Ryan Holiday is a strategist and author who dropped out of college to apprentice with Robert Greene and later became the director of marketing for American Apparel. He emphasizes the importance of unique personal experience over competition and advocates for daily habits like running and reading. Holiday also shares his belief in the value of standing for meaningful principles and views obstacles as opportunities for growth.

1. Marketer. Author. Entrepreneur.
B I G F I S H P R E S E N T A T I O N S . C O M
Interview Series
6 QUESTIONS WITH
RYAN HOLIDAY

2. Ryanis a
strategist and
writer
He dropped out of college at nineteen to apprentice under
Robert Greene, author of The 48 Laws of Power, and later
served as the director of marketing for American Apparel.
His company, Brass Check, has advised clients like
Google, TASER, and Complex, as well as many prominent
bestselling authors. Holiday has written six books, most
recently The Obstacle Is the Way.

3. The world’s greatest presenters and where they stand,
on and off the stage.
(noun) /stans/
the attitude of a person or organization toward something; a
standpoint.

4. When youwalkinto a room,
howdoyoumake yourself
stand out?
Question:

5. “In some respects,
I’d rather not stand
out.
Still, from a business perspective I understand
the value.
Answer (1/2):
So take a conference for example. As an introverted
person, I’m not exactly thrilled at having to walk up and
try to awkwardly meet people. I think one of the reasons
I’ve tried to channel my energy into the books that I’ve
written is that their reputation precedes me. “

6. “As a relatively introvertedperson,
standing outis not actually
something I thinkaboutmuch.
So at a conference, I’m not wandering the halls. I’m entering
the stage and being introduced to people that way. Then later,
if there is someone I might want to meet the whole process is
easier. To me this is a different strategy rather than a set of
tactics for how to stand out.”
Answer (2/2):

7. In a time where somany
people are trying to jump
into competition, howdoyou
stayoutof it?
Question:

8. “It’s the bestway to
avoid competition.
I always try to do the things that only I can do.
Only I can write about my own experiences, or
speak authoritatively about the case studies I have
created or the new connections or insights I’ve
made. I don’t want to be better than other people,
I’d rather be the only one doing it.”
Answer:

9. What’s onehabit
that youthink
everyone should
make?
Question:

10. “Run.
Read.
Walk.
Everyday.”
Answer:

11. What'sa belief of
yours thatothers
may challengeyou
on?
Question:

12. “If you’rewriting a book to be a
business card, you’re wasting
yourtime and the world’s time.
You should stop."
Answer:

13. What's a quote that
empowers youto
pullthrough tough
times?
Question:

14. The impediment to action
advancesaction. What
stands in the way becomes
the way.”
“
— Marcus Aurelius
Answer (1/2):

15. Ryan:
“Ok.Nowwhat?
Answer (2/2):
Things are going to happen to us that we’d rather not have
happened. Ok. Now what? All we control is how we respond. We
have the ability to turn this into something positive or different
or new if we so choose. That’s the formula for life right there in
my opinion."

16. Everyone standsfor
something, whatdoyou
stand for?
Question:

17. “First off,
that’snot remotelytrue.
Most people stand for nothing. Or worse, they stand
for everything and think it’s something—when really
that’s nothing too.
I’m very lucky in that my career is about saying what I stand
for. It’s in my books. Many thousands of words on it. I think
ego is toxic, I think media is broken, I think obstacles can be
opportunities, and I think too many people fritter their time
away on ephemeral things. I try to present my solutions for
those things too but I’m not shy about my opinions and
beliefs.”

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