Building a Helpful & Kind Remote Team Culture w/ YNAB’s Jesse Mecham

YNAB jesse mecham remote team culture
Summary:

Founder of YNAB Jesse Mecham discusses their core values, his thoughts on building a company culture, and how to hire “genuine” people.

There’s less stress in a remote work environment. You give people a little bit more flexibility on their schedule. You treat them like adults. And suddenly, if life is good at work, then life is good at home. And the idea of work-life balance to me is wrong. I don’t see it as a tug back-and-forth. I don’t see them as mutually exclusive.

Today we have Jesse Mecham, Founder and CEO of You Need A Budget (YNAB)!

In this episode, we talked about how Jesse started YNAB in 2004 and how it evolved to be a remote company, his approach in delivering feedback and criticism, and the deliberate steps that Jesse took along the years to become a better remote leader

Jesse also shared about YNAB’s cultural manifesto, unique questions the team uses to assess new team members, and the impact of remote work on Jesse’s family life.

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Topics also covered on the podcast episode:

  • How Jesse started YNAB back in 2004 and found his CTO remotely
  • How Jesse delivers feedback and criticism as a remote CEO
  • YNAB’s unique ritual for all-hands meetings
  • YNAB’s hiring and onboarding process
  • The growing pains experienced while scaling a remote company
  • The unique interview questions that YNAB asks when hiring
  • Jesse’s past mistake in hiring and how YNAB learned from it
  • How remote work has influenced Jesse’s family life

Mentioned resources:

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Full Transcript:

Jovian: Hello, Jesse, welcome to the show.

Jesse: Thank you very much. I’m glad to be here.

Jovian: Great. Awesome. So, Jesse, I recently just started using YNAB. I’m loving it so far. What I really like about YNAB is how intentional it is and how opinionated it is. So, when I’m doing research about YNAB as a company, there are some parallels on the product and how you, as the CEO, run the company. So I want to deep dive a little bit more into that. So, yeah, so let’s start a bit about a quick intro about your background and YNAB.

Jesse: I started YNAB back in 2004, while I was still in school and was studying to get a master’s degree of accounting. And I originally launched it as a spreadsheet. So, it literally was a spreadsheet that you could copy and hand around, had zero controls on it. But it all worked out just fine. And it was a perfect attempt to ask people for money when you had something that was barely viable. And so, it started with a spreadsheet.

The spreadsheet lasted about a year and a half, and then I quickly realized that we needed real software so we started building that. And we just kind of evolved from platform to platform. We used old-school frameworks like Adobe AIR to be on Windows and Mac simultaneously. Now, we’re obviously on the web as a SaaS offering, and we’ve got the mobile, you know, iOS and Android clients as well.

So, the software has evolved from pretty rinky-dink software in a spreadsheet form all the way up to very sophisticated software. But the method that we teach, the method that the software reinforced whether in the spreadsheet medium or now has remained very much the same. And that’s kind of been our clarion call is that we teach people a new way of thinking about their money and then let the software just help them implement that.

Jovian: And, if I’m mistaken, you started creating or developing YNAB as a software when you met your CTO, Taylor. And it’s also in remote settings. Am I correct?

Jesse: Absolutely. Yeah. Taylor wrote to me and he said, “Hey, I can help you improve your spreadsheet.” You know, he was kind of an interested customer, but also interested on the tech side. And I said, “Well, I’d really like to have actual software.” And so, he said, “Oh, I can do that, too.” And so, he and I did lots of phone calls back and forth, like real phone calls, on landlines, you know. And we chatted for a little while and then kind of got the bare bones in place and an agreement in place. And he got off, and we launched the first version nine months after we met over the phone, having never met in person.

So we kind of tested the remote idea very early on before it was really a thing that I was aware of. And it works, so we’ve stuck with it ever since.

Jovian: That’s amazing. I think a lot of entrepreneurs or company leaders nowadays, some of them are quite lucky that they found that they can work remotely, like, super early. So I interviewed Hiten Shah a while ago. And for him, remote is just work because he’s been doing it since out of college, since 2003, and it just comes naturally. So that’s amazing.

