Andrew Gassen, CEO | Pivotal Software 0 for 3: Edtech Startup Lessons Learned I’ve been a part of 3 different education technology companies, all focused on the K-12 market. Each of these companies failed, but each for different reasons and in spectacularly different ways. This talk is a bit of a public post-mortem that focuses on 3 key lessons from each company, including a brief discussion on how we might have done things a different way if I knew then what I know now. Presented by the Serious Play Conference seriousplayconf.com at Orlando, University of Central Florida, UCF, July 24-26, 2019

1. This is not a talk about failure.
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2. This is a talk to equip you for
your journey.
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3. Hi! I’m Andrew Gassen.
I teach at 2 startup accelerators in the
DC metro area.
I pair with Fortune 500 C-Suite
executives and guide them on their
journey to transform into modern
software organizations.
I’ve worked at 4 startups. Three no
longer exist, one is in “zombie mode.”
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4. I teach people, teams, and
companies how to build better
software AND better software
companies.
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5. I can only do this because of the
mistakes I’ve made, the
struggles I’ve experienced, and
the successes in which I’ve been
a part.
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6. Along my journey, I’ve
encountered a number of forces
capable of derailing a group of
people on a mission.
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7. I want to provide you with my
battle-tested playbook for
identifying and eradicating these
Agents of Chaos.
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8. In Today’s Session...
1. ✅ Set the Stage
2. Agents of Chaos
a. What are they?
b. How did they manifest?
c. How’d we tackle them?
d. How’d that work out?
e. How to eliminate
3. Questions
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9. Agent Know It All
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10. Agent Know It All
“You’re really smart, you
can solve all these tough
education problems
despite having no industry
experience or expertise.”
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11. Agent Know It All
Infiltration Strategy
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- Previous successes by key team members
- Anecdotal experience by key team members
- Poor customer research techniques
- Find the Reality Distortion Field

12. Agent Know It All
Impact on the Team
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- Greenshifting
- Skip customer discovery and validation
- Built software “Because I said so”
- Our direction ran counter to the market
- Knowledge silos

13. Agent Know It All
What’d I Do About It?
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- “Think Harder”
- Try to convince the customer that they’re wrong
- Fire people who disagreed

14. Agent Know It All
How’d That Work?
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- Lack of customer adoption (aka no sales)
- Competitors overtook us
- Time and money wasted
- Our reputation was being built in the market

15. How to Tackle Agent Know It All
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16. ANDREWGASSEN.IO
1. Get the team aligned on the desired outcomes
2. Reframe “knowledge” as bite-sized testable hypotheses
3. Agree on the indicators of success and progress
4. Do work, measure progress, as quickly as possible
5. Revisit, reflect, reframe, refocus
Eradicating Agent Know It All

17. Sound familiar?
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18. ANDREWGASSEN.IO

19. Example
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The Know-It-All
We need a playlist creator tool that totally
redefines lesson plans.
Success Indicators
● All our requirements are done by
start of school
Getting it Built
● Wireframes + Mockups
● Debate, change, and internal
sign-off
● Write all the code
● Make sure the code works
● Release it to production

20. Example, Reframed
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Desired Outcome
Provide a more efficient way for teachers
to create lesson plans.
Success Indicators
● >50% of teachers with access use
our tool to build lesson plans
● Time spent building lesson plans in
our tool is less than the observed
baseline
Potential Experiments
● Clickable prototype of our new
playlist creator idea
● Provide starting templates
● Allow teachers to share lesson
plans
● Made it easier to find vetted
content
● Auto-filled a lesson plan based on a
questionnaire

21. Agent Feature Factory
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23. Agent Feature Factory
“It’s not ready yet, but once you
build that next thing, THEN it’ll be
ready.” Repeat forever.
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24. Agent Feature Factory
Infiltration Strategy
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- Lack of traction in the market
- Inexperienced team
- Fear
- Poor development methodology

25. Agent Feature Factory
Impact on the Team
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- Mindset that more stuff = better
- Constantly chasing, never driving
- Lost sight of the actual outcomes we wanted to deliver

26. Agent Feature Factory
What’d I Do About It?
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- Set arbitrary milestones...that moved
- Just continued planning and building

27. Agent Feature Factory
How’d That Work?
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- Products never got in the hands of real users
- Super large set of unvalidated solutions
- Sales expectations became unrealistic as R+D spend
increased

