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Giant Robots Smashing Into Other Giant Robots

504: Spare with D'ontra Hughes

December 14th, 2023

D'ontra Hughes is the Founder and CEO of Spare, which uses tech to solve cash management problems for unbanked small businesses and enterprises. D'ontra shares his entrepreneurship journey, driven by realizing the financial industry's impact on less privileged individuals.

D'ontra highlights a significant issue in the banking sector where the poorest people are often charged the most in fees, perpetuating poverty. Spare addresses the high fees unbanked individuals face when accessing their money. D'ontra's entrepreneurial journey involved various challenges, including learning from customer feedback, understanding the importance of data-driven decisions, and navigating the competitive startup environment.

The conversation also covers the impact of the COVID-19 pandemic on Spare, leading to a strategic shift and a focus on regions with high cash circulation. D'ontra emphasizes the importance of strategic planning, data analysis, and a systematic approach to business growth. He also discusses the personal aspects of being a CEO, stressing the importance of maintaining personal relationships and self-care.


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Transcript:

VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. And with us today is D'ontra Hughes, Founder and CEO of Spare, which uses tech to solve cash management problems for the unbanked small businesses and enterprise. D'ontra, thank you for joining us.

D'ONTRA: Well, thank you for having me.

VICTORIA: Well, wonderful. So, we met at San Diego Startup Week a few weeks ago. So, I'm excited to have you on the podcast today. Why don't you tell me what was your experience of San Diego Startup Week? And how did you come to be one of the speakers on a panel there?

D'ONTRA: Yeah, well, it's always a really nice thing to take part in, you know, kind of those innovative startup week events because you get to see a lot of what people are working on or what they're doing. So, we've been working very closely with the County of San Diego, especially with the city of Oceanside with our latest technology.

And, you know, there came this opportunity where I could get on the stage and kind of tell people about our journey a little bit, I think because we're becoming a little bit more successful or something [laughs]; I don't know what to say. We're getting better at what we're doing, apparently, and so folks wanted to hear what I had to say.

VICTORIA: I was able to catch your talk, and I thought what was really inspiring about it was that you came from the background of working in the financial industry and saw an opportunity to solve a problem that was common for other people and to be more fulfilled by the work you were doing. So, can you share a little bit about that?

D'ONTRA: I came out of a background in finance, as you said. I used to work for JPMorgan. It feels like a long, long time ago. And that was my last corporate job until I became an entrepreneur. You know, one of the things that I learned at that time...and not that the bank was doing anything wrong, but in the nature of finance, it's a business, right? It's got customers. It's got clients. It's got shareholders. And the most important thing is it's designed to make money.

There's always someone that loses, right? And sometimes you could say that that's the nature of business. But in this regard, it was a lot of people who lost that couldn't recover or wouldn't be able to recover from the financial waste that was left.

You know, I went on my entrepreneurial journey wanting to learn how to build a business and, you know, try to solve problems for myself or for other people. And specifically for this endeavor with Spare, which we launched back in 2015, we looked at the subset of the population, roughly about 25% of the U.S. population, 90-something million households of folks that were basically spending about 7% of their own income every year just accessing their own money. And, like, that's wild, right? Because if I came to you and I said, "Hey, if you got 100 bucks in your pocket, in order to pull that money out of your pocket, you got to give me $7," you'd be furious.

And so, the unfortunate thing is that this kind of tax on the poor was being facilitated by the ATM industry. At the time when we began the company, you had consumers out there going to an ATM roughly about seven times per month, withdrawing roughly about $60 per transaction. And the average fee at that time was $4.09. And today, the average fee is just about $4.80, something cents, depending on where you're at in the country.

And so, it's unfortunate the difference in these fees for these folks. It might sound absurd to say this, but it makes a difference between eating and not eating for some of these folks. And anyone who's a struggling college student or lives on the low end of the economic spectrum they understand what I mean by that, where the extra $30 or $40 in their pocket per month actually matters. It's an extra tank of gas or two tanks of gas, depending on what kind of car you're driving. And so, it matters.

We wanted to really take a really clean look, an assertive look at the relationship that, not just the ATM, but just cash management services or cash management on a local level the impact that it actually has.

VICTORIA: Yeah. And to kind of play that back a little bit, let's say you have a bank or you're not able even to get an account in a traditional bank. Maybe your bank doesn't have an ATM in your neighborhood, and you need to always go to a different ATM to get money out of your bank. And you're just constantly paying those fees. You're more likely taking out smaller sums of money, and then you have to do that over and over again. And it becomes a really high percentage of your income that goes just towards getting money out of the ATM.

D'ONTRA: Yeah, absolutely. So, when you consider even during the pandemic, right? Everyone's at home, but businesses were trying to figure out how to cut costs. And banks, just like any other business, when they have a retail bank branch that's in a neighborhood that's perhaps low income, they may not keep that bank branch around. And that's unfortunate because it creates an additional hurdle for folks to be able to become banked.

You may hear this term of banking deserts, and that's partially because folks have to travel too far, which is an external cost of time, and money, and resources, just to be able to put their money inside of a bank. Now, the additional cost for this particular demographic is that fees tend to add up. And we all know that the bank says, "Hey, as long as you keep $1,200 in your bank account, we're not going to charge you any fees." Well, that's really great, except for the person who is living paycheck to paycheck, right?

And so, this fee tax that's placed on them simply because they don't have enough money when you look at it, it's actually pretty rough [laughs]. I look at it, and sometimes I kind of laugh because it's absolutely absurd when you actually look at it on its face where the poorest people you're generating the most profits from. And unfortunately, those fees keep them in the cycle of being poor.

And so, it's been really great. Over the past few years, you've seen really great applications or neobanks come up that have acted as, you know, somewhat shields against all of these arbitrary fees, like, hey, no overdraft fees, and no account fees, ever, no monthly fees, and things of that nature, right? But they still aren't solving the other issues, some of the major issues.

So, it's really great that I have your debit card. But if you're a neobank, that means I either have to use your co-op ATM network, which is only going to allow me to withdraw cash so many times per month for free, or I have to use some other third-party ATM network. The unfortunate thing about that is they're still paying that fee [laughs]. At some point, they're still going to pay that fee, and when that money is better in their pockets, it's just a little rough. It's a little hard to digest. And so, we wanted to make sure we were doing something about it.

VICTORIA: Right. It reminds me of a phrase I come back to sometimes is that being poor is actually very expensive [laughs].

D'ONTRA: It is.

VICTORIA: There's a lot of fees, a lot of extra stuff you have to pay for that other people don't. I'm curious: how did you narrow in on this problem? Was it through doing some market research? Was it a personal experience that led you to wanting to work for these types of users?

D'ONTRA: Even though JPMorgan was my last, like, corporate job, I went out into the world to be an entrepreneur. Being an entrepreneur is expensive because you got to figure out how to pay bills. And so, one of the side gigs I had is I worked for a hotel in Santa Monica by the name of the Fairmont, and I was managing valet. For anyone who's been to the Fairmont in Santa Monica, it's not for the cheap folks, right?

But what would happen is, you know, patrons would show up, and they'd say, "Hey, I'm going to valet my car. I'm going to come back and pick it up." I'm going to go ahead and settle this up. But, you know, where's the nearest ATM so I can give the valet person cash?" And the most often answer was, "Well, there's one inside the lobby of the hotel, and then there's one across this very busy street." Both of these ATMs had a fee of...the one across the street was about $3.75 if you weren't a bank customer, and, of course, it wasn't a national bank. And then the one in the lobby was about $4.75, I think is what the fee was.