So, I want to dive a bit more into your leadership style and the culture in YNAB. So, when it comes to remote work, the theme of the podcast…because sometimes you need to be very, very intentional when it comes to building culture and doing small actions like giving feedbacks, I’m not saying that you shouldn’t do this in the co-located companies, but you just need to amp up a little more. So, I want to ask you about your philosophy when it comes to giving feedback to your employees. Like, how do you deliver criticism and how do you deliver praise, for example?

Jesse: One rule that we follow, and I think this comes pretty instinctively to most people, but you always critique in private. You criticize…and I mean constructively criticize in private, one on one. And then, if you can, it’s nice to get praise at any time, but it’s very nice to have praise given in front of your peers.

So, we try and praise in public and critique in private.

Sometimes, it’s really nice to praise someone by saying that someone else said something to you about them. And we have that happen regularly on the team. And there’s something about that that’s quite nice. So that’s nothing revolutionary. You know, you don’t want to embarrass someone in front of people ever, and so we just stick to that. And, you know, it works very, very well.

Jovian: So still under this topic, so in one of YNAB’s podcast episodes back in 2016, so you mentioned about that you received some feedback, I guess, that you were quite a bit, “lax about setting expectations,” and you said you were going to work on it.

So I think a lot of CEOs, especially as they grow and they want to level up, they face this similar problem, especially in a remote case when…it’s kind of like catch-22. So when you start a remote team, you need a high level of trust. But when you trust people a lot, sometimes you forget that they need some kind of direction or expectation. So, at that time, what were the deliberate steps you take to be better at this?

Jesse:

Well, one point I want to make is that trust and clear expectations are not the same thing. So you can trust someone and still give clear expectations. That’s just good management.

And so, I want to make sure that’s clear. But dropping the ball…and that was the real issue was I wasn’t following through on what I’ve said. And so I read a book, and the book was “Getting Things Done” by David Allen. It’s kind of a classic at this point, probably. And I implemented it. Like, I didn’t question anything about it, what he said. I took his gospel and ran with it. And I’ve been running with that same program.

The podcast I talked about was in 2016, but the feedback was given to me years before that. So I’ve been running with the “Getting Things Done” method for a decade. And, you know, it’s not foolproof, nothing is. But I made marked improvement in following through and doing what I said I would do when I said I would do it, and not forgetting that I said something at all. And that was key.

So I took that, and it’s just a matter of getting everything that you say or that you think into something that you trust as far as systems go, and then regularly reviewing that system so that you don’t lose those things. That’s the gist of it. But it works for me, and I readily recommend it to others that are struggling with the same thing.

Jovian: Great. Well, you mentioned like not forgetting. So did you change your habit a little bit? So, let’s say, when you say something, did you, like, more deliberately take notes?

Jesse: Yeah. You can rapidly record, you know, log notes, and I use an app called Things. It’s fantastic. And I’ve been using that literally for a decade. And anytime I have a thought or think I need to follow up with someone, I type it very quickly with a quick keyboard shortcut. And then every Monday, I process everything that I’ve written and that’s that, and so that I know that I can let it go and…but I haven’t lost it.

Jovian: Got it. So, still on the culture side of this, you wrote a post on LinkedIn about, “Please stop talking about company culture,” which I 100% agree with. So, I realized…and you also have a cultural manifesto. So, I saw that cultural manifesto, and I feel like it’s really well-written. Like, it’s really well-codified in one paragraph. So, I wonder, back then, how did you go about assessing and analyzing your team and your company to figure out, “Okay, this is our manifesto, this is what we stand for?”

Jesse: I wrote it in about 30 minutes, and I didn’t do any analysis beforehand. So I think the key with setting those core values which is what that manifesto is is just asking yourself what you are right now, not what you are always or perfectly because no one is that, but what you are on the whole. And that’s what I did when I wrote that.

I just I sat down and rattled off the things that I thought I had and that the team had already as far as attributes. And I didn’t write anything aspirational. You know, I just wrote what we are, and that was key.

