Reboot Podcast #8 - How Introspection Changed My Business - With Blaine Vess and Jerry Colonna

Reboot 008 Year Introspection
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Jerry Colonna: Hey folks! This is Jerry.
Ali Schultz: And I’m Ali.
Jerry Colonna: And before we start the podcast today, we thought we’d take a minute and tell
you a little bit more about the boot camps. You know, I think as powerful as
coaching can be, I was always frustrated by the kind of limitations implicit in
even a regularly scheduled session and I always wanted to go deeper. Having
done a number of workshops in my own life and had powerful, immersive
experiences, I knew that there was a benefit to spending the time to go deep. I
also knew that there was a benefit to connecting with other people and maybe
even arguably more benefit to connecting with other people than there was in
actually going deep in the material. You know, the notion of sitting around at
8:00 o’clock at night, having had a really powerful and transformative day
with somebody and just talking about – was always really important for me.
So, I wanted to provide that kind of experience. I also wanted to have an
experience where people could both go deep on the process of learning the
specifics of the job, but really being given the opportunity for what I always
talk about is that radical self-inquiry because I’m so interested in people
learning to be human and that the process of being is so much more powerful
than the process of doing the job. So, why don’t you take a minute and tell us
what’s coming up in 2015 and what we’re looking for?
Ali Schultz: We have three events this year. We have a Winter Boot Camp, February 25th
to March 1st, the Summer Boot Camp, which is our first co-founded bootcamp
which will be in May, and our first ever Boot Camp 2.0, which we designed
for our alums which will be held in October on the two year anniversary of
our first ever boot camp.
Jerry Colonna: And I guess, in the end what we’re just going to encourage people to do is to
reach out, go to reboot.io/bootcamp and thanks for listening. I guess we’ll

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move on to the podcast now.
Welcome to the Reboot podcast. I'm Dan Putt, one of the partners here at Reboot and I could not
be more excited about this conversation. We're here to showcase the heart and soul of authentic
leadership, to inspire more open conversations around what we consider the most important part
of entrepreneurship, the emotional struggle and hopefully, we open up some hearts along the
way. We are extremely grateful that you have taken the time to be with us and look forward to
this journey ahead with you. Now, on with our conversation.
"Knowing yourself is the beginning of all wisdom" - Aristotle. Entrepreneur and CEO Blaine
Vess has an impressive story. StudyMode, the company he helped start and bootstrap from his
dorm room almost 16 years ago, now has 30 employees and sees between 60 and 90 million
visitors a month. It’s rare to find 15-year-old bootstrapped companies. It’s rare to have the same
CEO for 15 years as Blaine has been. But last year, Blaine wanted more for his company and
himself. He wanted to help push his company to the next level. To achieve this, he didn’t look
elsewhere or outside. He looked within. In this conversation, Jerry and Blaine talk about Blaine’s
year of introspection which included a stop at one of our boot camps as well as him working with
a coach and therapist which ultimately helped him to understand how and why he was holding
himself back. Perhaps Blaine and Jerry’s conversation, our first of 2015, may spark your own
year of introspection. Now enjoy the conversation.
Jerry Colonna: Hey Blaine! How are you?
Blaine Vess: I’m great! How are you Jerry?
Jerry Colonna: Good, good. It really is good to see you again, you know. We were just
joking, it’s been a few weeks since the camp, but it sort of feels like it’s been
a long time.
Blaine Vess: Yeah, yeah. It’s been an eternity.

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Jerry Colonna: Yeah.
Blaine Vess: It’s been an eternity.
Jerry Colonna: Yeah, yeah. So, I’ll be curious to hear a little bit more about your experiences
post camp as well, but –
Blaine Vess: Yeah.
Jerry Colonna: – before we get started, why don’t you tell us a little bit about the company
and yourself and then even a little bit about what it is that you want to talk
through today.
Blaine Vess: Sure. So, I’ve been running a company called StudyMode for about 15 years
since freshman year of college and we help students succeed in school by
offering them a network of websites, apps, things like cram.com which is a
flashcard website for memorizing languages, art, history, medical
terminology, whatever you are trying to learn and a number of other
properties. For the first 11 or 12 years of the business, I ran it just with a
couple of friends, my two co-founders and three years ago we decided to
reinvest in the business, really professionalize it, take it to another level. So,
it’s been a long journey, but now we’re about 30 people here in Los Angeles
and our sites reach, depending on the time of year, anywhere between 60-90
million users a month.
Jerry Colonna: Wow.
Blaine Vess: Yeah, that’s us.
Jerry Colonna: You’re smiling. I’d be proud. Are you proud?

