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Madeline Pratt of Fearless Foundry: “More Funding”

…We need more women founders because we need to reinvent the way that we work. If this pandemic taught us anything, it is that the traditional working world doesn’t work well for women, or families for that matter. As schools and workplaces have been shuttered, we’ve seen first hand the impact it has had as […]

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…We need more women founders because we need to reinvent the way that we work. If this pandemic taught us anything, it is that the traditional working world doesn’t work well for women, or families for that matter. As schools and workplaces have been shuttered, we’ve seen first hand the impact it has had as women exit the workforce because it doesn’t offer the flexibility or support they need. In order for this dynamic to truly shift, women need to change the workplace by working for themselves. Rather than waiting for corporate environments or governmental policies to catch up with the times, we can create our own companies to pave a path for a workplace that actually works for women.


As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Madeline Pratt.

Madeline Pratt is the founder & CEO of Fearless Foundry, a creative consultancy that supports ambitious humans in building branding, marketing, and business development strategies that allow them to make a meaningful impact in the world. Madeline is an outspoken force for promoting equity, collaboration, and community in business and she spends her time working with clients, creating content, and growing her team. You can connect with her on social media by the handle @madelinekpratt.


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 have always felt compelled by the inequities within the world and been curious about how we could use intellect and creativity to solve them. Looking back, I think this is something that was cemented into my subconscious from a fairly young age, as I watched my mom navigate single motherhood and all the burdens that came with trying to run her own business while providing for her children. Even after she remarried, the pressure on her didn’t seem to subside, and I realized that the burden was one that working women everywhere seemed to be carrying.

I became a mother myself during my junior year of college, and within a few years was raising my son on my own. I had graduated with a degree in Medical Anthropology but immediately set it by the wayside to take the first job that was handed to me, which happened to be in sales in the software industry. As a single mom, I had more tenacity than most to make sure I hit quota, and over time I rose the ranks of different companies until I became a leader of Global Business Development of a fast-growing start-up.

While I loved the team, and the industry I was in, over time, this same issue of inequity kept showing up seemingly everywhere I went. Female friends of mine would share stories of trying to start their own businesses and having bank loan applications be denied. Women strangers would approach me in coffee shops sharing their ideas for a company, and then point out all the hurdles standing in their way to putting their ideas into motion. Eventually I found myself spending almost all my free time coaching women on the strategies and tech they might need to bring their business ideas to life.

What started as a side project began to take over the whole of my heart, and I realized my passion lay in helping ambitious founders, particularly those that are traditionally underrepresented, start, grow, and scale companies. So, in 2018, I left my day job to begin consulting full time, and in the past three years, I have grown my company to be able to offer well-paying work to a team of 10 women, and creative consulting services to dozens of clients from around the globe that believe in the power of business to change the world for the better.

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

I will never forget when I took my two-week-old baby to a tech conference.

After my second son was born over two weeks past his due date, I made the difficult and post-partum addled decision to still attend a conference that I had planned to participate in prior to getting pregnant. What I had planned to be my first trip back after at least 4 weeks of solid bonding and resting with my new baby, turned into an intense and eye-opening experience with my mom, my new baby, and my 6-year-old son in tow. While the company I was working for was supportive and gracious of me taking my family along for the ride, I had no idea how challenging it would be to pump or nurse my son in between sessions, and by the last day of the conference, I decided to just carry him around all day strapped to my chest rather than be separated from him any longer.

It is one thing to be a woman at this tech conference, as we’re among the minority of attendees, and it was another thing entirely to be walking around with a baby strapped to my body. I might as well have had two heads based on some of the looks I got. But as the day was ending, and I was waiting in line to get a coffee, I saw a woman trying to get a peek into the baby carrier. I caught her eye and smiled, realizing she was happy to have a baby in the midst of the male-dominated space.

Her smile back made me realize that despite how challenging the past few days had been, it was critical for me and other women to show up and be seen in the tech industry, even if it means we bring our babies along for the ride. Embracing our identities as mothers instead of shying away from it is the only way we will shift culture. From that point forward, I have made a point to bring my sons to the office whenever I needed to, to demonstrate that my identity as a mother wasn’t something that I could simply drop at the door, and make a point to encourage the creation of a culture where others embrace parenthood proudly.

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?

I’ll never forget one of the first times I flew internationally to meet with a large consulting client. Although I had taken many meetings like this earlier on in my career, this meeting was the first I had taken while representing solely on behalf of myself and my company. I spent hours pouring over what I should wear to look the part of a “highly valuable consultant”, and ultimately settled on a pencil skirt, blazer, and heels.

Fast forward to the day of travel, and my flight is delayed by almost 11 hours, and my only option was to fly a redeye and head straight to the client’s office from the airport. With my bags already checked, I had no choice but to buy makeup and hair products in the airport so that I could “put myself together” on the plane, and change as fast as possible in the bathroom once I landed before beelining it to the client’s headquarters.

