Reflecting on Four Years

As Bold Ventures marks its fourth anniversary in 2025, I find myself reflecting on our journey and the unexpected path that led us here. When I stepped away from Arabella Advisors at the pandemic’s onset, I had no blueprint for what Bold Ventures would become. My initial intention was simple: to create space for imagination, rest, and realignment. What I didn’t anticipate was how profoundly the pandemic would reshape my vision for the future and crystallize my values.

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That first year was one of exploration and discovery. Rather than rushing to build something new, I allowed myself to experiment, to identify what brought me genuine joy in the work, and to observe how others responded to different approaches. Through this process, I found myself building meaningful connections with others who shared a powerful conviction: that addressing capitalism’s extractive practices requires a fundamental reimagining of philanthropy, one centered on redistribution and repair.

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The true transformation began as our team took shape. Alysha, Crystal, and Melissa didn’t just embrace these ideas — they breathed life into them, translating abstract principles into tangible practices and operational frameworks. Together, we cultivated an organizational culture rooted in trust, autonomy, shared learning, and respect. It was their collective wisdom and courage that pushed me to be more explicit and public about these values, weaving them intentionally into every aspect of our work — from proposals to contracts, from client interactions to internal practices.

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What emerged was more than we could have imagined: a genuine receptiveness to our approach, proof that it was possible to practice philanthropy in a way that honored our values while bringing joy and meaning to both our team and our clients. This validation came not from compromise, but from staying true to our principles and allowing them to guide every decision.

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The past four years have tested these foundations as we’ve witnessed growing turbulence and resistance to equity-focused work. Yet it’s precisely these challenges that have proven the strength of our values-based approach. Each day, as we face new waves of opposition, these principles keep us grounded and steadily focused on our mission.

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Looking ahead, we harbor no illusions about the path forward. We expect the work to become more challenging, and we recognize that fewer people may feel safe engaging in these crucial conversations about equity and transformation. However, this reality only strengthens our resolve. We’re excited to grow our team thoughtfully, deepen our approach to this work, and embrace the opportunities that come from maintaining steady conviction in turbulent times.

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As we enter our fifth year, we do so with both clear-eyed realism about the challenges ahead and unwavering optimism about the power of our approach. Our commitment to transformative philanthropy, grounded in redistribution and repair, remains unshaken. If anything, the resistance we face only confirms that we’re pushing in the right direction, creating meaningful change in a system that desperately needs it.