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Mastering Mutual Mentorship
1. Proprietary and Confidential
START UP
SECRETS
An insider’s guide to unfair competitive advantage
Mastering the gift of mutual mentorship
@underscorevc startupsecrets.com
2. Proprietary and Confidential
Mastering
the gift of
mutual
mentorship
Agenda
• 5:15-5:25 - Introductions – Mentors, Mentees
• 5:25-5:45 - Mutual mentorship
• 5:45-6pm – Setting great objectives
• 6-7pm – Breakouts on goal setting
• 7-7:20pm – Group readout of objectives
• 7:20-8pm – Dinner/networking
4. Proprietary and Confidential
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Why do we do this?
● Community-driven approach to entrepreneurship
● Support founders at the earliest stages
● Make Boston the best place to start a company
5. Proprietary and Confidential
12
teams
(over 120
applications)
20+
Mentors
30+
hours
Content &
workshops
2019
● AI / ML
● Mobility / Routing
● Security
● DevOps
● Future of Intelligent Work / Collaboration
8. Proprietary and Confidential
Community
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Team Core Mentor
_U Investment
Associate Liaison
_U Investment
Team Member
Allparel Amory Wakefield Julia Lily
AllSpice Jon McEleney Julia John
Bountium David Fragel Blaze Richard
Breen Technologies Sanjeev Banerji Blaze Lily
BusRight Jesse Bardo Cameron John
Frase AI Anthony Habayeb Cameron Michael
Entheleon Jason Burke Blaze Lily
Marlo Matt Bilotti Julia Lily
Posh Jeff Barnett Julia Michael
Routable.ai Rob Stevens Cameron Richard
TransKey Chris Wolfel Cameron Richard
Wabbi Ellen Nussbaum & Phil Francisco Blaze Richard
10. Proprietary and Confidential
Are you seeking a handout or real help?
Do you want an answer or are you really
looking to learn?
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Do you know what help you want and how
to ask for it?
startupsecrets.com@underscorevc
14. Proprietary and Confidential
Answers are for history lessons
Questions are for future breakthroughs
Breakthroughs present opportunities for
Startups
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“We cannot solve our problems with the
same thinking we used when we created
them."
Albert Einstein
16. Proprietary and Confidential
Question the Answers!
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Are they appropriate for YOU?
Tempt you to take the road already traveled
Don’t develop curiosity…
Combinatorial thinking can be much more powerful than individual
answers
… and what happens when you don’t have someone there to give you
answers?
17. Proprietary and Confidential
Mentees: How about asking for
questions?
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SERIOUSLY!
• Think about it… when you were
asked a really great question, did it
get your mind working?
• Consider asking your mentor for great
questions to help you puzzle the
answer for yourself…
…enabling the “AHA!” moment
18. Proprietary and Confidential
Mentees: What’s stopping you from
answering your own questions?
24startupsecrets.com@underscorevc
What do you need?
• A new skill?
• An experience?
• Some knowledge?
How and where can I best get these?
Is it one-off help or is it an enduring kind of learning you need?
Mentorship is often only a part of the solution
Sometimes mentors are just pointers to other resources
19. Proprietary and Confidential
Mentors & Mentees
25startupsecrets.com@underscorevc
So how do you find the right questions?
Could you ask the market ?
• Ask the customer, user, potential market?
At least understand their view of the problem
• _U First participants: engage our Core Community
Earn their trust
20. Proprietary and Confidential
Tools
26startupsecrets.com@underscorevc
Tools for guiding you to the right questions…
• Field work
• Surveys
• Landing Pages
• Prototypes (paper, web, UX)
• Discovery, exploration
• Research
• Brainstorming
• Etc…
• Frameworks (my personal favorite)
21. Proprietary and Confidential
Exercise
Mentors
How can you help them find a
way to iterate quickly and
effectively?
Mentees
What is one thing you’d like to
test? How could you test it
quickly and easily?
22. Proprietary and Confidential
Startup Secret:
“Don’t take advice blindly, take it mindfully”
Your mind and instincts are your best resources to set a course for something that can work forYOU.
24. Proprietary and Confidential
Enabling the Eureka! moment…
32startupsecrets.com@underscorevc
Mentor to Mentee test:
• If I give you this answer, then what will you do with it?
• What comes next?
(Hint: If it only advances you one step, it's probably not a good question or answer.
Remember the chess game, are you helping them master it?)
25. Proprietary and Confidential
Enabling the Eureka! moment…
33startupsecrets.com@underscorevc
Example:
Question for answer:
• Mentee:
Should I price this at x or y?
• Mentor:
y
Question for question:
• Mentee:
How should I charge for my product?
• Mentor:
Where is the core value?
Who will see that and how will they value it?
How will you prove that value?
26. Proprietary and Confidential
Mentors: What are you trying to develop in
your Mentee?
34startupsecrets.com@underscorevc
Mentors, if you’re not giving Mentees answers, what are you giving them?
• Curiosity
• Joy of learning
• Confidence to try
• Resourcefulness, initiative – eg EXTERNAL validation
A journey from AHA to WOW - I can do this !!
• Enlightenment
29. Proprietary and Confidential
Startup Secret:
“Things are rarely ever as good as they seem,
or as bad as they seem in the moment”
THE MENTOR’S ROLE IS TO PICK THE MENTEE UP WHEN THEY ARE DOWN,
AND KEEP THEM FROM RISING TOO FAR UP!
30. Proprietary and Confidential
How we’ll work together
Weekly check-ins (in person or calls)
• Progress against milestones
• Challenges
• Help needed
”Board meetings” (3x)
• Updates in advance (written)
• Discussion – key strategic questions against milestones
What’s not going well?
Where do you need help?
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31. Proprietary and Confidential
How do you know you’re a good mentor or
mentee?
39startupsecrets.com@underscorevc
Is this working?
• Ask for feedback!
How do you improve?
• Ask for measures for success!
32. Proprietary and Confidential
Record & review regularly
40startupsecrets.com@underscorevc
Mentees - record what you learned!
• Share with your mentor at your next checkpoint
• How you learn is a great guide for your mentor to teach you
Mentors – figure out how to coach your specific mentee
• Everyone learns differently, successes AND failures
Book: "On Managing Yourself”
Review regularly
• Mutual feedback
• If the relationship isn’t working… it won’t fix itself!
33. Proprietary and Confidential
Mentoring is a gift…
41startupsecrets.com@underscorevc
The question is:
• Do you have it?
or
• Do you give it?
Neither: At it’s best, giving and receiving
34. Proprietary and Confidential
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The importance of YOU in the equation…
“Nothing is impossible, the word itself says I’m
possible."
- Audrey Hepburn
36. Proprietary and Confidential
Setting milestones for the summer
Team
(if applicable)
What are key hires that will move the business (if any)? Or advisors?
Problem Are you solving a valuable problem uniquely well? How will you define and qualify your problem?
Product What do you need to build to make your product differentiated, valuable and a “need to have”?
Customers & Go-to-
Market
How will you define and go after your target segment?
Business model How to you create leverage in your business model?
37. Proprietary and Confidential
Deliverable: 3 objectives for the UFirst program
(8 weeks)
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Objective
What business outcome do you
want to achieve
Key Results
How will you know if you’ve
achieved it (measurable)
Initiatives
What activities will get
you there
Who
Who is
responsible for
delivering
(1)
(2)
(3)