Encourage Remote Team Risk-Taking: Fred Perrotta of Tortuga Backpacks

Your job is actually to help those people be great at what they do and coach them in that, not just tell them what to do.

Today we have Fred Perrotta, Co-founder and CEO of Tortuga Backpacks!

In this episode, we talked about the challenges of developing a physical product when you’re a 100% distributed team, building an epic place to work, and applying the principle of “players and coaches” in your company.

We also talked about Fred’s million dollar mistake, how to figure out if someone can be a good remote worker, and why you should always do project post-mortems.

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Topics also covered on the podcast episode:

• The challenges of developing a physical product as a 100% remote company
• How you can create an “epic place to work”
• How Fred applies the principle of “gentle guidance” as a remote leader
• Tortuga’s hiring process
• Signals to find out if someone can work remotely well
• Fred’s one million dollar mistake
• The importance of project post-mortems in remote teams

Mentioned resources:

• The 4-Hour Work Week by Tim Ferriss
• A Place to Do Epic Work
• David Heinemeier Hansson
• Basecamp
• Organizing Teams by Players and Coaches by Help Scout
• Laura Roeder of Meet Edgar: Build a Company That Doesn’t Need You
• Who by Geoff Smart
• Naval Ravikant
• Meetup.com
• Notion
• I F*cked Up (and You Can Too)
• Decentralized Decision Making
• Shape Up by Basecamp

Full transcript:

Jovian: Hello, Fred, welcome to the show.

Fred: Hi and thank you for having me.

Jovian: Real excited to have you here. As I just mentioned before we started recording, I’m always interested in business owners or startup founders that do physical products. So to start off, can you share a bit more about your past life at Google and how you started Tortuga Backpacks?

Fred: Sure. I was at Google for a little over three years. And towards the end, they have a program, it’s kind of like study abroad but work abroad. So I was abroad for three months and kind of decided I was gonna use that as, this is good timing, good excuse for me to leave. I’ll leave on a nice note. I get to take a little trip. So yeah, came back from that and decided to kind of make it official. We’d been working on the company at that point for about a year from the original idea for Tortuga. And yeah, we didn’t really know what we’re doing but were far enough along that I was kind of ready to quit. The business wasn’t far along enough to support me yet but the timing kind of felt right. So yeah, that was when I sort of jumped in and went, not full time but kind of half time or so. Some consulting and freelance work at the same time.

In 2009, my business partner, Jeremy and I went on a trip to see Europe, just kind of a typical backpacking trip. Early in the recession, tickets were very cheap. So we decided to take a vacation. And before the trip, we were trying to find the right backpacks and we ended up with the bags everyone carries, which is a kind of big hiking bag. But from when we were on the trip we realized that those weren’t really great for travel. So it just became a thing that we would talk about. We would complain about the bags, talked about what we would do better. And we had both just read the “4-Hour Workweek” before that. So the idea kind of became like, we have this problem and product idea, we have this book that we can follow the blueprint of. And it wasn’t that simple but it at least, that got us started and we kind of went from there.

Jovian: Yeah. I do want go on record to say that the hiking bag is so ugly. Like I do a lot of traveling. I just wanna go on record and say that because I think everyone in the world should know about this. And if you have the option to not do that when you’re traveling, just don’t. So yeah. So it’s kind of accidental, right? Like you were in kind of like, “Oh, I want to build a remote company.” And back then, I think 2009, it wasn’t really a thing to build a remote company. You just do it out of necessity. Whereas, for you and your business partner and you did that.

So, I’m always curious about companies that make physical products, especially when their business partners or teammates are not in the same space with them. In your opinion, what were the main, or I’ll say, what are the main challenges of running a remote company that makes physical products?

Fred: Yeah, all of the big challenges we still face, and we’ll probably always face to some degree. For the hard part for us, we manufacture in Asia right now. So there’s a bit of distance, language barrier, etc., there. That’ll probably always be the case. And that’ll be the case even if we had a headquarters and a home office. But the thing that remote makes difficult is, for us, mostly the product development, right?

If we had an office, we would talk to our factory, have them make some samples that we had designed. They would send us the samples or we’d go there, whatever. And then we would sit down and look at it together in-person as the product team.

So, our designer, we have a product marketer. So, you know, we have four or five of us on those calls. But if we could, we would all sit around, look at the exact same sample and say like, “Oh, let’s move this over here. This part doesn’t work, etc.”

But we can’t do that. So we do the best we can. Some of it we do over video, some of it we just defer to our industrial designer rather than doing it as a group or, you know, more straight forward changes. And then some stuff we just do the hard way and shift bags around between different people. So I might get a box of four or five samples and kind of go through it and make my notes, maybe test one of the bags and then send it to another team member. So sometimes there’s not a good answer. You know, the money that we’re saving on an office we spend with FedEx instead. But there are some times when you want everyone to see the bags and see it in person and it’s not always convenient to time it around a retreat or some time to work together in person. So FedEx it is.

