The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture

411 Pages·2018·17.84 MB·English

by  Scott Belsky

PRAISE FOR THE MESSY MIDDLE
“This is required reading for founders. Experienced entrepreneurs all know this
period Scott refers to as ‘the messy middle’ and a few of us have worked our
way out of it, but this is the first time I’ve seen an expert—both as a founder and
as an investor—break down in such detail just how to endure, optimize, and
make it through.”
—ALEXIS OHANIAN, cofounder of Initialized Capital and Reddit “Scott Belsky
is a master of generous work worth doing. The Messy Middle will help
you see that you have more control than you dare to admit, and the
ability to make a difference if you care enough.”
—SETH GODIN, author of Linchpin
“Building a lasting business is 1 percent idea and 99 percent resilience. The
Messy Middle details the unglamorous but essential lessons every founder needs
to learn.”
—JENNIFER HYMAN, cofounder and CEO, Rent The Runway
“Starting a new venture is like jumping off a cliff and sewing a parachute on the
way down. This book is the parachute.”
—JOE GEBBIA, cofounder and chief product officer, Airbnb
“Having been through the ups and downs of the messy middle many times, it’s
critical to understand the challenges ahead. This insightful book empowers you
to approach them head-on. Belsky’s powerful tool kit, based on hard-earned
experiences, is an essential guide to building a compelling product,
revolutionizing an organization, or growing your leadership abilities.”
—TONY FADELL, inventor of the iPod, coinventor of the iPhone, founder and
former CEO of Nest, principal at Future Shape

Portfolio/Penguin An imprint of Penguin Random House LLC
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New York, New York 10014
Copyright © 2018 by Scott Belsky
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ISBN: 9780735218079 (hardcover) ISBN: 9780735218086 (ebook)
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time of publication, neither the publisher nor the author assumes any responsibility for errors or for changes that occur after
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websites or their content.
Version_1
With gratitude to Erica, Chloe, and Miles for helping me make the most of my
middle.

CONTENTS
• • •
PRAISE
TITLE PAGE
COPYRIGHT
DEDICATION
THE MESSY MIDDLE
INTRODUCTION
It’s not about the start and finish, it’s about the journey in between.
The stories fall short.
Start, endure, optimize, finish, then repeat.
ENDURE
LEADING THROUGH THE ANGUISH AND THE UNKNOWN
Short-circuit your reward system.
Don’t seek positive feedback or celebrate fake wins at the expense of
hard truths.
Accept the burden of processing uncertainty.
Fight resistance with a commitment to suffering.
Friction brings us closer.
Be the steward of perspective.
Leave every conversation with energy.
If you don’t like the way government is being run, cross party lines.
DYFJ. Do your fucking job.
STRENGTHENING YOUR RESOLVE
The only “sustainable competitive advantage” in business is self-
awareness.
Nobody remembers, or is inspired by, anything that fits in.
Take a dose of OBECALP and suspend your disbeliefs in yourself.
Attempt a new perspective of it before you quit it.
To create what will be, you must remove yourself from the constant
concern for what already is.
Prompt clarity with questions.
Sometimes a reset is the only way forward.
EMBRACING THE LONG GAME
Playing the long game requires moves that don’t map to traditional
measures of productivity.
Strategy is nourished by patience.
Break the long game down into chapters.
Just stay alive long enough to become an expert.
Do the work regardless of whose work it is.
OPTIMIZE
OPTIMIZING YOUR TEAM
BUILDING, HIRING, AND FIRING
Resourcefulness > Resources
Initiative > Experience
Diversity drives differentiation.
Hire people who have endured adversity.
Seek people with whom discussions evolve by a step function.
If you avoid folks who are polarizing, you avoid bold outcomes.
Cultivate your team’s immune system, and occasionally suppress it.
Grafting talent is just as important as recruiting talent.
Foster apprenticeship.
Shed the bad to keep the good.
A steady state is unsustainable; keep people moving.
CULTURE, TOOLS, AND SPACE
Culture is created through the stories your team tells.
Accommodate free radicals.
Be frugal with everything except your bed, your chair, your space, and
your team.
The products you use to create impact the products you create.
Attribute the right amount of credit to the right people.
STRUCTURE AND COMMUNICATION
When you have the right people, there are no rules for structure.
Process is the excretion of misalignment.
Don’t rob people of their process.
Merchandise to capture and keep your team’s attention.
A mock-up > Any other method of sharing your vision
Present your ideas, don’t promote them.
Delegate, entrust, debrief, and repeat.
Know how and when to say it.
Nothing beats explicitness. Aspire to say it like it is.
There is power in brevity.
CLEARING THE PATH TO SOLUTIONS
Tackle “organizational debt.”
A lot of big problems don’t get solved because we can solve small
problems faster.
Break bureaucracy by piercing ambiguity with questions.
Conflict avoidance stalls progress.
Channel competitive energy.
Creative block is the consequence of avoiding the truth.
Moving fast is great, so long as you slow down at every turn.
Value the merits of slow cooking.
“Ask for forgiveness, not permission.”
Conviction > Consensus
Don’t give those resistant to change false hope.
OPTIMIZING PRODUCT
SIMPLIFYING AND ITERATING