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“So, if you think about it, to me trust is not – it’s not something that we actively create. Trust is a
byproduct of being radically honest through radical self-enquiry and then being brave.”
Welcome to the Reboot podcast.
“Authenticity is the alignment of the head, mouth, heart and feet: thinking, saying, feeling and
doing the same thing consistently. This builds trust and followers love leaders they can trust.” –
Lance Secretan.
So many entrepreneurs seek to model their leadership after the high-profile, successful giants.
Should I be a leader like Steve Jobs? How can I be more like Jeff Bezos? What should I be doing
right now to be like Travis from Uber? These are not only questions without answers, they are
the wrong questions. The real question is, “Who the fuck are you? You are not Steve Jobs and
you are not Jeff Bezos; you are you. And what does the leader within you look like?”
In today’s conversation, Jerry is joined by Evgeny Shadchev, co-founder and CEO of Makers
Academy. Ev wrestles with the question of whether it’s possible to scale an organization built
around trust, or does success require a leader who governs by fear? Together they discover a
more beautiful, a more fundamental question: who is Evgeny? In that answer, they may find a
personal path to alignment and more effective leadership.
**
A quick reminder, as always, you can head over to reboot.io/podcast where you can find the full
show notes from this conversation with Evgeny, including key quotes, links to Makers Academy
and Evgeny on Twitter, as well as the transcript from the conversation. I’d also encourage you to
stay tuned to the end of this conversation, where we have a full, eight-minute discussion from
one of our Reboot peers members, Bobby Brannigan. It’s a great story that you don’t want to
miss; but now, a word from Ali about our bootcamps.
“My name is Semira Rahemtulla and I’m a co-founder of Innerspace. I would say it was really
enlightening; it was really, really enjoyable and I learnt a lot. ”
“Albert Lee, founder of All Tomorrows. It really changed my life.”
“My name is [Inaudible 0:02:56]. It was a really amazing experience.”
“My name is Mat Ellis and I am the CEO and founder of Cloudabilty. This thing, if you are
ready for it, it can really change your life and your career, and as a CEO, you owe it to your
stakeholders, to your staff, to your investors and to your customers to be a better CEO, to take a
step, get these four days, and I guarantee, you will come out of it a better CEO.”
Join us for our upcoming co-founder bootcamp March 2nd through the 6th. Applications are due
by January 31st. Learn more about this and our other 2016 bootcamp offerings, including our
CEO bootcamp in Italy at reboot.io/bootcamps.
**

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Jerry Colonna: Hey Evgeny, how are you? It’s good to see you again.
Evgeny Shadchev: Hello Jerry; yes, I’m fine, thank you and it’s amazing to see you. How are
you?
Jerry: I am really well, thank you; thank you for asking. It’s a beautiful day here in
Boulder and I’m planted and grounded and I feel really good. Hey, before we get
started too far, why don’t you just take a moment and introduce yourself and tell
us a little bit about the company and I guess, even how we first met?
Evgeny: Sure. My name is Evgeny and I am a co-founder of Makers Academy, a coding
bootcamp in London. We help complete beginners become professional software
developers and get an awesome job and we know we are doing a good job when
our students, our alumni describe their Makers Academy experience as life-
changing. We first met, I think, yes in February this year, when I went to the CEO
bootcamp in Colorado. I came across one of your videos on YouTube pretty much
by accident, I think someone tweeted it, it was your talk at the Pioneer Festival in
Wien, and I really, really enjoyed it. I felt like I could connect to you, strangely,
on YouTube. And so I Googled your name, I watched a few more videos, I found
a website and then I learnt that you are running bootcamps for CEOs and I
decided to apply. I went there and it was a great experience. I’m so happy I went
to that CEO bootcamp in February.
Jerry: Thank you for that and thank you for coming, you really made a difference at the
camp because I remember you showing up with such presence and authenticity
and you know, I remember too, from that first experience that that was the week
where there was an opposition leader in Russia who had been killed.
Evgeny: Yeah.
Jerry: And I remember you feeling – because obviously you were not born in the UK; I
think you were born in Russia and emigrated to the UK –
Evgeny: To London, yes.
Jerry: – and you were feeling that – the pain of that.
Evgeny: Yes, you are absolutely right; I think it was the second to last day of the
bootcamp; I got a text from my wife, who told me that one of the leading
opposition figures in Russia was shot right next to Kremlin, which was on one
hand, it wasn’t completely unexpected, on the other hand I remember I was really,
really sad that it happened because there is virtually no opposition in Russia
anyway, and the very, very few people who do stand up against the regime, they
have to face the consequences and they are often risking their lives.

