Risk Stacking
The Era of Compounding Risk
Remember the Atari game Pitfall?
The objective was simple: get from one side to the other without falling into a hole, getting bitten by an alligator, stung by a scorpion or crushed by a rolling log.
Business ownership feels increasingly similar.
The moment you walk out the door and check your first email, you may already be dealing with:
A suspicious link clicked by an employee
A customer threatening legal action
A competitor cutting prices
A new regulation affecting your business
Rising wages and operating costs
An AI tool exposing confidential information
A key employee preparing to leave
And these risks rarely stay in their own lanes.
An attack or mishap can create business interruption, lost revenue, legal exposure and reputational damage in one fell swoop…
61% of risk professionals say business risks are increasing in both velocity and complexity.
That is the real challenge: it is not one alligator, rolling log or black hole.
It is all of them coming at you at the same time.
So why do entrepreneurs continue to do it?
Because we believe the mission is more important than the risk.
Business owners create jobs, solve problems and bring their version of value into the world - despite knowing what could go wrong… Honorable!
Those brave enough to move forward should be celebrated.
They should also be prepared.
That is why I am hosting:
Executive Fireside Chat: AI, Cybersecurity & Business Risk
August 5 | 12:00–1:00 PM PT
We will discuss how today’s technology, cybersecurity and business risks are converging - and what executives can do to better protect their companies.
Join here: https://luma.com/9f3mjfe4 - don’t miss this one!
Poll Results: The results are in from last week’s survey:
60% of voters said AI has made their businesses less secure
Upcoming LinkedIn Live: “5 Fears the Keep Business Owners from Selling”
Sign-up here and see you there!
Movie of the week…
Song of the week…
Tim Martinez — “The Inside Man”
Whenever the time is right here’s 3 ways I can help:
Align your leadership team around a clear strategy
Build systems that scale without adding chaos
Increase the value of your business before a transition or sale
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PS — from time to time a few typos or a broken link may occur, just visit my Substack page for the most up to date version.


