The summary and key takeaways below are auto-generated. I ran an AI pass based strictly on my handwritten notes for this book. I haven't done my own pass over them yet.
How I read and take notes I read a book once and take handwritten notes as I go, then leave them alone. Weeks or months later I come back and write the key points and summary from those notes.
The delay is on purpose. Having to rebuild a book out of my own notes does far more for my recall than a second read-through would.
This one has only gotten as far as the AI pass. I'll come back and redo the takeaways and summary myself soon!
Kupor (a16z COO) provides a practical guide to VC mechanics from both sides of the table. VC invests just 0.4% of US GDP but accounts for 42% of IPOs, 63% of new market cap, 85% of R&D spend, and basically all net new jobs since 1977. The book demystifies fund structure (LPs, GPs, carry, hurdle rates), term sheets , and what VCs actually look for.
Key thesis: VC follows a power law distribution – it's not a good asset class in aggregate, but the best funds generate outlier returns. A good VC batting average is .500. Goal: generate 2.5-3x net returns, which requires 3-4x gross returns. For founders, the pitch objective is convincing VCs your company has the chance to be a 100x+ outlier , not just a solid business.
42% of all US IPOs were venture backed
63% of new market cap
85% of R&D spend
Basically all of net new jobs since ‘77
Invests only 0.4% of US GDP, for all of ↑
1: Born in the bubble
Dot com bubble
900 IPOs
Avg 4y to public, now 10+
PE ratio of 175+
Dropped 80%+
Loudcloud LBO vs IPO
↑ to Opsware → HP acquisition
1970s was start of VC
Capital was scarce, dominated by a few players
Big changes:
Cloud computing slashed startup cost
YC 2005:
Educated
Cracked open VC black box
Created community
a16z: capital becoming commodity, need to provide value
Conviction in product-Eng CEOs
↑ lack other skills
So build a network of institutions
2: So really, what is VC?
Useful when loans don’t work
↑ no ownership, must be paid back
VC takes “permanent capital” (equity)
Better choice when:
Not expecting to generate near-term cash flow
Are very risky
Have long illiquidity periods
Convertible debt: non-permanent into permanent
VC is not a good asset class
VC is a power law distribution
VC positive signal flywheel
Shorthand for informing judgement
VC is largely zero-sum
Accredited + qualified investor gate-keep
Good VC batting average .500
Better measure: at bats per home run
Goal: generate 2.5-3x net returns → need to generate 3-4x gross returns
3: How early stage VCs decide
People and team
Motivations: product-first vs company-first company
Founder-market fit
Need to be able to sell / tell a story
Egomaniacal: have to be party delusional
Product
Testing product fitness in market
Evaluating “idea maze”
Strong opinions weakly held
Vitamins vs aspirin
Market size
Is the “so what” question - doesn’t matter unless market is big
Hard to estimate (eg. Airbnb growing the market)
4: What are LPs?
Original VC industry: whaling
LPs generally expect 5-8% extra IRR from VC vs S&P500 due to illiquidity
Types of LPs
FoFs have LPs too
Yale endowment is the benchmark model now (Swenson post-‘85)
Usually 4-6.5% given to school/yr
20% domestic public equity
15% foreign public equity
10% hedge funds
51% Illiquid assets (less efficient markets)
15% buyout funds (PE)
16% VC (77% IRR)
20% hedge against unexpected inflation
7.5% oil and timber commodity
12.5% real estate
7.2% hedge against deflation
4.9% bonds (5% IRR)
2% cash
Know the timeline of the fund investing (10y)
5: How LPs team up with VCs
“Limited” partner / role: (passive)
Limited governance:
No say in investments, “blind pool”
Limited say on exit, return of capital
Limited liability
General partner: assume all risk
Pass through entity: no corporate (double) taxing
LPA: LP agreement
LP cash flow J curve
Methods for valuing companies
Last round waterfall
Comparable company analysis
Public company with revenue multiple + DLOM
Option pricing model (OPM)
Set of call options with strike prices
Clawback when over-distributing to self
Recycling: past wins re-invested
GP commitment
Hurdle rate: can’t take carry unless return is above this # (eg. 8%)
Preferred returns: carry only after above the hurdle rate
Careful of misaligned incentives: eg. quick exit to clear hurdle rate
Additional LPA terms:
Investment domain (eg. industry, geography, round, asset class)
Primarily to prevent style drift
GP co-investment
Substantially all efforts
Suspension → divorce if not met
Applies to key men
EPA: equity partners agreement
Ownership and governance
Vesting
Indemnification
6: Forming your startup
C corp vs pass through (eg VCs)
VCs typically avoid investing in pass through corps
C corps: equity, shareholder classes
Equity = long-term incentive
Vesting
Blanket transfer restriction: prevent sell equity without company consent
More often ROFR for company
Employee option pools
Option + exercise price
Incentive stock options (ISOs) vs non-qualified options
IPOs down by 50%, now often 10 yrs
Causes:
Higher cost due to regulation → more revenue to amortize
Efficiency rules disproportionately effect smaller companies (liquidity)
Mutual funds are bigger, and thus like bigger companies (5x since 2000)
There are alternative forms of private financing
There’s too much public company pressure (eg. hostile takeovers)
7: Raising money from a VC
Know what you want, how much, and why
Benchmark market size: $xxxM business in the next 7-10 years
Though some small VCs target acquisition exits → go smaller
Are you ready to play by the rules?
