EP 162 - Alex Oppenheimer: The Secret Investors Use Before Writing the First Check

Beginner's Mind

Here’s the harsh truth: If your business model can’t survive a spreadsheet, it won’t survive the market.

Every year, ambitious founders pour months into product, pitch, and brand—yet the single biggest reason startups die isn’t funding, it’s flawed modeling.

What are the four variables investors use to spot winners before anyone else?

In this episode, investor and hands-on builder Alex Oppenheimer (Founder & GP at Verissimo Ventures, ex-Facebook IPO, ex-NEA, Monday.com advisor) reveals why most startup advice misses the point—and how the best founders reverse-engineer success long before a single euro is raised.

🎧 Watch now to learn:
1️⃣ The business model simulation Alex uses to kill (or greenlight) a deal in under an hour
2️⃣ The one thing top VCs always ask founders—but almost nobody prepares for
3️⃣ Why a founder’s “calling” is more important than their credentials
4️⃣ How to avoid the European trap of ignoring leverage and failing to scale
5️⃣ The subtle mindset shift that separates bold investors from the herd—and how to apply it to your own company

👤 About Alex Oppenheimer
Stanford-trained engineer, ex-Morgan Stanley tech banker, NEA Series A investor, Monday.com operator, and now founder of Verissimo Ventures—a fund that bets on weird tech and next-gen software models in Israel, the US, and Europe.

💬 Quotes That Might Change How You Think:
(00:59:00) “If I don't build this, nobody else will—that’s the founder’s true calling.”
(01:12:45) “How can you know what data to collect if you don’t know the model?”
(01:22:36) “The real job of an investor is helping great founders not mess it up.”

🧭 Timestamps to Explore:
(00:04:00) Quitting Corporate Venture—The Decision That Changed Everything
(00:11:50) What Business Modeling Is (and Isn’t)
(00:18:30) Trusting the Founder Over the Deck
(00:24:40) Venture Capital and the Power of Naivete
(00:34:03) Inside the Facebook IPO Data Room
(00:44:38) Lessons from Betting on Outliers
(00:49:48) Leaving NEA to Build Israel’s Next Scaleups
(01:02:32) From Frustration to Founding a Venture Fund
(01:10:57) Why Business Modeling Remains a Blind Spot
(01:14:09) Redefining Value Investing in Venture Capital
(01:15:50) Decoding Value with Core Variables
(01:22:36) Helping Founders Avoid Unnecessary Pitfalls Early

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