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Blaine Vess: I am proud. I am proud.
Blaine Vess: You know, learned a lot of lessons over the years, but we made it through and
we’re still going strong. So, I’m very proud.
Jerry Colonna: It’s rare to have a company that’s been bootstrapped. It’s rare to have a CEO
stay in place for 15 years.
Blaine Vess: Yeah.
Jerry Colonna: It’s rare that a company can succeed like that, I mean, just beating the odds
seems to be a big component of what you’ve been doing which is kind of cool.
Blaine Vess: Yeah, yeah. It’s just been a lot of sticking with it and experimentation over the
years, just seeing what works and, you know, asking advice whenever I could
and having a great team at this point. So, yeah. It’s been a lot of trial and error
but we made it; we made it through.
Jerry Colonna: That’s great and I appreciate you taking the time for that. Tell me, what was
on your mind? What were you thinking about as it relates to participating in
the podcast and I’m wondering too if it has anything to do with sort of the post
boot camp experience? Right, you came to our October 2014 boot camp so tell
me what’s going on for you.
Blaine Vess: Yeah, so this year has been what I call my year of therapy and coaching.
Jerry Colonna: Mm-hmm.
Blaine Vess: So, you know, I worked – and I’ll just elaborate a little on that. I worked with

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a therapist earlier this year, to work on some of the issues that I was having at
the company just really around more of a sort of management perspective like
how do I get better at this or, just helping my team get better, helping myself
get better; just to be a better leader. Then, I met Khalid, who’s been my coach
for, I don’t know, six months now.
Jerry Colonna: That’s Khalid Halim, my partner here at Reboot.
Blaine Vess: Exactly. So that was like, another step in the right direction that’s been
extremely helpful. Luckily, a friend introduced me to him and I know it’s
helped me become a better leader, which has helped this company become
better. Then going to the boot camp, kind of topped everything off; just sort of
getting to a place where I knew that I wasn’t alone. I met some very, very
talented, smart people all facing similar or even the same issues. I learned a lot
from you and the team at Reboot as well as all my peers there. I guess one of
the biggest things for me was just being more comfortable with the idea of
taking it easy sometimes. I mentioned this to you once before, earlier this year
especially, I was walking around the office and it feels like, you know, being
on some sort of like, Speed or drugs like, just very intense and then I
remember you talking about it with Jason Calacanis’ words, "It’s adrenaline."
It is a drug and I know I was really riding that a lot and I still get that
sometimes but I’m also, at this point, more comfortable with chilling out,
leaving the office a little early sometimes, deciding to go out rather than
forcing myself to work till 1:00 AM on a Friday or something like that. So,
I’ve definitely chilled out a little bit but it’s also about sort of refocusing and
at this stage of my company, figuring out what’s next and getting some help to
take it to the next levels.
Jerry Colonna: It feels like that this itself, this whole year has been a kind of a year – I mean,
you called it a year of therapy and coaching and if there is a larger umbrella,
it’s kind of a year of introspection and self-reflection. Is that right?

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Blaine Vess: Yeah, definitely, definitely and it’s great, it’s exciting learning about yourself
because once you know that you have certain things that drive you or, in some
cases, hold you back and you can actually work on those things, it’s really
helpful. So, I’ve been working with both Khalid my coach and therapist so
like okay, great, we worked out some things like, what’s next? You know,
what else can we work out?
Blaine Vess: So –
Jerry Colonna: You know, it reminds me of this notion of a kind of conscious awareness of
what’s really going on internally; creating opportunity for choice.
Blaine Vess: Yeah.
Jerry Colonna: You know, if you remember from some of the conversations we’ve had at the
camp, some of my favorite questions were things like, well what kind of adult
do you want to be?
Blaine Vess: Yeah.
Jerry Colonna: And what kind of company do you want to run? Or what kind of company do
you want to work for; right?
Blaine Vess: Yeah.
Jerry Colonna: Because you really are creating those things. You’re creating that person by
the choices we make every day. You know, one of my Buddhist teachers gave
me an instruction last week and it’s been really powerful and what she said