Jovian: Right. Now, as you mentioned, it almost feels like for other startups that are building software, they almost kind of like take it for granted. Like, it’s software. You actually can interact with the product onscreen, you know, using stuff like InVision or whatnot. But for a physical product, and for us, software makers, I just feel like, well, it’s hard but we never realize it’s harder to people who make physical products.

So the next thing I wanted to talk about is you wrote this post titled, “A Place To Do Epic Work.” And this is a topic that I’m quite interested in because you know, David Heinemeier Hansson from Basecamp, he talks about not finding the 10X programmer or 10X team member, but you have to create a 10X environment. And for us, like Arc, when it comes to, you know, finding people to help hire the best people, we definitely understand that finding the right people is really hard. And then you’ve got to attack it from both ways. You have to, you know, find the right people and also you have to make your company a great place to work. So I’d love to dive deeper into this. Can you share a bit more about this piece and your insights on this?

Fred: Yeah. You make a good point that you wanna find the right people and create that culture, right? It’s not as simple as doing one or the other. You can’t just take a bunch of talented people and hope something good happens out of it. You also have to think about the culture. So, for us, we try to lean into some of the advantages that we have as a remote company. So, because we’re not in a big shared office with, you know, an open-office plan and all of the distractions that come with that that the Basecamp guys have talked about a lot too, you know, it makes it much easier to really focus on and do deep work. So, if you wanna be able to like block out all the noise, focus on a design problem or whatever it is that you’re working on and just knock out, you know, have multiple hours even, just no interruptions, no meetings, no one yelling on the other side of the cubicle or you know, talking about whatever, a remote company, and particularly Tortuga, is a great place to do that.

So for the people in, I think pretty much any role, but you know, particularly creative roles I think are often the people who mention this stuff and, you know, complain about it or raise these issues. Programmers too. That’s another common job where people get distracted where you really do need big blocks of uninterrupted time to do really good work. Remote is a great place to do that. And so that’s something that we really try to play out both in how we operate and the culture of not over-scheduling with meetings and stuff. And then when we do post job listings or on an about page or jobs page, we put extra emphasis on that so that people who, you know, have experienced the opposite in some open-office kind of culture, they can see like, “Oh, this actually is what I want because like that’s the environment where I think I’ll be more productive.”

So, that’s kind of one of the big ones that we think about there. And that one is easy with remote. The one that is harder with remote is keeping everyone coordinated and kind of on the same page or moving in the same direction. That’s part of that 10X culture. But being remote makes that one harder, I would say.

Jovian: Right. Got it. So, you also wrote in the piece that there are three goals that you consider when building a place for epic work. The first one is “autonomy”, and the second was “gentle guidance”, and the third is “remove roadblocks”. I’m curious about the gentle guidance part. Can you elaborate more on that? And from personal experience, how did you apply this principle when you’re leading Tortuga?

Fred: Yeah, I guess all of those bullet points have kind of informed how we think about coaching. That’s kind of how we talk about management at Tortuga is coaches doing coaching. So all those, kind of, will apply to how we think about coaching, which is that a coach isn’t just someone who is really good at doing the work and now gets to tell everyone else how to do the work.

Your job is actually to help those people be great at what they do and coach them in that, not just tell them what to do.

So that goes back to the gentle guidance that I was talking about where you know, if someone is, let’s say, doing something incorrectly, pursuing some work that we just don’t think it’s the right way to do it, like the way to correct that is not me to say, “That’s wrong, do it this way.” Instead, it’s like, “Your way is wrong. My way is right. You do it my way.” What we wanna do instead is talk more about why it’s being done a certain way and like how we’re trying to achieve a goal, right? So you wanna reiterate like, this is the goal. Maybe it’s an OKR, maybe it’s a company-wide goal for the quarter, something like that. And then it’s more about asking questions than telling someone what to do.

So, you know, with this goal in mind, how are we going about it? Why are we doing it that way? And sort of probing. Sometimes maybe that person does know what’s right and the coach was wrong. They didn’t know or they didn’t have all the information, maybe is more likely. And if that person is kind of going in the wrong direction or off-base and needs some guidance, that’ll usually become obvious through asking the questions.

Right? Like even without trying not to ask leading questions, sometimes just asking the questions, they kind of realize like, “Oh yeah, maybe I’m not thinking about it the right way.” You ask a question and they realize like, “Oh, I didn’t even think about that part of it.” And hopefully, between the two people or, you know, individually, they can kind of figure out what’s wrong and come to the right conclusion themselves rather than just being told like do this instead.

