Story 8: Life Isn't All Sunshine And Rainbows

Cameron Laird

Cameron Laird

Published on: 03 January, 2022

Updated: 01 December, 2022

Josh Barker

Family, Values & Open Struggles

Happy new year and welcome to the first episode of The Chirp in 2022! Just a couple weeks ago, we ended the year by bringing to you a special episode that was very opportune for the season of giving. A popular podcast host himself, Joe Casabona, joined us for a lovely conversation that you should certainly listen to entitled Story 7: Treat People The Way You Want To Be Treated.

To start off the year, we are coming to you with an amazing episode this week. Filled with stories of struggle, triumph, and an important lesson on the value of strong family bonds, Josh Barker joined us to take about his early days in Silicon Valley and how that time ultimately led him to take a risk and start City Innovation Labs.

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This Episode In A Nutshell

Struggling is a reality we rarely talk about openly. People love a good success story. A man walking across the moon or an athlete breaking a new record - we gawk and awe at the success of others, but never really take the time to think about all of the struggles that lead up to those culminating moments. You may not be Neil Armstrong, but you are someone with your own achievements, your own accomplishments, and your own successes. Take a moment to think, however, have you ever stopped to reflect on the struggles you overcame to get to that point? In our conversation with Josh Barker, thought leader behind City Innovation Labs, we did just that. Building a successful technology company takes more than just ingenuity and grit, sometimes it requires a bit of humility and in this case a brother sticking his neck out for his family financially when Josh had no options left to turn to.

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Audio Transcript of Story 8: Life Isn't All Sunshine And Rainbows

Opening Monologue

Hello and welcome back to The Chirp: A Podcast by Pigeon. Cameron Laird here with our first episode of 2022. I’m excited for this year, partly to see the world open up again but mainly to bring you more episodes and guests and more interesting stories to make those awkward tales of loans between loved ones a little more accessible and a little less taboo.

Had a great conversation with a fascinating gentleman, called Josh Barker, who runs City Innovation Labs, a tech company that builds custom software for other companies. Josh had some great stories about his own experience with personal loans, how it has always seemed to run smoothly for him based on his great family and their strong values, and how those values have transferred into his own working family in his company, City Innovation Labs. 

Josh talks about the aspects of a big move to a big city and a career change that can have financial implications, some positive some negative, but gives an honest, refreshing take on his journey up until this point. Hope you all enjoy and let's dive in.

Cameron Laird

Cool. Listen, Josh, thank you so much for joining me on The Chirp! And you are our first episode of 2022 which is most prestigious! No I joke, but it's great to have you on. I know you're obviously flat out before year-end. But yeah, I'd love to get to know your story. I was checking out your LinkedIn and I was very impressed with your previous roles and all that you've done in the past, leading up to City Innovation Labs. So would you mind taking it away and giving us a little bit of a brief rundown of your journey up until this moment?

Josh Barker

Yeah, sure. So my background is mostly in engineering, so I was a software engineer, classically trained, and I started programming when I was 14 on my parents' Atari. So creating larger size asteroids and smaller size asteroids and all sorts of those things, for those that know asteroids. But yeah, as an engineer, I grew up in that space, so I can speak the development lingo and eventually where that brought me was at a company called KPMG. So I worked there as a Director of Innovation. And so my buddy had called me up out of the blue. I was there for about three or four years (he had moved to Silicon Valley the year prior) and he called me up and said, "Hey, Josh Barker I was out to breakfast with this accredited investor. I had no idea he had money, and I just pitched him on this idea and he just wrote me a $150,000 check!"

And he's like, "Whoa, I would love for you to leave your job and come with me." And I was like, "Well I know that sounds like a lot of money. It's not actually a lot of money, but I will help you learn how to use it in the best way possible". And so in the next couple of months I helped him figure out how to use it. And then he called me back up. I thought we were just going to talk about the project and it was about three months in. And so he's like, "I just raised over a million in seed funding, is that enough?" And I was like, okay, now we can actually talk about me leaving my stable job at KPMG and moving over to the startup.

So that's what I did. I moved over to Silicon Valley for about three years. Telecommuted over there, flew out there for a week or two at a time, would fly back and learned a lot out there. So I'd been, as I had mentioned, an engineer. I've been classically trained. The way I like to describe it is how to build the right thing. So you pop open the hood and you can make it run really, really fast. But out in Silicon Valley, I was taught not how to build the right thing, but how to build the thing right. And that's a huge difference, right? One is you pop open the hood and you can make it run quick and efficient. And the other one is, well, who cares if you make it run quick and efficient if no one wants to buy it! So that's where my career took a shift of learning about a lean startup. How do you find the right product-market fit? How do you build things that people actually care about?

