a woman you can either act like a man and be respected, or embrace your femininity and be perceived a joke. What I’ve learned from this is that some people cannot see beyond one aspect of your background or what you look like and will choose to define you based on that. I can and will be both.
Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
I’m going to dream in a world where COVID is behind us so I can name all my favorite L.A. spots! First thing you have to do when you land at LAX is stop at In-N-Out. I don’t care how long the wait is, it’s worth it. One of the things I love to do during the summer is catch a movie at Cinespia in the Hollywood Forever cemetery – I always bring a picnic with wine & cheese and it is so quintessentially “L.A.” enjoying the beautiful weather and celebrating the arts. We would also have to visit Manhattan Beach Creamery for a scoop of strawberry ice cream and a walk along The Strand to enjoy the beach… I mean how can you visit L.A. and not hit up the beach? And of course, you may want to work off the ice cream, so why not do it at Runyon Canyon so you can get your IG pic at the same time? There are many reasons why not, but I personally love a daily Runyon hike for some exercise! Now, I’m a Hollywood girl at heart, so for dinner we would stop at Cleo on Vine for appetizers (of course ordering the lebaneh bread with feta and my favorite cocktail on the planet – The Vinebury), and then head over to Yamashiro in the Hills for the main course: sushi with a VIEW. There are too many spots I love to frequent for a good after-dinner cocktail and music, but some of my favorites are No Vacancy, Catch, Ysabel and Perch. Top it off with brunch at Eveleigh in WeHo and you have yourself a weekend!
The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
I would be remiss if I did not give credit to my family. I believe family is who you choose, so mine is comprised of my parents, my fiancé and my best friend. My Mom and Dad have ridden this roller coaster with me – and we’re talking Space Mountain, not some kiddie ride like the Tea Cups – with nothing but unflagging support. Their confidence in me to succeed in vastly different endeavors has empowered me to believe in myself when I didn’t see a reason to. I know I will never be able to fully convey how thankful I am for the opportunities and love they provide me. Now for my “chosen” family. Without my fiancé, Caleb, I never would have taken this risk. I would have talked about it, but I would not have had the courage to take action. He pushes me to be a better version of myself, even when I do not want to be. And finally, my best friend Laura taught me to be my own person. My very first manager, she showed me how to show up, guns blazing, ready to slay, and whether she intended it or not, she was the first person to get me to start listening to that little voice inside.
Justin Hammond, Fadil Berisha