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was – and then I’ll explain it, "All beings own their own karma. Our
happiness, our unhappiness is a function of our choices. Not my wishes for
them." And you know, the teaching is really about raising a level of awareness
about the fact that so much of what we, sort of think about is happening to us
is really a consequence of choices that we have made or even the choice to not
deal with something. So, you know, the case for you, it sounds like part of
what you have been dealing with in the last year, is an increasing awareness of
the things that you were either doing or not doing –
Blaine Vess: Yeah.
Jerry Colonna: – that contributed to either your happiness or unhappiness. Am I getting that
right?
Blaine Vess: Yes, definitely.
Blaine Vess: Definitely. Spot on. Once you know they’re there, now what do you do?
Blaine Vess: So, I can’t remember the quote you shared with us. I should remember. Well –
Jerry Colonna: This being so?
Blaine Vess: Yes, "This being so, so what?"
Jerry Colonna: Yeah, this being so, so what?
Blaine Vess: That’s it.

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Jerry Colonna: Right, right. Yeah and what that refers to is really, you know, recognition
without judgment, right?
Blaine Vess: Yeah.
Jerry Colonna: Which is really, really key because one of the reasons why we hide shit from
ourselves is because it doesn’t make us feel good.
Blaine Vess: Right.
Jerry Colonna: I was actually working with a client earlier today, and we were talking about
the fact that when certain questions are asked of him, he gets confused and
starts to sort of numb out.
Blaine Vess: Yeah.
Jerry Colonna: And he said, "I need a question that will cut through that." And I said, "No,
no, no, no. Let’s hang out with the thing that’s blocking you from actually
responding."
Blaine Vess: Yeah.
Jerry Colonna: What happens when someone asks you – and in this case, what makes you
happy at work? That question would cause him to freeze up and it’s because
the exploration of being happy requires him to explore what makes him
unhappy and he didn’t want to think about that.
Blaine Vess: Yeah.
Jerry Colonna: And so he’d rather just numb out.

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Blaine Vess: Right.
Jerry Colonna: And "get confused."
Blaine Vess: Right.
Jerry Colonna: And so all of a sudden, the focus becomes the problem, "I’m confused," not
the action which is, "Well wait, I’m splitting off from the experience because
the experience is painful."
Blaine Vess: Yes.
Jerry Colonna: Does this resonate with you?
Blaine Vess: It does; I think of it in a similar way, something that I worked on a lot this
year was the frame – sort of my personal framework of being cautious about
what I was saying and I used to say to myself in some cases, like I don’t want
to be around a lot of people because it exhausts me and it sounds like a very
introverted thing to say except, I’m not really an introvert. I’m in the middle
probably but what was really exhausting me was my framework of caution of
like, how to answer. You know, how to answer a question, where it’s like
running it through these rules of safety and I’ve really been able to let go of
85-90% of that and if I even sense – I was somewhere recently on it. I was on
a trip with a group of people and I sensed myself getting there, and I was like,
"What the hell – what are you doing?" Like chill out, you know, don’t let this
bullshit framework takeover the conversation. So, it’s definitely in that realm
of what you’re talking about.
Jerry Colonna: So the bullshit framework would be, sort of a kind of self-consciousness,
maybe even self-censorship.

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Blaine Vess: Yes.
Jerry Colonna: What am I going to say? How am I going to say it? How is it going to be
received? What are they going to think of me?
Blaine Vess: Yeah.
Jerry Colonna: Yeah, you’re smiling as I say all these things because those –
Blaine Vess: [Laughs]
Jerry Colonna: – those are the questions, eh?
Blaine Vess: Yeah, exactly.
Blaine Vess: Exactly. Yeah, a lot of it relates to confidence and I just, at a certain point
realized, that framework was actually limiting my confidence.
Jerry Colonna: You were so busy about trying to maintain what other’s perception of you –
Blaine Vess: Yeah.
Jerry Colonna: – in order to feel good about yourself, you ended up wasting energy and not
feeling good about yourself.
Blaine Vess: Exactly.
Jerry Colonna: Right.

