Female Founders: Kayla Glanville of Upaway On The Five Things You Need To Thrive and Succeed as a Woman Founder
An Interview With Candice Georgiadis
Be the greenhouse. Crediting the late entrepreneur Tony Hsieh who saw his role was to be the architect of a greenhouse. Founders are not meant to be the brightest colored flower or plant with the biggest leaves, we are here to create an environment where every plant can thrive. My role is creating and maintaining an ecosystem where my team can dig in roots and continue growing to their full potential.
As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Kayla Glanville.
Kayla Glanville is the Founder and CEO of Upaway, the world’s first and only company to combine travel organization tools with on-demand trip support in one app. Kayla’s passion is creating mission-driven companies at the intersection of technology and human empathy. As the founder of Upaway, she’s focused on building a team that reflects the communities that Upaway serves and is on a mission to make travel safe and simple for everyone by tackling unruly trip chaos.
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’m a natural-born leader: from my earliest memories at preschool leading all the other kids in pretend “school” (I was the make-believe teacher, of course) to captaining teams and spearheading high school inclusion groups. I’ve always found energy and purpose in enabling others to live their fullest, most fulfilling lives.
That said, I remember having limited visions of what’s possible at an early age. (Growing up in the 90s, I didn’t see many women at the top and often had my assertiveness labeled as bossiness — sexist perspectives that were unknowingly and unjustly dampening my self-confidence and limiting my aspirations.)
In college, a professor asked me, “What is your career goal?” to which I answered — without skipping a beat — a CMO (Chief Marketing Officer). I was a lifelong lover of community building and problem-solving, consumer marketing was my first love, and the career path seemed obvious.
Then that professor replied: “Why did you only say CMO? You’d be a great CEO.”
Those words stopped me in my tracks; talk about unlearning, reprogramming, and reconsidering assumptions! This quick interaction planted an entrepreneurial seed in the back of my mind: it’s possible.
So, that summer after graduation, I began my career at Nike, where I helped build the company’s Global Digital Strategy and social communities alongside notable marketing leaders and now-CMOs. In 2014, I joined Twitter to grow the company’s travel industry partnerships, where I worked with the world’s biggest airlines, hotels, destination marketing organizations, and experiential parks. Simultaneously, I co-led Twitter’s LGBTQIA+ group into a global entity, working on internal and external solutions for employees and global citizens.
This experience put the stressful consumer travel experience under a microscope and made clear the chaos that everyday travelers — often those who’ve been historically excluded or underserved — have to tackle alone.
Today, my commitment to equity and inclusion converges with my love of travel in Upaway: the first-ever travel app tackling trip chaos for everyday travelers. We built Upaway based on the experiences of everyday travelers who’ve been hung out to dry by the travel industry as traveling gets more and more chaotic, so you can get where you’re going safely and simply.
I often think back to that professor who challenged me to think beyond my self-imposed (often subconsciously learned) limitations and reflect in gratitude; sometimes, it takes a tiny spark — even years earlier — to ignite something big inside.
Can you share the most interesting story that happened to you since you began leading your company?
As a founder raising your first ten thousand dollars can feel impossible, yet, when we received our first offer in the triple digits, we turned it down. Even more surprising, it was the right partner and someone I would be thrilled to work with in the future.
Nevertheless, as I started to understand the world of equity, investments, and the structure behind startup deals, I knew it wasn’t the right path for our company. We decided to turn down our first big term sheet, keep bootstrapping, and bet on ourselves.
This was unexpected and an interesting turn of events because I never imagined turning down capital this early in my startup journey. What I learned through the experience was how to operate in a mindset of abundance versus scarcity. The scarcity mindset makes you think about the what if’s: what if another check doesn’t come, what if I can’t financially support this team, what if we are one of the majority of startups that fail.
I had a conversation with our advisor and executive coach who shifted my lens to an abundance mindset: recognizing, honoring, and believing that there will be more offers, ones we can build towards, visualize, and manifest into reality.
I never expected to turn down our first big investment offer, yet, this was one of the most interesting and impactful decisions I made as an early-stage Female Founder that has served our team well.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
Yes! Looking back it’s almost comical — but primarily cringey. While at Twitter, my job was to partner with Travel Brands and pitch Travel Industry Executives. As I stepped into the CEO role at Upaway from an Account Executive role at Twitter, I thought to myself: This can’t be that different. I know how to pitch, curate a partnership, and source the right talent.