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Jerry: So, you know, I think it’s always worth noting that you know, we all operate in a
larger context; we operate in a world and there is violence and there is all that and
I just wanted to take a moment and acknowledge that that is true, and sort of out
there.
Evgeny: Thank you, Jerry.
Jerry: Sure. So, you know, when we talked on email, you talked about some ideas about
what you wanted to talk about today and why don’t you take us through a little bit
of that? What is on your mind? Something about trust?
Evgeny: Yes, that’s correct. Trust has been on my mind a lot recently; let’s say throughout
the year. I have been running – I founded the company three years ago and I must
first thank you; I don’t really have too much experience and I am learning as I go,
like all first-time CEOs do, and one of the questions that has been on my mind is
why are so many companies seem to be built on fear? Like the process is there –
the process that we normally expect to see in companies, like the power hierarchy
is, so people firing others on the spot, the process is designed specifically to
prevent abuse. It feels like many companies operate on the assumption that their
own employees can’t be fully trusted, and this somehow didn’t feel right to me.
So, I guess, for the last year or so, my team and I have been exploring the
question of what if it is possible to lead or to build a company in a different way?
Why a young company, a startup, when they are just a couple of founders and no
one else, is behaving according to very different rules. There is a lot of trust, there
is a lot of alignment, a lot of stuff is getting done and then as companies grow,
they somehow become – or rather, they become more fearful or so it seems, and
we’ve been trying to understand it and change it, and some things work amazingly
well. Some of my successes of the last couple of years can be attributed to just
trusting people more and at the same time, I’ve got more questions than answers:
is it really possible, maybe what I am trying to do is completely crazy and maybe
there is a reason why the world, or let’s say, high-performing companies operate
in a certain way. So, all these questions related to trust have been on my mind a
lot.
Jerry: So, the question you are really grappling with is, let me see if I’ve got it and
mirror it back to make sure I understand it, one of the things you noticed is that
amongst your co-founders and that first team, there was a high degree of trust –
Evgeny: Extremely high.
Jerry: – and the fear or the concern is that as the company grows and as it becomes more
successful, that there’s going to be a loss of that trust, and your question is in a
sense, is it inevitable that as a company grows, is that loss possible? And it would
be particularly painful for you, I imagine, because one of the things that you
noticed and I think you made reference to this to me and other consequences is
that you found that when you lead into being more trusting yourself, and as a

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result we are more trustworthy, but there is a correlation being able to be trusted
by others and therefore trusting others, that the company performance was better.
Evgeny: In some respects, yes, it’s not a silver bullet by any means, or it’s not the only
solution, but some really good things that happen can be attributed to trust; people
working in situations where they really, really trusted each other.
Jerry: So, that’s really helpful to distinguish. Tell me a story of when that has worked
out well for you in the last few months.
Evgeny: So, in the last few months, I think – let me tell you a conversation I had with my
investor. We are a venture-backed company and we got the board and he is on the
board, and our relationship had been slowly improving over the last year, but it’s
still wasn’t as good as I wanted it to be. And at some point, we sat down and we
had a very frank and open conversation about trust or level of trust that was very –
I think fairly difficult for both of us, but at the same time, it was extremely helpful
because by looking back I think it was a turning point in our relationship. I can’t
put a number in it, but in my subjective experience, our relationship became
significantly better because we just started trusting each other much, much more
and as a result our board meetings became more productive and less tense, and
overall it changed for the better I think for both of us.
Jerry: Let me bring your attention to something; rather than answering your question
directly, I want to take you through what I think you already know to be true. So,
using that as a jumping off point, what was the first thing that you had to do to
start that process? Do you recall?
Evgeny: You mean thinking about the trust or the specific conversation?
Jerry: So, if I remember correctly, what you said was, you’ve had this relation with this
investor for a while, it wasn’t – it did not exhibit a lot of trust –
Evgeny: Mm-hmm.
Jerry: – and then you made a decision.
Evgeny: Mm-hmm.
Jerry: What did you decide to do?
Evgeny: To be more open with my feelings and my perception of this situation.
Jerry: Even though you didn’t feel that you couldn’t trust them, not entirely.
Evgeny: Not entirely, but at the same time, it still felt like the right thing to do. Was it – it
was a difficult conversation, but I think it was a good one.

