What if the best venture opportunities are hiding in industries that software never touched?
Nicole Tommaso, Principal at Harlem Capital, joined VC Uncovered to break down the firm's contrarian approach to early-stage investing. She explains why she believes AI is unlocking markets that were completely closed to venture just a decade ago.
Harlem Capital backs underrepresented founders at the seed stage ($1M–$2.5M checks), but their edge isn't just who they back. It's how they think. Nicole explains why the firm evaluates a founder's childhood before their business plan, what a "high slope of learning" actually looks like, and why the most telling interview question is: what's the earliest entrepreneurial thing you remember doing?
She also unpacks Harlem's biggest investment theme right now: leapfrogging legacy industries. Truckers, tradespeople, and small business owners never adopted software. But they're adopting AI. And that generational handoff from Boomers to Millennials is cracking open markets that venture capital couldn't touch before.
Plus: why proprietary data is the last real moat, what metric is replacing ARR in the AI era, and the simple nighttime habit that keeps Nicole sharp in one of the most demanding jobs in venture.

In this episode:

• How Harlem Capital spots founders built to last
• The "leapfrog" thesis and why legacy industries are the new frontier
• What defensibility actually looks like when building costs near zero
• Why Harlem isn't backing down on diversity, even as the industry pulls away

This season is supported by SVB, Silicon Valley Bank, a division of First Citizens Bank. Member FDIC. This podcast is for informational purposes only and is not investment, financial, or legal advice.