Of course, it wasn’t that simple. Those are all essential skills that have served me well time and again, but as I went out to pitch investors for funds to ‘begin’, I realized that building a great pitch is a moot point if your product isn’t rooted in deep consumer insights.
There I was, a consumer marketer and builder who had a solution to travel chaos without ever running it by a customer. Yes, it makes me cringe just typing that out. But it’s true: we often follow solutions that we think are right. After four unsuccessful months of fundraising, I hit pause when a friend/ investor asked: How many customers have you talked to?
My heart fell so fast to my feet it took me a second to pick it up off the metaphorical ground. I, a professional who knew data-informed anything is always better than assuming everything, had been pitching a product rooted in weak insights; this was my first great, big ego check.
From there, I conducted over fifty interviews with folks from all backgrounds, all around the USA, who had varying levels of travel experience. It was then that two questions popped out like the chaotic monsters they are: limited trip organization tools and almost non-existent trip support. Today, we continue to build with one north: working with our customers to create products that enable them to thrive.
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?
So many folks have supported this journey, whom I’m immensely grateful for; it’s a genuine team effort at Upaway. I’d be remiss, not to mention our incredible team working tirelessly to make travel safe and simple for everyone and our Advisory team who guides our efforts.
That said, there is one person I couldn’t do this journey without, who without her unwavering love and support, this entrepreneurial journey wouldn’t be possible: my wife.
The entrepreneurial journey is long, unpredictable, and unstable; it requires massive amounts of sacrifice, financial hurdles, and an unwavering belief in what ‘could be’. Choosing a career journey with a seventy-five percent failure rate isn’t just stressful for entrepreneurs — it’s also stressful for our partners.
That’s why, as I’ve poured hours into late nights and full weekends, my wife has been the loving wind beneath my startup wings. Spousal capital is, yes, financial: without her salary, I wouldn’t have been able to step away from my corporate life and build something new. (A massive privilege that I’m grateful for every day.) But, too, spousal capital is about the unwavering belief and support in you, your team, and your dream for the future.
I’m enormously grateful to my wife for being my biggest believer, strongest supporter, and above all the person who whispers “keep going” when the journey gets almost too tough to bear.
To my wife: thank you, I love you forever.
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?
The lingering, expansive impacts of the historical exclusion of women in business spaces — precisely in entrepreneurial spaces — continue to impact founders today.
Men have historically benefited most from entrepreneurship because resources, access, and professional networks tailor to their lived experiences and success. I would argue, this is still the case today. Primarily male, mostly white, and often financially well-off, becomes the default, and anyone outside of that default is still vying for their opportunity.
Yes, the good news is opportunity and spaces for historically excluded founders are broadening: we’re seeing an unprecedented amount of founders, VC firms, and startup teams enter the market with impressive funding. That said, the success of those companies hinges on their access to resources and professional networks.
In my experience, I see many women establish companies with brilliant ideas and incredible business plans. Sadly, those businesses often never see the light of day because the access to resources and professional networks weren’t built inclusively from the start; they don’t have equitable support for scale.
The solution lies in rebuilding a foundation that champions and empowers all visionary entrepreneurs — not just those who were born with the right skin color, gender, or socioeconomic status. This requires unlearning and reframing our assumptions about entrepreneurship and in creating teams that reflect the diverse communities our products serve.
Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?
Government:
• Drawing from Susanne Althoff’s “Launching While Female”, in 1988 politicians championing a Women’s Business Ownership Act focused repeated a bold prediction: “that this legislation would allow women to own half of the nation’s businesses by the year 2000.” Well, in 2002, only 28% of all US businesses were owned solely by women. Today in 2021, 40% of U.S. businesses are owned by women. While this trend is moving in the right direction, it has taken over thirty years to get to this point and we’re not yet at the goal.
