How can you save a business from the brink of bankruptcy and grow it 2,000% in 10 years, and yet feel like it could all go away in any given moment? Or face the fear, the weight, that you must be chief breadwinner...for you, your family, your co-founder and team’s family as well? Fear is pervasive in our lives, and in the crazy world of startups and entrepreneurship it is an always present participant. In this episode, we have two entrepreneurs dealing with two different and yet similar fears, fears that entrepreneurs will know all too well.

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Welcome to the Reboot podcast. I'm Dan Putt, one of the partners here at Reboot. I could not be
more excited about this show. I've known Jerry for almost seven years now, and without a doubt,
could say that my work with him has had a profound impact on my life. In this show, we're
opening up the coaching couch to the world and bringing everyone in on this conversation
around this work. We're here to showcase the heart and soul of authentic leadership and to
inspire more open conversations around what we consider the most important part of
entrepreneurship - the emotional struggle and hopefully opening 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 to our conversation.
Before we kick off our show, I wanted to quickly mention, we will be officially announcing our
boot camp schedule for 2015 very soon. So, be sure to check out our website, REBOOT.IO or
sign-up for our email newsletter and be the first to find out when applications officially open.
"We come to accept that everyone of us can fail. Fail to live the life we desire for ourselves or
even fail to uncover the desire itself. Without failure we have no possibility of appreciating or
praising the life well lived, the work well done, a place well taken care of or the greater ecology
that makes up our home." That’s from David Whyte, in his book "The Heart Aroused: Poetry
and the Preservation of the Soul in Corporate America". How can you save a business from the
brink of bankruptcy and grow it 2,000% in 10 years and yet, feel like it all could go away at any
given moment or face the fear, the weight, that you must be chief breadwinner, for you, your
family, your co-founder, your co-founder’s family?
In this episode we have two entrepreneurs dealing with two different and yet similar fears, fears
that entrepreneurs know all too well. Our first conversation is with Sherman Lee, co-founder and
CEO of Good Audience.
One quick note: You’ll hear some dates mentioned in this episode and I just wanted to mention,
it was recorded at the end of August.
Sherman Lee: So, Good Audience is a SAS that allows you to build, manage, and market your
social communities in essentially a fraction of the time. So it’s like inbound
marketing on social media and we just did Techstars, London and we moved
back to San Francisco about a month or so ago.
Jerry Colonna: And tell me a little bit about the financing history because I know that your core
questions are about financing. Did you bootstrap into Techstars and then get a
little bit of money? Where are you?
Sherman Lee: Right, so, we only have the money from Techstars and during Techstars we had
completely shut down the previous business and pivoted it into something new
and we launched our beta about nine weeks ago. We have almost 1,000 users
now and about two percent are paying and so we have about $850 in monthly,
recurring revenue so far.

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Jerry Colonna: Okay. Why don’t you give me a little bit more on what your core questions is
and what it is that you want to talk through too about today?
Sherman Lee: Yeah, so my biggest concern is running out of money. [Laughs] So we’re going
to run out of money somewhere near the end of the year and it’s just like the
biggest struggle for us is figuring out how to get people into our product, get
them to actually like it and get them to pay and it’s not as fast as we’d like.
Jerry Colonna: Okay, so you ready to do a little bit of real coaching?
Sherman Lee: Sure!
Jerry Colonna: Okay. I promise you that we will talk about fundraising strategy. Okay?
Sherman Lee: Mm-hmm.
Jerry Colonna: But I want to bring you back to something and I noticed it immediately when
you started talking about running out of money. Can you tell me again what the
fear is? You’re going to run out of money?
Sherman Lee: Uh, running out of money would mean that I can’t pay my co-founder. He has a
wife. I also have a wife and a baby, so uh, everyone needs to be fed [Laughs]
essentially and so that’s the biggest fear of not having money.
Jerry Colonna: So, slow down and feel that. [Pause] Now do you feel it? So here’s what I
noticed, okay, and this is true for a lot of people. They start to talk about the
thing that’s really, really scary and they speed up. It’s like running past the
graveyard because it’s so scary we want to not actually stay there.
Sherman Lee: [Laughs] True.
Jerry Colonna: And I’m a pain in the ass because I’m gonna make you stay there for a few
minutes. What’s your wife’s name and what’s your baby’s name?
Sherman Lee: My wife is Shannon and my daughter is Fiona.
Jerry Colonna: And how old is Fiona?
Sherman Lee: She is three months and five days.
Jerry Colonna: Okay. Three months and five days, so this is really visceral.
Sherman Lee: Yeah.
Jerry Colonna: So, I have three kids and I will tell you something I’ve shared with a lot of
people. I heard this many years ago, "Being a parent is like wearing your heart

