Workshop held for startup founders and executives for Fall 2014 cohort at MACH37™, a vertical accelerator focused on information security product companies. In this workshop, I shared with the attendees, excerpts of my unique experience from four prior startup businesses interleaved with my public company experiences of building durable products that have a long life span, often outliving multiple mergers, acquisitions and change of control in businesses that own the asset.

1. BUILDING DURABLE
SOFTWARE IN STARTUPS
dchakravarty@gmp4.hbs.edu

2. Topics
HIRING
 Why hiring=culture≠teams
 When to make R&D hires
 What to keep in mind when
hiring
 What to look for in R&D hires
 Where to find your Dev wings
DEV BED
 Staff with fixed + var cost
 Create an elastic dev bed
 Use DevOps model, not IT
 Pivot on Teams, not Dev+Test
PRODUCT
 Who to build For & With
 What technologies
What to build With
What platforms to build on
Where to begin building Sw
How much (little) to build
DELIVERY
 What to expect in POCs
 Top 3 hurdles for CTO/VP
 Top 3 hurdles for engineers
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Dipto Chakravarty, Copyright (c) 2014

3. Hire=Culture; Hire≠Team
 Aptitude to deal with uncertainty
 Technology-agnostic point of views
 Generalist broad spectrum vs. specialty
 Tenacity
 Resilience
 Persistence
Your first 3 hires sets
the tone for the team
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Dipto Chakravarty, Copyright (c) 2014

4. When to Make Which Hires
Phase 0
1. Hire the Product Owner role in the beginning
2. On board the Designer, i.e UX and UI owner
3. Onboard the Test Architect and the Dev Architect
4. Create a 3-person nucleus first
Phase 1
1. Construct your MVP with a 3-person team
2. Hire developers and testers, keeping <3:1 ratio
3. Hire DevOps to automate the infrastructure
4. Hire in dual time zones
Hire slow in Phase 0.
Hire steady in Phase 1.
Hire fast in Phase 2…n
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Dipto Chakravarty, Copyright (c) 2014

5. What to Keep in Mind When Hiring
 Avoid hiring technologists; instead, hire
engineers
 Hire for attitude and resilience, then for skills
 Create a fixed plus variable cost hiring model
to aid in an elastic team
 Hire team mates who are good listeners …
can travel if/when needed
work flexible hours
Attitude trumps Skills
for hiring in lean
startups
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Dipto Chakravarty, Copyright (c) 2014

6. What to Look for in Technical
Hire
Soft Skills Hard Skills
 “Getting it” vs. “Getting it
done”
 Distributed teamwork
experience
 Makers vs. Managers
 Doers vs. Inspectors
 Listeners vs. Talkers
 Technology stack agnostic
 Generalists vs. specialists
 Front-end vs. back-end
 Platform vs. Applications
 Framework vs. Plug-in
“It is hard to find soft skills, and simple to find hard skills in software startups”
The soft part is the
hard part in software
technology startups
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Dipto Chakravarty, Copyright (c) 2014

7. Where to Find Your Dev Wings
 Referrals vs. Recruiters
Leverage the power of referrals
Use few regional recruiters for skills outside of your
network that need to be displaced from competitors
 Locations in NVA
User Groups and Networking Events
Iris Lounge (f.k.a eCitie) and places where geeks go
to chill
 Online Forums Invite prospects over to
visit your startup and
“live” an hour with you
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Dipto Chakravarty, Copyright (c) 2014

8. Where to Setup Your 1st Dev Env
 On-premise –
Continuous integration model
Docker-based integrated BuildShipRun
DevOps
 IT dockerizes the dev and test apps
 R&D uses dockerized apps cross-platform to develop
the product without porting efforts
 Off-premise – on Rackspace, Savvis, AWS,
etc.
Online for scalable environment
On-demand cloud bursts
Plan an elastic dev
environment from Day 1 to
allow you to scale on demand
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Dipto Chakravarty, Copyright (c) 2014 Source: en.wikipedia.org/wiki/Docker_(software), S. Hykes, J. Bultmeyer

