Winners Welcome Podcast, Episode 10 with Deepak Chhugani, Founder and CEO of Nuvocargo.

Deepak Chhugani, founder and CEO of Nuvocargo, has spent seven years trying to fix an industry everyone said couldn’t be automated. Now he thinks he’s finally found the moment it breaks.

Freight is a trillion-dollar market built on phone calls, PDFs, and manual work that nobody thought AI could touch. Nuvocargo just launched Nuvo AI, a fully agentic platform with more than a dozen specialized agents handling carrier negotiations, route planning, invoice auditing, and financial close, and Deepak joins Winners Welcome to explain what changed.

A two-time founder out of Y Combinator’s Winter 2018 batch, Deepak has raised over $85 million for Nuvocargo from QED Investors, NFX, and others. His philosophy has never been about selling software tools. It’s about owning outcomes, acting as the freight broker and customs broker so customers are measured on results, not another subscription.

In this conversation, Deepak talks through why keeping humans in the loop still matters even as AI takes over repetitive work, how Nuvocargo made its first acquisitions and what that taught him about blending cultures, and why he’s become one of the more prolific angel investors in his network, not for the returns, but for what it’s taught him about hiring, fundraising, and leadership. He also gets into what it actually means to build a “culture of builders” now that the cost of building has approached zero.

This episode of Winners Welcome is powered by Gunderson Dettmer, the number one law firm in venture capital globally.

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About The Winners Welcome Podcast

The Winners Welcome Podcast brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.

About Harlem Capital

Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.

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