When I finally made it to their lobby and took a look around, I realized that everyone at the tech company was dressed in t-shirts, jeans, and sneakers, just as I had been on the flight. While I had been losing my mind over how to showcase myself as a “put-together consultant” despite the circumstances, I could have absolutely saved my energy. I was wildly overdressed compared to everyone I met and needless to say, I showed up the next day in the same casual attire as everyone else. More importantly, though, I realized that I didn’t have to be anyone other than myself to impress the client, and if I did, then those weren’t the people I wanted to work with. It was an important lesson that I’ve continued to carry forward in my career, and I’ve now got a rule that if someone doesn’t approve of me in sneakers then we likely aren’t meant to work together, and that’s okay by me.

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?

Of all people I am most grateful for in my career, I would have to point to the second in command at my company, Aljolynn Sperber, who is the VP of Strategy at Fearless Foundry. I met Aljolynn right when I was teetering on the verge of whether or not to build a team and truly scale my company. When I first hired her, it was as a contractor to help me bring my marketing vision for the business to life. However, as soon as we started to collaborate, I knew I had found a dear friend, and ultimately an incredible support system.

She is the kind of person that will never let you speak self-deprecatingly in her presence, and it has dramatically changed the way I and our team talk about their abilities. I will never forget being on a call with her and saying “I’m sorry my brain isn’t working right now”, and having her stop me in my tracks and say “Can you rephrase that, please? Your brain is beautiful and capable.” Having someone who encourages you to always speak, think, and act in a loving way towards yourself has a major ripple effect on how we perceive our own worth and the worth of others, and she has always helped me to elevate and believe in myself and my abilities.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I might be the ten-thousandth woman to say so, but reading Glennon Doyle’s book Untamed this past year had a profound impact on my life and on my business. I grew up knowing deep in my bones that I didn’t belong in any sort of the boxes that society had deemed were acceptable for girls and women. Doyle’s words are an anthem for any woman that is ready to break free from stereotypes and recreate a life that is true to themselves, and I am forever grateful for the guidance her work has given me and countless others.

Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?

My favorite life lesson quote hangs in my office and comes from the words of Brené Brown:

“Let go of who you think you’re supposed to be; embrace who you are.”

When I began building my business, I would lose a lot of sleep and energy over thinking about who I had to be to impress a certain kind of client, or to attract the types of companies I wanted to work with. Over time though, I have come to find that the most meaningful experiences and lasting relationships in business have come from the situations where I have shown up as 100% who I am.

How have you used your success to make the world a better place?

It is incredibly important to me that my success has a ripple effect and is able to encourage, support, and inspire other women along the path of entrepreneurship. In action, this has involved making sure that in everything I do, I think about that ripple, and only say yes to opportunities, clients, collaborations, projects, and people that allow for it to grow bigger than it would be if I was operating on my own. It also means that I make a point to give back wherever I can in a meaningful way. Whether it is mentoring young women in tech, speaking and teaching on topics like pricing or negotiation, sponsoring events and creating communities for women founders, or offering pro-bono consulting work, I am always striving to support other women entrepreneurs because I know that with that support they will be able to help the other women that follow in their footsteps.

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 biggest barrier holding women back from founding companies is structural support, and quite frankly, money. Starting a company involves taking big risks, particularly on the financial front, and because of the gender pay gap, women do not have the same cushion to catch them if they misstep getting an idea off the ground.

When I decided to start my own business, the only reason I felt able to do so was because I had money in the bank and could afford to take the leap. I had risen the ranks in the tech world and had managed to save up around 20,000 dollars to tide my family over until revenue was coming through the door. But taking the risk was still terrifying, as I had been the primary income earner up until that point, and that cushion was barely enough to replace 2 months of the old salary my family was used to having show up in our bank account each month. Simply put, I couldn’t afford to fail. I gave myself three months, dove in headfirst, and started earning consulting revenue by my second month in business.

But having that 20,000 dollars? It made all the difference, and it gave me the ability to take the risk of starting my own thing. Without it, we wouldn’t have been able to afford for me to start my own business and I’d still be working in tech.

I was extremely privileged to have worked in a field that allowed me to put that money away, and few women have that opportunity. What women need more than anything to be able to start and scale companies is the financial backing to do so. Research shows that women-run companies achieve 35% higher return on investment than their male counterparts, and yet women still make up less than 15% of venture capital investments, and women of color receive less than 1% of that number. Structurally, we need to see major shifts and investments in women, be it through venture capital, angel investing, small business loans, grants, or microfinance opportunities to set women up to be able to take on the financial costs and risks that come with founding a company.

Can you share with our readers what you are doing to help empower women to become founders?

Even before starting my own company, I saw it as a critical step to nurture the next generation of women leaders through hiring and mentoring young women in tech. When I left that world to start my own company, I maintained my mentees and still offer regular support to them as they’ve branched out into new career paths and starting companies of their own.

I also host a podcast called Finding Fearless, which I originally launched to hold space to share the stories of women leaders and entrepreneurs. When I was first thinking about founding my own company, I couldn’t seem to find any podcasts that were highlighting the stories of women on the path and everyday founders, rather than highlighting women who had built multi-million or billion-dollar brands. Don’t get me wrong, I love celebrating successful women, but I wanted to hear stories of women like me who were in the earlier stages of the entrepreneurial journey, so I started the podcast to share those stories. Today, our podcast has featured over 50 women from all walks of life and served as a platform to share their stories in hopes that they might inspire others along the path of entrepreneurship.