And so, here's the person who doesn't really carry cash that often being told that they have to pay a premium just to help this person out. And you could almost guess what the most likely outcome was is, unfortunately, that valet person just didn't get tipped. But the thing is, is there was actually a third source of cash, and it was actually in the valet's pocket or at the valet stand. So, there was money there in closer proximity. There just wasn't a mechanism of extracting it.

And so, our first look was, well, hey, can we monetize a transaction between, say, the valet stand and this consumer where, basically, the valet stand is selling these folks their cash for much cheaper than the ATM? So, it's going to save everyone time, energy, money, and it ensures that the valet folks get cash in their pocket. I can remember when we initially launched this; I thought it was such a brilliant idea. We created an app in which we would populate a map with all the people around you that had cash on them. So, when you say it out loud, --

VICTORIA: [laughs] Yeah. I could see how that might be problematic.

[laughter]

D'ONTRA: So, we're super stoked. We're, like, "Hey, we got this app, and it's really great. And, you know, look at all the people here that have money on them." So, we go to submit this thing to the App Store, and the legal team's like, "Absolutely not [laughs]." So, we spent about six months working back and forth with their legal team to come up with a model.

And it's somewhat similar to what you see today, where we're sending consumers to regular brick-and-mortar businesses that have spare cash on hand. That's it. Nothing glamorous about that. But the mechanism and the usefulness does some real overall good, not just for the consumers but for the businesses and for the local economy.

VICTORIA: Right. So, I was going to ask you, like, what surprised you in the early phases: the discovery process? It sounds like you had at least [laughs] at least one big strategic turn. But I'm curious if there was anything else that came up in your early-stage journey where you realized you had to make a pivot and change up what you were doing based on the feedback you got from users.

D'ONTRA: I'd love to be able to tell the story that we got it all right the first time around, but we didn't. I think we almost hit the checklist of things that you should not do. So, like [laughs], one example is you actually really truly shouldn't listen to your customer to some degree, right? So, you have the vision for this thing, but every customer has their idea of how your app should be better or something you should add.

And we went through phases where we were adding features then that people just weren't using. You know, it might have worked for, you know, 10% of the user base, but we had spent two or three weeks with the dev team putting in this new feature. And it was somewhat of a departure from the core. It's adjacent, and so we could justify it. So, we did it, but we shouldn't have. So [laughs], then we had to, like, backtrack on that. We had lots of these moments.

But I would say one of the most defining moments, and it was actually one of the first ones that came, was this moment in which one of early entrepreneurs' fear is that someone is going to steal your idea. So, we try to, you know, wrap folks up in NDAs, and secrecy, and things of that nature. You know, if you have a really solid idea, like, we all know that it has major potential to change your life.

And so, I can remember, you know, we went out, and we pitched this business to a venture capital company. It was very early on. That was my first lesson: people don't steal things that are worthless. And the second being that just because they steal, it doesn't mean they can build it. I can remember, you know, it took us six and a half months to get Spare in the App Store the first time around.

And during that time, we had met with this venture capital company looking for investors, angel investors. And it happened to be that this company gave us an offer to buy the company, and we said "No." But then were like, "Hey, why don't you come in and consult us, and let's see if we can work together to do a deal?" And me being super naive at that time, went in, and I said, "Hey, yeah. Like, this is how we would change the app, and this is what we would do."

And after two or three hours chatting with them, I had designed my competitor. And I didn't know that until a week later where they made their announcement, and, you know, I had Google Alerts on. And so, this app comes out and, you know, they're posting to see what people think about it. And they had gotten their app in the App Store, same business model, mind you. And I was just blown away [laughs]. Like, I think, at that time, I think I lost all composure. I was, like, sick to my stomach. I was furious.

When you asked about, like, the major pivot, it would have been in, like, my mindset because I went in thinking that we have this really great idea and how could anyone want to take something from an entrepreneur because starting is tough enough, especially the people that fund this stuff, right? And [laughs] I learned that, no, opportunities are opportunities, and people take them when they can.

And the bigger you become or depending on where your industry is, people are just looking for a shot. They're looking for an opportunity. No one really cares whether or not they're copying someone else's tech, right? If you were destined to do it, you would do it, and you would do it well, and you'd be one of the top ones to do it, right?

That was a major change in how I saw this journey, which allowed me to kind of reframe what we were doing and how I was approaching the market, how we collected data, how we dealt with our consumers, and how we ran our business in general. And then, we had to go in and pivot back to the conversation around the customer. So, we go back, and we're going back to build this thing. And so, at that time, I'm feeling, okay, I have to, like, do any and everything I can once we're in the App Store to get users and retain them.

And that's when I learned the lesson of, like, don't listen to all of your users. Like, know what your thing is, and do that thing really, really well. And try not to build features that aren't central to your core because, honestly, that can just get you in a lot of trouble. And you can waste a lot of time for no reason.

But I think the most important thing out of that is listen to the data, the information, and what I mean by that is where people go on a webpage, or where they go in your app, where they spend the most time. Listen to those things, and pay attention to the data, and somewhat become obsessed about utilizing the data to make your decisions. I think that'll save everyone a bit of heartache and, you know, pain as they go down that journey.

VICTORIA: Yeah, I really love that. There's a couple of, like, interesting points. I feel like when you said it can be daunting, like, oh, there's a million apps in there that already do this or, like, somebody else has already started this. Like, sometimes that means, well, it's a good idea because clearly somebody was willing to try and put it together, and they found a market. But you can always do it better, and you can always have a unique angle and try if you think there's a strong enough idea.

And I'm curious to, like, get more into, like, the data question and understand what do you use to understand how people are behaving in your app? And kind of metrics you look at to see how you're tracking and whether those are, like, key success measures or other ways that you think about that data.

D'ONTRA: For our application, you know, our KPIs were pretty simple very early on. It was like, do we have, like, the keywords that people respond to to find the application? And is it cash? Is cash the keyword? Is ATM the keyword? How do people find us, ultimately, at the end of the day? Because if you can solve that, solving what keywords are most attractive to your company, then what you're going to be able to do is organic traffic is going to be a lot easier to come by.

So, you don't have to spend a whole lot of money trying to get advertisements. There's going to be natural search traffic that drive people toward your platform. In addition to that, it was really paying attention to where the customer complaints were coming from because that told us a lot about the application. Even still, today, we have one very consistent customer complaint that, like, the unfortunate thing is, like, it's really difficult for us to solve this thing because it's actually more in the hands of the business than it is us.

And that major customer complaint is when I went into this active location, the person at the cash register didn't necessarily know what I was talking about, and there's a myriad of different reasons for that. But the primary one is that these locations typically have high turnover for the person that's working at the counter. And so Spare has to be an integral part of their onboarding this person so that when someone walks off the street, they can get the service that they need.

To some degree, listening or paying attention to the feedback that you're getting about the effectiveness of the service or being able to deliver the technology is actually a very useful data point. In addition to that, looking at where your app is available in cross-section with where the people are that are going to use your app. And this is one of the lessons, I think, we learned the hard way, where, you know, we came out the gate and said, "Hey, anybody and everybody can use this app. It doesn't matter if you're in New York, if you're in Texas, Midwest. It doesn't make a difference, right? Any and everyone can use it."

And the unfortunate thing is, when you do that, like, you're going to new users, which is really fun. It starts off that way. So, you go out, and you get merchants and things of that nature. And the mentality that we used was, well, we'll build it. The users will come, and the users will tell us where the businesses are or where we need to place businesses. So, we had a new person or a group of individuals show up in downtown Los Angeles. It was like, okay, cool, there's a concentration of people in Downtown LA. Let's go make sure we put businesses there. Well, that's faulty thinking in and of itself.

