Amidst a venture capital landscape increasingly defined by the pursuit of monumental funding rounds and the fervent excitement surrounding artificial intelligence, Stacy Brown-Philpot, a seasoned executive with a distinguished career trajectory, has carved out a distinctive niche. Her firm, Cherryrock Capital, operates with a philosophy reminiscent of venture capital’s foundational principles, strategically deploying more modest Series A and B investments into companies founded by entrepreneurs frequently bypassed by larger, more mainstream investment entities. This measured, intentional approach stands in stark contrast to the rapid deployment strategies favored by many contemporary funds, signaling a deliberate return to a focus on fundamental value creation and long-term partnership.

The Shifting Tides of Venture Capital

The venture capital ecosystem has undergone significant transformations over the past few years, moving from an era of unprecedented exuberance to one marked by increased caution and selectivity. Following a period, particularly between 2019 and 2021, characterized by "mega-rounds" – funding tranches often exceeding $100 million – and an intense focus on scaling rapidly, the market began to recalibrate. The latter half of 2022 and all of 2023 saw a marked slowdown in deal volume and valuations, as rising interest rates, inflationary pressures, and geopolitical uncertainties prompted investors to prioritize profitability and sustainable growth over hyper-growth at any cost.

This market correction, while challenging for many startups, also revealed underlying structural inequities within the funding landscape. While capital continued to flow into established networks and founders with proven track records or those aligning with the latest technological hypes, such as generative AI, a persistent gap widened for early-to-mid-stage companies, particularly those led by entrepreneurs from diverse backgrounds or operating outside conventional Silicon Valley paradigms. This environment created a unique opportunity for funds willing to look beyond the immediate trends and identify untapped potential. Historically, venture capital itself began as a mechanism to fund innovative companies that traditional banks deemed too risky. Over decades, it evolved, experiencing boom-and-bust cycles, from the dot-com era to the mobile revolution, each reshaping its priorities and beneficiaries. Brown-Philpot’s strategy, in many ways, harks back to this original ethos, seeking out promising ventures that require more than just capital but also strategic guidance and patient growth.

Stacy Brown-Philpot’s Visionary Journey

Stacy Brown-Philpot’s journey to becoming a venture capitalist is one marked by strategic foresight and a deep understanding of both technology and operational leadership. Her ambition to enter the VC world dates back 25 years, a goal she articulated in her Stanford Business School essay. Before realizing this aspiration, she spent a decade at Google, gaining invaluable experience in scaling complex operations within a global technology giant. Her tenure culminated in a successful period as CEO of TaskRabbit, where she navigated the company through its acquisition by IKEA, demonstrating a keen ability to drive value and execute strategic exits. These experiences provided her with a unique perspective on the challenges and opportunities facing high-growth software companies.

The impetus for launching Cherryrock Capital solidified during her time on the investment committee for the SoftBank Opportunity Fund. This $100 million initiative, established in 2020, aimed to channel capital into businesses led by underserved entrepreneurs. Her involvement there illuminated a stark reality: a significant abundance of high-caliber founders and innovative companies were consistently being overlooked by the broader venture ecosystem. This firsthand observation reinforced her long-held belief in the untapped potential residing outside traditional investment pipelines. While SoftBank itself opted to divest from its diversity-focused fund in late 2023, selling it to its leadership team, Brown-Philpot saw not a reason to retreat, but an affirmation of the necessity of her mission. She doubled down, channeling her insights and commitment into the creation of Cherryrock Capital.

Cherryrock’s debut fund, which closed in February 2025, quickly amassed a pipeline of over 2,000 potential investments, underscoring the vast pool of founders seeking capital. The fund adopts a highly concentrated approach, aiming for a portfolio of 12 to 15 companies. This contrasts sharply with the strategy of many seed funds that might make dozens of smaller bets, or mega-funds that write nine-figure checks. Brown-Philpot, alongside co-founder Saydeah Howard, a veteran of the venture firm IVP with nine years of experience, has adopted a deliberate, unhurried pace. A year after the fund’s announcement, only five companies have received investments, reflecting a disciplined and thorough due diligence process—a methodology that echoes earlier generations of VCs who prioritized deep engagement over rapid deployment.

Redefining "Underinvested Entrepreneurs"

The term "underinvested entrepreneurs" is a carefully chosen descriptor by Brown-Philpot, reflecting a nuanced understanding of the venture capital landscape. It extends beyond simple demographic categories to encompass founders who, for various reasons—be it their background, geographic location, industry focus, or non-traditional educational paths—do not conform to the archetypal Silicon Valley founder profile. This deliberate framing is particularly pertinent in today’s social and political climate, where discussions around Diversity, Equity, and Inclusion (DEI) have become highly politicized.

