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. 063You are on the board and the CEO wants to fire their co-founder. What do you do?Board and governanceHardsuperdayEarly-stage VCGrowth equity

   Say this

   Slow it down by two weeks, get the facts independently, then support a clean decision either way. My job is not to adjudicate the relationship — it is to make sure whichever way it goes, the company keeps functioning and the equity consequences are handled properly before anyone is told.

   Then walk it

   1. First, separate the question of whether the person should go from the question of how. The first is a performance judgement I should test; the second is where boards do the real damage by rushing.
   2. Get independent information. Talk to the co-founder directly, talk to two or three people who work with both of them, and understand whether this is a capability gap, a role that has outgrown the person, or a personal breakdown. Those three have different answers — the second is often solved by changing the role rather than removing the person.
   3. Then the equity question, before any conversation happens. What is vested, what accelerates, what does the shareholders' agreement say about a departing founder's shares, and is there a repurchase right. A founder leaving with 18 percent fully vested and no involvement is a problem every future investor will raise, and the time to negotiate it is before the termination, not after.
   4. Then the operational question: what does this person actually hold? Key customer relationships, the entire backend, the regulatory licence in their name. I have seen a co-founder removal take out a third of engineering because nobody mapped the dependency first.
   5. Then support the CEO if the case holds. A board that blocks a CEO's decision about their own leadership team, without a serious reason, has just told the CEO they are not in charge. But I would also say clearly that this is a signal about the CEO — how they handle it, whether they are generous, and whether they have been avoiding the conversation for a year.
   6. And be honest about the pattern: the modal error here is not firing too fast, it is a board that let a broken co-founder relationship run for eighteen months because nobody wanted the conversation. Speed in the decision, care in the execution.

   Where candidates lose it

   Taking sides immediately, in either direction. Backing the CEO reflexively ignores your duty to all shareholders and to the facts; blocking them undermines their authority. The structure is: pause, verify independently, sort the equity and dependency consequences first, then support a clean decision.

   Expect next

   • What if the departing founder has 20 percent fully vested?
   • What if you think the CEO is the problem, not the co-founder?
   • How do you handle the announcement to the team and to customers?
2. 065In diligence you find that a founder overstated revenue. What do you do?Board and governanceHardsuperdayGrowth equity

   Say this

   Establish whether it was a definitional error or a deliberate misstatement, in that order, because they lead to completely different outcomes. A founder counting signed letters of intent as ARR is a founder who needs better accounting. A founder who knowingly gave me a number they knew was false is a pass, regardless of how good the company is.

   Then walk it

   1. First, go back to the primary data. Pull the bank statements, the invoices, the contracts and the accounting system, and rebuild the revenue figure myself. Do not go to the founder with an accusation built on a spreadsheet inconsistency.
   2. Then classify it. Definitional: counting bookings as revenue, annualising a one-month pilot, including a non-binding LOI, or recognising a multi-year contract upfront. All of these are common, mostly honest, and mostly fixable with a CFO.
   3. Deliberate: a number the founder knew was wrong, presented to raise money. That is a character finding and it is disqualifying. The reason is not moralism — it is that I am buying an illiquid position for eight years in a company where the only source of information is this person's word.
   4. Ask the question directly and watch the response. The good outcome sounds like 'you're right, we've been counting it as bookings and I should have flagged it'. The bad outcome is a moving explanation, or blaming the analyst, or a number that changes again when pressed.
   5. Then check whether it is systemic. If revenue was overstated, look at retention, pipeline and headcount too. One inflated metric is rarely alone, and a pattern converts a definitional problem into a deliberate one.
   6. And the obligation to others: if I pass on a character finding, I would tell my own partnership plainly why. Whether to tell other investors is genuinely harder — there is defamation risk and I would take legal advice — but I would not give a positive reference, and I would say nothing rather than something misleading.

   Where candidates lose it

   Jumping straight to 'I'd walk away'. It sounds principled and it shows no judgement, because most revenue discrepancies at seed and Series A are definitional. The structure is: verify from primary documents, classify honest versus deliberate, test with a direct question, then act. Only the deliberate case is an automatic pass.

   Expect next

   • Where is the line between aggressive and dishonest?
   • Would you tell other investors?
   • What if you had already signed the term sheet?
3. 066How would you structure a bridge round for a portfolio company that is six months from running out of cash?Down rounds and secondariesHardsuperdayEarly-stage VCGrowth equity

   Say this

   First establish what the bridge is bridging to — a specific metric that makes the next round fundable, not just more time. Then size it to reach that milestone with three months of buffer, structure it as a convertible instrument inside the existing syndicate, and make the cut in costs a condition rather than a suggestion.

