The Surface Area of Opportunity Test
Decide whether to hold a guaranteed but wrong opportunity by comparing it against everything you cannot see while you are holding it.
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 86%
After Twitch acquired the youth e-sports app, Shaan stayed to earn out because he felt he needed to secure the bag. He asked a more successful friend, Sully, what he would do, and got the answer: sell so the team and investors are fine, then quit on day one. Shaan objected that one year was no big deal for that much money. Sully's reply was that the surface area of opportunity is too wide. Pressed for an example, Sully immediately generated one on a walk through the Mission: Klaviyo for SMS in e-commerce, on the argument that SMS is like email but with a 90 percent open rate, and that a hundred brands that matter would make it a valuable company. Shaan pushed back on the obvious objections, that Klaviyo would add SMS and that competitors existed, and Sully said he was focusing on the wrong thing. They never built it; Shaan later spotted Postscript in Y Combinator doing exactly that, Sully invested, and Postscript became a multi-hundred-million-dollar company in the same window Shaan spent earning out. Shaan's generalisation is that only by turning down the known thing do you become available to find the one you want.
Origin
Sully articulated it to Shaan on a ninety-minute pacing walk through the Mission in San Francisco while they talked through what Shaan should do after the Twitch acquisition.
Core principles
- 01The known thing is a guarantee; everything better is unknown by definition.
- 02Occupied time does not just cost the hours, it costs the encounters.
- 03If you are talking yourself into it, you have already lost the argument.
- 04Availability is what generates options, not planning.
- 05A boring, ready-made idea beats an exciting unresolved one.
How to run it
- 1
Name the guarantee honestly
State what the certain thing is and what it pays. For Shaan it was an earn-out at Twitch that he stayed two years for, driven by what he calls a desperation to secure the bag.
Pro tip Separate 'I need this money' from 'I want this money.' Only the first one is a real constraint.
- 2
Test whether it is the one
Ask whether being an employee at the acquirer, or whatever the guarantee is, was ever going to be your future. Shaan's answer was no, and he knew it while he was signing up for it.
Watch out Watch for the talking-yourself-into-it tell. Shaan's dating analogy is the check: if you are constructing an argument for staying, you already have your answer.
- 3
Force a concrete alternative into existence
Do not accept 'you could do anything' as an answer. Shaan demanded an example and Sully produced Klaviyo for SMS within minutes, complete with the market logic and a target of a hundred brands that matter.
Pro tip Ask someone already operating in an adjacent market. Sully was in e-commerce, which is why the idea was specific rather than generic.
- 4
Stop defending the objections
When Shaan raised that Klaviyo would probably add SMS and that other companies existed, Sully told him he was focusing on the wrong thing. The objections are usually true and usually irrelevant to whether the opportunity is real.
Watch out A ready-made idea will feel almost boring precisely because there is nothing left to figure out. That flatness is not a red flag.
- 5
Exit cleanly, then become available
Sully's specific instruction was to sell so the team is fine and the investors are happy, and then quit on day one. The point of the clean exit is that it buys the availability without leaving damage behind.
Pro tip Do the sale properly. The framework is about the day after, not about refusing the deal.
In the wild
Sully pitched Shaan on building an SMS platform for e-commerce, arguing SMS was email with a 90 percent open rate and that a hundred brands that matter would make it valuable. They went down the rabbit hole briefly, tried to find an operator to run it, and never built it. Shaan then spotted Postscript in Y Combinator doing exactly that and sent it to Sully.
→ Sully and his brother invested. Postscript became a multi-hundred-million-dollar company over the same period Shaan spent earning out at Twitch.
Shaan stayed two years at Twitch rather than the one year he would now advise, while separately starting an e-commerce business around the same time that he does not discuss publicly.
→ That e-commerce business does roughly $15 million a year, profitable and bootstrapped, and Shaan says it is worth more than what he earned out at Twitch. His conclusion: had he started it on day one, the surface area would have paid out sooner.
Common mistakes
Treating one more year as costless
Shaan's exact objection was that one year is no big deal for that much money. The error is pricing the year in salary rather than in the opportunities that only appear to someone who is available. Postscript happened inside that year.
Rejecting an idea because the objections are obvious
Shaan immediately asked whether Klaviyo would add SMS and whether competitors already existed. Both were true and neither stopped Postscript. Obvious objections filter out the ideas everyone else also dismissed, which is where the opening is.
Waiting for the alternative before turning down the known thing
The order is inverted from how it feels safe. Shaan's own formulation is that only when you turn the known thing down do you get the opportunity to find the thing you want. Holding both is what prevents the second from arriving.
Is it for you?
Best for
Operators sitting on a known, safe, time-boxed commitment such as an earn-out, a vesting cliff or a comfortable role that is clearly not the thing they want.
Not ideal for
People whose finances genuinely depend on the guaranteed money, or anyone who has not yet built the skills to generate the alternative options.
From the transcript
“He goes the surface area of opportunity is too wide.”
“Because only when you turn that down then do you get the opportunity to go find the thing you want.”
“You might try to talk yourself into it but like if you're talking yourself into it you're already losing.”
From the episode
Shaan's Story: How I Made My First $1,000,000 By Age 31
Shaan's Story