Story 19: Trust & Support Are The Keys To Success

Cameron Laird

Cameron Laird

Published on: 08 June, 2022

Updated: 01 December, 2022

Jon O'Bryan

Bad Debt, Theoretical Cosmology & 13 Siblings

We're back again with another episode of your favorite podcast - The Chirp. Like we usually do, we'll catch you up to speed first on what you missed in our last episode. Last conversation we got the chance to talk with "jack of all trades", and self-proclaimed fractional COO, Jèrèmy Chevallier! A master of his own work, Jèrèmy guided us through numerous stories of how mixing money with his own relationships went utterly wrong in some of his life's most critical moments. Take a listen to Jèrèmy's episode Story 18: Disappearing Money & Trouble With The Law before jumping into our conversation this week.

Our story this week comes from a startup founder, Y Combinator alum, and innovator in his own right. Jon O'Bryan is the CEO and founder of Atlas, a wildly popular customer support tool for businesses across the startup ecosystem. Before his claim to fame, Jon built up quite the track record. A PhD in Theoretical Cosmology, a 4-time startup founder, an engineer, and a family man, Jon has pretty much seen it all, and ironically enough, has had to depend on familial help quite a few times to finance these life successes. Lots of amazing soundbites in this one - enjoy!

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This Episode In A Nutshell

There are only a few things in this world more powerful than the words trust and support. We trust our friends and family to have our backs when times are tough and rely on the support of our community to make it through life's challenges. Our guest this week, Jon O'Bryan is no stranger to either of these words. Founder and CEO of Y Combinator-backed startup, Atlas, Jon has a PhD in Theoretical Cosmology and is a 4-time success in the world of startups. Even with all of these accolades under his belt, over the years, Jon has relied quite heavily on his trust in others and the support of his loved ones in order to achieve much of his success. Supported by his father, family, investors, colleagues, and more, you'll come to learn by listening to our conversation with Jon, that everyone, no matter your achievements, at some point will have to call upon the help of others to get through life.

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Audio Transcript of Story 19: Trust & Support Are The Keys To Success

Opening Monologue

Hello everyone welcome back to another episode of The Chirp: A Podcast By Pigeon. We talk to interesting guests from all walks of life about their relationships with people and money and how they are oh so intertwined. 

My next guest is a gentleman who is now currently on Startup #4 as a Founder and is leading the way in customer support with his company Atlas. I always love to pick the brains of successful entrepreneurs like Jon as being an entrepreneur is no cakewalk. There are always financial obstacles along the way, both personally and professionally, and Jon was no exception. 

I also got an insight into his thoughts on customer support as a whole and the future of that industry and, after an unfortunate banking experience myself last month, I wanted to learn more about support within Fintech and, when it comes to our money, how a solid customer experience is beyond valuable for both company and client alike. 

Stick around 'til the end to hear about how to get in touch with Jon if his words of wisdom resonate with you. I hope you all enjoy. Let’s dive in.

Cameron Laird

Jon, thank you so much for joining me today on The Chirp. It's great to have you here. How are things? 

Jon O'Bryan 

Yeah, going really well!

Cameron Laird 

Good to hear. Jon, obviously I know you through the Pigeon gang as the CEO and founder of Atlas, and, but obviously checking out your LinkedIn, it was cool to see the other roles you've had in the past.

And before we get into stories that you might have about your relationships being affected by money or by loans, I'd love to hear about your life story thus far if you wouldn’t mind.

Jon O'Bryan 

Yeah. So really really briefly, I grew up in rural Kentucky, a town called Possum Trot, Kentucky. I was there for most of my childhood, a pretty big family.

My mother and father had nine kids together. And then my dad got remarried and had another three. And then that marriage also had one coming in and they adopted another. So I've got wow, whatever that is. I think I've got 13…

Cameron Laird: 

13, 14 siblings?

Jon O'Bryan 

Yeah. 14 of us total. I think. Yeah, so we're a tons of kids!

I'm number six of that batch. So grew up mostly in rural Kentucky, moved out to California, to do an undergraduate and then did grad school in California as well. Did a PhD in physics, in theoretical cosmology. In the middle of that, I spent a couple of years out in the UK, in Scotland.