Jovian: Yeah, exactly. Sometimes when you ask something, we actually just need to voice it out loud and then to hear your own thought. And then mid-sentence, you’re probably like, “Okay, this is actually pretty stupid. Like, nevermind.” Something like that. It happens to me a couple of times. You mentioned about the term “coach” and “coaching”. So is this the word that you use in Tortuga? Like, internally?

Fred: Yeah, we stole that one from Help Scout. I guess they do that and they had a blog post about how they think about players and coaches as like an individual contributors.

Jovian: Yeah. It’s interesting like how even this slight change of terms can change the mentality of the whole company. So, for instance, I talked to Laura Roeder from MeetEdgar a while back. So, instead of managers only, they used “advocates”. So when you’re talking like marketing advocates, basically these marketing advocates are responsible to help the ideas of the team member to work with them and then advocate these ideas to up top. And so it is super interesting. Now, so, it’s also kind of showed the culture of the company, right? In the current form, how would you describe Tortuga’s current culture? And if you look back from your entrepreneurial journey, how did it get shaped this way?

Fred: Yeah, I think that the culture today actually kind of goes back to what you’re quoting in the blog post where we try and focus on autonomy. Some of the gentle guidance and that sort of coaching philosophy, I think informs a lot of the rest of the culture. So we’re still small teams, still mostly flat organization. Twelve people today. So yeah, we do kind of focus on that autonomy quite a bit. And again, that’s another thing where being a small team and a remote team makes it kind of easier for us to do. So, you wanna lean into your strengths. If we were, you know, a few hundred people, maybe those needs would be different. So I would think about it a bit differently.

But in the early days, you know, there’s not really a culture. You’re just trying to make something happen and get things done and you’re certainly not thinking about culture too much.

But yeah, we were coming from a place where the business kind of started inspired by 4-Hour Work Week and, you know, we didn’t wanna be showing up at an office every day. My co-founder and I were living in two different cities when we started. So some of this was just like, we started doing things in a way that the two of us could make work on the side, you know, at nights and weekends, things like that. And then we started working with some contractors for specific work, like industrial design and things like that, building our first website.

So, by the time, a few years later that we actually started to hire people full time or part-time to like actually be a core part of the team, we’d been working remotely and the two of us and everyone else, the freelancers that we work with us, for a few years. So it just felt natural to like keep doing that. It didn’t feel like, okay, now we’re starting for real. So now we get an office and get everyone in there. We just kind of kept doing what had worked and by that time, 2013, 2014, there was like Buffer and Basecamp and some other companies were talking about this more. So it felt like, “Oh we’re not crazy. Like, we’re doing it and it works, so therefore we are allowed to do it.” So that’s how we first started to like define the stuff and kind of put it into the core values.

Jovian: Got it. Got it. So the turning point, not the turning… So, when you realized that a lot of companies like Buffer, Basecamp try to do this and then you’re like, “Okay, let’s try to codify these things that everyone kind of knows in a company and make it more official,” I guess?

Fred: Yeah, there’s something to, I don’t know, just seeing other people doing it that lets you know, like even if you have the same idea, like they can think, “Oh, am I crazy? Is this gonna work or not?” But if you see other people that their businesses are working, they’re doing it remotely, then I don’t know, it shows you that like you’re not the only one. It is real. It can work. And it was the same thing with the 4-Hour Work Week, right? Like, we didn’t know how to start this kind of business, but there was a book, this guy, he was selling supplements or pills or something, but you know, he kind of laid out how to work with suppliers, how to do everything. So it became like, all right, we have this book so therefore we can do it. We just follow this. So that’s also why now I try to do a lot of, I don’t know, writing and talking about what we do because I know seeing other companies like really helped us when we were starting. So that’s why we can kind of like pay that forward or backwards or whatever direction to other companies starting out.

Jovian: Right, right. And so, I want to move on to the hiring part a little bit. So in one of your articles, you mentioned that hiring right is the key for a successful remote company and of course, the culture since it’s highly related to trust. And can you share a bit more about Tortuga’s hiring process?

Fred: Yeah, it’s something we think about a lot and have spent a lot of time on…

Jovian: It is hard.

Fred: …even though we’re a small company. It’s like our margin for error is a little smaller, just being a small company, you know, so it feels like more pressure on each hire. You know, like if you’re 10 people and you hire someone, that’s 10% of the company is new, you know? So most of what we do for our hiring is kind of pulled from this book called “Who” by Geoff Smart. And yeah, I don’t even know if I remember where we initially saw it recommended but have taken a lot of lessons from that book.

