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Welcome to the Reboot podcast. We’re proud to say that today’s episode is brought to you by                                 
Justworks. Justworks helps businesses take care of their benefits, healthcare, payroll and HR. It’s                           
super simple and powerful. We use it and we love it. And this podcast really is way more than                                     
just Jerry so we wanted to take this opportunity to introduce you to more of our team, and hear                                     
their experience in using Justworks.  
 
A: I’m Ali Schultz, and I am the COO of Reboot. Justworks makes my life insanely                             
easy. It’s every HR solution I have ever wanted in one place, including my benefits,                             
and I don’t have to think about HR things at all.  
 
D: And how does your experience with Justworks compare to other providers that you                         
may have used in the past? 
 
A: I have tried two of the largest HR solutions in the market, and the time that it has                                   
taken out of my life, to use both of those programs, is maddening to me. Back then, at                                   
least a couple of years ago, I remember thinking to myself, ‘This really doesn’t need                             
to be as complicated as it is’ and I was hoping that someone would create what                               
Justworks has created. I feel like it has kind of given life, and a new­found sense of                                 
joy and freedom to HR professionals around the globe. 
 
D: Well, you hear how much Ali loves Justworks, and a happy Ali is a happy Reboot. If                                 
you are ready to grow your business and not your busy work, head over to                             
Reboot.io/justworks. You’ll find out more about how we use Justworks and how it                         
could work for you. That’s Reboot.io/justworks. 
 
 
“This is the temple of my adult aloneness and I belong to that aloneness as I belong to my life.                                       
There is no house like the house of belonging.” That’s from David Whyte’s poem, ‘The House of                                 
Belonging’. What’s it like to find your path of authentic service in the world? What if you could                                   
tap into your wholeness; your fears, your wounds, your purpose and build a company from that                               
place? What if you could use the pain of the past, a pain of not knowing where you fit in, not                                         
knowing where you belong, to propel you toward work that makes a difference. It might look a                                 
lot like what Tanisha Robinson and her team are building with Print Syndicate.  
 
Started just 2.5 years ago with eight people, Print Syndicate now has over 140 employees and it                                 
will generate more than 20 million in revenue this year. The company isn’t just about shirts and                                 
home­goods, it’s a place where people, including a black, gay woman, from a Mormon family of                               
seven, in a small town of Missouri, have a place to self­identify and a place to belong. It’s a                                     
place where they can find proof that they are not alone.  
 
As Tanisha shares, running a company fueled by her passion to make the world better is both                                 
exhilarating and heart­wrenching. In this podcast, I am thrilled to welcome my friend, Tanisha,                           
Reboot019_Building_House_Belonging.Mp3-Transcription 
 
one of my favorite entrepreneurs in a conversation with Jerry. They discuss Tanisha’s path to                             
building Print Syndicate, as well as the power and pain of connecting who you are, what you                                 
deeply care about, and what you do. Enjoy. 
 
JC: Hey Tanisha, it’s really great to have you on and thank you so much for joining us                                 
and taking the time. I know it’s a fast­growing company and it’s really helpful when                             
entrepreneurs take time out, and talk about some of these things. Not only for you but                               
as we – you know, we were talking about before we hit the ‘Record’ button, the                               
notion of just sharing that experience with other entrepreneurs and really talk about                         
that. So before we begin, why don’t you tell us a little bit about Print Syndicate and                                 
yourself, and you know, what are some of the things that you are working through. 
 
TR: Yeah, so my co­founder, Mike and I founded Print Syndicate in November of 2012                           
and we actually worked together in a company with sort of similar model and I think                               
it’s an interesting sort of, distinction I often point out. Often you don’t have to be an                                 
inventor to be an entrepreneur. You can just take an existing model, and if you have a                                 
better idea for it, it might be a promising business and that’s kind of how we came up                                   
with the idea of Print Syndicate. And so, we worked for a company that was like                               
CafePress or Zazzle where anyone could upload anything, and we had a different                         
vision around how content should be created and what consumers might want. So, we                           
started in November 2012 and we had us and a handful or artists and started                             
generating content based on what we saw as trends in social media. And you know,                             
the other interesting kinda thing about our business is that it’s – we use all on­demand                               
fulfillment processes. So everything is produced on demand and so if you can round                           
up enough money to do on­demand fulfillment, then it’s a pretty good way to                           
bootstrap. But you know – so that’s sort of the idea that we started with. Two years                                 
later, we had a very different version of what the model would be. I mean, it really                                 
took us a couple of years to nail down what we are actually doing. And so now, really                                   
we are in the business of self­expression but we focus half­way on trends and social                             
identities. So, the example I often give is, here in Columbus if you are a Buckeye fan,                                 
there are a thousand places to buy Buckeye t­shirts, but if you are an introvert, or a                                 
feminist, or a science geek, we are kind of the only creator of well­designed products                             
for people that want to express those elements of their social identity. We kind of,                             
think about ourselves as kind of the makers of products for unserved social identities                           
and we spend a lot of time thinking about that. People want to belong and the internet                                 
has allowed for these tribes of people, even very tiny tribes of people that can be in it                                   
in really unprecedented ways, and they want to express their belonging to those tribes                           
instead of sort of the old­school [Unclear 0:07:00] kind of tribes for the masses. And                             
so, that’s what we do but we kind of, outwardly look like a portfolio of niche brands                                 
that sell T­shirts and home­goods and that sort of thing. But yeah, the underlying                           
premise of our business is the people who wanna express themselves in unique ways. 
 
JC: You know, I feel like, you know, I stumbled upon someone who’s already read the                             
end of the book because I love what you just described. Not only – congratulations on                               
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Reboot019_Building_House_Belonging.Mp3-Transcription 
 
the business, the business is doing well, you’ll do over 20 million in revenue                           
forecasted this year, that’s fantastic but I can’t help but just jump right in. And you                               
saw me scribbling through and writing a bunch of notes and words like ‘We’re in the                               
business of self­expression’, you know, I think you used the word ‘social identity’                         
and ‘identity’ about 12 times.  
 
TR: Yeah. 
 
JC: Yeah and ‘people want a sense of belonging’ and that you know, ‘there’s tribes for                             
the masses and then there’s tribes in which people actually feel like they belong’.                           
That’s powerful, that’s powerful. 
 
TR: It is, I mean, it’s been a funny, isn’t it? It’s been a fun way to sort of, close a loop in                                           
my life. I grew up in a small town in Missouri, I’m the second of seven in a very, very                                       
conservative, Mormon family. 
 
JC: I have six brothers and sisters too. 
 
TR: Nice. You know, and in Liberty, Missouri, I wasn’t really a great fit. It was kind of a                                   
Friday­night lights, football­cheerleader, very, very traditional, evangelical event kind                 
of town and when I was in high school and junior high, AOL chat­rooms came out                               
and I was able kind of, find kids who were like me ‘cause there really were not kids                                   
who were like me in Missouri. And so that was kind of the first experience I had                                 
where I felt like okay, there’s a bigger world out there and there are people that I can                                   
get along with even if none of them were in my high school – or maybe one of them                                     
is in my high school, as was the case.  
 
JC: Right. 
 
TR: And so, I definitely – and I really struggled in high school because of that, because I                                 
didn’t feel like I didn’t fit in and I definitely didn’t fit in. I mean there was a sort of,                                       
question about that but you know, so it’s been interesting to be kind of be able to                                 
build a business around sort of thinking through people’s desire to belong. And you                           
know, it’s interesting in the world right now, because of the internet, because of the                             
social media, counter­culture is very mainstream. And so, it’s – you know, I kinda                           
wish that I was 20 years younger where it’s cool to be a nerd, and cool to be smart,                                     
and you know, cool to be different because when I was in high school, it was                               
definitely not. I mean, but it’s fun to be able to enable people’s weirdness a bit. 
 
JC: If you don’t mind, could we explore a little bit, the way in which you were different? 
 
