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Venture Deals cover

Venture Deals

Brad Feld•2011

  1. Chappy's Book Notes•332 books

Venture Deals

Brad Feld•2011

Length
11h 4m•~304 pages
Read
Aug 29th - Sep 9th '23
Business StrategyEntrepreneurship
•

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.

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!

Summary

Venture financing is a game of economics and control, and the term sheet is where the rules get written. Pre-money valuation, option pools, liquidation preferences, and anti-dilution provisions determine who gets paid and how much — everything else is negotiation theater. The players range from micro VCs with under $15M to late-stage firms managing billions, each with different incentives and timelines. Smart founders come prepared with an option budget, understand the difference between participating and non-participating liquidation preferences, and know that creating competition among 3-6 VCs over months is the primary fundraising strategy. Board composition, protective provisions, and drag-along rights determine control — and control matters more than valuation when things go sideways.

Key Takeaways

  • Pre-money valuation, option pools, and liquidation preferences determine who gets paid
  • Participating vs non-participating liquidation preferences dramatically change founder outcomes
  • Come with an option budget listing anticipated hires to prevent inflated upfront option pools
  • Run a 3-6 month process with multiple VCs simultaneously
  • Never reveal who else you're talking to
  • Distinguish lead VCs (who move fast) from slow ones — lead investors set the terms
  • MDs/GPs actually invest; partners is a blanket junior term; associates do due diligence
  • Fund sizes range from micro VC (<$15M) to late-stage ($1B+) — each has different return expectations
  • Angels and super-angels operate differently from institutional VCs — know who you're dealing with
  • Control matters more than valuation when things go sideways
  • Drag-along rights, protective provisions, and board seats are the levers
  • Experienced startup lawyers are essential — cap their fees before negotiations begin
  • Delaware LLC, clean records, IP documentation — get the basics right before fundraising
  • Fundraising materials: elevator pitch, prototype, exec summary, pitch deck (10-20 slides)
  • Exude confidence; determine your ask based on time to MVP × burn rate
  • Full ratchet vs weighted average anti-dilution — understand the difference before signing
  • Pay-to-play provisions can protect or punish depending on future round dynamics
  • Redemption rights and dividends can quietly erode founder economics over time

Notes

1: The players

  • VC roles:
    • MD / GP: actually invest (founding)
    • Partner: junior, blanket term
    • Principal, director: need GP help
    • Associate: works for partner
    • Analysts: due diligence etc.
    • EIR: intros, due diligence, rights
  • Nomenclature:
    • Pre-seed, seed, A: early stage
    • B-D (1, 2 etc.): mid-stage
    • E+: late stage
  • Types of VC firms:
    • Micro VC: single GP, <$15M
    • Seed fund: 1st board member, <1$50M
    • Early stage: up to B, $100-300M
    • Mid stage / growth: B+, $200M-1B
    • Late stage: also PE, hedge funds, etc.
  • Angel investor: individuals
    • Super-angels: micro VC
  • Syndicate: collection of investors
    • Also all investors in your company
  • Lawyer: experienced, handles finer points
    • Skyrockets if lawyers don’t get along
    • Cap fee before starting negotiations
  • Accountant: only for later stage
  • Banker: only for late stage ($50M+)
  • Mentor: free help

2: Preparing for fundraising

  • Choose the right lawyer:
    • Experience, cost, comm style
    • Efficiency > cost
  • Delaware LLC
  • Be proactive about record keeping
  • IP: patents, copyright, trade secrets etc.

3: How to raise money

  • Exude confidence
  • Determine amount: time to MVP x burn rate
  • Fundraising materials:
    • Elevator pitch
    • Prototype or demo
    • Executive summary
    • Pitch deck (10-20 slides)
    • Business plan (30+ pages)
    • PPM, financial models
  • Due diligence
  • Finding VCs: use reviews from friends
    • Ask for references
    • Lead vs slow VCs
  • VCs have different funnels
  • Create competition: 3-6 months
    • Never say who you’re talking to

4: Overview of the term sheet

  • Term sheet: relationship with VC
  • Two factors: economics and control

5: Economic terms of the term sheet

  • Pre- and post- money valuation:
  • Fully diluted: all outstanding stock vested
  • Option pool: incentive for new hires
    • Early stage: usually 10-20%
    • “On issued”: not including already disbursed employee options
    • Come in with an option budget, listing anticipated hires and option grants, to prevent high upfront options pool
  • Warrant: option to buy series X stock at agreed upon price for certain period
    • Instead, negotiate lower pre-money valuation
    • Bridge loan: convertible debt investment, waiting for other investors
    • Convertible debt: converts into equity after next round is raised (20% disc.)
  • Early investors: help negotiate later rounds
  • Don’t take valuations personally
  • Liquidation preference: most important when sold for less than cost of assets
    • Eg. 1x preference for series A over common stock
    • No, full, capped participation: also participating in common stock
    • Liquidation preference overhang: price to make it to common stock
    • Stacked preferences: B before A
    • Blended preferences: A, B equivalent
    • Keep it simple in early rounds
    • Kick out: no participation once reasonable return via preferred shares
  • Pay to play: must invest pro rata in next round, else converted to common stock
    • Generally good to have
    • Waived during big rounds
  • Vesting: shares over period, with cliff
    • Unvested stocks → un-dilutive event
    • Can allow for purchasing invested stock at agreed price if leaving
    • Double vs single-trigger acc. vesting
  • Exercise period: can purchase stock outright within period (90 days, 10 years)
    • Good for employee retention
  • Anti-dilution: protection from down rounds
    • Ratchet-based: full, half, etc.
    • Weighted average: values of outstanding shares updated
    • Focus on minimizing impact