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outside your body." That’s how vulnerable and scary it is. What is the crazy,
implausible fear, the one that your mind keeps trying to push out of your head
when you think about running out of money and Shannon and Fiona and your
co-founder and his wife and probably, do they have kids?
Sherman Lee: They do not have kids yet.
Jerry Colonna: Yet! Yet! I knew the yet. The kids to be named later; when they come to your
mind, what happens?
Sherman Lee: Uh, I do not want to disappoint them.
Jerry Colonna: Why not?
Sherman Lee: I feel like I have a responsibility as co-founder of this company to continue to –
like on a monthly basis, to get everyone fed.
Jerry Colonna: To get everyone fed. So, this is very raw. This is very primal. Your job, now are
you feeling the visceralness of "breadwinner"? You know, we use this term
blithely in society, we toss it around. "Well he’s the breadwinner, she’s taking
care –" or "She’s the breadwinner –" but that feeling that you have right now
which is, "Holy shit! I have my wife, my daughter, my co-founder, his wife, and
their future children to feed." Forget about you!
Sherman Lee: Yeah, I didn’t think about me! [Laughs]
Jerry Colonna: Of course you didn’t think about you because you’re the breadwinner, because
you’re the one who has taken upon yourself – and I’m not saying it’s not true,
but notice the emotional content that’s associated with this. I’ll explain to you
why it’s important to notice the content in a second but I want you to hold on to
this. Notice what happens in your body. Notice how like, again, our audience is
not going to see your face but you went from that kind of nervous smiling,
which is very sweet, to a more serious, like somber because it’s a landing. The
reason why it’s important is that in order to be able to rise above the fear, you
have to actually become familiar with it. You have to actually understand it.
You have to actually lay out the stakes.
Sherman Lee: Mm-hmm.
Jerry Colonna: Now why is that important? Because there’s another part of your brain, the
planning, strategic part of your brain, the part of your brain that’s creative and
innovative, the part of your brain that said, "You know what would be really
cool? What would be really cool is if we can automate the way people market to
their social media." Right? That breakthrough thinking, that part of the brain
dials down when the other part of the brain dials up.

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Sherman Lee: Uh-huh.
Jerry Colonna: And this is counterintuitive but the most important strategy for your fundraising
for the next four months, because by the way you’ve got to get this done in the
next four months; right?
Sherman Lee: Mm-hmm.
Jerry Colonna: Is going to be to manage down your fear because if you go into the fundraising
terrified that Fiona is not going to be fed, it’s going to undermine your ability to
fundraise. Do you see what I’m saying?
Sherman Lee: Uh-huh.
Jerry Colonna: The key to fundraising is to get people excited about your vision. I love
investors. They’re my friends. Some of my best friends are VCs but if you go
into this process terrified, then it becomes a self-fulfilling prophecy. And if you
go into this process bullshitting yourself and pretending that you’re not afraid
that you’re going to fail to feed your baby, then you’ll come across as a liar, a
sham artist. So, my wish is for you to come across as the authentic, confident,
creative, innovative, entrepreneur that you are and what I want to do is give you
the tool to understand that fear –
Sherman Lee: Okay.
Jerry Colonna: – so that you’re familiar with it? Now watch, let’s imagine that the company
does run out of money. Imagine the company runs out of money tomorrow!
Okay. What will you and Shannon do to feed Fiona?
Sherman Lee: Um, there’s always credit cards.
Jerry Colonna: Credit cards; anything else?
Sherman Lee: I have some stock. Uh, we could sell our home.
Jerry Colonna: How about getting another job?
Sherman Lee: Huh! I didn’t think about – [Laughter]
Jerry Colonna: My point is this, when you’re a person who’s living with your heart outside
your body, i.e. a parent, you’ll do whatever it takes; won't you?
Sherman Lee: Yes.
Jerry Colonna: If you have to fucking paint houses, you’ll paint houses. Fiona will be fed. You
may not be, but you will. Am I wrong?