9. Who to Build For
 To Do
Focus exclusively on
 User’s use and interactions – M2M, B2B
 Not on engineers’ use, e.g., frameworks
Tools
 Pencil – to create sketches and wire frames
 Unassumer – to develop customers (end-users)
 Personapp – to create informal user personas. Much
quicker than Balsamic or MS Word docs.
 Unbounce – to create landing pages swiftly so that
navigating through the user’s experience is understood
 Not To Do
 Locking into a technology stack till you get the glass right.
There’s a big delta
between user persona
and buyer persona
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Dipto Chakravarty, Copyright (c) 2014

10. What to Build With –Popular Technology
Stacks
AngularJS
HTML/CSS
Java, Scala, Node.js
LAMP (with some FWs)
Python (Django, Pylon)
Ruby on Rails (with its FWs)
APIs (REST), Clojure, RabbitMQ
Fraction of Cloud hosting element
Erlang, Go, Memcache / Redis
NoSQL storage – HBase, MongoDB,
Cassandra, Postgres, Raven, MySQL
Front
Middle
Entrepreneurs
tend to maniacally
focus on product-specific
functions
Back
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instead of hard
technology or
scale issues.
Dipto Chakravarty, Copyright (c) 2014

11. What to Build On
 To Do
SaaS applications that you “turn on”
Mobile apps (iOS or Android) that you download
Appliance form factor that you “ISO” image and ship
 Not To Do
Waste time writing Installers
Coding License Key managers
Rely on CD or patch downloads
How we acquire
software has changed
since the
Floppy/CD/DVD days
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Dipto Chakravarty, Copyright (c) 2014

12. Built to Last vs. Built to Flip
 Tipping Point of every startup …if it makes it
1. Durability
2. Stickiness
3. Sizzle
Interlock on the priority, i.e, how
much energy to put on usability
vs. durability
Stickiness = User’s reliance on your application
Durability = SW uptime / resilience / recovery
Sizzle = Spiffiness (and “eye candy”) of the app
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Dipto Chakravarty, Copyright (c) 2014

13. How Much to Build
 Less is More
Seek more feedback while building less software
Begin building from the glass (not the plumbing)
 Keep it Simple
Pareto Principle states that 80% of the effects come from 20% of the
causes
Suggest we combine the basics of Pareto Principle with the MVP
concept
Think MVP through
Pareto lens. Get one
feature right, before
pushing another!
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Dipto Chakravarty, Copyright (c) 2014
MVP
PRODUCT
80% MACRO
PROBLEMS
20% MICRO
PROBLEMS
20% MAIN
CAUSES

14. How Little to Build
MVP Myths
 Anyone not building an
MVP (minimum viable
product) these days?!
 Who decides what’s a
good-enough MVP?
 How many MVPs are
actually usable?
MVP is the smallest
unit you can build that
delivers value
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Dipto Chakravarty, Copyright (c) 2014 Source: The Lean Startup, Eric Ries

15. MVP Anti-Patterns
Substitution vs.
Complementarity
 Cost  drives Substitution
 Technology 
Complementarity
 Competitive advantage GAP
 Term used to interpret revenue as a gauge of the
competitive separation in the market.
 Competitive advantage
period – CAP
 Term used to estimate the time a company can
maintain a position that creates competitive
separation
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Cost Technology
Dipto Chakravarty, Copyright (c) 2014
CAP vs. GAP Advantage
SUBSTITUTION COMPLEMENTARITY
GAP
CAP Area
Sources: Geoffrey Moore & Peter Thiel

16. What Process to Use to Build
 Scrum
 Kanban
 Waterfall
 Which process you pick is less important than
the process you’ve picked be consistent
Key is to empower the
team and let them build
a rhythm for progress
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Dipto Chakravarty, Copyright (c) 2014

