Jason Cohen - CTO & Co-Founder / WP Engine at SaaStr Annual 2018 Metrics are important, but so is making the tough, gut-wrenching decision to part ways with a key employee. Product strategy is important, but a fixation on the competition is counter-productive. A successful exit can set you up financially, but how do you avoid the fate of (statistically) the majority of founders who become sad and unmoored after an exit, rather than ecstatic over their newfound wealth and entering the next chapter of life?

 We can manage products and even people, but managing our own minds can be hardest of all. Ironic, since biologically it ought to be the thing we can control most of all. Bad management of the mind results in poor strategic decisions, focussing on the wrong things, and unnecessary negative emotions and stress over what someone said on the Internet, what a competitor did, what an employee did, or how the company evolves away from its roots. Startups are difficult enough and risky enough as it is, even without this added burden.



1. Facing some Difficult Truths:
From burn-out to $100,000,000 in ARR
SaaStr 2018
Jason Cohen
@asmartbear
blog.asmartbear.com

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. 23

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

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

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

27. Make the
emotionally tough decisions.

28. “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. Holding on too long:
A consistent, predictable
failure of judgement.
30

31. There’s the good reason,
and then there’s the real reason.
31

32. 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

33. 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

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. Stuck in your craw.
35

36. The emotionally tough choice is
usually the right choice.
36

37. 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

38. Make the
emotionally tough decisions.

39. 39

40. “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”

41. you’re the smartest one in the room
41

42. If you’re the smartest one in the room,
You’re in the wrong room.
42

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

44. 44
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

45. 45
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

46. 46
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

47. 47
You hire mostly “C” Players
Software
Development
Marketing
Sales
Customer
Service
Finance

48. 48
You hire the wrong Players
Software
DevelopmentMarketing
Customer
Service

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

50. Be an editor, not a writer.
50

51. 51
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.

52. Make the
emotionally tough decisions.

53. “Success”
53

54. “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.

55. You sold your baby.
55

57. 57

58. $0
$100
$200
$300
$400
$500
58
Smart Bear Valuation (ish)
SOLD TO INSIGHT
SOLD TO FRISCO

59. $0
$100
$200
$300
$400
$500
59
Smart Bear Valuation (ish)
SOLD TO INSIGHT
SOLD TO FRISCO

60. $0
$100
$200
$300
$400
$500
60
Smart Bear Valuation (ish)
SOLD TO INSIGHT
SOLD TO FRISCO

61. 61

62. 62

63. 63

64. 64

65. 65

66. 66

67. 67
Everyone
deserves
fulfillment.
JOY SKILL
LEARNING
TOIL
FLOW

68. 68
Everyone
deserves
fulfillment.
JOY SKILL
NEED
TRAP
BURN-OUT
TRAP

69. 69

70. Facing some Difficult Truths:
From burn-out to $100,000,000 in ARR2
SaaStr 2018
Jason Cohen
@asmartbear
blog.asmartbear.com