Jared (00:00:02) - The more the world goes remote or hybrid, the more important it is to get people together in person. Strategically, at its core, like we are still humans and until we're all part robot, or until robots take over the world, like we are going to have this innate desire to connect with others and that is going to happen in person.

Ariana (00:00:24) - Welcome to Secret Ops, the podcast uncovering the world of operations, one episode at a time. I'm your host, Arianna Cofone and today's guest is Jared Kleinert, the founder and CEO of Offsite, a company that helps businesses to plan team off sites. Now operators…if you're like me, you have definitely been involved in off sites. If not planning the entire thing from end to end. And as much as I love an offsite, I also know how much hard work it is to put in the effort to make it really fantastic. Now, Jared, this is his expertise, some other things that he has from his background. He's a TEDx speaker, a three time award winning author, and he was also voted as USA Today's Most Connected Millennial because he's helped organize hundreds of events for over 30,000 attendees.

Ariana (00:01:17) - So big or small, he's experienced it, let it, facilitated it, given talks about it. And we're going to learn a lot from him today. So let's jump in. Jared, thank you so much for coming on to Secret Ops, especially because we get to talk about one of my favorite topics…offsites. What is an off site? Why do we do off site pro tips from the expert himself. So just want to thank you so much for taking the time to come on.

Jared (00:01:42) - Yeah, thanks for having me.

Ariana (00:01:44) - Before we dive into all of my really granular questions, because, you know, I'm going to nerd out. Let's start with your journey into getting here today. So how did you find yourself founding a company and leading a company that just essentially does end to end of everything with an offsite? Talk us through it.

Jared (00:02:03) - Like all great companies, it started during the big pandemic of 2020. Yeah. Offsite is a pandemic company for sure. About a year into the pandemic, we started working on what became Offsite, sort of betting on a few different trends. The first is that I hypothesize most companies were going remote or hybrid and felt that way before the pandemic as well. I just think the pandemic pushed us into the future 10 or 20 years, but thought everyone was going remote or hybrid as a byproduct of that. I believed every company would plan an exponential number of off sites. Off sites have been planned for decades now, even for office first companies. The word came from going off site, away from your office, mostly reserved for like executive teams or maybe a sales team that outperformed. They got a fancy trip out of it, and then the third bet was making, or realization, was that there was no software to make offsite planning easier. And from previous experience, I knew that planning offsites sucked. So it's like we should have software to make this easier. And that's typically a good way to start any software company is if you can make something suck less, then it might be a good company. And so those were sort of the the bets. The reason I came to think that those things would happen is because I had a decade of offsite related experiences before the pandemic happened, about 12 years ago, I was one of the earliest employees at a company called 15 Five, which is one of the leaders in employee engagement and performance management software today. A few hundred people in a distributed team, but they were remote first like 12, 13 years ago. So I attended offsites as an employee at a company that used their own off sites to build their own award winning culture. And then I had a seven year run of being a speaker, author, consultant, right? Was able to do some Ted and TedX talks that led to a lot of corporate keynotes. So speaking at all sites that led to facilitating executive team retreats in particular, because various marketing teams in the Fortune 1000 wanted to learn how to market to millennials..

Ariana (00:04:22) - And can I actually ask…having been a speaker and a facilitator in those settings, what would you say are the biggest differences and the biggest challenges in switching with those roles?

Jared (00:04:32) - I think I was a good speaker, but was probably more on the content side, which lends well to facilitation. Facilitation is mostly about the content and the outcomes of a meeting. Like it doesn't matter how entertaining you are, other than to maybe get people out of their ruts or get them to engage with each other. Pay attention. But it's really about the outcomes in an executive team meeting and what you're actually benefiting as a result of bringing in a facilitator. So. Different skill sets, but sort of learned by a trial by fire. And so the last off site experience I had before starting the company was I ran summits for entrepreneurs for about four years before the pandemic, bringing together like 20 to 40 people at a time for three days. Did that for almost four years. So I ran 14 of these meeting-of-the minds summits and basically planned an offsite end to end.

Ariana (00:05:31) - It seems like a common thread is is human connection and communication for all of these experiences you have, because you've also written books as well. Speaking, facilitating now literally rethinking how to help others present and facilitate off sites that seems to be just like a magnet for you.

Ariana (00:05:49) - What do you think draws you to that? What do you think it is about, I guess, connection and communication that gets you, I don't know, into that world.

Jared (00:05:58) - I think it was a chosen zone of genius. And then something invested in at a very early age. My zone of genius is bringing together people and ideas to accomplish bigger things for society, and the only way I even got to understanding what is genius was how to articulate it or what might be for me was working with the founder and CEO of 15 Five. His name is David Hassell, and I was very fortunate to just cold email him when I was 16, offered to work unpaid in exchange for his mentorship, and ended up spending two years at this startup, which you know now is a client of ours. Dave is an investor in Offsite and is really the one of the origins for all my work now but I guess I had some choice in the matter of emailing him. And lots of hard work. Listening to whatever advice I got, but I don't know a lot.

Ariana (00:06:52) - I don’t know a lot of 16 year olds that were just cold. Email somebody and be like, yo, I'll work for free. Can I get into your world?

