What Could Go Right Lens
Evaluate asymmetric upside before letting downside dominate the decision
- Difficulty
- Moderate
- Time to result
- ~weeks to results
- Steps
- 5
- Confidence
- 99%
The lens reframes failure in domains governed by power-law outcomes. A failed venture investment can lose one times the capital committed, while declining an exceptional company can forfeit returns hundreds or thousands of times that amount. Decision-makers therefore ask not only what can go wrong, but what could go right, how large that outcome could become, and which assumptions would make it possible. Postmortems then examine missed winners alongside investments that went to zero. This does not mean ignoring risk or funding every optimistic story; it means weighting errors according to their actual asymmetry. The method works only where individual losses are bounded, portfolios can absorb failures, and a rare outlier can compensate for many unsuccessful bets. Used elsewhere, it can become reckless optimism rather than disciplined opportunity analysis.
Origin
Benchmark partner Bruce Dunlevie coined the phrase “what could go right?” after the firm's missed opportunity to invest in Google clarified the asymmetry between losing invested capital and missing an extreme winner.
Core principles
- 01Missed upside can dwarf invested capital losses
- 02Power-law portfolios require searching for extreme winners
- 03Failure includes omission, not only commission
- 04Downside analysis should not erase plausible upside
- 05The lens belongs where losses are capped and gains can compound dramatically
How to run it
- 1
Confirm the Asymmetry
Estimate the most likely maximum loss and the scale of a plausible exceptional outcome. Proceed with this lens only when upside materially exceeds bounded downside.
Pro tip Use multiples of capital to make omission and commission costs comparable.
Watch out Do not use venture-style reasoning when debt, leverage, or concentration can cause ruin.
- 2
Build the Right-Case Thesis
Describe the customer adoption, market expansion, competitive position, and compounding required for the opportunity to become an outlier. Make the positive case concrete enough to challenge.
Pro tip Ask which surprising development would make today's estimate look far too small.
Watch out A large market slogan is not a causal upside thesis.
- 3
Compare Both Failure Modes
Evaluate the damage from investing and being wrong alongside the opportunity cost of declining and being wrong. Give both errors explicit attention.
Pro tip Include reputational or career incentives that may cause committees to prefer safe-looking omissions.
Watch out Do not treat hypothetical upside as guaranteed merely because omission is uncomfortable.
- 4
Size for Survival
Limit exposure so the portfolio can absorb many failures while retaining meaningful participation in winners. Preserve the ability to keep searching.
Pro tip Judge the decision as part of a portfolio rather than as a standalone certainty.
Watch out Oversizing a promising bet can destroy the loss asymmetry.
- 5
Study Missed Winners
Review opportunities that became exceptional after rejection and identify which signals were undervalued. Update sourcing, analysis, and decision criteria accordingly.
Pro tip Separate unforeseeable outcomes from errors caused by a consistently narrow lens.
Watch out Avoid rewriting history as though every eventual winner was obvious at the time.
In the wild
Benchmark could have invested twelve million dollars in Google but did not pursue the opportunity. Gurley contrasts that missed thousand-times outcome with an investment of the same size going to zero, which would have cost only the original capital.
→ The firm shifted its failure analysis toward missed outliers and adopted the question “what could go right?”
An innovation fund considers a small investment in a tool with uncertain adoption but a credible path to becoming infrastructure for a large market. It caps the loss at one percent of the portfolio while documenting the adoption loop that could produce a hundred-times return.
→ The team can participate in the upside without allowing one failure to threaten the portfolio.
Common mistakes
Ignoring Ruin Risk
The method assumes a bounded loss and a portfolio able to absorb it. Leverage or excessive concentration can invalidate the entire asymmetry.
Using Upside as a Fantasy
A large numerical possibility is not enough. The team must explain the mechanism, milestones, and evidence that could create the outcome.
Reviewing Only Money Lost
Studying only investments that failed reinforces excessive caution. Missed winners may contain the more economically important lessons.
Is it for you?
Best for
It is best for venture portfolios and other bounded-loss decisions with rare but potentially enormous upside.
Not ideal for
It is not ideal for leveraged, ruinous, or ordinary-return decisions where losses are not capped and extreme upside is implausible.
From the transcript
“if we invest twelve million dollars and it goes to zero, you lose one time your money. If you failed to invest twelve million dollars…”
“My partner Bruce came up with this phrase, what could go right?”
“You orient yourself towards the failure being missing out on a huge winner”
From the episode
BONUS: Bill Gurley on Investing Early in Tech Disruptors & 'Runnin' Down a Dream'
Bill Gurley