THE FIVE
QUESTIONS
TO ASK BEFORE
BUILDING A
STARTUP

IAP 2014
WHO ARE WE
Elliot Cohen

R. Colin Kennedy
WHO ARE YOU?
WHAT ARE WE DOING HERE?

Understand how to
build the right thing
with the right people.
AGENDA
o 2 types of questions
o Key elements for a startup
o 5 key questions
o What the experts think
o Where to go next
2 TYPES OF QUESTIONS
QUESTIONS YOU ASK YOURSELF
QUESTIONS YOU ASK OTHERS
AGENDA
o 2 types of questions
o Key elements for a startup
o 5 key questions
o What the experts think
o Where to go next
KEY ELEMENTS FOR A
STARTUP
TEAM
MARKET
PRODUCT
TECHNOLOGY
MONEY
KEY ELEMENTS FOR A STARTUP
•
•
•
•
•

Team
Market
Product
Technology
Money
AGENDA
o 2 types of questions
o Key elements for a startup
o 5 key questions
o What the experts think
o Where to go next
5 KEY QUESTIONS
WHAT DOES SUCCESS LOOK LIKE?
WHO DO WE WANT TO WORK
WITH?
WHAT DO WE WANT TO CREATE IN
THE WORLD?
WHAT’S OUR VISION?
WHAT ARE WE WILLING TO DO TO
GET THERE?
5 KEY QUESTIONS
1.
2.
3.
4.
5.

What does success look like?
Who do we want to work with?
What do we want to create in the world?
What’s our vision?
What are we willing to do to get there?
AGENDA
o 2 types of questions
o Key elements for a startup
o 5 key questions
o What the experts think
o Where to go next
WHAT THE EXPERTS THINK
THE RESEARCH
“What do you wish you’d asked before
starting a company?”
Over 30 responses from serial
entrepreneurs, investors, advisors, & first time
Founders
How do you function when
your feelings are hurt?
Startups are more prone to
hurt feelings and ego
beatings than any place on
earth. Can you still cope
and do the job when your
ego is bruised?
Kai Gray

Do my values and priorities
in life align with the startup
lifestyle?”… or rather, "Can
my lifestyle sustain the
startup 'thing'?”
What does that really MEAN
to each co-founder? Do they
have any idea how HARD it
is, how much they are going
to have to hustle?
Amanda von Goetz
What’s your relationship
history?
Because we are about to be
married
(seriously and I’ve been
married for almost 10
years…)

Dan Adams

Think about the kind of work
that they will be doing NOW
and in 3 Years … is this
person truly knowledgeable
about a specific skill set
necessary for your
company? Are they a pair of
hands?
Gihan Amarasiriwardena
Have you found one person
this product will easily help?

James Altucher

What unique insight do you
have for the specific
problem you are solving?
Why is that insight unique to
you, and why do you believe
that insight to be
true/correct?

Brett van Zuiden
How will the co-founders make
decisions and resolve conflicts
? What are the biggest
decisions you've had to work
through so far ?
The biggest controllable
reason why startups fail is cofounder conflict: the founders
don't figure out a way of
dealing with decisions when
they disagree.

Drew Volpe

If you learned tomorrow that
the exact thing you've
envisioned exists, how
would you react? Would you
run out and buy it? Would
you try to join them? Double
your resolve and try to outcompete them?
Mark Soper
Who are all of the
stakeholders here, and are
we all on the same page?
This includes
founders, investors, advisor
s, and it changes over time
– so you have to revisit the
conversation.
Ty Danco

What’s my risk profile, at my
age? Should I be starting
something vs. taking a
secure paying job?
What I didn't know is that
the learning experience
from being an entrepreneur
will bring tremendous value
to any future job I take.
Alex Loijos
Which one of us gets a boss
first?
ie: who doesn't scale.
Set expectations up
front, be on the same
transparent page… and
things might change
obviously
David Tisch

Is this really the best use of
your time right now?

Delian Asparouhov
Is this a shotgun marriage?
Get to know them first, do
some collaboration together
before becoming official and
see how it feels.

Jason Jacobs

Do you really love our target
customers or are they just
bags of money?

Taariq Lewis
How much do we trust each
other?
Trust is super important. I
wouldn't work with people I
don't trust, can't confide in,
or can't confide in me. You
have to be able to have the
hard conversations -- about
each other,
clients/customers, and
employees.
Jeremy Weiskotten

Do you run toward or run
away from uncertainty?
My opinion is that the
people who relish that
uncertainty - those who view
it as an opportunity to figure
things out in ways others
won't - are the ones who will
thrive.
Jason Shin
What part of our plan are we
each unwilling to change?
Not all startups need to
change their plans during the
course of their evolution. Just
the ones that want to survive
and succeed.
Having said that, there may be
elements of the plan that you
don’t want to change.

