No-Downside Outreach Rule
Take the small bet when rejection leaves your position unchanged
- Difficulty
- Starter
- Time to result
- ~days to results
- Steps
- 5
- Confidence
- 90%
Grover's early route to Michael Jordan illustrates a simple asymmetric decision rule. He saw an article saying Jordan wanted to become stronger, recognised that he had relevant training knowledge but no professional-athlete track record, and mailed letters to 14 other Chicago Bulls players. His reasoning was that the attempt cost only stamps and that silence would leave him in the same job and position. One letter reached Jordan indirectly through another player's locker. The transferable mechanism is to compare the bounded cost of a relevant attempt with the cost of doing nothing, then act when rejection preserves the status quo and the possible upside is meaningful.
Origin
Grover developed this logic while working at a local health club. After reading that Michael Jordan wanted to get stronger, he sent 14 letters to Jordan's teammates; Jordan found one and asked team staff to investigate Grover's approach.
Core principles
- 01A low-cost attempt can have asymmetric upside
- 02Rejection is less costly when it preserves the status quo
- 03Specific relevance beats indiscriminate access seeking
- 04Action creates routes that credentials alone may not
How to run it
- 1
Spot a relevant opening
Find evidence that a person or organisation has a problem your experience could credibly address.
Pro tip Anchor the approach to a stated need rather than a generic request for attention.
- 2
Measure the downside
Ask what rejection, silence, or a failed attempt would actually change in your current position.
Pro tip Count time, money, reputation, and opportunity cost rather than assuming the bet is free.
Watch out Low financial cost does not excuse intrusive or misleading outreach.
- 3
Choose the route
Identify a legitimate channel and the people most plausibly connected to the opportunity.
Pro tip Grover approached adjacent team members because direct digital access did not exist.
- 4
Make the case
Briefly explain the relevant background, philosophy, and potential value you can contribute.
Pro tip Offer enough substance for the recipient to investigate further.
- 5
Send and release
Take the bounded action, then continue working rather than treating a response as owed.
Watch out Do not confuse persistence with repeated unwanted contact.
In the wild
Grover wrote 14 letters describing his background and training philosophy, deliberately addressing Bulls players other than Jordan because he assumed the star would not hire someone without professional-athlete experience. Jordan found one in another player's locker and passed it to team staff.
→ A low-cost outreach attempt opened the path to Grover working with Jordan.
Common mistakes
Calling every gamble free
The rule only applies after honestly accounting for time, money, reputation, and consent.
Sending a generic pitch
Grover connected his background and philosophy to a publicly described performance need.
Is it for you?
Best for
It is best for targeted career, partnership, client, or mentor outreach with limited financial and reputational downside.
Not ideal for
It is not ideal for spam, deceptive pitches, or high-stakes approaches where rejection carries a material cost.
From the transcript
“what's the worst thing that could have possibly happened i'd be in the exact same situation i was in”
From the episode
The Man Who Coached Michael Jordan AND Kobe Bryant To WIN!: Tim Grover