24 October 2023 |

5 Learning Lessons from Top Female Founders


Becoming a fintech founder revolves around inclusivity, not exclusion. 

The founders I’ve had the privilege of interviewing all share a common thread: a deep concern for societal and public issues, an impatience with waiting for others to act, and a belief in the power of making a difference while turning a profit.

It’s about making an impact and converting innovative ideas into billion-dollar businesses. During an on-stage interview at the L’Attitude Summit in Miami last month, I had the pleasure of sitting down with two remarkable founders, Paola Santana, the CEO of GLASS, and Maxeme (Max) Tuchman, the CEO of Caribu, which she sold to Mattel in 2022.  

Having raised over $6 million in venture funding and being the first Latinx founder to secure the maximum in equity crowdfunding, Max is now dedicated to getting more funding to startup founders like her while helping Miami tech founders find community. 

For Paola, Glass – a software ecosystem using Artificial Intelligence to power high-performing governments – secured $3 million in funding earlier this year, and she’s just getting started. 

Today, I want to shed light on these two extraordinary women whose journeys inspire all current and aspiring female fintech entrepreneurs. I’ll also share their practical advice for navigating the highs and lows of entrepreneurial life, especially as women in leadership.

Think of this as essential guidance – required reading, if you will – for the fintech founders reading this column and any aspiring entrepreneurs contemplating their own business endeavors after witnessing the paths Paola and Max have blazed.

Let’s go! 

Paola Santana’s journey began with an earnest desire to transform the political landscape and create significant change in her home country, the Dominican Republic. Recognizing Latin America’s sensitivity to societal issues, she sought to drive widespread positive change rather than address problems incrementally. 

Initially, she became a lawyer and aspired to be a politician to achieve her goals. However, her quest for rapid change led her to Silicon Valley, where she founded GLASS, a startup revolutionizing government procurement through pioneering G-Commerce. 

Maxeme Tuchman’s story is equally inspiring. She shared her experiences as a Cuban-Jewish Latina and how her family was familiar with seeking refuge. That impacted her professional trajectory and took her from a career in public education to a quest for innovative solutions in the tech realm. 

Her company, Caribu, was conceived to connect children with their families and friends through interactive storytelling. The company’s accolades, including recognition from Apple, TIME Magazine, and Fast Company, and Max’s experiences highlight women’s inherent strength, combining resourcefulness and resilience. 

She stresses that as women and Latinas, they bring more than just determination to the table – they bring creativity and a strong sense of responsibility for creating a better future for all.

Shared Strengths: The Foundation of Success

What struck me most during our conversation were the shared strengths that have undoubtedly propelled these two entrepreneurs to success. These strengths offer invaluable lessons for those looking to follow in their footsteps:

  1. Clarity on the Problem

Paola’s crystal-clear understanding of the issues she aimed to address, such as inefficiencies in government procurement, fueled her success. Entrepreneurs should focus on comprehending the problems they seek to solve, as this can attract investors and partners who share their vision.

As Paola aptly put it, “The exciting thing about clarity is that in my case, my second tech startup, GLASS, focuses on building government marketplaces. For me, it’s a no-brainer. While everyone talks about how governments make purchases with contracts, nobody discusses the immense market of governments using credit cards for small purchases, which amounts to a $4 trillion market. 

I have clarity about the problem, the facts, and the numbers. You can argue with me about governments being slow adopters or making decisions differently than enterprises, but you can’t argue with the fact that small government purchases constitute a $4 trillion market.”

2. A Dash of Impatience and Comfort with Discomfort

The ability to embrace discomfort is vital in both of their journeys. Breakthroughs often happen when navigating uncharted territories. It’s a lesson that encourages entrepreneurs to be adaptable, unafraid of change, and open to learning.

As for impatience, Max shared that she’s generally an impatient human. As a fellow female founder, I can resonate with this impatience by waiting for others to solve a problem when I know I can do it myself and even better. 

“As an impatient human, I realized that entrepreneurship was the only place where I could solve problems at the speed I desired,” said Max. “It gave me the flexibility to control my destiny and make a difference at the pace my children deserved.”

For Paola, the discomfort was palpable while building her first startup, focused on drone delivery. She emphasized that innovation often stems from unfamiliar terrain, saying, “That discomfort tells me I’m doing something new, both for me and the world.”

3. Resourcefulness

Entrepreneurs must be incredibly resourceful, mainly if they are women or people of color. Growing up as a first-generation Latina, language, and access to resources might be limited, instilling the ability to thrive in resource-constrained environments. Resourcefulness becomes a superpower, enabling entrepreneurs to achieve more with fewer resources.

Paola highlighted this power, noting, “Investing in women yields better returns.” 

She’s right. Women-led companies generate 78 cents for every dollar of funding, compared to male-founded startups, which produce just 31 cents.

Furthermore, being underestimated becomes another superpower. Paola explained how this underestimation led her to find creative solutions and build connections with others.

4. Lean on a Support System

Max knew what he was talking about when he stressed the importance of seeking advice and support from like-minded individuals. After all, who knows the struggles and triumphs of being an entrepreneur better than someone who has been through it themselves? 

Finding mentors, advisors, or fellow entrepreneurs who share your background can open up a new world of valuable insights and guidance. Not only can they provide practical tips and tricks, but they can also offer emotional support and inspiration. 

Plus, communicating with someone who truly understands the rollercoaster that is running a business can be therapeutic in its own right. So be bold about connecting with others who have walked in your shoes – you never know what valuable gems you might uncover. 

5. Celebrate Small Wins

My favorite advice is to celebrate daily efforts and small victories. 

Success isn’t just about the ultimate goal; it’s also about appreciating the journey and the incremental progress made each day.

But how have these women translated these strengths into tangible business success?

By listening. 

The level of sophistication that a startup achieves by answering insightful questions from venture capitalists is unparalleled. Even if you disagree with them, their questions force you to think critically. 

For Paola, it’s about maintaining unwavering confidence in her problem and vision. She explained, 

“I’m very confident about my problem. Solving the problem is inevitable. If I don’t have an answer, I will find it. And because my startup is moving forward, whether you invest or not, there’s an opportunity for you to be a part of it. It’s a chance for you to invest today and see the future take shape.”

Remember, less than 2% of VC funding goes to women and people of color, and changing that narrative requires actively seeking out the resources available. Paola urged entrepreneurs to embrace their resourcefulness but also unlearn it when necessary. She emphasized the need to become adept at articulating answers to investor questions, which allows for more informed, strategic conversations.

Defining Success 

So, what does success mean for these entrepreneurs? 

Max astutely observed that success isn’t merely about financial gains. “I thought success was all about the money, but I realized I feel successful because I built something that changed the world.”

Paola offered a broader perspective on success. 

“Success is about the day-to-day progress toward your dreams, not just the achievement of those dreams. It’s about celebrating efforts and results recognizing that effort is within your control. We should take the time to reflect on the enormous problems we’re solving and the impact we’re making.”

In a world where only 2% of VC funding goes to founders like them, Paola and Max’s journeys testify to the resilience, determination, and resourcefulness required to break barriers. 
Their experiences and advice are invaluable for any entrepreneur aspiring to make a dent in the fintech landscape and beyond. Use their pieces of wisdom to your advantage.