Story 20: Our Best Moments So Far

Cameron Laird

Cameron Laird

Published on: 23 June, 2022

Updated: 01 December, 2022

Best Moments Title Slide

Laughs, Cried & Good Memories

This week we've hit a major milestone with The Chirp - it's our 20th episode! For such a momentous occasion we've got a special treat of an episode for you this week. But, before we get into that, you should check out our last riveting conversation on the podcast. A couple of weeks ago we sat down with the startup founder, Y Combinator alum, and Ph.D. whiz, Jon O'Bryan! Talented in pretty much every regard, we got a chance to talk with Jon about all things financial wins and losses and unpacked his stories regarding the times he had to depend on his family to get through tough times. Check out Story 19: Trust & Support Are The Keys To Success before diving into our special 20th episode.

Well for our 20th, we are completely flipping the scripts and giving you an episode of nothing but hits. That's right, this week we are bringing back some of our favorite moments from throughout the season so far. From Daniel's incredible jaw-dropping tale of financial ruin from a divorce gone bad to Rahama's impact in the world of sustainable agriculture and gender equality in Africa, we've compiled all the greatest hits of The Chirp thus far and put them all in one episode for your listening pleasure. Whether you are a new listener or you've heard these stories before, take a look back at the best moments from our community!

Pigeon Divider

This Episode In A Nutshell

For our special 20th episode we are recapping some of the greatest hits from The Chirp so far. We've brought you stories from entrepreneurs, writers, musicians, thinkers, artists, philanthropists, travelers, mechanics, and so many more. Each with their own unique story, we've had conversations with so many amazing folks about their trials and tribulations with money and how in those times they depended on their friends, family, loved ones, and community to make it through. Sometimes these stories did not end well and other times everything worked out for the best, but all in all, they all share a common thread and voice that we at The Chirp want to continue to create a space for. So without further ado, here are our greatest moments from the podcast so far!

You'll find this episode of The Chirp on:

Or wherever you listen to your podcasts.

Have a story to tell and want to be on our podcast? Let us know by sending an email to

Pigeon Divider

Audio Transcript of Story 20: Our Best Moments So Far

Opening Monologue

Hello everyone! Big episode today for The Chirp! Today is our 20th episode and I thought that for this week, instead of having a new guest on, we would take some time to appreciate some of our awesome guests that have come on before, and what specifically I have learned as a host!

We started The Chirp back in September 2021 with the aim of hearing some amazing stories of how relationships between loved ones can be affected by money and by loans, how people can make mistakes in these scenarios, and how they learn from these mistakes as well moving forward.

I was hired by the Co-Founder of Pigeon, Brian Bristol, to come in build out this podcast and interview all these amazing people and, let me tell you, I was no behavioral psychologist, I was no personal finance expert, I was just a normal guy looking to learn - much you like listening or watching right now. 

And this has been a huge learning experience for me, talking to all these successful people. Entrepreneurs, expats, content creators, all with stories of financial struggle and how they all asked for help with money. 

And during the last 19 episodes, I’ve noticed some patterns, some similar types of stories that keep coming up over and over again. Because these are all human beings that I’m chatting to. Whether people grow up poor, rich, alone, or with family, we all have the same needs when it comes to money. 

And whether these stories are positive or negative, I find them refreshing, because this podcast is here to educate you. Our guests have come out on the other side after witnessing and living through financial hardship.

There would be no Chirp without our guests, so this episode is for you! Thank you for all the great stories, and I wish I could play them all, but unfortunately, this episode would be too darn long. So I’ve chosen my favorite clips from the last 19 episodes that I feel were most educational for me, embodied the mission of The Chirp, and that I believe are very entertaining. 

So starting off, I want to talk about one of the main themes I hear from our guests - Divorce! Marrying your soulmate doesn’t always work out, and the financial implications can be tough. Let’s go back to Episode 1 with Daniel Cruz, CEO of WashBnb, who tells us about his experience.