   Then walk it

   1. The diagnostic question first: is this a bridge or a pier? A bridge reaches a specific, credible milestone — $4m of ARR, a signed enterprise customer, a clinical result. A pier is money that buys time with no defined destination, and it is the most common way funds throw good capital after bad.
   2. Size it properly. Six months of runway is usually not enough to hit anything, so size to twelve to fifteen months including a cut, and be honest that a small bridge just brings you back to the same conversation with less credibility.
   3. Structure: typically a convertible note or SAFE that converts into the next priced round at a discount, often 15 to 25 percent, sometimes with a cap set near the last round. This avoids setting a new price at the worst possible moment, which is the main reason bridges are done as convertibles rather than priced rounds.
   4. Who funds it: the existing syndicate, pro rata. An inside round at a discount is normal. The decision is whether every existing investor participates — if one refuses, the others are effectively subsidising them, which is when pay-to-play or a senior preference for the bridge money gets negotiated.
   5. Conditions, and this is where the real work is. A cost reduction that extends the runway on its own, a revised plan the board signs off on, and usually a commitment about the fundraising process starting by a specific date. Bridge capital without operational conditions attached is a gift, not an investment.
   6. And the honest internal test: would I put this money into a new company at the implied price instead? If not, I should consider whether the right answer is a smaller bridge aimed at a sale of the company rather than at another round. Funding a managed exit is a legitimate and underused use of bridge capital.

   Where candidates lose it

   Structuring the instrument before establishing what the milestone is. The financial engineering is the easy part; the judgement is whether there is a credible destination. And never propose a bridge without a cost cut attached — every experienced investor will ask, and 'we didn't want to demoralise the team' is not an answer.

   Expect next

   • What if one existing investor refuses to participate?
   • When is the right answer to fund a sale instead of a bridge?
   • Would you set a cap on the bridge, and where?
4. 067Walk me through a down round and what it does to the cap table.Down rounds and secondariesHardtechnicalGrowth equityLate-stage VC

   Say this

   New money comes in at a lower price per share than the last round, so the dilution is severe, anti-dilution provisions fire and reprice earlier preferred, and the option pool is usually underwater so it has to be refreshed. The founders and employees absorb almost all of it.

   Then walk it

   1. Start with the raw dilution. A company that raised at $200m post now raising $30m at $80m post gives the new money 37.5 percent, so everyone else is diluted by well over a third in one round.
   2. Then anti-dilution fires. Earlier preferred with weighted-average protection gets a lower conversion price and therefore more shares, and that adjustment comes entirely out of the common. With a full ratchet anywhere in the stack, the effect is brutal — earlier investors can end up with multiples of their original share count.
   3. Then the option pool problem, which people forget. Employee options struck at the old, higher price are worthless, so retention has collapsed. The fix is a new pool at the new strike, sometimes plus a repricing or exchange of existing grants, and that is another 10 to 15 percent of dilution on top.
   4. Put it together and a founding team at 35 percent before a serious down round can be in the low teens after it, with the option pool refreshed and the preference stack still sitting above them. The practical consequence is that the equity no longer motivates anyone, which is why down rounds are followed by departures.
   5. So the conversation the board has to have is about restructuring, not just pricing: converting some of the old preference stack to common, cutting the aggregate preference back, and issuing meaningful new founder and management grants. A clean down round with a reset stack is far better than a high-priced round loaded with structure.
   6. And the signalling and legal points. A down round is a repricing of the story as well as the shares, so customers and candidates hear about it. And existing directors approving a round in which their own funds participate at a favourable price sit in an obvious conflict, which is why an independent committee or a fairness process matters more here than anywhere else.

   Where candidates lose it

   Only calculating the arithmetic dilution and stopping. The full answer has four layers: raw dilution, anti-dilution firing, the underwater option pool, and the resulting retention problem. Missing the option repricing is the most common gap, and it is the one that actually determines whether the company survives the round.

   Expect next

   • Would you rather do a clean down round or a flat round with 3x participating preferred?
   • How do you handle underwater employee options?
   • What is the conflict when existing investors lead the round?
5. 068Why is a structured round often worse for a company than a clean down round?Down rounds and secondariesHardsuperdayLate-stage VCGrowth equity

   Say this

   Because it preserves the headline valuation by burying the real price in terms nobody outside the deal can see. The company looks like it raised flat, but a 2x senior participating preference with a full ratchet means the common is worth far less than in an honest down round at a lower price.