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Jerry: Yeah, so one of the core components of those difficult conversations and you’ve
seen me do this talk before, what I often referred to it as being fierce, not
ferocious, being direct is someone has to go first.
Evgeny: Yeah.
Jerry: And so I think you did that with a few little micro-steps; the first was, you cut
through the self-delusion, which was – a self-dilution of state would be to blame
him for everything.
Evgeny: Oh, that would be self-delusion then. If anything, a [Inaudible 0:15:04] was mine.
Jerry: Right. So, the first thing you had to do was be honest and direct and fierce with
yourself, which is painful because –
Evgeny: Yeah.
Jerry: Tell me, you just smiled and nodded –
Evgeny: Mm-hmm, I did.
Jerry: – because you had to acknowledge that you are not innocent.
Evgeny: I’m not.
Jerry: Right and then you had to be brave. So, first was a kind of honest,
acknowledgement and the second step was a bravery, and the bravery was in
naming the situation and putting words to it because again, most people won’t
acknowledge their own complicitness in creating difficult relationships.
Evgeny: Yeah.
Jerry: And the second thing is most people are not brave enough to name it and to speak
it and to approach it because he could have just said, “Screw you; I’m not going
to talk to you about this.”
Evgeny: Easily, yes.
Jerry: And he didn’t. So, if you think about it, to me trust is not – it’s not something that
we actively create. Trust is a byproduct of being radically honest through radical
self-enquiry and then being brave.
Evgeny: Yes.

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Jerry: Those are the necessary agreements and then if you establish it – and in a sense
you begin to trust your own self. Wait a minute, I got this, I can do this, I can
have this conversation; it’s scary, it’s difficult and then you –
Evgeny: But ultimately it’s the right thing to do.
Jerry: Well, I think that the pain of it, well, tell me about ‘ultimately it’s the right thing
to do.’ How did you it was the right thing to do?
Evgeny: I mean, what’s the alternative there?
Jerry: Beautiful.
Evgeny: I mean, I remember at the bootcamp, you asked us a question, “What needs to be
said that is not being said?”
Jerry: Yeah.
Evgeny: This question stayed in my mind. I have come back to it again and again, when I
go through different challenges and yes, so I was thinking, okay, what am I not
saying, and then I realized the actual there are quite a few things that I am not
saying and it will probably be best if I bring it to the surface.
Jerry: Yeah, that question is part of three questions that I have taught myself to ask;
what am I not saying that needs to be said? What am I saying that is not being
heard? What’s being said that I am not hearing? Three questions.
Evgeny: Yes, three great questions.
Jerry: The first question was actually taught to me by my therapist, in response to
repeated and persistent migraines. I would have these migraines and finally she
would cut through it and say, “Well, what are you not saying that needs to be
said?” And when I started training myself to say things that even though it’s
scary, even though it’s difficult, the migraines started to abate.
Evgeny: And Jerry, I so understand you because I felt the same; I realized that at some
point I realized that trust is closely related to stress. In fact, one of the reasons I
went to your bootcamp is because I guess I was looking for more talks to figure
out how to be less stressed. When I came to Colorado, I was not in my best shape
mentally and then I realized that actually asking this question and optimizing for
trust, completely trying to be more open, more vulnerable, more authentic and
trying to trust other people in the world in general more, leads to a less stressful
life because it enables high conversations, it enables transparency, it enables – it
lets me be myself. It allows me to share – that you share and you hear when it
happens. It lets me to receive and deliver a negative feedback when there is an
implicit trust that no one is going to retaliate, but instead we are just going to

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discuss this problem. And these things, they really make my life slightly less
stressful, which I guess, as an entrepreneur, I really appreciate.
Jerry: Well, I appreciate your naming it that way. I want point out – as I often talk about,
we have this famous formula we use in Reboot, which is
Practical skills + Radical self-enquiry + Shared experience = Enhanced
leadership and greater resiliency.
You just were speaking to the greater resiliency piece; I am going to make an
argument too that everything that you just described as a consequence of that
commitment to being clear, being fierce, result in you being a more effective
leader.
Evgeny: I would like to hope so.
Jerry: You would like to hope so. Every attribute that we talked about, transparent,
clear, consistent, trustworthy, trusting, are all attributes of strong, effective
leadership and we know that because of the way people respond to that. They
don’t necessarily jump up and do whatever you tell them to do, but – when you
have the audacity to be yourself and create conditions in which you allowed to be
yourself, you inadvertently create the conditions for other people to be
themselves.
Evgeny: Can I give you an example of exactly what you are describing?
Jerry: Tell me.
Evgeny: A couple of weeks ago, we had a team meeting at our company, all hands
meeting, and one person in the team said that – I’m quoting him, “I’m terrified
that we’ll get significantly more students.” To me, that was both scary and
wonderful at the same time. It was scary because, oh my God, someone – most of
the team are trying to grow the company and get more students and somebody is
terrified of this process. But at the same time, I realize how beautiful this moment
is because this person was comfortable sharing this feeling knowing that instead
of calling him crazy, the team would respond, “Oh wow, why do you feel this
way? What can we do about this? what is happening?” And come into this
situation with an open heart and then we started discussing it and I think we got
much closer to the solution. But thinking back at the situation, I’m still grateful to
him for saying that because otherwise if I were the team, if I were not aware of
this problem, then part of the team would try to get more students, part of the
team would try to, let’s say review this effort and everyone would be left
wondering, “Oh my God, what is going on?” Whereas, the situation was brought
to the surface and they discussed it very, very openly.

