In this presentation, created for MIT's Integrated Design & Management (IDM) program, I cover some of my lessons learned from past jobs. Topics include startups, entrepreneurship, recruiting / team-building, a little bit of angel investing and advisory, and a couple of case studies.

1. PRINCIPLES OF INTEGRATED DESIGN
Yoav Shapira / May 2016

2. WHAT HAVE I DONE?!?
Yoav Shapira / May 2016

3. OBLIGATORY BACKGROUND
• Software engineer -> product + eng ->
company builder
• Started in Big Consulting, then medium-
size pharma
• Serial entrepreneur: built and ran product/
engineering @CarGurus, @HubSpot,
@Happier, @Jana
• Advisor / investor in numerous companies
• Occasional slow runner, weird sports
enthusiast
• Get in touch: www.YoavShapira.com

4. PLEASE
INTERRUPT.
I don’t like hearing myself talk.

5. STARTUP1, DAY 1
• Imagine a nice late winter
morning in the Harvard
Square Starbucks
• Me:“I’m excited, let’s go to
the office!”
• CEO:“Great idea! We need
an office! Where would you
like to work?”

6. CLEAN CANVAS
• I quickly learned about commercial
real estate, leases, insurance.
• Bought and personally assembled a
handful of IKEA desks.
• I don’t like assembling furniture. But I
like starting companies from scratch
because…
• You create the culture, the values, the
norms from day 1.
• These matter more than product or
go-to-market.They are your company.

7. SCRAPPINESS
• A trait that I (and others) value highly.
• Equally important whether hiring
colleagues or investing in founding
teams.
• Scrappy does the best s/he can with
limited resources (it’s a startup) without
complaining.
• At scale, sometimes scrappy needs a
new challenge or a replacement.This is a
good problem to have.
• With an MIT (or similar) degree, you
may need to prove you’re scrappy (still).

8. SUSTAINABLE ADVANTAGES
• Remember that nearly
anything about a product
can be copied, often quickly.
• Code, user interfaces are
competitive advantages,
maybe, but usually not
sustainable.
• Speed of learning / iteration,
however, is sustainable.

9. SPEED WINS
• Construct your culture,
including every process, to
minimize time through the
loop.
• Learn about user research,
split testing, etc, but also look
hard at internal processes.
• Meetings, especially, are
insidious time sucks.

10. WORTHTHEIR OWN SLIDE
• Time is the only true zero-sum game.
You can’t “grow the pie.”
• Be ruthless about it, but clear,
consistent.
• Can you share knowledge
asynchronously, e.g. via a wiki?
• Note: I’m talking about regular /
recurring meetings.Ad-hoc time at a
whiteboard / similar is excellent,
encouraged.
• “Long twitch” vs “slow twitch” time

11. “I AM NOT A DESIGNER”
• “I’m not a designer because I can’t draw
anything.” That’s overly simplistic, naive.
• Meetings, for instance, are designing
people’s time, calendars, schedule.
• How do you react to a late Friday
evening or early Monday morning
meeting invitation?
• You will all be designing things at a
startup: products, user experiences, etc.
• Just that the “user” might be a colleague,
a job candidate, an external partner…

12. LEARNTHE CRAFT
• Spend time chatting with actual
designers and other specialists.
• Shadowing (or actual
apprenticeship!) is under-rated in
general.
• Take a support call, try to sell, do a
user interview, build a screen, run
a web split test, buy an ad…
• You don’t need to master the skill.
Specialists still have value. But
know enough to be credible, hire.

13. “LEVEL 5 LEADERSHIP”
• Jim Collins “Good to Great”
concept. Maybe best part of
book. (Much has aged poorly.)
• Read the whole definition, In
particular:
• Set the target at building an
enduring, world-class company
• When giving credit, look
outside the window; when
blaming, look in the mirror.

14. FINDYOURTEAMMATES
• I joined CarGurus and HubSpot for
people, not ideas.
• I’m OK with cars, OK with
marketing people like, but neither
was a passion or life-long interest
• I joined Happier and Jana for
missions more than people.
• Missions don’t have bad days, but
companies and people do.
• If I had to pick one, it’s people first.

15. TYPE II FUN?
• Every single startup has many
days where it feels like it’s going to
die.
• Some have wildly positive days,
too.
• The rare successful one is a
guaranteed rollercoaster.
• Don’t look for stability.
• Don’t do it because it’s this
decade’s sexy job.

16. DATA FOR DEBATE, SUNSHINE

17. HIRING
• Everyone’s job & potential
sustainable competitive advantage.
• Here, too, speed wins: pick target
# total days per candidate, make it
happen.
• Again data: track your funnel
meticulously, split-test sources, ads.
• It’s hard, takes a long time.
• Religion, Pied Piper, etc.

18. RIDINGTHE ROCKETSHIP
• If you’re lucky and the company
is growing, things will break
often.
• Separate “high quality” or
“good” problems from bad
ones.
• Question conventional wisdom.
Even old problems can be fixed
in new ways.
• “Stay hungry, stay foolish.”

19. SMALL,AUTONOMOUSTEAMS
• As small and autonomous as possible, so
they can move forward unhindered.
• Avoid inter-team dependencies as much
as you can.They shackle everyone.
• Don’t just have a designer, engineer, and
“business person.”
• Include whoever is generating revenue
(e.g. sales), whoever is marketing,
whoever is supporting the product,
etc.
• At scale: Spotify’s squads maybe?
• Avoid “conventional” shared service teams

20. AUTONOMY, MASTERY,
PURPOSE
• Watch Daniel Pink’sTEDTalk
or short video.
• This is the key to hiring and
retaining the best people.
• Design your organization
accordingly, be it a team,
department, division, or
entire company.
• Example: OKRs, budgets

22. SMALL, QUICK STEPS
• Ship (software, processes,
and anything else you can)
all the time.
• Continuous Delivery is
magic.
• Forces the entire
organization to have
efficient processes and
culture.

23. PAY IT FORWARD
• The entrepreneurial
community is huge, active,
and welcoming. Reach out!
• Help people however you
can. It takes time, and it’s
not always fun, but they
remember.
• It’s also a small world.
Reputation / karma matters.

24. FINALLY: BETRUETO
YOURSELF
• Do what it takes to sleep well
at night: a clear conscience is
key.
• Don’t compromise on your
values, be they personal or
professional.
• When you do this consistently,
you have zero regrets.
• This sounds cheesy, but it’s
been crucial to me.

26. QUIKFORCE (THANKS
@KEVIN)
• “Hiring movers has never
been easier.”
• Simple site + app to describe
your move, book movers
quickly and easily.
• Rapid B2C growth, now
receive B2B interest from
corporate movers.
• Thoughts?

27. JANA (THANKS @KEVIN)
• A current challenges: portal vs
constellation.
• Jana’s mission is to make the
internet free for the next billion.
• Users in emerging markets, e.g.
India, with (low end)
smartphones.
• Browsing, messaging, photos, apps:
make free in one place?
• “Chinese Mobile App UITrends”