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Leadership: Finding the Next Mountain to Climb

December 21, 2016 / 22:58

This episode features Kathryn Klein interviewing Derek Handley, an entrepreneur, philanthropist, and venture capitalist. They discuss purpose-driven investing, leadership, and the launch of Handley's new venture capital fund, Arrow VC.

Handley shares his journey to finding purpose in business, emphasizing the importance of reflection during challenging times. He explains how his experiences have shaped his understanding of what it means to create impactful companies.

The conversation also touches on the concept of hybrid capital, where for-profit and philanthropic sources come together to support social and environmental initiatives. Handley describes the "Error Terms," a framework for assessing the social mission of potential investments.

Additionally, Handley reflects on leadership qualities, including the need for vision and coachability. He discusses his work with the B Team, an initiative aimed at promoting sustainable business practices among corporate leaders.

This episode provides valuable insights into the intersection of entrepreneurship, social impact, and effective leadership.

TL;DR

Derek Handley discusses purpose-driven investing and leadership in his new venture capital fund, Arrow VC, emphasizing social impact and reflection.

Episode

22:58
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hi i'm kathryn klein i'm happy to be
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here and to be interviewing Derek
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Handley Derek is an entrepreneur social
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entrepreneur philanthropist venture
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capitalist and author and we have a
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tremendous amount to talk about so
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welcome thanks for having me great to
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have you here so you were just a quick
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summary of some of the highlights you a
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co-founded hyper factory you were the
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founding CEO of the B team you are today
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and this week the Nazarian Wharton
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social innovator in residence so here at
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Wharton thank you and you are the
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founder of the newly launched vc fund
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arrow VC great so we have a lot that I'd
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love to talk to you about and the three
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subjects that are highly they're all
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been we could spend a lot of time I
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think our purpose impact invents
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investing venture capital and leadership
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okay so we'll see where we but we can
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get through this cycle so when it comes
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to purpose I mean you I have have
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thought a lot about purpose and you
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found your purpose and that's been
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meaningful for you how did you find your
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purpose as a business person interesting
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question i think the common pattern for
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me has been whenever something really
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terrible has happened from a business or
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a life perspective asking bigger
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questions around what i might be best
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put here to do and so in kind of moments
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of crisis a sense of perspective has
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often opened up new ideas about where i
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could be spending my time and how i
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could be using it so that's one kind of
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common element from the past you know
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ten fifteen years the other is just
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experimenting and exploring different
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places understanding that you know that
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is a journey and you kind of wave in and
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out of things that you resonate with and
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lastly the things that i resonate with
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really trusting that mmm that intuition
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and that instinct to follow that
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whatever that particular calling or idea
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is and giving it the space and time to
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really grow great with in my life so
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that's kind of some of the ways in which
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it's manifested itself and and as i
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understand this there was
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when you were launching hyper factory
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this purpose in this larger vision for
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your contribution to the world was less
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front and center yeah and that shifted
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right i mean i was mostly focused then
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on how do you build a start-up you know
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from where i was in the bottom of the
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world in new zealand and just straight
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out of university and i had this idea
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that i wanted to build a company that
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went global and as a really young person
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to show that it could be done so in a
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sense the purpose that I was trying to
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prove was can we build companies as
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young kids from New Zealand and make it
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in the best night yeah I foot it with
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the best so I was around innovation the
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thrill the chase how do you build a
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company and but when I came in kind of
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stepped back and looked at well what is
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the purpose and what's the what's the
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impact that the company is trying to
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have that's when I looked at much I
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guess a much broader perspective of what
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is possible if you're building a company
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what might you try to have it tackle as
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an issue and and has finding that larger
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purpose been inspiring daunting tiring
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you know energizing how would you
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describe what finally see you like
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you're really connecting with something
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that you feel you're here to do yeah
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it's it's really energizing and
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inspiring and to me one of the tests I
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have around this stuff is if it's
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frightening in some way then it's
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probably the right place yeah it's a
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little bit like it's going to be
