What separates the top 1% of venture capitalists from the rest? For Roger Ehrenberg, Managing Partner at Eberg Capital, it’s the ability — and the appetite — to invest before the crowd, before the product is built, and before there’s even proof of concept. In a recent episode of the Skin in the Game VC podcast, Roger joined Tom Wallace and Saxon Baum to share how he turned a late-career pivot into one of the most impressive track records in early-stage venture capital.

Roger didn’t come from the startup world. He spent nearly two decades on Wall Street, running billion-dollar trading desks at Citi and Deutsche Bank. From the outside, it looked like a career anyone would want — but for Roger, it had run its course. Tired of internal politics and craving something more entrepreneurial, he walked away. Around the same time, he’d been dabbling in angel investing on the side. That small experiment — backing builders before product-market fit — quickly turned into a full-time obsession.

He began writing a blog, Information Arbitrage, to share his thinking publicly. The blog gained traction. Founders started reaching out. Other investors began to follow his thesis. At a time when the idea of a “New York tech ecosystem” was almost laughable, Roger had the clarity to see where it could go — and the conviction to act. By early 2010, he scraped together a $17 million first close. That first fund would eventually land at $50 million, and IA Ventures was born.

But the money was only part of the story. What set Roger apart then — and still does — is how early he’s willing to go. He prefers backing companies before the market even knows they exist. In fact, he often writes the first check before there’s a line of code written. This isn’t blind optimism. It’s founder-first investing grounded in deep research and sharp intuition.

Roger’s track record speaks for itself. He was an early backer of The Trade Desk when it was just a deck. He seeded Datadog, TubeMogul, and multiple other companies before they became category leaders. The common thread? Founders who could not only see the future but build their way into it. To Roger, great founders share something intangible: what he calls “aesthetic and empathy.”

“Great founders understand where their product stops and where the customer starts,” he said. That could mean designing APIs that developers love or building consumer apps that feel inevitable. Either way, the best founders have an intuitive sense of product, user behavior, and market timing. Roger knows how to find them — or maybe, they know how to find him. That’s the power of publishing, he says. His blog didn’t just clarify his thesis — it attracted the right people. It helped him raise a fund when few believed in early-stage investing outside Silicon Valley.

Since then, IA Ventures has grown to four funds and backed dozens of successful startups. Roger has since passed the torch to his partners and launched his next chapter: Eberg Capital. Now, he invests alongside his sons in a new wave of innovation — spanning sports, media, entertainment, and the evolving world of fandom.

But whether he’s backing a Marlins ownership stake, investing in Formula 1, or writing angel checks to creator economy startups, one thing hasn’t changed: Roger Ehrenberg still goes early. He still backs founders before the world sees their potential. And more often than not, he’s right.

Listen to the full episode with Roger Ehrenberg now.

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