So, one of the first things they talk about and really focus on is not writing a job description where it’s like, you know, here are the tasks that you have to do, but they call it a job scorecard and it’s focused around outcomes. So it’s not like, you know, manage these ads, be in charge of this. It’s about like the actual results. So say three to five kind of results, like bigger things you want out of that role in the, you know, maybe next six months or something like that so that when you interview people, you can kind of score them against that like a report card and see, “All right, do I think they can achieve this outcome?” You know, it’s one thing if they’d done the job before but it’s another one if they like had similar outcomes or like achieved similar results. Right?

So it’s a little easier to judge people against that versus, “Manage this account or be in charge of this thing,” where like if they’d done a similar job, anyone, I guess, could be in charge of that. But are they gonna get the results that you want for the business? So that’s kind of a starting point in writing it. And then when we interview, we do two to three interviews, it kind of depends on the role. But usually, there’s at least one that’s about work history and their skills. So really just going back through past roles, like what they accomplished there, what was hard about the job. Like highs and lows, things like that.

And then we do a whole separate interview around, we call them value alignment, but the work culture fit. And that one is like much less about work history and more just getting to know that person’s history outside of work, how they like to work, what they’re looking for in their next role, things like that to make sure that there’ll be a good fit, how they wanna work is a good fit with how we work. And then sometimes we have an extra interview depending on the, if the role is really specific, sometimes we’ll also have another member of the team in a similar role interview. You know, for example, like I didn’t feel qualified for some of the roles to evaluate people’s work history as well, so brought another member to the team to help us with those.

Jovian: Right. So the value alignment stage, I always find this interesting. I think Help Scout has the same stage. Is there any particular question that you always ask in this value assignment stage?

Fred: Yeah, most of them are pretty consistent. Sometimes we’ll tweak it a little bit depending on the role, but most of them are just kind of understanding like a little bit about the person’s like travel history, work history. There’s a little bit of work stuff in there. And also kind of around remote work and how they work even if they haven’t worked remotely before. So, we kind of wanna understand like why are they interested in this role? Like, the company, the role itself, in working remotely and kind of see like what they’re after there and make sure that’s a good fit for how we work. Because, you know, most people, it’s their first remote role. It’s often very different than, you know, past roles in an office. So we wanna make sure like, what are they after and are they gonna be able to get that at Tortuga? Like, does this work from both sides kind of things.

Jovian: Got it, got it. You also talk about, you’ll look for self-starters, right? With high standard that people are motivated that work well in a remote team. And one of the signals is if you’ve worked remotely before, there’s a high chance you’re pretty good at that. Other than remote work experience, any other signals that you’re looking for to see if this guy was probably a pretty good remote worker?

Fred: Yeah, having remote work experience is a helpful one, but most people don’t. So have to look for other signals, right? So, for us, we look for initiatives. So that could be in anything. It could be at work that, you know, someone started a project at work or maybe like some club or social group or something like that at work or at school. It could be like some people use the term intrapreneurship which is like starting, you know, whatever new product or starting something new within an existing company. And then, of course, anything outside of work that someone’s taking the lead on, if it’s maybe they organize a meetup for whatever their hobby or interest is. Or maybe they’ve done some freelance work on the side to like hone some skills that they didn’t get to work on at their day job, but mostly starting anything. You know, it can be totally independent. It could be work or personal. It could be at school. Outside of that. Anything that’s a signal that this person like doesn’t just do like, “All right, here are my tasks for the day and I did those and I go home and then, you know, sit there and do nothing.” So that’s number one.

The other thing that we look for, and this is mostly through the application process is good written communication skills because I’m sure you know that if you don’t write well and clearly you’re gonna have a hard time communicating at a remote company.

So yeah, we sort of looked through those in the application and we’ll, you know, aside from just a cover letter, we’ll ask some additional questions. So it gives us a chance to like see some of their writing and see how well they explain things and communicate.

Jovian: Yeah. Even these couple of years, there’s this wave of, Oh, you know, there’s indie makers, indie hackers, no-code makers out there. And at the same time, it came at the same time as the trend of remote work. They file very complementary of each other and I think this is something, it feels like kind of like bigger, like more people are able to create stuff or at least there’s consciousness to get into that kind of mindset. You know, I think Naval Ravikant talked about this. About, oh, you have to create something from zero to one. And I just feel like, this is me just kind of rambling here, but I just feel like this is a great sign for future of work because it probably is easier or for remote companies to evaluate candidates based on their ability and how they are self-reliant, so to say.

Fred: Yeah, it’s good to see someone like taking the initiative and then being responsible for something. So, maybe it sounds trivial but, you know, if you run a meetup group for whatever, hiking or something, like that’s common out here in the Bay Area, you know, you have to decide where to go. You have to send the emails to remind everyone when it is and organize that like, yeah, maybe it’s not the hardest thing in the world but you have to be responsible and, you know, do it every month. So that’s a good signal to me.

