nicole detommaso - harlem capital

“One check can trigger a ripple effect—from new hires to more diverse cap tables—impact in motion.”

Connect with Nicole

VC Uncovered's View

Amid a venture landscape often dominated by big funds and predictable pattern-matching, Nicole’s perspective is a breath of fresh air. She champions the “human” side of capital—spotting founders who exhibit determination and resourcefulness, regardless of traditional pedigree. In an industry long criticized for funding the same profiles and overlooking diverse talent, Nicole’s journey and investment philosophy underscore exactly why we launched VC Uncovered: to shine a light on bold, emerging managers who go beyond the status quo.

Her story resonates with our call for a new generation of nimble, daring VCs. Nicole experienced “no” after “no,” yet still carved her way into an industry that wasn’t always accessible. Today, she returns the favor by investing in early-stage founders who might not check the usual boxes but possess the grit to forge ahead. For those of us on the lookout for the next wave of innovation—where the most convenient fund size is the one that moves fast and bets on talent—her insights remind us that venture capital’s greatest impact often happens when it embraces non-obvious founders and unsexy markets. This is precisely the future we want to highlight: one where the right check, combined with genuine support, can unlock entire ecosystems of opportunity.

Meet Nicole

Q: You’re in a city, eating, drinking, and reading something. What is it?

A: In Cairo, eating a classic Egyptian dessert, Knafeh, and reading Matt Klein's newsletter, Zine, on cultural theory.

“If you have determination and resourcefulness, you can do anything.”

“At the earliest stage, the real risk is the founder. The data isn’t there, so I bet on the person.”

“One check can trigger a ripple effect—from new hires to more diverse cap tables—impact in motion.”

“They believe what you believe—so if you don’t believe it, neither will they.”

“We’re entering a massive generational turnover for family-owned businesses, and millennials aren’t afraid of tech.”

Original Responses (Lightly Edited for Clarity and Flow)

Background and Personal Journey

What experiences in your life or career have had the greatest influence on how you approach investing today?

I’ve been told “no” a lot in my life. People have said my goals were too ambitious or tried to undermine my abilities. Earlier on, especially as a first-generation college student at Columbia, I believed them. I felt less than, like I couldn’t compete. But I was lucky enough to land a junior banking role through an interviewer who basically said, “I see something in you—let’s give you a shot.” That changed the course of my life.

When I got there, I felt pressure to prove myself, but I ended up ranking at the top of my class and earning an early promotion. I realized there are two critical inputs to success: determination and resourcefulness. If you have both, you can do anything, regardless of who tells you “no.” That informs how I invest. If I see that determination and resourcefulness in a founder, I believe they’ll figure it out, even if I can’t predict what their company will look like in ten years.

What’s the best advice you’ve ever received, and how has it shaped your journey in venture capital?

Someone once told me: “People believe what you believe.” It was in the context of public speaking, but it applies to everything. Your inner self-talk—what you say you’re capable of—matters. If you truly believe in something, other people will believe it too. But if you don’t believe it yourself, no one else will either. That perspective has changed how I approach my career and my investments.

Do you see yourself staying in early-stage investing long term, or do you ever consider moving to later stages?

I’m a bit of an Excel junkie—I love data. But I also pride myself on having decent instincts that inform my early-stage bets. Data analysis can be taught, but gut instinct is harder to learn. Right now, I love the networking, the relationship-building, and the high conviction that early-stage investing demands. Never say never, but for now, I’m happiest where spreadsheets aren’t the entire story.

You publish a fantastic newsletter, and your content often targets aspiring VCs or those who want to break into the space. Why that focus?

Because I’ve been there, even with a finance background, I didn’t know early-stage VC existed. It’s such a network-driven industry, and if you don’t have those connections, it feels impossible. I was fortunate to get a shot at Harlem Capital, but I remember thinking, “Why isn’t there a resource out there to guide me?” I want to be that resource for others who don’t have the networks.

Philosophy and Insights

How would you describe your investment philosophy in a single sentence, and what led you to this approach?

Again, it comes down to determination and resourcefulness. If I see those traits in a founder, I’m willing to bet on them. My own path—being told “no” repeatedly yet finding a way—showed me that with those two qualities, you can exceed expectations. So if a founder has that drive, I believe they’ll figure out whatever pivot or challenge comes their way.

How do you approach risk in your investment strategy, and has your view on risk evolved?

My perspective has definitely evolved. I came from investment banking, which is heavily data-driven—models, unit economics, financial statements. But in early-stage VC, there’s often no meaningful data yet. Most assumptions at the pre-seed or seed stage will prove wrong over time.

I used to think the risk was about the product or the business model. Now, I believe the biggest risk is the founder. If they have that determination and resourcefulness, they’ll adapt. The data and traction at such an early stage are minimal, so my gut check on the founder matters far more than any spreadsheet.

How do you personally measure success in venture capital beyond financial returns?

For me, it’s about impact—both direct and indirect. The direct impact might be writing a million-dollar check to a founder who hasn’t traditionally had access to capital. The indirect impact is the ripple effect: that founder can hire a more diverse team, bring on diverse advisors, and ultimately create an inclusive cap table. Similarly, on my side, helping someone break into VC doesn’t just give them a job; it sets them on a path to mentor and invest in others.

Financial returns are, of course, essential, but I also want to see that domino effect of positive change in the ecosystem.

Anything else you’d like the world to know—about breaking into VC, working with founders, or future trends?

I’m particularly interested in university ecosystems. They’re talent hubs, especially for diverse folks and women, but not everyone feels included in campus entrepreneurship programs. I want to reach aspiring founders and VCs earlier, making this world less opaque. If I had known about VC and startup clubs at Columbia, I might have ventured into this space sooner. Talent is everywhere, but opportunity isn’t—universities are a prime place to bridge that gap.

Which emerging trends or technologies excite you most, and why do you believe they will shape the next era of innovation?

Everyone’s talking about AI, but I’m fascinated by the coming generational turnover in family-owned businesses. Millennials are inheriting or taking over companies from Boomers. The Boomers often ran things the old-school way; the new generation grew up with smartphones and technology, so they’re more open to software solutions. That means huge opportunities in SMB tech and vertical software—areas traditionally overlooked or called “unsexy.” As these businesses modernize, there’s massive potential for innovation.

What is a common misconception about the role of venture capitalists in fostering innovation?

Founders often give VCs a lot of flack, and sometimes it’s deserved. But VCs primarily provide a tool—capital. That’s essential for innovation. We also have the advantage of seeing patterns across many startups (n=100) instead of just one (n=1). When we offer suggestions, it’s often drawn from that broader perspective. Of course, bad VCs can negatively impact a business, but good ones can be genuinely helpful or at worst, neutral. Each party has a place in the ecosystem.