The Secrets of Sand Hill Road
Venture Capital and How to Get It
Author: Scott Kupor
Length: 320 pages (~7 hour read)
Formats: Hardcover, Paperback, Kindle, Audible
Grab your copy of The Secrets of Sand Hill Road on Amazon here.
Why This Book Matters
If you’re considering raising venture capital—or just want to understand how VC firms actually operate—this is the playbook. Written by the managing partner of Andreessen Horowitz, The Secrets of Sand Hill Road demystifies how VCs think, what they look for, how deals are structured, and why power dynamics between founders and investors matter. It’s ideal for business owners who want to understand the game before stepping onto the field.
Core Idea
Venture capital isn’t just about money—it’s about long-term alignment. Kupor reveals that what separates successful VC-backed companies from those that flounder isn’t just a good idea, but a deep understanding of how venture funding actually works: the incentives, structures, timelines, and expectations that come with it. If you’re not prepared for that reality, the money can quickly become more of a burden than a blessing.
Key Tactics & How to Apply Them
1. Know Why (and If) You Should Raise VC
Venture capital is fuel for hypergrowth—not for lifestyle businesses.
How to apply: Only seek VC if you’re building a business with massive market potential, and you’re comfortable giving up equity, control, and optionality in exchange for speed and scale. Ask: “Do I want to build a unicorn—or do I want to keep control?”
2. Understand How VCs Make Money
VCs are managing other people’s money with expectations of 10X+ returns.
How to apply: Realize that VCs are betting on outliers. They’re not looking for safe businesses—they’re looking for home runs. Frame your pitch around how you can become one of those rare breakout successes.
3. Master the Term Sheet Basics
Seemingly small clauses can have huge long-term impact.
How to apply: Learn the implications of terms like liquidation preferences, board control, anti-dilution, and pro rata rights. Don’t just look at valuation—look at what happens if things don’t go as planned.
4. Build Relationships Before You Need Funding
The best VC deals come from trust built over time.
How to apply: Start connecting with investors 6–12 months before a fundraise. Share updates, show traction, and build rapport—so when you’re ready to raise, it’s not a cold pitch, it’s a warm relationship.
5. Choose the Right VC Partner, Not Just the Firm
It’s a long-term marriage, not a one-time transaction.
How to apply: Do founder references on the individual partner you’ll work with. Ask how they behave when things go sideways. Choose someone who adds real value and aligns with your style—not just someone who writes checks.
6. Plan for the Full Lifecycle of Funding
Raising capital is not a one-time event—it’s a series.
How to apply: Understand how early terms affect later rounds. Be realistic about how much you’ll need to raise in total, and how dilution and control will shift over time. Don’t over-optimize your Seed round and sabotage your Series B.
7. Build a Board That Works for You
Your board can be a strategic asset—or a drag.
How to apply: Use your board to fill strategic gaps and bring accountability—not to micromanage. Ensure independent seats are truly independent, and be intentional about who joins early.
Real-World Example
A B2B SaaS founder raised a Seed round with a high valuation and no liquidation preferences, thinking she got a great deal. But when growth stalled and she needed a bridge round, the lack of structure spooked new investors. Had she understood the expectations VCs operate under—and the signaling power of her earlier terms—she could have structured a healthier deal. After reading Secrets of Sand Hill Road, she renegotiated her cap table, brought on a stronger board, and raised a clean Series A aligned with long-term success.
When to Use This Book
You’re considering raising venture capital, but want to understand the tradeoffs
You’ve already raised a Seed round and are preparing for a Series A
You’re a founder who wants to avoid getting outmaneuvered at the board level
You’re building a high-growth startup and need to think three steps ahead
You want to learn how investors think—so you can pitch, negotiate, and partner more effectively
Grab your copy of The Secrets of Sand Hill Road on Amazon here.