How to prepare, boost your confidence, and handle killer questions during your startup pitch. Tips to help any entrepreneur pitch to VCs with wow them with your confidence, passion, and grasp of your venture. The third and final session on pitching perfectly I gave at Samurai Startup Island in Tokyo.

1. 1
Preparation, Confidence, and
Dealing with Tough Questions
Pitching Perfectly Session 3
Darren Menabney
@ Samurai Startup Island
Tokyo
10.29.2015

2. “The first draft of
anything is shit.”
2
- Ernest Hemingway

3. NOTE this
presentation
is not a first draft!
3

4. DARREN
MENABNEY
-2011, Toronto
BSc Astrophysics, U of T
Government of Canada
Revenue, Industry,
Foreign Affairs, Defence
2011+, Tokyo
MBA, GLOBIS University
Global HR, Ricoh Co. Ltd.
Part-time Faculty, GLOBIS University
4

5. © Javier Montano /
TEDxKyotoUniversity
5
Judging pitches
Attending a LOT of
pitch contests
Writing & delivering
pitches
Coaching startups
Teaching entrepreneurs
at MBA program
Public speaking

6. 1. Preparation
& Rehearsal
6

7. “In all things the way you practice
defines the way you perform. It’s selfish
to make an audience endure your first or
even third try. Why be selfish? If you’re
generous to your audience they’ll love
you.” – Scott Berkun
Author, Confessions of a
Public Speaker
7

8. Make any mistakes
BEFORE you pitch
8

9. Uncertainty
and
Surprises
Confidence
and
Success
Preparation and rehearsal WILL
determine your success
9

10. 1. Refining the Pitch Deck
2. Improving your delivery
3. Managing time
10
HOW to prepare?
4. Simulating Q&A

11. 1. Refining the Pitch Deck
11
HOW to prepare?

12. “In writing, you
must kill all your
darlings.”
12
- William Faulkner

13. Attack your own slides
Question your assumptions
Ask “So what?” to each slide and
each element of each slide
…and repeat!
13

14. If it adds no value, remove it
If it looks weak, strengthen it
If even you don’t understand it, fix it!
14

15. 15
This is a
Team
activity

16. 2. Improving your delivery
16
HOW to prepare?

17. Record and watch a
video of you making
the pitch
HOW to prepare?
17

18. Rehearse in front of
• team
• mentors
• pitch coach
HOW to prepare?
18

19. Get a lot of
early feedback
from your team
19
HOW to prepare?

20. Learn from your
mistakes
Build on your strengths
20
HOW to prepare?

21. …then rehearse
your pitch again
HOW to prepare?
21
…and again!
…and again

22. 3. Managing time
22
HOW to prepare?

23. After you can deliver
content smoothly, work
on time management
HOW to prepare?

24. Use slide auto-advance
20-30 seconds per slide
HOW to prepare?
24
Milestone slides

25. The Five Minute Pitch Deck
Title Page with Company’s Purpose (0:15)
Elevator Pitch (0:15)
The Problem (0:30)
Market Sizes (0:20)
Your Value Proposition (0:30)
Why Now? (0:20)
Go To Market Plan (0:30)
Competitive Landscape (0:20)
Business Model (0:30)
Your Team (0:20)
Financials analysis & projections (0:30)
What You Have, What you need (0:30)
Summary (0:10)

26. If your pitch needs to be
done in 10 minutes,
rehearse for 8
HOW to prepare?
26

27. 4. Simulating Q&A
27
HOW to prepare?

28. What can you do to
prepare
for audience
questions?
28

29. Rehearse
&
Know your Audience
29

30. Identify weaknesses in pitch
Anticipate questions
Prepare answers
Practice giving those answers
Rehearsal helps you…
30

31. Past pitch events they judged?
Questions they asked
Their style
Read judges’ blogs & watch any videos of them
Demographics of audience?
Industry crowd vs general audience
Other startups
Know Your Audience…
31

32. Skills Money
Specialist Audience
General Audience
VC
Angel
Talent
Bank
Mixed
FFF
32

33. 2. Boosting
Confidence
33

34. Your confidence...
Audience’s
confidence in you
34

35. How to give your confidence a
20%+ boost in just two minutes
35

36. Copyright © Amy Cuddy, TED36

37. Copyright © Amy Cuddy, TED37

38. Two minutes of this
Stress level DOWN 25%
Confidence level UP 20%
http://www.ted.com/talks/amy_cuddy_your_body_language_shapes_who_you_are?language=en38

