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D H A R M E S H S H A H
CO-FOUNDER & CTO
Facing Fears to 

Build a Better
Software Business
Version 01.04.01
Hi, I’m
@dharmesh
This is #bos2019
Marketing, sales and CRM software.
I’m co-founder/CTO
My History With Business of Software
My History With Business of Software
1, 1, 1, 1, 1, 3, 3…
SoftwareBusiness
PUBLIC
SPEAKING
Personal stories
can you make
you seem
almost
human.
Yes, you can say
words out loud!
INTROVERTS
FOR
DREADx
FEARS WORTH SHARING
DREADx
FEARS WORTH SHARING
x = independently made-up non-event.
Professional FearsPersonal Fears
Professional FearsPersonal Fears
(B2B)(B2C)
My Biggest Fears
My Biggest Fears
My Biggest Fears
My Biggest Fears
People Who Did Not Invent
The Venn Diagram
John Venn (1834 - 1923)
People Who Did Not Invent
The Venn Diagram
GarfunkelSimon
Simon
&
Garfunkel
Loves
Carrots
Loyal
Friend
Sven Diagram
Loves
Carrots
Loyal
Friend
Overcoming obstacles
often involves the
intersection of different 

but complementary things.
The Five Fears
1
Fear Of
Commmitment
A hesitation to
commit often stems
from wanting to
hedge your bets.
Fear of Commitment1
When you commit
to nothing, you
compromise on
everything.
Opportunity
T.A.M.
(Total Addressable Market)
T.A.M.
Opportunity
I.A.M.
(Total Addressable Market)
T.A.M.
Opportunity
I.A.M.
(Immediately Accessible Market)
(Total Addressable Market)
Fear of Commitment1
We should stop
debating this
and just decide.
Fear of Commitment1
Small Enough

to Delight
Big Enough
to Grow
Defining Your Market
Fear of Commitment1
When you narrow your focus instead of
broadening your market,
it’s easier to grow.
Fear of Commitment1
Need to e x p a n d your market?
Existing Product
Existing Customer
Existing Product
New Customer
New Product
Existing Customer
New Product
+ New Customer
...
Existing Product
Existing Customer
Existing Product
New Customer
New Product
Existing Customer
New Product
+ New Customer
...
Existing Product
Existing Customer
Existing Product
New Customer
New Product
Existing Customer
New Product
+ New Customer
...
It’s usually easier to build a new product
than it is to build a new customer base.
Pro tip: New products can often
reuse ...
The long-term success of a software company
is correlated to the level of leverage.
Commit to your code.
Don’t compromise.
What We Should FearWhat We Fear
Unwavering
Commitment
Uninspired
Compromises
Fear Of
Differences
2
Fear of Differences2
Dharmesh Shah (Me 1.0)
Fear of Differences2
David Shah (Me 2.0)
Fear of Differences2
@dharmesh (Me 3.0)
Fear of Differences2
I met this guy
named Brian.
He was very clueful.
There was just
one problem
with Brian.
I MBAs.
MBA
Fear of Differences2
My Friends
MBANot MBA
Fear of Differences2
I’m an MBA
student too.
Fear of Differences2
VP Marketing
VP Sales
VP Customer Support
VP Engineering
Founder/CEO
Founder/CTO
MBA
MBA
MBA
MBA
MBA
MBA
Fear of Differenc...
Not all geeks are technology geeks.
There’s such a thing as business geeks.
As important as tech geeks
VP Marketing
VP Sales
VP Customer Support
VP Engineering
Founder/CEO
Founder/CTO
Fear of Differences2
Early HubSpot Team
M...
The best time to
build with diversity:
time t=0
The next best time:
t=(n w)
The best time to
build with diversity:
time t=0
Being
different is
not just OK,
Fear of Differences2
The “Are You an Introvert” Test™
Fear of Differences2
Think of a sentence 

that uses the word “network.”
The Quick
“Are You an Introvert” Test™
Fear of Differences2
EXTROVERT
net·work
verb
“I went to that party so 

I could network.”
EXTROVERT
net·work
verb
“I went to that party so 

I could network.”
INTROVERT
net·work
noun
“I didn’t go to the party bec...
“This person is a
culture fit.”
“This person is a 

clone of me.”
a fine line
Fear of Differences2
How do I know if I’m correctly 

hiring for culture or convenience?
Communicate
Your Culture
CultureCode.com
Clearly articulate 

what you value,
who you value, and
how you operate.
Fear of ...
What We Should FearWhat We Fear What We Should FearWhat We Fear
Dealing with
Differences
Surrendering to
Sameness
Fear Of
Change
3
Deliver shareholder value.
Purpose of a Corporation:
Statement on the Purpose of a Corporation:
Investing in 

our employees
Delivering value 

to our customers
Generating lon...
Companies should focus on
two delightful experiences:
1
An experience 

for customers
An experience 

for employees
2
Fear...
Your people are
customers too.