And so for us, the next three years, I was out in the valley and, out of the three years, learning, working with people from Google Ventures and people working from Y Combinator, learning from all these really smart people, it eventually led into starting a firm called City Innovations.

And so what we do is we help people build the right thing. That's what I like to say because there's a difference between building the thing right and building the right thing. So how can we help organizations build the right thing? We work with entrepreneurs and intrapreneurs on how to build that right thing.

And it's much harder than you think, because if you take just Airbnb as an example, a lot of custom software development firms will just build it. And they'll say, “Here's the keys, go run with it!” And if you go and build Then, if it's a two-sided marketplace like Airbnb, you could build it, but what's the value in it? If there's no properties, like why would you use it, right? So there's something missing and that's what we help companies do is find that missing something. 

Cameron Laird

So you're really doing a deep dive on the story of a company and a product, because you can't leave any stones unturned. Would that be a fair assessment?

Josh Barker

Yeah. I mean, if you, if you simplify it to that level, yeah. I mean, we help companies go through a lot of… - Airbnb started with spreadsheets and they rented out their own apartment and that's the part no one sees, right? They started out very scrappy and they grinded to get where they're at.

And so what people don't realize is, months into starting Airbnb, they were running the whole company off of spreadsheets and renting out other people's apartments on Craigslist. They had no And so that's the part that people miss. They just don't understand the origin stories of ‘how did they get to where they're at?’

And that's what we call that space: “zero to one”. And so we focus on that zero to one space of before, there's a story of, “have you visited”

We help fill in the blank company. We help the pre-story. The background story, so to speak.

Cameron Laird

So yeah cool. Very interesting. And what was it like moving to Silicon Valley initially? Was it a big change for you? Was it very exciting? What were your initial impressions? 

Josh Barker

It was a huge change. Yeah, exactly. So in moving out of the Midwest, which is traditionally very conservative, and so moving to Silicon Valley was a big difference.

I mean, there's huge differences between the two areas with risk appetite, right? In the Midwest, going out to breakfast and having someone write a $150,000 check, that just doesn't happen! So people just don't invest that early on. So going out to the valley and having that, those kinds of people that are willing to take a risk on a really good idea, there's a lot more of that appetite, a lot more innovation and that's what it fuels, right? 

Taking more risks is equivalent to… - the outcome of that is usually more innovation. So yeah, I mean, that's probably one of the biggest key differences. I mean, there's a lot of others, the differences of people and that come out of that, but that's probably the underlying key difference that we see that I saw.

Cameron Laird

Migrating there and starting your new life, any tales where you thought working relationships, or even you with your friends, were somewhat affected by money and lending? I imagine you were in a financially stable position from your nice job at KPMG. So what was it like going out there? Any stories where things were affected?

Josh Barker

Oh yeah. Yeah. I can tell you all sorts of… It's a great assumption to say that I was very financially stable and I had no money problems. 

Cameron Laird

Haha, excuse my assumption! 

Josh Barker

No, no, you're good! I mean, I think that's the whole purpose of this though, right? The whole purpose of Pigeon is breaking down a lot of those barriers of people being open and honest. I can be real with how things happen because the origin story of how City Innovations started is not something I talk about a lot. I don't think entrepreneurs do! I don't think enough focus is put on it.

The analogy I give is like, you've seen those motivational posters where you're like, I don't know, “Perseverance!”, and it's a guy climbing a mountain or something like that. Well, one of them is like that and one that I really resonate with is “Failure!” And it's a picture of this iceberg. And underneath the water is the rest of the iceberg. And all people see is the top of the iceberg, right? So it's like the tip. So that's the thing is like, you looked at my resume and you started out with like, “Oh, it's a really impressive resume.”

But there were tons of failures to get to that point. And so going back to your question of like, what is that, what was that process and what did it look like? I remember when I left KPMG and one of the things that I looked at, I had a very cushy job and I said, “I know I'm going to have to make sacrifices.”

And as I moved over, one of the things I looked to do is to see if I could maintain the same lifestyle. And that's impossible when you're going from a very cushy large company to a startup. A lot of sacrifices had to be made. And so my wife and I made big… we took a big pay cut, right? Took over a 50% pay cut.