TR: Yeah, you know, so growing up Mormon, my parents really raised us, raised me – I                               
have five younger sisters, they raised us to be wives and mothers. And so, you know,                               
the context from a cultural­religious stand point, I really was more interested in a lot                             
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Reboot019_Building_House_Belonging.Mp3-Transcription 
 
of other things. I didn’t want dolls, I wanted Legos, and I didn’t want to be raised to                                   
be a wife and mother. I wanted to go to school and do stuff, and then in my small                                     
town, like from the time I was very little, I thought I could change the world. And                                 
actually this is a funny story: I was in seventh grade and I had to write my own                                   
obituary, and I wrote – yeah for my English class or whatever, and I wrote that I had                                   
done so much work in helping that the poor people called me ‘Mother Tanisha’ and I                               
really dreamed that I was capable of doing something special. You know, and my                           
mother was very, very negative towards – any aspirations I had towards – or my                             
parents were both really negative. And so, you know, like there was kind of – I was                                 
kind of raised in a very, very confined structure and that didn’t fit me or sort of what I                                     
dreamt for myself than in the larger social structure, football­oriented,                   
cheerleader­oriented, white high school that I went to, and I didn’t even know that it                             
was possible to be gay. So I just thought, well, it’s easy to be a prude and I’m not                                     
really interested in boys. You know, but even in terms of my coming to terms with                               
my sexual identity, you know, took a long time because I grew up in a very sort of,                                   
suppressive and repressive environment. It wasn’t okay to be myself and I didn’t feel                           
like I was and so, it was a huge struggle for a long time. 
 
JC: So you know, again, I want to be mindful and really respect your own                           
self­identification; part of my own journey through my own, as we were sharing                         
before the recording began, becoming aware of my own unconscious biases, I want to                           
make sure that I am cognizant of the individual’s identification. So what I’ve heard                           
you identify is non­white and gay. 
 
TR: Yeah. 
 
JC: And do you also identify as a woman? 
 
TR: I do, yeah. 
 
JC: Okay and you know, I think – and what I’m also hearing is, identifying as someone                               
outside the norm of Mormonism –  
 
TR: Oh definitely, yeah. 
 
JC: – and so there is a – and I know, in a CNN interview, you described yourself as                                   
‘hyper­marginalized’. 
 
TR: Yeah. 
 
JC: Are those the things you were referring to? 
 
TR: Yeah, definitely. I think you know, and not that – fortunately, for the vast majority of                               
my experiences, because I had been fortunate to live in places where people are very                             
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Reboot019_Building_House_Belonging.Mp3-Transcription 
 
open and smart enough to typically not cause problems, you know, I think that when I                               
refer to being hyper­ marginalized, it’s really around the start up world that I function                             
in –  
 
JC: Yeah. 
 
TR: – where you look at the percentage of VC­funded startups, the number of women,                           
even co­founders, not necessarily CEOs, or black, or gay, or sort of in any category                             
besides straight white dudes or Asian dudes, is very, very, very small. And so, you                             
know, there’s a lot of times in my work that I – when I walk in there, I’m the only                                       
black woman, or gay person, or any kind of any – among those categories. And so                               
that’s what I would say I feel like I function in the margins but not so much sort of,                                     
day­to­day living here in Columbus, Ohio.  
 
JC: But is that – I hear that and I’m curious though ‘cause one of the things in working                                   
with clients that I often suggest is something that I found that you did almost                             
immediately, which was connect to a deeper sense of purpose –  
 
TR: Yeah. 
 
JC: – when you were describing the company mission. 
 
TR: Yeah. 
 
JC: And that’s what I sort of, leapt on and to me – so I’m making it into an association                                     
here and tell me if this is right that creating a service for people to find social identity                                   
and the sense of – and therefore, a sense of belonging, isn’t just a business                             
opportunity, but there is something connective there for you; is that right? 
 
TR: That’s totally true and it’s a huge driver because I mean, per­se, I am not interested in                                 
being in a T­shirt company – owning a T­shirt company; that’s not even appealing to                             
me. And so, you know, there has to be more purpose than that we sell shit and make                                   
money, because business­building takes so much sacrifice in terms of time, and                       
seeing people, and mental energy and so the opportunity cost is very high based on                             
anything else I could be doing in the world. And so, for me, it has to be more than just                                       
the Visa stuff and you know, and beyond that as like my whole, sort of, purpose in                                 
being an entrepreneur is that the company itself can be a lever for impact. I mean,                               
that’s been a huge learning for me as we have grown that – you know, we have 140                                   
people, but we also have a force of 140 volunteers, and we have a force of 140                                 
donors, and we also have some talents that allow us to offer unique things in support                               
of our community and causes that we care about. So not only do we have a business –                                   
that I get to work in a business and run a business that I think serves a good purpose                                     
and does a positive thing in the world. I think you know, then we also have a lever as                                     
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Reboot019_Building_House_Belonging.Mp3-Transcription 
 
a fast­growing company to make a difference as we build this thing. And you know,                             
so I think it’s very intertwined really.  
 
JC: Yeah, I can feel the interrelationship and the interdependence of sort of, the inner and                             
the outer here at the same time. And you know, many people who follow my work                               
know that I’m a huge fan and my friend, Parker Palmer and he often talks about when                                 
the inner and the outer are in congruence with each other, that there’s this powerful                             
opportunity that emerges, not only for the individual self­actualization but for the                       
community, for the organization, for the organism to really live itself out. And he                           
refers to not only the inner – the stuff that we are proud of, but also the pain and the                                       
stuff that we have placed back in the shadow. I feel like I’m speaking with a CEO                                 
who kinda just shrugs her shoulders and goes, ‘Yeah, of course’.  
 
TR: Yeah, I think it’s been – you know, it’s not necessarily a – well, actually, it is. I mean,                                     
it’s something that to me seems totally natural; like why else would I build a business                               
that I don’t deeply believe in my bones. But you know, I think it’s something that                               
might be a unique feature as a woman, and I don’t necessarily know what the reasons                               
are, but I know that I wouldn’t invest my life savings and all of my time and energy                                   
and effort and make sacrifices for a thing that wouldn’t really make a difference. You                             
know, ‘cause there are a lot of ways to go out and make money in the world, and so to                                       
pick the hardest fact, I think the challenge could be much worse, I guess. One in ten is                                   
kinda successful, where one in a thousand really and then for a lot of folks, it’s just a                                   
highly public failure. Sort of, dive into that and then, you know, at such great risk to                                 
my reputation, and my hopes and dreams, and sort of all that, you know, I can’t                               
imagine doing it any other way.  
 
JC: Mmm, that’s really beautiful, it’s admirable, it’s – it took me a long time, a long time,                                 
to get to the point where my work­self more closely matched my inner­self. And I                             
think I’m there now but I think you know, in looking back, I think that it took me a                                     
long time. So you know, I just admire that, I really do. 
 
TR: Yeah, I think – you know, for me, it’s been interesting because there are some aspects                               
of my inner­self that people gauge, and measure, and judge that you know, that we                             
sort of talked about earlier which is like I’m a black woman, I have a fro, I have a                                     
wife; and so, you know, there’s a lot of things about me that people measure and look                                 
at on the – I think that are just very inherent parts of who I am but – that people pay                                         
attention to. And so I can’t hide some of these major, major elements that some                             
people react negatively to; and so I found that it’s like well, I can’t – there’s sort of                                   
like, well, there’s the ‘I got the conservative white dude business version of me and                             
then –  
 
JC: Yeah. 
 
TR: – and then the real version of me. 
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Reboot019_Building_House_Belonging.Mp3-Transcription 
 
 
JC: Yeah. 
 
TR: I mean, I can’t – so it’s hard to fake for me because I look the way I do and function                                         
the way I do. So that’s why I have just decided to dive in on being who I am ‘cause                                       
it’s too hard to try to negotiate through the world any other way. 
 
JC: I love that expression of it in a sense and without minimizing at all any of the                                 
challenges you’ve experienced. In a sense, I hear you describing as ‘easier’; the word                           
that occurs to me is ‘truer’ –  
 
TR: Yeah. 
 
JC: – more authentic in that sense. So, I also am aware that you said something before we                                 
actually started recording which I thought was really powerful which was – and so                           
this stuff that we’ve been talking about, this is about five percent of the challenge. 
 
TR: Oh yeah. 
 
JC: Yeah, tell me about the 95% 
 
TR: Okay yeah –  
 
JC: And uh­oh, here comes Jerry, he’s going to start coaching. 
 