The product they 

adopt is your culture.
Fear of Change3
The goal is not to make
your product awesome,
but to make your
customer awesome.
Kathy Sierra
There’s an imbalance
between the demand…
…and supply of
exceptional talent.
What’s the flagship feature
people want from your company?
What will help you win?
You need a machine
learning powered
approach to recruiting
on the blockchain.
You need a machine
learning powered
approach to recruiting
on the blockchain.
(just kidding)
Future of Work = (flexibility)
geographic flexibility (where)
schedule flexibility (when)
method flexibility (how)
where, when, and
how they want.
customers
want to connect
Fear of Change3
Fear of Change3
employees
want to work
where, when, and
how they want.
where, when, and
how they want.
customers
want to connect
+
employees
want to work
Fear of Change3
The best way to win the
battle for talent is to go 

big on a distributed team.
Fear of Change3
Remote 

Employees
Most searched term 

on HubSpot jobs site
Biggest office is
the living room
Remote Work at HubSpot
Fear...
Growth of Remote
Employees Over Time
Fear of Change3
remote people 

= 

people
Fear of Change3
Times I’m
truly happy
Times when I’m
wearing pajamas
Fear of Change3
Pajama Principle
Pajama Time
Success
Success is proportional to 

the degree to which you 

let people stay in their
pajam...
What We Should FearWhat We Fear
Change Stagnation
Fear Of
Disappointing
4
Peanut
Butter
Chocolate
Fear of Disappointing4
Peanut
Butter
Chocolate
Fear of Disappointing4
The OG PBC
Fear of Disappointing4
We want
more cups!
Actually, we
want one
ginormous cup.
Actually, we like
M&M’s. Can you
make them like
M&M’s?
Wait, we’ve got
it! Put the tiny
Reese’s inside
a bigger one!
h/t Brenden Mulligan
"Stop! 

This is crazy!”
Steve Jobs
Apple iCEO, 1997
LaptopDesktop
Consumer Pro
Fear of Disappointing4
–Your Customers
We love having the freedom
of choice, but we hate the
complexity of choosing.
Fear of Disappointing4
How do you fight complexity
and get comfortable
disappointing some?
MISSION: Helping millions of organizations grow better
SERVING
CUSTOMERS SERVICE PARTNERS APP PARTNERS EMPLOYEES COMPANY
P...
What We Should FearWhat We Fear
Disappointing
a Few
Not Delighting
the Many
Fear Of
The Truth
5
Fear of Truth5
IN THE AGE OF
ANXIETY
CUSTOMERS 

CRAVE TRUST
Doesn’t Do
Things We 

Don’t Want
Does Things
We Want
Trust
Fear of Truth5
We will deliver the experience,
the whole experience, and
nothing but the experience.
The Oath Of Experience:
Fear of Trut...
Growth
Value
Usability
Performance
Reliability
Infrastructure
Security
GOALSGUARDRAILS
Earning Trust With The Mainsail (& ...
What We Should FearWhat We Fear
Being
Truthful
Being
Untrustworthy
Fear of Inferiority5
0.0
Fear of Inferiority5
Thank You.
,
@dharmesh
You’ve got questions,
I’ve got opinions.
(some of them are even well informed)
?
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business
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Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business

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Dharmesh Shah (Co-Founder/CTO, Hubspot) - Facing Fears To Build A Better Software Business