You need to go work at a startup. But I mean, obviously there's risk and there's rewards. So we looked at the reward and we're like, okay, the outcome could be a good thing, I remember distinctly there was a season of Winter we were going through. Middle of winter in Michigan, mind you, which is freezing!

If you don't know Michigan weather, it's freezing and so, and I remember my first. And in that moment, my furnace broke. I looked at the bank account because we made cuts and all these areas, you have to also make lifestyle cuts. Right. And so it was about a couple of years in, and we had been putting things on credit cards because we couldn't make it with just the salary cuts and all that stuff.

So we were trying to keep reducing. And so I looked at that and I was like, my furnace broke. I've got these credit cards and I have no way of paying for this furnace that broke. I don't have the savings we put into the business, and so I'm sitting here over-leveraged as an entrepreneur, and this is a story that people don't tell with entrepreneurs, right? And so you look at it and you go, what am I going to do? And I literally was on my knees, like praying. I'm like sitting here going, I don't know what I'm going to do. 

And so the next day my brother took me out to breakfast and he's like, “What do you need?” And I was like, “Honestly, man, I don't know what I need. I just need you to pray for me!” And he's like, “How about I just give a five grand loan to you?” And so this is where Pigeon comes in because those early stories of entrepreneurs like myself, who you look at and you go, you could say I'm successful. You could say, mediocre. You could say whatever you say or however it appears. I am like, it's really different. The different story underneath for almost anyone that's true. Right? So, that's where I think tearing down those walls with Pigeon and being able to have those stories be more normalized and having it be like, “Hey, this happens all across the world!”

These loans from your brother or your father… No, even rewind previous to that. I remember when my mom, we were in a situation where my parents were very financially strapped and my brother and I had jobs and we were living at home and we had really no financial obligations.

We did the same thing with my parents, right? It’s being able to loan them money as they needed it. And so the thing that I love about Pigeon and that as a concept, because I get to work with you guys on a few different things, is I love the fact that I had to create my own mechanism for keeping track of my loans. My dad really wanted to make it a loan, right?

And so did I! When my brother is like, we're really wanting to make it a loan, we want to pay it back, right? And so for us, it's like, how do we keep track of the amount of money that we're loaning and the terms and all of those different things. And so we had a very janky spreadsheet mechanism. I'd have to remember, and I have to remind, and so it was both with my brother and my dad and me receiving money and having to pay my brother back and be with my father where he'd pay me back. 

So it just ended up being a mess, right? So it just was very difficult to keep track of. So. I admire a lot of what you guys are doing at Pigeon because it's so needed in the area of all of that is happening behind the scenes, but bringing it to the forefront and saying, “Hey, we want to invest some time and energy into helping these people.”

Cameron Laird

Absolutely, great stories. There are a couple of questions on that, I suppose having that conversation with your brother, it's not the first positive story that we've heard on this show about family members giving dig-outs, or siblings looking after each other. Definitely, brotherly love has featured on The Chirp before. That, to me, is a good sign of a good family that has good financial values as well.

Obviously not just you and your bro, but you're your parents as well. Why do you think that's the case? Why do you think, for other people, it wouldn't be the case? Any examples of how you were raised and why that ethos exists within your family personally?

Josh Barker

Yeah. It's a good question. And for us, I mean, it really boils down to priorities, right? Someone told me that if you look at someone's resources. And so resources, if you break that down, time is money, right? If you look at their resources and you go, If you've created a pie chart, where is the majority or where is the majority of that time going?

And if you were to break that apart, the biggest, I think, influence my father had on me and my family was, hey, when that happens and we do a breakdown, really, those should be bucketized. For us, we are a very faith-driven family as God. But family, to answer your question is like, that was a huge part of that pie chart and your family should be a big part of that pie chart of investing into your family.

And that means time and that means money. And so you should be able to look at someone. Bank account and put it into a pie chart and create categories and say, what does this person care about? And that tells a lot about a person, right? And so for me, I think that was super influential in that process to know that caring about other people and caring about my family and caring about even friends, right.

What does my pie chart look like? And I think for me, that's the thing that I look at as I go, how are my resources being, if someone took an insight into my calendar or someone in Pigeon Loan's case, took a look at my pocketbook and took a look at my bank account. Am I being what, what I would call a good steward of that money?

