Female Founders: Natalie Gillard of FACTUALITY On The Five Things You Need To Thrive and Succeed as a Woman Founder

An Interview With Doug Noll

Don’t Take it Personal: When I decided to pursue Factuality full-time, my news was met with laughter, mockery, scolding, and a sprinkle of positivity. My social circles, which had doubled as my support system, dwindled. Before I realized that I was likely being impacted by the projections of others, I took everything personally. With the help of a great therapist and the exploration of self-help resources, I now know — whether good or bad — what people say to me and about me has absolutely nothing to do with me. Don’t take the behaviors of others personal.

As a part of our series about Women Founders, we had the pleasure of interviewing Natalie Gillard.

Natalie Gillard is the creator of FACTUALITY, a facilitated dialogue, crash course, and interactive experience, that simulates structural inequality in the United States. Over the last seven years, Natalie has led virtual and in person FACTUALITY facilitations for over 57,000 global participants.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I am the daughter of an immigrant mother and my father was part of the great migration out of the Jim Crow South in the U.S. I witnessed firsthand the struggles that coincided with the Black, immigrant, and Black immigrant experience. Among my earliest memories was this visceral awareness of the fact that my lived experiences at home and in my community were never depicted accurately in the media or in my classroom experiences, and beginning at a very young age, I began making attempts to narrow that gap.

Social equity has always been at the forefront of my personal, professional, and educational core values. Nearly every paper and presentation during my undergraduate and graduate school experiences focused on the prevalence of fact-based inequities in the United States. My graduate thesis focused on the origins and pervasiveness of hair texture and skin tone complexities in the African American experience. My 11-year higher education career began as a Student Leadership and Diversity Programs Coordinator and culminated as an Assistant Vice President for Multicultural Experiences; every role in between focused heavily on some element of diversity, equity, and inclusion (DEI).

A chance encounter in 2015 would lend itself to the creation of my greatest achievement in the DEI space to date: a facilitated dialogue, crash course, and interactive experience that I proudly call Factuality. Designed to simulate fact-based inequities in the U.S. and around the globe, Factuality is arguably the easiest way to engage individuals from all backgrounds in conversations on diversity. One simulation at a time, through a lens of empathy and grace, I am able to close the gaps between lived experiences and perceived experiences, while simultaneously fulfilling aspirations that originated during childhood.

Can you share the most interesting story that happened to you since you began leading your company?

Several years ago, I facilitated an intimate session of Factuality and the current Governor of Maryland, Wes Moore, was in attendance!

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 get you to where you are? Can you share a story about that?

I remain eternally grateful to a former colleague, who insulted my previous DEI training adaptations, thus igniting the desire to develop my own. Following our brief exchange, the idea of finding “the best diversity board game” immediately entered my mind. When I couldn’t find what I was looking for on Google, I decided to build it myself. Within a year, I officially launched Factuality as an LLC. Two years later, Factuality became my full-time job and two years after that, Google hired me to facilitate several Factuality experiences; they have since emerged as one of my biggest clients. To date, Factuality has reached nearly 60,000 people on six continents.

Back to that colleague… our encounter and the consequential development of Factuality left me with the most important reminder in life. Seek and extract the silver lining in all things that you perceive as negative. Less-than-preferred encounters almost excite me these days because I now know that something good awaits.

That colleague reached out to me a few times to inquire about a facilitation and because yesterday’s price is not today’s price, my fee exceeded their budget, but most importantly, I had the capacity to genuinely thank them for serving as the catalyst to the most transformational experience of my life.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

Lack of Intersectional Representation: While roughly 20 percent of funded companies have women founders, as a Black founder, I’m immediately wondering what percentage of those founders are women of color and where are they getting their funding from? As a woman who has navigated disabilities, what percentage of funding goes to women with disabilities? And, as an ally to the trans community, what percentage of funded companies have trans women founders?

Lack of mentorship and support: Women entrepreneurs have a harder time finding mentors and support networks than their male counterparts, which can make it more challenging for them to navigate starting and growing a business.

Antiquated Societal Norms: Societal expectations around caregiving and household responsibilities have proven to make it harder for women to balance the demands of their personal and professional lives. Coupled with the time-intensive demands of entrepreneurship, antiquated societal norms can undoubtedly hinder the opportunity to become a founder.