Jovian: Yeah, exactly. And I think a lot of younger people, I don’t know if it’s correct, but a lot of people think about starting something as something huge. Oh, let’s say, to get something great in my resume, I have to create a huge side project. I have to create something from scratch, learn coding, which that’s actually not the case. Just like you mentioned, just create a meetup. Meetup.com is literally there. You literally just do write letters with your keyboards into columns so to speak.

Fred: And it’s better if it’s something you’re interested in. Right? Because then you’ll stick with it and not just like, “Oh, I’m doing this because it’ll look good on a resume,” you know?

Jovian: Oh yeah, exactly. Because if you’re doing it only for the resume, it gets old.

Fred: Yeah.

Jovian: So yeah, I think this is super relevant, slightly very relevant to what we’ve talked. So probably there’s a lot of overlap here, but we also talk about hiring for potential is super hard for remote teams other than the thing that we talked about, you know, starting a side project or just create something. Any other advice for relatively inexperienced people that never worked remotely before and want to find remote jobs even, you know, college grad and so on?

Fred: Yeah, it’s definitely one of the kind of disappointing shortcomings of remote companies. I think most of them are… One, it’s just hard to train someone remotely. You know, it’s much easier if you’re sitting next to each other. And then two, this is changing, but there are only so many remote companies that are even big enough to have a, you know, learning and development team or whatever. Like, maybe Automatic has one but the vast majority don’t. So, yeah, that part is tough.

Definitely getting any kind of experience you can beforehand just in I would say, within your role is kind of what’s useful and, you know, maybe that’s working at a more normal office job before or interning. But a lot of it you know, you can learn online or do like, you know, either for yourself or like maybe pro bono for like a local business that you like, you know, maybe you’re learning whatever SEO. So your favorite cafe you go to all the time, you know, you do some free work for them to learn it. And you know, that also then shows, you know, that you can take initiative.

So, like for us, like I said, it’s kind of about those outcomes as opposed to like, I don’t really care where someone worked before or if their degree is in, you know, whatever the same field as their job is.

But you do want to know that they can achieve these outcomes or that they’re like on their way to being able to. So, you know, you need some proof that they’ve done something similar in the past. And that can take a lot of forms. It doesn’t have to be that you did it in a remote company or a really similar one, but you do wanna see that someone has done these sorts of things before.

Jovian: Right. Did you experience first hand the difficulty of training someone remotely before?

Fred: Yeah. A bit of it. I mean, I guess when we started, everyone was like, there was still some sort of training, you know? But yeah, we’ve tried to do it a little better or have people move between roles where, you know, not like a massive change between teams or departments or something, but just kind of smaller changes to the roles and realizing like it’s really hard to like how do you help them get up to speed? Like, it seems like it should be very doable, and I think in an office we would be more doable. But you know, for us, it’s like if we don’t already have someone who knows about that field or expertise, then, you know, you’re telling them to take an online class or, I don’t know. It just feels a little bit like we have no… Like it should be doable. I want to help them. I think they can get there with a little bit of help. But then you feel like you have no resources to like make it happen, or I don’t know where to guide them to kind of bridge that gap. So definitely, a shortcoming for us. I don’t know about other remote companies, but I’d imagine they face some of that.

Jovian: Yeah. Honestly, I feel like even the co-located companies, coaching can still be an issue. Like, even onboarding new hires, which we’ll talk about in the next… So like, currently, do you have some kind of onboarding process for new hires? So let’s say if someone got hired in Tortuga tomorrow, so what are the next steps for these people? Is there any like a buddy system or something?

Fred: Yeah, we do.

I guess that’s another thing that’s hard with remote work, right? Like you show up on your first day at work and like, what do you do? There’s nowhere to go. Like you don’t show up at the office and no one escorts you to your desk, you know. So you just turn on Slack, I guess. So yeah, we’ve tried to make it a little less weird or make it kind of like an easier start for people.

So yeah, we’ve got a bunch of kind of to-dos for them to get all their accounts set up, all that sort of routine stuff. And then, yeah, we set them up with a new hire buddy. We try to get someone who they won’t necessarily work with every day, just in their day to day work. So it gives them another person that they have an excuse to like talk to, get to know, and, you know, they don’t have to feel weird reaching out or anything. And then that person can answer some of the questions about the company. Like, where do I find this information? How do I set up my direct deposit? That sort of thing. So helps to spread out some of the onboarding work between myself, our general manager, the new hire buddy. Like, kind of gives them more people to talk to, more points of contact and lessens the work on us.

