Two Filipino Founders Vow to Rewrite the Rules of the Venture Capital System
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Equity Angels Founder Katherine Winston and Twenty Five Ventures Founder Maximillian Diez
Founders tirelessly iterate, pivot, and push, hoping their idea will be the one to catch fire. But beneath the surface of this meritocratic façade lies a stark, measurable truth: the system is rigged.
For female founders and founders of color, the venture capital landscape is less a level playing field and more a Galton board, subtly tilted, with pegs unevenly spaced, ensuring that most beads — no matter how promising — never reach the winning slot.
This summer, however, a powerful initiative called "Power Forward" is aiming to recalibrate that board, championed by two visionary Filipino founders determined to level the playing field.
Maximillian “Max” Diez, General Partner at Twenty Five Ventures, speaks to this with piercing clarity in his newsletter, “Through the VC Looking Glass.” He describes how, from an outside perspective, the descent of a bead through a Galton board looks chaotic, random. "But the outcome isn’t chance," he argues. "It’s physics: gravity, angle, friction. Each bounce follows rules. The illusion of randomness arises from not being able to see the full path."
Startups, he insists, are no different. Founders succeed not by accident, but through resilience, adaptability, and resourcefulness. Yet, when the board is tilted by systemic bias, these inherent qualities often aren't enough to counteract the fundamental imbalance.
The data lays bare a tilted reality
Consider the dismal figures for women-led startups. In 2023, female-only founding teams received a paltry 2.3 percent of all U.S. VC dollars, according to PitchBook. That's a mere $6.7 billion compared with $241.9 billion for all-male founding teams. While female-founded companies represented 6.4 percent of deals, they captured only a fraction of the capital, with their average deal size ($5.2 million) significantly smaller than that of male-only founded companies ($11.7 million). The funding disparity becomes even more pronounced in later investment stages, a phenomenon sometimes referred to as the "leaky pipeline," where initial disparities compound throughout the startup growth journey.
For Black founders, the picture is even grimmer. In 2024, U.S. startups with Black founders or co-founders received just 0.4 percent of all funding, or approximately $730 million, according to Crunchbase data. This represents a multiyear low and a sharp decline from previous years. To put this in perspective, Crunchbase highlights that in 2021, Black-founded U.S. startups reeled in $4.5 billion, and $2.5 billion in 2022. While these were record-setting years, even then, the combined funding to Black founders barely exceeded 1 percent of the total U.S. startup funding. The current numbers reveal a profound and persistent underinvestment.
These statistics aren't abstract; they represent real people, real dreams, and real innovation stifled. And the rigging begins long before a founder ever steps into a VC's office. Take the concept of a "friends and family" round. For many aspiring entrepreneurs from privileged backgrounds, this initial funding stage – often between $50,000 and $500,000 – serves as a crucial launchpad, providing the capital to build a prototype, gather initial data, or simply stay afloat while pursuing their vision. It's a low-risk, low-cost way to get started, often bypassing the rigorous scrutiny of traditional venture capital.
What friends and family?
For a significant portion of underrepresented founders, the very idea of a "friends and family" round is far-fetched. How can you tap into a network of wealthy contacts when your family, like Katherine Winston's, immigrated from a "third-world country" for their very safety, arriving with little more than "two Balikbayan boxes each"? Winston, a seasoned entrepreneur and the founder of Equity Angels, shared her story of coming to the U.S. from the Philippines as a sixth grader.
For founders from underserved communities in America, or those like Winston who are first-generation immigrants, the "friends and family" network often means scraping together personal savings, if any, or relying on loved ones who are themselves struggling. This isn't about a lack of ambition or talent; it's about a fundamental difference in access to foundational capital and influential networks that can make or break an early-stage venture. As Techstars notes, for underrepresented founders, "bootstrapping" isn't a badge of honor, but "persevering through systemic obstacles hampering their business's growth." This slow growth then makes them less attractive to investors, creating a vicious, self-perpetuating cycle of underfunding.
The biases aren't always overt; often, they're unconscious, baked into the very fabric of how venture capitalists operate. Investors, predominantly white men, often gravitate towards founders who resemble them or come from similar backgrounds. As a McKinsey report highlighted, "A founder's affinity influences the willingness to invest. Having an identity that matches investors' expectations bestows a halo of 'expertise' upon the founder." This also means underrepresented founders are disproportionately developing relationships from cold outreach, rather than the warm introductions that are significantly more likely to lead to funding. When a founder's idea or business model doesn't align with "historical precedent" – meaning the typical successes seen by historically funded founders – investors may struggle to see its potential.
The venture capital ecosystem, for too long, has operated within a narrow paradigm, missing out on immense talent and groundbreaking ideas from diverse founders.
A more equitable system
But a new wave of founders and investors is not just calling out this rigged system; they're also actively working to dismantle it and rebuild it more equitably. Two Filipino founders, Katherine Winston and Max Diez, are at the forefront of this change, exemplified by their collaboration on the upcoming Power Forward summit.
Katherine “Kat” Winston, with her 25-year track record in tech, finance, real estate, and entertainment, is leveraging her extensive experience to empower diverse-led startups through Equity Angels. Co-founded with Kenya Burrell-VanWormer, Equity Angels isn't just another fund; it's a comprehensive ecosystem designed to transform how underrepresented founders access capital and opportunity. They offer accelerator programs, executive placement, and direct investor connections, aiming to expand opportunity in innovation while driving measurable returns.