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Jerry: Yeah, I think it’s a brilliant example of the way authentic, trusting, trustworthy
leadership creates the conditions for more effective manifestation of the
operational goals. So, here you were, there was something magical that got
created in that team where this colleague could speak to the politically incorrect
fear that they had. The counter-intuitive fear is, “Oh my God, what if we actually
are successful?” No, the truth is, and coaches know this a lot of time, all over the
place –
Evgeny: Mm-hmm.
Jerry: – many, many people are just as afraid of success as they are of failure –
Evgeny: Yeah.
Jerry: – because of all sorts of complicated reasons, and when we create the conditions
within an organization we can’t name that fear, you are absolutely right, it gets
driven underground and it become an unconscious sabotaging force within the
organization. Whereas, by surfacing it, you did two things; the example shows
two things: one, the benefit of surfacing it is that you can speak to the product
design process, you can speak to the UI process, you can speak to the user-
engagement process acknowledging that there is this feeling. The second thing
and the more important thing, you noticed how the rest of the team responded;
they rallied to that person and so there is something very special that occurred just
because somebody said something really clear and direct. That was beautiful. So,
what we have done is we have just sort of named some of the important
components to it. I want to go back to your core question; okay, we are going to
do a little coaching on this, so the core question is, in effect, how do I maintain
this, isn’t it?
Evgeny: Mm-hmm.
Jerry: So, what’s your fear?
Evgeny: My fear is that it’s going to scale; my fear is that it worked beautifully well when
there are two founders, it still works really well with a very small [Inaudible
0:25:29] team, but as we grow from two to five to ten to twenty people and then
more, how can we maintain it? How can we [Crosstalk]
Jerry: What makes you think you can’t?
Evgeny: Because trust is built over time and face to face – face to face for a conversation,
for sharing experiences, and if companies grow as – as the team becomes bigger,
it becomes literally impossible to maintain a very close, deep connection with
everyone.

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Jerry: Okay, so what you are asking in a sense is, how do the values and vision of an
organization get maintained when you can no longer rely on the personal
transmission from co-founder or founder to the next level?
Evgeny: Yeah, mm-hmm.
Jerry: Because really – again, I think trust as a byproduct of something else. It’s the
byproduct of the values that you have and one of the values that you are starting
to identify and really name is the value is to be authentic. The value is to be real.
Evgeny: Yes.
Jerry: The value is to lean into things that you are afraid off as well as things that you
are happy about. The value is to speak directly and clearly or in Jerry’s parlance,
speak fiercely even though it’s scary and the consequence of that is trust. If that is
the case, then, the task becomes how does a CEO who – one of their prime
responsibilities is to embody the values, how does that – how do you maintain
that as the team grows?
Evgeny: It’s a challenge.
Jerry: Because there is an implicit fear here and the implicit fear, and you named it
earlier before, is that when you look at larger companies that are more successful
financially than yours, what do you presume to be true about their trust within
their organization?
Evgeny: I presume that the level of trust is lower. I see processes specifically designed in
order to work in situations of low trust, for example, big companies mainly, if you
have two co-founders, there are no things such as budgets and then as the team
grows, somehow the team is to decide, okay, how much money goes in which
direction, where the limits are and somehow it feels like the larger the company
has become, the harder it is to trust irrespective of the person to just use their best
judgment to do what is right, and it is scary because it is exactly what I am trying
to do. One of the things I am telling my team almost every week is that I want
them to do what they believe is right and what is in the best interest of the team
and the company.
Jerry: Okay, so I think what – my advice would be to not necessarily focus on the output
as much as the levers that create the conditions that you are looking for in the first
place. So, for example, you can say, “Look at how trusting we are, we don’t have
this budgetary process where the two co-founders are looking over each other.”
Okay, that is not the reason you trust each other. It’s not the lack of process –
Evgeny: That’s a consequence, yes.