Even though you're getting the data points and the useful bits of data, you're actually doing it in pretty much, like, the wrong order [laughs]. We didn't really realize that, and Spare was my first tech company. And so, you know, when you think about things like that, like, you think, oh, users, they're important. But how you get them, and how you service them, and when you service them must be a strategic plan. You have to have that process thought out so that the user audience follows your plan, not you responding to them or following their informal plan.

VICTORIA: Yeah, that makes sense. And I love that, you know, focusing on the users and really focusing, like, on all of their unique needs like location [laughs] and other things like that. And I talk about that, you know, in my role as managing director at thoughtbot, I work on our DevOps and platform engineering team. I often talk about it in terms of, you know, very early in the process; you know enough about your user to tell you a lot about what their needs are going to be like on the infrastructure side, like their regional location, the sensitivity of the data, you know, that can tell you a lot about what you need to build [laughs].

So, I'm curious, you know, you're working on a financial app here. Have you also had to consider that from a regional perspective and from an infrastructure perspective how that affects your users?

D'ONTRA: Going into COVID and how we got there, was that we thought we were actually doing really well, right? So, we officially launched our platform to the marketplace in Q4 of 2018. And we did well for the initial launch without any marketing. And then a year later, we had done 3x the volume and had a strategic partner in place that would have grown our network by 30 times by the end of the next year, you know, we were moving.

And then COVID came along, right? In which, you know, huge event that no one planned for. It kind of put the company on halt while businesses were shut down, and we lost about 98% of our network at that time. So, we had to go back to the drawing board and kind of, like, figure out, well, one, if this company is really truly something that we know that there's a thing, we're going to continue to build it, but let's do it better this time around, like, what did we miss the first time?

And the first place that we went when we were trying to make this decision is we went to look up, like, cash effectively, like cash in circulation. And to our surprise, actually, there was more cash put into [laughs] circulation during COVID than there was at any other time in the past, like, decade, and so that was shocking. And so, we said, okay, cool. We know that cash is in circulation, perfect. Where is cash in circulation? And in addition to that, where should we start with the base of our technology? And how do we want to reconfigure this? And to be honest, we need help.

So, you know, we applied to Techstars, and we were super fortunate that we got into the Techstars Anywhere program. I think it was a lifesaver and a reboot for us and the company primarily because, you know, during the pandemic, we had lost, you know, over 70% of the folks that worked for the company at that time. So, going through that program helped us rethink a lot about strategy infrastructurel...how exactly we need to rebuild and reconfigure the company for success this next time around.

I think very early on, you know, we were just trying to do the business. We were just doing it rather than actually strategically building it. You know, that's the major difference between where we were versus where we are now is that everything that we do now is more methodical. When we look at, okay, where do we build merchant networks? Well, we're building them in a very strategic location. That particular location has this value to not only us as a company, the merchants in that area, but also the user base.

When we were able to take this more strategic position around, you know, how exactly we're building this business, we were actually able to see much larger opportunities that have always been there, but we just didn't see them. And so [laughs], I'm super grateful for, like, us kind of doing that recalibration because we were able to build a business that is ten times bigger than we initially thought that we were building.

VICTORIA: That's super interesting. So, yeah, like, pre-COVID, you're like, we'll get users, and then we'll figure out where to build. And then you had to, like, go through this full recalibration and focus on strategic regions, and that really opened up more opportunities and more growth than you had expected.

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VICTORIA: What does success look like for you six months from now or five years from now?

D'ONTRA: So, six months from now. We're hitting this hot streak with new clients and things of that nature. And we're going out, and we're pitching contracts that are bigger than I ever thought we would be able to pitch, honestly. And sometimes when I see the zeros on the proposals that we're sending out, there's part [laughs] of me that's like, oh, they're never going to say yes to this thing, but, one, they are, which is still shocking, even though we've gotten a few of these in.

And six months from now, I just want us to be doing it right. I know that sounds so arbitrary, and it sounds, like, so whimsical. But there are so many things that we're adjusting to in the marketplace and with our tech. Some of this is kind of new frontier for us. But what I would like to have happen is for the results in the next six months to indicate that we're doing it the right way and meaning that we have clients sticking around, we're still getting contracts signed, the network is growing, consumers are actually getting their needs met by our technology, and the company is growing at a rapid pace. That's what I'd like to see.

And granted, you know, we've, in the past, you know, few weeks here, we've doubled the size of the team, which is something that feels really great. But I want us to not lose sight of making sure that the team itself always has a common goal in mind, even as we're growing. And whether that's six months from now, 2, 5, 10 years from now, I want that to kind of be the core of the expectations of what I want this company to be able to do and to deliver.

VICTORIA: That's exactly the right attitude to have [laughs], right? It's like I want it to work. I want us [laughs] to, yeah, be successful. I think it all makes sense. You know, it's easy to come on a podcast, like, you know, you're eight years into the startup now, and you're starting to see some success. And it's like, here's how I did it. Everything sounds great. So, I'm glad you've also shared some mistakes or some things that you maybe would have reconsidered or done [laughs] differently before.

I'm curious: if you could travel back in time to when you first started, what advice would you give yourself, now that you've had this experience, to set your mind right from the very beginning?

D'ONTRA: Oh God, there's so much. There's so [laughs] much. One of the major things that I would do differently is I would read more. And what I mean by that is there are lots of lots of people that have been here in this position and done that thing already. I think in the past year, I would say probably one of the most influential books that I've read is Zero to IPO by Frederic Kerrest. And I happened to listen to it in Audible.

But when you talk about, like, just things being pivotal, or like [laughs], going, "Oh, that makes sense," yeah, you get that because being an entrepreneur isn't new. And there are folks that have already kind of cracked the code in some regards. So, if you don't have the existing network around you already, go get the materials. Go read the books or listen to the audios of people who have been there, done that. It's going to save you so much time. So, that would be the number one thing that I would change is I would really truly read more and ingest other people's experiences more, and reach out and get mentors and advisors as you're going down this journey.

The second thing that I would do is–it's important to move fast when you're building a company. It's important to respond to the market and all that stuff. That's all super important. That's how you live or die, right? You treat it like there's a fire behind you, and you have to lead it. You have this really hot thing. You've got to be in front of it always, or you'll lose it. And sometimes what we miss is we miss the opportunity to do it faster or better by just slowing down just a little bit. And what I mean by that is, like, I mentioned earlier about looking at the data and things of that nature.

There may be things in the data that are making suggestions that you should go a different direction. But because of how you've built this thing, you and your co-founders, and how you guys have built these things in your head, that piece of data may not seem like it's very relevant. Sometimes, it's good to take a breath and take an assessment of where you're at.

So, when you're with your team, whether you're setting this up monthly, quarterly, whatever it is, make sure that you're taking some time to make sure that you guys are aligned around where your company is, the industry is, and the signs that you're getting inside the space that you're operating in. It's going to save you a lot of time.

And I think the last thing that is probably the most important is for those out there who are listening to this that are CEOs, one of my board members/life mentors/ CEO mentors, a friend, and almost like a father figure to me at this point, one of the things that he said to me and that I've never gotten out of my mind is that the CEO position is the loneliest position inside of an organization. And the reason why is even though you may start a business with your friends or people who aren't your friends, whatever it might be, whatever those relationships might be, those folks will never quite understand what it's like to sit in your seat because everything must end with you. It has to.