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Sherman Lee: No.
Jerry Colonna: Okay. So, don’t worry about Fiona. I’m not saying you couldn't get yourself
into a physical, emotional state where you couldn't work or you couldn’t, you
know, dig ditches but if that’s what you had to do, then that’s what you’ll do.
And if that’s what your co-founder has to do in order to feed his yet to be named
kids, then that’s what he’ll do.
Sherman Lee: Right.
Jerry Colonna: So all we’re talking about right now is creating the conditions in which this
dream you have can actually come to fruition, which is that this company gets
the requisite funding just to get to the next level, not even to break free of
gravity, just get to the next level. Now what I’m doing here with you in this
very short amount of time is helping you, hopefully, helping you connect in a
grounded way to the reality –
Sherman Lee: Right.
Jerry Colonna: – which is often times what gets lost in the terror of fundraising because it’s a
terrifying process. Now, let’s shift gears and let’s talk pragmatic. Tell me what
your fundraising strategy is going to be.
Sherman Lee: So we moved from London back here so we don’t know anyone but we’re
connecting with all the Techstars companies that are in the area and just asking
for advice and in doing that, they learn about our business and they help us
figure out, like, how we do our pricing and they introduce us to more people and
I guess, hopefully with all these connections, someone will know the right
investors who are in our space. And so, I’m essentially going across AngelList
and LinkedIn and finding all the Angels who have invested in the social media
space or inbound marketing space, building a list and I’m going to share it with
them and hopefully have help.
Jerry Colonna: And hopefully what?
Sherman Lee: Have help. [Laughs]
Jerry Colonna: Okay. So, uh, I’m going to give you a B-minus for that strategy, okay? I’m
going to take it up a level, okay? First and foremost, well first tell me how much
are you looking to raise?
Nigel Sharp: $400,000 to help us integrate other social media services. So we want to hire a
couple of engineers and we also need to bump up our sales and marketing.
Jerry Colonna: All right, how long will $400,000 last you?

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Sherman Lee: Uh, about 18 months.
Jerry Colonna: From when you close the investment?
Sherman Lee: Yeah.
Jerry Colonna: Okay and when will you be dead, dead, dead out of cash according to the
current burn?
Sherman Lee: Uh, December.
Jerry Colonna: December 31 or December 1?
Sherman Lee: Uh, like as it gets closer, I think we can cut off our expenses to last till
December 31.
Jerry Colonna: Okay, so you need to have actually – and you’re probably going to have to do
this in a rolling close because you’re not going to – I don’t think you’re going to
be able to raise $400,000; let’s see, it’s August 15th – okay, we’re launching a
military campaign today. Today! Okay? You want a spreadsheet, you want like
a Sales Force-like document. Okay and this is your assignment; I want you
meeting with, meeting with, and I’ll define that in a second, four to five people
per week.
Sherman Lee: Okay.
Jerry Colonna: And by meeting, I mean, talking on the phone or actually genuinely meeting
with them. You may not be asking them for money, but what you’re asking
them for, sometimes you may be asking for money, but what you’re asking for
is at least another meeting with them or someone else that they can be meeting
with. So, your Techstars contacts, your mentors from Techstars and other
friends that you have in the business. Which means, next week, your pitch
documents have to be ready, okay?
Sherman Lee: Okay.
Jerry Colonna: Any fear coming up for you, as I say this?
Sherman Lee: Um, there’s always the fear of the pitch documents not being –
Jerry Colonna: Good enough.
Sherman Lee: Good enough. Yeah.

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Jerry Colonna: Okay. What about a fear of cold calling or reaching out to someone that you
haven't ever met before?
Sherman Lee: No, I –
Jerry Colonna: Good!
Sherman Lee: – do that all the time.
Jerry Colonna: Good! That’s your best asset. That’s your best asset. You got to sell that. You
got to build on that. Four to five of these meetings per week, which means a shit
load of emails. You want to start thinking about the structure of this investment
because the likely scenario is that you’re not going to get $400,000 from one
investor.
Sherman Lee: Uh huh.
Jerry Colonna: The likely scenario is you’re going herd a bunch of cats, okay? And it’s going to
be difficult because you're going to get $10,000 from this person and $50,000
from this person and this person’s going to be on vacation and they said they
were going to get back to you and so you want to set up the investments such
that the money can start coming in. Your goal, I’m going to give you a hard
goal, I want this company funded by November 15th. You see what I just did?
Sherman Lee: Uh huh.
Jerry Colonna: I scared the crap of you because what you don’t want to do is run out of money
just as you’re closing your documents.
Sherman Lee: Okay.
Jerry Colonna: I mean you could but you see the point I’m trying to make.
Sherman Lee: Right.
Jerry Colonna: Are you the CEO?
Sherman Lee: Yeah.
Jerry Colonna: Okay this is your job. Okay? It’s not about selling the vision of the company,
per se, it’s not about necessarily sales. You have to get the resources in the bank
and you only have – right now everyone’s on vacation so that’s good. So you’re
not going to get a lot of responses, so you want to work on those pitch
documents as much as possible. You want to get the story down clean and sharp
and crisp. You want to get your demo down clean and sharp and crisp. And you
are fundraising. September 1, you are hitting the ground and you are running. I