TR: Yes, I’m in. So, you know, I mean the current challenges we are facing now are, up                                 
until last year, we were a management team of two and so we rounded up a bunch of                                   
people that are really smart in their respective territories and were like ‘Okay, go’.                           
And trying to impart knowledge and strategies so that everyone is moving in the same                             
direction at the same time is infinitely harder than it looks even when everyone                           
believes [Unclear 0:22:01] even when you have people that are super­smart, with 10                         
or 15 years’ experience and even when you communicate on a regular basis, to try to                               
maneuver for the singular purpose, you know, in the midst of tons of tiny projects, is                               
you know, a huge thing that we are going to be probably solving for years. So it’s sort                                   
of this problem that we have created for ourselves which we have to solve, but you                               
know, it’s a really, really tough one. 
 
JC: So, how does it show up as a challenge? What are some of the things that happen? 
 
TR: Yeah, I mean, in microcosm, it’s like, all right we are going to watch this project and                                 
there’s not necessarily coordination before, and then people are moving in sometimes                       
opposite of competing directions, and then it takes twice or three times as long to get                               
the thing done. And then it’s not necessarily done in a way that anyone is particularly                               
happy with or in a way that aligns with sort of the longer term infrastructure context                               
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of the thing. And you know, so it’s like instead of moving forward, we spin our                               
wheels and move it – you know, pull things apart or move in different directions. So                               
it’s – you know, so that’s a super­tough one when you got – so 2.5 years ago, we                                   
were eight people and now we are at 140 and we trying to wrangle all of that. That’s a                                     
very, very intense learning experience to try to learn how to manage because it’s so,                             
so different.  
 
JC: What’s the hardest part of that? 
 
TR: I think it really just – I think that it’s – there is no one that will know the business or                                         
the long game better than Mike and I do, and so to try to convey that so that people                                     
can think about what they are doing in the larger context of what we are trying to do                                   
is super, super­tough.  
 
JC: What makes it so tough? 
 
TR: I think it’s really just trying to get everyone on the same page all the time because                                 
when you iterate so often and you know, so there are things that I see but you know,                                   
both in the world and in the business, that may change – like nudge our directions                               
slightly on a weekly basis and sort of, try to constantly convey those tiny iterations                             
which ultimately, at the size that we have, have a massive ripple effect if we don’t get                                 
them right is hard. 
 
JC: And when you see that it’s not being gotten right, how does that make you feel? 
 
TR: Oh, I mean it’s frustrating, and it’s super­discouraging because we are capable of – I                             
think we – I know we are really, really on to something and that we are fulfilling this                                   
very special place in the market. And so to not be doing it fast enough, and not be                                   
doing it big enough, and not to be doing it as well as we possibly can especially with                                   
the team that we have, is very frustrating.  
 
JC: So can I respond more coach­like with you? 
 
TR: Yeah, please. 
 
JC: So, two separate ​threats that I want to respond to, I hear you, I really do hear you and                                     
the first thing that I want to say is that there is a theme that I’ve been working with                                     
lately; there’s a talk I’ve been doing called, ‘Standing Still While Your Hair’s on                           
Fire: Surviving the Startup Life’ and ‘The Paradox of Caring’ and the paradox of                           
caring I think is really important here. Caring and connecting so much with deep                           
purpose creates an enormous amount of energy and as you know, I’ve explored with                           
other guests in the podcast, by reaching back into our pain, by reaching back into our                               
shadow, we actually access creativity and spontaneity that would otherwise be not                       
available to us ‘cause we are accessing the wholeness of who we are as a human                               
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being, and we are bringing that forward. And I think that a lot of the success that Print                                   
Syndicate stems from the fact that you guys, almost from the beginning, are sort of                             
accessing disenfranchisement, accessing not belonging, accessing a sense of                 
dislocation and with love and humor, finding ways to connect with that. And that’s                           
powerful. The problem with caring so much, and here’s the paradox part, is that it                             
actually increases the stress –  
 
TR: Yes. 
 
JC: – ‘cause what happens if you fail? 
 
TR: Yeah. 
 
JC: Right, so not only do you carry the burden of failure of ‘Oh, I lost all this money’,                                   
‘Oh, I’m gonna be penniless and homeless and the laughing stock of my town’, but                             
I’ll have let down this community that I care so much about. And you know, it                               
reminds me of a poster that a client once sent to me which was, ‘Stress is caused by                                   
giving a fuck.’ 
 
TR: Yeah, exactly. 
 
JC: Right, if we didn’t give a fuck, we wouldn’t be so damn stressed. 
 
TR: Oh yeah. I mean, people that clock in and clock out and don’t care, are not stressed at                                   
all. 
 
JC: That’s right. Well, let’s be fair to them, there’s the stress of dehumanization –  
 
TR: Yes. 
 
JC: – which is a different stress, right, it’s a kind of violence. So it’s a dehumanization so                                 
that is there but yes, the people who actually manage to really actually not care about                               
anything, and float along, I envy them. 
 
TR: Yeah. 
 
JC: So there’s that point that I wanted to share. The other piece I wanted to share is to                                   
take you back to this other thing which is – and it reminds me of something that a                                   
client once said to me which was, ‘You mean, I have to tell them the vision again?’ 
 
TR: Yeah. 
 
JC: And the answer is, yes. 
 
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TR: Yeah. 
 
JC: So, you’ve probably heard me say this but I’ll say it again, there’s three functions that                               
you have as a CEO: the first is to hold and promulgate the vision and that means our                                   
values, our purpose, our sense of why, our sense of the future, our sense of                             
differentiation, our sense of who we are on the planet as an organization, and when I                               
say ‘hold and promulgate’ I mean, literally with your body –  
 
TR: Yeah. 
 
JC: – with your being, every day, in how you walk, how you talk, and who you engage                                 
with, and who you hire, and what that process is; so it get’s embodied in everything.  
 
TR: Yeah. 
 
JC: The other two tasks are to build and maintain the team and then lastly, give them the                                 
resources that they need which goes beyond money –  
 
TR: Yeah. 
 
JC: – but goes to clarity and prioritization. So part of the challenge is realizing that you                               
have stepped into the practice of being a CEO. 
 
TR: Yeah. 
 
JC: And the word ‘practice’ is really important because you actually never achieve it.  
 
TR: Yeah, so I have the sense that it’s a totally unachievable thing and –  
 
JC: Totally unachievable. 
 
TR: Yeah, I mean, it’s been interesting to sort of, actually move through it and then move                               
into this place where I get to do my little bit and really think about those three things                                   
because you know, especially in the early days, it’s like I am also the shipper, and the                                 
trash picker­upper, and sort of, so many other very, very functional things of just                           
getting stuff that needs to be done. And like I would say now, for the first time within                                   
the 2.5 years, so really in the past four or five months has been where I feel like I got                                       
to really think through and live through those particulars of the role.  
 
JC: Right, and a lot of folks will then find themselves in the very difficult position of                               
saying, ‘What value do I add every day?’ 
 
TR: Yeah. 
 
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JC: Right? And I joke with people that I kinda want you bored at four o’clock, on a                                 
Friday afternoon, and going, ‘You know, maybe I’ll go home and hang out with my                             
wife’ because the goal is to get the machine operating –   
 
TR: Yes. 
 
JC: – in such a way that the drama is minimized; right? And then we go from this                                 
hyper­activity, up­and­down roller coaster, to a kind of, equiniminous state where we                       
just kind of like blip­blip­blip, up­and­down, up­and­down, and we have some fun,                       
and then we go home, and have a life, and we go have dinner, and we laugh, and we                                     
make love, and we have fun. 
 
TR: Yeah. 
 
JC: You know? 
 
TR: Yeah, I can see the path through the woods to that – you know, we are starting to get                                     
into a good spot with our team and you know, getting people the context and the                               
information they need to make the decisions that they are supposed to, and so to be                               
able to hand off decision­making and a lot of the process work is something I’m                             
really looking forward to. 
 
JC: Yeah, so that process and the dialectical tension between doing that and the feelings                           
that arise, which is ‘What am I doing?’ 
 
TR: Yeah. 
 
JC:  ‘What? Is this right? Am I –’ that tension point, that’s part of the practice as well. 
 