So, you can aspire to do those things better, but you can’t aspire to do something that you don’t possess at all. That doesn’t work because then you’re saying something that you aren’t already, and I don’t think that works as far as core values go. [inaudible 00:08:34]. That was it. So it resonated well with the team because the team was that already. And so, they happily accepted it saying, “Well, yeah, this sounds great because this is who we are.” And then the thing you do is you make sure that you hire people that that manifesto resonates with, and you’re off to the races on that one.

Jovian: Got it. That was also kind of, like, my next question, like, did you ran it before it’s published? Like, what did the team think about it, or do you have any additional feedback on that? Quick question, how big is YNAB now?

Jesse: We’re just a little over 100 employees [inaudible 00:09:09].

Jovian: And how big were YNAB when you published the cultural manifesto?

Jesse: I’m not totally sure, probably around a dozen employees.

Jovian: It’s interesting because a dozen, so it’s still pretty small.

Jesse: Very small.

Jovian: I think it’s a really cool…I think a lot of companies forget this, that you have to figure this out in a very early stage, which it doesn’t. I think a lot of companies only think about this when they are, like, 30 or 50 people, which still make sense. And what I’ve seen is when your company is bigger, as a CEO, you kind of don’t know, like, you’re a bit detached just because the company is big from day-to-day operating. So when you’re that big, a dozen, I can totally imagine that people see it as, “Yeah, this is what we are and this is our [inaudible 00:09:59].” That’s a fantastic move actually.

Jesse: Yeah, it was very easy. And the nice thing is if you start early…you can do this at any point, it is easier when you’re smaller. Absolutely.

Jovian: Speaking of this, this cultural manifesto, has it kind of, like…you know, did you modify it or, like, evolve over time?

Jesse: The actual paragraph that you cited, we have not changed at all. The core values themselves, we distilled down to seven. So, the manifesto includes…it’s a little bit of a broader description of the core values we’ve adopted that are part of our…like, a working document that we regularly review and cite. That’s seven core values that we have.

Jovian: I really love it because a lot of times, like, culture can be some kind of, like, buzzwords, “Oh, we love our company culture.” But I like that you just codified it down. And one thing that I really liked is a quote from Jason Fried of Basecamp, like, culture is not this big thing, but it’s things that your company do every day, like, on a 50 days average, what does your company means, that is your culture.

Jesse: People confuse it with, like, the vibe of an office, like the brand of an office. It has nothing to do with that. It’s more about the company character and far less about the company, you know, cafeteria you build out.

Jovian: Totally. I agree with that. So, I want to talk a bit about all-hands meeting. So I found it’s a very interesting topic because I realized, like, a lot of founders actually still struggle like, “What do I talk in the all-hands meeting? What should I prepare?” I’m just curious, what’s the format in YNAB, and how do you prepare for this meeting?

Jesse: I follow a Google Slides template that never changes. I just swap in little bits that are different. So, we always start with welcoming people that are new, newly hired, and then I pull out a snippet that I want to emphasize from our three-year vision that I wrote at any point. You know, it could have been I wrote it three years ago. I could have written it a month before, depending on where we’re at in that three-year plan. But we all read a part of that vision just so it kind of stays top of mind.

And then we’ll review one of the seven core values and talk about that very, very briefly usually. And then we go over goals, where we stand for the year on our goals, where the financials are. And, at that point, my part wraps up and then I turn it over to our chief product officer. And…no, that’s not true.

Then we have an employee presentation on any topic they want. And the rule is that we always have the newest, you know, new people go first.

But because we hire so often, you know, people, they wait a long time before they present, but they can present on any topic. And it allows a remote, you know, workforce to kind of get to know someone behind the scenes a little bit, which I find is important. So we’ll never get rid of that, you know, random subject of presentation. I love that part.

After they’re done, then we turn it over to our chief product officer, and he runs all of our demos. So, each of our teams will demo whatever they’ve worked on for the last cycle. So you may ask how often we run them, and we run an all-hands meeting every cycle. And we run cycles on, you know, a six-week…I don’t wanna call [inaudible 00:11:04] but six weeks cycle, two-week break, and then we get back onto another cycle again.

Jovian: It’s pretty similar to Basecamp, like, shape of method. [crosstalk 00:13:11]

Jesse: Yeah. I think they might have been part of our original inspiration. I know we’ve riffed up on that system, but I like that cadence. [inaudible 00:13:18] were too fast but stuff that’s too far away kind of you lose your grip on it as well.

