The document discusses a founder who is feeling unhappy running their profitable and growing company. The founder sees their options as quitting and killing the company, hating the next 2-5 years, or fixing the problems which they feel can't be done since the product is complex and boring. The document goes on to advise founders to make emotionally tough decisions swiftly and decisively, and to be kind. It suggests facing truths about needing to change roles, hire the right people, and potentially sell the company for fulfillment.

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

3. “I don’t want
to be a founder anymore."

4. “There’s a lot to lose
from speaking how I feel."

5. “We’re profitable, growing, debt-free”

6. “I’m supremely unhappy.”

7. “Possibly [?!?!] skewed point of view”

8. “I have two options:”

9. “I have two options:
1. Quit, killing the company.”

10. “I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.”

11. “I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.
3. Fix it.”

12. “I have two options:
1. Quit, killing the company.
2. Hate the next 2-5 years.
3. Fix it. (can’t be done)”

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”

14. “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”

15. “Is this common?”

16. “Is this common?
Is there a trick?”

17. “Is this common?
Is there a trick?”
—A founder in pain

18. “Is this common?
Is there a trick?”
—A founder in pain

19. 19

20. 20

21. 21

22. 22

23. 25

24. 26

25. “Is this common?
Is there a trick?”
—A founder in pain

26. “Is this common?
Is there a trick?”
(How did I get here?)
—A founder in pain

27. “Is this common?
Is there a trick?”
(What could I have
done differently?)
—A founder in pain

28. Make the
emotionally tough decisions.

29. You have to decide to face some
ugly, emotional truths.

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. “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. “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”

35. Holding on too long:
A consistent, predictable
failure of judgement.
37

36. There’s the good reason,
and then there’s the real reason.
38

37. 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

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 to be done?
Don’t Want to Do
Fixing a bug for your
largest customer
Dealing with difficult
employee situation
Attending a local event

39. 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

40. Stuck in your craw.
42

41. The emotionally tough choice is
usually the right choice.
43

42. 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

43. Make the
emotionally tough decisions.

44. “Is this common?
Is there a trick?”
(What could I have
done differently?)
—A founder in pain

45. 47

46. “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”

47. you’re the smartest one in the room
49

48. If you’re the smartest one in the room,
You’re in the wrong room.
50

49. A players hire
A players.
B players hire
C players.
—Steve Jobs

50. 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

51. 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

52. 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

53. 55
You hire mostly “C” Players
Software
Development
Marketing
Sales
Customer
Service
Finance

54. 56
You hire the wrong Players
Software
DevelopmentMarketing
Customer
Service

55. “We don’t hire smart people and tell them what to do.
We hire smart people so they can tell us what to do.”

56. Be an editor, not a writer.
58

57. 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.

58. Make the
emotionally tough decisions.

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”

60. 62

61. “Success”
63

62. “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.

63. You sold your baby.
65

66. 68

67. 69

68. 70

69. $0
$100
$200
$300
$400
$500
71
Smart Bear Valuation (ish)
SOLD TO INSIGHT
SOLD TO FRISCO

70. $0
$100
$200
$300
$400
$500
72
Smart Bear Valuation (ish)
SOLD TO INSIGHT
SOLD TO FRISCO

71. $0
$100
$200
$300
$400
$500
73
Smart Bear Valuation (ish)
SOLD TO INSIGHT
SOLD TO FRISCO

72. 74

73. 75

74. 76

75. 77

76. 78

77. 79

78. 80

79. 81

80. 82
Everyone
deserves
fulfillment.
JOY SKILL
LEARNING
TOIL
FLOW

81. 83
Everyone
deserves
fulfillment.
JOY SKILL
NEED
TRAP
BURN-OUT
TRAP

82. 84

83. Healthy, Wealthy, and Wise
Creating a healthier business through a healthier mind.
Jason Cohen // @asmartbear // blog.asmartbear.com
Business of Software, Sept 2017, Boston