5 KEY QUESTIONS
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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
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
RESOURCES
Books
Web
• Founder’s Dilemmas by
Noam Wasserman
• Crucial Conversations by
Kerry Patterson
• Startup Life by Brad Feld
and Amy Batchelor
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Quora
99u
AVC by Fred Wilson
Essays by Paul Graham
Feld Thoughts by Brad
Feld
THANKS TO THE ENTREPRENEURS
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Dan Adams
James Altucher
Gihan
Amarasiriwardena
Delian Asparouhov
Fan Bi
David Cancel
Wayne Chang
Anand Dass
Ty Danco
Jeff Engler
Robb Fitzsimmons
Kai Gray
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Jason Jacobs
Cort Johnson
Taariq Lewis
Alex Loijos
Anthony Longo
Evan Morikawa
Christopher Moses
Nick Perold
Kash Razzaghi
Ed Roberts
Christian Rodriguez
Ben Rubin
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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
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.
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
The key elements in the following slides should factor into the conversation about each of the real questions
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.
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)
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.
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?
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?
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?
Remember, the discussion around each question should cover those key elements, otherwise you’re probably overlooking somethingTeamMarketProductTechnologyMoney
MeetupsHackathonsStudent groups
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
TravelMeet people you would not otherwise knowGeek out on things you don’t know much about
Hackathonsproject-based classesResearchIntern at a company in the industry you want to learn about