   Then walk it

   1. What structure means in practice: multiple liquidation preference, participation, senior rather than pari passu ranking, full ratchet anti-dilution, guaranteed IPO returns or ratchets on the IPO price. Each one transfers value from common to the new preferred without touching the headline number.
   2. Run it. A flat $500m round with $150m of new money at 2x senior participating means the first $300m of any exit goes to the new investor before anyone else sees a rupee. At a $400m exit, the common gets almost nothing — worse than if the round had simply priced at $200m with clean terms.
   3. The second cost is compounding: structure is senior and it stacks. The next investor demands terms at least as good, so you get a tower of preferences, and by the third round the common is a call option struck impossibly high. Employees work out that their options are worthless well before the board admits it.
   4. The third cost is optionality on exit. A heavy preference stack means a $300m sale pays management nothing, so the team will not sell, so the company keeps raising. Structure removes the reasonable exits and forces an all-or-nothing outcome.
   5. The clean alternative: reset the price, take the dilution, refresh the option pool, and keep the stack at 1x non-participating. Everyone knows where they stand, the recruiting story is honest, and a mid-sized exit still pays the team.
   6. This was the defining mistake of the 2021 to 2022 period. A lot of companies protected a unicorn headline with structure and discovered two years later that the structure, not the valuation, was what made them unfinanceable and unsellable. Being able to say that with a specific example is what makes this answer land.

   Where candidates lose it

   Treating a flat round as good news. Any time a valuation holds in a bad market, the first question is what the terms were. A candidate who does not ask for the preference stack before commenting on a valuation has not understood how late-stage rounds are actually priced.

   Expect next

   • What is an IPO ratchet and who does it hurt?
   • How would you find out whether a reported valuation was structured?
   • As the founder, which would you choose and why?
6. 077What return does a fund need to be considered top quartile, and what does that require of the portfolio?Fund economicsHardtechnicalSeed fundsVC fund operations

   Say this

   Roughly 2.5 to 3x net TVPI for an early-stage fund, which means about 3.5x gross before fees and carry. On a $100m fund that is $350m of gross proceeds, and given the power law it has to come from one or two companies, which sets a specific requirement on ownership and exit scale.

   Then walk it

   1. Work the gross-to-net gap first, because most candidates skip it. To return 3x net you need roughly 3.5 to 3.8x gross: fees consume 15 to 18 percent of the fund and carry takes 20 percent of the profit above capital.
   2. So $100m committed needs about $350m back gross. Apply the power law: expect half the portfolio to return under 1x, so the top two or three names have to produce $280m to $300m of it.
   3. Which fixes the requirement. One company producing $200m means either a $2bn exit with 10 percent retained, or a $1bn exit with 20 percent retained. Both are demanding, and the second is usually harder to hold through three rounds of dilution than the first is to achieve.
   4. That is why fund size is the binding constraint on strategy. A $100m fund can get there on a single $2bn outcome. A $1bn fund needs the equivalent of five of them, and there are not many $2bn-plus outcomes in a decade, which is the structural reason large venture funds underperform small ones on multiple.
   5. The other lever is DPI timing, because top quartile is measured by vintage against peers and an LP is looking at IRR too. The same 3x delivered by year eight rather than year thirteen is a completely different ranking.
   6. And the caveat about the benchmark itself: quartile data is self-reported, survivorship-biased, and the dispersion in venture is extreme — the gap between top and median in venture is far wider than in buyout. Which is why LP capital concentrates so heavily in the same handful of firms, and why a new manager's pitch is so hard.

   Where candidates lose it

   Quoting a net multiple and never bridging to gross. Fees and carry are a 20 to 25 percent haul and ignoring them makes your portfolio arithmetic wrong. And failing to connect the fund-return requirement to fund size — that connection is the whole reason the question gets asked.

   Expect next

   • So what exit do you need from your single best company?
   • Why do larger venture funds tend to return lower multiples?
   • How much should the gross-to-net gap be?
7. 079Pitch me a company that is not in our portfolio that we should invest in.Sector theses and marketsHardsuperdayInsight PartnersSoftware · New York · 2022Insight PartnersLeveraged Buyouts · New York · 2023General AtlanticGrowth Equity · New York · 2022General AtlanticGrowth Equity · New York · 2021Silver LakeTechnology, Media and Telecom · San Francisco · 2022

   Say this

   Structure it in five beats and keep it to three minutes: the shift in the world, the company and its wedge, the evidence it is working, why it fits this firm's mandate, and what would kill it. Then stop and let them interrogate it — the pitch is the setup, the cross-examination is the actual test.