Jared (00:06:58) - Yeah, I just sort of read about David after a negative mentor experience. The article was about him being the most connected man you don't know in Silicon Valley, meaning that he had all these connections to amazing athletes and individuals like Tim Ferriss and, you know, different startup founders, host dinner parties, like, people look up to him. But yeah, really, really, it's just in the right place at the right time. Learned from David about the power and benefits of networking, community building, etcetera, and then decided to double down on that because I wasn't particularly interested in learning technical skills. Like maybe at 16, I could have learned how to become an engineer and coding and all that, but was sort of betting that I would get farther by learning social skills, than learning technical skills. Hopefully that's going to work too, because, you know, now we have ChatGPT that could code for you.

Ariana (00:07:55) - I feel like it's advantageous. You know, I think back in the day, I grew up with a lot of like my grandparents. So a lot of it was about human connection and talking over coffee and, you know, like coffee cake. And it was very face to face. You had to learn how to talk to adults, to kids, to anybody. That was kind of how I grew up. Same with my husband. And now you sort of see generationally there is that gap, like there are some people that don't have those social skills in that way because we are so digital first. And that is quite interesting actually, for thinking about off sites, because you have a lot of people that are meeting and building relationships digitally, and then they're meeting for the first time in person. So I guess let's go into the trifecta, because I think this is a perfect transition. So trifecta in operations…people process, technology fueled by data. And when it comes to the people part of putting all of the pieces together for an off site, I guess let's start with how do you bridge the gap in types of people and how they function, how they get engaged? Like how do you even approach that?

Jared (00:09:03) - Yeah, you got to pick the right people to join. We do advise in thinking through maybe a cadence of off sites. So do you want to have an all hands meeting once a year? Quarterly executive team retreats…maybe 2 to 4 department level off sites throughout the year? Sort of. What structure are you putting around your program for off sites? That's depending on how big your company is, if it's fully remote or if it's hybrid, like how distributed your team is, what sort of budget you can allocate or willing to allocate. It's a lot of factors, but yeah, we can advise clients on that. But really it's about all the facilitation points. So your job is to get the right people in the room, our job is to help make sure that that interaction and those experiences are going to be as high ROI and as possible and as engaging as possible.

Ariana (00:09:53) - But there is that need. Like once they feel what's happening within those off sites, they want to know when the next one is, they want to understand the next time they can come together and have that sort of thinking process or facilitation. It's a little bit different than their day to day. Do you find that most people, when it comes to an off site, gravitate towards wanting more? Do you have some people that tend to want to, like do one and time of year four times a year? Like, what do you see in your world?

Jared (00:10:21) - I would say most employees are opting for more off sites than less. And then companies are realizing the benefits of creating some structure around a program of off sites. A lot of our clients have been through a pretty tough downturn in the last year and a half, two years, so they're kind of also coming out of that and figuring out what they can and can't afford. But if there's the ability to invest in it, most companies are trying to have their employees be at a company offsite once a quarter. That would be ideal. And that could be again, like you attend an all hands meeting once a year, and then if you're on the sales team, you might do a sales kickoff in Q1. You might, you know, hopefully you're a top performer and you get to go to a presence club event in Q2. And then maybe there's like another mid-year check in and then you have your all-hands and, you know, late Q3, early Q4. So you get to go to four off states a year. This is something that Airbnb has rolled out where Brian Chesky, back in April 2022, was like, Airbnb is going to be fully remote now. And if you work here, here's some seven tenets of how we're going to do this. Subject to change, of course, but I think number four out of his tweet thread was that you'd be going to lots of off sites, and he sort of pegged this idea of once a quarter or more as a frequency for going to various off sites at the company. And then I also read recently, the founder and CEO of Dropbox, Drew Houston Housing…is a very New York thing to say. Let's go with…let's go with Houston, Texas. Some left.. You know true Houston slash Houston has, I guess, this unofficial 90/10 rule where he says 90% of your time working at Dropbox should be remote and 10% should be at a company offsite. So that equates to, you know, 20 something business days a year if you sort of like, take out weekends and holidays and then you sort of do the math, it's like, oh, that means you're probably at an offsite, you know, once a quarter for 3 to 5 days at a time. So that's a magic wand scenario, you know, is probably 3 to 5 days at a time once a quarter. But it really depends on the makeup of your team and the size of your company as well. And so a company like 15 Five today, you know, a few hundred employees, they might have 20 to 30 off sites that they plan, but there's like one all hands a year quarterly executive gangs or like even board meetings. And then you have product teams and marketing teams sort of doing their own thing. But hopefully, you know, you're giving a playbook internally, giving tools so that people know what they can spend, what sessions they should be running. And no one does this particularly well. Not even the pioneers.

Ariana (00:13:22) - Yeah. Talk to us about that. This is more the process part, you know. What do you think people really get wrong about planning an off site and like you said, like how do you reorient their playbook based on best practices that you've learned over the decade plus that you've been doing this?

Jared (00:13:37) - Process…I think we're all just figuring it out on the spot and starting to come to some basic frameworks. There are some companies that do this really well. Some of the pioneers in the space that inspired Offsite were Automattic, which owns WordPress and Tumblr, and a few other companies like that. They're now one of our corporate investors as well. And so they have 1200 to 1500 employees now.