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Jerry: That’s a consequence; and so the real reason you trust each other is you are real
with each other. Now, if you create conditions where all of the senior leadership
start to embody the same values where they start to embody the value for
example, of going first, the way you did with your investor, you will eventually
need processes, you’ll need expense reports, you’ll need tracking mechanisms and
planning mechanisms for sure, but you’ll not need them because you don’t trust
each other. You’ll need them just for clarity sake. The real challenge is, how do
you personally hold on to the ability to continue to be real and authentic,
modeling for the rest of the team, that style of leadership even as the company
succeeds?
Evgeny: [Exhales deeply]
Jerry: Yeah, hold on to that one.
Evgeny: Okay.
Jerry: So, notice that one of the things that we are ending up with, who else in the
company, aside from that employee is afraid of getting more students?
Evgeny: I think at least one or maybe two more people.
Jerry: How about you?
Evgeny: To some extent, yes. The thing is – and I’m going back to trust – we are – when
we accept our students – we only accept them if we believe that we can help them
become great junior software developers. They trust us to do that and we don’t
take it lightly. Accepting more students, or attracting more students is one thing,
but actual delivering on the promise is another thing. So there is – and yes, I know
it’s scary including for myself to think, “Okay, if we get 500 more students
overnight studying in January, will be still be able to deliver on our promise as
well as we’ve been doing it last year?”
Jerry: So who else in the company is afraid of the company succeeding?
Evgeny: Well –
Jerry: I wish they could see your face right now.
Evgeny: Well, I guess everyone to some extent, because –
Jerry: Yeah, I worry about you.
Evgeny: And me too, because it’s – I really care about the quality of what we do, and I do
acknowledge this year we get more students and we still need to deliver this great
service.

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Jerry: So, this is my point Evgeny, the question is, how do we hold on to our values so
that we remain the trusting and trustworthy environment that we are as we grow?
But really what it feels to me is that there is a deeper fear which is, what is going
to happen to this company if we continue to succeed?
Evgeny: There is, yeah.
Jerry: So, what are you afraid of as the company potentially succeeds?
Evgeny: I’m afraid of promising to lot of these students something that we will fail to
deliver –
Jerry: And what if you do that? What if the company – yeah, go ahead.
Evgeny: I’ll feel bad; I’ll feel really horrible.
Jerry: And why should you feel horrible? There are plenty of big companies that over-
promise and under-deliver.
Evgeny: And that is exactly I am – why I am building a new company instead of working
for one of those big companies. For me, it’s – for me and for us as a company, it
is really important to deliver on the promise. Our work that [Inaudible 0:33:51]
our students sign a contract.
Jerry: That’s beautiful. What happens if you don’t deliver on the promise? Name it.
Evgeny: I guess I’ll be really disappointed if not plainly ashamed of failing to deliver.
Jerry: So, the implicit in the potential growth isn’t just the fact that the company is not
going to be as trusting as it is now, but that you may find yourself over-promising
and under-delivering; not delivering on the trust that students have placed in you.
Evgeny: Yes, and this is real scary.
Jerry: Why is it so scary Evgeny?
Evgeny: I’m not quite sure; it’s – I don’t know – but I do know that if I promise something
and then fail to deliver, emotionally I will be in a frigid dark place.
Jerry: Yeah, I know you will. Why? Why will you think poorly of yourself?
Evgeny: Because I like to think of myself as a reliable person who delivers on what I
promised.

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Jerry: Oh, that’s the kind of leader you’d like to be. That’s the kind of adult you’d like
to be. That’s the kind of man you’d like to be.
Evgeny: Yes.
Jerry: I’m not pointing it out to say that there is something wrong here, but I’m
connecting it to a deeper, existential and emotional hold that you have. Okay, now
this is going to sound like a very strange [Inaudible 0:35:41]; tell me again, why
you left Russia.
Evgeny: I left Russia because I felt like I didn’t fit in the society?
Jerry: What was it about the society that you did not fit in with?
Evgeny: The values.
Jerry: What values?
Evgeny: I felt like I couldn’t be myself and just being authentic, just saying what I think
and being myself and trusting the society at large was difficult.
Jerry: So, I imagine that you lived in a society where people said one thing and did
something else?
Evgeny: Yes. It happens.
Jerry: And that is an awful place to live.
Evgeny: It was, yes.
Jerry: And so, if we think about it for a moment, the fear, perhaps, the fear is that if you
find yourself successful in terms of the numerical number of students, but not
successful in delivering and maintaining the same level of quality, and not being a
trusting and trustworthy company, that you’ll have fallen into being that kind
person back in Russia.
Evgeny: Yes, I think we are getting somewhere Jerry.
Jerry: This is why it’s so important to you. It was so important to you that you uprooted
yourself and moved to a completely different country. This is existentially vital
for you to live in an authentic way. That is what is at stake here.
Evgeny: It was – yes, I guess authenticity played a big role; when I moved to London over
nine years ago, it was – I guess it was an attempt to find a new place that would
be – where I would be more authentic, more myself, and where I could find other
people who would allow themselves to be more authentic. Even relatively simple