   Then walk it

   1. Beat one, the shift: what changed in the last two years that makes this possible and did not before. Regulation, a cost curve, a behaviour change, a platform. Without a 'why now', it is a feature, not a company.
   2. Beat two, the company and the wedge: what they sell, to whom, and why they win that first narrow segment. Be specific about the wedge — 'AI for healthcare' is not a wedge; 'prior-authorisation automation for mid-sized orthopaedic practices' is.
   3. Beat three, the evidence, with numbers and their source: revenue or run rate, growth, retention if you can find it, headcount trend from LinkedIn, app-store ranking, review velocity, whatever is observable. Say where each number came from. Two real numbers beat a page of narrative.
   4. Beat four, why this firm: stage, cheque size, sector fit, and what the firm specifically brings. If they lead $30m growth rounds, do not pitch a pre-seed. This beat is what separates a prepared candidate from someone reciting a favourite company.
   5. Beat five, the bear case and the price. Name the two things that would kill it, say what you would diligence first, and give a valuation view — what you would pay and why. A pitch with no price is not an investment recommendation.
   6. Then the return maths, briefly, because it is what they will ask: what has to be true for this to be a 10x. If you cannot get to a fund-returning outcome, say so and explain why it is still interesting, or pick a different company.

   Where candidates lose it

   Pitching a company already in their portfolio, or a household name where you have no edge. Check the portfolio page first. The second trap is describing the product for two minutes and never giving an investment view: no price, no bear case, no return maths. And pick something checkable — if you claim a revenue figure, know where it came from, because they will ask.

   Expect next

   • What would you pay for it, and what would you not pay?
   • What is the strongest argument against this investment?
   • What would you diligence first, and who would you call?

   Reported by candidates at Insight Partners (Software, New York, 2022); Insight Partners (Leveraged Buyouts, New York, 2023); General Atlantic (Growth Equity, New York, 2022); General Atlantic (Growth Equity, New York, 2021); Silver Lake (Technology, Media and Telecom, San Francisco, 2022). Source: Wall Street Oasis.

8. 082What do you think about this portfolio company?Sector theses and marketsHardsuperdayInsight PartnersGeneralist · New York · 2025Battery VenturesVenture Capital · Boston · 2019

   Say this

   Give a real assessment with a view, not a compliment. Say what you think the original thesis was, what evidence you can see about whether it is working, the one risk you would watch, and what you would want to know that you cannot see from outside. Flattery is the wrong answer and so is dismissal.

   Then walk it

   1. Reconstruct the thesis first: at the stage they invested, what must they have believed? That framing shows you can think like an investor rather than a customer, and it gives you something concrete to test.
   2. Then the observable evidence. Hiring trend and which functions they are hiring into, pricing page changes, customer logos on the website, review volume, app rankings, whether they have raised since and at what reported price. All public, all checkable.
   3. Then a view with a number attached where you can: my guess is they are somewhere between $20m and $40m of ARR based on headcount and the segment, growing well but slowing, and the interesting question is whether they can move upmarket before the incumbent bundles the feature.
   4. Then the risk. Pick one and make it specific — a competitor bundling, a channel dependency, a regulatory change, customer concentration. One well-argued risk is worth more than five generic ones.
   5. Then the question you cannot answer from outside, which is the most useful thing you can offer: 'what I would really want to see is net retention in the sub-$25k cohort, because everything about the pricing page suggests they moved upmarket and I cannot tell whether they kept the long tail or shed it.'
   6. And keep it genuinely respectful. These are their companies and the founders are their relationships. Critical is fine, dismissive is disqualifying, and there is a real difference between 'here is the risk I would watch' and 'I don't think this works'.

   Where candidates lose it

   Praising it, which shows nothing, or trashing it, which shows no judgement about the room you are in. Also: do not guess the numbers if you have not looked. This question rewards half an hour of preparation on three or four of their most prominent companies, and the candidates who do it are immediately obvious.

   Expect next

   • Would you have invested at the last round price?
   • Which company in our portfolio would you not have done?
   • What would you want to diligence about it?

   Reported by candidates at Insight Partners (Generalist, New York, 2025); Battery Ventures (Venture Capital, Boston, 2019). Source: Wall Street Oasis.

9. 083What is the worst investment this firm has made, and why?Sector theses and marketsHardsuperdayBessemer Venture PartnersGrowth Equity · New York · 2014

   Say this

   Pick a publicly known writedown, explain the thesis that must have made sense at the time, and then say what turned out to be wrong. The point is to analyse a decision under uncertainty, not to score a point. Answer with respect and with a lesson, and do not pretend the firm has never lost money.

