Nobody Hires a
Founder
GARRETT DIMON
XO RUBY MONTRÉAL, OCTOBER 2026
Slide 2
Slide 2 text
No content
Slide 3
Slide 3 text
No content
Slide 4
Slide 4 text
No content
Slide 5
Slide 5 text
Range rarely wins a single
opening.
THE BEST FIT FOR ONE ROLE BEATS A GOOD FIT FOR SIX.
Slide 6
Slide 6 text
No content
Slide 7
Slide 7 text
“
Garrett.
That’s the problem. You’re a founder.
Companies don’t hire founders.
A GOOD FRIEND & MENTOR
Slide 8
Slide 8 text
Unlisted, not unqualified.
“DIFFICULT TO DESCRIBE” IS A FEATURE
FEATURE—NOT
NOT A BUG.
Slide 9
Slide 9 text
Your mix is the
opportunity.
AI MAKES BREADTH USEFUL WHERE YOUR INTERESTS OVERLAP.
Slide 10
Slide 10 text
Fear can often be
disguised as being
reasonable.
WHEN THE ONLY STORIES ARE LEAPS, NOT LEAPING FEELS
SENSIBLE.
Slide 11
Slide 11 text
No content
Slide 12
Slide 12 text
No content
Slide 13
Slide 13 text
Recognize gaps and remain
incessantly curious.
THOSE TIMES YOU THINK “YOU HAVE GOT TO BE KIDDING ME.”
Slide 14
Slide 14 text
No content
Slide 15
Slide 15 text
No content
Slide 16
Slide 16 text
Don’t not do the thing.
REGRETS ABOUT NOT DOING SOMETHING ARE THE TOUGHEST.
Slide 17
Slide 17 text
Boring by design.
LOW COSTS AND PART-TIME CONSULTING TO BUY ROOM TO TRY.
Slide 18
Slide 18 text
“
I’m a great believer in luck. The harder
I work, the more of it I seem to have.
COLEMAN COX, 1922
Slide 19
Slide 19 text
“
I’m a great believer in luck. The harder I
work more I share, the more of it I seem to
have.
COLEMAN COX, 1922, EDITED
Slide 20
Slide 20 text
Pay the bills. Buy some time.
KEEP THE INCOME STEADY. GUARD THE TIME FOR THE BET.
Slide 21
Slide 21 text
Adjacent steps, not bold leaps.
IT’S MORE LIKE A GAME OF CONNECTING THE DOTS.
Slide 22
Slide 22 text
No content
Slide 23
Slide 23 text
Should you or shouldn’t you?
WOULD YOU REGRET NOT DOING IT? IS IT LIKELY TO BE USEFUL ANYWAY? ARE YOU
BEING TOO SAFE? TOO RISKY? WILL IT PAY THE BILLS AND BUY TIME?
Slide 24
Slide 24 text
Luck favors the visible.
SHARE WHAT EXCITES YOU, NOT WHAT SELLS.