Reflections on my startup journey interweaved with learnings from books (some mentioned) and many awesome people I was fortunate to have worked with.

1. STARTING UP
fight to flight
swamy seetharaman

2. zero to one
turning the flywheel
⁃ flywheel requires persistent effort to
turn
⁃ it starts slow, with effort gets to a
momentum
⁃ if you slow down, you will lose
rhythm and momentum
⁃ if you pause, you may have to start
all over again

3. the hard thing about
hard things
flywheel @ ground zero
⁃ it’s always who first
○ take time & hire tribes without an
any iota of doubt
○ avoid brilliant jerks & familiar loyals
with low competence
○ reverse wrong calls including quickly
and don’t procrastinate in letting go
of people
⁃ make design choices for time to
market & anticipation of future
⁃ make people thirsty & self reliant
with freedom to make decisions
⁃ decentralize decision making
⁃ creatively solve for bandwidth
⁃ ensure, best gets & gives the best

4. crossing the chasm
flywheel @ 90°
⁃ for validating hypothesis, think
shortest possible time with least
amount of resources & barriers
⁃ demos signify progress & a sense of
movement for the team
⁃ bandwidth is worth gold & less
should always lead to more
⁃ with a product market fit, build
foundations of scale so that you can
construct and deconstruct building
blocks on top of it independently
and quickly

5. grinding it out
flywheel @ 180°
⁃ solving elegantly is making pragmatic
choices for a given context without
regressing hygiene
⁃ scars signal skin in the game, war stories
truly narrate grinding
⁃ lens of problem will ensure the problem
stays as problem forever
⁃ pick up trash you see, because no one
else from outside will
⁃ burnout is for real and most times
happen with few
⁃ giant pushes, surprising speed,
surpassing self, honest reflections &
compounding outcomes & having each
other back are signs of progress

6. built to last
flywheel @ 360°
⁃ as you scale introduce process to
communicate, embrace changes &
align better,
⁃ build resilient systems to enable
faster detection and recovery
⁃ from the start instrument everything
wrapping customer journey so that
you can make timely course
corrections
⁃ think tech, data, internal facing tools
and security from day 1
⁃ consciously make time to clear debts
that will be an impediment to future
speed
⁃ ingrain customer empathy in the
culture

8. drive
purpose is the secret sauce
⁃ make your team see the purpose,
thirsty with audacious goals &
enable with freedom with
responsibility
⁃ catch them when they do right
things & guide them when they don’t
⁃ help them to measure, reflect,
improve & compound outcomes
⁃ build psychological safety for
failures
⁃ remember, motivation is vulnerable
to forces of cancellation, what you
may create with so much effort can
disappear in a heartbeat
○ cull forces of cancellation ruthlessly

9. grit
as time, money & bandwidth
shrink
⁃ more people doesn’t result in more
outcomes
○ more of wrong selection actually
results in less outcomes
⁃ a great hire is 2.5X of average hire
⁃ constraints will lead to innovation
⁃ automate for repetitions
⁃ democratize for dependencies
⁃ relentlessly unblock, don’t wait for
problems to magically resolve
⁃ sacrifices happen for purpose not
for immediate rewards

10. tribes
a double edged sword
⁃ empathize with new people more as
the change is a lot more for them
○ it is everyone’s responsibility to
set them up for success
○ they will outnumber initial tribe
& with poor assimilation they
will form their own subcultures
■ most subcultures have
resulted in bad endings
⁃ design environment for new people
to embrace & assimilate the core
values
○ provide them the context on
why certain decisions taken in a
certain way
○ ensure they earn their badges

11. speed of trust
hard to earn, easy to lose
- make every new joinee earn trust
- negative deposits in trust bank will
lead to non linear org debt
⁃ trust promoters
○ consistency, transparency, freedom
of choices, common purpose or
enemy, unthinkable goals, seeking
feedback, taking advice, taking
tough stands
⁃ trust detractors
○ incompetence, passing the buck,
entitlement, asymmetry in words
and actions, lack of
alignment/communication,
inordinate policies and approvals,
negative reinforcements

12. antifragile
- gain from stretches
- you will be stretched, sometimes
intellectually, sometimes
emotionally, sometimes physically
- stretches leads to expansion of mind
- stretches are signs of compounding
- gives a kinesthetic movement
- signals progress
- separates you from your peers
- if you don’t feel stretched, then your
capabilities are likely being
underutilized and you are shrinking
- staying flat over time is
decaying

13. why we sleep
- don’t burn out
- lack of sleep will make you less
productive and more error prone
- for long battles health is a must
- battle wounds need sleep to heal
- equally your responsibility to
recognize burnouts & take breaks
- if only a few in the org experience
burnt out consistently, then signs of
10% of organization carrying 90%.
don’t get there
- work life balance is about enjoying
both work and life, not necessarily
boxing time for it

14. whale done
- catch them when they
do well
- recognize peers generously
- Recognize on time
- competitive spirit is a great
motivator, compete fiercely with
yourself
- with every recognition, bar is set for
you to raise further
- for the next applause you need to
push even more harder
- celebrate and watch out for people
who are do well

15. skin in the game
- you can’t fake it
- scars signal skin in the game
- some companies treat people like
minions, some slaves
- treat your team members like
warriors
- a sign that you are operating in 9/10
zone is when you start (& never
stop) bragging about it to your
friends, spouse, colleagues
- a wartime CEO enables her
employees with guardrails and
weapons so they don’t get their ass
shot off in the battle
- give a great fight

16. all in
- no half assing
- good luck can’t make you great, but
bad luck can kill you
- grow with effectiveness, scale with
efficiency
- hustle, hustle, hustle

17. rule #1, don’t be #2
- obsession to win
- if you really want something, you
will create time for it, you will make
it happen
- relentlessly seek truth
- challenge status quo, question
mediocrity
- customer empathy is something you
can’t hide
- it is either there or not there
- if there is one team that is naturally
positioned to accelerate winning it is
tech and converse also true

18. it’s not luck
- small minds believe in luck
- great minds
- create everything twice, one mental
creation and other physical creation
- will be hungry for problems while
focusing disproportionately on solving
them
- will go to great lengths to persuade,
influence and get what they want
- will anticipate, plan better & get it right
more than others

19. the no complaining
rule
- speak, seek, act
- if you see trash, pickup
- negativity compounds 10X faster than
something positive
- if you speak up, you stand a very good
chance to help solve problems for
yourself and others
- side conversations are magnetic traps &
they will compound the problem not the
solutions

20. the oz principle
- alignment, action,
accountability
- goals and OKRs can’t solve everything
- anticipate better and make right choices
- make yourself and others accountable
- make yourself available at crucial times
- question wrong decisions
- opportunities never self destruct, humans
do and humans can destruct both
themselves and opportunities
- hustle and get shit done

21. “don’t fear failure. not
failure, but low aim, is the
crime. in great attempts it is
glorious even to fail”