Raise enough money to meet milestones to raise the next round (12-24 mo)
Eg. $3-5M ARR for series B
Too much $$ → risk of lack of focus
Higher valuation → higher risk of flat or down round
Need to create competition for round
Too high valuation risks ↑
Employee morale + momentum
8: The art of the pitch
Warm intros from angels, legal
↑ acts as screening criteria
Objective: convince the VC that your company has the chance to be a 100x+ outlier
Paint the market size picture
Market vision
Network effects
Team: why you?
Experience / learning (vs failure)
CEO skills
Storytelling
Product
GTM
Show that you’re the master of your domain: conviction (don’t cave to VC suggestions)
Milestones for next round
9: Term sheets: economics
Aggregate proceeds: debt must often convert to equity
Valuation
Comparable company analysis
Discounted cash flow analysis
Beware of fund cycle and VC’s ability to follow on (show of faith)
VC valuation
“What do I need to believe?” analysis
Capitalization: forecast hiring requirements
Dividends
Liquidation preference: who gets their money back during certain circumstances
Helps to align interests across rounds
Participating: get X back, then convert to common stock to participate in proceeds
Preference order: seniority vs pari passu
Redemption
Conversion / auto-conversion:
Can have 2-3+ classes, but risky splitting incentives
Anti-dilution: safety from down rounds
Broad-based weighted average
Full ratchet
Voting rights
2: Term sheets: governance
Board of directors:
Hire / fire CEO
Ruling from the grave / dead hand control: CEO removed but still on board
First 3 should be CEO, VC (representing preferred shareholders), independent
Protective provision:
Delaware chosen because it has the most developed set of provisions and governance rights
Protection against economic value of investment
Registration rights: IPO stuff
Pro rata: generally above ownership threshold
Stock restriction
ROFR: can control who owns shares
Co-sale: right of all owners to sell at that price on a pro rata basis
Drag along: prevents tyranny of the minority in sales
D&O insurance
Vesting:
Standard 4y with 1y cliff
Post-termination exercise period 90d
Double trigger acceleration: acquisition + acquirer end of employment
Employee and consultant agreement
No-shop: 30d tie-up, even though two-way non-binding
Takeaway: be forward-thinking and align long-term incentives
11: Which deal is better?
Cap table
Tradeoff between current known dilution and future round dilution
Maintain momentum
Must consider both economic and governance terms
12: Board members
AVC’s have dual fiduciary responsibility
CEO vs board info gap (full-time vs advisory)
If the board is getting too hands on, ask why (eg. losing faith in your abilities)
Pre-flight major decisions with individual board members early
409(a) valuation
Should never overreach and influence product strategy (not enough context)
Gentle nudge back on task
Set expectations up front (1-1s)
13: In Trados we trust
Duty of confidentiality quagmire: on two boards with competing products - must leave, reassign, or recuse
Business judgement rule (BJR) : courts are loathed to second guess a board decision as long as duty of care
Keep good meeting minutes
Entire fairness : opposite of ↑, majority not disinterested → burden of proof on the board
↑ determined by assessing conflict of interest
Lesson: if you have liquidation preference during an acquisition you’re probably conflicted, so beware
Assume most VC board members are conflicted
Most importantly, need to recognize risk of potential CoI clearly and take action
14: Difficult financings
“We are where we are, and something needs to change”
Reducing liquidation preferences:
Pull up: carry forward some of LQP
Reverse split
Insider rounds
Management incentive plan (MIP)
Warren notice: must give 60d notice of shutting down business
Faltering company exception: if fundraising and would degrade ability
15: Exits
Get to know potential acquirers early
Make sure you have multiple suitors
Aspects of deal
Acquisition price
Cash vs stock
Vesting acceleration
Additional grants to key employees
Generally want 90%+ of votes in favor of the acquisition
Escrow (10-15%), term (12-18 mo)
Indemnification
Exclusivity period (usually 30-60d)
Revlon duty: must explore all options to get the best price
How will the acquired company be incorporated?
Why IPO?
Raising capital
Branding
Selling stock
Customer credibility
M&A currency
The IPO process
Conclusion: the world is flat
Capital is more abundant now
Lower cost to start a company
More seed-stage funds
It’s easier for startups to win
2 important financing trends;
All-stage VCs
More non-traditional sources of growth capital (non-IPO)
Private > public returns
The end of VC?
↑ democratization