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difficult and it's your putting you in
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an uncomfortable position then I feel
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like it's probably where I should be
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going if it looks too comfortable and
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something that you think you could do
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then to me it's as personal you know
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instance it's probably not the right
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thing for me yeah and is your purpose
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succinct enough distinct enough that you
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can articulate it to us not I don't
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think in a sense that I've you know kind
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of created a slogan out of it but at the
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macro level everything that I'm doing
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now is somehow trying to contribute in
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some way to a social or environmental
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issue that I that is that is out there
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in the world or some sort of sort of
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injustice that I think this generation
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should be trying to transform whether
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that's the way we treat global drug
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policy or the way we think about
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what should entrepreneurs be building in
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terms of the companies that people are
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starting so that's kind of the macro I
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guess thesis on an individual basis it's
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about helping and trying to empower and
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build confidence in every single person
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to pursue that the truth that's inside
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of them as to what they should really be
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doing with their life I've met too many
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people who take comp make make a lot of
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compromises and don't pursue the things
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they knew or no are actually where their
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dreams lie for an enormous number of
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reasons that they have created that make
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it very difficult for them whether it's
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about the courage or the confidence or
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practical reasons like you know I
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couldn't possibly do that or it's not
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really my thing to make these changes
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and part of the mission we're on as
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helping all sorts of people realize the
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things that they really want to do in
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the world and that you know investing in
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entrepreneurs we're trying to create
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significant change is one expression of
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that so before we get dig into investing
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in entrepreneurs and who want to make a
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difference in the world any any advice
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to people who may be listening and
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watching and thinking yeah I want to
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find my purpose what the heck is my
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purpose or I don't have time to find my
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purpose well the the biggest advice I
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have in this whole space is taking a
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significant amount of time to reflect
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and think about these kinds of questions
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in the course of your ordinary week or
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months I think we're in a world where
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people operate in a whirlwind battling
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with an inbox for their whole day it
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seems like it's starting n to the blur
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and then you go home and you kind of
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just want to you know get some relief
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but for me the thing that's always
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worked its carving out several hours a
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week to think about the longer term the
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bigger picture and always questioning is
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this where I feel like I'm making the
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biggest difference is this where I feel
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like are my strengths of being brought
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to bear and if the answers are not
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positive for you know enough enough days
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in a row then you have to make changes
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and so creating that space is what I
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think a lot of people strong
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with because they think they've got way
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too much to do right but actually if
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you're doing all the stuff and three or
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five or seven years later and you look
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back it and it doesn't mean anything to
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you that actually it's far worse than
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taking time out now to recalibrate and
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constantly kind of challenge yourself as
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to whether you're being courageous
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enough to really do the things that you
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know in your heart are the things you
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should be doing yeah so you've channeled
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your business expertise and your love of
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entrepreneurship and your sense of
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purpose into a new venture capital fund
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launching today arrow VC so what is
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arrow vc so era is is a new initiative
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that we've been building over the last
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15 months it is spun out of a charitable
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foundation of mine in New Zealand called
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the era foundation error being you know
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the word describes our era the things
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that we should be challenged and
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tackling in ocean spelled that it's a ra
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is the Latin root and I looked at the
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early stage venture space around the
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world and saw that there was definitely
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a need for more early-stage capital and
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support for companies and founders who
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are trying to address a particular