And then we’ve experimented with a few other things. Like, I would send an introductory email that’s like to introduce the person and also kind of hype them up and talk about why we hired them. You know, we want them to know like that we’re excited and talk about all the awesome stuff they’ve done and why we think they’re a good fit so that the rest of the team can get excited.

We’ve experimented with some like video all-hands on Zoom, things like this, just to like, I don’t know. So they get to see everyone’s faces and, you know, we can all talk a little bit. It gets a little hectic trying to have too many people on a Zoom call, but, you know, just want them to feel like they’re showing to a team that’s like excited to meet them and, you know, we’re all people, not just means and the side.

Jovian: So, do you kind of have like a basic Wiki or documentation about the current company? If yes, what are the tools that you are using for that?

Fred: Yeah, Notion is the main hub for most of the like kind of evergreen information. And then we also in Google Drive we’ll store a lot of our SOPs just because there’s more screenshots and those might change more often. So we kind of section off some of that stuff there and then Notion is more for like how certain things work, like, you know, whatever, getting set up with systems and stuff the first day. And we try to write a lot about, like, how we operate and kind of our norms let’s say around things like productivity or like, do I need to have Slack on my phone? Do I need to respond? Like, how fast do I have to respond to emails? Like, do I need to leave this on 24/7? Should I have my notifications on?

So we try to tell people what boundaries are good to set at that point. You know, when you’re new you wanna do everything and you might not feel comfortable ignoring messages until tomorrow or whatever. So we try to like let people know that that’s okay and define those rules a little bit so they don’t have to, I know, try to impress anyone or figure it out on their own over a couple of months so we can just like tell them upfront what to think.

Jovian: Or feel lost. Yeah, they can feel lost sometimes. I just wanna let you know, even sometimes in co-located companies, onboarding can still be an issue. Like, you’re still there in your seat and then, okay, who should I find? And who should I look for? I mean, I think it’s still a bigger problem than everyone realized. It’s just because like people have a focus on the onboarding of remote companies. Oh by the way, on the Wiki stuff you mentioned about the whole kind of like history of the company, the norms and whatnot. Are you the one who maintains it?

Fred: I’ve written a lot of it just because, like, either to set the example or stuff that’s like my job to figure out. Like, yeah, we’re getting better about having more people do it. And I try to remind people if there are like, I don’t know, sharing something that seems like, “Oh, this would be great to document to remind them like, Hey, this would be great to have in Notion. Why don’t you add a page over in Notion?” Trying to make sure everyone’s doing it.

Jovian: Yeah. I think documentation is really hard. I mean, I’ve experienced it firsthand. It’s really hard. Just like you mentioned, sometimes you’re just like small nuts, right? “Hey, can you just put this on Notion?” Because it’s not second nature for everyone to put this. I almost feel like there should be like documentation as a service thing. Like okay, here’s the whole shit, like here’s my company. Can you just create a whole Wiki or process out of this and then outsource to everyone because it’s really hard. Even we struggle from it from time to time, if not almost all the time. I’m sorry to say this, but yeah, so cool.

Fred: Yeah. And it’s hard if it’s like, you know, sometimes you think like, Oh, we should have a page for this and, you know, you kind of have a very rough draft but it’s not like…

[crosstalk 00:33:10.753]

Fred: Yeah. Should you still post it just to like, I don’t know, just to have something out there or is it to add because it’s not really done? I don’t know.

Jovian: Yeah. My personal issue or personal problem with Notion is that, just like you mentioned, like, okay, there’s this thing. Should I create a whole page about that, a whole section? Should I create a table in there? Should I create a chart? You know, I love Notion though the problem is that there’s so many options there because it’s so vast is something you’re not sure.

So I want to move on to the, I think my favorite topic whenever I talk to leaders in the podcast is leadership itself. So, you shared some of your past emails to your teammates about some of their… Well, first is this decentralized leadership stuff and about your $1 million mistake. Right? I wanna start with the $1 million mistake first. Can you elaborate a bit more about why was that and why did you decide to write the email and send to every of your teammates and what crossed your mind back then?

Fred: Yeah, so this was back when I was still doing all of our inventory ordering. And we were kind of in the middle of redesigning all of our products. This is when we started hiring a lot of people and we were really rebooting the whole company. So basically what happened in the process of that is the new products, newly redesigned products, new website, all that was ready for a launch in the fall. And the sales of the old products we were, you know, trying to time them so it would sell out just as the new stuff launched. But that timing didn’t quite work out. So we basically had a bunch of inventory of the older products leftover as the new ones were just about to be ready. So we did a big discounted sale, sold off as much of them as we could, but we ended up having to sell some through Amazon. And it just basically dragged out instead of us being sold right when we wanted to, we were selling for another 6 or 12 months kind of in some different places. So, it was just wasted money, distraction. Obviously, if you have a sale, you know, you’d make less money than you would have otherwise. So, it cost us some money there.