And then moved to Atlanta, Georgia. I worked as a quant very briefly and then as an engineer briefly, jumping into the startup world and I've been an entrepreneur for the last eight years. So, a few different things. I won't go into all of them, but a few startups ago I did short-term rental property management, and then did that for a few years until I discovered that property management is incredibly difficult and difficult to scale, especially from a technology standpoint.

So then. Jumped into my last startup, which is a company called PadSplit, where we were building Airbnb for affordable housing. So I co-founded that and worked as a CTO for about three and a half years before starting Atlas. I worked with folks who were low-income individuals, typically singles, sometimes couples, who were in the bottom 30% of income earners.

And so these were folks in service industries and really like the lifeblood of what you need to keep the community alive. So bus drivers, servers, warehouse workers, teachers, police officers. So, I did that and so that was all about helping people find stability in their lives so that they could level up financially. 

There were really moving stories about how people were able to make changes in their lives because they were able to find stability through what we were providing. And so, in the process, I discovered that customer support is an incredibly important piece of what we were doing at PadSplit.

In order to grow the marketplace and really make a big impact, we needed to figure out customer support. And this was from both a process and tooling standpoint. And so I dug in a lot there. And what I learned essentially is that there were plenty of processes that we could improve and implement best practices.

And then there were also, tools. And so I explored all of the different tools that were available and discovered that there was sort of like a brick wall that we were running into. Fundamentally, our customer information was fragmented across lots of different locations and that made it really difficult for support agents to be able to serve our end-users to deliver on our mission.

And so, I got to talking to some friends and was introduced to my co-founder, Rahul, who had dealt with this problem very intimately for several years at his prior two startups. And, we got together and said, “Hey, let's essentially make some software to solve this problem.” And that's what Atlas is: A system of record for customer support.

Cameron Laird 

And before going to go into your own stories, I'm keen to explore during your time helping people with affordable housing as well from a financial standpoint. What were some of the main reasons or some of the main customer queries you would have come across or some of the main drawbacks you hide from people facing this type of crisis?

Jon O'Bryan 

I think a lot of folks that are Pigeon users would fall square in the middle of our customer base. Fundamentally, here's the problem. The cost of housing is going up much faster than the average income, especially for the lowest-income earners.

So for the richest folks in the U.S, their incomes are moving up very well. For the folks who are called “The bottom 30% of income earners”, their income stays mostly flat while housing costs have risen a ton. And so what this means is there's a greater and greater strain on folks financially to be able to find just the basics of life, like a place to lay down and call their own, et cetera.

And so as a result of more and more financial burden, folks end up running into these walls where they can get housing and need help financially. So they need to be able to make the quote down payment on… 

Even an apartment to rent. There’s the first month's deposit, plus last month's deposit, plus the application fee. $2,500 to $3,000, I think, is the average for all that combined in the US, and most folks don't have $2,500 in their bank account floating around. 

So between that and the fact that there are these onerous earnings to rent ratio that's needed, specifically three to one. And then on top of that, you need a pretty good credit score. And so those three things combined make it really difficult to find a place to stay. And so we try to alleviate some of that burden. But even with that burden, we saw a decent number of people who, because they're living basically on razor's edge, there are many times when they need financial help, and need to reach out, whether it's a friend, a family member a community or support organization that they need that help. To be able to get over the rough patches if they lose their job or didn't get enough hours because they were on sort of a seasonal job, et cetera.

Cameron Laird 

And during your travels to the UK and studying theoretical cosmology, I wish that we could do an episode of a podcast about that alone, that's that sounds very exciting. But were there any times where you did ask for help or you had friends and family to reach out to financially to lean upon?

Jon O'Bryan 

Yeah, absolutely. Quite frankly, I think I'm not any exception here. In undergrad, I needed help paying for college and had to take loans out from family members, from my Dad primarily. And then there were times when during summers or between undergrad and grad school where I needed like a couple hundred or even a thousand dollars or a couple of thousand dollars to kind of float between student aid and earning an income as a graduate student.

And so, yeah, absolutely. You know, very fortunately there was a safety net, but it was always a very awkward conversation for me to say, hey, you have to ask for the money, then structure the repayment. It's super, super awkward and who keeps track of it, et cetera.

Cameron Laird 

How did you keep track of it? Did you have any systems in place or did you just wing it and say, “Please trust me. It's coming back.” ?