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social or environmental issue that they
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felt really strongly about and they had
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chosen to build a venture-backed company
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to do that so we're looking at companies
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from all around the world and in the
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last year of backed them from you know
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New Zealand Australia Hong Kong New York
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and trying to create a community of
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those those founders but also a
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community of families from around the
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world than one who invest in those
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companies so it's the twofold community
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building that we're kind of embarking on
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right right so you've talked a little
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bit about VC and the need for VC in this
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space can you describe more about the
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companies that pass you know pass
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through your screen that that get all
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the way to this could be an interesting
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and important investment well the first
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thing is this core mission has to be
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something to address a social or
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environmental challenge of the founder
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has stumbled across or has been living
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in for a long time that's the first you
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know kind of test we have developed for
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error a concept called the error terms
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which is like a social term sheet which
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has basically three elements one the
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commitment from the found at
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build into their DNA as an organization
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their purpose is being around this
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particular social issue the second being
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that they are willing to try as hard as
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they can to create at least one metric
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to measure what the progress is they're
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making against the issue and the third
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is that they are building in some way to
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should they succeed and exit and develop
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a successful company that there are some
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ring-fenced equity that they will pay
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forward to a non-profit or an impact
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investing unit or something like that so
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that's kind of how we first look at the
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social mission then we look at things in
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the same way that you look in an early
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stage company so what's the product
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what's unique about it what's the market
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what's disruptive about what they're
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trying to do and essentially the most
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important thing is always what's the
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founder and the team look like and are
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they going to be able to deliver you
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know on the only on the vision that they
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have so I'm intrigued by this concept of
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the error terms right that it's been
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important to you that these terms be
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explicit and you mentioned right this
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kind of deep purpose that's part of the
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DNA metrics to measure and measure it
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and then paying it forward upon exit why
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is it important to make those as
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explicit as a term sheet for us it's a
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way of it's almost like a litmus test if
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people are buy into that then we're on
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the same page we're on the same
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adventure together you know that's what
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we believe the entrepreneur and era
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believe the same thing that this is why
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you should build companies and that
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there is some robustness in the level of
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rigor around will you're trying to
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change something in society well how are
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you going to measure it because if
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you're trying to build a business you
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measure your traditional metrics revenue
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margin whatever it might be cash burn
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well if you're trying to solve a problem
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in education or health you need to put
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your mind also to how you might measure
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it and some time that's very difficult
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but at least if you put your mind to it
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I think it helps the founders get some
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clarity is to at least coming up with
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some possible way of figuring out
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whether they're making a dent in the
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problem they're trying to address so
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that's kind of just a way for us to
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structure some rigor around making sure
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a few boxes are checked
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before we then go into and have a look
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at how transformative or what kind of
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potential the company might have and
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earlier when we were talking about these
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companies earlier today you use the term
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hybrid capital so I think hybrid
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organization may be a more familiar term
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meaning an organization a company that
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may have a for-profit mission and a
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social mission and that's kind of a
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hybrid is more familiar to focus on and
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scholars of management for sure this
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hybrid capital what is hybrid capital
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and why is you why have you found that
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important well the way I think of it is
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a you know a hybrid being the capital