Lastly, in my day-to-day work, I coach, teach, speak to, and mentor women that are starting or scaling their businesses and offer them support with marketing, branding, and business development. My belief is that through this work my team and I are giving tools and confidence to female founders that supports their growth and success and that in turn each woman we work with will be able to inspire others to follow in her footsteps.

This might be intuitive to you but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

One primary reason why we need more women founders is because we live in a world desperately needing innovation. There are a lot of major challenges, inequities, and inefficiencies in our society, and so much of the way we live and inhabit the earth is ripe for reinvention. However, we’re not going to truly be able to tap in to the full breadth of potential solutions with only a portion of the population invited to the conversation. We need a diverse array of perspectives and experiences at the table in order for the best innovations to bubble to the surface.

In my experience working women across a variety of industries, I know that we take a much more holistic approach to the companies we create and the product and services we offer. That kind of sustainable and collaborative thinking is critical in the next era of industry. We need to ensure that businesses think critically about their people, and the impact their products and services have, just as much, if not more than their profits if we are going to ensure that the Earth is habitable for future generations. Women bring this collective and systemic perspective to business, and we need more of this approach to right side our current extractive relationship with our planet.

Most importantly though, we need more women founders because we need to reinvent the way that we work. If this pandemic taught us anything, it is that the traditional working world doesn’t work well for women, or families for that matter. As schools and workplaces have been shuttered, we’ve seen first hand the impact it has had as women exit the workforce because it doesn’t offer the flexibility or support they need. In order for this dynamic to truly shift, women need to change the workplace by working for themselves. Rather than waiting for corporate environments or governmental policies to catch up with the times, we can create our own companies to pave a path for a workplace that actually works for women.

Ok super. Here is the main question of our interview. Can you please share 5 things that can be done or should be done to help empower more women to become founders? If you can, please share an example or story for each.

  1. More Funding — Starting a business costs money, and women are already at an economic disadvantage due to the wage gap. Without funding, we’re slower to start or scale our companies. I know countless women with dreams of owning their own business, but they don’t have the dollars to get things off the ground. It’s critical that we build better pipelines for financing and investments to be funneled into the hands of women founders so that we have the resources to bring our business ideas into being.
  2. Systemic Support — We still live in a world where women bear the brunt of caring for family members, managing the mental load, and taking on way more than our fair share of household responsibilities. In order for female founders to be successful, we need support systems in place that give us the time and capacity to commit fully to our companies. We need better childcare resources, encouraging partners, educational opportunities, and incubation programs that are designed specifically to be supportive of women so that we have the backing we need to succeed.
  3. Mentorship — Building a business is a big deal, but it seems less scary when you have the guidance of someone who has walked the path before you. Women founders need more opportunities to meet and be matched with mentors to serve as a sounding board and source of advice for us as we navigate the uncharted waters of entrepreneurship. The more female mentors we have step forward to offer guidance, the more future female founders will follow.
  4. Media Coverage — There is a saying: “If you can see it, you can believe it.” However, when it comes to women in business, there aren’t enough examples being highlighted of women that have walked this path before. Until we see authentic examples of female founders who forged their own path being represented equitably in our media, women will continue to doubt their abilities in the world of business. We need media coverage to expand and to celebrate the stories of all types of women founders, not just the ones that make it to wall street, so that we can see that the example already exists and that we have the right to walk the path of entrepreneurship and found entities of our own.
  5. Community — The most important thing on my journey as a entrepreneur has been connecting with other women that are walking this same path with me. Community is essential for us to bounce ideas off each other and to ensure that we don’t feel alone. By creating community, we as women build meaningful support systems, and also have the opportunity to economically uplift each other by buying from and supporting each other’s businesses. In my mind, community and collaboration are essential to ensuring women don’t just start businesses, but that they also grow and thrive.

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.

I believe deeply in the power of entrepreneurship as a path to equity. There are so many systems that need rebuilding and so many big problems that need solving in our world, and I believe that great innovation sparks when someone cares enough to start a company to tackle the issues at hand. Building a business is no small feat, but when you persist and pioneer along the path of entrepreneurship, you not only create an asset for yourself, you create the potential to make the world a more equitable place.

My greatest wish is to spark a movement that inspires anyone that doesn’t see a place for themselves in the systems and companies that exist today, to forge their own way in the world by starting their own business. If we persist as entrepreneurs and create companies that allow for those that work for us to have access to the opportunities, income, flexibility, and other values that we were denied in traditional working environments, we can shift the working world for the better and shape a more equitable society for all.

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.

I would love to have brunch with Shelley Zallis of The Female Quotient. I have long admired her work and company, and in particular, am inspired by what she has brought to the gender equity conversation around the importance of women taking up space in otherwise male dominant events or industries.

How can our readers further follow your work online?

Readers that want to connect and follow with my work can find me on the Fearless Foundry website or LinkedIn, or on social media (Twitter, Instagram & Clubhouse) by my handle @madelinekpratt.

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

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