Jared (00:14:06) - And so they've built playbooks. But some of those playbooks have broken as they've scaled. But, you know, they do have a company wiki internally. And that company wiki will share policies around sort of what you can spend per day per attendee, maybe some communications that you could send out around these off sites and so on and so forth. So they do a really good job of that. GitLab is another example, a pioneering remote first company. I believe they're the first fully remote company to go public. And they also have just a very extensive public company wiki on everything, including various off site formats, and that has worked for them. I think you're not really doing all hands meetings at their size, but you're doing maybe regional meetups of a few hundred people at a time. So think running a… doing a company wiki is probably a good idea for any remote or hybrid team in Notion or wherever. I'm sure you have other episodes on that.

Ariana (00:15:15) - I love a wiki. I adore a wiki. Where do you end up taking that? Because like, obviously you've got some companies that have best practices with off sites, what they do, how they do it. Let's say you lovingly get a client that you don't have that established framework, or maybe it's kind of a hot mess. How do you start to reframe what an off site should be about? What's the spirit? What's the structure like? How do you begin that process?

Jared (00:15:41) - Yeah, even with the companies that have like internal wikis, I think there is an opportunity right now to educate people on what an offsite is and an opportunity for us to put technology in place. Your third piece of this…to figure out over time what our better processes and maybe like, who are the right people or how do you better have those folks interact with each other. And so we're now developing some data as we're working across hundreds of companies. And so we're starting to come across these frameworks like you will likely spend 2 to $3000 per person per off site. So when you're thinking about an annual planning framework and budgeting, we've now come to understand, you know, like the 30 line items that you know are going to take up 98% of off sites. Maybe there's like a straggler here or there that has a very unique line item in their budget that they need to add, but we can we have built templates. Maybe we can put in the show notes like, you know, how to build a budget for this. And so yeah, we're coming across some budgeting frameworks. We're coming across a framework of cadence. And then you know sort of all the factors that go into that. And then really trying to educate people on sort of why are you having an off site in the first place? And so there are business objectives tied to certain off sites like strategic planning. So you might have an executive team retreat once a quarter to do your quarterly planning, do a retro the past quarter, you know, go into the next quarter and find your OKRs. We're actually starting to build templates around certain operations playbooks. Right. Like there's the scaling up methodology. There's an entrepreneurial operating system. And some of those books have basic off site frameworks in that. And so we can actually go a step further, create templates around that, and then help clients like find the right place to do it, build out the entire agenda, take care of all the logistics, etcetera.

Ariana (00:18:00) - Which like I just want to note here, that is no easy task. It is. It looks deceptively easy because like, listen, the experience when you get to an off site, everything's arranged. You have the hotel, you have your food, you have your agenda, you have your meeting room, you have your screen to present on. You have your deck, you have all of these things. You've got notecards, right? All of those little pieces have to be coordinated, defined. It's like, it's so crazy if you haven't planned one yourself, how much all of those details actually play in..even welcome kits!

Jared (00:18:14) - I have some fantastic people on my team.

Jared (00:18:17) - Yeah, yeah. Yeah I'm sure.

Jared (00:18:19) - I do this for clients day in and day out. As we're recording this in early November. We have three off sites happening around the country right now this week and barely knew which clients they were for or what's going on at the off sites, which is a great thing because then we could focus on that–

Ariana (00:18:33) - Yeah, that means that something's going well.

Jared (00:18:35) - Yeah. The team crushes it, and we put processes in place on how to plan offsite clients. We're starting to share more and more of that publicly as content marketing and thought leadership. Then also we have great engineers that are trying to turn that into software bit by bit.

Ariana (00:18:51) - Yeah, talk to us about that. The technology piece that you're building out with the team.

Jared (00:18:56) - Yeah, I mean I envision a world where we can have this be fully automated or sort of create the Canva of the space where anyone can plan an off site on their own and leverage all these best practices, just like you would use Canva to do some design work on your own. Or if you ultimately want to hire like an off site planner through us, or hire an event producer through our marketplace, then we're giving them all the tools to take care of you. Just like designers will go into Canva and do work on behalf of the client. So there's a whole ecosystem of software we can build for this. The first piece of software we decided to build, which is unique to other competitors…we decided to build a marketplace where you can find essentially every vendor that you need to plan an off site. And the first vendor that we really focused on was your venue, which is typically a hotel, a resort, meeting space providers. We decided to start there because that was the hardest. That was one of the biggest friction points to get started, and one of the hardest parts of planning an off site. And it dictates about two thirds of your budget. And so we decided to focus on that.

Ariana (00:20:10) - That’s a beast to focus on too.

Jared (00:20:13) - I had this experience personally where I was trying to figure out where to bring clients, and I tried big Airbnbs, I tried photography studios, I tried hotels, I tried boutique mom and pop hotels, and I tried Fairmont properties. And they all had different ways of working. Like the contracts were ridiculously challenging. And even if you wanted to book with them, it was very painful to find the right contact through their website and then to talk to their sales manager, and then a separate person for food and beverage. Like it's just a total mess. So we basically built Airbnb for off site venues to start. We've partnered now with a few hundred hotels all around the world, and you can make an account at Offsite.com. Then you could click into any of the profiles, check out all the pretty pictures and all the basic information like meeting space and you know, the room sizes and number of restaurants, distance from airport, and then within 24 hours, we expect hotels to get back to you with a detailed proposal and with a 20% or more discount because you're booking through Offsite. So that's been really cool. And, you know, anyone can use it. It's getting better sort of week by week as our sprint cycles are happening.