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coming from both for-profit sources and
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also from philanthropic sources it's not
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a prerequisite we look at a company but
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we think there's this interesting time
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at the moment where nonprofits and
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foundations are willing to invest or
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grant to for-profit companies if they
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believe that that organization is doing
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an amazing job at addressing the issue
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that they care about and they don't
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worry that it's not a non-profit so this
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is happening more and more so if we look
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at a company and they're getting for
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non-profit foundation grants to us an
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indicates they're doing a very good job
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on trying to tackle this mission right
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because some third party has endorsed it
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in a way that an investor wouldn't be
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looking at it the ideal for us is that a
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venture capitalist who doesn't really
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care about the social issue also thinks
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they will consider investing because
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from their lens the things that they're
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trying to check off are being checked
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off and if those two things can happen
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which is rare but a couple of the
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companies we have have that then it
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means you're satisfying these kind of
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two ends of the spectrum and by blending
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that capital you're essentially creating
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you know a stack of different ways in
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which the company can grow and scale and
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to us that's really exciting to find
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those investors investments because the
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grant capital is non-dilutive so as an
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investor it becomes and you get leverage
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out of it and the more companies we find
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like that in the early stages the more
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we can get leverage from our early stage
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investment right right it's very
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interesting because right you have you
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have well philanthropists and investors
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to use the traditional terms applying
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different criteria exactly right and
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seeing in this company something that
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both value exactly yeah that right I get
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that that's what cos of the sweet spot
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yeah exactly so the the last thing I
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wanted to discuss with you is leadership
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you've had you know you've been a leader
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you've worked for it as part of the the
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B team at first CEO of the B team and we
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can you can talk a little bit about the
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B team you've seen a lot of
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extraordinary leaders and now of course
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you're investing in leaders so let's
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let's give folks I let you describe what
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the the B team is and who's involved and
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then let's talk about what you've
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learned about leadership okay yeah so
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the B team was an idea that Richard
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Branson and the Virgin Unite foundation
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had a few years ago which is essentially
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in the beginning of this kind of
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movement of corporate CEOs wanting to
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figure out how they can create more
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sustainable or socially oriented
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businesses Richard wanted to build a
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collection of leaders like that from
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around the world to help each other work
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with each other advocate for issues and
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also pilot different ideas and their own
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organizations so I had volunteered year
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of my time to help but should build this
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idea and essentially Scout the globe to
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find iconic leaders from around the
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world like you know Ratan Tata in India
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or GME Leal from nature in Brazil and
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produce a team that a lot of them
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haven't met before but bringing them
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together on the same page to help
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catalyze a movement that's you know
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picking up pace which is how does
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business move from being myopically
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focused on profit to being focused on
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people planet and profit and that
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movement is I think what we're
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increasingly wanting to see happen and
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the B team is trying to be kind of an
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icebreaker Ennis and a you know at the
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spearhead of it so being exposed to that
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experience and all the various types of
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people that were involved and had a
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heady group yeah I mean all sorts of
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people from Muhammad Yunus for who the
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microfinance been at pioneer to Arianna
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Huffington who's now obviously
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pioneering around well-being and sleep
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and issues that are becoming more what
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better understood in the zeitgeist of
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how do we take care of ourselves so that
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we are personally sustainable so these
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are these kind of shifts that are
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happening in the world that
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organizations like the B team are trying
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to help tip into more of a mainstream