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things, for example, Russia is not the friendliest place for homosexual people, and
even though I am not homosexual, I am afraid – my friends are, and it was fairly
difficult to live in a situation when I had to say one thing at one context and other
thing in another context. I just wanted to be in a society where everyone could be
themselves whoever they are, and yes, I guess trust and maybe not having to
pretend that you are someone else was a big part of it.
Jerry: So, the inquiry was around how do I maintain trust in an environment and yet,
where we have landed is Jerry, I’m worried that the exterior of me isn’t going to
match the interior of me as we grow and that the interior – the exterior of the
company doesn’t match the interior of the company, because the consequence of
when the interior and exterior are in alignment is trust.
Evgeny: Yes.
Jerry: The output is trust. So, the fear is that you’ll be in a place again perhaps where
you say one thing in one situation and another thing in another situation.
Evgeny: And when it happens, I find myself in a real difficult place emotionally.
Jerry: Our mutual friend, Parker Palmer, we know through his writing often says that his
depression was always linked to when the interior and the exterior were cross
ones with each other.
Evgeny: Oh yes.
Jerry: Yeah, you know that feeling.
Evgeny: Yes, I know that feeling.
Jerry: So, what we are talking about, even though we are talking in a sort of theoretical
way about trust, what we are really talking about is authenticity; is this deep and
profound desire to be Evgeny all the time [Crosstalk] and not in conflict; so what
do you think of that?
Evgeny: It certainly sounds right. I – it strikes a chord.
Jerry: So, if that is true, then let’s get to your question and your core question is, how do
I maintain trust, a trustworthy and a trusting environment as the company grows?
Evgeny: Mm-hmm.
Jerry: When I look outside and I look at all these other companies, they don’t seem to be
trusting;
Evgeny: Mm-hmm.

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Jerry: Why did I just emphasize that? “When I look outside” there is the answer my
friend. Stop looking outside.
Evgeny: Look at myself?
Jerry: Amen. If you really maintain the trusting environment that you’ve built, stay
connected with that inner core of yourself and in effect, what I am suggesting you
do is stay vigilant not about keeping the trust, but stay vigilant about being
authentic.
Evgeny: Yes. I am trying to do my best and it, at times, is difficult, but it’s important.
Jerry: Yes, and what makes it difficult? Name those things.
Evgeny: Fear. It always blows down to fear. Whenever I feel like there is a lack of trust, it
is always accompanied by fear; like what is going to happy if I am myself? What
is going to happen if I just say what I think or yeah, just things as they are or share
my feelings and share my vulnerability.
Jerry: What was the name of the employee who said that they were terrified that they
might get new students?
Evgeny: Will.
Jerry: All right, can you be as brave as Will?
Evgeny: I’d like to be.
Jerry: Yeah. I’m going to give this company, Makers Academy, a new mantra and it’ll
make Will really happy.
Evgeny: Okay.
Jerry: Be brave as Will. Be as brave as Will.
Evgeny: Thank you, Jerry.
Jerry: You see what I am saying? And in that sense, even though you are the CEO, you
are holding the values, you are holding the vision, in that moment, when we say
‘Be as brave as Will,’ even though he was terrified, he was terrified to tell you
that he was terrified, but he overcame that. In that moment, he was leading.
Evgeny: Yeah.

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Jerry: The way you are going to scale this is hold yourself first to the mission where the
inner and the outer map and then hold each other accountable to the same thing.
And have that conversation; co-hold that within the organization. Everyone can
hold on to that as a value. If you set your sights on the target of being real and
authentic, you will, by default, create a trusting environment even as you scale.
Evgeny: I will try to do my best, but Jerry, I know, it is scary.
Jerry: It is scary.
Evgeny: Yes.
Jerry: I think you did something most people would be too afraid to do and that is you
even spoke to an investor about that.
Evgeny: Well, it wasn’t easy, but as I said, it felt like it was the right thing to do and –
Jerry: So hold on to that; hold on to ‘the right thing to do’. How did you know? Where
did you feel the right thing – is it in your head?
Evgeny: In my body, I just became more relaxed –
Jerry: You feel it in your body; when you connect with “the right thing to do” it lives in
the body. I often think of my stomach, it’s like that gut feeling, “I hate this, I have
to do this thing I don’t want to do, but I know it’s the right thing to do because my
stomach is telling me it’s the right thing to do.”
Evgeny: Yeah.
Jerry: And if I can trust my stomach, trust my gut instinct, it’s an expression of being
authentic and true. And then all of a sudden, the relationship shifts. Not
everybody will respond and meet you the way that investor did. Not everybody
will respond and meet you the way Will did, but most people.
Evgeny: And also why – and on this note, what I find is that not just most people, but more
people than I expect. And what I guess, one of the lessons I guess, I learnt here is
that people in general tend to behave the way you expect them to behave. If I hear
that others are – that everyone else – basically most people are – all people are
basically trustworthy and reliable human beings and behave accordingly, then
they tend to return the favor. Whereas, if I start the relationship by trying to
protect myself and minimize the damage that hasn’t happened yet, then it’s more
likely that others will behave in a way that I expect them to behave. So, I did have
a few situations when I thought, ‘Oh my God, this is not going to end well” and
I’m trying to trust this person, but they are probably going to just retaliate and do
something bad and you know, more often than not, it doesn’t happen. When I
trust people, I get more trust back than I expected.

