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Healthy, Wealthy, and Wise
Creating a healthier business through a healthier mind.
Jason Cohen // @asmartbear // blog.asma...
“I don’t want
to be a founder anymore."
“There’s a lot to lose
from speaking how I feel."
“We’re profitable, growing, debt-free”
“I’m supremely unhappy.”
“Possibly [?!?!] skewed point of view”
“I have two options:”
“I have two options:
1. Quit, killing the company.”
“I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.”
“I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.
3. Fix it.”
“I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.
3. Fix it. (can’t be done)”
“I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.
3. Fix it. (can’t be done)
product is compl...
“I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.
3. Fix it. (can’t be done)
product is
compl...
“Is this common?”
“Is this common?
Is there a trick?”
“Is this common?
Is there a trick?”
—A founder in pain
“Is this common?
Is there a trick?”
—A founder in pain
19
20
21
22
25
26
“Is this common?
Is there a trick?”
—A founder in pain
“Is this common?
Is there a trick?”
(How did I get here?)
—A founder in pain
“Is this common?
Is there a trick?”
(What could I have
done differently?)
—A founder in pain
Make the
emotionally tough decisions.
You have to decide to face some
ugly, emotional truths.
“I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.
3. Fix it. (can’t be done)
product is
compl...
“I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.
3. Fix it. (can’t be done)
product is
compl...
“I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.
3. Fix it. (can’t be done)
product is
compl...
Holding on too long:
A consistent, predictable
failure of judgement.
37
There’s the good reason,
and then there’s the real reason.
38
Want to Do
Does not Need
to be Done
Needs
to be Done
Adding an easy,
requested feature
Framework: Am I avoiding what needs...
Want to Do
Does not Need
to be Done
Needs
to be Done
Adding an easy,
requested feature
Framework: Am I avoiding what needs...
Want to Do
Does not Need
to be Done
Needs
to be Done
Adding an easy,
requested feature
Framework: Am I avoiding what needs...
Stuck in your craw.
42
The emotionally tough choice is
usually the right choice.
43
How to do
the tough thing
• Be Swift.
▪ Delay never helps
▪ Delay often hurts
• Be Decisive.
▪ Flapping hurts
• Be Kind.
▪...
Make the
emotionally tough decisions.
“Is this common?
Is there a trick?”
(What could I have
done differently?)
—A founder in pain
47
“I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.
3. Fix it. (can’t be done)
product is
compl...
you’re the smartest one in the room
49
If you’re the smartest one in the room,
You’re in the wrong room.
50
A players hire
A players.
B players hire
C players.
—Steve Jobs
52
Why you end up hiring C players
I’m an
“A” Player?
Hire & Manage
“A” Player
Y
Take 1-3 months
to learn the ropes
N
53
Why you end up hiring C players
I’m an
“A” Player?
Hire & Manage
“A” Player
Y
Become an
“A” Player
in 1-3 months
N
54
Why you end up hiring C players
I’m an
“A” Player?
Hire & Manage
“A” Player
Y
Become an
“C” Player
in 1-3 months
N
Hire...
55
You hire mostly “C” Players
Software
Development
Marketing
Sales
Customer
Service
Finance
56
You hire the wrong Players
Software
DevelopmentMarketing
Customer
Service
“We don’t hire smart people and tell them what to do.
We hire smart people so they can tell us what to do.”
Be an editor, not a writer.
58
59
How to hire and manage outside your expertise
I’m an
“A” Player?
Y
Hire for
enlightenment &
results-orientation
N
1. Ho...
Make the
emotionally tough decisions.
“I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.
3. Fix it. (can’t be done)
product is
compl...
62
“Success”
63
“I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.
3. Fix it. (can’t be done)
product is
compl...
You sold your baby.
65
68
69
70
$0
$100
$200
$300
$400
$500
71
Smart Bear Valuation (ish)
SOLD TO INSIGHT
SOLD TO FRISCO
$0
$100
$200
$300
$400
$500
72
Smart Bear Valuation (ish)
SOLD TO INSIGHT
SOLD TO FRISCO
$0
$100
$200
$300
$400
$500
73
Smart Bear Valuation (ish)
SOLD TO INSIGHT
SOLD TO FRISCO
74
75
76
77
78
79
80
81
82
Everyone
deserves
fulfillment.
JOY SKILL
LEARNING
TOIL
FLOW
83
Everyone
deserves
fulfillment.
JOY SKILL
NEED
TRAP
BURN-OUT
TRAP
84
Healthy, Wealthy, and Wise
Creating a healthier business through a healthier mind.
Jason Cohen // @asmartbear // blog.asma...
Jason Cohen WP Engine Business of Software Conference USA Healthy Wealthy Wise
Jason Cohen WP Engine Business of Software Conference USA Healthy Wealthy Wise
Jason Cohen WP Engine Business of Software Conference USA Healthy Wealthy Wise
Jason Cohen WP Engine Business of Software Conference USA Healthy Wealthy Wise
Jason Cohen WP Engine Business of Software Conference USA Healthy Wealthy Wise
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Jason Cohen WP Engine Business of Software Conference USA Healthy Wealthy Wise

