Chapter 6 · Leading Deals

Ownership, Pricing & the Fund-Returner Test

The lead sets the price, and the price sets the ownership. That ownership, after years of dilution, decides whether success at this company can matter to the fund at all. This module covers the math a lead should run before offering a term sheet: entry ownership, dilution to exit, the exit value needed to return the fund, and what reserving for follow-ons buys. It also covers the judgment around it: when to hold the line on price, and when discipline just means losing the best companies.

Price is what you pay; ownership is what you get

Two term sheets can offer the same headline valuation and produce very different outcomes. What matters to the fund is ownership: the percentage of the company your check buys, and how much of it survives to exit.

At entry, ownership is your investment divided by the post-money valuation. $3M into a round at a $25M post-money buys 12%.

That number then shrinks. Every later round issues new shares, and unless you buy more, your percentage falls.

The fund-returner test

Module 1.3 explained why a fund needs a few companies that each return the whole fund. The lead's version of that idea is a single question: if this company works, can it return the fund?

The math: exit value needed = fund size ÷ ownership at exit.

Worked example — a $100M fund, a $3M seed check

Setup: a $100M fund invests $3M at a $25M post-money, so it owns 12% at entry. Assume three more rounds before exit, each diluting existing holders by 20%. Real dilution varies by company and market; 15-25% a round is a common planning assumption. Figures are gross proceeds to the fund, before fees and carry.

Without follow-ons:

Ownership
At entry12.0%
After three rounds (12% × 0.8 × 0.8 × 0.8)6.1%
Exit value needed to return $100Mabout $1.63B

With pro rata in the next round (buying enough to hold 12% through the Series A, then no further follow-ons):

Ownership
After the Series A12.0%
After two more rounds (12% × 0.8 × 0.8)7.7%
Exit value needed to return $100Mabout $1.30B

Following on lowers the bar by more than $300M of exit value. It also costs more capital, which has to come from reserves, and it raises your total investment in the company, so the same exit is a lower multiple on what you put in.

Run this before the term sheet, not after. If the answer is an exit value no company in this market has reached, then the ownership is too low, the round is priced too high, or the fund isn't the right home for the deal.

When to hold the line on price

Price discipline protects the math above. The case for flexing: in a power-law business, the cost of missing a great company is far bigger than the cost of overpaying for one. Both are true, so the question is which situation you're in.

  • Hold when the company is good but not exceptional, when the price assumes things going right that haven't happened yet, or when the resulting ownership fails the fund-returner test.
  • Flex when you'd be genuinely surprised if this weren't one of the best companies you see this year, and the ownership still clears the test at the higher price.

"This one is the exception" is how funds end up owning too little of too many companies. Keep a record of what you passed on over price and what became of those companies. It's the only honest way to calibrate.

Structure is part of the price

The headline valuation isn't the whole price. The option pool (sized pre-money, it comes out of the founders' share, not yours; module 3.1), the liquidation preference, pro rata rights and board composition all change what you're really paying and what you're really getting. A clean, market-standard structure at a slightly higher price is often worth more than a complicated one at a lower price, because it doesn't poison the next round.

Reserves: decide at the start

Many funds hold back something like half the fund for follow-ons. The lead should propose a reserve for each company at the time of the first investment, not when the next round arrives. That's what makes the fund-returner test real: the with-follow-ons column above only exists if the money is set aside. Module 5.2 covers follow-on decisions; the portfolio construction resources below cover how funds set reserve ratios.

Small ownership can work, in a different strategy

The math above assumes a concentrated fund chasing meaningful ownership. Some pre-seed and seed funds deliberately own less of more companies and rely on breadth to catch outliers. The math still has to close; it just closes differently. Know which strategy your fund is running before you argue about ownership in IC.

What this means for you

Bring the fund-returner math to every IC, even when nobody asks for it. It turns "I love this company" into a claim the partnership can test, and it's the fastest way to show you think about the fund's outcome, not just the deal's.

Resources

ArticleKauffman Fellows Journal

Venture Fund Portfolio Construction

A clear practitioner treatment of check sizes, ownership targets and reserve ratios.

ArticleAngelList Education Center

Portfolio Construction

Check sizes, company count and reserves, from a platform that sees thousands of funds.

ArticleFred Wilson (AVC)

Valuation and Option Pool

Option pool sizing is where the headline price and the real price diverge. Read this before you negotiate either.

ArticleACQ2 (Acquired) with Charles Hudson

Everything you need to know about Pre-Seed

Charles Hudson of Precursor Ventures on how pre-seed investing works, from a firm built on small checks into many companies.

Go Deeper

ArticleTactyc

Tactyc

Modelling tools for what this module does by hand: ownership, reserves and outcomes across a whole portfolio.