Every successful organization is going to rise or fall by the person that sits at the top. And because that burden is so heavy, oftentimes, we don't want to go and talk to people when things are going bad. We don't want to admit when, like, hey [laughs], this thing that we've sunk all these resources into isn't really working. And just the sheer pressure of being that person sucks sometimes.

With that being said, take care of yourself and your key relationships. And I'm not talking about key as in, like, strategic. I'm talking about the people that love you. Make sure even though you're going down this journey, you're making time for your friends, your family, your significant others, your kids, whatever it might be. Because business stuff aside, and we're all chasing the–Man, this is going to be really successful one day, and I'll be able to change everyone's life. Sure, we're all chasing that.

But there is a now moment. There is a person right now that might want your love or your attention, and do not rob them of that. Make sure that you're still making time for those things that are important. Because you could very easily start building a business and five years later, look up and go, oh, this thing didn't work. And then turn around, and there's a wasteland of relationships that you just didn't pay attention to. That's not worth it. So, make sure that you're not only showing, you know, the folks that support you some love but show yourself love by still nurturing those relationships.

VICTORIA: That reminds me I heard something about like, your rest ethic should be as good as your work ethic. And your rest ethic includes that time that you spend with family, or whether it's your religion, or your hobbies, or anything like that that makes you feel whole and like yourself, which I know can be a difficult thing to do when you're balancing starting a new business and thinking about the growth and the future all the time. So, I really appreciate that.

You know, you mentioned mentorship and these networking and relationships. Bringing it all the way back to Start Up San Diego Week, I'm curious if you have thoughts on how founders could get the most out of those types of events. And what draws you back to Startup San Diego or startup weeks in general?

D'ONTRA: Just as a caveat to all this, even though I'm on the podcast and stuff like that, and I'm sure if you Googled my name, you'll see that I've been on TV and stuff, I generally don't like networking [laughs]. I'm a major introvert. So, like, when you put me in an event like that, it's very hard for me to talk to people. Like, when we met, it seems that would be contrary to what I'm saying because we were strangers, and I came over, and we started chatting and stuff like that. And by and large, like, that's not always, like, an easy thing for me to do.

The reason why I'm saying that is that if you're that kind of person, do what you have to do to be more extroverted because sometimes that extroverted or that more open or welcoming side of you will allow for spontaneous interactions to occur. And so, when we think about events like, you know, Innovation Week or something like that, there's a lot of opportunity for you to either meet people that are on your journey or a similar journey like you who've been there done that, or even just to offer a different perspective.

And if you're in a place where you're open and constantly seeking, amazing things can happen, right? You could end up with your next co-founder. You could end up, you know, with your next investor. Or you could end up talking on a podcast with a stranger that you met just a few weeks ago, right? So, anything can happen. Keeping yourself open to the opportunity and the ability to extract as much value as you can out of those events.

It's really interesting to kind of have your pulse on what's going on, even if it's outside your industry. We're a FinTech, but I go, and I pay attention to things that are going on in aerospace or in health because it's always good to, one, not completely have yourself submerged in just your industry, even though that might sound really great.

People like folks that can talk about a myriad of different topics [laughs]. So, it might be useful if you can go and have a chat with a stranger about, you know, what's the latest in aerospace, right? It gets you out of the brain drain of what it is that you do on a daily basis. But also, you get to learn some new things and cultivate some new relationships.

VICTORIA: I love that. Yeah, I listened to...I think it's Happiness Lab episode where they talk about random conversations with people those, like, sparks of innovation or things like ideas you never would have thought of if you hadn't run into this random person [laughs] and talked to them for five minutes about, you know, what they do in health tech, or what they do for their consumer product that they're building. So yeah, I think that's great.

And I've been excited to be here in Southern California for the last three years and starting to grow that network and meet people like yourself who are doing really interesting things. I'm curious if you have any questions for myself or about thoughtbot, or the podcast, or anything.

D'ONTRA: Yeah. So, you say that you've been here for three years. Tell me a little bit about your journey, how'd you get here, and why you chose the podcast life, right? As one of your many things.

VICTORIA: That is one of my many things, right? So, I grew up in Washington, D.C., And my career was in tech and civic tech. I was working for big three-letter agencies and some pseudo-federal banks like FDIC, and Fannie Mae, and PBGC, all the acronyms all the time. And we got an opportunity in early 2020 to move here for my husband's job. And we moved out here, and I decided to take a switch out of the federal space and get into more commercial consulting.

And I was lucky enough to find thoughtbot; they had a position that just looked great for me. And when I joined, you know, we have an internal collaboration thing called Hub that I think our CEO wrote and writes with the other people. All the developers on our team all contribute to it. But he posted a message about this Giant Robots podcast and if anybody wanted to be a new co-host. And I was like, "Sure, I've done a little podcasting here and there, and I have a microphone, so I'm ready to go."

And little did I realize just how popular the [chuckles] podcast was. And it ended up being a really great avenue for me to meet people and, learn more about their stories, and build relationships in a way that has been really impactful and meaningful. And like I said, you know, you never know how someone you meet might help you [laughs]. So, sometimes I'll interview people, and I'll get an idea about something that is, like, exactly relevant to the work that I am doing that week, just total kismet however it came about. So, that's how I got into podcasting and how I'm in thoughtbot and here in Southern California.

And so, I'm super lucky that I live in a place where there's lots of events going on all the time and lots of great people to meet. Between LA and San Diego, you could go to a different event every single day, probably [laughs], and meet people who are working on cool stuff.

So, my background was really in operations and maintenance and taking federal agencies into more modern practices with digital services, and agile development, and DevOps. And now I'm taking kind of a similar lens but to commercial partners who are much faster and can make change quicker. And, in some cases, are doing things in even cooler ways than I could have thought and trying to think about how to move them forward with their infrastructure and how they deploy software.

D'ONTRA: That's fascinating. And, you know, it's difficult to be in Southern California, right? New events every day.

VICTORIA: And then yeah, I'll go walk my dog in the morning--

D'ONTRA: [laughs]

VICTORIA: And people are out there surfing. And I'm like, I could surf all day. I don't have to work [laughs].

D'ONTRA: Right?

VICTORIA: But I do. I got to work.

D'ONTRA: It feels like the world of limitless possibility, right? [laughs]

VICTORIA: Yeah. You almost feel, like, a pressure. Like, everyone else is starting their own company. Why am I not starting my company? Everyone's doing cool stuff all the time. So, you get motivated that way by being around a great group of people who are...everyone is very happy and sunny and [laughs] for the most part, the people are so nice.

D'ONTRA: Definitely a departure from the East Coast, right? And, like, I'm sure you came here with, like, that hustle mindset, where you're like, got to get it done, which is probably why you do, like, a million things. But then also, you have all of these people [laughs] that, like, I don't know, like, cares to the wind when they need to, right? Although you've got lots of successful people. But, sure, like, more or less down here, it's like, hey, you know, like, let's live life first and [laughs] make the dollars second.

VICTORIA: It's very casual. I got rid of all of my blazers. There's no more of that anymore [laughs]. People when they found out that I was moving to California, they were like, "That makes sense for you [laughs]," like, just the general, like, vibe.

D'ONTRA: [laughs]

VICTORIA: And I'm a rock climber. So, they're like, of course, you're going to go somewhere where the outdoors is prioritized, yeah. Versus when you live in D.C., it's like the news is happening to you.

D'ONTRA: Yes [laughs].