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Blaine Vess: Exactly. So –
Jerry Colonna: It’s amazing how our coping strategies end up kind of putting us into a box –
Blaine Vess: Yeah. Oh, yeah.
Jerry Colonna: – that actually prevents us from getting the thing we want the most.
Blaine Vess: Yes, yes. And it’s funny because the whole reason I can even sit here and tell
you that is because I’ve gotten over it. You know, I would never have
normally said that before.
Jerry Colonna: Wow.
Blaine Vess: I’ve never talked about that before.
Jerry Colonna: Mm-hmm.
Blaine Vess: So it feels good to have let that go. It feels very good.
Jerry Colonna: Yeah, and I just noticed that your voice just softened as you said that.
Blaine Vess: Yeah.
Jerry Colonna: There’s some feeling in there; isn’t there?
Blaine Vess: Definitely.
Jerry Colonna: Yeah, yeah.

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Blaine Vess: Relief.
Jerry Colonna: It’s relief.
Blaine Vess: And happiness, yeah.
Jerry Colonna: Yeah, yeah. Who knew that not working so hard could actually generate some
relief and happiness?
Blaine Vess: [Laughs] Yeah.
Jerry Colonna: You know?
Blaine Vess: It’s true, it’s true.
Jerry Colonna: It’s like what if it – like it makes me laugh because, you know we all struggle
to launch these businesses. We all struggle to sort of have a work environment
that is rich and rewarding for ourselves and then we bring forward these
constructs that like, trap us and then we don’t get to enjoy what we’ve created.
Blaine Vess: Yeah. So, then what’s the point of creating?
Jerry Colonna: Exactly. What’s the point of creating? You know?
Blaine Vess: Yeah, yeah.
Jerry Colonna: It’s kind of nutty, eh?
Blaine Vess: [Laughs] It is.
Jerry Colonna: You know? It’s like I often joke, you know, like I look at audiences and I talk

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about entrepreneurs and in my experience, many entrepreneurs don’t come
from parents who themselves were entrepreneurs. Some do, but many don’t.
And myself, for example, I started businesses in part because I did not want to
live the life that my father lived. You know, you’ve heard me talk about this
before.
Blaine Vess: Yes.
Jerry Colonna: And so we have this image of what work is where we go off and it’s
stultifying, and it’s enervating and it’s deadening and so we say, "Okay, I’m
going to create a startup, and it’s going to be so different."
Jerry Colonna: And yet we find ourselves in exactly the same trap.
Blaine Vess: Yeah.
Jerry Colonna: And it’s a trap that we create for ourselves.
Blaine Vess: Yeah, yeah.
Jerry Colonna: Right. It’s out of the wish to be in opposition to the way we were brought up
we create this very same kinds of constricting constraints on our children and
I’ll tell you, as a parent I really relate to that because I can see, you know, I
can see the ways in which my own craziness creates stuff for my kids even
though they have these incredible skills, these speaking skills, these self-
awareness skills, they’re fantastic –
Blaine Vess: Yeah.

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Jerry Colonna: – they’re not without their stuff.
Blaine Vess: Right.
Jerry Colonna: And you know, what that says to me is, being with your stuff is an expression
of our humanity.
Blaine Vess: Yes.
Jerry Colonna: There is no group of individuals sitting out there on some island somewhere
completely perfected and free of all foibles.
Blaine Vess: Right, right.
Jerry Colonna: It just doesn’t happen.
Blaine Vess: No, no and it’s funny. I actually – you know, even with, sort of, the
realizations that I’ve had this year, you know, like everybody, I have had
realizations in the past, and you feel like, okay, we’re – I’m cured! I’m done
with this phase!
Jerry Colonna: I'm done. [Laughs]
Blaine Vess: And then life moves on, and more things need to be cured. So –
Jerry Colonna: Yeah, yeah. Well, I think that’s why the answer isn’t necessarily to find the
answer, right?
Blaine Vess: Yeah.
Jerry Colonna: It’s a – and that’s why I love that word "practice." We tend to apply it to