Jovian: So, like, I can talk about that for hours, but that little…kind of a bit off-topic. So a quick question, you mentioned about random subject, is it, like, totally random, not necessarily work-related?

Jesse: Yes. The only rule is that it cannot be work-related. We ban work. So we’ve had people demonstrate how to bake really, really good biscuits, how they take care of their yard, you know, whether we’re all in a simulation, a magic system from a sci-fi book, a charity that this person was really active in. It just runs. It’s so fun. And you do really get to know the person. And we are putting them on the spot. It’s not fun for remote-working possible introverts to do that. But they do a really good job. And, yeah, it’s a lot of fun. So I love that part of it.

Jovian: That is hilarious. And I also found this very consistent, which [inaudible 00:14:12]…so when I was doing research about YNAB, it’s just an emphasis on, you know, a sense of humor. And I think it also came from your personality as well, I think. Like, you try to just…

Jesse: It’s just more interesting. Like, who wants to hear about work all the time?

Jovian: Totally.

Jesse: If someone talks about only work ever, I wouldn’t want to keep, you know, talking. It would get boring. So, you let people show their whole side, and I think it makes for a more interesting team.

Jovian: Yeah. Amazing. So, in one of your interview, you mentioned that you had one misfire in hiring, which where you found that the remote employee missed the energy from an office situation, and since that, on interviews, you asked if he or she gets energy from people, and you ask them if they have a plan to get that energy. I love this approach because I like how you don’t dismiss this person entirely but ask them if they have a plan.

So, I’m just curious, so I know that YNAB creates, like, amazing benefits and perks for the companies and, as you mentioned, the culture of being intentional. Do you also kind of, like, do some check-ins from time to time to ask them, “Hey, did you go to meet up or something like that?”

Jesse: Or check-ins on whether they’re kind of interacting socially, kind of getting out a little bit, you mean?

Jovian: Yes. Or let me rephrase that a bit, either check-ins or kind of, like, do you help facilitate this in any way, you know?

Jesse: I mean, we do have meetups for the teams, but those are, you know, about once a year. And so they all get together. And then, we have an annual retreat for the entire company, where we all get together.

You know, they can work from wherever they want as long as the internet is reliable and, you know, if they need to have phone calls that it works out wherever they are. But the key is that you don’t want to pass it over to someone because they never have worked remotely, if they could pick it up pretty quickly.

And we’ve had plenty of people say, “Man, remote work was harder than I thought it would be. But now I’m doing just fine.” It’s just a matter of being patient with the transition.

And we’ve only had it happen at one time where someone, they really just said, “Yeah. I can’t do this.” And that is what it is. But most of the time, people will happily adapt. There’s so many benefits to it, that it doesn’t take a lot once… There’s some intention at the start, and then you really do find a rhythm. And it’s not something that I found that we have to regularly train on or things like that. It comes pretty naturally for people.

Jovian: I totally love this because I see that there are a lot, there are two types of remote companies. The first one is that they like to strictly hire people who has remote experience. And it’s not bad by itself. It’s just like that’s how they work. And the other companies like YNAB that, yeah, even though you don’t have a remote work experience, we can train you on that, or we can help you on that. So I totally love that.

Jesse: I mean, you know, to be honest, if you were to have two people that are equal in every single possible way and one person’s remotely worked for a decade, you’d give the nod to the one that already had the experience. But I’ve never had that situation where everything is equal. So, I would not want to toss out a candidate because they hadn’t had that experience [inaudible 00:17:28].

Jovian: That’s amazing. You mentioned about company meetups. So you have these small meetups and then the big meetup. It’s kind of like the company retreat. And can you share a bit more about the small meetups like…? So it’s basically, like, the product team meetup, exec team meetups, or marketing team meetups, is that how it’s designed?

Jesse: Yeah. Absolutely. We’ve got different support teams that have different specialties. You know, they’ll meet up together. The executives meet up quarterly because they’re in a little bit of a different cadence. But the other teams will meet up at least, you know, every…you know, once a year, and on the off part of that year, we’ll do the company retreat. So, hopefully, they’re meeting with someone else from the team every six months. You know, we have the big company retreat, and then about six months later, the smaller team meetup. It just does wonders for connecting people and improving the remote work aspect to get together every once in a while.

