1. The document discusses the author's experience and lessons learned from founding Drop.io, a file sharing startup, after graduating college and working at other companies and projects. 2. It describes the path that led to creating Drop.io, including identifying the problem of privately sharing information, building an initial version in four weeks, and raising funding. 3. Key lessons discussed include that entrepreneurship involves a different type of stress, the importance of caring deeply and surrounding yourself with great people, building solutions in a small and variable way, and focusing on what interests you over chasing the market.

1. lessons from the ‘real’ world
ACM-ICPC Programming Contest Discussion

2. Some perspective:
1. 3.5 years out of college
2. 1 year from founding drop.io
3. Not on a victory lap (yet?)

3. All I can offer is a view from the
trenches…
+ just a few years where you are now.

4. 1. My personal frame of
reference
2. The course of events that
lead to drop.io today
3. A few preliminary lessons

5. 12 years of tinkering…
1. Zoltar (middle school)
2. Six Degrees (highscool)
3. LifeCapital (highscool – college)
4. CrimsonXchange (college)
5. Facebook (college)
6. Kinjunction (college & post college)
7. Essembly  Causes (post college)
8. Bain (post college)

6. Pure theory and academics
1. Foucault
2. Habermas
3. Hayek
4. Locke
5. Rousseau
6. Claude Shannon
7. etc…

7. People & conversation
1. Teachers/Professors/Mentors
2. Friends
3. Real Friends  FOF

8. leading to a few theses that gets
me out of bed…

9. Pure theory: Value of information is
inversely related to how probable it is…
price
s
Your only photo of mom
millionth photo of baby
d
quantity

10. Historical context: For the first time
in history publicity is a negative cost
cost
security privacy
future
all of human history
~2005
publicity
~years

11. People are missing the ball:
Privacy isn’t dead
Privacy isn’t Security
Authorization isn’t Authentication

12. And tech is creating openings:
1. commodity computing
2. the ‘cloud’
3. rapid development practices
070604-STH-Overview-v10 Official 12
This information is confidential and property of Drop.io, Inc
Drop.io, Inc

13. 2. The course of events that
lead to drop.io…

14. Identified the tangible problem:
Spring of 2007
at bain… how do I privately share
information! why is this so hard!

15. A framework to solve it
Simple Private Sharing
No social, no search, no identity
Strip metadata
Create single private points of exchange

16. In a manageable footprint
Inputs
Authorization
Outputs
Users ‘lifehack’ their specific solutions on
top of us

17. Left Job, Built V1:
four weeks

18. F.U.N.D.S: lower investor risk =
better deal
RRE Ventures: $1.2 M seed in Nov
RRE + DFJ: $2.7 M A1 in March

19. Motive Power (from 2 up to 14)
1. smart
2. problem solvers
3. driven
4. intersted in our thesis
5. ‘team’ players
6. (skills)

20. Grow

21. Create a virtuous cycle
Hire Great People
Expand Scope
Raise Capital
VALUE
DEVELOP
(core innovaiton)

22. Upgrade & Innovate (this month)
1. Going 100% into the cloud = huge
new options
2. ‘Switchboard’ API – allowing you to
leverage all our outputs and inputs for your
apps
3. Redesign - for more flexible front end
vocabulary and use
4. Much more…

23. 3. A few preliminary lessons
(which might be useful?)

24. Entrepreneurship is a whole
different type of stress…
Can’t express it – you have to experience it, but
be ready for it
Don’t jump in lightly

25. Tendency towards disequilibrium
Success breeds more success
failure breeds failure
Set yourself up to succeed in the
short term & cycle up

26. Team is everything
Only work with people you respect
People in context of team is different than vaccum
Be involved with great people

27. Build small & variable
small = understandable & manageable
variable = acknowledge you are likely wrong
stay compact

28. You MUST CARE to act
Too much work, too manic not to
If you & your team don’t care
you will fail

29. This room is well positioned
Signaling
Frameworks for learning and thinking
Specific language knowledge is over-rated
Don’t sweat the market, do what
intrests you

30. If what we are working on
interests you: sam@dropio.com
If the theory interests you:
drop.io/swl, twitter/lessin
If entreprenuriship: come drop by
our office for a coffee…
If not: hope the food is good and good
luck!