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want you to tell Shannon that we've had this conversation. I want you to take
her out to dinner to tonight and tell her that September 1, you’re not going to be
around a lot.
Sherman Lee: Uh huh.
Jerry Colonna: Or even if you’re around, you’re going to be preoccupied so apologize in
advance.
Sherman Lee: Okay.
Jerry Colonna: You see what I’m saying?
Sherman Lee: Yeah.
Jerry Colonna: Because I know the last three months has been this extraordinary experience.
You’ve got this baby and you’re dealing with it and it’s exciting and in the back
of your mind you’re worrying about running out of money. So you’re going to
be focused, September and October, that’s your time and again, I want you to
think about this as a military campaign. It’s a disciplined – everyday, "Who
have I talked to?" What’s your co-founder’s name?
Sherman Lee: Carl.
Jerry Colonna: I want you to explain this to Carl because he won't have listened to this by the
time you’re – or this will be broadcast after September 1.
Sherman Lee: Uh huh.
Jerry Colonna: So, I want you to explain to him what I’m saying to you but you have to be
focused on getting this done. This is job one for you.
Sherman Lee: Uh huh.
Jerry Colonna: Okay?
Sherman Lee: Uh huh.
Jerry Colonna: You want to be focused on the lead who’s going to set the terms. I want to test
something. What valuation are you looking for?
Sherman Lee: Um, I think we want to be at market rate. Uh, we don't have the valuations set
yet but I –
Jerry Colonna: Beautiful! It was a test because any number you gave me would have been
wrong.

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Sherman Lee: Oh, we learned that from David Cohen! [Laughs]
Jerry Colonna: Perfect! So here’s the message, I will reinforce the David Cohen from
Techstar’s message here. We are not – here’s the magic ninja move, we are not
going to let valuations stand in our way from getting a great financial partner.
Isn’t that nice? [Laughs] We are not going to let valuations stand in the way
from us actually raising this money. The message that you want to send out and
the posture you want to take is, we are smart, reasonable, thoughtful investors.
There’s plenty of time, if you get multiple term sheets and you know, $600,000
worth of – great, then you negotiate and no, don't give away the whole company
but don’t worry so much about that, right? You stay focused. Your job is to
convey to the investors that the idea behind the company may shift again but
you’re a good entrepreneur because at this stage, the whole business will shift
again in a year. We don’t know. Is this helping?
Sherman Lee: Yeah, definitely.
Jerry Colonna: Okay so I wanna bring to your attention; two pieces here we dealt with. The
emotional piece of this, the fear because often times the fear actually prevents
us from seeing clearly and then notice how quickly we’re just able to lay out a
clear plan of attack because you know what we did? We just cleared out the
emotion. Okay, this is what’s going on. If I have to, I’ll fuckin’ dig ditches.
Sherman Lee: [Laughs]
Jerry Colonna: All right, now let’s get to work and build a company! You see the relationship
there?
Sherman Lee: Yeah.
Jerry Colonna: When you find yourself, and you will, you’ll find yourself with people not
responding to your emails, saying 'no', worse than even saying no, is sort of
saying 'maybe' and not giving you a clear answer and stringing you along. When
you find yourself in that place, take a deep breath, go back to "If I have to, I’ll
dig ditches". Fiona will be fine, Shannon will be fine, Carl will be fine, Carl’s
wife will be fine, Carl’s kids will be fine, everybody will be fine. Now you get
back to work.
Sherman Lee: All right.
Jerry Colonna: I want to give you another image to hold on to because this always motivates
me. Fiona’s watching you, even now. What kind of adult do you want her to be?
That’s who you are to be today. So, 30 years from now when she’s an
entrepreneur building her company, or 20 years from now, when she's an
entrepreneur building her company, she stays centered. She doesn't let fear drive