Jovian: Amazing. So, for this small meetup, like how many days is used?

Jesse: Right now, we’re running them two full days. So they’re traveling on day one, full day two of work, full day three, and then travel out day four. Our feedback from the team is that that’s a little too short. So we may extend them to probably try three days, or once you’ve done all the work of the logistics, staying another day might make pretty good sense.

Jovian: So the small meetups, correct me if I’m wrong, it’s a bit more work-focused compared to the big meetups. Is that correct?

Jesse: Yeah.

The retreat, that big meetup, we don’t work at all. But the team meetups, they’re work-focused. I mean their goal is to get things done and really use that for work time.

They play a little but like in the evening, you know, nothing… it really is work. You know, they’re in a conference room, it’s boring…it’s not boring, but it’s work, you know, definitely.

Jovian: So I only know that a lot of remote companies have small meetups only…after I started this podcast. And it’s interesting because everyone does it differently. I just find it fascinating. So, you know, in terms of scaling, now you guys are like 100-plus people, and before it was like from a dozen, 50 people and whatnot. So, as you look back, so I wonder what are the things that you think YNAB as a company is getting better as you’re scaling remotely, or what are the biggest pain points in the early days that you guys now are better at?

Jesse: Probably the very largest was bottlenecking at kind of the product strategy, product feature junction.

So we’re trying to push down more decision-making to smaller teams and kind of distribute problem-solving that way and not have all problems solved way high up the chain and then having prescriptions pushed down. Instead, we want the problem to be defined and solved at a much lower, smaller team level.

And so the bottlenecking there, I don’t think you get as good of an idea. I don’t think the solution will be as elegant or effective when everything comes from way high up and it’s slower. So, that’s probably the biggest push we have towards scaling.

There are other little aspects that are uninteresting probably for a podcast. But the big one is just steering the product. You know, you want to start thinking about big strategy at the top, at the very biggest level, but you don’t want to prescribe solutions to the problems at that level because there are far too many problems, and I think you bottleneck up there pretty quickly.

Jovian: I like that you also acknowledge that sometimes the solution is probably not as elegant as it can be, but the trade-off is you give this authority for the smaller teams. And that’s just good for the company.

Jesse: Yeah. Well, no, I mean that the smaller team will come up with a more elegant solution. I mean [inaudible 00:21:28]. It’s because they’re able to obsess over one problem and not be thinking about two dozen. And knowing that you’re a bottleneck, you need to solve two dozen problems, I think there is where lies the error. But if you have one team obsessing over one problem and that team is cross-functional, you will get a very elegant solution in comparison to having, you know, one small leadership team attempting to solve everything.

Jovian: Got it. So I want to move on a bit to the YNAB’s hiring process. So, one of the things that you mentioned online, or I think one of the comments on the blog post said you guys acknowledge that you guys are hiring slowly…

Jesse: We do hire pretty slowly.

Jovian: …and you accept that. And can you share a bit more about, you know, how long the average hiring cycle is, the process, and so on?

Jesse: The hiring cycle is different for different positions. But it’s been, you know, 10 weeks-plus, and we want it shorter for all the obvious reasons that you’d want your hiring cycle shorter. That being said, if you were to say, “Well, we can make it shorter for you, but you won’t be able to nail that hire as far as their fit into the culture,” then I would say, “I don’t care if it takes six months.”

It will take as long as it takes to make sure that they’re a core value fit. Technical fits are easy, core value fits do take us, at the moment, with this iteration of our process, do take us longer. But so far, we’ve hired right.

And so, it’s just a matter of saying, “Well, gosh, wouldn’t we like it shorter so we could be more competitive, get offers out more quickly?” Absolutely. But you would never compromise core value fit for that.

Jovian: I think one of your company values that I found over and over again [inaudible 00:23:26] is like culture over craft, which, a very concise way in putting it. I really love that.