Daniel Cruz: So I went through a divorce after moving to Milwaukee, and the house was part of it. And it was something that needed to happen for a while. And it wasn't this bad, terrible thing. But financially, it was definitely a challenge. I was going through a period where I  left my career field. And in 2014, I wanted to take some time off. I did some consulting and freelancing. But really, I was burned out. And I didn't really know that at the time. I wasn't performing super well on freelance jobs that I was taking, because I was distracted by just being burned out and not wanting to do a lot of work, and traveling and learning and do a whole bunch of other things. 

And so going through that divorce process through there were things to separate and divide. And my ex had always made a lot more money than me. And she came from sort of a wealthier family. And so there was this natural tension that hey, here's this guy that doesn't really want to work and doesn't make a lot of money. It drove our decision to move to Milwaukee, and let me find the time to figure out what I'm going to do with my next couple of steps, career-wise. 

That created just a ton of tension. And so finally we decided that, hey, let's separate things out. And we tried to do that in a pretty amicable way. And eventually, some agreements fell apart. And then it just becomes this crazy thing. I don't have a lot of liquid cash, it's tied up in divorce proceedings, I need to buy the house from her. And I need to figure out like where that money can come from, you know, from a bank loan from the lender of the house that because we did a land contract for the house. So there are all these documents, there are divorce proceedings, there's a land contract for a house, there's my parents who are willing to help me get through this transition, so I refinance the house. 

So there's just this massive issue ($30,000 - $40,000) between my ex and I in relation to the house and if I wasn't able to secure that, I probably would have been forced to sell the house and, just by the nature of how everything worked out, I wasn't able to get a bank loan instantly. The timelines weren't working out so I needed to get money at one point. I needed to basically reassure her that I was going to get this money to her in a timely fashion. 

So that's one loan that she's basically giving to me that I need to get the money to satisfy that loan, but I needed to create a new loan for that and then I need to go to a bank and get a new loan to like satisfy that. So there's like three layers here and only one has an official process right and that's getting a loan from a bank.


Next let’s hear from Vicki Wusche, a Financial Strategist, who came out of a bad divorce, and also used her mathematical skills to become an expert in managing money!


Vicki Wusche: When I first met my first husband, or now my ex-husband, I was very naive. I had come from a family where we didn't talk about money, but I was aware of my mom's ability to save and to plan because when we had a holiday, she would buy things in advance for the holiday and stack it all up.

And I think I've either got either a, I dunno, like a genetic math skill or, if it's not nature, it's nurture. A nurtured understanding of money and planning and budget from observing my mum, but none of it was conscious. So I got into this relationship initially and moved into, at that time, my boyfriend's rented accommodation.

So of course he was paying all the bills so that when we got married and we bought our own house with a mortgage, I just assumed that he was paying all the bills again. That is the biggest mistake you can make in any relationship or anything to do with money is to assume. Never assume - understand absolutely everything.

And in the very first house we were in, it turned out we hadn't been paying the mortgage. Don't know why, he just didn't. And then my husband lost his job and then we couldn't pay the mortgage. And we managed to sell that house out from under the repossession. We then got into a second property and in the second property, somehow he did the same thing again.

And I look back at myself and I want to shake me or slap me and go, “What were you doing? What were you doing, Vicki when this was going on?” Well, one of the things I was doing was breeding and growing our baby. And the second time we were repossessed, I was seven months pregnant, and that caused me to have preeclampsia high blood pressure. And our baby was born early and I left one house literally with packing boxes because we couldn't get rehoused until we were actually evicted. And eviction means all your possessions have to go on the actual common pavement where people walk outside the property because they want you off the property before you can get something else.

And somehow in the miracle of the 10 days, I was in hospital with high blood pressure and everything, my now ex-husband managed to find a rental property and we moved in. So I left one house and then arrived at another house with a new baby. And we were bringing that child into a house that was bankrupt, that was repossessed, that was in loads of debt. 