   Then walk it

   1. Choose a company that has been publicly reported as shut down, sold below the last round, or written down. Never speculate about a live portfolio company's trouble — that is a bad-judgement signal about discretion, and the room will notice.
   2. Then be generous about the original thesis. Reconstruct why it was a reasonable decision with the information available. Investors respect someone who can see the case for a decision that went wrong, because that is the position they are in every week.
   3. Then the specific failure mode, and pick one: the market was smaller than underwritten, the unit economics never worked at scale, capital intensity was misjudged, the moat was a feature, or a regulatory assumption failed. Naming the category is what makes it analysis.
   4. Then the generalisable lesson, which is the whole reason the question exists: something like 'the pattern seems to be paying a growth multiple for revenue that was bought rather than earned, and the tell was a burn multiple above 3 that got explained as investment'.
   5. Some firms have literally institutionalised this — Bessemer publishes an anti-portfolio of the great companies it missed, which is a direct invitation to have this conversation intelligently. Knowing that a firm does this, and referencing it, is a strong signal you have done real preparation.
   6. And a light touch on tone: this is a test of whether you can disagree with the people interviewing you without being either sycophantic or rude. Say the analysis, offer the lesson, and do not moralise about their judgement.

   Where candidates lose it

   Two opposite failures. One, refusing to answer — 'I'm sure they were all well considered' — which reads as either no preparation or no spine. Two, being gleeful about a loss, or speculating about a live company that is visibly struggling. Pick something publicly resolved, be generous about the original thesis, and land on a lesson.

   Expect next

   • What would you have done differently at the time?
   • What is the most common way investors get a thesis wrong?
   • Which of our investments do you most admire, and why?

   Reported by candidates at Bessemer Venture Partners (Growth Equity, New York, 2014). Source: Wall Street Oasis.

10. 084How do you think the venture capital process will change in the next five to ten years, and how should we prepare?Sector theses and marketsHardsuperdayWPWarburg PincusVenture Capital · New York · 2013

    Say this

    Three shifts I would bet on: sourcing and early diligence become largely data-driven, the industry barbells into a handful of very large platforms and many small specialists with the middle squeezed out, and liquidity stops depending on IPO windows because secondaries and continuation vehicles have become permanent infrastructure.

    Then walk it

    1. Sourcing: the parts of the job that are pattern-matching over observable data — hiring velocity, repo activity, app rankings, payment data — get automated, and several firms already run this. What does not automate is the founder judgement and winning a competitive round, so the value of a partner shifts toward those and away from coverage.
    2. Company formation changes the cheque sizes. If a team of four can build what needed thirty people, seed rounds get smaller and the number of credible companies goes up. That is good for small specialist funds and awkward for large funds that need to deploy, because you cannot put $20m into a company that needs $3m.
    3. Structure: the barbell. Multi-billion platforms doing seed through pre-IPO with adjacent credit and wealth businesses, and small high-ownership specialist funds. The $300m to $800m generalist fund with no particular edge is the position under most pressure, and that is the strategic question for most firms in this market.
    4. Liquidity: secondaries, continuation vehicles and employee tender offers are now standard rather than distressed, driven by ten-year holds and the DPI problem. Firms that build a dedicated liquidity capability will return capital faster and raise more easily, and that is becoming a real differentiator with LPs.
    5. How to prepare, which is the half of the question candidates skip. Build the data platform now because it takes years of accumulated data to be useful. Decide explicitly which end of the barbell you are on and stop pretending to be both. Build the secondary capability. And protect the thing that does not commoditise: the relationships that get you into a round you would otherwise be shown after it is full.
    6. And the honest hedge: people have been predicting the disruption of venture for thirty years and the core of the job — a small number of judgement calls on people, made under uncertainty — has not changed. What changes is the mechanics around it, so I would be confident about the sourcing and liquidity predictions and much less confident that the decision itself gets automated.

    Where candidates lose it

    Answering only the first half. 'How should we prepare' is the actual question and it wants concrete firm-level actions. Also predicting that AI will replace investment judgement, which sounds bold and lands badly in a room whose entire business is that judgement. Be specific about what commoditises and what does not.

    Expect next

    • Which end of that barbell should we be on?
    • What part of the job will not be automated?
    • What should we start doing this year?

    Reported by candidates at Warburg Pincus (Venture Capital, New York, 2013). Source: Wall Street Oasis.

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.