TR: Yeah, that’s a good point. 
 
JC: Right? So part of your job is to actually ​bare the feelings that arise without turning                               
the team into an object of your narcissistic, neurotic tendencies. 
 
TR: Yeah. 
 
JC: And by the way, ​[Crosstalk]​ well, guilty as charged. 
 
TR: Yeah. 
 
JC: Not only with my colleagues at Reboot, but with my family –  
 
TR: Oh yeah. 
 
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JC: – with my friends, because that’s our work. 
 
TR: Yeah. 
 
JC: It’s like the feelings arise, anxiety, sadness, anger, and what do we – where do we                               
create the most suffering? It’s when we don’t know what to do with those feelings,                             
and then we project them out; or as my friend, Parker Palmer says, “Violence is what                               
we do when we don’t know what to do with our suffering.” 
 
TR: That explains why my favorite workout is a heavy bag. 
 
JC: There you go! That’s what you do with your suffering! Hit the damn, heavy bag!                             
Exactly. 
 
TR: And how! 
 
JC: There is something powerful in what you just said because the path is actually to get                               
out of your head and into your body ‘cause the body is where all that feeling is going                                   
to get stored up, and that’s why so much of good coaching will pull people in and say,                                   
‘Great, did you go for a run?’ ‘Did you do some yoga?’ And it’s not just like for                                   
‘Namaste –’ you’re like Don Draper at the end of ‘Mad Men’  
 
TR: Yeah. 
 
JC: Spoiler alert, right?  
 
TR: Bummer. 
 
JC: It’s not that, it’s really how I’d be with all of this stuff that has charged up because                                   
what most leaders end up doing is, and we joke before [Unclear 0:34:04] the                           
organization into an object of their narcissistic neurosis.  
 
TR: Yeah, and I mean, I think that there are so many cautionary tales of that that for me,                                   
my biggest –I try to be very introspective because I mean, there’s a term for it, it’s                                 
‘Founder Syndrome’, where the CEO becomes a toxic leader and it does more harm                           
than good in the organization and you know, so I try – I’m trying and I hope to, for a                                       
long time, be very mindful of like – that I might hit that moment where I am not the                                     
right leader anymore, or that I am not in the right place as a human being to be the                                     
right leader anymore, to you know, let my investments make gains and let my people                             
be happy. If I am a hindrance to that or to the effectiveness of the organization, that’s                                 
something that I try and pay attention to, and I definitely, whole­heartedly believe                         
that I am the right leader for this company right now. But I don’t know if that will be                                     
the case in three years or five years. 
 
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Reboot019_Building_House_Belonging.Mp3-Transcription 
 
JC: So what I would suggest is, this is why community is so important. This is why                               
human beings, as a species, evolved in communities. Now, I’m a profound introvert                         
but even I need somebody to tell me when I’ve got a smudge of dirt on my nose;                                   
right? And community, and creating the conditions within the organization where                     
your co­founder Mike, can go to you, ‘Hey, Tanisha, that thing you did, that wasn’t                             
cool.’ 
 
TR: Yeah. 
 
JC: ‘Or this thing, this is not going on.’ ‘And what do you mean it’s not go –’ and then                                       
you have that point of contact and then that’s what we – you know, we often talk                                 
about, what if work were a means for the self­actualization, the full realization of                           
ourselves as human beings, including bringing our bag of tricks and our bag of shit                             
forward and processing that? What if work were a process for you as a human being,                               
to evolve to the full potential as a human being? Community can help us do that. 
 
TR: Yeah, and I think probably entrepreneurs get that closest to their work being, or                           
having a possibility of being part of actualizing one’s full potential. I mean, I think if                               
I were working in a corporation or doing anything, I’ll say, I would move farther                             
away from that than I feel like I am now. 
 
JC: I think you are right; I think one of the beauties and gifts of a startup organization is,                                   
we do commit ourselves to creating a culture. 
 
TR: Yeah. 
 
JC: And you know, as I often say to clients, what kind of company do you want to work                                   
for? ‘Cause you get to create that every day.  
 
TR: Yeah, and it’s been very fun in our business. We have a lot of ​creatives , a lot of                                     
artists, and a lot of odd kids that have found their place here. And you know, I think                                   
people really feel that they can come to work and truly be themselves, and be loved                               
and accepted, and valued for that. And you know, I would say it’s one of the things                                 
that I am most proud of that we have built, as I look around our team of misfit toys,                                     
and to see that, you know, they are happy, and they have got a best friend at work,                                   
[Unclear 0:37:33] lunch with, and they also have a chance to dive into this purpose of                               
helping other people express themselves. But it’s a pretty special and exciting thing                         
and it’s something that we are very, very intentional about from the beginning. It was                             
declaring our values and really thinking through – ‘cause one of my mentors told me,                             
even if you are – ‘If you are not intentional by your culture, you will still have one’                                   
and I think you know, there are other cautionary tales, there are lot of startups that                               
just become really, really horrible places because no one is keeping an eye out for                             
culture, and the experience for other people to show up to work every day. 
 
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JC: I think that is beautifully, beautifully said and I think you are absolutely right. You                             
know, one of the things like that motivates me and gets me excited about the work                               
that we try to do is to really create a place for the “island of misfit toys,” for the                                     
“caboose with square wheels”. 
 
TR: Yeah. 
 
JC: And we are both referring to Rudolph, the red­nosed reindeer. 
 
TR: Yeah. 
 
JC: And you know, I always related to them. I’m a white male privilege and yet, I always                                 
related to the caboose with square wheels ‘cause I cry at the drop of a hat because I                                   
feel in a way that not everybody else feels, and because I’m an introvert but I’m not                                 
shy.  
 
TR: Yeah. 
 
JC: And people don’t understand that when I withdraw, it’s because I’m depleted. 
 
TR: Yeah, I am also a charismatic introvert, is how I describe my personality ‘cause                           
people are like, ‘Oh, you are so good with people’ and that’s totally true. And you                               
know, I have unbelievable anxiety around public­speaking and networking events,                   
you know, I was a kid who had a birthday party who no one showed up to. And so,                                     
you know, those types of moments in your really early years, remind me of early                             
years were really so painful and I am perpetually like paranoid about ever facing that.                             
You know, because when you don’t fit in, it’s so hard, and so humiliating, and so then                                 
the idea of public­speaking, and being a public­facing figure for the business is –                           
gives me very, very intense anxiety. And I do it because it’s part of my role to tell our                                     
story, and you know, to be out in the community, and talk to our investors and talk to                                   
our people and then talk to our media – and you know, the fear even with all of the                                     
practice I’ve had at this point, the fear has yet to go away. 
 
JC: So two things I would say to that: the way I have come to be comfortable as a public                                     
speaker is, I really and truly pretend that I’m speaking to one individual. I fix my eyes                                 
on that one individual, and the funny thing that’s happened is, all of a sudden, I find                                 
myself – even if there’s a distance of a stage, I find myself having a physical heart                                 
connection with that one individual, and that gives me sustenance enough to get                         
through it. 
 
TR: Yeah. 
 
JC: The second thing I would say is, one of my favorite poems is a poem by David Whyte                                   
called, ‘The House of Belonging’. I won’t bore you with a full reading of it, but                               
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there’s a beautiful line in there which is, ‘There is no house like the house of                               
belonging and I belong there as I belong in my adult aloneness.’ And I love the notion                                 
of an adult aloneness because to me, it’s the notion of solitude versus [Unclear                           
0:41:22]  
 
TR: Exactly, yeah. 
 
JC: So you resonate with that line as well? 
 
TR: Totally, yeah. And fortunately, my wife is actually very extroverted but she knows                         
when I need time to do Legos. It’s not playing Legos, by the way – 
 
JC: I know what you mean though. You know, for me, it might be modeling, it might be                                 
clay, it’s something that allows me to just sort of [exhales] the world. 
 
TR: Exactly. Absolutely, yeah. 
 
JC: Yeah, I have so enjoyed talking with you. 
 
TR: Yeah, thank you so much Jerry, this was awesome and I appreciate the coaching. 
 