We had some family, friends helping us out, but outwardly, if you hadn't been the person I'd asked to borrow money off of, we were having great holidays. We had a great car. We had the mobile phones, we would still go out for meals, so the trappings were all there and that's really where sort of ego comes into it and plays a role in the story.


Dan Narcisco, an expert in litigation finance, tells a super-awkward story about his friend who bought a house with his partner, only for things to go awry.


Dan Narcisco: Yeah. I mean, I've seen divorces, you know? One funny story, it deviates from work-life balance. But someone just kind of being dumb with their money.

I had a buddy of mine who owned his own house. You got engaged. And then he ended up quitting the property while he owned the property. He put the title in her name as well. And then they went five or six years through the engagement and then she got sick of it and kind of ended that engagement, but she was still entitled to the deed.

Yeah. So they were living together while they were broken up. And he ended up losing half the house after two years because of that mistake, you know? And so he's fine now, but he still lost half his house just because he decided to just put his house in someone else's name for vanity's sake.

Cameron Laird: Why do you think that is? Obviously, if they had gotten married, would there have been worse implications? Obviously, there'll be alimony and things like that, but do you think that he just simply jumped the gun as in, he essentially put his girlfriend on the lease of the house instead of what he thought was his future life?

Daniel Narcisco: It wasn't practical, no. I don't think he ever wanted to get married. He got engaged because she kind of said, “Hey, we’ve been dating for 13 years, now we need to get a house”. And he was like, okay. And then she was living there. So he put her on the deed of the house, but it's one of those things where he bought it beforehand.

So it technically is not marital property once you get married. So he could have had the apartment to himself, even if he got in there. But the fact that you want another five years without getting married and then got separated. And then she was living in the house and bringing guys over through the house because she said, “This is our house!” They were just like roommates. Not a great situation for them.

Cameron Laird: And he stayed there as well?

Daniel Narcisco: Yeah, he didn't, he didn't move. He was like, “I paid for this house. I'm not going to go anywhere.”


Entrepreneurs, start-up founders, and CEOs have all featured heavily on The Chirp, and for good reason! These individuals know what it’s like to live frugally. The early days of starting a company are not where you get to live your best life. It’s an uphill battle financially and sometimes you know when to ask to for help!

First, let’s hear Chris Daniels, Founder of the Shrimp Society, about one of his first entrepreneurial ventures, a lawn-mowing business, and how a family loan can be done right!


Chris Daniels: So, right when I turned 16, I got like this old truck and I wanted to pay it off right and start making money and things like that. And so kind of the precursor to Mulch Maniacs was this landscape business called Morning Dew.

And I wanted to get a riding mower, right? Like one of these nice riding mowers cause I was like, Hey, I need to be efficient. I'm cutting 10 lawns in my neighborhood. And I just wanted to drive this thing to the neighborhood and blah, blah, blah. And so it was like $2,000 and I didn't have that money.

I think I had a hundred dollars to my name and I was 16 and I remember I asked my Dad and my two grandpa's on either side, both very business-oriented, entrepreneurial people. My Dad, not at all. He's a doctor and just not a business guy. He doesn't like it. And so he's like, “Okay, well come pitch me, present something!”

So it literally went into the living room, formal pitch, the whole nine yards, printed out everything and asked for this $2,000 loan. And I think the interest rate was like 10% and I think it was supposed to be paid back in six months, right? Because I had my whole financial projection of we're going to cut lawns and make this profit, blah, blah, blah.

And we signed the contract, we wrote it up. We documented everything. And, looking back on that, I appreciate how formal he made that versus just like, “Hey dad, can I borrow $2,000?” He made me earn it, like let's be serious about it and there's consequences and things like that.

And I thought that was great. And so we went, and it was a fun moment. We went and bought the lawn mower and all that stuff. And then I remember like a week later we needed a trailer because the business was expanding and I had to go to another neighbor. So again, I had to go back to the shark tank pitch room and pitched him on another loan for a like $850 trailer.