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Jerry: You just said it. You said basically a fundamental Buddhist teaching. When I trust
people, I get more trust back than I expected. Absolutely right. Well, I want to
thank you, this was a wonderful conversation and I appreciate the trust that you
placed in me in being brave enough to come on – brave as Will to come on this
show and to talk about this. I’m so admiring of your tenacity and your desire to
grow as a leader. It’s really admirable and it’s a delight and it’s a pleasure every
time I encounter you. So, thank you.
Evgeny: Thank you, Jerry; and it’s been a pleasure talking to you, as always.
**
A Reboot peer group is a hand-selected group of entrepreneurs and leaders who meet in
supported, Reboot coach-facilitated sessions twice a month. So, what are these groups really
like? We asked a peer group member, Bobby Brannigan, to share his experience with Reboot
facilitator, Andy Crissinger.
Andy: I felt we could start with you introducing yourself and telling us a little bit about
your company.
Bobby: Sure, thanks Andy, thanks for having me. My name is Bobby Brannigan, I’m co-
founder and CEO at Mercato. Mercato is an online marketplace to match
consumers with their favorite specialty food shops, but focuses on building
software that makes it easy for 100,000+ specialty food shops in the United States
to sell online and facilitate local and national delivery. My last company was
Valore Books, which is an online marketplace for college textbooks, where we
connected millions of college students with book stores and whole sellers and
publishers nation-wide, and I started that business out of my dorm room. I grew it
for 13 years, we never raised any money, and as you can imagine, I learnt a lot of
hard lessons along the way, and I ended up exiting Valore about a year ago and I
took a lot of time reflecting on what went right, what went wrong. And one of the
things I realized was that I spent less than 1% of my time on things that really
impacted the company positively and my mission for my new business is to dial
that number out by surrounding myself with great people and being more
thoughtful than ever.
Andy: Tell us a bit more about what are the challenges you are facing in your role as a
founder?
Bobby: Sure, you know, one of the biggest challenges that I face as an entrepreneur has
been, you know, navigating the waters of solving hard problems while under
extreme stress. You know, that’s been even harder when I was a first-time
entrepreneur, because you don’t really have the experience, you don’t really know
what to expect, and you start a business, you have high hopes, you have big
vision, but as with solving any hard problems, there are things that you just can’t

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possibly predict or know and you know, the answers are not publically available.
So, you try to get the best advice that you can, but sometimes there’s no one there
to help so you just have to go with your best logic. For me, I faced loss with
[Inaudible 0:50:11] at Valore and the most intense stress that I endured was when
I got sued by the four largest publishers in the country for eight million dollars.
That was at a time when we had been in business for about four years, we were
500,000 dollars in debt, and you know, that came from the home equity line of my
parents’ house, 250 grand in credit card debt and you know, also some money I
borrowed from some scary people in Brooklyn. Nonetheless, failure was not an
option and at that point, you know, when you are in that kind of situation you
really don’t have anybody to turn to. In my particular scenario, I didn’t want to
scare my employees away, let alone letting them know that we had a tense
situation going on and I didn’t want to pass the stress on to my family because I
didn’t want them to get scared that they could possibly lose the house. I also
didn’t want to share anything with friends from home because who knows what
can get back to the scary people. So that would not have been very good. So, what
I ended up doing is, I internalized the stress and I fought publishers for about 12
months until one day when I was driving from work, I ended up blacking out and
I woke up on the side of the road. That was a really scary moment that I had, you
know, where it was tons of stress and you are doing with a team, but it’s hard to
think under clouded vision. In that scenario, although we ended up settling with
the publishers for a modest amount and we convinced our insurance company to
pay for it and we got away from that one, but it was pretty stressful for us.
Andy: Bobby, I’ve heard you tell that story before and it never ceases to amaze me how
much stress you were under and how intense that time was for you. So, it sounds
to me like you’ve really learned how not to do things, how not to manage stress,
and I’m curious what it has been like this time around, with a group of peers that
you can trust to bring that stress and those really hard problems to.
Bobby: Yeah, it’s been pretty amazing so far; I mean, I wish I would have had the group
back then when I underwent all that stress, but right now it’s great to have that
group available going forward because you know, you can’t be open and honest
with everyone about your business because you don’t want to scare people away,
you don’t want to get people nervous because that is going to upset their ability to
do what they have to do, and at the same time, there are not a lot of people that
can actually relate to these situations. So, having a group you can turn to is
extremely beneficial and it allows you, you know, not only to spend more time
thinking about these issues and help you solve them, but hearing yourself explain
them out loud and getting people to question, you know, different routes that you
might think about taking and that kind of stuff is invaluable. So it’s been really
good so far.
Andy: You know, one of the unique aspects of our peer groups is that we have this
ground rule of no fixing or saving; and I wonder if you would share a little bit
about what it’s been like to be grouped with other smart, driven entrepreneurs