Jesse: You’ll find that if the core values are all synchronized and people are living them, you know, 95% of the time, that all of a sudden, you don’t have all these other issues that slow everything down.

So you can have someone that’s technically an absolute genius, but if they’re hard to work with, if they can’t communicate effectively, if they politic, if they gossip, it’s a deal-breaker.

Jovian: Definitely. So, I did a bit of research on YNAB’s interview process. So, I looked at Glassdoor, and I found an increasing pattern of questions even though I’m behind a paywall because I don’t want to create a Glassdoor account. I see the first questions for every candidate. But I found a pattern in there. So it’s super easy to spot.

So some of the questions that the YNAB team asked the candidates includes, what is your most embarrassing moment, and what are your favorite and least favorite parts of your current job, or tell us a time when you handled something poorly or made a mistake at work? So there is a pattern of like self-reflection here. So what kind of answer or characteristics that you’re looking for with these questions?

Jesse: We are looking for someone that’s being genuine. So, if you say what kind of mistake did you make at work, and they said, “You know, one time, I was five minutes late to this meeting. I was so embarrassed, you know. I don’t like being late to meetings,” I would be very unimpressed by that answer. I want to have you fall on your face. I want to… Well, figuratively. Well, although people have written about embarrassing moments where they did literally fall on their face, but you just want the answer to be genuine.

I want to get the real person. I don’t want to have you put on a show for me. I want you to show me you. I don’t want to know “interview you”. I want to know real you, the working you, the one that could demonstrate these core values that we’re seeking. So we’re really just looking for a genuine answer.

And obviously, there’s no right answer to an embarrassing moment. But I just want to see that they don’t give us some cop-out about, you know, how one time they called someone the wrong name. Come on, everybody’s done that. We want to hear something that’s meaty and that shows that you’re not afraid to show the real you because if you’re working with everyone at an organization that all is comfortable in their own skin, they all are not afraid to show, you know, the real self there, then you find that all of these other walls just come tumbling down and people can just get to work and enjoy themselves in the process. But when you have to kind of constantly ask yourself, “Is my boss this, or is my boss that, or does this direct report mean this or that?” I mean, my word, it slows everything down. And you can have technical geniuses, but you won’t get anything done.

Jovian: Do you find, like, these questions are usually a pretty good filter in figuring out if this person is, let’s say, you know, humble or self-reflective and whatnot?

Jesse: Yeah. Absolutely. We are always iterating on the questions. We’ll find that one doesn’t really differentiate one candidate from another, or 20 candidates from the other 20. So, we’ll tweak questions until we feel like that question adds actual value to the process, you know. So we had original questions in there but, you know, it’s always an iterative process to find those questions that are really helping the hiring manager suss out whether that person really has the values we’re looking for.

Jovian: Got it. I didn’t mention this, like, before we started recording, but you guys hire a mix of part-timers and full-timers, am I correct?

Jesse: Yeah. On our customer support side, we do. There are some people and some roles that really fit nicely into a part-time role, and there are some people that really just want part-time work. And so, when those two things overlap, we’ll pick up some customer support part-time roles. And we don’t do it for any other position beyond some teachers that run workshops for us and e-mail support.

Jovian: Yeah. That makes sense, especially when it comes to customer support because you want to cover 24 hours. Like, for example, like me, I’m in Taipei, Taiwan, right now. I think it’s 14 hours ahead of you. And if I have a question about YNAB, I will love to not wait a day.

Jesse: Yeah. Absolutely.

Jovian: So, yeah. That’s really amazing. So part-timers and full-timers, do they have the same onboarding process?

Jesse: They do not because there is more to the full-time just as far as benefits go and things like that. So it’s slightly different. But you could say 85% of it is going to be the same because you’re still getting those part-timers up to speed on the things they need to know to do their job well, and that’s going to be 95% of the job for sure.

Jovian: Awesome. So, I think it’s a good segue way to YNAB’s onboarding process for new hire. So I found it fascinating. So, whenever I talk about remote hiring with other remote startup leaders, their comment always put an emphasis in onboarding process. It’s almost like it’s a make or break that make this new hire will be successful in the company or integrate well to the company culture or not. So I love to understand a bit more about YNAB’s onboarding process, or if there’s anything more special in YNAB’s onboarding that you think other companies can learn from?