And then we added that to the contract and that went through and paid everything back. And so that was kind of the start of it. And I think that having that base of family or friends, we can get into a ton of other stories, taking out bigger loans for family and friends, stuff like that for businesses, but specifically around entrepreneurship.

It's interesting because that's really how it starts. Someone's going to lend you money based on your character and the fact that you're going to deliver and they know you. And I see like all these people in the venture capital world raising like millions, hundreds of millions of dollars, right, or millions of dollars and doing it over zoom calls. 

They don't know the people. And in the early days, it's really when you're trying to go zero to one that $10,000, $50,000 a hundred thousand dollars is huge. And who's going to be the first people you ask? The people around you that trust you and you trust them and things like that.


Josh Barker, CEO of City Innovations Labs, knows what it’s like to start again in business, and when you go back to square one, certain luxuries are no longer on the table! Again, we see family come to the rescue.


Josh Barker: 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?


Unique stories are one of my favorite things about The Chirp. I love when a guest comes on and gives me a story to really chew on. Keith Moore, AKA Mister Credit Banking, is a content creator who shares tips and tricks on how to best handle your personal finance. Speaking about his own story living paycheck to paycheck is an inspirational story on how to improve your situation by educating yourself, and then educating others from your experience.


Keith Moore: So, probably about six years ago, I lost my job on my birthday. Congratulations! Happy birthday, you have no more job. Which was a horrible thing for me. And that was an eye-opener for me, because up until then I've always had a very good paying job, but I live paycheck to paycheck. And so I’d get paid on Friday and by Monday I was broke again.

But for me, it wasn't a big deal because I got paid weekly. So basically five days later, hey, I would have another paycheck. So, I survived. On the outside, nobody could tell that I was really struggling because every seven days I had a paycheck. So when I got laid off, I didn't learn my lesson.

I continued to live my regular life like I did have a paycheck. But anyways, I was surviving off of unemployment, which was basically half of what I was making. And so I could not make my mortgage payments. I could pay all my other bills, but I could not make my mortgage payment. And the other bad thing that I did is I did not have any type of emergency fund.

I didn't have any type of savings. I was truly living paycheck to paycheck. So, I just stopped paying my mortgage. And for three months I didn't have a job. It was three months of not paying my mortgage. So guess what? When I finally got my job, three months at my new job, three months later, I was three months behind in my mortgage and I was like, “Wow, I'm in a mess here.”

So I had to come up with a plan and it took me about six months. How was I going to get caught up in my mortgage? And so basically I got a side hustle, I got a job as an Amazon delivery driver, and that was going to help me get caught up on my mortgage. And it took me about two years to do that.

So in those two years, I have another 24 late payments. Although I wasn't falling behind. It took me two years to get caught up. And it took that long because life is still happening and emergencies are still happening. All these things are happening while I'm still trying to get caught up. And in between that I had a car that I was using to be a delivery driver for Amazon.

That car, because I was using a lot making deliveries for Amazon, it would break down a lot. And so, I still didn't really learn my lesson as it comes to personal finance. So whenever the car would break down, I just whipped out one of my credit cards, repaired it and I was on my way. I didn't really need to worry about paying the bill in August, I made the minimum payments on my credit card bill.

So, over those two years, to get caught up on my loan, I maxed out those credit cards and then, just my bad luck, guess what? The car broke down! So I have a maxed out credit card. It doesn't work and I'm slowly getting caught up on my mortgage. Things can't get any worse. So then I go to the car dealership and I say, “Hey, I have a broken car, I’m behind in my mortgage and I have maxed-out credit cards. Can you guys give me a loan to get a car?”

And they said, “Sure, let me run your credit 14 times”, which I did not know that they were going to do. I thought, “Hey, I signed for them to run my credit.” 