6: Control terms of the term sheet

  • Board of directors: planning department
    • Board observers: be weary
    • 5 person: 2 founders, 2 VC, 1 outside
  • Protective provisions: veto rights
    • Founders generally want to limit
    • Generally for monetary interests
    • Fight to vote as a single class
    • Drag-along agreement: common stock consent to series A vote
  • Conversion: convert to common stock
    • Automatic conversion: for IPO
    • Want lower threshold: prevent veto

7: Other terms of the term sheet

  • Dividends: 5-15%, largely unimportant
    • More important with lower return ratio
  • Redemption rights: guaranteed exit path for VCs due to fund lifespan
    • Adverse change redemption: bad
  • Conditions precedent to financing:
    • Approval by investors partnerships: VC still hasn’t formally approved deal
    • Rights offering to be completed by company: adds time + expense
    • Understand compensation, what happens if you get fired
  • Information rights: need transparency
  • Registration rights: don’t worry
  • Right of first refusal: pro rata right
    • No worries, but for big investors
  • Voting rights: standard
  • Restriction of sales: ROFR on common
    • Good thing for companies
  • Proprietary info and inventions agreement:
  • Co-sale agreement: try to negotiate down
  • Founder’s activities: 100% towards startup
  • IPO shares purchase: don’t worry about it
  • No-shop agreement: monogamy
    • Seek 30-60 day agreement
  • Indemnification: insurance policy
  • Assignment: VC transfer flexibility

8: Convertible debt

  • Convertible debt: loan → equity later round
  • Arguments against:
    • Used to be much cheaper, but standard term sheets (SAFE) negate
    • Discount may dissuade VCs
    • Valuation cap draws line in sand
    • Better seed, underpriced series A
  • The discount: incentive on top of interest
    • Discounted price on next round equity
    • 10-30%, sometimes non-static (90d)
  • Valuation cap: investor-friendly cap on price
    • Defers discussion to next round
    • Don’t disclose unless required by VC
  • Interest rate: lowest possible, usually 5-12%
  • Conversion mechanics: raise target, period
  • Conversion in sale: various methods
  • Warrant: option to purchase at certain price
    • Length, merger considerations, OID
    • Add complexity, cost
  • Pro rata: future round participation
  • Bridge round: with liquidation preference
  • CD risk: insolvency
  • Synthetic instruments: best of both
    • SAFE, KISS

9: The capitalization table

  • Founders, employee options, investors
  • PPS for convertible notes: 3 methods
  • Pre-money: most common
    • Most dilution for investors
  • Percentage-ownership: post-money
    • Most dilution for founder
  • Dollars-invested: compromise ↑

10: Crowdfunding

  • Product crowdfunding: presale campaign
  • Equity crowdfunding: Angel-list, security
    • Limits: accredited, investor, $1m
    • You set the terms
  • Token offering: ICO

11: Venture debt

  • Debt: short term, narrow, defined objective
    • Equity: long-term, flexible
  • Generally up to 25-50% of equity $$
    • Best when growth > profitability
  • Loan: beginning of a long-term partnership
  • Loan used as:
    • Performance insurance
    • Lower-cost runway extension
    • Funding for capital expenses
    • Short-term bridge to next round
  • Commercial loan: type determined by PSOR
    • Term loan: based on cash flow
    • Asset-based loan: collateral → cash
  • Venture debt: relies on access to VC
  • Growth capital term loan: ↑
    • 3-4 year repayment, 6-12m IO period
    • Interest-only period: ↑
  • Recurring revenue loan: based on ARR
  • Economic terms:
    • Interest rate: usually variable
    • Loan fees: when exceeding draw
    • Warrant:
      • Class of stock, strike price
      • Duration: push for shorter
    • Final payment, pre-payment terms
  • Amortization terms:
    • Draw period: request cash advances
    • Conditional IO extensions:
  • Control terms: based on performance
    • Affirmative, negative convenance
    • ↑ basically following the rules
    • Material adverse change: MAC clause
    • ↑ needed due to high risk
  • Reputation is critical
  • Watch for deal term drift
  • Technically defaulting on loan terms is ~ inevitable, so relationship is paramount

