Venture Capital interview preparation

Questions

100

Traced to a firm

31

Firms

12

Updated

September 2026

Asked at

All firmsGeneral Atlantic9Insight Partners7Silver Lake6Vista Equity Partners4Bessemer Venture Partners3ACAccel2Advent International2Battery Ventures2Andreessen Horowitz1Coatue Management1Sequoia Capital1WPWarburg Pincus1

Topic

All topicsSourcing and deal flow5Market sizing and estimation8Founders and teams5Unit economics and cohorts11Term sheets12Cap table and dilution7Early-stage valuation7Portfolio construction6Board and governance4Down rounds and secondaries4Exits and liquidity4Fund economics5Sector theses and markets6India venture market6Fit and motivation10

Level

AnyCoreIntermediateHard

Type

AnyTechnicalFitCaseMarket viewBrainteaser

1. 042Build me a cap table from founding through Series B.Cap table and dilutionHardtechnicalEarly-stage VCGrowth equity

   Say this

   Work in percentages, round by round, and apply each round's dilution to everyone who came before. Two founders start at 100, a seed round takes 20, a Series A takes 22, a Series B takes 18, and the founders end up around 45 percent before you account for the option pool, or closer to 38 after it.

   Then walk it

   1. Founding: two founders, 50/50, 10 million shares, all common, four-year vesting with a one-year cliff.
   2. Seed: $3m at a $12m post-money, so 25 percent to the seed investor, plus a 10 percent pool established out of the pre-money. Founders go from 100 to about 65 percent between the two. The pool coming from the pre-money is why 100 minus 25 does not equal the founders' number.
   3. Series A: $12m at a $60m post-money, so 20 percent to the new investor, and a pool top-up to 12 percent. Everyone pre-existing is diluted by roughly 22 percent including the top-up, so the founders go from 65 to about 51.
   4. Series B: $30m at $170m post-money, 17.6 percent to the new lead, plus a small pool top-up. Founders land around 41 to 42 percent, and if the seed fund did not follow on it is down from 25 to about 16.
   5. The rule to say out loud, because it is the whole mechanic: each round's dilution applies multiplicatively to every prior holder. Three rounds at 20 percent each leaves you with 0.8 cubed, which is 51 percent, not 40. Candidates subtract when they should multiply.
   6. Then the two real-world complications I would flag. One, the pool top-up at each round comes out of the pre-money, so the founders fund the hires the new investor wants. Two, if there are SAFEs or notes outstanding, they convert first and they convert at their caps, so the Series A investor's own percentage is diluted by paper they did not price.

   Where candidates lose it

   Subtracting percentages instead of multiplying. Three 20 percent rounds do not take you to 40 percent. And forgetting the option pool at each round — it is typically 10 to 15 percent, it comes from the pre-money, and leaving it out makes the founders look 10 points richer than they are.

   Expect next

   • Where did the option pool come from in each round?
   • How much should the founders own at Series B for this to be fundable?
   • What happens to the seed investor if they do not follow on?
2. 043What is the option pool shuffle, and who actually pays for it?Cap table and dilutionHardtechnicalEarly-stage VCSeed funds

   Say this

   The pool shuffle is putting the new option pool into the pre-money valuation, so the founders are diluted by it and the incoming investor is not. The founders pay for every hire the new investor says the company needs, and it lowers the effective price the investor pays without touching the headline number.