VICTORIA: And it's very, very close. So yeah, it's interesting. I love it, though. And it's cool to take experience from that and then apply it to this world and how people might think about stuff. So, I was worried that, like, my experience might not translate, but it has. It's been very helpful [laughs] in some cases, right?

Is there anything else that you would like to promote today?

D'ONTRA: Yeah, so, you know, maybe for a future conversation, but in line with, you know, your background and what you're talking about, I would love to have a discussion around CRA, the Community Reinvestment Act, for those who don't understand the lingo, right? Because Spare's latest, like, golden nugget that we've really been just, like, kind of moving on and we're talking to federal regulators about is actually our impact on banks and the Community Reinvestment Act.

For those who follow the news and know, you know, the time and space that we're in right now, there are some changes that are taking place inside of CRA. And it's very fascinating because when you say about your background of helping agencies kind of modernize things with digital, that's effectively what we're doing with our tech, and we're getting a lot of support from the government.

And so, you know, I think that we're really doing some very interesting things that are starting to get some really great attention. We recently partnered with Visa on one of our initiatives, and we're talking to a few other really large organizations and government organizations so that this technology can really be used at a scale, honestly, far beyond what I ever imagined. But when we talk about, like, actually helping people, we're doing it [laughs]. We're doing it in this very unique way, which I'm super stoked about. But maybe we'll have a chat about that in the future.

But I think, you know, for those of you that are listening to this and you're curious, you know, what it is that we're working on, feel free to reach out. It's gotspare.com. Feel free to email me: ceo@gotspare.com. I'm generally in that email box every day. Or even just checking out our service, you know, searching Spare on the App Store or Google Play, and just going in and giving it a test drive. And, you know, we're happy to hear your thoughts.

And for those of you who are out there that may be looking for a new experience, we are definitely growing this team, and we want to expand as quickly as we can. We have some really aggressive initiatives for the organization over the next 12-18 months. And so, we're not going to do it on our own. I'm super stoked to where we're, like, we're at a place where we're like, we're actively building [laughs]. We're actively moving. And so, if there was a [inaudible 38:44] for us, whether it's supporting us as someone who uses the application or supporting us as a merchant who's in our community.

There's lots of value that we're adding that we're turning back around to reach all small businesses. We're really working on combating inflation with our tech. And we've been able to do that, which is one of those really, like, refreshing byproducts of a tech company, or at least of our services. Like, we're actually adding real, true value to folks, and I'm super stoked about that.

VICTORIA: That's wonderful, and it's really close to my heart as someone who wants to see tech with purpose and who loves tech solving problems for people, especially groups of people that usually aren't the focus of founders who are trying to turn a quick buck, right [laughs]? The people who have real problems there's a real market there. It is a business, and it makes sense to start solving those problems. So, I'm really happy that you're working on it.

Thank you so much for coming in today and being a guest on the show. We will include all those links and wonderful ways to reach out and get connected with you in the show notes.

You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. And you can find me on Twitter @victori_ousg.

This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening. See you next time.

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Transcript

STEPHANIE

Hello and welcome to another episode of The Bike Shed, a weekly podcast from your friends at thoughtbot about developing great software. I'm Stephanie Minn.

JOËL

And I'm Joël Quenneville. And together, we're here to share a bit of what we've learned along the way.

STEPHANIE

So, Joël, what's new in your world?

JOËL

Well, as of this recording, I have just gotten back from spending the week in San Diego for RubyConf.

STEPHANIE

Yay, so fun.

JOËL

It's always so much fun to connect with the community over there, talk to other people from different companies who work in Ruby, to be inspired by the talks. This year, I was speaking, so I gave a talk on time and how it's not a single thing but multiple different quantities. In particular, I distinguish between a moment in time like a point, a duration and amount of time, and then a time of day, which is time unconnected to a particular day, and how those all connect together in the software that we write.

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STEPHANIE

Awesome. How did it go? How was it received?

JOËL

It was very well received. I got a lot of people come up to me afterwards and make a variety of time puns, which those are so easy to make. I had to hold myself back not to put too many in the talk itself. I think I kept it pretty clean. There were definitely a couple of time puns in the description of the talk, though.

STEPHANIE

Yeah, absolutely. You have to keep some in there. But I hear you that you don't want it to become too punny [laughs]. What I really love about conferences, and we've talked a little bit about this before, is the, you know, like, engagement and being able to connect with people. And you give a talk, but then that ends up leading to a lot of, like, discussions about it and related topics afterwards in the hallway or sitting together over a meal.

JOËL

I like to, in my talks, give little kind of hooks for people who want to have those conversations in the hallway. You know, sometimes it's intimidating to just go up to a speaker and be like, oh, I want to, like, dig into their talk a little bit. But I don't have anything to say other than just, like, "I liked your talk." So, if there's any sort of side trails I had to cut for the talk, I might give a shout-out to it and say, "Hey, if you want to learn more about this aspect, come talk to me afterwards."

So, one thing that I put in this particular talk was like, "Hey, we're looking at these different graphical ways to think about time. These are similar to but not the same as thinking of time as a one-dimensional vector and applying vector math to it, which is a whole other side topic. If you want to nerd out about that, come find me in the hallway afterwards, and I'd love to go deeper on it." And yeah, some people did.

STEPHANIE

That's really smart. I like that a lot. You're inviting more conversation about it, which I know, like, you also really enjoy just, like, taking it further or, like, caring about other people's experiences or their thoughts about vector math [laughs].

JOËL

I think it serves two purposes, right? It allows people to connect with me as a speaker. And it also allows me to feel better about pruning certain parts of my talk and saying, look, this didn't make sense to keep in the talk, but it's cool material. I'd love to have a continuing conversation about this. So, here's a path we could have taken. I'm choosing not to, as a speaker, but if you want to take that branch with me, let's have that afterwards in the hallway.

STEPHANIE

Yeah. Or even as, like, new content for yourself or for someone else to take with them if they want to explore that further because, you know, there's always something more to explore [chuckles].

JOËL

I've absolutely done that with past talks. I've taken a thing I had to prune and turned it into a blog post. A recent example of that was when I gave a talk at RailsConf Portland, which I guess is not so recent. I was talking about ways to deal with a test suite that's making too many database requests. And talking about how sometimes misusing let in your RSpec tests can lead to more database requests than you expect.

And I had a whole section about how to better understand what database requests will actually be made by a series of let expressions and dealing with the eager versus lazy and all of that. I had to cut it. But I was then able to make a blog post about it and then talk about this really cool technique involving dependency graphs. And that was really fun. So, that was a thing where I was able to say, look, here's some content that didn't make it into the talk because I needed to focus on other things. But as its own little, like, side piece of content, it absolutely works, and here's a blog post.

STEPHANIE

Yeah. And then I think it turned into a Bike Shed episode, too [laughs].

JOËL

I think it did, yes. I think, in many ways, creativity begets creativity. It's hard to get started writing or producing content or whatever, but once you do, every idea you have kind of spawns new ideas. And then, pretty soon, you have a backlog that you can't go through.

STEPHANIE

That's awesome. Any other highlights from the conference you want to shout out?

JOËL

I'd love to give a shout-out to a couple of talks that I went to, Aji Slater's talk on the Enigma machine as a German code machine from World War II and how we can sort of implement our own in Ruby and an exploration of object-oriented programming was fantastic. Aji is just a masterful storyteller. So, that was really great. And then Alan Ridlehoover's talk on dealing with flaky tests that one, I think, was particularly useful because I think it's one of the talks that is going to be immediately relevant on Monday morning for, like, every developer that was in that room and is going back to their regular day job. And they can immediately use all of those principles that Alan talked about to deal with the flaky tests in their test suite.