Jon O'Bryan 

Because, just that! Yeah, it was the just wing-it thing. My Dad's, for better or worse, he's an incredibly good bookkeeper. And he knew every penny that he had loaned me, and he kept track of that with, with interest. And so in some regard, fortunately, he was very good at keeping track of those things, but from my perspective, a little bit of a black box and frankly, a little bit scary to think about.

And, and also because he kept track of the money that I owed and the interest that was accruing, but we never worked out any like never an advanced payment plan. So I had no idea what the burden would actually look like. Very fortunately it was a familial and friendly relationship and I was able to float it for a long time.

But frankly, it has at times put a strain on our relationship, even a father-son relationship, and I think honestly if we had had the conversation up front and set a precedence of whatever the payment would be in a repayment period, missing one payment here or there because of strenuous circumstances, it would have been less stressful than getting to the end of some period of feeling like, okay, there's this massive lump sum, I need you to start repaying it sort of thing. 

Cameron Laird 

Well it’s not an easy thing to do as well if you do take a loan during the early stages of your college life or something like that. And to have to look forward so many years when it actually will be possible to pay it back.

It's a tough thing to do. And speaking of your college years you studied Theoretical Cosmology, am I saying that right?

Jon O'Bryan 

Yeah, that's what I did for my PhD and I did math and physics for my undergrad. 

Cameron Laird 

Amazing, and how do you move from that into becoming a really successful entrepreneur and running all these startups? What were the transferable skills? 

Jon O'Bryan 

Being able to break down problems and then being able to keep beating your head against a problem until you get to an answer, are transferable skills. And basically, that was my life with both math and physics.

Just lots of really gnarly, hard problems. And you have to keep thinking, keep thinking, and try a whole bunch of different things which ends up taking lots and lots of time. You asked your friends, you read a bunch of different sources to try to figure out the problem. And then at the end of the day, you've got a deadline, you've got to turn it in.

So you give it your best shot. I think one of the big differences is at the end of the day, if you don't like a course or whatever, there's typically a definitively correct answer and there's a deadline and you can kind of move on to the next thing. Whereas with startups there's not a definitively right answer almost ever.

And the deadline is a pretty grim one. It's basically your company going out of business. And so it's not as easy to sort of like wind it down and you have to power forward. 

Cameron Laird 

From an entrepreneurial perspective as well and in your later life, were there more recent stories where relationships have been affected by money loans from a business standpoint or something more in your adult years? 

Jon O'Bryan 

Yeah so actually two startups ago, one of the reasons I was highly scared of the the other startup, this property management startup that I was a part of, at one point we had to take a loan. It was this is a business loan. We weren't able to raise venture capital and so we were trying to prove things out manually. And so we took some loans that were like usury rates, but the type of loan and the language that they put it in, I guess, made it legal.

But these were loans that had like 17% interest per year or something. So like incredibly burdensome to pay back. And whenever I was going into it a little bit naive, I was like, “Oh, we can make that up. No problem.” But when you're in a business that's sort of a 30-something percent gross margin business, that eats into your earnings a lot.

And so we took a couple of these loans and they had to be personally guaranteed. And that was the scary thing. If the business went under, there was no “We're good to go”. It was basically my neck on the line.

And so we did that a couple of times and it was incredibly scary because we ran very close on those and basically threatened the existence of the business. What it did teach me is you need to be incredibly aware of what the interest rate is on your loans and how feasible or not feasible it is to pay those back and look for alternative ways of growing or finding money by savings as opposed to finding money by debt.

Cameron Laird 

Going back to your entrepreneurial journey and trajectory, what advice would you give to someone starting out or maybe those that are starting something off, but maybe don't have the financial stability to live the comfortable life that they feel that they deserve? What advice would you give to other entrepreneurs? 

Jon O'Bryan 

I think the biggest thing in my mind is if you want to go work at a startup, that's awesome. I would encourage anyone, who wants to do it, to do it, but also you need to realize what you're getting yourself into.

Like, it is not an easy life. It is not the life that you think you deserve to live. Quite frankly, as an entrepreneur, you are willingly and knowingly walking into a lot of difficulty and pain. So you're not going to have the hours that you would have at a normal job.

