This document summarizes a mentorship workshop focused on mutual mentorship between startup founders and experienced mentors. The workshop covered topics like asking for questions instead of answers from mentors to drive learning, testing ideas quickly through prototypes and customer feedback, and setting objectives for mentor-mentee partnerships over the next 8 weeks. Mentors were encouraged to develop curiosity and confidence in mentees rather than just providing answers. The goal of the program is to help founders and support the Boston startup ecosystem.

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START UP
SECRETS
An insider’s guide to unfair competitive advantage
Mastering the gift of mutual mentorship
@underscorevc startupsecrets.com

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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

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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

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12
teams
(over 120
applications)
20+
Mentors
30+
hours
Content &
workshops
2019
● AI / ML
● Mobility / Routing
● Security
● DevOps
● Future of Intelligent Work / Collaboration

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Introductions
• Name
• Company – tweet description
• One thing you want to learn

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Community to learn
 Peers
 Mentors
 Core Community
 Underscore team
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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

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Mentoring is a gift…
startupsecrets.com@underscorevc

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 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

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Think of it as a game of Chess…
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The MIT Sloan Review

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You can easily ask for the next move…
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But wouldn’t you rather learn how to master
the game?
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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

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Skills

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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?

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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

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Mentees: What’s stopping you from
answering your own questions?
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 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

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Mentors & Mentees
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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

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Tools
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 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)

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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?

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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.

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Mentors: Develop your Mentees!
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 AHA!
 Eureka!
 &*!^#%!

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Enabling the Eureka! moment…
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 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?)

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Enabling the Eureka! moment…
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 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?

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Mentors: What are you trying to develop in
your Mentee?
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 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

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Mentors
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 Be open, honest and accurate wherever possible
 Don’t be afraid to say you don’t know!
 Always look for teaching moments
 Bring humor, have fun!
“To encourage and beyond!”
with apologies to Buzz Lightyear

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Remember
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 For Startups in particular:
“There is no failure, only learning”
#nomorefear #onlylearning
 So make it safe and leave room to fail / learn

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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!

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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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How do you know you’re a good mentor or
mentee?
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 Is this working?
• Ask for feedback!
 How do you improve?
• Ask for measures for success!

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Record & review regularly
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 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!

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Mentoring is a gift…
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 The question is:
• Do you have it?
or
• Do you give it?
Neither: At it’s best, giving and receiving

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The importance of YOU in the equation…
“Nothing is impossible, the word itself says I’m
possible."
- Audrey Hepburn

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Milestones

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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?

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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)

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Readout

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WELCOME

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Thank you!
@underscorevc #startupsecrets