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things like yoga, or sitting meditation practice, you know, it’s a practice and it
just – for me it reinforces the notion that I actually never achieve the goal.
[Laughs]
Blaine Vess: Yeah.
Jerry Colonna: I’m always practicing.
Blaine Vess: Yeah.
Jerry Colonna: Right? How has this impacted, or this year of exploration, how has it impacted
your relationship with your job, the company? Talk to me about the
management practice for you. The leadership practice.
Blaine Vess: Yeah. I guess a couple of areas, I’ve realized – actually, okay, a few things.
We talked a little bit about this at boot camp and the first one is easier. It’s
about knowing what I want to do and what I don’t want to do, and then being
transparent about that with, my co-founders, my team. That felt good. Just
getting that out there, getting everybody on the same page so that really the
expectations are set. Along those lines though, I’ve also had to grow as a
manager and fortunately, I’ve got some great team members here who have
really pushed themselves and raised the bar for themselves and raised the bar
for me too. So I mean, even until – I guess, I always saw myself as a very
hands off manager, and I still am. You know, I’m not a micromanager. I think
I can say that but also getting more involved in helping people grow and along
those lines I consider myself to be a very unstructured person and I’ve always
taken pride in that. I don’t have a schedule, you know, I don’t go to bed at the
same time every night, I don’t wake up at the same time in the morning. I
work out, but I don’t work out the same days, at the same time; all that kind of
stuff and so, I’ve started adding some structure and getting comfortable with
that. You know, even around the office, simple examples like team one-on-

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ones or now we have our weekly all-hands meeting, you know, things like that
which seem minor, but getting there instead of just saying, "I don’t want to do
that," to just really stepping it up. But lastly, you know, and I talked about this
at the boot camp a bit, really my more recent – I just finished a COO President
search here, at StudyMode and that’s really important to me because I know I
can keep growing this company. I know I can. We’ve done a lot, we’ve
learned a lot and I think, you know, we’ve got an amazing team and, you
know, there’s a great foundation here and at the same time, I’m a little tired of
learning lessons.
Jerry Colonna: [Laughs]
Blaine Vess: You know, the lessons that other people already have learned.
Jerry Colonna: On other people’s money. [Laughter]
Blaine Vess: Yeah, yeah, yeah. Totally because, you know, what I didn’t mention before is,
you know, we’re bootstrapped – actually you mentioned that, we don’t have a
board, we don’t have any sort of, formal advisory group, anything like that.
So, I’m really excited to have someone coming in, who’s going to help get the
organization in even better shape and I’m going to learn. I’m going to
continue to learn and I’m going to get better as a leader too. So, that’s been a
big focus for me since boot camp actually.
Jerry Colonna: Well, I want to congratulate you on that. I mean, I think the allowing another
experienced individual to come in and take responsibility for this thing which
you, quite frankly, you know, we often joke about our companies being our
babies, but you were a baby when you started this company. You know?

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Jerry Colonna: And so you know, this has been part and parcel of you for a long, long time to
be able to do that. I’m curious if this year-long journey of self-exploration,
what if any impact did it have on the decision even just to open up a President
COO search?
Blaine Vess: Yeah, it definitely had an impact. I mean, I’d like to say that I’m pretty
humble, I’m always willing to learn, I’d rather focus on things I don’t know
than things I do know, and it definitely had an impact, and it’s kind of nice to
be closing out the year with this change because yeah, there has been a lot of
self-reflection on. It’s been 15 years, what’s next? You know, what’s next?
Fortunately, I’m still very passionate about this company and I love my team.
I love coming to work every day. So I’ve still got that, which is awesome and
I only think I have that because we haven’t been afraid of change. I couldn’t
be running the same company I was running five years ago but so much has
changed. I’ve learned a lot and we’re still following that track. But now yeah,
for me it’s like, let’s accelerate the intelligence coming in here, our own
capabilities, what we’re getting done, yeah and I guess it’s that constant CEO
internal battle of am I doing the right things? Am I managing correctly? You
know, all those things. I’m not afraid to admit that I could use some help and
this year’s helped me realize that more than ever and sort of, become more
comfortable with it.
Jerry Colonna: Mm-hmm. You know, and this is a little bit un-coach like of me, but I’m
going to offer it anyway.
Blaine Vess: Okay.
Jerry Colonna: Would you like my view, as to whether or not you’re doing the right thing?
Blaine Vess: I’d love it.