• Women often take on more responsibilities outside of work: housework, childcare, family organization, and more. As we venture into entrepreneurship, women need…
◦ Monetary support through non-predatory governmental grants and loans that don’t require revenue (this effectively counts out early tech entrepreneurs, who often operate in a monetary deficit in their early stages)
◦ Affordable childcare
◦ Full reproductive rights
◦ More women-identified folks and historically excluded communities in elected positions of influence across all levels of government
Society:
• Create space and opportunities for female entrepreneurs, including access to free or affordable childcare, nonpredatory financial support to pre-revenue first-time female founders (because a ‘friends and family’ fundraising round is a privilege many don’t have), and reimagining women’s home contributions to be more equitable across housework, child-rearing, and family organization.
Individuals:
• Be thoughtful about who you put on your Cap Table. From LPs, to your investors, your team, and Board — each person has the opportunity to make a ton of money if your venture drives outsized returns. As we build our Cap Table, I’m always thinking about who will benefit from our success and if it will drive generational wealth and capital to folks who’ve been historically excluded. Your product can be a changemaker for your customers, and your Cap Table can be a changemaker for every investor, their families, and generations to come.
This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?
No one knows our lived experiences as well as we know our own. We’ve all seen the product or commercial that rings so tone-deaf, so unrelatable, we think: how did that even make it to market? For decades investors have invested mainly in male-led companies because, no surprise, 81% of VC investors are male. (source)
As humans, we tend to navigate towards familiarity and trust people who look and experience the world as we do. So, what happens when the LPs, the VCs, and the companies are all men? We get products that solely reflect the male experience: this can show up in…
• Small, but impactful ways like naming children’s workshop toolsets as “Big Boy Toys” when, for example, our niece loves to build and we chose to put black tape over words to express who the toy is really for: “Big Kid Toys”
• Huge concerns, like crash test dummies that are modeled after male bodies; no female body dummies are used in front-impact crash tests. The result? Women are seventy-three percent more likely to be seriously injured in frontal car accidents. (source)
As founders who identify as female, we have the opportunity to build inclusive, diverse teams that reflect the unique communities we serve. We get to build our Cap Tables in such a way that drives more leverage towards historically excluded folks, engage investors who align with our values, and build products that solve our real-life challenges.
What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?
“Workaholics drive success.” This myth should kick rocks, and no one will miss it. (Hopefully.) While the workaholic-in-a-garage archetype of Gates, Bezos, and Zuck dominate the narrative the reality is this “lone wolf” approach to startups never worked for me and I haven’t seen it work for others. Startups are a long game and the process will test your endurance more than ever before; take time to rest, prioritize time with your loved ones, and leave time for play. After periods of focused, productive work the times of diffusion — i.e. stepping away — are when your brain ties those loose ends together and creates the magic. (Yes, keep a notepad nearby!)
“We wrote a deal on a napkin!” Alright, if this was you then a huge congrats. In likeness, though, the narrative of having an idea and raising tons of money through a few network introductions doesn’t happen often; when it does, it’s typically going down between “trusted” folks within networks. When networks and access to resources aren’t extended equitably, we see outlier success stories like the napkin story but the reality is more steadfast and persistent than your Twitter and LinkedIn timelines will lead you to believe.
Before you begin… there’s no one way, no right way. You can (and probably will!) learn-via-doing; you’ll make mistakes, pivot a ton, and be better for it. Before I took the “leap” into entrepreneurship I spoke with a mentor-now-advisor about my idea, but when he asked why I hadn’t started the company my reply was this: I have no idea where to start. It was at this moment they looked at me and said, “no one does” and kept walking. The truth is we’re all figuring it out, and the philosophical stoplights on our road of life won’t all be green at the same time. The trick to beginning is to simply begin.
Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder, and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?
I’m of the opinion that anyone who says who a founder should be, or who’s likely to succeed, is sharing that perspective from the biases of their own lived experience. The traits that have helped me be successful in this entrepreneurial journey (commitment, empathy, vision) are likely different for other folks and their companies.
The one trait, however, that I see consistent across entrepreneurs is belief. We believe something can be better, so we create it. We believe we can, so we do. We believe in our teams, in our vision, in our products to such an extent that the odds stacked sky-high against us are mere shadows in our peripheral view as our focus stays laser-pointed towards success.
Ok super. Here is the main question of our interview. Based on your opinion and experience, What are the “Five Things You Need To Thrive and Succeed as a Woman Founder?” (Please share a story or example for each.)