  1. 1. D H A R M E S H S H A H CO-FOUNDER & CTO Facing Fears to 
 Build a Better Software Business Version 01.04.01
  2. 2. Hi, I’m @dharmesh This is #bos2019
  3. 3. Marketing, sales and CRM software. I’m co-founder/CTO
  4. 4. My History With Business of Software
  5. 5. My History With Business of Software 1, 1, 1, 1, 1, 3, 3…
  6. 6. SoftwareBusiness
  7. 7. PUBLIC SPEAKING Personal stories can you make you seem almost human. Yes, you can say words out loud! INTROVERTS FOR
  8. 8. DREADx FEARS WORTH SHARING
  9. 9. DREADx FEARS WORTH SHARING x = independently made-up non-event.
  10. 10. Professional FearsPersonal Fears
  11. 11. Professional FearsPersonal Fears (B2B)(B2C)
  12. 12. My Biggest Fears
  13. 13. My Biggest Fears
  14. 14. My Biggest Fears
  15. 15. My Biggest Fears
  16. 16. People Who Did Not Invent The Venn Diagram
  17. 17. John Venn (1834 - 1923) People Who Did Not Invent The Venn Diagram
  18. 18. GarfunkelSimon Simon & Garfunkel
  19. 19. Loves Carrots Loyal Friend
  20. 20. Sven Diagram Loves Carrots Loyal Friend
  21. 21. Overcoming obstacles often involves the intersection of different 
 but complementary things.
  22. 22. The Five Fears
  23. 23. 1 Fear Of Commmitment
  24. 24. A hesitation to commit often stems from wanting to hedge your bets. Fear of Commitment1
  25. 25. When you commit to nothing, you compromise on everything.
  26. 26. Opportunity T.A.M. (Total Addressable Market)
  27. 27. T.A.M. Opportunity I.A.M. (Total Addressable Market)
  28. 28. T.A.M. Opportunity I.A.M. (Immediately Accessible Market) (Total Addressable Market)
  29. 29. Fear of Commitment1
  30. 30. We should stop debating this and just decide. Fear of Commitment1
  31. 31. Small Enough
 to Delight Big Enough to Grow Defining Your Market Fear of Commitment1
  32. 32. When you narrow your focus instead of broadening your market, it’s easier to grow. Fear of Commitment1
  33. 33. Need to e x p a n d your market?
  34. 34. Existing Product Existing Customer Existing Product New Customer New Product Existing Customer New Product + New Customer Customer Product
  35. 35. Existing Product Existing Customer Existing Product New Customer New Product Existing Customer New Product + New Customer Customer Product
  36. 36. Existing Product Existing Customer Existing Product New Customer New Product Existing Customer New Product + New Customer Customer Product
  37. 37. It’s usually easier to build a new product than it is to build a new customer base. Pro tip: New products can often reuse parts of old product.
  38. 38. The long-term success of a software company is correlated to the level of leverage. Commit to your code. Don’t compromise.
  39. 39. What We Should FearWhat We Fear Unwavering Commitment Uninspired Compromises
  40. 40. Fear Of Differences 2
  41. 41. Fear of Differences2
  42. 42. Dharmesh Shah (Me 1.0) Fear of Differences2
  43. 43. David Shah (Me 2.0) Fear of Differences2
  44. 44. @dharmesh (Me 3.0) Fear of Differences2
  45. 45. I met this guy named Brian. He was very clueful.
  46. 46. There was just one problem with Brian.
  47. 47. I MBAs. MBA Fear of Differences2
  48. 48. My Friends MBANot MBA Fear of Differences2
  49. 49. I’m an MBA student too. Fear of Differences2
  50. 50. VP Marketing VP Sales VP Customer Support VP Engineering Founder/CEO Founder/CTO MBA MBA MBA MBA MBA MBA Fear of Differences2 Early HubSpot Team
  51. 51. Not all geeks are technology geeks. There’s such a thing as business geeks. As important as tech geeks
  52. 52. VP Marketing VP Sales VP Customer Support VP Engineering Founder/CEO Founder/CTO Fear of Differences2 Early HubSpot Team MBA MBA MBA MBA MBA MBA
  53. 53. The best time to build with diversity: time t=0
  54. 54. The next best time: t=(n w) The best time to build with diversity: time t=0
  55. 55. Being different is not just OK, Fear of Differences2
  56. 56. The “Are You an Introvert” Test™ Fear of Differences2
  57. 57. Think of a sentence 
 that uses the word “network.” The Quick “Are You an Introvert” Test™ Fear of Differences2
  58. 58. EXTROVERT net·work verb “I went to that party so 
 I could network.”
  59. 59. EXTROVERT net·work verb “I went to that party so 
 I could network.” INTROVERT net·work noun “I didn’t go to the party because the network was down.”
  60. 60. “This person is a culture fit.” “This person is a 
 clone of me.” a fine line Fear of Differences2
  61. 61. How do I know if I’m correctly 
 hiring for culture or convenience?