Jesse: We send them a welcome package that…I’m surprised more companies don’t do this, whether they’re remote or not.

Someone’s first day should feel awesome. They just went through the grinder to get there, and you really want to reinforce to them that they are where they are, you’re always there to guide, and that it’s going to be… like, the test is over. They’re on the team.

So, you know, it’s got to be a situation where the candidate that’s now hired, where she feels like, “Oh, man. I’m in. I’m in the club. I’m in the inner circle. You know, I’ve got it.” A lot of times, people start their jobs still kind of feeling like they’re being tested. And so, we do anything we can to just really assuage that fear where he or she can just get, you know, firing on all cylinders and set aside that fear that they’re still being scrutinized. They’re not. They’re on the team. They’re in. You know, and so that part’s key.

The welcome package is nice because we want to make a big deal out of it. And then, we also make sure that they have an onboarding buddy. I think we call them onboarding buddies. But just something where you say, “Hey, this person knows that you will bug them, and they’re expecting it. And if you don’t, you will offend them. So bug them. You know, ask them at any point, at any time, bend their ear and then three minutes later ask them something else. Like, they stand ready to just help you get any questions answered that we’ve missed in the process.”

One other key thing we do is about six weeks after their start date, we have them have a call with our COO to get feedback while it’s still fresh in their mind on what we, as a company, could have done better to onboard them. And that helps us kind of keep the process getting, hopefully, better each time.

Jovian: That is amazing. And when you do a welcome pack, like, is it a physical welcome pack that you send to their house?

Jesse: Yeah. You make sure it lands on the day, so you got to pay a little extra postage to make sure it’s timed right.

And, you know, it includes things you’d expect, swag and welcome… you know, the employees all write welcome notes, why they’re excited this person is joining the team.

So far, it’s gone over really, really well. And, you know, if there’s anything we can do to make it better, we’re going to do it. But I love the effect it’s had where it’s put people at ease and it’s let them hit the ground running knowing, you know, they’re on the team.

Jovian: Amazing. Now, as you were speaking, I was thinking, like, “Is there any other remote companies that do that?” I was always thinking of my previous guests. Like, I think you are the first one that mentioned like really sending physical package on, you know, their first day of work. So that’s amazing. I do think a lot of companies should do that. And I really like when you say you want them to feel that they’re an insider now. I think this feeling is super underrated in any situations because they’re feeling accepted…

Just for myself, for example, like, before I worked in the startup world, I used to work in a very traditional industry. I was selling stainless steel materials. So that’s a totally different thing. But at that time, the feeling was like, “I just want to work at a startup.” And I want to feel like I want to be a part of them, for example. So, when I got accepted at…previously it was CodementorX before it was Arc, and that’s a feeling that, “Oh, yes. I am one of them,” and it’s a really strong feeling that makes you identify with this company almost forever, if that makes sense.

Jesse: Absolutely.

Jovian: I totally love that. So, you know, we’re kind of, like, we’re running out of time here. So I want to kind of, like, ask some, like, lightweight personal questions about the impacts of remote work on your life, for example. So, Jesse, one of the biggest benefits of remote work that I’ve seen recently is basically you have more time to spend with your family. So, you’ve been working remotely since almost…around decade I think?

Jesse: Oh, yeah, longer than that. Yeah.

Jesse: I wonder what are the positive impacts that being able to work remotely brings to you, you know, and growing your family and so on?

Jesse: Well, I mean, there are the obvious ones that you…I mean, the average commute is 20 minutes, so you save 40 minutes a day. And 40 minutes for 5 days a week, where, you know, you get meaningful time very, very quickly, 200 minutes a week. You know, you multiply that out and you’re talking about serious time not sitting in a car. And that’s a big deal. And not to mention, the savings on just, you know, the wear and tear on the car itself.

Life is simpler. You don’t have to coordinate as much.