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movement so as you
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think about you know you reflect and
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you're obviously someone who does
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reflect a lot as you reflect on your own
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leadership experiences as a leader as a
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follower interacting with these leaders
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now investing in these leaders what are
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the let's start with you what are the
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the characteristics the practices that
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you aspire to enact as a leader yourself
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well something that I care about I guess
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you know it's a particular thing for me
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is what does the future look like so i
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invest a lot of time and energy and
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thinking about where are we going what's
00:16:06
the possible vision of things in society
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that need to change and systemically
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should be a you know evolved this
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century so the b team is a
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representation of that you know where
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does capitals a move to involve given
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that what we've learned and what we've
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seen with regards to the planet and also
00:16:22
social issues that still are struggling
00:16:24
that applies to other areas like as i
00:16:27
mentioned drug policy where we're seeing
00:16:29
that after 30 40 years of a war on drugs
00:16:31
it isn't working there is a lot of
00:16:32
challenges with it and we need to
00:16:34
rethink our view on it so for me that's
00:16:38
one of the things i like to make sure
00:16:40
that i'm always thinking about what's
00:16:42
behind the next next corner and where do
00:16:44
we need to start you know thinking about
00:16:46
the other pieces i guess goes back to
00:16:48
the idea of like reflection and making
00:16:51
sure that in my world that i'm doing the
00:16:53
things that i think if I died tomorrow I
00:16:56
wouldn't have any regrets and how I'm
00:16:58
spending my energy my time any resources
00:17:00
I might have or how I might you know
00:17:03
deploy them and that goes for also for
00:17:08
people i meet or work with you know so
00:17:11
younger people or anyone that I know or
00:17:13
see your friends to me being a leader in
00:17:16
a community or in a family or with your
00:17:18
friends my particular angle on that is
00:17:21
helping other people make sure that
00:17:24
they're really being bold about how they
00:17:25
live their own lives and are making
00:17:28
courageous decisions because you know it
00:17:31
is very short in a sense life but if you
00:17:34
are bold and courageous about what
00:17:35
you're doing I think as the Roman
00:17:37
philosopher Seneca can set said is life
00:17:40
as long you know if you know how to use
00:17:41
it the problem I think is that too often
00:17:44
we're encouraged to be on a while a
00:17:46
mouse wheel and
00:17:48
not look back and forward enough to make
00:17:50
sure that we're on the right you know
00:17:51
the ladders up against the right wall
00:17:52
because you can climb up it for 20 30
00:17:54
years and realize it's totally wrong war
00:17:57
mm-hm and it's a pretty sad thing to do
00:17:59
that you know I think the longer you you
00:18:02
go on I'm interested in your you know in
00:18:05
your description of vision why is that
00:18:09
important I mean I think it's some level
00:18:11
we could say oh right vision leaders are
00:18:13
supposed to have vision but why again
00:18:19
this is just from my point of view right
00:18:20
I'm not some kind of leadership expert
00:18:22
but unless someone can inspire a broader
00:18:25
mission for me to be a part of a
00:18:27
movement or a mountain to climb or
00:18:29
something like that it's hard to get me
00:18:31
motivated and excited about it so I
00:18:34
think about how do you motivate and
00:18:36
excite people to push themselves to be
00:18:41
who they are and all that they can be
00:18:43
well for me a large part of that is
00:18:46
inspiration and direction and at a point
00:18:49
where you don't feel like there's a
00:18:51
challenge or something inspiring to
00:18:53
follow or you know a moon shot of some
00:18:56
sort I think you can get home home and
00:18:59
people can kind of get into a cycle but
00:19:01
if there is a moon shot if there is an
00:19:04
audacious challenge or if there is a
00:19:05
direction that you believe in and that
00:19:07
you can buy into think that's what
00:19:09
motivates organizations and people and
00:19:11
teams and whether they're a sports team
00:19:14
you know we're a company and that that
00:19:17
whole thing to me if you can't
00:19:18
articulate and paint a picture of vision
00:19:21
I think that there is a strong element
00:19:24
of leadership that is kind of being left
00:19:26
you know an addressed and there are lots
00:19:29
of leaders who are do not do a lot of
00:19:32
that you know I think leaders of cities
00:19:36
and countries sometimes don't do a very
00:19:37
good job of that and they become more
00:19:39
managerial and administrative than
00:19:41
visionary it's just my my personal bias
00:19:45
as towards leaders who can project we're
00:19:48
going there and these the reasons why
00:19:50
we're going and you should come along
00:19:51
yeah yeah so earlier today when we were
00:19:54
talking about leaders you mentioned
00:19:56
another quality and I'm wondering how
00:19:58
that fits in because you've talked about
00:20:00
vision
00:20:01
and you've talked about boldness and
00:20:03
earlier when we were talking today you
00:20:05
talked about coachability and i have to
00:20:08
say when i think about leaders who are
00:20:10
bold and visionary i would think there's
00:20:13
a real risk that they're not that
00:20:14
coachable so to talk to us about a coach
00:20:17
ability well it's kind of this this
00:20:21
double edged the type of thing right i
00:20:22
think the vision and the boldness and
00:20:24
the conviction of what you're trying to
00:20:26
do in the idea i think that's where you
00:20:29
you want that persistence and that that
00:20:34
that unrelenting kind of commitment but
00:20:38
how you get there and how you go about
00:20:39
getting there is where I think you need
00:20:42
to be able to be flexible and coachable
00:20:44
on where you might not see blind spots
00:20:47
or you might not be strong enough
00:20:48
certain areas and so when you look at
00:20:50
our entrepreneur you might agree
00:20:52
entirely with where they want to go but
00:20:54
if it seems like in the first 9 12-15
00:20:56
months it seems like some of the things
00:20:57
they're doing aren't working you want
00:20:59
the entrepreneur to be able to recognize
00:21:01
that acknowledge a set of external
00:21:03
possible advisors and inputs and then
00:21:05
make and synthesize their own decision
00:21:07
as to how they're going to modify their
00:21:08
behavior or their approach if you can't
00:21:11
if you can't embody that kind of
00:21:14
behavior then it becomes very difficult
00:21:15
for anyone to help you out of a
00:21:17
situation so I've invested in certain
00:21:18
companies where the founder would not
00:21:20
change their view on the world even
00:21:22
though it was showing that nothing was
00:21:23
working right and those companies they
00:21:26
and that particular company for example
00:21:28
died because they wouldn't change their
00:21:31
mindset they were fully committed to
00:21:33
exactly how they were executing when it
00:21:35
was clear to everyone outside them that
00:21:36
it wasn't you know working so that's
00:21:38
just a kind of an element that I think
00:21:41
even I think everyone should have that
00:21:43
you know that ability to make sure that
00:21:46
you know when you're 60 70 80 90 you
00:21:49
should always be able to have as we were
00:21:51
speaking about earlier beginners mine
00:21:53
because then you can never be accused of
00:21:56
being stuck in your old ways and you can
00:21:58
never be find yourself in a situation
00:22:00
where you're isolating your perspective
00:22:02
on something and that the whole world
00:22:03
has totally shifted and you you know
00:22:05
because people say oh I'm talk too old
00:22:07
to learn new things or I'm too old to
00:22:09
change my ways and to me that's the
00:22:10
antithesis of what life is about it's a
00:22:13
constant organic
00:22:14
evolution and the moment you think
00:22:16
you've gotten to a point where you're
00:22:17
too old or you know too much I think
00:22:20
that's when a lot of the beauty of life
00:22:22
is kind of lost and to me the biggest
00:22:25
challenge I guess of living would be to
00:22:26
constantly have or try to have you know
00:22:28
beginner's mind yeah great thank you so
00:22:31
much for being with us Derek Emily thank
00:22:33
you
00:22:49
you