  62. 62. Communicate Your Culture CultureCode.com Clearly articulate 
 what you value, who you value, and how you operate. Fear of Differences2
  63. 63. What We Should FearWhat We Fear What We Should FearWhat We Fear Dealing with Differences Surrendering to Sameness
  64. 64. Fear Of Change 3
  65. 65. Deliver shareholder value. Purpose of a Corporation:
  66. 66. Statement on the Purpose of a Corporation: Investing in 
 our employees Delivering value 
 to our customers Generating long- term value for shareholders We share a fundamental commitment to all 
 of our stakeholders. We commit to: Fear of Change3
  67. 67. Companies should focus on two delightful experiences: 1 An experience 
 for customers An experience 
 for employees 2 Fear of Change3
  68. 68. Your people are customers too.
 The product they 
 adopt is your culture. Fear of Change3
  69. 69. The goal is not to make your product awesome, but to make your customer awesome. Kathy Sierra
  70. 70. There’s an imbalance between the demand… …and supply of exceptional talent.
  71. 71. What’s the flagship feature people want from your company? What will help you win?
  72. 72. You need a machine learning powered approach to recruiting on the blockchain.
  73. 73. You need a machine learning powered approach to recruiting on the blockchain. (just kidding)
  74. 74. Future of Work = (flexibility) geographic flexibility (where) schedule flexibility (when) method flexibility (how)
  75. 75. where, when, and how they want. customers want to connect Fear of Change3
  76. 76. Fear of Change3 employees want to work where, when, and how they want.
  77. 77. where, when, and how they want. customers want to connect + employees want to work Fear of Change3
  78. 78. The best way to win the battle for talent is to go 
 big on a distributed team. Fear of Change3
  79. 79. Remote 
 Employees Most searched term 
 on HubSpot jobs site Biggest office is the living room Remote Work at HubSpot Fear of Change3
  80. 80. Growth of Remote Employees Over Time Fear of Change3
  81. 81. remote people 
 = 
 people Fear of Change3
  82. 82. Times I’m truly happy Times when I’m wearing pajamas Fear of Change3
  83. 83. Pajama Principle Pajama Time Success Success is proportional to 
 the degree to which you 
 let people stay in their pajamas. Fear of Change3
  84. 84. What We Should FearWhat We Fear Change Stagnation
  85. 85. Fear Of Disappointing 4
  86. 86. Peanut Butter Chocolate Fear of Disappointing4
  87. 87. Peanut Butter Chocolate Fear of Disappointing4
  88. 88. The OG PBC Fear of Disappointing4
  89. 89. We want more cups!
  90. 90. Actually, we want one ginormous cup.
  91. 91. Actually, we like M&M’s. Can you make them like M&M’s?
  92. 92. Wait, we’ve got it! Put the tiny Reese’s inside a bigger one!
  93. 93. h/t Brenden Mulligan
  94. 94. "Stop! 
 This is crazy!” Steve Jobs Apple iCEO, 1997
  95. 95. LaptopDesktop Consumer Pro Fear of Disappointing4
  96. 96. –Your Customers We love having the freedom of choice, but we hate the complexity of choosing. Fear of Disappointing4
  97. 97. How do you fight complexity and get comfortable disappointing some?
  98. 98. MISSION: Helping millions of organizations grow better SERVING CUSTOMERS SERVICE PARTNERS APP PARTNERS EMPLOYEES COMPANY PLAYS TARGETS Customer First approach to delight customers and spin HubSpot’s flywheel Fight friction to improve the customer experience Open Platform to move from all-in-one suite to all-on-one platform Inclusive Content to attract, retain, and empower passionate employees of all genders and ethnicities OMISSIONS HubSpot MSPOT
  99. 99. What We Should FearWhat We Fear Disappointing a Few Not Delighting the Many
  100. 100. Fear Of The Truth 5
  101. 101. Fear of Truth5
  102. 102. IN THE AGE OF ANXIETY CUSTOMERS 
 CRAVE TRUST
  103. 103. Doesn’t Do Things We 
 Don’t Want Does Things We Want Trust Fear of Truth5
  104. 104. We will deliver the experience, the whole experience, and nothing but the experience. The Oath Of Experience: Fear of Truth5
  105. 105. Growth Value Usability Performance Reliability Infrastructure Security GOALSGUARDRAILS Earning Trust With The Mainsail (& Code Red)
  106. 106. What We Should FearWhat We Fear Being Truthful Being Untrustworthy
  107. 107. Fear of Inferiority5
  108. 108. 0.0 Fear of Inferiority5
  109. 109. Thank You. , @dharmesh
  110. 110. You’ve got questions, I’ve got opinions. (some of them are even well informed) ?

×