Jared (00:21:34) - So just adding in every category over time, like photographers, videographers we do all this for clients. Now we're just sort of turning it into software. So we'll be on that train for a while. Because building software is hard and building a marketplace is an entire business that's like Airbnb, Thumbtack, they're all marketplaces. Those are gigantic businesses. I do think–

Ariana (00:21:55) - I was going to ask you. Like, what do you think has been in that first stage? What do you think has been the hardest or the biggest learning curve in starting the marketplace feature of this? Yeah.

Jared (00:22:08) - Well, we had a bigger vision at the very beginning. And so I think one of the biggest lessons learned for company building and for building software is really to narrow scope and focus. I mean, the very or originating story vision for Offsite was to sort of do the end all, be all software platform, but to also have physical Offsite campuses all around the country. And so at one point, I was under contract for 20 acres of land in upstate New York and was going to basically build a hotel, you know, and it was like meeting with general contractors and like, you know, city officials in Bethel, which is like two hours outside of New York. Where Woodstock took place. Fun fact, um, but thankfully got out of that lease and just focused on software. And then with software like, we will ultimately build some off site planning tools, which is where some of our competitors have decided to go, things like an agenda builder feature, like how we can turn that into an algorithm? A budget builder feature. Like, we can help you build a budget based on what's in your agenda and where you're going and like, pull data, like you don't need chatGPT for this stuff. Like you just need to build a good old fashioned algorithm. But yeah, then there's a few other features I can envision there. But, uh, as easy as it sounds to say that, like, that's an entire company as well. So we just decided to focus on the marketplace, build that out. And then within the marketplace, like there's a lot of things that have popped up that are surprisingly difficult. The main thing is the RFP process between a user and a hotel and just there's so many different edge cases that can come up. For example, if you're planning a offsite for 100 people, but your executives want nicer rooms, and then you want your, you know, like executive assistant or your chief of staff to show up a day or two early to sort of, you know, lay everything out, like how do you automate different room types and, you know, different attendee counts in what should be an automated process back and forth. And so those edge cases propose a lot of interesting challenges. And then at some point, we'd like to make this fully automated, like real time pricing, real time availability. But hotels have a very antiquated system around, like the different booking platforms they use. It's not like Expedia or some of those other travel providers where you can get real time pricing and availability on individual rooms, like once you go to eight rooms or so on most of those platforms, it becomes a different type of booking rather than just like an individual room or multiple rooms.

Jared (00:25:00) - You're a room block and then they're trying to sell you meeting space and food, beverage and so I do think at some point you can sort of fully automate this so you can like go on a website, be able to book a 20 person room blog with meeting space with get the price in real time. Book it. But that day is not today. But you know, we're figuring out all the different reasons why that's not possible and then trying to solve for that. And so that's pretty interesting. And then just getting data around like where people want to go, what places, what types of places they want to go to, and starting to sort of build our supply around that has been super fascinating. So yeah, just endless lessons to learn.

Ariana (00:25:45) - Endless lessons, I think…so operations tends to become a catchall within businesses because oftentimes we are spanning across the business. Right. So any time that there is a larger company initiative, we tend to have our hand in it in some way, shape and form, which is why I've gotten involved a lot in off sites, not necessarily because I want to, but because it's kind of de facto in that operations umbrella.

Ariana (00:26:09) - And I'm just imagining operators listening to this thinking like, oh my God, I never want to research hotels again, or oh my God, I never want to research spaces again. This in itself, I guess what people don't understand in planning an off site is the amount of time it takes to do all these things.

Jared (00:26:27) - Oh, you have an executive assistant. You have a chief of staff, head of people, head of options into this screaming in their car like, yes, yeah, sorry about that. So right. Like I just want to apologize on behalf of CEOs everywhere that you have become the catchall for off site planning. I would not be surprised at all if this became a full time role at various companies in the future. I've seen a couple like Head of Remotes and sort of roles around that, but I would not be surprised whatsoever if there was a dedicated off site planner. So we tried to sell into I've seen like a head of events or an internal events team, but I would argue that even the kind of events they use to plan or plan now are fundamentally different than an off site, especially if you're fully remote, hybrid, you know, or very distributed. And so yeah, sorry, sorry. I'm sorry about that I'm working to make it easier for you. Yeah.

Ariana (00:27:27) - Well, this is also when you were talking. We were talking about the cadence, you know, annual versus quarterly versus, you know, all team versus individual teams. What inevitably happens that I have found is then people are like, I love seeing everybody face to face. When's our next meetup, when's our next hangout? And then all of a sudden you're we're like now doing social gatherings and like me as an operator, like I just want to automate things and, like, make people's lives easier. I don't want to be planning events. And I do think you're right, because as resource has been taken off of rent being in office, that can be allocated now towards different roles, like like you talked about having someone that just oversees offsites or just oversees these more social components of work that are very important for employee retention, for communication, for alignment. Like it might seem frivolous at surface level, but it's actually not.