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who are used to being problem solvers. What’s it like being in a group where you
are holding back that urge to fix each other and instead leaving with inquiry, open
and honest questions and listening?
Bobby: Well, you know, it’s been a little bit hard, especially in the beginning to not try to
fix, because as an entrepreneur, it’s like we are just fixing stuff all day, you are
just looking for problems to fix. So, it’s a natural instinct that you want to fix a
problem, but what’s really helped me going through the process is the positive
outcomes that I had from people not trying to fix me. As we went through just
these detailed conversations and you know, really deep into problems, what I
found is that I formed the best conclusions and the best outcomes when I come to
it myself. It’s kind of strange, I don’t know why the brain works that way, but you
know, when I hear myself say something out loud, it’s very different than when
somebody gives you some prescription and they say, “You really need to do X.”
And it’s happened to me several times with the peer group so far that had resulted
in massively positive outcomes for me. You know, one scenario in particular is
that you start your business and you are under tons of stress, and there’s lots of
unknowns and what I had to call them all these unknowns, I like to call them
‘dark alleys’ and lots of entrepreneurs are scared to walk down the dark alleys.
They are scared to walk down the unknown, to see what the unknown is, so they
deny it, and it haunts them and eventually that is one of the reasons why they
potentially didn’t succeed, because they didn’t really pursue what was there, or
potentially could be a big problem for them. So, I made it you know, a strong
focus of mine to focus on going down those dark alleys frequently and in doing
that, it can get, you know, pretty scary. I mean you go down them, and it’s
unknown and you don’t know what you are going to come back with. So, you
know, having a group to support you along the way has been great because
without that, your self-doubt can kind of cripple you a bit, and if you really don’t
listen to it then you might just take on less new ways because you’ve hit your
threshold.
Andy: Bobby, has anything surprised you about your time in your peer group?
Bobby: Yeah, I think the thing that has surprised me most about being in a peer groups is
just a value in hearing yourself answer these questions and how valuable it is to
have the answers come out of your own mouth instead of people prescribing stuff
to you.
Andy: What’s it been like to know you have your group there and that you are not alone?
Bobby: You know, it’s been really great; I guess you know, mostly because I feel I can
take on more stress and more risk and I’ve been able to solve problems best, and
also be more mindful on how to build a great organization because when I built
my first company, it was really all about executing tasks and that is doing this and
doing that, and just getting shit done. With my new company, I am just really
focused on building a great organization and like Jerry always says, “Building a

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machine that builds a machine” and you know, it’s been great to have that group
to really think in a much deeper sense with people that share the same challenge
and they really trying to grow and really get out of that comfort zone just as I am.
That’s been really excellent for me.
**
So, who do you turn to? What if you had a community of peers who were committed to
supporting you and solving your greatest challenges, a group you knew you could always count
on? There is great power in knowing you are not alone. Learn more about Reboot’s peer groups
and apply at reboot.io/peers.
**
That’s it for our conversation today. You know, a lot was covered in this episode from links, to
books, to quotes, to images; so we went ahead and compiled all that, and put it on our site at
Reboot.io/podcast. If you’d like to be a guest on the show, you can find out about that on our site
as well. I’m really grateful that you took the time to listen. If you enjoyed the show and you want
to get all the latest episodes as we release them, head over to iTunes and subscribe and while
you’re there, it would be great if you could leave us a review letting us know how the show
affected you. So, thank you again for listening, and I really look forward to future conversations
together.
[Singing]
“How long till my soul gets it right?
Did any human being ever reach that kind of light?
I call on the resting soul of Galileo,
King of night-vision, King of insight.”
[End of audio 0:59:08]
[End of transcript]