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her. She takes the fear in, she doesn't let fear drive her and she goes and does
the things she needs to do.
Sherman Lee: Right.
Jerry Colonna: Just the way you were going to do. Does this resonate?
Sherman Lee: Yeah.
Jerry Colonna: Again, I wish people could see the before and after of your face.
Sherman Lee: [Laughs]
Jerry Colonna: Tell me how you’re feeling as we starting to wrap.
Sherman Lee: Um, I feel a lot less stressed about it because I think you’re right, I mean, if let’s
say the company fails, everyone’s going to be safe, I mean and –
Jerry Colonna: That’s it! Everyone is safe. I call this a myth-making machine (he points to his
head), it’s a myth making machine! The myth is, "I’m going to fail as a father."
Okay? Love her and you won’t fail. And you already love her, you already do.
So, there’s no failing. There’s experiments that don't turn out the way you
anticipate them to do. That’s it. You love Fiona, you take care of your family
and then you experiment. Can you do those things?
Sherman Lee: Yeah. That’s not a problem.
Jerry Colonna: Say that again!
Sherman Lee: That is not a problem!
Jerry Colonna: There you go! [Laughs] Well, how was this for you? How was this
conversation?
Sherman Lee: It was good I mean, like a lot of these things, like I feel like I’m just holding in
because like, I can’t exactly share my fears because it will scare them as well.
Jerry Colonna: [Laughs] That is another myth. That’s another myth. Okay, here’s a little bonus;
when you take Shannon out tonight for dinner or when you invite food in
because you have a three-month old and going out to dinner has gone by the
wayside, I understand.
Sherman Lee: [Laughs] Yeah.
Jerry Colonna: Or when you make her dinner and you take care of her tell her about this
conversation.

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Sherman Lee: Mm-hmm.
Jerry Colonna: Tell her that you’re afraid that you won’t feed everybody.
Sherman Lee: Mm-hmm.
Jerry Colonna: And then send me an e-mail and tell me what she says. I guarantee you, I
guarantee you, she won’t say to you, "Well, Sherman! You damn well better
feed us!"
Sherman Lee: [Laughs]
Jerry Colonna: And I’ve never met Shannon, right?
Sherman Lee: Right.
Jerry Colonna: But that’s not what she’s going to say. She might say, "I have a fear that this
will happen –" or "Yes, I get worried about –" but fear, like any other feeling, is
a currency with which we connect with other people.
Sherman Lee: Mm-hmm.
Jerry Colonna: This is what being human is about. When you really want to lead well, lead with
feeling.
Sherman Lee: Okay.
Jerry Colonna: Okay?
Sherman Lee: Thank you so much! That was awesome!
Jerry Colonna: Let me thank you because it took some courage to come on the phone and meet
a stranger and talk like this and I really appreciate your being able to do that.
It’s really an honor to share this with you.
Sherman Lee: Thank you, I appreciate that.
Our next conversation is with Joseph Bassett, CEO of Dawn Equipment.
Joseph Bassett: Dawn Equipment is a company that makes the most advanced, ground-engaging
devices for farmers in the world. So we make devices that inject fertilizer into
the ground, aid in the process of injecting seed into the ground for planting and

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a number of other purposes and we’ve recently pivoted into eco and bio farming
too; and so it’s been a very good business.
Jerry Colonna: And if I remember correctly, it was bootstrapped; is that correct?
Joe Bassett: Yeah.
Jerry Colonna: Yeah.
Joe Bassett: Well, I had no choice but to bootstrap. Some people bootstrap by choice. I
basically graduated college in 2003 and had like, you know, Dawn Equipment
was actually founded by my father and some other guys and they did some
really visionary early work in precision farming, like the first yield monitor was
invented at Dawn. We really – my father as an entrepreneur, in a lot of ways,
they had this very, kind of, up into the right trajectory and then they started
thinking they were Gods and we’re going to make a complete planter instead of
just a sub-assembly and, you know, it totally – just bad execution. It drove the
company into bankruptcy and that was in my, you know, graduating high
school, going to college, really kind of traumatic time at a formative time and
seeing that experience and how that impacted my parents and so on and so forth.
I don't know, I mean I came back to a company that had shrunk down to four
employees and – who I pretty much ended up terminating all of in the first two
years.
Jerry Colonna: So it sounds like from inheriting the business out of bankruptcy, you've built the
business now, fairly substantially.
Joe Bassett: 2,000% in 10 years.
Jerry Colonna: 2,000% percent in 10 years?
Joe Bassett: Yeah.
Jerry Colonna: So, I know from my notes that you’re calling about this low-level fear, I think
you called it.
Joe Bassett: Yeah.
Jerry Colonna: Talk to me about that. Talk to me about what the concern is. What did you want
to talk through today?
Joe Bassett: Well, I mean, I think when you can connect that back to bootstrapping also,
bootstrapping is amazing if you can pull it off but like I said, I never had any
opportunity to do anything other than bootstrap and so, you’re always one click
away in those early phases when you have business that is really a struggling
business. You’re always one click away from failure and then to have to do