Jared (00:28:19) - I feel like you were in the pitch meetings with me when I was talking about why Offsite should exist.

Ariana (00:28:25) - Yeah. It's because you know, I've seen it, though, and maybe, you know, you can speak to this too. I have been in a room where nobody has seen each other face to face, ever, and they've been working together for a year or two years, and you inevitably have that moment. That's like, I thought you were taller. I thought you were shorter, you know, like, oh my gosh, like. And then all of a sudden you start to see a bond happening that you can't almost verbalize what's going on, but it happens on all the cues and the body language in the humor and the jokes and all the in-between moments that you don't have necessarily baked into a virtual environment. And that's where maybe I'd like to go behind the scenes talking a little bit about like, you know, what? People don't know. And I think part of this is virtual versus in-person. You know, the work that you're doing, obviously, you're building this marketplace to help make this easier, more virtual, more digital. But the off sites that you're planning are in-person. Why do you think being in-person for these is so important?

Jared (00:29:24) - Yeah, I think it goes back to the why you would plan an off site. And so we kind of touched on strategic planning, which is very aligned with what a lot of ops folks will have a hand in, in sort the of rhythm of business conversations. There's team building, which is sort of a phrase thrown around. But, you know, that is an important reason for having off sites as well. There's increasing cross department collaboration, there's employee retention, there's employee alignment, there's sort of innovation and brainstorming, which might be really good for marketing teams or even like engineering and product teams. There's all, you know, there's like client facing events where you might want to do a multi-day event for VIPs that you work with or customer conferences. So there's all these different reasons to have an offsite and most of those things are just better to be done in person versus virtual like, that's kind of the answer at the end of the day. Yeah, that's at its core. Like we are still humans. And until, you know, we're all part robot or until robots take over the world, like we are going to have this innate desire to connect with others, and that is going to happen in person. And actually, you know, I think you and I would agree, like the more the world goes remote or hybrid, the more important it is to get people together in person, strategically. And so I believe there's so many benefits to remote work from the individual lifestyle standpoint for employees and sort of access to opportunities for employers. It's access to talent around the world. There's productivity benefits if you're doing it right. It forces you to communicate better as a leader, to build a company wiki and, like, get people on the same page. But there are challenges to running a remote or hybrid company because it's really just around managerial challenges, like managing people's hard. Managing teams are hard, all the problems that make it hard are just harder in a remote or hybrid setting, because we're all still figuring out how to do that, and even the pioneering ones in the space have only done it for ten, 15, 20 years relative to like thousands of years of in-person work. So virtual events have their place like we do, maybe a quarterly happy hour sort of thing. But the “why” behind that might be to celebrate a new employee being added to the team. Or it might be to give everyone a break if we've all been working so hard. Those are the sort of the lower barrier of why to have a virtual event, but for the important company-building, foundational elements of your culture, those are all going to drive to in-person experiences, and if not, then you either should just have a culture where it's very clearly outlined that this is async. we never have meetings. We do this in a certain way, and it's very transactional. But some people like that and it could be very high, highly productive. And then, you know, that's going to be 2% of companies. So 98% of companies are going to be, you know, with humans and people that want to see each other, uh, that may otherwise feel lonely at home if they don't get to see colleagues or have human interaction, they want to benefit from their own ways of working. You know, being able to access opportunities around the world, all the benefits. But like they also crave that human connection. And if you don't give it to them for long enough, like they're one click away from starting to look for another job, and you know, that's going to get more expensive to replace folks and train them up versus investing in off sites where, you know, at minimum, you can retain top talent for another six months a year because they have like a fun trip to Miami to look forward to in the winter. Or, you know, you can actually build upon those connections and like during the harder moments when they're feeling lonely or something's happening at home that they need to vent about, like they can message a trusted colleague, like, feel a kinship with someone else, hop on video. And it's a much better experience because there's more trust, there's more intimacy.

Ariana (00:33:52) - A point I wanted to touch base on because, you know, you're talking about it helps with teamwork and collaboration and communication and all of these things that I cannot stress are insanely important. But the problem that I have found is how do you quantify a return on investment for this type of off site? And this is where especially a lot of the times when I'm working with small to midsize businesses, they might not have had an off site ever yet. Right? Like a lot of them have been founded in the last couple of years after 2020, this is still a virtual land. So how do you and your team approach talking about the return on investment, like how do you quantify those things that almost feel unquantifiable?

Jared (00:34:36) - I think the cut and dry way to do it, if you've never done it before, would be to look at what you previously spent on office space, you know, in-office lunches or snacks and all the associated costs, and then think about reinvesting it into a cadence of offsets. And what you'll find is you are likely saving money by planting off sites. Versus what you used to pay sort of per head to have in office. It was like some companies…like it wouldn't, it wouldn't be unreasonable to be spending $500 or $1000 per person on office space every month. When you consider rent, you consider furniture, you consider utilities. All that–

Ariana (00:35:23) - So costly. It's so costly.

Jared (00:35:25) - Lunches, snacks…

Ariana (00:35:27) - Oh my gosh.

Ariana (00:35:28) - Yeah.