Flexibility: Albeit demanding, entrepreneurship can offer tremendous flexibility. As an (established) founder, I have the ability to set my schedule and work from anywhere in the world.

Imposter Syndrome: Feelings of self-doubt and inadequacy, make it challenging to take the leap into entrepreneurship. In the midst of navigating imposter syndrome, start asking yourself, what if it does work out?

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1 . Protect Your Idea at All Costs: Before sharing your idea, lock down the website domain, secure all appropriate social media handles (keep them consistent across platforms), and take the time to file all appropriate trademarks. File for your LLC, which serves as an additional layer of security and protection for you and your business. Additionally, keep your big ideas close and be careful with whom who you share them. A former coworker took my entire concept of Factuality and submitted it to a conference and got accepted!

2 . Bills Bills Bills: Open up a business account, properly track your income and expenses, and pay your quarterly taxes! I talk to my accountant, Sam, more than I care to, but he keeps me and all of my Factuality finances in line. He likes to remind me that he’s the good Uncle Sam.

3 . Credit Rules Everything Around Me (C.R.EA.M.): I almost exclusively use my credit card to pay for all of my expenses; and, I pay my credit cards off in full on a monthly basis, which means I never incur a monthly fee for using them. I have a personal and business credit card, which are both tied to the same rewards system. I used my points for flights, hotels, a gorgeous nearly 9ft shelf from CB2, high-end knives (I enjoy cooking), and a Roomba (I don’t enjoy cleaning). I essentially get paid to use my credit card! If you’re already spending actual cash or moving cash through your debit card, why not get paid for it? It also makes reconciling end-of-year business expenses very easy for the good Uncle Sam.

4 . Save Your Coins: After all of that talk about spending, now I’m talking about saving. Condition your mind to understand that as an entrepreneur, 100% of every payment that you receive is 100% not yours. The economy has been in a peculiar position for some time, inflation has yet to subside, and layoffs are on the rise but I have zero worries because I save my coins.

5 . Don’t Take it Personal: When I decided to pursue Factuality full-time, my news was met with laughter, mockery, scolding, and a sprinkle of positivity. My social circles, which had doubled as my support system, dwindled. Before I realized that I was likely being impacted by the projections of others, I took everything personally. With the help of a great therapist and the exploration of self-help resources, I now know — whether good or bad — what people say to me and about me has absolutely nothing to do with me. Don’t take the behaviors of others personal.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

No, not one, but several. Because Factuality is an eight-player experience, I would require eight attendees at a private breakfast that would lead into a private lunch. On my list would be Oprah, Jane Elliot, Ava Duvernay, Angela Davis, Tim Wise, Nikole Hannah Jones, Robin DiAngelo, and Heather McGee. I am routinely inspired by their commitments to social equity, and it would be a total dream to engage that collective level of brilliance over a Factuality facilitation.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

About the Interviewer: Douglas E. Noll, JD, MA was born nearly blind, crippled with club feet, partially deaf, and left-handed. He overcame all of these obstacles to become a successful civil trial lawyer. In 2000, he abandoned his law practice to become a peacemaker. His calling is to serve humanity, and he executes his calling at many levels. He is an award-winning author, teacher, and trainer. He is a highly experienced mediator. Doug’s work carries him from international work to helping people resolve deep interpersonal and ideological conflicts. Doug teaches his innovative de-escalation skill that calms any angry person in 90 seconds or less. With Laurel Kaufer, Doug founded Prison of Peace in 2009. The Prison of Peace project trains life and long terms incarcerated people to be powerful peacemakers and mediators. He has been deeply moved by inmates who have learned and applied deep, empathic listening skills, leadership skills, and problem-solving skills to reduce violence in their prison communities. Their dedication to learning, improving, and serving their communities motivates him to expand the principles of Prison of Peace so that every human wanting to learn the skills of peace may do so. Doug’s awards include California Lawyer Magazine Lawyer of the Year, Best Lawyers in America Lawyer of the Year, Purpose Prize Fellow, International Academy of Mediators Syd Leezak Award of Excellence, National Academy of Distinguished Neutrals Neutral of the Year. His four books have won a number of awards and commendations. Doug’s podcast, Listen With Leaders, is now accepting guests. Click on this link to learn more and apply.