So basically what I did was I wrote an email to the team kind of saying like, “Hey, here’s what happened, here’s what we thought, here’s why I was wrong. Like, here’s what it cost us.”

And the point of doing all that was to kind of lead by example and convey to the team that we should have a culture where like mistakes are okay. But when we make a mistake, we should own up to it, share it with people so that like, you know, we can kind of learn in public and then hopefully, not make that same mistake again. So I wanted to make it kind of like normalized.

So if I can share my mistakes, you know, that one was like a bigger dollar amount than most people will be in a position to make. So like I’m gonna share my mistake even though, you know, I’m the boss or whatever. I made a big one, I can put a dollar amount to it.

So, when you are thinking about like, oh, should I do this, it might cost us, you know, some much smaller amount of money. Like you feel more able to take a chance if it’s like, you know, a smart risk or whatever. We’re always guessing in business. Right? You’re never sure. So, I wanted people to feel okay with like taking chances, you know, making mistakes but have some good process around it so that we weren’t just like screwing up and wasting money. You don’t wanna go the other direction either. Right?

Jovian: Right. I really love this piece because I think this is something that rarely talked about, like how you encourage people to… It’s a very concrete example of how you can encourage your team members to not afraid of taking risks and especially not afraid to make mistakes. And I feel like it’s especially important in remote settings because honestly, you don’t see each other, right? You don’t see each other. I mean, if you make mistakes, I mean, at least in a co-located company, unless you’re a team of 15 people, you’re 10 to 15. But, “Okay. I messed up on this part.” You go through the office, you see your boss face to face. I think at one time you go, “Okay boss, sorry.” And then you can just talk it out. Right. But remote companies, like nobody knows what everyone is doing to a certain extent. So I feel like this is a really concrete example. I really like it. And the email is very well-written. And did you write the email like almost like after the whole fiasco happened or like immediately after that or?

Fred: Yeah, I think once I kind of figured out like, you know, at the time we were sort of trying to solve the problem and all right, “How do we sell these off? Let’s put them on Amazon.” You know, you’re kind of doing the work. And then it was a little bit after that I tried to like, you know, do kind of a post-mortem and figure out like, all right, what was I wrong about here? You know, it started as trying to do it for myself and figure out like, oh, how do I not ever do that again? And then you start making some notes. And then I decided like, it would make sense to share with everyone and it would be a good example of like a very big version then people would feel more comfortable sharing, you know, even small mistakes or whatever. So yeah, it kind of went from like doing some work for myself to sharing out with the team and then later I just posted it on my blog. So, I don’t know, maybe that makes it an even bigger example because I shared it not just with the team but with anyone who wants to read it.

Jovian: Yeah. Do you regularly do post-mortems on, you know, experiments or things that happened and didn’t work out well? Is it something that Tortuga’s team do a lot?

Fred: We do and I’m trying to do it even more, but yeah, we do a lot of, you know, you might run a marketing campaign or, you know, we’re always kind of tweaking different things on the website. So, you know, you can be informed and think like, “Hey, this change is probably gonna work.” But you should still always go back and kind of run the numbers and see if that mattered. So, yeah, we try and do that and then send a kind of summary out to everyone. So, even if let’s say it’s about the website and, you know, we send that out to everyone, yeah, lots of people like that’s not part of their job. But it’s still good for them to see like what other people are working on, what we’re learning, and, you know, there might be something applicable to their work too.

Jovian: I think that’s a really great process to have. And like you mentioned, like, even if other team members to know that this thing started bad, at least they know that this thing ended. Oh, this happened before. And you can like future reference for any other project.

Fred: Like you said, in a remote team, you know, you can announce, “Hey, we made this change” and then no one ever hears anything about it. And if it went badly, you could just like, “Ooh, I’m not gonna mention it”. If it went while you can like talk about it. You know, we don’t wanna be in that habit.

Jovian: It gets back to the whole documentation, the culture again. So another email that I found fascinating that, of course, you shared with your teammates and the world is on the topic of decentralized decision-making and decentralized leadership. Can you share a bit more about that? And again, what made you decide to share that?

Fred: Yeah, and the size that we are, this is kind of going back to the like, you know, the nature of the company and sort of leaning into strengths or away from weaknesses. But yeah, being a team where until recently, we were basically completely flat. Everyone reported to me. You know, we’re whatever, 10 people or so. It’s a hard stage where it’s not like there’s a bunch of individual teams in the company with our own manager and then those managers reported to me or anything.

