Victoria Montgomery Brown:
Digital Goddess


This is the second edition of Northern Notables, a collection of interviews with NSS Alumni who have made an impact in their personal and professional lives.

by Jason Hughes

Victoria was very involved at NSS – Secretary of SAC ’91 and SAC President in ’93. Victoria was also captain of the cross-country running team and a member of the Girls Athletic Association (GAA) for several years. After graduating from NSS, she attended McGill University and received her Master’s degree from Harvard Business School. Victoria is co-founder of Big Think, the knowledge company that makes people and companies smarter and faster through short-form video with the world’s best thinkers and doers. Since founding Big Think in 2007 and serving as it’s CEO until the company’s acquisition in late 2020, Victoria built the company from a fledging thought-leadership media platform to the leading knowledge company for ideas and soft skills, reaching 70 MM people per month.
The first in this ongoing serious is an interview with Victoria Montgomery Brown who has just published a book titled: Digital Goddess: The Unfiltered Lessons of a Female Entrepreneur. I had the opportunity to connect with Victoria and ask some questions about her first published book, life at NSS, and how to become a digital goddess.
Victoria, I was so impressed that your book uses the word “unfiltered” in the title – which is completely accurate. You share with the reader real-life issues of wardrobe calamities, earning the respect of investors and your staff from a female perspective (and even your dating history while being CEO.) What made you decide to include so many personal experiences and references to your life as part of this book and really put yourself out there?
Authenticity is critical to me. If I'm in any way endeavoring to help others, or even inspire - showing the ups and downs of what the entrepreneurial journey has been for me is what I felt should be shared. We so often hear about the enormous successes of entrepreneurs without a real reflection of what it took to get there. The sacrifices, the challenges, and the actual realities of what it takes to get a business off the ground. And, also some of the things I never expected to be a part of the story of founding and running Big Think! A lot of it is pretty funny - and in writing about it, so many memories were brought back. 
Digital Goddess – Victoria Montgomery Brown
You dedicated your book to your father. In the book, you mention him several times. Clearly, he had and continues to have an impact on your personal and career success. What roles did he play in your evolution as a Digital Goddess?
I heard someone recently mention the concept of the kitchen table MBA and it resonated. My dad was always teaching us lessons about business and the “hard truths" as he would call them of the challenges entrepreneurs face, as well as the profound meaning it can bring to a life. Creating something that contributes to others in even a very small way is valuable. Dad grew up poor in Washington State and Alaska, and through his successes showed us if we wanted something badly enough and were willing to work for it, pretty much anything professionally could be achieved. Well, within reason - some careers require gifts you can’t work for - for instance, I never had a shot of playing in the NBA. 
It’s very un-PC of me to say. We are in an unprecedented time when I don't think women necessarily DO have to work harder than men in the c-suite level or to, let’s say, get funding for a venture. It may in fact be easier.
–  Victoria Montgomery Brown
As a male reading your book, I was struck by how many of the lessons you shared also related to my experiences in leadership roles throughout my career. While I can’t relate to many of the challenges you faced as a woman, what parts of your book also relate to your male counterparts in business and life? How much harder or differently do women have to work in the C-suite level, or any level, in fact?
Digital Goddess is a book for any entrepreneur, or really any person who is or aspires to be in business.

It’s very un-PC of me to say. We are in an unprecedented time when I don't think women necessarily DO have to work harder than men in the c-suite level or to, let’s say, get funding for a venture. It may in fact be easier. Being different can work to your favor. It worked for me. Yes, I’d go into meetings with possible investors or clients and if I was with my business partner, their eyes would immediately turn to him as he’s a guy. I used it to my advantage. I was the CEO and that took them off guard. Challenging people’s expectations is an efficient way to get their attention. For sure, women must be equally talented as men in business to get to the same level - and there are some industries/careers where it is a real drawback to be a woman, but for most careers that’s not the case anymore. Being given a shot to be in a senior role at an organization or seeking venture funding may be easier for women at the moment because of the seismic shift of recognition that there need to be more women doing so. There’s a lot of making up to do. 

You are very open about the fusion of romantic relationships you’ve had in the past during your rise as Digital Goddess and your business life. You reflect upon the difference between taking risks as an entrepreneur is vital, but “risky relationships are not.” Will you explain more about keeping romance and work separate in terms of how you wrote “don’t be the CEO of your romance.”
At least for me, I’ve discovered that it’s not a good idea to mix business and romance. I brought my business self into relationships and romance is not a business, it’s about the heart and soul. Approaching a romantic relationship or partner as something or someone to be managed will likely not lead to something fulfilling for either you or the other person. I write in the book about trying harder to be softer - a romantic relationship should allow for total vulnerability - and that’s not what business is about. 
You write about the entrepreneurial drive – whether it is nature or nurture. You mention not tolerating the status quo in your career and telling people what you are going to do and then do it. What advice would give a future digital goddess to take the bold mindset even when they still have the fear of failure or not being recognized the way she should?
Just start. That’s the hardest step. Then, tell people you are doing it so that you may feel ashamed if you do not. Work shame to your advantage. If it’s only in your mind, or you that knows about it, walking away is easy. Don’t make it easy to do that. And p.s? If you fail -- you can always do something else, including another venture. 
Years ago, you wrote that your focus was usually on “quantifiable results when measuring the success of Big Think.” Now, your reflections of over two decades in your career you’ve found other ways to measure results including “the wisdom we’ve shared, the relationships we’ve formed, the minds we’ve changed, the influence we’ve had…” etc. Are you suggesting to the reader that these measurements of success you see now would have benefited you in the beginning, or is this a journey one must go on to fully understand the results of your success?
Obviously, hindsight is 20/20. Would I have liked to have felt or know all this when I started? Yes. And at the same time, I probably wouldn’t be the person I am today without measuring myself on actually not very meaningful things along the way. It didn’t feel good and yet I continued to do it. And, sometimes still do. I’m getting better. 
Interview continues below
Big Think
What impact did attending NSS as a student help shape you as you launched your university life and the beginning of your career? And what is your favorite memory of being inside the hallowed halls of NSS?
NSS was the greatest educational experience of my life. Bar none. I met extraordinary people and the school allowed me to push the boundaries of who I thought I was or could be. My passion for leadership was catalyzed at NSS. And, my first forays into it! I have so many great memories of being at NSS - a couple of favorites include my first year becoming part of the percussion section of the concert band, random! I carried around my drumsticks and felt cool. I never learned to play. But I had the sticks! I loved being on student council- I started off as class rep in grade 9 and was on it all the way through to being President. Most of all, I always felt there was a warm and kind spirit in the NSS halls. People were nice. Being mean wasn’t cool - whether you were on the football team or in drama. Unlike a lot of high school experiences I’ve heard about, NSS encouraged us to be ourselves and be proud of it. 


Interviewer, Jason R. Hughes was SAC ‘92 president, founder of the Youth Environmental Organization, NSS Air radio host, Stage Manager for drama, track & field athlete, and co-director of the annual NSS Fashion show and producer of the annual Battle-of-the-Bands. He is also a proud member of the Board of Directors for the NSS Alumni Association. He graduated from the University of North Carolina at Chapel Hill and lives at Fort Lauderdale Beach, Florida, running a large arts and cultural non-profit.