17. How to Handle Your 1st
Customer
 Managing vs. delighting your 1st customer
 Plan to exceed expectations with relevancy of your sw
 Keep interactions brief but frequent (and steady)
 User feedback mechanisms
 Interactive (interviews), plus pervasive
(instrumentation)
 Survey Monkey like forms designed with the right Q&A
 Mgmt feedback criticisms
 Deal with it, but focus on the customer
 Groupthink feedback channels
Relevanc
e leads to
Referenc
e, which
in turn
leads to
Revenue
 Portals, anonymous inbox, informal pings are okay
 Avoid formal Betas. Try 1:1 exclusive calls instead
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Dipto Chakravarty, Copyright (c) 2014

18. What to Expect in POCs
 Prototype vs. Proof of Concept
 The POC is often more important than your Product when it
has funding hinging on it.
 Manage expectations of your team before the
customer/investor’s
 Do’s
 Create ReleaseNotes cheat sheet that documents the
gotchas in the code before the event occurs
 Communicate outside the POC prep meetings
 Don’t
 Become defensive even if you know you’re right
 Assume the POC will go smoothly. There will be issues
POC is seldom about the
product. Its about the
“idea” that’ll be a game
 Spring surprises in your scheduled meetings.
changer
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Dipto Chakravarty, Copyright (c) 2014

19. What are CTO’s Key Hurdles
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Dipto Chakravarty, Copyright (c) 2014
 Coping with constant change / contradictions
 Wrestling with build vs. buy/oem decisions
 Balancing between CAP/GAP with GTM
 Deciding what code to write vs. (re)use
 Planning how to build more with less
 Maximizing the value of IP created
Temper your GTM
pressures with build/buy
decisions to create
durable value

20. What are Engineers’ Key
Hurdles
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Dipto Chakravarty, Copyright (c) 2014
 Managing expectations of CXO/skip-level
 Not making the Death March milestones
 Thinking as a unified team
1. Dev + Test  Scrum model
2. R&D + IT  DevOps model
Planning is easy. Doing is hard.
Startups ship “on time” by
cutting scope, not adding
resources

21. What are PM’s Key Hurdles
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Dipto Chakravarty, Copyright (c) 2014
 Deciding what you’re not
going to do
 Manage the requirements
death spiral via
prioritization
 The Two-week rule
 Get your hands dirty
 Get out of the office!
The MVP of a
Hamburger served.
Say NO to individual requests,
and say YES to key market
needs.

22. Summary
HIRING
 Why hiring=culture≠teams
 When to make R&D hires
 What to keep in mind when
hiring
 What to look for in R&D hires
 Where to find your Dev wings
DEV BED
 Staff with fixed + var cost
 Create an elastic dev bed
 Use DevOps model, not IT
 Pivot on Teams, not Dev+Test
PRODUCT
 Who to build For & With
 What technologies
What to build With
What platforms to build on
Where to begin building Sw
How much (little) to build
What dev processes to follow
DELIVERY
 What to expect in POCs
 Top 3 hurdles for CTO/VP
 Top 3 hurdles for engineers
 Top 3 hurdles for Prod Mgrs
22
Dipto Chakravarty, Copyright (c) 2014

23. What’s Next … 
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User is the
IT
Rise of the
Machines
Internet of
Things
Old
problems by
new names
Dipto Chakravarty, Copyright (c) 2014
 Go, live your dream … build the MVP
 Wearable Computing in 2014
 Apple Watch, Fitness Trackers, etc.
abound
 Crowd-shift from mobile to wearable apps
 Blue Ocean vs. Red Ocean strategy
 Hearable Computing – hearing
aids/BT/NFC
 Nearable Computing – miniature beacons
 Sensors and accelerometers on stickers, not
phones
 SDKs available now

24. 24 Thank You!
On Tw: dipto
On G+, Y!: diptoc
LinkedIn: www.linkedin.com/in/diptochakravarty/
Email: dchakravarty@gmp4.hbs.edu