And there's, in particular, at the end of his presentation, Alan has this summary slide. He kind of broke down flakiness across three different categories and then talked about different strategies for identifying and then fixing tests that were flaky because of those reasons. And he has this table where he sort of summarizes basically the entire talk. And I feel like that's the kind of thing that I'm going to save as a cheat sheet. And that can be, like, I'm going to link to this and share it all over because it's really useful. Alan has already put his slides up online. It's all linked to that particular slide in the show notes because I think that all of you would benefit from seeing that.

The talks themselves are recorded, but they're not going to be out for a couple of weeks. I'm sure when they do, we're going to go through and watch some and probably comment on some of the talks as well. So, Stephanie, what is new in your world?

STEPHANIE

Yeah. So, I'm celebrating wrapping up a client project after a nine-month engagement.

JOËL

Whoa, that's a pretty long project.

STEPHANIE

Yeah, that's definitely on the longer side for thoughtbot. And I'm, I don't know, just, like, feeling really excited for a change, feeling really, you know, proud of kind of, like, all of the work that we had done. You know, we had been working with this client for a long time and had been, you know, continuing to deliver value to them to want to keep working with us for that long. But I'm, yeah, just looking forward to a refresh.

And I think that's one of my favorite things about consulting is that, you know, you can inject something new into your work life at a kind of regular cadence. And, at least for me, that's really important in reducing or, like, preventing the burnout. So, this time around, I kind of started to notice, and other people, too, like my manager, that I was maybe losing a bit of steam on this client project because I had been working on it for so long.

And part of, you know, what success at thoughtbot means is that, like, we as employees are also feeling fulfilled, right? And, you know, what are the different ways that we can try to make sure that that remains the case? And kind of rotating folks on different projects and kind of making sure that things do feel fresh and exciting is really important. And so, I feel very grateful that other people were able to point that out for me, too, when I wasn't even fully realizing it. You know, I had people checking in on me and being like, "Hey, like, you've been on this for a while now. Kind of what I've been hearing is that, like, maybe you do need something new." I'm just excited to get that change.

JOËL

How do you find the balance between sort of feeling fulfilled and maybe, you know, finding that point where maybe you're feeling you're running out of steam–versus, you know, some projects are really complex, take a while to ramp up; you want to feel productive; you want to feel like you have contributed in a significant way to a project? How do you navigate that balance?

STEPHANIE

Yeah. So, the flip side is, like, I also don't think I would enjoy having to be changing projects all the time like every couple of months. That maybe is a little too much for me because I do like to...on our team, Boost, we embed on our team. We get to know our teammates. We are, like, building relationships with them, and supporting them, and teaching them. And all of that is really also fulfilling for me, but you can't really do that as much if you're on more shorter-term engagements.

And then all of that, like, becomes worthwhile once you're kind of in that, like, maybe four or five six month period where you're like, you've finally gotten your groove. And you're like, I'm contributing. I know how this team works. I can start to see patterns or, like, maybe opportunities or gaps. And that is all really cool, and I think also another part of what I really like about being on Boost.

But yeah, I think what I...that losing steam feeling, I started to identify, like, I didn't have as much energy or excitement to push forward change. When you kind of get a little bit too comfortable or start to get that feeling of, well, these things are the way they are [laughs], --

JOËL

Right. Right.

STEPHANIE

I've now identified that that is kind of, like, a signal, right?

JOËL

Maybe time for a new project.

STEPHANIE

Right. Like starting to feel a little bit less motivated or, like, less excited to push myself and push the team a little bit in areas that it needs to be pushed. And so, that might be a good time for someone else at thoughtbot to, like, rotate in or maybe kind of close the chapter on what we've been able to do for a client.

JOËL

It's hard to be at 100% all the time and sort of always have that motivation to push things to the max, and yeah, variety definitely helps with that. How do you feel about finding signals that maybe you need a break, maybe not from the project but just in general? The idea of taking PTO or having kind of a rest day.

STEPHANIE

Oh yeah. I, this year, have tried out taking time off but not going anywhere just, like, being at home but being on vacation. And that was really great because then it was kind of, like, less about, like, oh, I want to take this trip in this time of year to this place and more like, oh, I need some rest or, like, I just need a little break. And that can be at home, right? Maybe during the day, I'm able to do stuff that I keep putting off or trying out new things that I just can't seem to find the time to do [chuckles] during my normal work schedule. So, that has been fun.

JOËL

I think, yeah, sometimes, for me, I will sort of hit that moment where I feel like I don't have the ability to give 100%. And sometimes that can be a signal to be like, hey, have you taken any time off recently? Maybe you should schedule something. Because being able to refresh, even short-term, can sort of give an extra boost of energy in a way where...maybe it's not time for a rotation yet, but just taking a little bit of a break in there can sort of, I guess, extend the time where I feel like I'm contributing at the level that I want to be.

STEPHANIE

Yeah. And I actually want to point out that a lot of that can also be, like, investing in your life outside of work, too, so that you can come to work with a different approach. I've mentioned the month that I spent in the Hudson Valley in New York and, like, when I was there, I felt, like, so different. I was, you know, just, like, so much more excited about all the, like, novel things that I was experiencing that I could show up to work and be like, oh yeah, like, I'm feeling good today. So, I have all this, you know, energy to bring to the tasks that I have at work.

And yeah, so even though it wasn't necessarily time off, it was investing in other things in my life that then brought that refresh at work, even though nothing at work really changed [laughs].

JOËL

I think there's something to be said for the sort of energy boost you get from novelty and change, and some of that you get it from maybe rotating to a different project. But like you were saying, you can change your environment, and that can happen as well. And, you know, sometimes it's going halfway across the country to live in a place for a month. I sometimes do that in a smaller way by saying, oh, I'm going to work this morning from a coffee shop or something like that. And just say, look, by changing the environment, I can maybe get some focus or some energy that I wouldn't have if I were just doing same old, same old.

STEPHANIE

Yeah, that's a good point. So, one particularly surprising refresh that I experienced in offboarding from my client work is coming back to my thoughtbot, like, internal company laptop, which had been sitting gathering dust [laughs] a little bit because I had a client-issued laptop that I was working in most of the time. And yeah, I didn't realize how different it would feel. I had, you know, gotten everything set up on my, you know, my thoughtbot computer just the way that I liked it, stuff that I'd never kind of bothered to set up on my other client-issued laptop. And then I came back to it, and then it ended up being a little bit surprising. I was like, oh, the icons are smaller on this [laughs] computer than the other computer.

But it definitely did feel like returning to home, I think, instead of, like, being a guest in someone else's house that you haven't quite, like, put all your clothes in the closet or in the drawers. You're still maybe, like, living out of a suitcase a little bit [laughs]. So yeah, I was kind of very excited to be in my own space on my computer again.

JOËL

I love the metaphor of coming home, and yeah, being in your own space, sleeping in your own bed. There's definitely some of that that I feel, I think, when I come back to my thoughtbot laptop as well. Do you feel like you get a different sense of connection with the rest of our thoughtbot colleagues when you're working on the thoughtbot-issued laptop versus a client-issued one?

STEPHANIE

Yeah. Even though on my client-issued computer I had the thoughtbot Slack, like, open on there so I could be checking in, I wasn't necessarily in, like, other thoughtbot digital spaces as much, right? So, our, like, project management tools and our, like, internal company web app, those were things that I was on less of naturally because, like, the majority of my work was client work, and I was all in their digital spaces.