Am I putting that to good use? And so for me, I think, having more of those conversations. And I think it really starts with family values. I think what you were implying is like, for me, it really started there of having that instilled from a really young age of, these are really important things! Family really is really an important bond here. 

Cameron Laird

Awesome. And it's quite evident as I was reading an article or a blog post you'd put up on City Innovation Labs, explaining the COVID situation and how you were asking your staff to work remotely. It's quite evident that these family values that you're talking about have transferred as well into your company. Can you talk a little bit about that? Is that a fair assessment? 

Josh Barker

Yeah, absolutely. So that's one of the things that we really want to instill and support our people in doing is giving. So I think that's a big thing. Like we just got off of a team week, a couple of weeks ago. There's an organization here in town called Alpha Ministries. So they were originally just a women's ministry, but they moved into men where those people are really in rough straights, right? And they’re maybe a single mom, a single dad, and they're really having a hard time financially, keeping up. And so they support those people through those hard times.

And so we give back our time, right? We gave back time. We volunteered and we helped clean. We helped really go around the facility and do whatever they needed us to do as hands. And then we followed that up. One of the cool things that we have on our team, a couple of team members put together a walking challenge, which is really neat.

And traditionally you have these walking challenges. I don't know if you're familiar with employee walking challenges where everyone gets in their steps. And so, a lot of times, you'll give the winner a gift card or whatever it is. And for us, the whole team decided unanimously, “Hey, at 100,000 steps, we want the winner to give Alpha Ministries a donation!” And so we actually made it, donation-based where it was like, Hey, we're going to add certain steps. We're going to add them all up and we're going to actually give this out to Alpha. And so it was pretty neat to see, to be a part of that. And to have me almost take a step back and just be a participant.

And it was neat to see our own people self-organize around their desire to do that. 

Cameron Laird

Fantastic. So they took initiative and followed the ethos that you had initially implemented and they're doing their own thing and creating an organic culture, that sounds pretty cool. 

City Innovation Labs: The future! What does that hold? It’s always a question I like to ask a guest because everyone that comes on is always quite successful, but there's always so many plans for growth that they have. And I'm curious, your year ends now. What does 2022 and beyond hold for City Innovation Labs?

Josh Barker

Yeah, it's a good question. I think that for us, we've always wanted to grow. We started with this semblance of values, right? Of having these core values. For us, we've had discussions of growth as entrepreneurs. You always have this discussion of like, well, how big do you want to grow?

So a lot of people say, well, I want to just grow as big as I can! And I appreciate their heart but like for us, it's looking at it and saying, well, sometimes there's… - I've experienced this too. There's too fast of growth. And when that happens, what's really difficult is to keep the ethos, like, as you said, Cameron, and to keep those same values intact if you grow so fast. So for us, it's like, we're really constant. 

Cameron Laird

It's tough.

Josh Barker

It's tough, yeah. So for us, it's like, we want to have growth that is very organic and it's gradual and it's something that we can manage. And I know everyone is in agreement within City Innovations that we intentionally have set ourselves up to where it's like, we don't want to grow past a certain point and we want to keep it small enough.

When I'm walking down the hall, whether that's virtually or in person, I want to be able to know, oh, that's Sally and I know her kids and I know her husband! I have a more intimate relationship with the employees and the people around me. I know who they are and what they like and what they dislike with their personality and their hopes and their dreams.

Versus, you walk into a large company, which I've worked at KPMG. I mean, they'd have like a quarter-million people, so it's like you walk in and you're just a really small, tiny speck of dust in a huge organization. For me, I want to build something that people feel like they contribute and that they matter.

And we're building things that matter to the world too. Then that's our biggest thing is for us, we want to build not only the right thing but build things that matter to the world which would mean things that change the world, things that support and have a vision and a mission beyond just growth, growth, growth, growth, growth. It’s to give back!

Cameron Laird

Fantastic. Because I've worked at a big tech company and when I started off, they were already back in my home country of Ireland. So they had an EMEA headquarters and all the rest of it and they reiterated how they still had this startup mentality. That was what they prided themselves on, but it just wasn't the case. Yeah, so it's refreshing and great to hear that, not that you don't want to even say that we still have that mentality, but you're actually insuring and putting plans in place to make sure you don’t scale too much, which is great.

