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. 026If revenues get hit in a quarter, what would you do as CFO to preserve cash flow?Unit economics and cohortsIntermediatetechnicalSilver LakeTechnology, Media and Telecom · San Francisco · 2022

   Say this

   Work in order of reversibility and speed: first the levers that cost nothing to pull and can be undone, then working capital, then discretionary spend, then headcount last. And before any of it, establish whether the quarter is a timing issue or a demand issue, because the answer is completely different.

   Then walk it

   1. Diagnose first. A slipped enterprise deal that closes in six weeks is a timing problem and you do not restructure the company around it. A cohort that stopped converting is a demand problem and you act hard.
   2. Fastest reversible levers: freeze discretionary spend — travel, events, consultants, new tooling — and pause the hiring pipeline without touching existing staff. That typically finds 10 to 15 percent of operating expense within a quarter and can be switched back on.
   3. Working capital next, because it is cash without cutting the business. Tighten collections and chase the ageing receivables, move new contracts to annual upfront with a discount rather than monthly, and stretch payables where the supplier relationship tolerates it. Annual prepay is the single biggest lever in a software business.
   4. Then capital expenditure and committed spend: defer the office build-out, renegotiate the cloud commitment, and look hard at the software stack, where most companies are paying for 30 percent more seats than they use.
   5. Headcount last, and if you do it, do it once and deeply enough that you do not have to come back. Repeated small cuts destroy more value through uncertainty than the cash they save. And protect the revenue-generating and product functions, because you still have to grow out of this.
   6. Then the financing side, which is the real CFO job: extend runway to at least eighteen months, open a venture debt or revolver conversation while the numbers still look fine rather than after they do not, and tell the board in the quarter it happens, not the quarter after.

   Where candidates lose it

   Going straight to layoffs. It signals no sense of sequencing and it is the slowest source of cash once you account for severance. The structure they want is reversible-before-irreversible, and the diagnosis — timing versus demand — before any of it. Mentioning annual prepay and receivables is what marks out someone who has actually looked at a cash flow.

   Expect next

   • How much runway would you insist on holding?
   • When would you take venture debt instead of cutting?
   • How do you decide whether it is a timing problem or a demand problem?

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

2. 027What metrics would you look at when valuing a retail company?Unit economics and cohortsIntermediatetechnicalSilver LakeTechnology, Media and Telecom · San Francisco · 2022

   Say this

   Same-store sales growth, gross margin, sales per square foot, inventory turns, and the payback on a new store. Retail is a unit-level business, so I would value the existing store base on cash flow and the growth story on how many more units can earn their cost of capital.

   Then walk it

   1. Same-store or like-for-like sales growth is the single most important number, because it strips out the flattering effect of opening stores. A chain with 30 percent revenue growth and minus 2 percent same-store sales is buying growth with capital.
   2. Unit economics of a new store: build-out cost, time to maturity, steady-state four-wall EBITDA, and therefore payback. Good specialty retail pays back in 18 to 30 months. Beyond that, expansion destroys value.
   3. Working capital and inventory. Inventory turns, weeks of cover, and the markdown rate. Retail failures are almost always inventory failures first — the P&L looks fine while the balance sheet fills with unsold stock that later gets discounted through gross margin.
   4. Cost structure: occupancy as a share of sales, because it is fixed and it is what kills you when traffic falls, and labour. Then the operating leverage question — how much can sales fall before four-wall EBITDA goes negative.
   5. For an omnichannel or e-commerce-heavy retailer, add CAC and repeat rate, contribution margin after delivery and returns, and the return rate itself, which in apparel can run 30 percent and quietly destroys the reported gross margin.
   6. Valuation itself: EV/EBITDA against peers, adjusted for lease obligations, since capitalised leases are debt in substance and post-IFRS 16 they sit on the balance sheet. And a sanity check on EV per store against replacement cost, which sets the floor.

   Where candidates lose it

   Valuing it like a software company on a revenue multiple, or quoting only same-store sales without the new-store payback. And forgetting leases — a retailer with $2bn of lease obligations and a headline low EV/EBITDA is not cheap, and in a tech-focused fund this is exactly the trap the question is set to catch.

   Expect next

   • How do you treat operating leases in enterprise value?
   • What is a good payback period on a new store?
   • How does the answer change for a pure e-commerce retailer?

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

3. 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.

4. 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.

5. 054An oil company loses forty million dollars of market capitalisation because of litigation, then sells an asset to pay for it. Is the share price drop justified?Early-stage valuationHardsuperdaySilver LakeTechnology, Media and Telecom · San Francisco · 2022

   Say this

   A $40m drop is justified only if the expected after-tax cash cost of the litigation is about $40m and nothing else changed. The asset sale is a separate question: if the asset was sold at fair value, the sale itself destroys no value and the share price should not move again for it.

   Then walk it

   1. First, price the liability properly. What matters is the probability-weighted, after-tax, present value of the cash outflow, plus any legal costs, less insurance recovery. A $40m headline settlement at a 25 percent tax rate and 70 percent probability is closer to $21m of economic cost.
   2. Second, ask whether the litigation revealed something. If it signals an ongoing practice that will generate more claims, or a regulatory exposure across the asset base, the drop should exceed the direct cost — the market is repricing future cash flows, not just paying a fine. That is usually the real answer for litigation-driven drops.
   3. Third, the asset sale. Selling an asset at fair value is value-neutral: you swap an asset for cash of equal value. Enterprise value falls by the asset's value, cash rises, equity value is unchanged.
   4. But sold at a discount, which is what a forced seller does, it is value-destructive twice over — once for the discount and once for the loss of an asset that may have been worth more inside the portfolio than to the buyer. A distressed sale to fund a settlement is a classic way a $40m problem becomes a $60m one.
   5. Then the tax detail worth mentioning for an oil asset: a sale can trigger a large gain against a low tax basis, so the after-tax proceeds can be materially less than the headline price, and the company may need to sell more than $40m of assets to net $40m.
   6. So the structured answer is: justified if the drop equals the after-tax expected cost and the litigation is genuinely one-off. Understated if it signals a systemic problem. Overstated if the market priced the headline number rather than the probability-weighted after-tax figure, which markets frequently do on litigation news.

   Where candidates lose it

   Answering yes or no. This is a framework question and the only wrong answer is an unconditional one. The two things you must separate are the cost of the liability and the information content of the litigation, and you must state that a fair-value asset sale is value-neutral while a forced one is not.

   Expect next

   • What if the asset was sold at a 20 percent discount to fair value?
   • How would you price the litigation if the outcome is binary?
   • Does the asset sale change enterprise value or equity value?

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

6. 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.

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.