Jared (00:35:28) - The you know, happy hours events you might have done. So you're spending, you know, in the before times. You're probably spending $10 to $20,000 per person annually on office related expenses. And now you have a world where you can spend 2 to $3000 per person, per offsite. And even if they go to the quarterly offsite, like maybe you're investing, you know, $8000 a year per employee, you're pocketing 15, 20% of what you were spending otherwise. While having this amazing perk to leverage in recruiting, which has, you know, a positive ROI. If you want to calculate that you're getting better team members, you're getting people that maybe you've been able to localize what you're paying them. You know, whether or not that's a good practice, it's like another person's episode and expertise. But, you know, there's probably.

Ariana (00:36:27) - We’ll get people ops in here. Don't worry.

Jared (00:36:29) - Yeah, it's probably other savings to be had there. And then that's just brass tacks. Like then we could start talking about all the things that are a little harder to measure, but things like an employer net promoter score. And is that increasing over time? That is something you can track by doing surveys. And we recommend our clients do that before an off site and then after an off site. And then if they have a cadence of offsets, they can sort of do it regularly and see over time if their employer net promoter score is going up. We also recommend various like, connectedness to colleagues scores and like connectedness to company scores. And I'm sure you have your own employee metrics that you can bake into this. You can use tools like 15 Five or Lattice or Coltramp and layer this in, but that can start giving you a set of data over time to think about the ROI of off sites as well. Then you get to some of the sort of higher end stuff, like how do you measure trust and intimacy and like whether that goes up or not.. Whereas like sentiment analysis tools that Slack has and so I haven't played around with it too much. But we, we use the thing called Geekbot for like daily asynchronous check-ins. And I know that they have like they have the ability to read Slack messages and give you emojis on how happy or sad or you know, normal your team is. And so I know that there are some sentiment analysis things you can utilize. I'm sure other softwares have layered on to that. And so there's also like you can see how many messages were sent to like two months before an offsite and then two months afterwards. I'm sure there's ways to see like collective meeting minutes in Zoom or huddle like a Slack huddle or there's like a new company called Rhone that you can sort of check that, check all that data out. And, and so I think over time, like you can track those sort of things as well. And then like if, you know, people trust each other more, like it's probably going to be palpable and visible. If everyone's more aligned on company culture, that's going to be apparent and hopefully you'll hit your KPIs. It's hard to know if you would have like better OKRs from an in person executive team versus a virtual executive team retreat, but I think most of us would probably bet that you'll get better debate and discourse and, you know, understanding from an in-person, offsite.

Ariana (00:39:09) - I think so. What I've seen with virtual OKRs like deciding on virtual OKRs versus in-person OKRs, is that the OKRs become editable a lot more frequently versus when you set up OKRs in person. I found there to be pretty hot discussion about them, right? Because you have a bunch of experts coming in with their expertise saying, “no, I think this is what it should be”. And you hash out a lot of those things that maybe virtually doesn't really work. So then what happens is the next quarter they’re shifted a little bit, then they're shifted again. And then everybody's kind of like, what are we aiming towards here? Like I'm confused. What are we going towards? But that's again that's like a small kind of case study with the clients I've been working with.

Jared (00:39:51) - Yeah. You can even think about the like why? Why connect virtually versus in person at all. You know, virtual connections have a lot of benefit for saving time and money. Like we didn't have to record this in person, and each take time out of our day to travel and commute and money to do that. Same with a salesperson hopping on a call or on Zoom like they don't have to travel like my grandfather did. You know, in the country to do like, wholesale jewelry, you know, shout out grandpa.

Ariana (00:40:24) - Isn't that crazy to think about? Just think about encyclopedias. They used to come door to door and, you know…I mean, we had one of those, but, like, it's just so much has changed so quickly.

Jared (00:40:34) - But then what are the benefits of in person? It's it's like it's being able to humanize someone that leads to building trust. You know, even one interaction with a client in person today can endear you for 6 to 12 months. And that's true of a team member as well. Like it's very refreshing for me to engage with my employees whenever I get to see them. And like, I will go out of my way to go meet new employees in person. And, you know, we play in off sites quarterly, and it's for no other reason than just, you know, build a deep, meaningful relationship so that you can do all the tactical stuff later on. Virtually, asynchronous, I'd say the other main reason is like if you're having a difficult conversation, like you're probably gonna want to do that in person, like you're breaking up with someone, you should probably do that in person versus a call, you know? Or like your doctor is going to tell you some news in person for better or worse.

Jared (00:41:33) - And like, you know, ideally, if not, they'll call. Like the last thing they're going to do is text you or email you like that's the worst because you can't pick up on body language, voice indentations, all the things that lead to, you know, deep connections. And so if that all happens in person, like the same is going to be true to company. Like if you're having, you know, challenging decisions at the board level or, you know, at a leadership level about what you're OKR should be for the next quarter, or like what your plans should be for the next year, you're probably going to have to duke it out in person and ultimately come to an agreement on what's best for the company and that's just more efficient in person and will lead to less editable OKRs that people will follow.

Ariana (00:42:15) - OKRs!

Ariana (00:42:17) - Can you tell that drives me just slightly crazy.

Ariana (00:42:19) - I guess the last question in this section before we do a little wrap up is if the operators are listening and they're like, Jared, I'm always planning these damn things. And I just I just don't know. I don't want to anymore. What would you say is the greatest pro tip of offsite planning that you can give them outside of just working with you all?