1 — Unlearn and reprogram. A mentor of mine said, “if you want to get to know yourself (the good, the bad, and the ugly), start a company.” I expected to learn about Cap Tables, funding rounds, and building teams. What I didn’t expect was unlearning what I thought to be the perpetual truths of “productive” working habits.
The accolades you have, who you think you are, the disappointment of letting someone down, and the guilt of taking a break all lead to burnout as a founder and leader. If I pushed myself to burnout through habits that did not serve me, I couldn’t be there for my team or my family. I put in an enormous amount of cognizant work into unlearning what our society programs us into thinking is efficient. I relearned and reprogramed with a growth mindset to be the best for those around me.
2- Find and empower your champions. Most folks have mentors that can help us contextualize ideas, soften blows, and guide us. They are incredible at providing support and creating stability throughout our careers. Champions or sponsors, as TED Talk speaker and business executive Carla Harris calls them, are the people who will be in the room fighting for your big moments of change. They put their verbal stamp of YES on you and pound the table to ensure you are represented.
Both mentors and sponsors are important roles, I encourage Female Founders to seek out both while being clear with your expectations. This empowers them to understand what you’re looking for, what you need from them, and it’s on founders to empower them with updates on what you’re working towards.
3 — It’s all about the team. I don’t know everything and have yet to meet anyone who does. There are always individuals who have specialized knowledge and insight superior to mine. My goal as a leader is not to know every answer to a question my job is to find and empower the folks who are subject matter experts.
As a founder, I am here to prompt the discourse around what we need, find the experts within that area of our business, and remove roadblocks to enable them to do their best work. If I do this correctly, it means I have an entire team who can put their heads together and find the best solution, versus having to find every answer independently.
4 — Be the greenhouse. Crediting the late entrepreneur Tony Hsieh who saw his role was to be the architect of a greenhouse. Founders are not meant to be the brightest colored flower or plant with the biggest leaves, we are here to create an environment where every plant can thrive. My role is creating and maintaining an ecosystem where my team can dig in roots and continue growing to their full potential.
5 — Get creative. The way things “should” happen for a founder is far different than how it is experienced by historically excluded founders, particularly women. Cis white men with access to capital and networks are featured as unicorn success stories, yet this is not the reality for most.
I hired my team and bootstrapped the business before any capital was even plausible. From power washing driveways in San Francisco to selling stocks for our overhead costs, I got creative to source enough funds to get where we needed to be.
To female and historically excluded founders who don’t have a family and friends funding round, I encourage you to bring people in who see your vision and are excited to build together. Women are uniquely tasked with figuring it out for not only ourselves but our families. Throughout centuries we’ve powered through this juggling act of life, as society expects more from us in the workplace and at home. Through this, we’ve become well-rounded, effective, and empathetic leaders who I hope to see more of every day.
How have you used your success to make the world a better place?
Prior to founding Upaway, I’ve always had a day job where within that workforce, I found a second project around equity, representation, and making inclusive spaces. I love working with the elderly, supporting women’s shelters, empowering student-athletes, and advocating for the LGBTQIA+ community.
I walked away from corporate life because I didn’t want my job and my societal contributions to be separate anymore. I’ve created a product and a company that is focused on inclusion, integrity, and helping everyday people thrive. Now, I get to work 100% at something that will provide millions of people access to support that makes their lives better.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
Of course, I have my own ideas on how we can change the world, but my ideas are not representative of our collective community. Throughout this journey, I’ve learned that the greatest movements are never based solely on personal experiences.
I would first start with questions to find where the opportunity is to provide the most amount of good for the greatest number of people, through asking real folks about their lives. The power lies within getting and hearing the voices of people who need a movement and enabling them to make it happen.
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.
Raise your hand if you aren’t someone who idolizes others?! There are many folks with whom I would love to have a thoughtful conversation, however, I don’t feel any one person has all the answers. That said, someone I admire is Alicia Keys. I appreciate her authenticity, love her perspective, and admire how she shows up as her full self in all spaces. She’s an incredible businesswoman, an accomplished singer/songwriter, and leads with authenticity. Also, Emma Lovewell from Peloton — let’s get lunch!
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
Female Founders: Kayla Glanville of Upaway On The Five Things You Need To Thrive and Succeed as a… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.