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Slides from Jason Cohen, CTO and Founder, WPEngine's talk at Business of Software Conference 2017.

For updates on future events and to be notified when the talks are published online: http://businessofsoftware.org/updates/

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Jason Cohen WP Engine Business of Software Conference USA Healthy Wealthy Wise

  1. 1. Healthy, Wealthy, and Wise Creating a healthier business through a healthier mind. Jason Cohen // @asmartbear // blog.asmartbear.com Business of Software, Sept 2017, Boston
  2. 2. “I don’t want to be a founder anymore."
  3. 3. “There’s a lot to lose from speaking how I feel."
  4. 4. “We’re profitable, growing, debt-free”
  5. 5. “I’m supremely unhappy.”
  6. 6. “Possibly [?!?!] skewed point of view”
  7. 7. “I have two options:”
  8. 8. “I have two options: 1. Quit, killing the company.”
  9. 9. “I have two options: 1. Quit, killing the company. 2. Hate the next 2-5 years.”
  10. 10. “I have two options: 1. Quit, killing the company. 2. Hate the next 2-5 years. 3. Fix it.”
  11. 11. “I have two options: 1. Quit, killing the company. 2. Hate the next 2-5 years. 3. Fix it. (can’t be done)”
  12. 12. “I have two options: 1. Quit, killing the company. 2. Hate the next 2-5 years. 3. Fix it. (can’t be done) product is complex”
  13. 13. “I have two options: 1. Quit, killing the company. 2. Hate the next 2-5 years. 3. Fix it. (can’t be done) product is complex product is boring”
  14. 14. “Is this common?”
  15. 15. “Is this common? Is there a trick?”
  16. 16. “Is this common? Is there a trick?” —A founder in pain
  17. 17. “Is this common? Is there a trick?” —A founder in pain
  18. 18. 19
  19. 19. 20
  20. 20. 21
  21. 21. 22
  22. 22. 25
  23. 23. 26
  24. 24. “Is this common? Is there a trick?” —A founder in pain
  25. 25. “Is this common? Is there a trick?” (How did I get here?) —A founder in pain
  26. 26. “Is this common? Is there a trick?” (What could I have done differently?) —A founder in pain
  27. 27. Make the emotionally tough decisions.
  28. 28. You have to decide to face some ugly, emotional truths.
  29. 29. “I have two options: 1. Quit, killing the company. 2. Hate the next 2-5 years. 3. Fix it. (can’t be done) product is complex product is boring”
  30. 30. “I have two options: 1. Quit, killing the company. 2. Hate the next 2-5 years. 3. Fix it. (can’t be done) product is complex product is boring”
  31. 31. “I have two options: 1. Quit, killing the company. 2. Hate the next 2-5 years. 3. Fix it. (can’t be done) product is complex product is boring”
  32. 32. Holding on too long: A consistent, predictable failure of judgement. 37
  33. 33. There’s the good reason, and then there’s the real reason. 38
  34. 34. Want to Do Does not Need to be Done Needs to be Done Adding an easy, requested feature Framework: Am I avoiding what needs to be done? Don’t Want to Do Fixing a bug for your largest customer Dealing with difficult employee situation Attending a local event
  35. 35. Want to Do Does not Need to be Done Needs to be Done Adding an easy, requested feature Framework: Am I avoiding what needs to be done? Don’t Want to Do Fixing a bug for your largest customer Dealing with difficult employee situation Attending a local event