Winston's own journey, from being a "FOB" to a successful entrepreneur gives her a unique perspective. She embodies the resilience she seeks to foster in others, drawing on what she calls "immigrant privilege" – not a negation of struggle, but an acknowledgment of the "unique advantages" forged by navigating different cultural contexts, overcoming hurdles, and benefiting from deep family support, tenacity, and a strong work ethic.
For her, this privilege translates into diverse perspectives and a determination to create inclusive environments, a philosophy evident through her life’s work from her early efforts to start an all-female, multicultural hip-hop dance team in high school and several initiatives over the past two decades to bridge the critical financing gap between investors and female founders, such as partnering with the New York City Mayor’s office to find funding for female entrepreneurs in film and media.
Maximillian Diez's Twenty Five Ventures is another powerful force in this evolving landscape. As General Partner, Diez is committed to investing in diverse-led companies that are powering the real estate and financial infrastructure. Before founding 25V, he played a pivotal role in scaling Movoto Holdings through a hyper-growth period, and was an early employee at Redfin, establishing their California market. His deep operational and investment experience provides a credible platform for his mission.
Diez's fund is explicit in its purpose: "We’re not here to fill a quota. We’re here to correct the board." They look "upstream," seeking out founders who "have done more with less, who’ve solved real problems without shortcuts." He contrasts this with the narrative of a founder like Adam Neumann, who "raised $350 million before launch—and another $100 million after," while "every Black founder combined raised less." For Diez, that's not about performance; it's about perspective.
Powering forward to correct the board
The upcoming Power Forward investment summit, a collaborative effort between Equity Angels and Twenty Five Ventures, stands as a tangible manifestation of their commitment to "correcting the board." Taking place on July 14th at Los Angeles' Fairmont Century Plaza, this groundbreaking event will bring together Silicon Valley, Pacific Northwest, and Hollywood-based investors with high-potential startups in sports, entertainment, and real estate technology. As Winston and Burrell-VanWormer stated, it's about efficiently connecting "investment expertise and entrepreneurial talent."
“This isn’t about checking boxes. It’s about identifying the best investment opportunities in high-growth markets. Through Power Forward, we’re creating a vital ecosystem where incredible innovation from founders who traditionally haven’t had access to capital are seen,” stated Winston in a recent Power Forward announcement.
The summit features MoviePass founder Stacy Spikes as the keynote speaker, an entrepreneur whose journey was recently chronicled in an HBO documentary and a bestselling book, Black Founder: The Hidden Power of Being an Outsider. The event will culminate in a high-stakes pitch competition where founders will vie for a significant investment through a dedicated Special Purpose Vehicle (SPV) worth six figures.
Notable tech and venture leaders participating include Patrick Lee (Rotten Tomatoes Co-Founder), Thai Randolph (HARTBEAT Co-Founder), Craig D'Cruze (COO of Inverted Ventures), Simon Chen (CEO of Arrival Home Loans), and angel investors Teresa Low and Dion Ridley. These leaders will share insights into navigating the entrepreneurial landscape, providing invaluable guidance to attendees.
The summit will proudly showcase 24 high-potential startups, demonstrating the breadth of innovation emerging from underrepresented communities. These include companies such as PairGap, Reeku, Convierge, Chambr, Goby Homes, ARKI, Free Agent, Sengo, Rely, Kahlab, Breadcrumb, Wauvea—and Filipino-led startups Fanded and Pivotal Build.
Outcomes aren't magic—they're math
The "illusion of randomness," as Diez terms it, "comforts the gatekeepers," allowing them to claim they're simply "picking winners" without interrogating who gets to the starting line first, or with what inherent advantages. But venture outcomes, like physics, follow patterns, and patterns can be rewritten.
Diez and Winston are not waiting for luck to surface new leaders. Instead, through initiatives like Power Forward, they are actively building systems and funds that find, fund, and keep underrepresented founders in the game. Their work is a testament to the idea that by understanding the "invisible forces and early friction" that shape a founder's journey, we can strategically "move the pins" on the Galton board, creating more equitable and, ultimately, more innovative outcomes for all.
The venture capital ecosystem, for too long, has operated within a narrow paradigm, missing out on immense talent and groundbreaking ideas from diverse founders. The work of pioneers like Katherine Winston and Maximillian Diez, culminating in events like the Power Forward summit, represents a critical shift. It's a call to arms for the industry to move beyond superficial diversity initiatives and address the fundamental structural inequities. Because in venture, as in physics, outcomes aren't magic. They're math. And it's time we all started doing the calculations out loud, demanding a system that truly backs the best, regardless of background.
Editor’s Note: This article was sent as part of the promo for Pitch Forward.
Danica Coronacion Mock is a storyteller and freelance writer with a diverse background in sports, entertainment, technology, and real estate. At I AM Sports and Entertainment and Filipina on the Rise, she was crucial in content creation and producing video pieces. Danica has also held key people operations roles at startups Ro and Choco. Currently, she serves as EA to the EVP and CPO at InterDigital and Chief of Staff at Equity Angels, promoting diversity in innovation.