   Then walk it

   1. Mechanically: the term sheet says a $20m pre-money and a 15 percent post-closing option pool. The pool is created before the money goes in, so the pre-money share count expands, and the effective pre-money for the existing holders is lower than $20m.
   2. Run the number, because that is the answer. $20m pre, $5m in, so a $25m post and 20 percent to the investor. Now carve a 15 percent pool out of the pre-money: the founders' share of the pre-money company drops from 100 to 81 percent of what it was. The effective pre-money on the founders' existing equity is closer to $16.25m than $20m. That is an 19 percent price cut disguised as a governance term.
   3. Who pays: existing holders only — founders, seed investors, anyone on the cap table before the round. The new investor's 20 percent is measured after the pool exists, so they are untouched by it.
   4. Why investors do it: it is a real economic term that never appears in the headline, so a founder optimising for a press-release valuation gives it away without noticing. Two term sheets at $20m pre with a 10 percent and an 18 percent pool are materially different prices.
   5. How founders should push back, and this is the answer that shows you know the market: build a hiring plan. Argue for the pool the next eighteen months of hiring actually requires, not a round number. If you can show that 9 percent covers the plan, a 15 percent ask is the investor taking price. Alternatively ask for the pool to be split, part pre-money and part post-money.
   6. The nuance worth adding: the pool is not waste. Unissued options revert and the pool refreshes at each round. But the dilution is taken upfront by the founders and returned to nobody, which is why the sizing argument is worth having.

   Where candidates lose it

   Describing the pool and never saying it comes out of the pre-money. That single fact is the whole question. And not being able to quantify it — the interviewer will ask what a 15 percent pool does to the effective pre-money, so have the arithmetic ready.

   Expect next

   • What pool size would you argue for at Series A and why?
   • How would a founder negotiate against this?
   • What happens to unissued options at the next round?
3. 044A founder owns sixty percent and raises ten million at a forty million pre-money. What do they own afterwards?Cap table and dilutionCorephone / first roundGrowth equity

   Say this

   Forty-eight percent. The post-money is $50m, the new investor takes $10m over $50m which is 20 percent, and every existing holder is diluted by that 20 percent. Sixty times 0.8 is 48.

   Then walk it

   1. Post-money equals pre-money plus the raise: $40m plus $10m is $50m.
   2. Investor ownership is new money over post-money: $10m over $50m, so 20 percent. Never over the pre-money — that is the standard error and it gives you 25 percent.
   3. Dilution factor for everyone else is one minus 20 percent, so 0.8. The founder's 60 percent becomes 48 percent. The other existing 40 percent becomes 32 percent. Check: 48 plus 32 plus 20 is 100.
   4. Now the follow-up that always comes: add a 10 percent post-closing option pool out of the pre-money. The pool takes 10 percent of the post-money company, so the existing holders are diluted by both the pool and the round. The founder lands nearer 42 percent than 48.
   5. And say whether you are quoting fully diluted. Fully diluted includes the option pool, issued and unissued options, warrants, and any convertible instruments. Every real ownership number in venture is fully diluted, and 'on an as-converted basis' is the phrase that signals you know it.
   6. One sanity habit: check that the percentages sum to 100 before you speak. Half the errors in these questions are arithmetic, not concept, and the interviewer cannot tell the difference.

   Where candidates lose it

   Dividing the raise by the pre-money. $10m over $40m is 25 percent and it is wrong. Ownership is always new money over post-money. The second trap is answering the clean question and then getting caught by the pool version, so volunteer the pool adjustment before they ask.

   Expect next

   • Now add a 12 percent option pool out of the pre-money. What do they own?
   • What if there is $3m of SAFEs at a $15m cap outstanding?
   • What would they own after two more rounds of 20 percent each?
4. 045How much should founders own at IPO, and why does it matter to you as an early investor?Cap table and dilutionIntermediatetechnicalGrowth equityLate-stage VC

   Say this

   Somewhere in the ten to twenty percent range for the founding team collectively is typical and healthy. It matters because below roughly ten percent the founders' incentive to grind out the last five years of value creation weakens badly, and that is a risk sitting in your position, not theirs.