But coming back and checking in on, like, all the GitHub discussions that have been happening while I haven't had enough time to catch up on them, just realizing that things were happening [laughs] even when I was doing something else, that is both cool and also like, oh wow, like, kind of sad that I [chuckles] missed out on some of this as it was going on.

JOËL

That's pretty similar to my experience. For me, it almost feels a little bit like the difference between back when we used to be in person because thoughtbot is now fully remote. I would go, usually, depending on the client, maybe a couple of days a week working from their offices if they had an office. Versus some clients, they would come to our office, and we would work all week out of the thoughtbot offices, particularly if it was like a startup founder or something, and they might not already have office space.

And that difference and feeling the connection that I would have from the rest of the thoughtbot team if I were, let's say, four days a week out of a client office versus two or four days a week out of the thoughtbot office feels kind of similar to what it's like working on a client-issued laptop versus on a thoughtbot-issued one.

STEPHANIE

Another thing that I guess I forgot about or, like, wasn't expecting to do was all the cleanup, just the updating of things on my laptop as I kind of had it been sitting. And it reminded me to, I guess, extend that, like, coming home metaphor a little bit more. In the game Animal Crossing, if you haven't played the game in a while because it tracks, like, real-time, so it knows if you haven't, you know, played the game in a few months, when you wake up in your home, there's a bunch of cockroaches running around [laughs], and you have to go and chase and, like, squash them to clean it up.

JOËL

Oh no.

STEPHANIE

And it kind of felt like that opening my computer. I was like, oh, like, my, like, you know, OS is out of date. My browsers are out of date. I decided to get an internal company project running in my local development again, and I had to update so many things, you know, like, install the new Ruby version that the app had, you know, been upgraded to and upgrade, like, OpenSSL and all of that stuff on my machine to, yeah, get the app running again.

And like I mentioned earlier, just the idea of like, oh yeah, this has evolved and changed, like, without me [laughs] was just, you know, interesting to see. And catching myself up to speed on that was not trivial work. So yeah, like, all that maintenance stuff still got to do it. It's, like, the digital cleanup, right?

JOËL

Exactly. So, you mentioned that on the client machine, you still had the thoughtbot Slack. So, you were able to keep up at least some messages there on one device. I'm curious about the experience, maybe going the other way. How much does thoughtbot stuff bleed into your personal devices, if at all?

STEPHANIE

Barely. I am very strict about that, I think. I used to have Slack on my phone, I don't know, just, like, in an earlier time in my career. But now I have it a rule to keep it off. I think the only thing that I have is my calendar, so no email either. Like, that is something that I, like, don't like to check on my personal time. Yeah, so it really just is calendar just in case I'm, like, out in the morning and need to be, like, oh, when is my first meeting?

But [laughs] I will say that the one kind of silly thing is that I also refuse to sign into my Google account for work. So, I just have the calendar, like, added to my personal calendar but all the events are private. So, I can't actually see what the events are [laughs]. I just know that I have something going on at, like, 10:00 a.m. So, I got to make sure I'm back home by then [laughs], which is not so ideal. But at the risk of being signed in and having other things bleed into my personal devices, I'm just living with that for now [laughs].

JOËL

What I'm hearing is that I could put some mystery events on your calendar, and you would have a fun surprise in the morning because you wouldn't know what it is.

STEPHANIE

Yeah, that is true [laughs]. If you put, like, a meeting at, like, 8:00 a.m., [laughs] then I'm like, oh no, what's this? And then I arrive, and it's just, like [laughs], a fun prank meeting. So, you know, you were talking about how you were at the conference this week. And I'm wondering, how connected were you to work life?

JOËL

Uh, not very. I tried to be very present in the moment at the conference. So, I'm, you know, connected to all the other thoughtboters who were there and connecting with the attendees. I do have Slack on my phone, so if I do need to check it for something. There was a little bit of communication that was going on for different things regarding the conference, so I did check in for that. But otherwise, I tried to really stay focused on the in-person things that are happening.

I'm not doing any client work during those days that I'm at RubyConf, and so I don't need to deal with anything there. I had my thoughtbot laptop with me because that's what I used to give my presentation. But once the presentation was done, I closed that laptop and didn't open it again, and, honestly, that felt kind of good.

STEPHANIE

Yeah, that is really nice. I'm the same way, where I try to be pretty connected at conferences, and, like, I will actually redownload Slack sometimes just for, like, coordinating purposes with other folks who are there. But I think I make it pretty clear that I'm, like, away. You know, like, I'm not actually...like, even though I'm on work time, I'm not doing any other work besides just being present there.

JOËL

So, you mentioned the idea of work time. Do you have, like, a pretty strict boundary between personal time and work time and, like, try not to allow either to bleed into each other?

STEPHANIE

Yeah. I can't remember if I've mentioned this on the show. I think I have, but I'm going to again because one of my favorite things that I picked up from The Bike Shed back when Chris Toomey and Steph Viccari were hosting the show is Chris had, like, a little ritual that he would do every day to signal that he was done with work. He would close his laptop and say, "Schedule shutdown complete," I think.

And I've started adopting it because then it helps me be like, I'm not going to reopen my laptop after this because I have said the words. And even if I think of something that I maybe need to add to my to-do list, I will, instead of opening my computer and adding to my, like, whatever digital to-do list, I will, like, write it down on a piece of paper instead for the sake of, you know, not risking getting sucked back into, you know, whatever might be going on after the time that I've, like, decided that I need to be done.

JOËL

So, you have a very strict divisioning between work time and personal time.

STEPHANIE

Yeah, I would say so. I think it's important for me because even when I take time off, you know, sometimes folks might work a half day or something, right? I really struggle with having even a half day feel like, once I'm done with work, having that feel like okay, like, now I'm back in my personal time. I'd much prefer not working the entire day at all because that is kind of the only way that I can feel like I've totally reclaimed that time.

Otherwise, it's like, once I start thinking about work stuff, it's like I need a mental boundary, right? Because if I'm thinking about a work problem, or, like, an interaction or, like, just anything, it's frustrating because it doesn't feel like time in my own brain [laughs] is my own. What do work and personal time boundaries look like for you?

JOËL

I think it's evolved over time. Device usage is definitely a little bit more blurry for me. One thing that I have started doing since we've gone fully remote as the pandemic has been winding down and, you know, you can do things, but we're still working from home, is that more days than not, I work from home during the day, and then I leave my home during the evening. I do a variety of social activities. And because I like to be sort of present in the moment, that means that by being physically gone, I have totally disconnected because I'm not checking emails or anything like that.

Even though I do have thoughtbot email on my phone, Gmail allows me to like log into my personal account and my thoughtbot account. I have to, like, switch between the two accounts, and so, that's, like, more work than I would want. I don't have any notifications come in for the thoughtbot account. So, unless I'm, like, really wanting to see if a particular email I'm waiting for has come in, I don't even look at it, ever. It's mostly just there in case I need to see something.

And then, by being focused in the moment doing social things with other people, I don't find too much of a temptation to, like, let work life bleed into personal life. So, there's a bit of a physical disconnect that ends up happening by moving out of the space I work in into leaving my home.

STEPHANIE

Yeah. And I'm sure it's different for everyone. As you were saying that, I was reminded of a funny meme that I saw a long time ago. I don't think I could find it if I tried to search for it. But basically, it's this guy who is, you know, sitting on one side of the couch, clearly working. And he's kind of hunched over and, like, typing and looking very serious. And then he, like, closes his laptop, moves over, like, just slides to the other side of the couch, opens his laptop. And then you see him, like, lay back, like, legs up on the coffee table. And it's, like, work computer, personal computer, but it's the same computer [laughs]. It's just the, like, how you've decided like, oh, it's time for, you know, legs up, Netflix watching [laughs].