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relatively capital-intensive R&D and tooling and the type of products we make,
it’s very, very, very challenging and it just – I don’t know. You get into this
thing where, we hit on it at CEO boot camp, where you experience this low-
level fear that you’re going out of business at any moment, even when it’s
irrational.
Jerry Colonna: Even when you’re successful.
Joe Bassett: Even when you’re successful; yeah.
Jerry Colonna: Yeah, so let’s just pause on that one because I think that’s a really important
point. What can happen over time is it almost becomes a habit of mind. Fear
becomes a habit of mind. Sometimes it’s negative and sometimes it’s positive
but it becomes a habit and so over time, I mean, think about what you’ve just
described. You’ve been bootstrapping this. I think you said it quite eloquently,
there’s um, you’re one step away from failure all the time and you have a little
bit of what I would call, you know, vicarious post-traumatic stress disorder. You
didn't oversee a bankruptcy but you were a part of it or not even a full
bankruptcy but [Unclear 0:31:10] and so there’s that in the background at a
very young age. And so it makes sense to me that you never quite feel like
you've got the ground beneath you.
Joe Bassett: Yeah.
Jerry Colonna: And I remember another question you had in your notes was, "Or is this just
fundamentally part of who I am and do I use it to drive myself?"
Joe Basset: I mean, unraveling that ball of yarn is a complex one because, you know – and I
don’t know that you necessarily can unravel them at some point. I’ve been
extremely competitive my entire life, from when I was two or three years old, I
mean and, how some people just are very competitive people. So that part of
me, that has, I’ve always been that way. I’ve always just kind of, driven myself
in that way to where you just know things can be done better.
Jerry Colonna: So, notice something, because again, I think you’re really eloquent about the
way you’re connecting these things. I think what you’re identifying is that
there’s a connection between fear, between being driven or ambitious or
competitive, between wanting to succeed from a positive place and wanting to
succeed because not wanting to fail. Right? So it’s like it’s all interconnected
and so, you know, a lot of times people think that whether it’s through coaching
or doing some inner-work or as you recall from the bootcamp, you know this
phrase I like to use, "radical self-inquiry". A lot of times people think that the
point is to get rid of feelings, to get rid of in this case say, the low-level fear. I
don't understand. I’m successful. What am I afraid of? I would argue that it’s
not so much getting rid of a feeling. It’s really becoming so friendly with it, so
familiar with it, to understand it. So rather than it being a driver in the way that

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it drives you crazy but to use it as a tool for yourself, which I think
unconsciously you’ve hit upon since, as you said, two-years old. You know, it’s
so easy when there’s pain to assume that there’s something wrong.
Joseph Bassett: Yeah, and I mean, that’s the whole thing, it’s like, I love building farm
equipment. I've built awesome, computer-controlled hydraulic machines out of
forgings and stuff and you know, I really like doing it actually –
Jerry Colonna: I wish everybody could see your face right now because you’re smiling in a way
that’s just wonderful…
Joseph Bassett: No, it's fun, I like it! I mean, you know…
Jerry Colonna: Yeah!
Joseph Bassett: But when you have a lot of customers, when you're running – see the thing for
me is, at some point the question is, am I going to run a big business, right? And
running a big business and running a smaller/medium size business are two
totally different things and like I said, I…
Jerry Colonna: And running a business that’s succeeding and running a business that’s close to
failing are also different things. So there’s an implicit question behind all that
Joe. Right? And the question is, "What is going to happen to me?" And you
know what the answer is? I don’t know. And neither do you.
Joseph Bassett: Yeah, I’ve – I mean, lately I’ve kind of almost been feeling like, I’ve gotten
myself into, I mean, we’ve actually sorted out some very hard mechanical
problems and to have some really great designs and intellectual property and it’s
just, I’m really having to ask, what is it do I want to do; you know I – you
know, I’ve come to grips with the fact that I believe in design and products and
that in some businesses that’s everything. So these guys that come in and are
like, "Oh Joe, you haven’t gone to business school. You haven't done this, blah-
blah-blah, you don’t know how to run a business." It’s like making products that
these customers love is, these are farmers and that’s another thing, you have like
these tech CEOs that get all this buzz and everything but it’s like I run a
business that is – my available customers are like one-half of one percent of
Americans. You know, but they have such a disproportionate impact on this
whole thing and it’s – I just feel like, agriculture is really is not well understood,
in general…
Jerry Colonna: I want to interrupt you and take you back to something for a moment. You said
these people come and say, "Joe, you didn’t go to business school." Are these
real people or are these people in your head?
Joseph Bassett: No, they're real people.