JC: You know, anything that I can do to support you in your process and you know,                               
anything that Reboot can do to help you in that regard, you know, I’m really grateful                               
for you coming on and sharing who you are in this moment. And as I said before, I                                   
am truly admiring of the way in which you are trying to live out your values in this                                   
way. It is really wonderful. 
 
 
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’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 night­vision, King of insight.” 
 
[End of audio 0:43:56] 
true.transcripts@outlook.comPage 15 
Reboot019_Building_House_Belonging.Mp3-Transcription 
 
[End of transcript] 
 
true.transcripts@outlook.comPage 16 

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Reboot Podcast #19 Building a House of Belonging with Tanisha Robinson

  • 1.       Welcome to the Reboot podcast. We’re proud to say that today’s episode is brought to you by                                  Justworks. Justworks helps businesses take care of their benefits, healthcare, payroll and HR. It’s                            super simple and powerful. We use it and we love it. And this podcast really is way more than                                      just Jerry so we wanted to take this opportunity to introduce you to more of our team, and hear                                      their experience in using Justworks.     A: I’m Ali Schultz, and I am the COO of Reboot. Justworks makes my life insanely                              easy. It’s every HR solution I have ever wanted in one place, including my benefits,                              and I don’t have to think about HR things at all.     D: And how does your experience with Justworks compare to other providers that you                          may have used in the past?    A: I have tried two of the largest HR solutions in the market, and the time that it has                                    taken out of my life, to use both of those programs, is maddening to me. Back then, at                                    least a couple of years ago, I remember thinking to myself, ‘This really doesn’t need                              to be as complicated as it is’ and I was hoping that someone would create what                                Justworks has created. I feel like it has kind of given life, and a new­found sense of                                  joy and freedom to HR professionals around the globe.    D: Well, you hear how much Ali loves Justworks, and a happy Ali is a happy Reboot. If                                  you are ready to grow your business and not your busy work, head over to                              Reboot.io/justworks. You’ll find out more about how we use Justworks and how it                          could work for you. That’s Reboot.io/justworks.      “This is the temple of my adult aloneness and I belong to that aloneness as I belong to my life.                                        There is no house like the house of belonging.” That’s from David Whyte’s poem, ‘The House of                                  Belonging’. What’s it like to find your path of authentic service in the world? What if you could                                    tap into your wholeness; your fears, your wounds, your purpose and build a company from that                                place? What if you could use the pain of the past, a pain of not knowing where you fit in, not                                          knowing where you belong, to propel you toward work that makes a difference. It might look a                                  lot like what Tanisha Robinson and her team are building with Print Syndicate.     Started just 2.5 years ago with eight people, Print Syndicate now has over 140 employees and it                                  will generate more than 20 million in revenue this year. The company isn’t just about shirts and                                  home­goods, it’s a place where people, including a black, gay woman, from a Mormon family of                                seven, in a small town of Missouri, have a place to self­identify and a place to belong. It’s a                                      place where they can find proof that they are not alone.     As Tanisha shares, running a company fueled by her passion to make the world better is both                                  exhilarating and heart­wrenching. In this podcast, I am thrilled to welcome my friend, Tanisha,                           
  • 2. Reboot019_Building_House_Belonging.Mp3-Transcription    one of my favorite entrepreneurs in a conversation with Jerry. They discuss Tanisha’s path to                              building Print Syndicate, as well as the power and pain of connecting who you are, what you                                  deeply care about, and what you do. Enjoy.    JC: Hey Tanisha, it’s really great to have you on and thank you so much for joining us                                  and taking the time. I know it’s a fast­growing company and it’s really helpful when                              entrepreneurs take time out, and talk about some of these things. Not only for you but                                as we – you know, we were talking about before we hit the ‘Record’ button, the                                notion of just sharing that experience with other entrepreneurs and really talk about                          that. So before we begin, why don’t you tell us a little bit about Print Syndicate and                                  yourself, and you know, what are some of the things that you are working through.    TR: Yeah, so my co­founder, Mike and I founded Print Syndicate in November of 2012                            and we actually worked together in a company with sort of similar model and I think                                it’s an interesting sort of, distinction I often point out. Often you don’t have to be an                                  inventor to be an entrepreneur. You can just take an existing model, and if you have a                                  better idea for it, it might be a promising business and that’s kind of how we came up                                    with the idea of Print Syndicate. And so, we worked for a company that was like                                CafePress or Zazzle where anyone could upload anything, and we had a different                          vision around how content should be created and what consumers might want. So, we                            started in November 2012 and we had us and a handful or artists and started                              generating content based on what we saw as trends in social media. And you know,                              the other interesting kinda thing about our business is that it’s – we use all on­demand                                fulfillment processes. So everything is produced on demand and so if you can round                            up enough money to do on­demand fulfillment, then it’s a pretty good way to                            bootstrap. But you know – so that’s sort of the idea that we started with. Two years                                  later, we had a very different version of what the model would be. I mean, it really                                  took us a couple of years to nail down what we are actually doing. And so now, really                                    we are in the business of self­expression but we focus half­way on trends and social                              identities. So, the example I often give is, here in Columbus if you are a Buckeye fan,                                  there are a thousand places to buy Buckeye t­shirts, but if you are an introvert, or a                                  feminist, or a science geek, we are kind of the only creator of well­designed products                              for people that want to express those elements of their social identity. We kind of,                              think about ourselves as kind of the makers of products for unserved social identities                            and we spend a lot of time thinking about that. People want to belong and the internet                                  has allowed for these tribes of people, even very tiny tribes of people that can be in it                                    in really unprecedented ways, and they want to express their belonging to those tribes                            instead of sort of the old­school [Unclear 0:07:00] kind of tribes for the masses. And                              so, that’s what we do but we kind of, outwardly look like a portfolio of niche brands                                  that sell T­shirts and home­goods and that sort of thing. But yeah, the underlying                            premise of our business is the people who wanna express themselves in unique ways.    JC: You know, I feel like, you know, I stumbled upon someone who’s already read the                              end of the book because I love what you just described. Not only – congratulations on                                true.transcripts@outlook.comPage 2 
  • 3. Reboot019_Building_House_Belonging.Mp3-Transcription    the business, the business is doing well, you’ll do over 20 million in revenue                            forecasted this year, that’s fantastic but I can’t help but just jump right in. And you                                saw me scribbling through and writing a bunch of notes and words like ‘We’re in the                                business of self­expression’, you know, I think you used the word ‘social identity’                          and ‘identity’ about 12 times.     TR: Yeah.    JC: Yeah and ‘people want a sense of belonging’ and that you know, ‘there’s tribes for                              the masses and then there’s tribes in which people actually feel like they belong’.                            That’s powerful, that’s powerful.    TR: It is, I mean, it’s been a funny, isn’t it? It’s been a fun way to sort of, close a loop in                                            my life. I grew up in a small town in Missouri, I’m the second of seven in a very, very                                        conservative, Mormon family.    JC: I have six brothers and sisters too.    TR: Nice. You know, and in Liberty, Missouri, I wasn’t really a great fit. It was kind of a                                    Friday­night lights, football­cheerleader, very, very traditional, evangelical event kind                  of town and when I was in high school and junior high, AOL chat­rooms came out                                and I was able kind of, find kids who were like me ‘cause there really were not kids                                    who were like me in Missouri. And so that was kind of the first experience I had                                  where I felt like okay, there’s a bigger world out there and there are people that I can                                    get along with even if none of them were in my high school – or maybe one of them                                      is in my high school, as was the case.     JC: Right.    TR: And so, I definitely – and I really struggled in high school because of that, because I                                  didn’t feel like I didn’t fit in and I definitely didn’t fit in. I mean there was a sort of,                                        question about that but you know, so it’s been interesting to be kind of be able to                                  build a business around sort of thinking through people’s desire to belong. And you                            know, it’s interesting in the world right now, because of the internet, because of the                              social media, counter­culture is very mainstream. And so, it’s – you know, I kinda                            wish that I was 20 years younger where it’s cool to be a nerd, and cool to be smart,                                      and you know, cool to be different because when I was in high school, it was                                definitely not. I mean, but it’s fun to be able to enable people’s weirdness a bit.    JC: If you don’t mind, could we explore a little bit, the way in which you were different?    TR: Yeah, you know, so growing up Mormon, my parents really raised us, raised me – I                                have five younger sisters, they raised us to be wives and mothers. And so, you know,                                the context from a cultural­religious stand point, I really was more interested in a lot                              true.transcripts@outlook.comPage 3 
