This video for this talk from Business of Software Conference USA 2018 will be published here soon: http://businessofsoftware.org/2016/07/all-talks-from-business-of-software-conferences-in-one-place-saas-software-talks/

1. 10 Years of Balsamiq: What I’ve Learned
Giacomo ‘Peldi’ Guilizzoni - Business of Software 2018 - @peldi #BoS2018

2. Ready for Another Group Therapy Session?
Giacomo ‘Peldi’ Guilizzoni - Business of Software 2018 - @peldi #BoS2018

3. Previously, on this show…

6. Oh, Boy.
Giacomo ‘Peldi’ Guilizzoni - Business of Software 2018 - @peldi #BoS2018

7. Peldi’s Law of Learning
f(t) = t/2 + sin (4t) − 0.6

8. 2018
2010
2017
20152012
2011

9. Mr. Pitiful
Giacomo ‘Peldi’ Guilizzoni - Business of Software 2018 - @peldi #BoS2018

11. Let’s Set the Stage

13. 10

18. You’ve Made It. Now What?
Giacomo ‘Peldi’ Guilizzoni - Business of Software 2018 - @peldi #BoS2018

20. We’ve lasted a decade. Now what?

21. Whose company is it?

22. It still all revolves too much around me

23. What am I really needed for?

24. Injected Turbulence!

26. What I did:
1. I delegated product design
2. I delegated engineering management
3. I stopped watching the whole wiki
4. I turned off Pivotal Tracker / Trello / Github notifications
5. I left a bunch of Slack channels

29. Two weeks later…

30. Eyes shut, ears WIDE open

31. 10% slower, 10% lower quality
Hard to detect, kills you in 2 years

32. Twitter and Slack Rehab

36. I have NO IDEA about what people are
doing, or if they’re working at all!

37. We’re not hierarchical,
but we’re not flat either
Wait a minute: who flies the plane?

38. There’s A LOT I need to coach!

40. Ehm…what do I do all day?

41. I fell off the wagon a couple of times

42. One month later…

43. Delegated tasks are going well

44. Not knowing what people
are doing is fine!

45. “I can do this for you”

46. “I can do this for you”
“I’ll help you get it done with coaching,
resources, tools and time”

47. Some people start stepping up

48. Clear schedule? Yeah, right!

49. Most of my meetings are 1-1s

50. I still set all the salaries

51. Communication between
teams starts to break down

52. We need a Product Manager!

53. Nothing major broke

54. Two months later…

55. Something major broke

56. As the weeks went by…

57. Frustration

58. Loneliness

60. Boredom

61. Guilt

62. Curious side-effects…

70. Itchy feet

72. More guilt and self-doubt

73. Infighting

74. Getting stuff done is my
trusty source of endorphins!

75. Sleepless nights

76. Burnout

77. Tenderized!

79. I don’t know what I’m doing

80. I don’t know what I’m doing
I KNOW that I’m BAD at what I’m doing!

81. Too much learning,
not enough teaching

82. Too much doing,
not enough teaching

84. Building a product

85. Building a product
Building a business

86. Being a CEO is not that great.
And it was never my dream!

87. Thank you?
Giacomo ‘Peldi’ Guilizzoni - Business of Software 2018 - @peldi #BoS2018

88. Six months later…

89. The team got the message!

102. Start succession planning???

103. Nothing is forever

104. What’s my new 10-year plan?

105. Hire a PM and someone for HR?

106. Hire or promote a new CEO,
and head Product?

107. What are my options if I
have to leave some day?

108. What will be my new
identity after I leave?

112. Reaching Out

115. Neil Davidson
“Some times in your life you have
to execute, other times you have
to explore” - Clayton Christensen

116. Neil Davidson
“If you burn out and hate your
job, you’re not doing the
company any favors”

117. Neil Davidson
“Maybe you need a COO,
not a new CEO”

119. Michael Pryor
“I’m still doing exactly
what I enjoy doing”

120. Michael Pryor
“I’m scared that if I stopped, I’d feel
unimportant and honestly I’d have
nothing else to do. After a while,
fishing would get pretty boring. ;)”

123. Derek Sivers
“In hindsight, I would have set
up more hierarchy. When I quit,
there were 85 employees mostly
dumping their problems on me”

124. Derek Sivers
“When you feel very frustrated,
don’t mistakenly think there
are only two options”

125. Derek Sivers
“Here lies Derek Sivers who made
CD Baby, and not much else”

129. “You only feel as wealthy
as your cash flow”
Jason Eckenroth

131. Joel Spolsky
“Do you remember why
you liked bootstrapping?”

132. Joel Spolsky
“You have to have a real plan
for what to do when you quit”

133. Joel Spolsky
“You’ve had a large impact already and
you think the only way to top that is to go
bigger. But it’s also about your personal
journey. It’s gotta stay interesting, it’s
gotta keep evolving, it has to keep you
feeling like you’ve lived every year of the
few years we were given”

134. 1. Make a list of all the people you know
2. Email them:
“I’m going to be at ____ doing ____. Please come, and bring a friend!”
3. The list gets longer!
4. Trim the list, and repeat!
Joel Spolsky’s Algorithm for Making
Friends in Your 40s:

136. David Heinemeier Hansson
“Company design is malleable, if you dare it to
be. You can reconfigure the company, its vision,
its scope, and its size. We've configured ours to
be a pretty close approximation of "this is what
I'd want if I had my way in all the matters".
That's the luxury of ownership control and of
rejecting the angel-venture capital funding path”

138. Natalie and Chris Nagele
“Your employees don’t want
you to be unhappy”

139. Natalie and Chris Nagele
“Hobbies sometimes
make things worse!”

140. Natalie and Chris Nagele
“Other people get
to switch jobs!”

143. Jason Cohen
“The founder does NOT have to
run the company forever!”

144. Jason Cohen
“Hiring a great COO is
hard if they don’t have a
chance to become CEO”

145. Jason Cohen
Running AWAY from something
vs
Running TOWARDS something

146. Jason Cohen
“Burnout is doing something
the company needs, and
that you might be good at,
but you don’t enjoy”
https://businessofsoftware.org/2018/02/healthy-wealthy-wise-jason-cohen-wpengine-bos-usa-2017/

147. Wrapping Up

148. What Motivates Founders to Keep Going
• I haven’t “made it” yet
• I gotta finish this thing
• I have boundless ambition
• I carved out my perfect role
• I don’t have anything better to do

149. My Next 3 Steps

150. 1. Make my job fun again

151. 2. Take care of my mental health
with exercise and hobbies
and make new friends!

152. 3. Make Balsamiq Stronger
• Work on it with my awesome team
• Read a bunch of books
• Do a lot of introspection
• Talk to a bunch more people
New 5-year project, yay!

153. It’s NOT Lonely at the Top!
Giacomo ‘Peldi’ Guilizzoni - Business of Software 2018 - @peldi #BoS2018

154. Thank you.
Giacomo ‘Peldi’ Guilizzoni - Business of Software 2018 - @peldi #BoS2018