New to Venture11 Maalis 2025

Ep 037 - Derek Chu, Principal at FirstMark

“The mentee knows the rules, but the mentor knows the exceptions”

Derek Chu, Principal at FirstMark, is a wealth of knowledge when it comes to startups. In this episode of New to Venture, he shares his thoughts on the art of consumer venture capital, what “great” looks like, and his career journey so far. Some of my new favorite quotes are sprinkled throughout the episode, so don’t miss out!

My key takeaways:

1️⃣ Understand the value of asymmetric opportunities. What actions/projects have low downside, but limitless upside? How can you live an exponential life versus a linear life?

2️⃣ Organic usage in the wild is a helpful litmus test for a viral consumer product. Think about a product’s frequency of use, density and gravity. These are the markings of a truly special consumer product.

3️⃣ If your gut is telling you something that you can’t quite explain, keep thinking—relentlessly. Clarity comes with sustained reflection. As Voltaire put it, “no problem can withstand the assault of sustained thinking.” When it comes to your opinions, "I don’t know" isn’t a final answer, it’s just the starting point.

Timestamps:

(00:00) - Introductions

(02:20) - Derek’s turning points

(06:54) - Shifting into early-stage investing and technology

(08:27) - What does “great” look and feel like?

(11:26) - Missing out on Warby Parker and Uber?

(15:59) - Investing in Posh

(23:02) - Deep dive into consumer investing

(28:50) - Discerning top talent to join the investing team

(32:18) - The VC apprenticeship model + mentorship

(40:26) - Highlights and lowlights

(44:43) - Ceremonial final Qs

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Jaksot(50)

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