   Then walk it

   1. The arithmetic of a normal path: five or six rounds at 15 to 25 percent dilution each, plus pool top-ups, takes a founding team from 100 percent to the teens. Two founders splitting 15 percent at IPO is a perfectly standard outcome.
   2. Why the floor matters. A CEO with 3 percent of a company worth $2bn has $60m, which is life-changing, and the marginal incentive to spend another five years doubling it is much weaker than for someone holding 15 percent. Boards deal with this by issuing large new grants, which dilutes you again.
   3. So as an early investor I care about founder ownership for a purely selfish reason: it determines whether the person driving my biggest position is still motivated in year eight, and whether the company will have to spend equity to re-motivate them.
   4. This is one of the strongest arguments for capital efficiency. Every unnecessary round costs the founders 15 to 20 percent of what they hold, and the cheapest way to protect founder ownership is to need less money.
   5. It also shapes how I think about secondaries. Letting a founder sell 5 to 10 percent of their holding in a later round takes personal financial pressure off and often makes them bolder rather than lazier. I would generally support a modest, capped founder secondary rather than watch them make risk-averse decisions.
   6. The honest caveat: there is no magic threshold and plenty of enormous companies IPO'd with founders in single digits, sometimes with dual-class shares that preserve control while the economics diluted. Control and economics are separable, and dual-class structures are how that gets handled in practice.

   Where candidates lose it

   Treating this as a founder-welfare question. The interviewer wants to hear that founder ownership is a risk factor in your own position. And if you cannot connect it to capital efficiency and to dual-class control structures, the answer stays superficial.

   Expect next

   • How would you feel about a founder selling secondary at Series C?
   • What does dual-class stock do here?
   • How many rounds is too many?
5. 046If a company raises one hundred dollars of debt and buys back one hundred dollars of shares, what happens to enterprise value and equity value?Cap table and dilutionIntermediatetechnicalSilver LakeTechnology, Media and Telecom · San Francisco · 2022

   Say this

   Enterprise value is unchanged and equity value falls by one hundred. Nothing happened to the operating business, so enterprise value cannot move. Debt went up by 100, cash is unchanged because it went straight out to shareholders, so net debt is up 100 and the equity is down 100.

   Then walk it

   1. Enterprise value equals equity value plus net debt. It is a measure of the operating asset, and neither raising debt nor buying stock changes the cash flows that asset produces.
   2. Trace the cash. Raise $100 of debt: cash up 100, debt up 100, net debt unchanged, enterprise value unchanged, equity value unchanged. Then spend the $100 buying shares: cash down 100, so net debt is now up 100.
   3. Since enterprise value is fixed, equity value must fall by 100. And that is right — you handed $100 to the shareholders who sold, so the remaining equity is worth $100 less in aggregate.
   4. Now the part that catches people: share price should not change in a frictionless world. The aggregate equity fell 100 and the share count fell by 100 divided by the price, so value per remaining share is the same. The shareholder is not richer; the composition of their claim changed.
   5. Then the real-world second-order effects worth naming. The tax shield on the new debt has genuine value, which nudges enterprise value up. Higher leverage raises the cost of equity and the risk of distress, which nudges it down. Net effect is small at low leverage and negative at high leverage.
   6. And EPS goes up, which is why companies do it, and why buybacks get announced as if value was created. Fewer shares and only a partial earnings hit from after-tax interest. Accretive to EPS, roughly neutral to value. That distinction is the entire point of the question.

   Where candidates lose it

   Saying enterprise value falls because debt rose. Debt is in the bridge from enterprise value to equity value, not in enterprise value itself. The second trap is saying the share price rises because there are fewer shares — the aggregate equity fell by the same amount, so per share it is a wash before you get to the tax shield.

   Expect next

   • What happens to earnings per share?
   • Does the share price change? Why not?
   • At what leverage level would enterprise value actually fall?

   Reported by candidates at Silver Lake (Technology, Media and Telecom, San Francisco, 2022). Source: Wall Street Oasis.

6. 047Why would a distressed company have a high equity value?Cap table and dilutionHardtechnicalSilver LakeTechnology, Media and Telecom · San Francisco · 2022

   Say this

   Because equity in a levered company is a call option on the enterprise value, and an option has value even when it is deep out of the money. If there is any chance the business recovers enough to clear the debt, the equity is worth something, and the more volatile the outcome the more that option is worth.