They ran it, I thought they were running it once, but I came to find out afterwards that they ran it 14 times to find me “a better deal”. The good thing is I didn't leave the car dealership with a new car, but unfortunately my credit card ran 14 times. So it even made my credit even worse. And the old car that broke down, I still owed $6,000. So a payment from the old car for $6,000 and then the new car, $17,000, I'm in even more debt.

My credit is even worse and I’m behind in my mortgage, it's a mess. So I had to say, “Gosh, I got to find a way to get out of this.” So that's around the time I say, “Hey, I gotta do something differently”. I started doing more and more and more research on YouTube on the internet, and that's also around the time when I started my Youtube channel.

And I started getting serious, creating a budget, paying up my bills and so forth. And at the same time, create my content from my YouTube channel. I'm doing research and I'm paying off my bills.


And last, but not certainly not least, Rahama Wright, CEO of Shea Yeleen, tells me about her time in Ghana and the excellent Susu system that the women of the community have there.


Rahama Wright: Yeah, no, that's a great question. And what I observed is that for the most part, the women that were in the communities and in the cooperatives that we were partnering with were head of household. There is a common practice of polygamy.

And so even though they might be married their husbands might not be living in the homes, but because they have multiple wives. And, and also the financial burden of caring for multiple false families. So I honestly saw a frequently Oh, a woman would be in charge of her household.

She'd be the one taking care of the kids and trying to figure out, you know, how to pay for their needs. And so part of the reason too, is this issue, or this misconception that, you know, men are going to get upset or, you know, have jealousy or not want their wives to make any money. I just never saw that.

And I'm sure it exists. You know, of course, I don't know every single family, I'm sure it exists, but for the ones that I saw firsthand, I did not see that challenge or issue. And so when you talk about this relationship with money and how it shows up in the community, the other reality is when women have increased access to income, it's been proven by studies that it improves the entire community.

And so there's this very special relationship and opportunity to address systemic issues. By financially empowering women. And so, you know, that relationship is, is closely tied to when a woman has money. She's 100% investing that money in her children. She's trying to figure out how they can get to a better school, how she can pay for better nutrition for them, and give them access to health services.

And I will also give an example of how the women in our cooperatives, they call them Susus, and essentially it is a community savings and lending program. And so that increased income also trickles to other people in the community. And so if you're a part of the Susu and you put money into the pot, it rotates in terms of who actually has access to that pot.

And because the community is. Small there's a responsibility to deliver, so you can't take money from the pot and like not pay it back when you're supposed to. So there's a certain level of trust already that is built into that community. And so when we see our women in the community, in the cooperatives that we work with, when they get that five times multiplier, it's not only affecting their household but affects other households in the community.

Outro Monologue

Those are all my favorite clips of The Chirp thus far. Again, I wish I could have played them all but we would be here all day. My main take-aways from the last 19 episodes are as follows:

  • Family is so important when it comes to loans. While it can sometimes lead to arguments and awkwardness, there is no better support structure available for those who need financial help. 
  • Systems are essential when it comes to paying loans back. Unless you are willing to part ways with your money, comfortable with the fact that you may never see it again, you lending that money without a system in place is a recipe for disaster. 
  • And finally, loans are imperative for aspiring entrepreneurs. Whether it's for your business, or just to feed yourself, It’s extremely difficult to be a successful entrepreneur without asking for help.

I want to finish by saying thank you to you all who listen and watch The Chirp. While we’ve 20 episodes in the books, we have no plans of slowing. We want to continue to bring you compelling, educational conversations from professionals who have made mistakes so that you don’t have to make them. Thank you again to all our amazing guests who have come on the show so far. No doubt some will be back again and I can’t wait to bring you more amazing interviews. 

As always, if you want to join me on The Chirp and tell your own story, please reach out to me. I’d love to talk. That’s all for this week. We will be back in two weeks for another episode and, until then, I hope you all stay safe and enjoy your summer. Take care, everyone!

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.