Dharmesh Shah

What can we do to test this
now?
There is always a way to
test your value proposition.
Unscalable is fine; just go
out and try to sell your
product before you build it!

Will Whitney
Short of going into the Navy
SEAL program, we are
electing to take on the most
challenging career
possible, do you really want
it that bad? And why?
What are the drivers to
create / own / manage your
own business?
(because it ain't pretty...)
Tony Longo

Do I know anyone who's
currently an entrepreneur
and have I spent an hour
talking with her about what
her life is like?

Jeff Engler
In the triangle of
speed, quality, and cost, do
I have enough resources to
worry only about speed and
quality and not about cost?

Wayne Chang

What do you think is the
relative ownership for me
relative to you?

Ed Roberts
Why now?
Took me 5 startups to finally
figure out the importance of
that question. It should be
repeated/asked as a
mantra.
Why now? Why now?...
David Cancel
AGENDA
o 2 types of questions
o Key elements for a startup
o 5 key questions
o What the experts think
o Where to go next
WHAT’S NEXT FOR YOU?
MEET NEW PEOPLE
READ
EXPLORE
GO AND DO
RESOURCES
Books

Web

• Founder’s Dilemmas by
Noam Wasserman
• Crucial Conversations by
Kerry Patterson
• Startup Life by Brad Feld
and Amy Batchelor

•
•
•
•
•

Quora
99u
AVC by Fred Wilson
Essays by Paul Graham
Feld Thoughts by Brad
Feld
STAY CONNECTED
Elliot

Colin

@elliotcohen

@rcolinkennedy
THANKS TO THE ENTREPRENEURS
•
•
•
•
•
•
•
•
•
•
•
•

Dan Adams
James Altucher
Gihan
Amarasiriwardena
Delian Asparouhov
Fan Bi
David Cancel
Wayne Chang
Anand Dass
Ty Danco
Jeff Engler
Robb Fitzsimmons
Kai Gray

•
•
•
•
•
•
•
•
•
•
•
•

Jason Jacobs
Cort Johnson
Taariq Lewis
Alex Loijos
Anthony Longo
Evan Morikawa
Christopher Moses
Nick Perold
Kash Razzaghi
Ed Roberts
Christian Rodriguez
Ben Rubin

•
•
•
•
•
•
•
•
•
•
•
•

Dharmesh Shah
Jason Shin
Mark Soper
Tyler Spalding
David Tisch
Amanda von Goetz
Brett van Zuiden
Jeremy Weiskotten
Scott Weller
Aaron White
Will Whitney
Drew Volpe
THANKS

