A Place That Feels Like Freedom
Melissa Holloway Melissa Holloway

A Place That Feels Like Freedom

I went to the Vineyard searching for comfort and clarity. What I found instead was the power of expansion—of sisterhood, of community, of being sharpened for the next chapter of life. Sometimes the future reveals itself not in solitude, but in the laughter, rituals, and connections we share.

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Why I Continue to Invest in the DMV
Melissa Holloway Melissa Holloway

Why I Continue to Invest in the DMV

In a place shaped by both promise and pressure, investing in the DMV has never been about chasing trends—it’s about creating stability where it’s needed most.

As a Black woman, real estate investor, and advocate for community-rooted solutions, I believe housing should be more than a transaction. It should be a foundation—one that allows families to stay, grow, and thrive. Even in uncertain times, I keep showing up. Because the stakes aren’t abstract—they’re personal.

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Advancing Ownership at beatBread—One Deal at a Time
Melissa Holloway Melissa Holloway

Advancing Ownership at beatBread—One Deal at a Time

At beatBread, I wasn’t just building product—I was building pathways. My time there deepened my belief that when creators have real agency, the entire system shifts. Access, on their terms. That’s the future I signed up for.

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Tech Circle LA: Building Community, One Room at a Time
Melissa Holloway Melissa Holloway

Tech Circle LA: Building Community, One Room at a Time

Tech Circle at TGS LA is more than a meetup—it’s a movement. With partners like NSBE, TEC Leimert, STEM So(ul)cial, /dev/color, and others, we’ve created a space where community, culture, and technology come together on purpose.

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My Next Chapter: Black Venture Institute, Cohort 9
Melissa Holloway Melissa Holloway

My Next Chapter: Black Venture Institute, Cohort 9

I’m in a season of protecting my peace and saying yes with more intention. Applying to Black Venture Institute is part of that shift—an aligned, expansive step toward deepening my understanding of how capital moves, and how I want to move with it.

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AI for Us: Supporting Lola Vision Systems
Melissa Holloway Melissa Holloway

AI for Us: Supporting Lola Vision Systems

Earlier this year, I partnered with Lola Vision Systems to support their fundraising efforts—refining the story behind their tech, tightening their go-to-market, and helping translate a bold, complex vision into something investors could see clearly. Because when you’re building for high-stakes environments, clarity isn’t optional—it’s everything.

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Care Looks Like This: Intimate Dinners and Communal Healing
Melissa Holloway Melissa Holloway

Care Looks Like This: Intimate Dinners and Communal Healing

Last month, I hosted a dinner for women rooted in our shared Caribbean heritage—where the food was rich, the conversation deeper, and the care unmistakable. Because sometimes, “Did you eat?” is really just another way of asking, “Have you been cared for today?” What started as a meal became a moment of collective nourishment and quiet power.

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Founders, Don’t Build Alone: The Case for Ecosystem Thinking
Melissa Holloway Melissa Holloway

Founders, Don’t Build Alone: The Case for Ecosystem Thinking

Every founder needs a vision. But scaling that vision requires a network—mentors, capital, customers, and a system that supports the weight of ambition. I’ve seen too many brilliant ideas stall because they were built in isolation. Here's why ecosystem thinking isn’t optional—it’s essential.

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The Cost of Playing Small (And Why I Stopped)
Melissa Holloway Melissa Holloway

The Cost of Playing Small (And Why I Stopped)

Playing small feels safe… until it starts costing you the things that matter. A seat at the table. A shot at the deal. A future you actually believe in. This post is about the moment I stopped shrinking myself to make other people comfortable—and what happened when I finally moved with my full capacity.

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What Trading Taught Me About Product Strategy
Melissa Holloway Melissa Holloway

What Trading Taught Me About Product Strategy

Before I built products, I studied the market. Trading taught me pattern recognition, risk management, and the power of timing—skills I now use to make product decisions under pressure. Here's how day trading shaped the way I build, lead, and bet on what’s next.

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From Code to Concrete: Why I Invest in Housing
Melissa Holloway Melissa Holloway

From Code to Concrete: Why I Invest in Housing

I’ve spent my career building digital platforms. But some of the most important systems I’ve invested in… have walls, plumbing, and front porches. Here’s why stable housing for women and families of color in the DMV is a critical piece of my equity mission—and what I’ve learned building infrastructure offline.

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The Myth of Access: Why Inclusion Isn’t a Checkbox
Melissa Holloway Melissa Holloway

The Myth of Access: Why Inclusion Isn’t a Checkbox

Access isn’t about handing over the keys—it’s about redesigning the doors. In tech and venture, we love to talk about inclusion, but too often it stops at the language. True access requires intention, infrastructure, and a willingness to challenge the defaults. Here’s how I’ve learned to spot the difference between performative inclusion and the kind that actually shifts power.

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