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Jerry Colonna: Who comes in and says that?
Joseph Bassett: Lots of people that – the kind of people that are on the sidelines. You know?
Jerry Colonna: Okay, I want you to do something for me okay? Tell me which college degree
Bill Gates has. Oh right! None! Tell me which business school Steve Jobs went
to. Oh right! None! Notice something Joe. There’s another thread here behind
the fear and the competitiveness and the ambition and the desire to grow and the
difficulty you have about uncertainty. The way you’re allowing other people’s
projections of what status is or what success is to impact whether or not you’re
having a good time.
Joseph Bassett: Or what management is too.
Jerry Colonna: Or what management is, or what success is. Let me ask you something, you said
to me, "I don’t know if this is going to be a big company or a small to medium
sized company." What do you want Joe?
Joseph Bassett: I would like to get into some more expensive R&D projects which are the types
of things that just take – I’m not going to be able to fund out of just cash flow
but when I hear, like, when I think about growing a business, maybe taking out
an investment, maybe having a board, you just hear about like, "Oh, are you
making your quarterly numbers? Are you doing this? Are you doing that?" And
I just don't think you can run a business…
Jerry Colonna: Whoa, stay with that for a moment because I think you’re on to something here.
So, you’re imagining, in that moment you’re imagining, I recapitalize the
business or I capitalize the business in a different way. I have a board of
directors, I have all these investors, now I have to answer questions about how I
manage. Notice how you feel as you imagine that. How do you feel about
yourself? Because the feeling I got was you were almost being defensive even
before the critics were in the room telling you, "Hey listen, your quarterly
numbers aren't good."
Joseph Bassett: Yeah. Finding the right investors are going to being huge, that understand the
vision and understand the business and that’s…
Jerry Colonna: I agree, and finding the right investors who understand your inherent, natural
leadership capabilities, despite not having gone to business school and this is
important. You were asking a very powerful question. I want to take you back
to that question. So the low-level fear remains despite the fact that I’ve had
success.
Joseph Bassett: Yeah.

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Jerry Colonna: And I’m going to argue that there’s a couple of reasons why; one is, you
habitually use it to drive for further success.
Joseph Bassett: Yeah.
Jerry Colonna: That’s not a negative. Just recognize and label what it is. So that it doesn’t drive
you kind of crazy.
Joseph Bassett: We’re almost brought up in a society being told these days, that more is bad,
you know? That like…
Jerry Colonna: Joe, from where I sit, more isn’t better. More isn’t worse. Less isn’t better. Less
isn’t worse. It’s not more or less that’s the problem. It’s how you feel about
more or less. You know, I often think of that quote from the Bible, which is,
"Money is the root of all evil." It’s actually – that’s misunderstood, that’s
misquoted. What St. Paul actually wrote is, "Love of money is the root of all
evil." And what he was getting at is the way we attach a sense of self and
meaning and attach it to money. In this case, I don’t care if you want to pursue
more but if you only want to pursue more so that you can quiet some demon in
your head that tells you that less is bad or vice versa, right, as the dropouts are
telling you, either party is – the dog remains tied to the leash. Whether you…
Joseph Bassett: See, I really love inventing products–
Jerry Colonna: Then invent products.
Joseph Bassett: What I really love is inventing products but then the success is how you – is the
metric by which you get to continue to do this. You know?
Jerry Colonna: Is it?
Joseph Bassett: Yeah! I got to sell stuff!
Jerry Colonna: You got to sell stuff? So, when I asked you before, "What do you want to do?"
you hit upon something very powerful. You said, "I want to do more and more
interesting –" I think you used the word 'expensive' but you meant, 'costly'
R&D. So, really at the root of this Joe is you want to invent stuff and you want
to create a company that wants to invent stuff –
Joseph Bassett: Yes.
Jerry Colonna: – and you want to create a company that invents stuff that changes the world of
agriculture.
Joseph Bassett: Sometimes you got to lose money to make money also.

