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. 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.

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.