  • 4. Reboot019_Building_House_Belonging.Mp3-Transcription    of other things. I didn’t want dolls, I wanted Legos, and I didn’t want to be raised to                                    be a wife and mother. I wanted to go to school and do stuff, and then in my small                                      town, like from the time I was very little, I thought I could change the world. And                                  actually this is a funny story: I was in seventh grade and I had to write my own                                    obituary, and I wrote – yeah for my English class or whatever, and I wrote that I had                                    done so much work in helping that the poor people called me ‘Mother Tanisha’ and I                                really dreamed that I was capable of doing something special. You know, and my                            mother was very, very negative towards – any aspirations I had towards – or my                              parents were both really negative. And so, you know, like there was kind of – I was                                  kind of raised in a very, very confined structure and that didn’t fit me or sort of what I                                      dreamt for myself than in the larger social structure, football­oriented,                    cheerleader­oriented, white high school that I went to, and I didn’t even know that it                              was possible to be gay. So I just thought, well, it’s easy to be a prude and I’m not                                      really interested in boys. You know, but even in terms of my coming to terms with                                my sexual identity, you know, took a long time because I grew up in a very sort of,                                    suppressive and repressive environment. It wasn’t okay to be myself and I didn’t feel                            like I was and so, it was a huge struggle for a long time.    JC: So you know, again, I want to be mindful and really respect your own                            self­identification; part of my own journey through my own, as we were sharing                          before the recording began, becoming aware of my own unconscious biases, I want to                            make sure that I am cognizant of the individual’s identification. So what I’ve heard                            you identify is non­white and gay.    TR: Yeah.    JC: And do you also identify as a woman?    TR: I do, yeah.    JC: Okay and you know, I think – and what I’m also hearing is, identifying as someone                                outside the norm of Mormonism –     TR: Oh definitely, yeah.    JC: – and so there is a – and I know, in a CNN interview, you described yourself as                                    ‘hyper­marginalized’.    TR: Yeah.    JC: Are those the things you were referring to?    TR: Yeah, definitely. I think you know, and not that – fortunately, for the vast majority of                                my experiences, because I had been fortunate to live in places where people are very                              true.transcripts@outlook.comPage 4 
  • 5. Reboot019_Building_House_Belonging.Mp3-Transcription    open and smart enough to typically not cause problems, you know, I think that when I                                refer to being hyper­ marginalized, it’s really around the start up world that I function                              in –     JC: Yeah.    TR: – where you look at the percentage of VC­funded startups, the number of women,                            even co­founders, not necessarily CEOs, or black, or gay, or sort of in any category                              besides straight white dudes or Asian dudes, is very, very, very small. And so, you                              know, there’s a lot of times in my work that I – when I walk in there, I’m the only                                        black woman, or gay person, or any kind of any – among those categories. And so                                that’s what I would say I feel like I function in the margins but not so much sort of,                                      day­to­day living here in Columbus, Ohio.     JC: But is that – I hear that and I’m curious though ‘cause one of the things in working                                    with clients that I often suggest is something that I found that you did almost                              immediately, which was connect to a deeper sense of purpose –     TR: Yeah.    JC: – when you were describing the company mission.    TR: Yeah.    JC: And that’s what I sort of, leapt on and to me – so I’m making it into an association                                      here and tell me if this is right that creating a service for people to find social identity                                    and the sense of – and therefore, a sense of belonging, isn’t just a business                              opportunity, but there is something connective there for you; is that right?    TR: That’s totally true and it’s a huge driver because I mean, per­se, I am not interested in                                  being in a T­shirt company – owning a T­shirt company; that’s not even appealing to                              me. And so, you know, there has to be more purpose than that we sell shit and make                                    money, because business­building takes so much sacrifice in terms of time, and                        seeing people, and mental energy and so the opportunity cost is very high based on                              anything else I could be doing in the world. And so, for me, it has to be more than just                                        the Visa stuff and you know, and beyond that as like my whole, sort of, purpose in                                  being an entrepreneur is that the company itself can be a lever for impact. I mean,                                that’s been a huge learning for me as we have grown that – you know, we have 140                                    people, but we also have a force of 140 volunteers, and we have a force of 140                                  donors, and we also have some talents that allow us to offer unique things in support                                of our community and causes that we care about. So not only do we have a business –                                    that I get to work in a business and run a business that I think serves a good purpose                                      and does a positive thing in the world. I think you know, then we also have a lever as                                      true.transcripts@outlook.comPage 5 
  • 6. Reboot019_Building_House_Belonging.Mp3-Transcription    a fast­growing company to make a difference as we build this thing. And you know,                              so I think it’s very intertwined really.     JC: Yeah, I can feel the interrelationship and the interdependence of sort of, the inner and                              the outer here at the same time. And you know, many people who follow my work                                know that I’m a huge fan and my friend, Parker Palmer and he often talks about when                                  the inner and the outer are in congruence with each other, that there’s this powerful                              opportunity that emerges, not only for the individual self­actualization but for the                        community, for the organization, for the organism to really live itself out. And he                            refers to not only the inner – the stuff that we are proud of, but also the pain and the                                        stuff that we have placed back in the shadow. I feel like I’m speaking with a CEO                                  who kinda just shrugs her shoulders and goes, ‘Yeah, of course’.     TR: Yeah, I think it’s been – you know, it’s not necessarily a – well, actually, it is. I mean,                                      it’s something that to me seems totally natural; like why else would I build a business                                that I don’t deeply believe in my bones. But you know, I think it’s something that                                might be a unique feature as a woman, and I don’t necessarily know what the reasons                                are, but I know that I wouldn’t invest my life savings and all of my time and energy                                    and effort and make sacrifices for a thing that wouldn’t really make a difference. You                              know, ‘cause there are a lot of ways to go out and make money in the world, and so to                                        pick the hardest fact, I think the challenge could be much worse, I guess. One in ten is                                    kinda successful, where one in a thousand really and then for a lot of folks, it’s just a                                    highly public failure. Sort of, dive into that and then, you know, at such great risk to                                  my reputation, and my hopes and dreams, and sort of all that, you know, I can’t                                imagine doing it any other way.     JC: Mmm, that’s really beautiful, it’s admirable, it’s – it took me a long time, a long time,                                  to get to the point where my work­self more closely matched my inner­self. And I                              think I’m there now but I think you know, in looking back, I think that it took me a                                      long time. So you know, I just admire that, I really do.    TR: Yeah, I think – you know, for me, it’s been interesting because there are some aspects                                of my inner­self that people gauge, and measure, and judge that you know, that we                              sort of talked about earlier which is like I’m a black woman, I have a fro, I have a                                      wife; and so, you know, there’s a lot of things about me that people measure and look                                  at on the – I think that are just very inherent parts of who I am but – that people pay                                          attention to. And so I can’t hide some of these major, major elements that some                              people react negatively to; and so I found that it’s like well, I can’t – there’s sort of                                    like, well, there’s the ‘I got the conservative white dude business version of me and                              then –     JC: Yeah.    TR: – and then the real version of me.  true.transcripts@outlook.comPage 6 