12: How VC funds work

  • Structure:
    • Management company: franchise
    • LP vehicle: fund containing LPs
    • General partnership: legal entity
  • LP agreement: agreement to fund amount
  • Capital call: get LP funds for investment
    • LPs have legal requirement to provide
  • Management fee: usually 1.5-2.5%
    • AUM generally matches compensation
  • Carry: usually 20-30% of fund profits
    • Carried interest, per-partner
  • 1-5% GP investment vs LPs
  • Clawback: past payment back to LPs
  • Commitment period: investing in fund
    • Generally 5 years
    • Zombie: no active fund, only manage
  • Investment term: how long can manage
    • Generally 10-12 years
  • Secondary sale: transfer of portfolio
  • Reserve: money saved for follow-on rounds
    • Can usually raise new round when 70% of previous fund is invested
  • Cross-fund investing:
    • Side fund: different structure
  • Understand VC’s partner dynamics
    • Is someone about to leave?
  • CVC: have a large corporation behind them
    • Typically higher valuations
    • More control: ROFR
    • Beware of conflict of interest
  • Strategic investors: one-offs

13: Negotiation tactics

  • What matters:
    • A good and fair result
    • Not killing relationship getting there
    • Understand deal you are striking
  • Game theory: multi-turn game
  • Prepare:
    • Know your price, what to concede
    • Study, know the other people
  • Ask for VC’s 3 most important factors:
    • Easier to call them out later
  • Be transparent and easygoing
  • BATNA: could be second best offer
  • Leverage:
    • Multiple offers (never disclose who)
    • Anchor terms: flexibility elsewhere
  • Go through terms in thoughtful order to maintain perspective, focus
  • Never make the first offer
  • Choose a great lawyer:
    • Ask around, always get references
    • Ask VC before and after

14: Raising money the right way

  • Pass the “beer test”: be a friend
  • Don’t ask for an NDA
  • Don’t ask for referrals after a no
    • Ask why the answer is no
  • Team > idea, patents / IP

15: Issues at different financing stages

  • Seed deal:
    • Establishes precedent
    • Important to have a good lead investor
  • Early stage:
    • Pay attention to establishing:
      • Liquidation preference
      • Protective provisions
  • Mid and late stages:
    • Board composition: don’t want to be dominated by investors
    • Clean deal > high valuation

16: Letters of intent: the other term sheet

  • LOI: first step in acquisition process
  • Big difference vs VC: fixed vs growing pie
  • Two components: price, structure
  • Escrow: for post-acquisition complexities
  • Working capital: should be zero
  • Earn out: at risk
  • Management retention pool:
  • Types of acquisition deals:
    • Asset deal: purchasing just assets
    • Stock deal: whole company
  • Know what you’re getting:
    • Cash > stock (pay attention to type)
  • Assumption of stock options:
    • Vesting of outstanding stock options
    • Cash, private, or public stock
  • Reps and warranties: promises by seller
    • Company or shareholder liability
  • Escrow: holdbacks - always decreases $$
    • Fraud, taxes, IP issues etc.
    • Buyers “often” try to overreach
  • NDA: in case of breakup of deal
    • Should be evenly bidirectional
  • Conditions to close: subject to…
    • Hints at attitude of buyer
  • No-shop clause:
  • Breakup fees: generally only public co’s
    • Reasonable if high risk
  • Registration rights: unregistered stock
  • Shareholder rep: don’t be one. Painful

17: How to engage an investment banker

  • IB: can help with M&A
  • Shopping: contact 50+ potential acquirers
  • Saves time, don’t have to be the bad guy
  • Want connected, experience, culture fit
  • Engagement letter:
    • Success fee: % of deal (90% of cost)
    • Retainer: monthly fee, reimbursement
    • Indemnification: ensure reasonable
    • Key person provision:
    • Fairness opinion:

18: Why do term sheets even exist?

  • No actual requirement for term sheet
  • Generally for LPs, auditing, legal
  • Watch out for misalignment
  • Transaction costs: lawyers, meetings, due diligence
  • Information asymmetry: agency dynamics
    • Eg. sell company at loss vs keep going
    • Think about provisions, eg. board seat

19: Legal things for entrepreneurs

  • IP: be very careful
    • Work for hire: ensure no issues
  • Patents: 20 year monopoly over use
    • Must file within first 12 months of use
    • Provisional, utility patent application
    • Seek guidance from patent council
  • Trademark: protects brand symbols
  • Employment issues: “at will”
    • Pre-bake severance terms
  • Corporate structure:
    • C corp: when you’re taking VC money
    • S corp: single tax structure
    • LLC: similar to ↑, but no equity
  • 409a valuation: fair price for stock
    • Employees are getting less (10 → 30%)
  • (83)b elections: tax for stocks vesting
  • Founders stock: common stock issued to founders at inception of company
    • Single, trouble trigger vesting
  • Consultants vs employees: min liability
  • Equity incentive plan:
    • Common stock with vesting