  36. 36. Want to Do Does not Need to be Done Needs to be Done Adding an easy, requested feature Framework: Am I avoiding what needs to be done? Don’t Want to Do Fixing a bug for your largest customer Dealing with difficult employee situation Attending a local event
  37. 37. Stuck in your craw. 42
  38. 38. The emotionally tough choice is usually the right choice. 43
  39. 39. How to do the tough thing • Be Swift. ▪ Delay never helps ▪ Delay often hurts • Be Decisive. ▪ Flapping hurts • Be Kind. ▪ To the person ▪ To others ▪ To yourself
  40. 40. Make the emotionally tough decisions.
  41. 41. “Is this common? Is there a trick?” (What could I have done differently?) —A founder in pain
  42. 42. 47
  43. 43. “I have two options: 1. Quit, killing the company. 2. Hate the next 2-5 years. 3. Fix it. (can’t be done) product is complex product is boring”
  44. 44. you’re the smartest one in the room 49
  45. 45. If you’re the smartest one in the room, You’re in the wrong room. 50
  46. 46. A players hire A players. B players hire C players. —Steve Jobs
  47. 47. 52 Why you end up hiring C players I’m an “A” Player? Hire & Manage “A” Player Y Take 1-3 months to learn the ropes N
  48. 48. 53 Why you end up hiring C players I’m an “A” Player? Hire & Manage “A” Player Y Become an “A” Player in 1-3 months N
  49. 49. 54 Why you end up hiring C players I’m an “A” Player? Hire & Manage “A” Player Y Become an “C” Player in 1-3 months N Hire & Manage “C” Player
  50. 50. 55 You hire mostly “C” Players Software Development Marketing Sales Customer Service Finance
  51. 51. 56 You hire the wrong Players Software DevelopmentMarketing Customer Service
  52. 52. “We don’t hire smart people and tell them what to do. We hire smart people so they can tell us what to do.”
  53. 53. Be an editor, not a writer. 58
  54. 54. 59 How to hire and manage outside your expertise I’m an “A” Player? Y Hire for enlightenment & results-orientation N 1. Hold accountable to results. 2. Edit like SJ.
  55. 55. Make the emotionally tough decisions.
  56. 56. “I have two options: 1. Quit, killing the company. 2. Hate the next 2-5 years. 3. Fix it. (can’t be done) product is complex product is boring”
  57. 57. 62
  58. 58. “Success” 63
  59. 59. “I have two options: 1. Quit, killing the company. 2. Hate the next 2-5 years. 3. Fix it. (can’t be done) product is complex product is boring”4. Keep running the company.
  60. 60. You sold your baby. 65
  61. 61. 68
  62. 62. 69
  63. 63. 70
  64. 64. $0 $100 $200 $300 $400 $500 71 Smart Bear Valuation (ish) SOLD TO INSIGHT SOLD TO FRISCO
  65. 65. $0 $100 $200 $300 $400 $500 72 Smart Bear Valuation (ish) SOLD TO INSIGHT SOLD TO FRISCO
  66. 66. $0 $100 $200 $300 $400 $500 73 Smart Bear Valuation (ish) SOLD TO INSIGHT SOLD TO FRISCO
  67. 67. 74
  68. 68. 75
  69. 69. 76
  70. 70. 77
  71. 71. 78
  72. 72. 79
  73. 73. 80
  74. 74. 81
  75. 75. 82 Everyone deserves fulfillment. JOY SKILL LEARNING TOIL FLOW
  76. 76. 83 Everyone deserves fulfillment. JOY SKILL NEED TRAP BURN-OUT TRAP
  77. 77. 84
  78. 78. Healthy, Wealthy, and Wise Creating a healthier business through a healthier mind. Jason Cohen // @asmartbear // blog.asmartbear.com Business of Software, Sept 2017, Boston

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