You’ll have many more hours you'll have much lower pay. You won't have the vacations, you won't have the benefits, et cetera. And you're doing this hoping for some upside. But then also there's a lot of value personally I think in the experience of being able to potentially contribute in a really big way in the world.

And so, from a financial standpoint, what I would say is learn how to be incredibly frugal. Think about what is the absolute minimum you need to get by from where you're living, like what you're eating, what you're doing, and how you're spending. And that's really what saving is.

In order of preference, I would say you can save money, you can take debt or you can sell parts of your company. Well, getting those parts of your company back, you can't really do that. That's very, very difficult. Debt is preferred to that. But the best way is really just lower your costs and find ways to do more with less.

And you need to analyze everything. You know, line-item expenses on your bills and find out ways that you can lower those costs or remove those costs, and get really smart. And I think that's where you can find a lot of joy, quite frankly. It's like, you'll learn to find joy in life with fewer things.

And, so maybe, maybe not like a great answer, but I think ultimately, that's where you need to have your mind. 

Cameron Laird 

Brilliant, Jon, and can you speak to the importance of customer support when it comes to financial companies and financial institutions? Like, do you have any clients in this area, and what are some of the main characteristics of dealing with customers in this area?

Jon O'Bryan 

So whenever you're dealing with financial tools or transactions, fundamentally you have someone's money and they're entrusting you to make sure that you either hold their money or get their money from one place to another safely and in a high-integrity way. And so trust is incredibly important.

Security is incredibly important. People don't like shenanigans, they don't like not having answers. And so what we've seen is really important. Basically, you need people to believe that you're competent, that you know what you're talking about whenever it comes to what's going on underneath the hood, and can give them straight answers about where their money is.

Why it's in one location or another, why transactions failed, things like that. And one of the best ways to do that is really to deeply understand that customer and their interactions with your platform. And so that's something that we seek to provide it with Atlas, and I know lots and lots of FinTech companies try to do is make sure that their payment rails systems are set up seamlessly, go through tons of checks to make sure that they're very robust. They typically don't try to do things that are super complicated because that can remove trust whenever someone doesn't understand what's going on.

And so I think the best way is basically have a solid system. Don't make it too complicated. And then know exactly what your users are doing and are trying to do. And so the way that Atlas approaches that problem is we basically show you everything that they've done through their eyes, so that you can be incredibly empathetic, because you're actually seeing everything they're doing as if you're sitting over their shoulder, as opposed to trying to ask them lots of questions about what they were trying to do, where they're at, et cetera.

What we've seen is that whenever you talk to support, say at Amazon or wherever, and let's say you can't check out your in your Amazon cart, you can’t check out for some reason, if you go and talk to a support person, say, “Hey, I can't check out.” It would inspire trust if they said, “Oh, well just do this thing.” 

Great. One question, one response, you're on with your day. Especially if that thing works. Of course. What does not inspire confidence or trust is whatever they have to ask you 20 questions about what you're doing, right.

What did you click on? What's in your cart? Did you press this button? It feels like any random person off the street would ask you these same questions. And so it feels like they've got no special knowledge either about necessarily the product or especially about your particular instance.

And that's something that we don't think that in 2022, you should have to deal with that as a customer. And frankly, no company should be providing that sort of poor quality support where they're making you as the customer do their QA work.

Cameron Laird 

Yeah, because there was something I wanted to ask you. My girlfriend got her bag stolen in Barcelona there a couple of weeks ago, a horrible experience. I'm surprised we lasted this long in Barcelona as we've been here a year and it's something that happens to other people a lot sooner. 

But she lost her Irish bank card and then she also lost her Revolut card. The disparity in customer service and customer support was mind-blowing. The way that the Irish Bank had to send out letters or card replacements and PIN replacements.

And then on the other hand, she's getting onto Revolut, which is like Venmo or CashApp or something like that. It's very big in Europe as well. And it was all sorted within seconds and there was a new card sent out within minutes. I’d love get your take on that from a customer service perspective.

Why are some people living in the dark ages when it comes to mobile banking or financial transactions, and then there are other mobile banks that are just so ahead of the curve?

