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Hi!
Three Mistakes that
Defined Our Business
http://wi.st/threemistakes
I was wrong
Things I wish I’d known before
scaling from 20 to 100 people
You’ve hired the best
Guiding Assumption
There is no time to think
Big problems are scarier
Communication gets harder
Scaling Challenges
Communication gets harder
Scaling Challenge
Communicate:
New goals for the year
“When are you going to send
out the finished goals?”
If it feels unfinished,
it is unfinished.
Challenge:
All of our teams were on
different schedules
Communicate:
Try to get all teams on the same
schedule
The Operating System
Basecamp Summit
Planning
Retros
Form teams
1 week 4 weeks
Execute with your team
Demos to finish so everyone sees
progress
“Why are you changing
everything? What the F*&K?”
We made the same mistake again!
We got the tone wrong.
Mountaineering
Basecamp
1 week
Preparing for the next climb:
Monitoring the weather
Reviewing past climbs
Learning from other groups
Letting off steam
Revisit overall processes
Summits
4 weeks
Goals for summits:
Laying ropes
Acclimatizing
Rigging ladders
Dropping off oxygen for future climbs
Hike
Ed Viesturs
• 1st American to summit all 14, 8,000M peaks
• Saved people in the infamous Everest

season of 1996 (Into Thin Air)
• Once hiked with Chris & Brendan
œ
Made the communication less serious,
which let people try the operating
system
The tone is the message
Big problems are scarier
Scaling Challenges
As the company grows,
so does the impact of decisions
You want the answers
Before you communicate
Problem:
Pricing
Pricing Testing
$25/month
Unlimited videos
0
19
37
56
74
Gross Margin
Secretly solve the problem
Eureka!
We have to raise prices
The team hated the solution
We formed a
new team to own the
problem.
The solved the problem
openly
Problem:
Changing how we set strategy
Solve big problems openly
Lesson
There is no time to think
Scaling Challenges
It’s my job to be busy
Work Life Unbalanced
I forgot that
thinking is work
Running a company
is a creative endeavor
Solving communication challenges
Making decisions around pricing
Building a more diverse workforce
You need to see thinking as real
work
Getting free time is hard
Being busy is a people problem
not a productivity problem
Delegate more
Get better people
Hackathons
Everyone needs
time to think and create
Don’t feel guilty having free time
Lesson
Focus on tone
Solve big problems openly
Don’t feel guilty having free
time
Thanks!

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