39. Drink some
water
BEFORE
you start
39

40. Feel

41. 41
Check out the room
before the pitch event

42. Windows?
Heating?
Lighting?
Projector?
Seating?
Acoustics?
42

43. Bring backups
43
of your backups

44. How to
recover
from a
mistake?
44

45. 45

46. 3. Q&A Time
46

47. 47

48. Questions
indicate interest
48

49. "Thanks for that question."
"Great question!"
"That's a really good
question."
"I was hoping someone would
ask me that."
49

50. Title Page
Elevator Pitch
The Problem (Opportunity)
Market Sizes
Your Value Proposition
Why Now?
50
Go To Market Plan
Competitive Landscape
Business Model
Your Team
Financial Analysis & Projections
What You Have, What You Need
Summary
13 Points You Should Have Covered in Your Pitch Deck

51. So what else
can you be
questioned on?
51

52. Two Basic Question Types
1.Clarifying
52
2. Expanding

53. Clarifying Questions
53
“Why did/didn’t you…?”
“Tell me more about…”
“I don’t understand…”
“How did you calculate X…”

54. Expanding Questions
54
“What if…?”
“Have you thought about…”
“Where will you be in # years?”

55. Some Actual Killer Questions I’ve Heard
“Who are your competitors and how are you
beating them?”
“Is your customer base growing? What
is your retention like?”
“Are you a platform, or are you offering a
service?”

56. Some Actual Killer Questions I’ve Heard
“Show me how you can scale.”
“So when would I get my 100X back?
“I just have one question. What the f**k
do you do?”
“Why did you start this company?”

57. DIFFICULT
QUESTIONS?
57

58. Three Approaches
To Difficult Questions…
1) Delay
2) Defer
3) Don’t know, but…
58

59. 1) Delay
• Paraphrase
• Repeat the question
• Buy thinking time!
59

60. 2) Defer
…to your teammates
…to your tech experts
60

61. “Tricky question, maybe my
CFO Bob can answer that.
Bob, can you help?”
61

62. 3) Don’t know,
but…
62

63. “Sorry I can’t give you an
answer right now. I’ll look into
it when I’m back at the office
and get you an answer.”
63

64. TRY to
answer a question
(say something)
64

65. Questions turn
your pitch into a
conversation
65

66. Continue
practicing!
Continue
growing!
Pitch like
a pro!

67. 67
APPENDIX

68. The following slides show examples of some common
questions you must be prepared to answer
Questions have been summarised according to the
relevant slides you must include in your pitch deck
Green questions indicate killer questions, good luck!
Questions You May Get
68

69. “How have people been dealing with this problem before
you came along?”
“Why is this a problem?”
“Why is this a BIG problem?”
Questions - The Problem
69

70. “How much does that problem cost?”
“How much will customers pay to fix that pain?”
“How did you calculate the Total Addressable Market?”
“What original market research have you done?”
Questions - Market Sizes
70

71. “Take me on a typical customer’s journey.”
“Why should I care?”
“I still don’t get it. What do you do?”
“I just have one question. What the f**k do you do?”
“What’s your proprietary IP?”
“How will you deal with government regulations (e.g. FDA)?”
Questions - Your Value Proposition
71

72. “Why has no one been able to do this before?”
“What changed to make now the right time for your
solution?”
Questions - Why Now?
72

73. “How will you enter the market?”
“How will you grow in the market?”
“How much do you need to expand?”
“Who are your existing customers?”
“How do customers find you?”
“What kind of traction have you got so far?”
Questions - Go To Market Plan
73

74. Questions - Competitive Landscape
74
“Who are your biggest competitors?”
“How can you beat them?”
“Why are you better?”
“Competitor X is a huge, established player in this
market. How can you beat them?”
“How did you research the competitive landscape?”

75. Questions - Business Model
75
“How do customers pay you?”
“How did you calculate your unit cost?”
“How will you distribute your product?”
“Who are your suppliers?”
“Are you a platform, or are you offering a service?”
“What are your bottlenecks and how do you manage them?”

76. Questions - Your Team
76
“Why did you start this company?”
“How much have you personally invested in this venture?”
“Tell me more about your past successes.”
“Tell me about your past failures. What did you learn?”
“Your team is spread over the world, how to you make
decisions and communicate?”
“Why is this team capable of executing your growth plan?”

77. Questions - Financials
77
“When will I get my money back? When will I get my 10X
or 100X back?”
“When will you be cashflow-positive?”
“Explain how you’ll get from point B to point C on your
financial projections?”
“Why aren’t you bootstrapping?”

78. Questions - What You Have/Need
78
“How much have you already received?”
“Who has funded you so far?”
“I still don’t get it. How have you survived so far?”
“Tell me why you need to spend $100,000 on marketing.”