Jon O'Bryan 

Yeah, I think, fundamentally, it's sort of because nobody wants to break trust. Once they get it, it's very hard to fight for and to establish it. And so, as a result, people become super averse to change. They don't want to update their processes or the tools because they're worried that it'll break things. And quite frankly, it's expensive to do that many times. 

And so there's sort of this old guard, and this is the same whether it's FinTech or other tools. Many times people get established in their trends and tools and patterns, and they find something that's working, not, not realizing perhaps that something that's working isn’t always ephemeral.

There's never a golden solution to any problem and, in FinTech especially, you'll always have to be updating your processes and your tools to stay at the forefront of quality, service, and quality user experience. And so this old bank in Ireland is probably got some outsourced support team, who has a set script and a whole bunch of processes because they wanted to cover every possible use case in there and haven't upgraded to newer technology. 

Whereas Revolut had the advantage of starting more recently and they can use this newer technology because they have more trust in it and more knowledge of how it works. And as a result, they're able to provide a better experience all the way through.

And I think that's fundamentally it. Is the Revolut product better than the Irish bank product? I'm almost certain the answer is yes, but the reality is you also need a better support experience in order to have that trust because things are gonna happen, like the unhappy path of someone stealing your card or whatever the scenario is. 

And you've got to eventually hit a human, and that's where you want to make sure that your support experience is robust so that people… like if I ever moved to Europe, I know which bank I'm getting an account with based off this conversation. And that's why Revolut is huge and growing rapidly, and this Irish bank is probably barely growing.

Cameron Laird 

Yeah, customer support for me is such a huge thing when it comes to money. And the story you just told is a prime example of that, but it’s just the ease of use as well.

And all Irish banks are not all bad, but just when you see these new mobile banks coming in, like Revolut and N26, like Venmo as well, just this ease of use for swapping money and sending money, it's such a game-changer for me. Well listen, Jon, if people want to find out more about you or Atlas, where can they find you? Where can they get in touch? 

Jon O'Bryan 

They can go to our website and, or you can email me directly, We'd love to answer any questions or learn how you're doing support today and frankly, I’m happy to offer advice or my experience. And I believe Atlas is the tool support teams need to improve their support experience.

But frankly, if it's not a good fit for one reason or another, I’m happy to have this conversation. I believe deeply that support teams need to be elevated for products to get better at solving customers' problems and just making the world a happier place.

Cameron Laird 

Fantastic. Well, it was great hearing your experiences, both professionally and with your relationships been affected by money and loans. So really appreciate you sharing your stories with me today and giving me your time and best of luck with everything with Atlas. 

Jon O'Bryan 

Awesome. Thanks so much.

Outro Monologue

A man in the know. Jon is no stranger to loans to stay afloat. While his Dad lending him money during college is something with low risk, it was his business loan with his 2nd startup that seemed strenuous. 

To have a loan threaten the existence of a business from interest rates is very risky and something I’m sure Jon learned from a lot. Heed his words of warning when he said to pay attention to interest rates on loans! Do not be lured in by the attractive prospect of having a lump sum of money alleviate any financial pressure only to have the amount you’re actually repaying be a lot more than what you planned for. 

It was also great to hear his thoughts on customer support in the FinTech area. As you heard, my girlfriend lost her bag with everything in it, including all of her bank cards but, thankfully, excluding her passport. 

The two conversations with the two banks, our retail bank and our mobile bank, were highly different and it begs the question, what does the future of banking and financial transactions look like?
The retail bank had us talking to 5 different advisors, all asking the same questions at the start and giving a 1 step forward, 2 steps back kind of feeling. The mobile bank had everything sorted in minutes. Which sounds better from a consumer’s perspective?

Hosting this podcast, chatting to people like Jon, it all opens my mind to the financial options that are out there and how the future of fintech is bright for those, like me and my girlfriend, who have been living through the suffocation of old school systems and processes that a simple smartphone seem to cancel out. 

So. My main take-away? Customers of fintech can be excited about the future and not be daunted about “powerful” financial institutions. Whether you’re sending money, saving money, or lending money, it’s all just a click away. Just how it should be.

We’ll be back in 2 weeks for our 20th episode of The Chirp. What a monumental milestone for The Chirp and for Pigeon and for educating you all on money and loans. We thank you for watching and for listening. Do reach out if you have some stories to tell. Until next time, stay safe!

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.