Jared (00:42:43) - I was gonna say just go to offsite.com.

Ariana (00:42:46) - What would you say is something that they should just kind of put in their back pocket when they're at that stage that they've got to plan the off site. It's on their plate. What's a pro tip to give them?

Jared (00:42:55) - I would try and templatize this as much as possible. And you think of it as sort of building blocks like you're going to need certain capabilities in a hotel or in a venue. And so you can come to understand what that is going to be for your company or for the certain types of off sites that you're planning. And then you can sort of programmatically ask for that with venues. And so you'll come to know that you need a certain number of rooms in your room block. You're going to need a certain number of nights.

Jared (00:43:28) - You're going to need, you know, one big meeting space and then three breakout rooms and this basic AV package. And then you just sort of keep that as a template. And then that makes it easy to go message various venues. I would recommend another pro tip, you know, negotiating and planning ahead. Definitely those two separate pro tips. But planning ahead.

Ariana (00:43:51) - You get three for the price of one.

Jared (00:43:53) - Planning ahead will help you with negotiating because you may not have dates locked in or even a city locked in. And then you could message various venues and have them give you the best rates possible on their calendar. You can also pin hotels and venues against each other and ultimately save more money. And so if you have that template, it'll just make that back and forth a lot easier and help you plan ahead because you know exactly what you need. Same with an agenda. Not that you’re going to have the same agenda every single time, but you're going to have some travel in and travel out time. And so those are building blocks you can replicate and adjust based on how far people have to travel. You're going to have some sort of welcome dinner or welcome activity. You're going to have your morning setup. We recommend an optional workout in the morning and then time for breakfast and then some sort of icebreaker and like intention-setting. And then, you know, we sort of have a whole way to build the templates that we give publicly. And then use was to play an off site, even like ending each day on a high note and then ending your entire offsite on a high note, so that if and when people are, you know, debating on an important issue, or if things get heated, like there's a way to cool off and like enjoy each other's company and then like end the offsite on a bang so that, you know, they think back to the experience fondly, you know, 2 or 3 months afterwards,, it's all these building blocks even like, you know, one that might be overlooked is adding lots of flex time into the agenda so that if you're running late on a session, like you're not ruining the rest of the agenda. Also, like, people might get exhausted. So giving them the opportunity to have unstructured social time with each other, that's typically when some of the best conversations happen is organically, but then also like letting people take a nap or call home, or go do a workout or something like that, or explore wherever you're traveling to. Maybe people don't have the opportunity to travel and this is a cool experience for them. So it's a lot of building blocks. So just like Automatic, GitLab Offsite has done, if you try and template these experiences, it'll save you a lot of time. And it'll be easier to even delegate this to team leaders or to other people planning an offsite at your company. Because you are like, here's the playbook, do it. Don't ask me to do it. I'm busy.

Ariana (00:46:20) - Totally, totally. That's a lesson I've learned. Also, the point that you made about having flex time. My gosh, I've learned that lesson the hard way. You definitely, definitely want to have flex time. And I think that when you have social time, that's when flex time is extra important. Because if things are going well, socializing is happening. People are connecting. They don't want to stop and you don't want them to stop. That's the whole reason why you're meeting in person and so you want to bake that in. That's such a good point. Jared, we have to wrap up with some questions about you as a human being so that we know a little bit about yourself. I'm just going to throw them out. You just answer what first comes to the top of your brain. So the first one is what is your favorite part of the day?

Jared (00:47:07) - Probably the morning time. Not that I have a strict morning routine, but I have building blocks of a good morning. And yeah, like getting a little run in. I love coffee. I Have like four cups a day probably. And yeah, just like getting into it.

Ariana (00:47:24) - What is something that makes you little-kid happy? I guess, besides coffee. Now that we know that you love coffee.

Jared (00:47:31) - I'm a big basketball fan, so I follow sports religiously. Probably waste way too much time on ESPN, but I'm a diehard Miami Heat fan and love checking in on the games and all the storylines. Like, yeah, I spend too much time on this, but I played as a kid and it's an outlet for me, I guess. Question mark.

Ariana (00:48:01) - What book are you currently reading or what audiobook are you listening to?

Jared (00:48:06) - I'm finishing up a book called $100 Million Leads from Alex Hormozi, who's like one of the top internet marketers. You know, internet-preneurs right now. Seems super cheesy and internet markety as a person, but like, has some really good content. I don't know him personally, but learning a lot from that and then trying to look at my desk. I was finishing up Five Dysfunctions of a Team from Patrick and Lenzioni. At some point I may want to have my team go through that with me. And that was also taking some elements of that and putting it into an agenda template that I published a couple days ago, which is an executive team retreat agenda template.

Ariana (00:48:54) - Nice. Well, this is the next one. This is not a normal rapid fire, but as a three time published author yourself, what would you say is the hardest part about writing a book?