There are a lot of our employees that have gone down to one car instead of two. That saves a ton of money. They don’t have to wardrobe up, which is really nice. You can wear your clothes out a little longer. You know, you can have a fewer nice…you know, the nice things that you want to wear out, you can just be a little more selective there. I’m not saying you wear your sweats. There is a strategy that a lot of people use where they’re like, “No. I want to look good for the day,” and I agree with that. You want to start your day and treat yourself right, but you don’t have to… you’ll save money still, you know, on the clothing side. So there’s that.

And there’s less stress in a remote work environment. You give people a little bit more flexibility on their schedule. You treat them like adults. And suddenly, if life is good at work, then life is good at home. And the idea of work-life balance to me is wrong. I don’t see it as a tug back-and-forth. I don’t see them as mutually exclusive.

I don’t see them as canceling each other out. To me, if work is good, then life is good. And if home life is good, then life is good. But it’s just life. All of it is life.

And so, the idea of, like, work-life and balancing it evenly and something, I think we’re just chasing after a phrase that someone used that never has meant much. So just that flexibility, the recognition that life is life, and it includes all of these things… We recognize that you hire people that are honest, that want to do good work, and they’ll run through walls for you if you treat them well.

And I think allowing people to work remotely is allowing people to…or I should say is treating people well because there are so many arbitrary weird things about going into an office. And when old school or, heck, current CEOs ask me, “You know, well, how do you know they’re working?” and I’m, you know, sitting there talking at some conference, and I’m saying, “Well, you’re sitting at this conference. How do you know they’re working? I mean, you’re remote from your employees right now. So, they’re all in an office and you’re gone, how do you know they’re working?”

If you’re wondering whether or not your employees are working, then it is not because they’re remote or co-located, it’s because you wonder whether your employees are working and that is a totally different issue than the environment.

So, it’s a soapbox for me. But if you hire good people, it doesn’t matter if they’re remote or located in some Airbnb, they’ll do good work.

Jovian: That’s an amazing answer. And it also resonates so much with the information that it’s just less stress when it comes to remote work, and it actually makes you a better performer.

So, I just started working fully remote since a couple of months ago. And it’s not that I’m less busy. Like, I’m probably a bit more busier than I was working in the office, but it’s kind of interesting. Like, I just got more clarity in thinking, like, you can just think more clearly even though you’re as busy as usual, but it’s just that, you know, less distraction and the fact that the flexibility, it just, like, takes this burden off your mind. And there’s more clarity on your job and even your life, okay, what I wanna do with my life, which is, actually, is funny.

And by the way, this is not an ad or because I’m talking to you, but this is also one of the reason why I want to start budgeting with YNAB because like…you can think of it, “Okay, financially, where do I want to go like in a couple of months, a couple of years, and so on?” So I don’t think I will start, you know, being more organized with my life if it’s not because of remote work.

Jesse: Well, people are usually pretty intentional about their careers, and they morph their careers, they’re constantly spinning their career into money. That’s what we do. Careers generate money. So they’re very intentional about their career.

And then, once that career has converted into money with a paycheck, then they are unintentional with their money. And that is very weird to me because, to me, it’s all the same thing. Your career, all this effort you put into it, you know, it transitions into being in the form of money instead and suddenly it’s like, “Who cares?” “Wow, that’s a strange turn of events.”

You care so much about your career, and you just don’t care at all about your career as it’s represented with money. So it’s a strange kind of situation that everyone, well, 80% of people find themselves in, and we try and fix that. So I think we’ll always have a market for people that need to do it a little better than they’re doing it.

Jesse: Great. That’s amazing. So, yeah, Jesse, it’s been a fantastic chat. So where can people find you online?

Jesse: They could e-mail me if they wanted to. It’s jesse@ynab.com. I don’t tweet. I’m not on Facebook. I’m not on Instagram. I don’t have a blog or anything. So, you can just shoot me a good old fashioned e-mail and, you know, if you have any questions, then I’m happy to help out in any way I can.

Jovian: All right, awesome. Again, yeah, so, for listeners out there, check out YNAB if you need to budget. I’m a proud user, still working on it because it takes some time. But, as for now, it’s really worth it for me. I’m getting more organized and whatnot. This sounds almost like an ad. But, yeah, so, Jesse, thanks again for your time.

Jesse: Thanks so much, Jovian. Have a good day.

Jovian: Thank you.

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