  • 7. Reboot019_Building_House_Belonging.Mp3-Transcription      JC: Yeah.    TR: I mean, I can’t – so it’s hard to fake for me because I look the way I do and function                                          the way I do. So that’s why I have just decided to dive in on being who I am ‘cause                                        it’s too hard to try to negotiate through the world any other way.    JC: I love that expression of it in a sense and without minimizing at all any of the                                  challenges you’ve experienced. In a sense, I hear you describing as ‘easier’; the word                            that occurs to me is ‘truer’ –     TR: Yeah.    JC: – more authentic in that sense. So, I also am aware that you said something before we                                  actually started recording which I thought was really powerful which was – and so                            this stuff that we’ve been talking about, this is about five percent of the challenge.    TR: Oh yeah.    JC: Yeah, tell me about the 95%    TR: Okay yeah –     JC: And uh­oh, here comes Jerry, he’s going to start coaching.    TR: Yes, I’m in. So, you know, I mean the current challenges we are facing now are, up                                  until last year, we were a management team of two and so we rounded up a bunch of                                    people that are really smart in their respective territories and were like ‘Okay, go’.                            And trying to impart knowledge and strategies so that everyone is moving in the same                              direction at the same time is infinitely harder than it looks even when everyone                            believes [Unclear 0:22:01] even when you have people that are super­smart, with 10                          or 15 years’ experience and even when you communicate on a regular basis, to try to                                maneuver for the singular purpose, you know, in the midst of tons of tiny projects, is                                you know, a huge thing that we are going to be probably solving for years. So it’s sort                                    of this problem that we have created for ourselves which we have to solve, but you                                know, it’s a really, really tough one.    JC: So, how does it show up as a challenge? What are some of the things that happen?    TR: Yeah, I mean, in microcosm, it’s like, all right we are going to watch this project and                                  there’s not necessarily coordination before, and then people are moving in sometimes                        opposite of competing directions, and then it takes twice or three times as long to get                                the thing done. And then it’s not necessarily done in a way that anyone is particularly                                happy with or in a way that aligns with sort of the longer term infrastructure context                                true.transcripts@outlook.comPage 7 
  • 8. Reboot019_Building_House_Belonging.Mp3-Transcription    of the thing. And you know, so it’s like instead of moving forward, we spin our                                wheels and move it – you know, pull things apart or move in different directions. So                                it’s – you know, so that’s a super­tough one when you got – so 2.5 years ago, we                                    were eight people and now we are at 140 and we trying to wrangle all of that. That’s a                                      very, very intense learning experience to try to learn how to manage because it’s so,                              so different.     JC: What’s the hardest part of that?    TR: I think it really just – I think that it’s – there is no one that will know the business or                                          the long game better than Mike and I do, and so to try to convey that so that people                                      can think about what they are doing in the larger context of what we are trying to do                                    is super, super­tough.     JC: What makes it so tough?    TR: I think it’s really just trying to get everyone on the same page all the time because                                  when you iterate so often and you know, so there are things that I see but you know,                                    both in the world and in the business, that may change – like nudge our directions                                slightly on a weekly basis and sort of, try to constantly convey those tiny iterations                              which ultimately, at the size that we have, have a massive ripple effect if we don’t get                                  them right is hard.    JC: And when you see that it’s not being gotten right, how does that make you feel?    TR: Oh, I mean it’s frustrating, and it’s super­discouraging because we are capable of – I                              think we – I know we are really, really on to something and that we are fulfilling this                                    very special place in the market. And so to not be doing it fast enough, and not be                                    doing it big enough, and not to be doing it as well as we possibly can especially with                                    the team that we have, is very frustrating.     JC: So can I respond more coach­like with you?    TR: Yeah, please.    JC: So, two separate ​threats that I want to respond to, I hear you, I really do hear you and                                      the first thing that I want to say is that there is a theme that I’ve been working with                                      lately; there’s a talk I’ve been doing called, ‘Standing Still While Your Hair’s on                            Fire: Surviving the Startup Life’ and ‘The Paradox of Caring’ and the paradox of                            caring I think is really important here. Caring and connecting so much with deep                            purpose creates an enormous amount of energy and as you know, I’ve explored with                            other guests in the podcast, by reaching back into our pain, by reaching back into our                                shadow, we actually access creativity and spontaneity that would otherwise be not                        available to us ‘cause we are accessing the wholeness of who we are as a human                                true.transcripts@outlook.comPage 8 
  • 9. Reboot019_Building_House_Belonging.Mp3-Transcription    being, and we are bringing that forward. And I think that a lot of the success that Print                                    Syndicate stems from the fact that you guys, almost from the beginning, are sort of                              accessing disenfranchisement, accessing not belonging, accessing a sense of                  dislocation and with love and humor, finding ways to connect with that. And that’s                            powerful. The problem with caring so much, and here’s the paradox part, is that it                              actually increases the stress –     TR: Yes.    JC: – ‘cause what happens if you fail?    TR: Yeah.    JC: Right, so not only do you carry the burden of failure of ‘Oh, I lost all this money’,                                    ‘Oh, I’m gonna be penniless and homeless and the laughing stock of my town’, but                              I’ll have let down this community that I care so much about. And you know, it                                reminds me of a poster that a client once sent to me which was, ‘Stress is caused by                                    giving a fuck.’    TR: Yeah, exactly.    JC: Right, if we didn’t give a fuck, we wouldn’t be so damn stressed.    TR: Oh yeah. I mean, people that clock in and clock out and don’t care, are not stressed at                                    all.    JC: That’s right. Well, let’s be fair to them, there’s the stress of dehumanization –     TR: Yes.    JC: – which is a different stress, right, it’s a kind of violence. So it’s a dehumanization so                                  that is there but yes, the people who actually manage to really actually not care about                                anything, and float along, I envy them.    TR: Yeah.    JC: So there’s that point that I wanted to share. The other piece I wanted to share is to                                    take you back to this other thing which is – and it reminds me of something that a                                    client once said to me which was, ‘You mean, I have to tell them the vision again?’    TR: Yeah.    JC: And the answer is, yes.    true.transcripts@outlook.comPage 9 
  • 10. Reboot019_Building_House_Belonging.Mp3-Transcription    TR: Yeah.    JC: So, you’ve probably heard me say this but I’ll say it again, there’s three functions that                                you have as a CEO: the first is to hold and promulgate the vision and that means our                                    values, our purpose, our sense of why, our sense of the future, our sense of                              differentiation, our sense of who we are on the planet as an organization, and when I                                say ‘hold and promulgate’ I mean, literally with your body –     TR: Yeah.    JC: – with your being, every day, in how you walk, how you talk, and who you engage                                  with, and who you hire, and what that process is; so it get’s embodied in everything.     TR: Yeah.    JC: The other two tasks are to build and maintain the team and then lastly, give them the                                  resources that they need which goes beyond money –     TR: Yeah.    JC: – but goes to clarity and prioritization. So part of the challenge is realizing that you                                have stepped into the practice of being a CEO.    TR: Yeah.    JC: And the word ‘practice’ is really important because you actually never achieve it.     TR: Yeah, so I have the sense that it’s a totally unachievable thing and –     JC: Totally unachievable.    TR: Yeah, I mean, it’s been interesting to sort of, actually move through it and then move                                into this place where I get to do my little bit and really think about those three things                                    because you know, especially in the early days, it’s like I am also the shipper, and the                                  trash picker­upper, and sort of, so many other very, very functional things of just                            getting stuff that needs to be done. And like I would say now, for the first time within                                    the 2.5 years, so really in the past four or five months has been where I feel like I got                                        to really think through and live through those particulars of the role.     JC: Right, and a lot of folks will then find themselves in the very difficult position of                                saying, ‘What value do I add every day?’    TR: Yeah.    true.transcripts@outlook.comPage 10 
  • 11. Reboot019_Building_House_Belonging.Mp3-Transcription    JC: Right? And I joke with people that I kinda want you bored at four o’clock, on a                                  Friday afternoon, and going, ‘You know, maybe I’ll go home and hang out with my                              wife’ because the goal is to get the machine operating –      TR: Yes.    JC: – in such a way that the drama is minimized; right? And then we go from this                                  hyper­activity, up­and­down roller coaster, to a kind of, equiniminous state where we                        just kind of like blip­blip­blip, up­and­down, up­and­down, and we have some fun,                        and then we go home, and have a life, and we go have dinner, and we laugh, and we                                      make love, and we have fun.    TR: Yeah.    JC: You know?    TR: Yeah, I can see the path through the woods to that – you know, we are starting to get                                      into a good spot with our team and you know, getting people the context and the                                information they need to make the decisions that they are supposed to, and so to be                                able to hand off decision­making and a lot of the process work is something I’m                              really looking forward to.    JC: Yeah, so that process and the dialectical tension between doing that and the feelings                            that arise, which is ‘What am I doing?’    TR: Yeah.    JC:  ‘What? Is this right? Am I –’ that tension point, that’s part of the practice as well.    TR: Yeah, that’s a good point.    JC: Right? So part of your job is to actually ​bare the feelings that arise without turning                                the team into an object of your narcissistic, neurotic tendencies.    TR: Yeah.    JC: And by the way, ​[Crosstalk]​ well, guilty as charged.    TR: Yeah.    JC: Not only with my colleagues at Reboot, but with my family –     TR: Oh yeah.    true.transcripts@outlook.comPage 11 