Brown-Philpot remains steadfast and pragmatic regarding these dynamics. She emphasizes that Cherryrock Capital’s core mission is to generate substantial financial returns for its limited partners (LPs). The firm’s backing by prominent financial institutions such as JPMorgan, Bank of America, Goldman Sachs Asset Management, MassMutual, Top Tier Capital Partners, and Melinda Gates’s Pivotal Ventures, serves as a powerful testament to this return-centric philosophy. These LPs are sophisticated investors who demand performance, regardless of the socio-political context. The fact that some of these institutions have, in other contexts, reportedly scaled back explicit diversity pledges due to external pressures, further highlights Cherryrock’s ability to attract capital based on its investment thesis rather than solely on a DEI mandate. For Brown-Philpot, the identification of underinvested founders is not merely a social good; it is a strategic advantage, uncovering overlooked talent and market opportunities that others might miss. This approach underscores a neutral analytical commentary: focusing on talent and market opportunity, irrespective of origin, can naturally lead to a more diverse portfolio and potentially superior financial outcomes.

Navigating the Regulatory Landscape

The evolving regulatory environment, particularly in California, is creating a new dynamic that inadvertently favors firms like Cherryrock Capital. A new diversity reporting law (AB 551) in California mandates that venture capital firms with a nexus to the state disclose demographic data pertaining to the founding teams of their portfolio companies. The initial reporting deadline is set for April 2026. This legislation is significant because it emphasizes transparency and data collection rather than imposing quotas or specific mandates, thereby sidestepping some of the legal challenges faced by corporate diversity initiatives that involve preferential treatment.

For firms that have historically struggled with or actively avoided tracking diversity metrics, this new law presents a compliance challenge. However, for Cherryrock Capital, which inherently prioritizes and tracks investments in diverse founders as part of its core strategy, compliance is, as Brown-Philpot states, "table stakes." This positions Cherryrock in an unexpectedly advantageous position. By actively measuring and valuing diversity in its investment process, the firm is not only prepared for regulatory requirements but also potentially gains a competitive edge. This transparency can attract founders who seek investors aligned with their values and demonstrate a commitment to equitable opportunity. Brown-Philpot’s observation, "You accomplish what you measure," encapsulates the firm’s proactive approach to both investment and accountability.

Strategic Acumen and Portfolio Insights

Brown-Philpot’s strategic vision is further informed by her extensive involvement across various influential institutions. Her board memberships at HP, StockX, and Stanford University provide her with a panoramic view of enterprise buyers, consumer markets, and the emerging generation of entrepreneurs. These roles offer critical insights into industry trends, technological advancements, and the evolving concerns of future founders, particularly regarding the impact of artificial intelligence on employment and innovation.

Cherryrock’s early portfolio reflects this well-rounded perspective. One notable investment is Coactive AI, led by Cody Coleman, an MIT graduate with advanced degrees from MIT and Stanford in both philosophy and engineering. Coactive AI provides multimodal AI infrastructure tailored for the media and entertainment sector, an industry currently navigating complex issues surrounding AI-generated content and intellectual property. Cherryrock co-led Coactive AI’s Series B round alongside Emerson Collective, demonstrating confidence in its specialized technology and leadership.

Another key investment is Vitable Health, founded by Joseph Kitonga, a Thiel Fellow and Y Combinator alumnus. Based in Philadelphia, Vitable Health offers on-demand, primary care-based health insurance solutions to employers and hourly workers. This investment resonates deeply with Brown-Philpot’s prior experience as CEO of TaskRabbit, where she gained firsthand insight into the unique healthcare needs and challenges faced by the gig economy and hourly workforce. Kitonga exemplifies the type of founder Cherryrock seeks: "He does what he says he’s going to do," a testament to reliability and execution. Brown-Philpot’s initial investment in Vitable Health predates Cherryrock, having first backed the company at the seed stage through her involvement with the SoftBank Opportunity Fund, highlighting her long-standing conviction in the founder and the company’s mission.

A Pragmatic Outlook on Exits and the Future

Brown-Philpot maintains a refreshingly pragmatic perspective on investment exits, an often-glamorized aspect of venture capital. She candidly acknowledges the difficulty of achieving a public offering, stating, "It’s very difficult to go public. Most companies don’t go public, they do get acquired." This honest assessment stands in contrast to an industry that sometimes overpromises on IPO prospects. Her own experience with TaskRabbit’s acquisition by IKEA serves as a practical example of how the right acquisition can generate significant, lasting value for founders, employees, and investors alike. This perspective is particularly relevant in a market where IPO windows have been constrained, and strategic acquisitions often represent the most viable and valuable exit pathway.

As Cherryrock Capital continues its active deployment of capital into 2026, Brown-Philpot’s priority remains clear: identifying Series A and B companies that have achieved demonstrable product-market fit at scale. She empowers founders to define what "scale" means for their specific business, fostering an environment of tailored support rather than rigid metrics. While the broader venture ecosystem grapples with the future of diversity initiatives and the shifting sands of market sentiment, Brown-Philpot’s focus remains steadfast on the fundamental pursuit of exceptional founders and impactful innovations, wherever they may be found. Her personal philosophy, rooted in her Detroit upbringing, encapsulates this resilience: "Hard things are hard, but we know how to do hard things." This ethos not only defines her approach to venture capital but also offers a powerful message of determination for the entrepreneurs she champions.