   Then walk it

   1. Set it up as the option: equity value equals the enterprise value less the debt, floored at zero. That is exactly the payoff of a call struck at the face value of the debt. Limited liability is what creates the floor.
   2. So even if enterprise value today is $800m against $1bn of debt, the equity is not worth zero. It is worth the option premium — the probability-weighted value of the scenarios where the business recovers above $1bn before the debt matures.
   3. And the counterintuitive consequence: volatility increases the equity value. A distressed company with a wildly uncertain outcome has more valuable equity than an equally distressed company with a certain modest decline, because only the upside tail accrues to the equity while the downside is the creditors' problem.
   4. Which explains the behaviour you see in distressed situations: management and equity holders favour risky strategies, because they capture the upside and creditors eat the downside. That is the classic risk-shifting conflict, and it is why credit agreements have covenants.
   5. Time to maturity also matters, same as an option. Debt maturing in five years gives the equity far more optionality than debt maturing in six months, which is why the maturity wall, not the leverage ratio, is usually what actually triggers a restructuring.
   6. The other mundane reasons a screen might show a high equity value on a distressed company: a large cash balance that has not been marked against the operating decline, an unconsolidated stake or real estate worth more than the operating business, or a retail-driven share price detached from the fundamentals. Worth naming, but the option answer is the one they want.

   Where candidates lose it

   Answering only with the mundane explanations — hidden assets, cash on the balance sheet. Those are real but this question is testing whether you see equity as a call option on enterprise value. Get to the option framing first, then add that volatility raises the equity value, which is the part that separates a good answer from a complete one.

   Expect next

   • What happens to that option as the debt maturity gets closer?
   • Why do equity holders in a distressed company favour risky strategies?
   • How would you value the debt in that situation?

   Reported by candidates at Silver Lake (Technology, Media and Telecom, San Francisco, 2022). Source: Wall Street Oasis.

7. 048What goes into a fully diluted share count, and why do you insist on it?Cap table and dilutionIntermediatetechnicalGrowth equity

   Say this

   Common shares, all preferred on an as-converted basis, all issued options whether vested or not, the entire unissued option pool, warrants, and any SAFEs or notes converted at their caps. Everything that will one day be a share. You insist on it because every other denominator understates your dilution.

   Then walk it

   1. Common: founders and anyone who has exercised. Preferred: converted one-for-one unless there has been an anti-dilution adjustment, in which case at the adjusted ratio.
   2. Options: all granted options, vested or not, plus the unissued pool. Including the unissued pool is what makes it fully diluted rather than merely as-converted, and it is the line founders most often leave out.
   3. Convertible instruments: SAFEs and notes converted at whichever of their cap or discount gives more shares, plus accrued interest on notes. If the company has $4m of outstanding SAFEs, they are shares and pretending otherwise misstates your position by several points.
   4. Warrants, including anything issued to a venture debt lender. Venture debt typically carries warrant coverage of 10 to 25 percent of the loan amount, and it is easy to miss in a data room.
   5. Why it matters practically: your ownership, the preference stack, and every per-share number in the waterfall depend on the denominator. A term sheet that says 20 percent on a basic share count and 16 percent fully diluted is a materially different deal, and the document will always say fully diluted.
   6. So in diligence I would rebuild the cap table myself from the underlying documents rather than accept the founder's spreadsheet. It is the single most common place where numbers are wrong, usually honestly — a founder who has raised on four SAFEs and two notes often genuinely does not know their own fully diluted number.

   Where candidates lose it

   Forgetting the unissued option pool, or forgetting warrants attached to venture debt. Both are real shares. And accepting the company's cap table at face value — rebuilding it is table stakes for an associate, and saying you would do it is part of the answer.

   Expect next

   • How do you handle warrants from a venture debt facility?
   • What is the difference between as-converted and fully diluted?
   • Where do founders' cap tables usually go wrong?

Firm tags come from public, anonymous candidate reports on Wall Street Oasis: strong signal, not sworn testimony. Firms are named as the places a question was reported, not as partners of Fin Maverick. Answers are written for this page to show how to think out loud; they are not scripts to recite.