Badges

This episode stands out for the following:

  • 70
    Most inspiring
  • 70
    Best concept / idea
  • 65
    Most influential
  • 60
    Most quotable

Episode Highlights

  • Finding Purpose in Crisis
    Derek shares how moments of crisis led him to discover his purpose.
    “Whenever something terrible happens, I ask bigger questions about my purpose.”
    @ 01m 15s
    December 21, 2016
  • The Importance of Reflection
    Derek emphasizes the need for time to reflect on one's purpose and direction.
    “Carving out time to think about the bigger picture is crucial.”
    @ 06m 19s
    December 21, 2016
  • Launching Arrow VC
    Derek introduces Arrow VC, a venture capital fund focused on social impact.
    “Arrow VC aims to support companies addressing social and environmental issues.”
    @ 07m 19s
    December 21, 2016
  • The Importance of Visionary Leadership
    Leaders must articulate a clear vision to motivate teams and organizations.
    “If you can’t articulate and paint a picture of vision, it becomes difficult.”
    @ 19m 18s
    December 21, 2016
  • Embracing Change and Coachability
    Successful leaders must be flexible and open to feedback to adapt their strategies.
    “If you can’t embody that kind of behavior, it becomes very difficult for anyone to help you out.”
    @ 21m 11s
    December 21, 2016
  • The Challenge of Lifelong Learning
    A constant evolution of mindset is essential to avoid stagnation as we age.
    “The biggest challenge of living would be to constantly have a beginner's mind.”
    @ 22m 25s
    December 21, 2016

Episode Quotes

  • If it’s frightening, it’s probably the right place.
    Leadership: Finding the Next Mountain to Climb
  • Life is long if you know how to use it.
    Leadership: Finding the Next Mountain to Climb
  • You should always be able to have a beginner's mind.
    Leadership: Finding the Next Mountain to Climb
  • The moment you think you know too much, beauty is lost.
    Leadership: Finding the Next Mountain to Climb

Key Moments

  • Purpose Discovery01:06
  • Arrow VC Launch07:19
  • Courageous Living17:31
  • Visionary Leadership19:18
  • Coachability20:17
  • Lifelong Learning22:25

Words per Minute Over Time

Vibes Breakdown

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