Five Questions to Ask Before Building a Startup

  • 1.
    THE FIVE QUESTIONS TO ASKBEFORE BUILDING A STARTUP IAP 2014
  • 2.
    WHO ARE WE ElliotCohen R. Colin Kennedy
  • 3.
  • 4.
    WHAT ARE WEDOING HERE? Understand how to build the right thing with the right people.
  • 5.
    AGENDA o 2 typesof questions o Key elements for a startup o 5 key questions o What the experts think o Where to go next
  • 6.
    2 TYPES OFQUESTIONS
  • 7.
  • 8.
  • 9.
    AGENDA o 2 typesof questions o Key elements for a startup o 5 key questions o What the experts think o Where to go next
  • 10.
  • 11.
  • 12.
  • 13.
  • 14.
  • 15.
  • 16.
    KEY ELEMENTS FORA STARTUP • • • • • Team Market Product Technology Money
  • 17.
    AGENDA o 2 typesof questions o Key elements for a startup o 5 key questions o What the experts think o Where to go next
  • 18.
  • 19.
  • 20.
    WHO DO WEWANT TO WORK WITH?
  • 21.
    WHAT DO WEWANT TO CREATE IN THE WORLD?
  • 22.
  • 23.
    WHAT ARE WEWILLING TO DO TO GET THERE?
  • 24.
    5 KEY QUESTIONS 1. 2. 3. 4. 5. Whatdoes success look like? Who do we want to work with? What do we want to create in the world? What’s our vision? What are we willing to do to get there?
  • 25.
    AGENDA o 2 typesof questions o Key elements for a startup o 5 key questions o What the experts think o Where to go next
  • 26.
  • 27.
    THE RESEARCH “What doyou wish you’d asked before starting a company?” Over 30 responses from serial entrepreneurs, investors, advisors, & first time Founders
  • 28.
    How do youfunction when your feelings are hurt? Startups are more prone to hurt feelings and ego beatings than any place on earth. Can you still cope and do the job when your ego is bruised? Kai Gray Do my values and priorities in life align with the startup lifestyle?”… or rather, "Can my lifestyle sustain the startup 'thing'?” What does that really MEAN to each co-founder? Do they have any idea how HARD it is, how much they are going to have to hustle? Amanda von Goetz
  • 29.
    What’s your relationship history? Becausewe are about to be married (seriously and I’ve been married for almost 10 years…) Dan Adams Think about the kind of work that they will be doing NOW and in 3 Years … is this person truly knowledgeable about a specific skill set necessary for your company? Are they a pair of hands? Gihan Amarasiriwardena
  • 30.
    Have you foundone person this product will easily help? James Altucher What unique insight do you have for the specific problem you are solving? Why is that insight unique to you, and why do you believe that insight to be true/correct? Brett van Zuiden
  • 31.
    How will theco-founders make decisions and resolve conflicts ? What are the biggest decisions you've had to work through so far ? The biggest controllable reason why startups fail is cofounder conflict: the founders don't figure out a way of dealing with decisions when they disagree. Drew Volpe If you learned tomorrow that the exact thing you've envisioned exists, how would you react? Would you run out and buy it? Would you try to join them? Double your resolve and try to outcompete them? Mark Soper
  • 32.
    Who are allof the stakeholders here, and are we all on the same page? This includes founders, investors, advisor s, and it changes over time – so you have to revisit the conversation. Ty Danco What’s my risk profile, at my age? Should I be starting something vs. taking a secure paying job? What I didn't know is that the learning experience from being an entrepreneur will bring tremendous value to any future job I take. Alex Loijos
  • 33.
    Which one ofus gets a boss first? ie: who doesn't scale. Set expectations up front, be on the same transparent page… and things might change obviously David Tisch Is this really the best use of your time right now? Delian Asparouhov
  • 34.
    Is this ashotgun marriage? Get to know them first, do some collaboration together before becoming official and see how it feels. Jason Jacobs Do you really love our target customers or are they just bags of money? Taariq Lewis
  • 35.
    How much dowe trust each other? Trust is super important. I wouldn't work with people I don't trust, can't confide in, or can't confide in me. You have to be able to have the hard conversations -- about each other, clients/customers, and employees. Jeremy Weiskotten Do you run toward or run away from uncertainty? My opinion is that the people who relish that uncertainty - those who view it as an opportunity to figure things out in ways others won't - are the ones who will thrive. Jason Shin
  • 36.
    What part ofour plan are we each unwilling to change? Not all startups need to change their plans during the course of their evolution. Just the ones that want to survive and succeed. Having said that, there may be elements of the plan that you don’t want to change. Dharmesh Shah What can we do to test this now? There is always a way to test your value proposition. Unscalable is fine; just go out and try to sell your product before you build it! Will Whitney
  • 37.
    Short of goinginto the Navy SEAL program, we are electing to take on the most challenging career possible, do you really want it that bad? And why? What are the drivers to create / own / manage your own business? (because it ain't pretty...) Tony Longo Do I know anyone who's currently an entrepreneur and have I spent an hour talking with her about what her life is like? Jeff Engler
  • 38.
    In the triangleof speed, quality, and cost, do I have enough resources to worry only about speed and quality and not about cost? Wayne Chang What do you think is the relative ownership for me relative to you? Ed Roberts
  • 39.
    Why now? Took me5 startups to finally figure out the importance of that question. It should be repeated/asked as a mantra. Why now? Why now?... David Cancel
  • 40.
    AGENDA o 2 typesof questions o Key elements for a startup o 5 key questions o What the experts think o Where to go next
  • 41.
  • 42.
  • 43.
  • 44.
  • 45.
  • 46.
    RESOURCES Books Web • Founder’s Dilemmasby Noam Wasserman • Crucial Conversations by Kerry Patterson • Startup Life by Brad Feld and Amy Batchelor • • • • • Quora 99u AVC by Fred Wilson Essays by Paul Graham Feld Thoughts by Brad Feld
  • 47.
  • 48.
    THANKS TO THEENTREPRENEURS • • • • • • • • • • • • Dan Adams James Altucher Gihan Amarasiriwardena Delian Asparouhov Fan Bi David Cancel Wayne Chang Anand Dass Ty Danco Jeff Engler Robb Fitzsimmons Kai Gray • • • • • • • • • • • • Jason Jacobs Cort Johnson Taariq Lewis Alex Loijos Anthony Longo Evan Morikawa Christopher Moses Nick Perold Kash Razzaghi Ed Roberts Christian Rodriguez Ben Rubin • • • • • • • • • • • • Dharmesh Shah Jason Shin Mark Soper Tyler Spalding David Tisch Amanda von Goetz Brett van Zuiden Jeremy Weiskotten Scott Weller Aaron White Will Whitney Drew Volpe
  • 49.