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Jerry Colonna: Okay. So, here’s one way to think about it. How are the outcomes? How’s the
business doing?
Blaine Vess: It’s doing really well.
Jerry Colonna: And the person that – have you actually negotiated and recruited this COO
President?
Blaine Vess: We have an informal agreement now.
Jerry Colonna: Okay.
Blaine Vess: Yeah.
Jerry Colonna: Now, is this person a good person?
Blaine Vess: Yes.
Jerry Colonna: So, here’s something that my therapist used to say to me all the time that I’m
going to give to you.
Blaine Vess: Okay.
Jerry Colonna: Okay? There’s a right way, and there’s a wrong way and there’s the way that
works. Okay?
Blaine Vess: Yeah.
Jerry Colonna: And if you really want to understand if you’re doing the right thing, look at
the outcomes. Okay?

Page 19 of 21
Blaine Vess: Yeah.
Jerry Colonna: You’re smiling ear to ear. You feel good inside. You’re making good
decisions. You leaned into some very vulnerable and difficult places and the
result was, you learned even more.
Blaine Vess: Yeah.
Jerry Colonna: You let go, you allowed some changes and some good things are happening. It
seems to me that it’s the right thing. It feels to me Blaine, you know, things
are going pretty well and you can enjoy that.
Blaine Vess: Yeah, yeah. I’ve gotten better at enjoying it.
Blaine Vess: A lot better.
Jerry Colonna: Yeah. You take it in and create a culture where more of that can flourish, you
know?
Blaine Vess: Yes.
Jerry Colonna: So, we’re going to start to wrap, but if there’s any one thing that perhaps, sort
of sits with you from this last year of exploration for you, what would you say
it is? And speak to the Blaine of five or six years ago, if you know what I
mean.
Blaine Vess: Okay. I would say there’s a theme of not being afraid to ask for help; whether
that’s through therapy or coaching or me now getting help from someone who
has got a lot of experience in the business. That’s my biggest lesson this year

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because that’s, you know, mainly the – like I said, the therapy and coaching
were so helpful, and actually it wasn’t even until boot camp that I’d feel
comfortable saying that I had a therapist. So, you know, it’s been quite a
change, but a change for the good.
Jerry Colonna: That’s a brilliant piece of advice. So I’m going to give you just a response to
that and as I heard you sharing your story, one of the things that occurred to
me was to be grateful to you because whether you realize it or not, you’re now
helping another entrepreneur by sharing your story.
Blaine Vess: That’s great. I’m happy to.
Jerry Colonna: Right. I mean, think of the permission that you’ve just given another
entrepreneur to ask for help.
Blaine Vess: Yes.
Jerry Colonna: Right?
Blaine Vess: Yeah.
Jerry Colonna: And you know, you’ve heard me say this before, there are not enough coaches
and therapists in the world. There are not enough leadership coaches in
management –
Blaine Vess: Yeah.
Jerry Colonna: We’ve got to help each other.
Blaine Vess: Yeah.

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Jerry Colonna: And my friend, you’re embodying that just even by sharing your story like
this. So, I really want to thank you for that.
Blaine Vess: Well, thank you and thanks for the opportunity to be here.
Jerry Colonna: Oh, it’s my pleasure and you better come to the alumni boot camp.
Blaine Vess: I will. [Laughs] I’m there.
Jerry Colonna: I’ll kick your ass if you don’t.
Blaine Vess: [Laughs] All right, I’ll be there.
So 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 would 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 transcript 0:34:25]

Reboot Podcast #8 - How Introspection Changed My Business - With Blaine Vess and Jerry Colonna

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