So it was very easy for me to be the bottleneck for basically everything because everyone was reporting to me. So like, it’s great for me to be able to see and touch like every aspect of the business. That’s nice. But it can kind of go the opposite way too, where like you allow yourself to become the bottleneck because there’s like no one to defer to or no other managers at least.

So, it’s something that we’ve put a lot of emphasis on, especially the last couple of years that, you know, we’ve grown the team, people have been at the company longer, so they are able to make good decisions. So I’m trying as much as possible to keep decision-making at the individual level and providing all the support we can by either me doing it or our general manager and, you know, we wanna ask the questions like we talked about earlier and like provide the guidance to the people.

Sometimes we need to set, you know, maybe a company-level goal or OKR. But as much as possible, like our goal should not be to like have everyone bring all the decisions to us and then us make every decision, but to help the rest of the team make those decisions on their own. Because one, they’re the one doing the work, so they probably have the most information and like I’m trying to remove myself as the bottleneck where I think a lot of small businesses, remote or not, just like, you know, any small business, I think a lot kind of stuck at the stage we’re at where, you know, the founder or the CEO, whatever, you know, they are across the whole company. They do a little bit of everything but then they never figure out how to get to that next level where they like handoff responsibilities, handoff decision-making. And like, stuff happens without them knowing about it or controlling it. So I’ve always been like not worried about it, but just knowing that that can be an issue and trying to like figure out how we’ll work at the next level of the company and try to build for that and not let myself be like the bottleneck and impede our progress for the whole company.

Jovian: Got it. Did you find it hard to do that? Like, not directly making decisions and not having the full picture of everything or it’s more like it’s pretty easy for you?

Fred: It was probably harder when we first started out because it’s like, you know, the company is your baby and it’s very small. And, you know, at that point, it’s like your first couple hires, even if the company is going well there’s still some element of like, uh-oh. If I let other people make a decision, it all might fall apart. And then like, you know, I didn’t have control over our success or failure or whatever. But as we’ve grown we’ve, you know, have kept hiring, have been able to work with everyone, like, for a long time and one-on-ones and working together.

So, I think now we’re at a place where it feels much easier because one, people have been with the company longer and we’ve also just established more of like the culture and how we do things so they can make decisions that aren’t just like one, they don’t think they need me for every decision. And two, they know how to make good decisions without like always needing my help. You know, they’re more equipped or are, you know, doing the work to help equip them to make those decisions. So I think it’s hard when you start out of course, but it has gotten much easier over time.

Jovian: Yeah. I always found this transition from entrepreneur to executive, so to speak, is interesting because when you’re an entrepreneur it’s really hard. You wanna do everything, you wanna know everything. Cool. So my last question, I think this is the first time I ask these questions to podcast guests, I think. So let’s say that you are thrown into a situation to help transition a co-located company to a remote company, whether as an advisor or you work there, what will be the first couple of steps you are going to do?

Fred: Transitioning sounds like it’d be very hard. I don’t know if anyone’s done it but …

Jovian: Exactly. I’m not sure too, yeah

Fred: …I’d love to learn about that process. Yeah. I think the first thing would be, so it kind of goes to a, I was talking to a minute ago about, I’m always, sort of, visualizing like the next step for Tortuga and how we’re gonna look at that stage so I can be, you know, building toward that and not just getting caught up in today. I think you’d have to do the same for a company transitioning to remote and think about like, all right, how does a fully remote company need to operate to work well? And then start installing that.

So I think the biggest thing there would be a lot of the stuff we’ve talked about like communication, documentation, having…like we use Asana for project management, but having a single source of truth where you can go back to and know like, what’s the status, who’s doing what, when’s it due? Because there’s just so much in that communication documentation, etc. realm that like it’s less important at a co-located company or you can just kind of gloss over it and like, I don’t need to like…you know, it’s not written down anywhere. But I know, you know, I go and ask this person if I have a question about this topic. So you can’t quite do that as easily in a remote team. So I would kind of envision how a good remote company works and then just start installing all of those processes even if you don’t like need them in the office version of the company.

Jovian: Right. Kind of like reverse-engineer it for lack of better words. Okay. Fred, again, thank you so much for your time today. It’s been a fascinating chat. I learned a lot from this conversation. And where can people learn more about Tortuga and find you online?

Fred: Sure. Well, thanks for having me. It was a fun conversation and got some new questions. It’s always fun when there’s a, you know, some new stuff to talk about. Yeah, you can check us out. Website is tortugabackpacks.com. And if you wanna see any of my other writing where I write about basically all the topics we talked about today, that’s just at my name, fredperrotta.com. And yeah, check us out and yeah, reach out or email me if you have any questions.

Jovian: Yup. For our listeners, don’t forget to check it out. Hope we can find a link in the show notes. Fred, thank you so much for your time.

Fred: Yeah, thanks for having me.

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