28. How to Tackle
Agent Feature Factory
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29. Don’t Pop the Bunny!
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30. ANDREWGASSEN.IO
1. Practice continuous delivery
a. This is a huge, huge topic.
2. Build an outcomes-based roadmap
a. But, like, actually use it
3. Understand where your value is
4. Adopt Lean Startup principles
Eradicating Agent Feature Factory

31. Table Stakes
Performers
Delighters
Lower Quality Higher Quality
Happy User
Unhappy User

32. App Metrics
Utterance
Support
Codeless
Builder
Lower Quality Higher Quality
Happy User
Unhappy User

33. Agent Old School
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34. Agent Old School
“If it worked 30 years ago, it will
work now.”
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35. Agent Old School
Infiltration Strategy
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- Previous successes by key team members
- Outdated education
- Being “out of the game” for a while
- Lack of real-world experience

36. Agent Old School
Impact on the Team
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- Doing things that contradict modern best practices
- Unjustified confidence
- Juuuuust enough progress to keep going

37. Agent Old School
What’d I Do About It?
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- ...nothing
- Mutiny! New School vs Old School
- Beat the drum of a wholesale transformation effort

38. Agent Old School
How’d That Work?
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- Everybody dug their heels in, as a matter of principle
- Team trust eroded
- Folks left
- Decisions made based on allegiance, not value

39. How to Tackle Agent Old School
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40. ANDREWGASSEN.IO
1. Get a baseline of the current operations
2. Identify the top 1-3 areas to start tweaking
3. Collaborate and align on shared success indicators
4. Get little wins, one by one
Eradicating Agent Old School

41. Agent Value Line
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42. Servers +
Infrastructure
Game Engine
Project
Management
Tooling
Programming
Languages /
Frameworks
Version and
Source
Control
Code quality
improvement
Development
Methodology
Availability
New features
Bug fixes
Performance
gains
Release
frequency
Stability

43. Servers +
Infrastructure
Game Engine
Project
Management
Tooling
Programming
Languages /
Frameworks
Version and
Source
Control
Code quality
improvement
Development
Methodology
Availability
New features
Bug fixes
Performance
gains
Release
frequency
Stability

44. Servers +
Infrastructure
Game Engine
Project
Management
Tooling
Programming
Languages /
Frameworks
Version and
Source
Control
Code quality
improvement
Development
Methodology
Availability
New features
Bug fixes
Performance
gains
Release
frequency
Stability
USERS CARE ABOUT THIS STUFF
USERS DON’T CARE ABOUT THIS STUFF

45. Agent Value Line
“Sure, A, B, and C are the most
important, but it doesn’t matter
unless you also do X, Y, and Z.”
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46. Agent Value Line
Infiltration Strategy
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- Made decisions based on technology, not product
- Buzzword Bingo

47. Agent Value Line
Impact on the Team
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- Everybody was extremely busy, working very, very hard
- Really neat (?) internal technology demonstrations
- Progress seemed really slow

48. Agent Value Line
What’d I Do About It?
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- Honestly, nobody in our entire organization (myself
included) viewed this as a problem. It was just business as
usual.

49. Agent Value Line
How’d That Work?
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- Technical complexity went through the roof
- New hires took a long time to ramp up and wanted to join
the resume-driven development
- So much output, so few outcomes

50. How to Tackle Agent Value Line
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51. ANDREWGASSEN.IO
● Use User Stories
○ As a teacher, I want ________ so that ___________.
● Use Job Stories
○ When ______, teachers want ________ so that
_______.
● Prioritize that backlog ruthlessly
○ “How does this get us to our desired outcome?”
Eradicating Agent Value Line

52. ANDREWGASSEN.IO
1. Align on why we exist and the key outcomes we need to
drive
2. Map out the activities the team, not individuals, engages in
3. Estimate the time each activity takes
4. Prioritize areas where that time can be reduced
5. Empower people to make the changes
Eradicating Agent Value Line

53. Story Time:
Agent Fail Whale
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54. How to Tackle Agent Fail Whale
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55. Eradicating the Fail Whale
Code Freeze isn’t the answer!
Adopt modern processes!
Come talk to me!
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56. The Double Agent
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57. The Double Agent
“Look, this is how we do it over
HERE, so you need to make your
software like this, too.”
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58. The Double Agent
Infiltration Strategy
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- Partnership agreements with an imbalance of power and
trust
- Provide something we need and can’t get elsewhere