  • 12. Reboot019_Building_House_Belonging.Mp3-Transcription    JC: – with my friends, because that’s our work.    TR: Yeah.    JC: It’s like the feelings arise, anxiety, sadness, anger, and what do we – where do we                                create the most suffering? It’s when we don’t know what to do with those feelings,                              and then we project them out; or as my friend, Parker Palmer says, “Violence is what                                we do when we don’t know what to do with our suffering.”    TR: That explains why my favorite workout is a heavy bag.    JC: There you go! That’s what you do with your suffering! Hit the damn, heavy bag!                              Exactly.    TR: And how!    JC: There is something powerful in what you just said because the path is actually to get                                out of your head and into your body ‘cause the body is where all that feeling is going                                    to get stored up, and that’s why so much of good coaching will pull people in and say,                                    ‘Great, did you go for a run?’ ‘Did you do some yoga?’ And it’s not just like for                                    ‘Namaste –’ you’re like Don Draper at the end of ‘Mad Men’     TR: Yeah.    JC: Spoiler alert, right?     TR: Bummer.    JC: It’s not that, it’s really how I’d be with all of this stuff that has charged up because                                    what most leaders end up doing is, and we joke before [Unclear 0:34:04] the                            organization into an object of their narcissistic neurosis.     TR: Yeah, and I mean, I think that there are so many cautionary tales of that that for me,                                    my biggest –I try to be very introspective because I mean, there’s a term for it, it’s                                  ‘Founder Syndrome’, where the CEO becomes a toxic leader and it does more harm                            than good in the organization and you know, so I try – I’m trying and I hope to, for a                                        long time, be very mindful of like – that I might hit that moment where I am not the                                      right leader anymore, or that I am not in the right place as a human being to be the                                      right leader anymore, to you know, let my investments make gains and let my people                              be happy. If I am a hindrance to that or to the effectiveness of the organization, that’s                                  something that I try and pay attention to, and I definitely, whole­heartedly believe                          that I am the right leader for this company right now. But I don’t know if that will be                                      the case in three years or five years.    true.transcripts@outlook.comPage 12 
  • 13. Reboot019_Building_House_Belonging.Mp3-Transcription    JC: So what I would suggest is, this is why community is so important. This is why                                human beings, as a species, evolved in communities. Now, I’m a profound introvert                          but even I need somebody to tell me when I’ve got a smudge of dirt on my nose;                                    right? And community, and creating the conditions within the organization where                      your co­founder Mike, can go to you, ‘Hey, Tanisha, that thing you did, that wasn’t                              cool.’    TR: Yeah.    JC: ‘Or this thing, this is not going on.’ ‘And what do you mean it’s not go –’ and then                                        you have that point of contact and then that’s what we – you know, we often talk                                  about, what if work were a means for the self­actualization, the full realization of                            ourselves as human beings, including bringing our bag of tricks and our bag of shit                              forward and processing that? What if work were a process for you as a human being,                                to evolve to the full potential as a human being? Community can help us do that.    TR: Yeah, and I think probably entrepreneurs get that closest to their work being, or                            having a possibility of being part of actualizing one’s full potential. I mean, I think if                                I were working in a corporation or doing anything, I’ll say, I would move farther                              away from that than I feel like I am now.    JC: I think you are right; I think one of the beauties and gifts of a startup organization is,                                    we do commit ourselves to creating a culture.    TR: Yeah.    JC: And you know, as I often say to clients, what kind of company do you want to work                                    for? ‘Cause you get to create that every day.     TR: Yeah, and it’s been very fun in our business. We have a lot of ​creatives , a lot of                                      artists, and a lot of odd kids that have found their place here. And you know, I think                                    people really feel that they can come to work and truly be themselves, and be loved                                and accepted, and valued for that. And you know, I would say it’s one of the things                                  that I am most proud of that we have built, as I look around our team of misfit toys,                                      and to see that, you know, they are happy, and they have got a best friend at work,                                    [Unclear 0:37:33] lunch with, and they also have a chance to dive into this purpose of                                helping other people express themselves. But it’s a pretty special and exciting thing                          and it’s something that we are very, very intentional about from the beginning. It was                              declaring our values and really thinking through – ‘cause one of my mentors told me,                              even if you are – ‘If you are not intentional by your culture, you will still have one’                                    and I think you know, there are other cautionary tales, there are lot of startups that                                just become really, really horrible places because no one is keeping an eye out for                              culture, and the experience for other people to show up to work every day.    true.transcripts@outlook.comPage 13 
  • 14. Reboot019_Building_House_Belonging.Mp3-Transcription    JC: I think that is beautifully, beautifully said and I think you are absolutely right. You                              know, one of the things like that motivates me and gets me excited about the work                                that we try to do is to really create a place for the “island of misfit toys,” for the                                      “caboose with square wheels”.    TR: Yeah.    JC: And we are both referring to Rudolph, the red­nosed reindeer.    TR: Yeah.    JC: And you know, I always related to them. I’m a white male privilege and yet, I always                                  related to the caboose with square wheels ‘cause I cry at the drop of a hat because I                                    feel in a way that not everybody else feels, and because I’m an introvert but I’m not                                  shy.     TR: Yeah.    JC: And people don’t understand that when I withdraw, it’s because I’m depleted.    TR: Yeah, I am also a charismatic introvert, is how I describe my personality ‘cause                            people are like, ‘Oh, you are so good with people’ and that’s totally true. And you                                know, I have unbelievable anxiety around public­speaking and networking events,                    you know, I was a kid who had a birthday party who no one showed up to. And so,                                      you know, those types of moments in your really early years, remind me of early                              years were really so painful and I am perpetually like paranoid about ever facing that.                              You know, because when you don’t fit in, it’s so hard, and so humiliating, and so then                                  the idea of public­speaking, and being a public­facing figure for the business is –                            gives me very, very intense anxiety. And I do it because it’s part of my role to tell our                                      story, and you know, to be out in the community, and talk to our investors and talk to                                    our people and then talk to our media – and you know, the fear even with all of the                                      practice I’ve had at this point, the fear has yet to go away.    JC: So two things I would say to that: the way I have come to be comfortable as a public                                      speaker is, I really and truly pretend that I’m speaking to one individual. I fix my eyes                                  on that one individual, and the funny thing that’s happened is, all of a sudden, I find                                  myself – even if there’s a distance of a stage, I find myself having a physical heart                                  connection with that one individual, and that gives me sustenance enough to get                          through it.    TR: Yeah.    JC: The second thing I would say is, one of my favorite poems is a poem by David Whyte                                    called, ‘The House of Belonging’. I won’t bore you with a full reading of it, but                                true.transcripts@outlook.comPage 14 
  • 15. Reboot019_Building_House_Belonging.Mp3-Transcription    there’s a beautiful line in there which is, ‘There is no house like the house of                                belonging and I belong there as I belong in my adult aloneness.’ And I love the notion                                  of an adult aloneness because to me, it’s the notion of solitude versus [Unclear                            0:41:22]     TR: Exactly, yeah.    JC: So you resonate with that line as well?    TR: Totally, yeah. And fortunately, my wife is actually very extroverted but she knows                          when I need time to do Legos. It’s not playing Legos, by the way –    JC: I know what you mean though. You know, for me, it might be modeling, it might be                                  clay, it’s something that allows me to just sort of [exhales] the world.    TR: Exactly. Absolutely, yeah.    JC: Yeah, I have so enjoyed talking with you.    TR: Yeah, thank you so much Jerry, this was awesome and I appreciate the coaching.    JC: You know, anything that I can do to support you in your process and you know,                                anything that Reboot can do to help you in that regard, you know, I’m really grateful                                for you coming on and sharing who you are in this moment. And as I said before, I                                    am truly admiring of the way in which you are trying to live out your values in this                                    way. It is really wonderful.      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’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 night­vision, King of insight.”    [End of audio 0:43:56]  true.transcripts@outlook.comPage 15