JOËL

Yeah. Yeah. I'm curious: do you use your thoughtbot computer for any personal things? Or is it just you shut that down; you do the closing ritual, and then you do things on a separate device?

STEPHANIE

Yeah, I do things on a separate device. I think the only thing there might be some overlap for are, like, career-related extracurriculars or just, like, development stuff that I'm interested in doing, like, separate from what I am paid to do. But that, you know, kind of overlaps a little bit because of, like, the tools and the stuff I have installed on my computer. And, you know, with our investment time, too, that ends up having a bit of a crossover.

JOËL

I think I'm similar in that I'll tend to do development things on my thoughtbot machine, even though they're not necessarily thoughtbot-related, although they could be things that might slot into something like investment time.

STEPHANIE

Yeah, yeah. And it's because you have all your stuff set up for it. Like, you're not [laughs] trying to install the latest Ruby version on two different machines, probably [laughs].

JOËL

Yeah. Also, my personal device is a Windows machine. And I've not wanted to bother learning how to set that up or use the Windows Subsystem for Linux or any of those tools, which, you know, may be good professional learning activities. But that's not where I've decided to invest my time.

STEPHANIE

That makes sense. I had an interesting conversation with someone else today, actually, about devices because I had mentioned that, you know, sometimes I still need to incorporate my personal devices into work stuff, especially, like, two-factor authentication. And specifically on my last client project...I have a very old iPhone [laughs]. I need to start out by saying it's an iPhone 8 that I've had for, like, six or seven years. And so, it's old.

Like, one time I went to the Apple store, and I was like, "Oh, I'm looking for a screen protector for this." And they're like, "Oh, it's an iPhone 8. Yikes." [laughs] This was, you know, like, not too long ago [laughs]. And the multi-factor authentication policy for my client was that, you know, we had to use this specific app. And it also had, like, security checks. Like, there's a security policy that it needed to be updated to the latest iOS. So, even if I personally didn't want to update my iOS [laughs], I felt compelled to because, otherwise, I would be locked out of the things that I needed to do at work [laughs].

JOËL

Yeah, that can be a challenge sometimes when you're adding work things to personal devices, maybe not because it's convenient and you want to, but because you don't have a choice for things like two-factor auth.

STEPHANIE

Yeah, yeah. And then the person I was talking to actually suggested something I hadn't even thought about, which is like, "Oh, you know, if you really can't make it work, then, like, consider having that company issue another device for you to do the things that they're, like, requiring of you." And I hadn't even thought of that, so... And I'm not quite at the point where I'm like, everything has to be, like, completely separate [laughs], including two-factor auth. But, I don't know, something to consider, like, maybe that might be a place I get to if I'm feeling like I really want to keep those boundaries strict.

JOËL

And I think it's interesting because, you know, when you think of the kind of work that we do, it's like, oh, we work with computers, but there are so many subfields within it. And device management and, just maybe, corporate IT, in general, is a whole subfield that is separate and almost a little bit alien. Two, I feel like me, as a software developer, I'm just aware of a little bit...like, I've read a couple of articles around...and this was, you know, years ago when the trend was starting called Bring Your Own Device. So, people who want to say, "Hey, I want to use my phone. I want to have my work email on my phone." But then does that mean that potentially you're leaking company memos and things? So, how do you secure that kind of thing? And everything that IT had to think through in order to allow that, the pros and cons.

So, I think we're just kind of, as users of that system, touching the surface of it. But there's a lot of thought and discussion that, as an industry, the kind of corporate IT folks have gone through to struggle with how to balance a lot of those things.

STEPHANIE

Yeah, yeah. I bet there's a lot of complexity or nuance there. I mean, we're just talking about, like, ways that we do or don't mix work and personal life. And for that kind of work, you know, that's, like, the job is to think really thoroughly about how people use their devices and what should and shouldn't be permissible. The last thing that I wanted to kind of ask about in terms of device management or, like, work and personal intermixing is the idea of being on call and your device being a way for work to reach you and that being a requirement, right? I feel very lucky to obviously not really be in that position. As consultants, like, we're not usually so embedded into a team that we're then brought into, like, an on-call rotation, and I think that's good for me. Like, I don't think that that is something I'd be interested in doing anytime soon. Do you have any experience with that?

JOËL

I have not been on a project where I've had to be on call, and I think that's generally true for most of us at thoughtbot who are doing software development. I know those who are doing more kind of platformy SRE-type things are on call. And, in fact, we have specifically hired people in different regions around the world so that we can provide 24-hour coverage for that kind of thing.

STEPHANIE

Yeah. And I imagine kind of like what we're talking about with work device management looks even different for that kind of role, where maybe you do need a lot more access to things, like, wherever you might be.

JOËL

And maybe the answer there is you get issued a work-specific device and a work phone or something like that, or an old-school work pager.

STEPHANIE

[laughs]

JOËL

PagerDuty is not just a metaphoric thing. Back in the day, they used actual pagers.

STEPHANIE

Yeah, that would be very funny.

JOËL

So yeah, I can't speak to it from personal experience, but I could imagine that maybe some of the dynamics there might be a little bit different. And, you know, for some people, maybe it's fine to just have an app on your phone that pings you when something happens, and you have to be on call. And you're able to be present while waiting, like, in case you get pinged, but also let it go while you're on call. I can imagine that's, like, a really weird kind of, like, shadow, like, working, not working experience that I can't really speak to because I have not been in that position.

STEPHANIE

Yeah. As you were saying that, I also had the thought that, like, our ability to step away from work and our devices is also very much dependent on, like, a company culture and those types of factors, right? Where, you know, it is okay for me to not be able to look at that stuff and just come back to it Monday morning, and I am very grateful [laughs] for that. Because I recognize that, like, not everyone is in that position where there might be a lot more pressure or urgency to be on top of that. But right now, for this time in my life, like, that's kind of how I like to work.

JOËL

I think it kind of sits at the intersection of a few different things, right? There's sort of where you are personally. It might be a combination, like, personality and maybe, like, mental health, things like that, how you respond to how sharp or blurry those lines between work and personal life can be. Like you said, it's also an element of company culture. If there's a company culture that's really pushing to get into your personal life, maybe you need firmer boundaries. And then, finally, what we spent most of this episode talking about: technical solutions, whether that's, like, physically separating everything such that there are two devices. And you close down your laptop, and you're done for the day. And whether or not you allow any apps on your personal phone to carry with you after you leave for the day.

So, I think at the intersection of those three is sort of how you're going to experience that, and every person is going to be a little bit different. Because those three...I guess I'm thinking of a Venn diagram. Those three circles are going to be different for everyone.

STEPHANIE

Yeah, that makes complete sense.

JOËL

On that note, shall we wrap up?

STEPHANIE

Let's wrap up. Show notes for this episode can be found at bikeshed.fm.

JOËL

This show has been produced and edited by Mandy Moore.

STEPHANIE

If you enjoyed listening, one really easy way to support the show is to leave us a quick rating or even a review in iTunes. It really helps other folks find the show.

JOËL

If you have any feedback for this or any of our other episodes, you can reach us @_bikeshed, or you can reach me @joelquen on Twitter.

STEPHANIE

Or reach both of us at hosts@bikeshed.fm via email.

JOËL

Thanks so much for listening to The Bike Shed, and we'll see you next week.

ALL

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