Editor's Notes

  • #3 Elliot began his career as a software engineer and product manager at Microsoft and a series of small startups. He later joined the Trust Center for Entrepreneurship as a Program Manager before earning an MBA at MIT Sloan. While at the Trust Center and later as a student at Sloan he helped co-found MIT's Hacking Medicine which is now in its 3rd year and has been the source of a number of new ventures in healthcare. He is now the co-founder and CTO of PillPack - a simple, hassle-free pharmacy.Colin took over for Elliot after a year as Founder of a small startup. Prior to that, he was on the founding team of Randstad Corporate Services, an enterprise solutions division of one of the largest HR firms in the world.While working at MIT he launched the class Applications on Advanced Entrepreneurship with Professor Aulet, the HackingIAP program, ran the Silicon Valley Study Tour for E&I, and launched the first Founders skills Accelerator (FSA).He recently left MIT to spend more time working on a web venture called Fitgiver, which helps people raise sponsorship money for cancer research with their everyday workouts.
  • #4 How many are not from MITHow many are undergradHow many in Engineering?How many in Business?How any have been involved in a startup?How many want to start a company someday?Introduce yourself to your neighbor
  • #11 The key elements in the following slides should factor into the conversation about each of the real questions
  • #16 Related points:CompensationFunding: Bootstrapping or raising money?Personal runway: Can you afford to fail? Do you have market value and can get back on your feet quickly.
  • #20 10 min of discussion, 5 per person. Role play. One talks, the other asks clarifying questions.5 min to share as a larger group, who was most surprised about where they landed at the end of their 5 min?Related points:Why are you doing this ?You have to have a fear of failure to grind it out but you also have to optimize to win, not optimize not to lose.What does success look like to you? Is it a $3M home you can ball in, is it a $500k a year paycheck, is it working with a team you love, is it building products you're passionate about. Do you want to be Rich or be King? (Founders Dilemma)
  • #21 5 min of discussion - what skills should they have? What values? etc.2 min of sharing as a groupRelated points:Is my cofounder amazing at the things I’m not? Am I amazing at the things he’s not? What do you expect to work on day-to-day?What unique advantage does your team have that will make it win this market ? If we don’t have that yet, how do we find it? Who does that look like?Any reservations or concerns regarding your co-founders? They only get amplified when the stress level rises.Not just are you a day or night person, number of hours you work in a week, etc. (which are all important) but also what you're like to be on a team with.dont do a shotgun marriage. get to know them first, do somecollaboration together before becoming official and see how it feels.
  • #22 5 min of discussion - some examples of things you’d like to create in the world / identifying how important this is to you?2 min of sharing as a groupRelated points:Is it worth doing? How much is this going to improve my customers' lives?
  • #23 5 min of discussion – what’s your vision for getting to the thing you want to create?2 min of sharing as a groupWhat does vision mean to you?How do you make sure you share the same perspective?
  • #24 5 min of discussion - talk about raising money or not, going without salary, how committed you are to making this the central thing in your life?2 min of sharing as a groupDiscussion pointsDo you like Ramen?What outside of work do you need to feel fulfilled?
  • #25 Remember, the discussion around each question should cover those key elements, otherwise you’re probably overlooking somethingTeamMarketProductTechnologyMoney
  • #43 MeetupsHackathonsStudent groups
  • #44 Founder’s Dilemmas by Noam WassermanCrucial Conversations by Kerry PattersonStartup Life by Brad Feld and Amy BatchelorAVC by Fred Wilson (blog)Essays by Paul GrahamFeld Thoughts by Brad Feld
  • #45 TravelMeet people you would not otherwise knowGeek out on things you don’t know much about
  • #46 Hackathonsproject-based classesResearchIntern at a company in the industry you want to learn about