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Hey there,
Been a while! Sorry for the extended absence, but I’ll be writing more regularly now.
If you want the TL;DR: start with Venture Deals and Secrets of Sand Hill Road to grok term-sheet kung-fu, layer on The Power Law for the big-picture madness of power-curves, then read VC: An American History and Creative Capital so you understand we didn’t invent this game yesterday, and finally season with a dash of data (Super Founders) and operator grit (High Growth Handbook).
Why read books when you can just vibe VC?
Great books compress decades of pattern-recognition into evenings of page-turning—exactly the kind of time-efficiency we celebrate when we refactor spaghetti code into two crisp functions. More importantly, the authors below have already paid the tuition in lost deals, 2× liquidation prefs, and reputational face-plants so you don’t have to.
1. Core Mechanics: term sheets, fund math, & LP management
Book | TL;DR |
|---|---|
Venture Deals – Brad Feld & Jason Mendelson | Your Rosetta Stone for every clause hiding in a term sheet—from liquidation prefs to drag-along rights—explained with the snark of two VCs who’ve seen every “clever” founder trick in the valley. |
Secrets of Sand Hill Road – Scott Kupor | An insider’s guide to how Sequoia-scale firms think about fund construction, ownership targets, and board dynamics—plus hard-earned advice for founders trying to navigate the partnership gauntlet. |
The Business of Venture Capital – Mahendra Ramsinghani | A soup-to-nuts manual on raising a fund, structuring deals, and engineering exits; particularly clutch for first-time managers who realize Excel macros alone won’t wow LPs. |
Side-note: Read these three, and you’ll stop confusing participating preferred with participation trophies. Your future associates will thank you.
2. History & Narrative: how we got here (and why it matters)
Book | Why it rocks |
|---|---|
The Power Law – Sebastian Mallaby | Sweeping reportage that shows how outsized winners, not “average returns,” define the asset class; after chapter three you’ll never look at portfolio construction the same way. |
VC: An American History – Tom Nicholas | A 200-year time-machine proving that MITI-era corporate labs and whaling-ship syndicates have more in common than you think—and that today’s SAFEs stand on some very old shoulders. |
Creative Capital – Spencer Ante | Meet Georges Doriot, the O.G. scholar capitalist who basically wrote the first investment memo; this is the origin story Marvel forgot to film. |
E-Boys – Randall Stross | A fly-on-the-wall narrative of Kleiner Perkins during the dot-com mania—equal parts hubris and hustle, and a cautionary tale for anyone stuffing their pipeline with me-too AI pitches. |
3. Data & Modern Insights: replacing gut-feel with spreadsheets (mostly)
Book | Key takeaway |
|---|---|
Super Founders – Ali Tamaseb | 300k data points demolish the myths around age, Ivy pedigrees, and solo founders; keep this handy when your partner says “we only back Stanford CS dropouts.” |
High Growth Handbook – Elad Gil | A pragmatic playbook for scaling a company from “cute seedling” to “redwood”—critical context for VCs who want to be value-add, not line-item overhead. |
4. Investor POV: writing checks (and living with the consequences)
Book | Why your LPs care |
|---|---|
Angel – Jason Calacanis | Street-level tactics for sourcing, evaluating, and syndicating early-stage bets—plus a reality check on spray-and-pray portfolio math. |
The Masters of Private Equity & Venture Capital – Finkel & Greisinger | Interviews with industry legends distilling decades of craft into quotable wisdom—think of it as office hours with the grey-beards. |
5. Honorable Mentions (a.k.a. “but wait, there’s more!”)
The Lean Startup – Eric Ries: still the best framework for validated learning; understanding it helps VCs separate iterative hustlers from PowerPoint pyromaniacs.
Zero to One – Peter Thiel & Blake Masters: not strictly a VC manual, but its monopoly-seeking mindset explains why founders—and the partners who chase them—end up aiming for 100×, not 3×.
How to read this stack without quitting your day job
Week-zero sprint: skim the chapter summaries of Venture Deals and Sand Hill Road—you’ll survive your next partner meeting.
Deep-work mornings: dedicate one pomodoro block per day to the narrative titles (Power Law, VC: An American History, etc.)—they read like thrillers anyway.
Saturday retros: apply frameworks from Super Founders or High Growth Handbook to a live deal—learning sticks when it costs (paper) money.
Quarterly calibration: revisit Angel and Masters to sanity-check whether your sourcing and decision filters are still sharp.
Final thoughts
Books won’t guarantee you a legendary markup—but they will keep you from cap-table face-plants, mis-priced secondaries, and Twitter rants about “evil VCs.” Read broadly, synthesize ruthlessly, and remember: our business is just applied learning under extreme uncertainty.
Happy reading, and may your IRR comp charts look like a hockey stick drawn by IKEA-trained graphical designers—minimalist, but undeniably up-and-to-the-right.
Until next time!
Signing off and signing zero checks,
SWEdonym
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