59. The Double Agent
Impact on the Team
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- Spent time doing things that ran counter to our perspective
- Loss of morale; devaluation of expertise
- Unintentional “stealth” mode
- Turning down user feedback

60. The Double Agent
What’d I Do About It?
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- Technical shortcuts to get sign off
- Compromises between businesses that impacted end-user
experience
- Anything they asked us to

61. The Double Agent
How’d That Work?
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- Never launched
- Competitors blew by us
- Partnership dissolved
- Tremendous value left undelivered

62. How to Tackle the Double Agent
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63. ANDREWGASSEN.IO
1. Align on outcomes, not features or outputs
2. Be explicit about who owns what in the relationship
3. Be the expert in the areas of your expertise
4. Regularly check-in on progress toward key success
indicators
Eradicating the Double Agent

64. DROP ADD KEEP IMPROVE

65. Agent Hollywood
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66. Agent Hollywood
“Who cares if you don’t have
customers, look at how great those
numbers are!”
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67. Agent Hollywood
Infiltration Strategy
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- Internal competition for resources
- Output-based cultures
- Low trust within the team

68. Agent Hollywood
Impact on the Team
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- Incentivized to stretch the truth to the stretchiest point
- Wasted time and effort on vanity indicators
- People chose sides
- False sense of security

69. Agent Hollywood
What’d I Do About It?
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- Try to “catch” the “other side”
- Be the better one-upper
- Try win as many “awards” as possible

70. Agent Hollywood
How’d That Work?
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- Won awards!
- Leaders (and entire teams!) left the company
- All of our internal metrics were meaningless
- Zero new customers

71. How to Tackle Agent Hollywood
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72. ANDREWGASSEN.IO
Align 👏 on 👏 Outcomes 👏
Eradicating Agent Hollywood

73. ANDREWGASSEN.IO
Measure 👏 What 👏 Matters 👏
Eradicating Agent Hollywood

74. Agent Tug-o-War
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75. Agent Tug-o-War
“They’re wrong, you’re right, just go
do your thing over there.”
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76. Agent Tug-o-War
Infiltration Strategy
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- Lack a common purpose
- Poor prioritization
- Low trust

77. Agent Tug-o-War
Impact on the Team
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- Teammates disappear for pet projects
- “Us vs Them” mentality
- Progress on core product grinded to a halt
- Team spread too thin to do good work

78. Agent Tug-o-War
What’d I Do About It?
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- Pass it off as being a startup
- Accuse people of not being team players
- Accuse people of not being cut out for startup life
- Recruit as many people to “my side” as possible

79. Agent Tug-o-War
How’d That Work?
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- Several incomplete, half-@$$ products
- Cliques left all at once
- Unhappy, or nonexistent, customers

80. How to Tackle Agent Tug-o-War
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81. An
Unhealthy
Team
An
unhappy
prospect
that isn’t a
customer

82. A Healthy
Team
A Happy
Customer

84. Agent Viability
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86. Agent Viability
“Real startups have an office in
Silicon Valley and specialized
lighting and snack walls.”
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87. Agent Viability
Infiltration Strategy
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- Perceived peer pressure
- Hubris
- Ignorance (or lack) of key indicators
- Silly expenses
- Time to market is too long
- No sales

88. Agent Viability
Impact on the Team
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- Visible stress on the executives
- Product ADD / Spaghetti-at-the-wall
- Focus on fundraising, not delivering user value

89. Agent Viability
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90. Agent Viability
What I’ve Seen
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- Say “yes” to anything with dollars associated
- Layoffs
- Constant pivots
- Shut the business down

91. How to Tackle Agent Viability
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92. ANDREWGASSEN.IO
1. What metric matters most for the success of your
company?
2. What’s your cost model?
3. How will you actually make money?
4. What are your unfair advantages?
5. What’s the shortest path to revenue?
Eradicating Agent Viability

94. This was a talk to equip you for
success on your journey.
Questions?
Connect with me...I love to talk!
andrewgassen@gmail.com | www.andrewgassen.io | @andrewgassen | 407-307-6049