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Jerry Colonna: And that is true! You also recognize that creating a good container of a well-run
company actually furthers this and so you’re in this tension point between
investing in the business, taking the risks associated with that and doing it. I
have no problem with it and I don't think you will have a problem with that but I
think now we’re talking about stuff that is in the realm that actually can feed the
fear and the fear, if you think about it, let’s go back to the fear for a moment.
The fear – you said that you were worried about failing and then you realized
that it’s not actually failure. It’s this low-level constant fear. Do you know what
it is that you’re afraid of? What’s the most outrageous, crazy, fear that comes to
mind when you think about it?
Joseph Bassett: Oh yeah. I mean, the worst thing that it’s gonna do, and I mean, I’m not going
to, I mean, if I "failed" well, I’m not going to end up on the street; I mean, I can
find another place …
Jerry Colonna: What is the fear? I understand that your conscious mind is telling you, don’t
worry about it but what is it that you’re actually – that that scared little kid is
worried about?
Joseph Bassett: That’s that aspect to family business that I think a lot of people don’t really
understand in that same way that when you start mixing families and business
together and all – so you take the issues that exist inside of relationships, inside
of families, then you kind of mobilize them inside of a business and I mean,
we’re – 45 people work at Dawn Equipment. It's not – I mean it still has been a
family business and …
Jerry Colonna: So your fear is that you’re going to, what, fail the family and the family legacy?
That makes total sense! So, can you see that by holding on to – that’s like when
St. Paul said, "Love of money is the root of all evil." You’ve got this false
conflict that you're working with, which is, I’d like to take risks, I’d like to
expand the platform, I’d like to capitalize the business in such a way that I can
invent more things, that people here can invent more things. Like, every time I
say this, your eyes pop open because that’s what you want but the fear is that
your parents' retirement is at risk.
Joseph Bassett: Right.
Jerry Colonna: Right. Now let’s just hold in that place, okay? Remember before I said, the way
we turn fear from something that’s negative to something that’s powerfully
positive for us is to become friendly with it, even if it’s implausible. It’s like, I
name these things as demons and monsters, name the monster. Name him. It’s
implausible but that’s at the root of the conflict and so I think this low-level fear
you’re talking about isn’t as much about being afraid of failure as much as it is,
not taking care of your parents or not being able to live out what your heart
says.

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Joseph Bassett: Yeah because I really don’t – I take huge business risks a lot of times and like,
just that, it’s a very intuitive thing and yeah, what’s crazy is basically having to
work. You’ve got like complex tax situations when you have – I mean, as a
corporation, when you have estates and family businesses and things like this.
You have complex issues like that, all sorts of things but the only thing I’m
going to do, it’s like for me, it’s like – you know that movie 'Hoop Dreams'
about basketball? For me it’s like engineering Hoop Dreams where you invent
your way out of this bourgeois, middle-class, suburban America and it’s like no
matter what the fuck I’m going to do, we’re going to figure this out.
Jerry Colonna: I’m going to give you a piece of homework. I want an e-mail from you that tells
me what your mechanical 'Hoop Dreams' are. I want to understand what the
Hoop Dream is. And the reason I’m asking you to write it out is because I want
you to viscerally experience it. I want you to just play with it. Give voice to it,
not just sit there and do what I know you’re doing, which is mulling about it
when you’re online or at the bank or driving your car or something like that.
Really tend to that dream. Give some thought to it. Do you think you can do
that?
Joseph Bassett: Yeah I think there’s – I’m just going to finish with the anecdote that happened
to me the other day when I was in Düsseldorf, Germany. So, I’m starting to feel
there’s weird energy in the world about how things work and about like
different connections and things that are made because I was in the bar in
Düsseldorf and I got to talking with this bartender and it turns out he actually
just tends bar on vacation but he sells these electronic components and we got to
talking and he literally gave me this idea that I was just like, "Oh my God!" to
solve a critical, very hard problem in agriculture. And then I walk out of this bar
like ten minutes later, go out to the street and this enormous, fat man gets hit by
this bus.
Jerry Colonna: Holy mackerel!
Joseph Bassett: And I was just like, holy cow! Sometimes life is just life [sound effect] and my
time management has been sucking lately and you know, I’m just kind of like,
hold it together, you know, and move forward. But I think things are going to go
well but I will play with that.
Jerry Colonna: Do that and make a connection back to the man who got hit by the bus. I’d like
to know more about your connection between those two. Joe, I just want to
thank you for this. It was really wonderful seeing you again and talking with
you and being with you and e-mail me!
Joseph Bassett: Yeah, I will. It’s – I really enjoyed CEO boot camp too. I think it’s a great
product so.
Jerry Colonna: Thank you.

19. Reboot004_Hidden_Burdens
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Joseph Bassett: Okay.
Jerry Colonna: So we’ll get you to the alumni one.
Joseph Bassett: Sure sounds cool, thanks Jerry.
Jerry Colonna: All right buddy! Be well!
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
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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 0:49:11]