And it's interesting because you are in an industry or in a niche where you operate behind the scenes, would that be fair to say? You're not advertising yourselves as… it's just the business that you're in. You build things for other people and other companies. So is that good to be able to stay under the radar and ensure that you can cap your growth? 

Josh Barker

Oh yeah. A hundred percent. There's a great marketing analogy that I just love, which is, I don't know if you're familiar, Cameron, with the hero's journey.

The hero's journey of every story has some key ingredients. So there’s a hero and it has a sage. It has an objective to save the princess or something. And it's got a sword, right? So, and so if you look at Star Wars, as an example, they have the ingredients.

So they have Luke Skywalker. He's given a lightsaber by Obi wan Kenobi, who is the Sage, and he's got to go save the princess. And so it's like, you can see this as a model for storytelling. And so how it applies here in my mind is, you were mentioning, are you, is it accurate? You want to be behind the scenes?

Well for us, well, from a marketing perspective, it used to be that, yeah, we want to be the hero! Like as a business, we want to be the hero. And I think coming to the realization that like, no, that's not your role. Like our role is we're successful. If we are safe playing the role of Sage and really our customers are Luke Skywalker.

Like we're Obi Wan Kenobi, they're Luke Skywalker. They defeat Darth Vader in the battle, we give them the lightsaber, we help them and we're like, you go do it! And so if we can do that and be that behind-the-scenes person of Obi Wan Kenobi, I don't know if anyone's a Star Wars fan, listening to this, but hopefully, there are some...

Cameron Laird

They should be, I know I definitely am! 

Josh Barker:

Haha! Anyway, but yeah, so that's what we want to be. We want to be intentionally behind the scenes and we're out to make our customers be the heroes and everything they do.

Cameron Laird

Fantastic, brilliant Josh. And if listeners want to get in touch and learn more about you. How do they find you? And what's the best way to reach out? 

Josh Barker

Yeah, I would say go to They can also shoot me an email. So my name, my email address is very simple. So shoot me an email, go to our website. If there's anything I can do to help you, we'd love to have a conversation at the very least. 

Cameron Laird

Fantastic. Well, listen, thank you so much. For, for joining us and giving us such a cracker of an episode in 2022. And yeah, I look forward to sharing this with everyone. Thanks again.

Josh Barker

Awesome. Hey, thanks Cameron. I really appreciate it.

Outro Monologue

Our first guest to use a Star Wars comparison! Delighted about that. We need more those analogies, of that I most sure. And yet another example of sibling support from Josh. A brother sitting him down and, without being asked, lending him a sizeable chunk to keep him afloat and support him through his new uphill journey in Silicon Valley. 

It’s great to see family values come back again which is such a common theme on The Chirp. The Barker men seem to have the right idea when it comes to family loans. There is no problem giving the loan, as long as it's all done properly and by the book. Josh Barker really appreciated Pigeon as a platform as well and I think that it sings to most people that have this strong bond and trust when it comes to money because it aligns with that trust and that practicality.

And I knew from reading that blog I mentioned where he implores his staff to say safe, stay at home during the lockdown, that Josh cares about his staff and cares about their well-being. When you come from a good family with good values, it transfers to others when you yourself grow up and I could see that same personality shine through, from Josh, professionally and personally. 

One final takeaway is, while this chat with Josh Barker was largely positive, he did say how speaking about your losses and your bad times is also hugely important for an individual, for a business, it is important for entrepreneurship in general. And that is why this podcast is so important as well. To quote Rocky Balboa, “life isn't all sunshine and rainbows”, and I feel it is imperative for the success of a business, for the betterment of living one’s life, that we chat about our losses and we chat about our struggles because it makes the good times and the successful stories all the more powerful and relatable. 

That’s all for today everyone! Be sure to get in touch should you have any questions or want to come on the show to chat about your own stories of lending! Until mid-January, I hope you all have an awesome start to the new year and we will see you again in 2 weeks. Take care!

About the author

About the Author

Cameron Laird

Podcast Host of The Chirp

Cameron Laird is a professional podcaster for Pigeon and the host of The Chirp podcast. He has a passion for creating content that is both entertaining and informative. Having hosted numerous ventures over the course of his career, his experience in the podcasting industry has made him a valuable asset to the Pigeon team. Cameron's ability to connect with his audience and provide meaningful content regarding topics like financial education has helped grow The Chirp to be a staple within the Pigeon community. He is an excellent communicator and is committed to improving the world through conversation, dialogue, and shared experiences.