Jared (00:49:04) - The mistake made with my first two books is having a non-commercially viable title. So my books…I'm biased, but I think you've all been really good to read. But people do judge books by their cover. And so like my first book was called “2 Billion Under 20. How Millennials are Breaking Down Barriers and Changing the world”. And like 2 Billion under 20 is cute slash creative. If you consider that there's 2 billion people in the world at or under 20 years old and like trying to inspire the generation, but like, no one knows what that means. And then I did it again with 3 Billion Under 30. Um, so my third book, I called Networking, it is about networking. And so, yeah, I don't know if that's the world's best title either, but like, definitely spend a lot of time thinking about your title and your cover if you're going to write a book. Uh, and then with Networking, I decided to write that book because I had a decade of podcast interviews, articles, online courses I'd attempted to create around networking and relationship-building was like, “oh, it'll be easy to have it all transcribed and put into a book”. But then I wanted to write a book that people would read and like. You have to not only have good content, but you have to make it entertaining, like back to the sort of speaker thing. And so adding back in anecdotes to bring the book to life, and then adding in interviews and ideas from other networking and relationship-building experts. There's like all these layers that I added in that hopefully made it a good content to like, good book. And so I think that's something I wasn't thinking about beforehand.

Ariana (00:50:51) - I just took a bunch of tips away from myself, put them in my back pocket. What is the best purchase you've made under $50?

Jared (00:51:00) - my back hurts right now, so I got, like, tennis balls that I'm using as sort of like to, like, rub my feet on. It's like when you're in pain, you know, a it’s nice adjustment. Uh, before you get the adjustment with the chiropractor. Oh, $50. I mean, I run through headphones, so maybe should just spend more than $50 and get, like, great headphones. But I'll spend money 3 or 4 times a year on, like, $15 to $20 headphones. I'm sure you have better answers. What maybe that's more practical is like, uh, the cable that you use to charge your phone. I have, like, eight foot long, you know, cables. And so—

Ariana (00:51:43) - That’s a great one.

Jared (00:51:46) - I don't have any around me, but I've got the cube that you have and then have like these eight foot long cables and so and I'll use them to travel or whatever. So that's amazing to just like be able to charge someone and have a bed or like go to a hotel and be able to just survive and thrive.

Ariana (00:52:03) - Totally. That's actually reminding me what I need to get. What's the most important lesson you've learned so far in your life?

Jared (00:52:14) - These are hard ones? Uh, maybe go with, like, most things or figure outable and like there's not any…there's very few, like, truly irreversible decisions. And so that brings with it a lot of humility and also a lot of confidence. So like running a company, it's like you just make the most educated guess you can about a certain direction to bring the business. But like you can always change the OKRs, you can change the business name. You can change like most everything about the business, including all the employees, you could replace yourself if you wanted to. And so. I don't know if we can curse on this show, but I can give you my new favorite saying.

Ariana (00:52:59) - Go for it.

Jared (00:53:01) - I've been jokingly saying lately that I don't know shit about fuck and don’t know fuck about shit so like, literally, we're all figuring it out. Which is also cool because it's confidence-inspiring that no one else knows what they're doing. And so why can't you be the one to build that company or run that marathon or do whatever you want? So I've been able to take on some cool adventures, like starting new hobbies, like jujitsu a year ago, which is part of why my back hurts. But that's been a lot of fun and I didn't grow up thinking I would do that. I've run ultramarathons. I've, you know, started businesses like did Ted talks, blah blah, blah, but like, those are all things that other people have done. And like you can do it too. And like it also is humbling because even if things are going amazingly well, like something tragic, challenging can just be on the other side of that. Like I'm 28, a time of recording. I've been both married and divorced, like didn't expect to get divorced when got married, but like that happened. And then you just deal with it. And so yeah, whatever I said two minutes ago, I'll stand by it.

Ariana (00:54:13) - That’s so good. Sometimes you just have to take that leap and just know that you can just try it and you might fail, figure out that's okay.

Jared (00:54:19) - And yeah, very few things are irreversible. That's what I said that I thought might be smart.

Ariana (00:54:28) - And the last question here for the rapid fire questions is what do you want to be when you grow up?

Jared (00:54:35) - I think I'm doing it like…I’m an entrepreneur, and I don't think I'm going to stop anytime soon. Like, I think all the personal and professional challenges I've had in, you know, my early years and like the relative, like everyone has, like I would gladly take my life back if like, everyone put their cards on the table and challenges and whatever and like, would pick up my problems again and, you know, run with those. But, you know, for whatever challenges we've had, I love running a business, and I think it'll just make me a more savage entrepreneur when I'm in my 50s and 60s. And so I definitely am doing what I want to be when I grow up. And I'm just really excited to see where I can take this current business, and then what lessons I'll take to the next business as an operator. See what I did there?

Ariana (00:55:31) - I saw it. Yeah.

Jared (00:55:33) - Trying to figure out the hobbies on the side, like keep doing random cool things that have interested me so that I'm not so one dimensional. And I want to be able to look back on my life and have a cool life resume that includes writing lots of books, I guess, and doing these ultramarathons. And maybe one day I'll get a black belt and jiu jitsu and like, I've joked with friends about learning music production and not just DJing, but actually, like, making beats. Like, who knows, maybe I'll do that in like five, ten years.

Jared (00:56:04) - Like, I have no idea. But everything's figure outable, I'll guess.

Ariana (00:56:07) - Everything is figure outable. Now, before we officially wrap up, if people are hearing what you're talking about, they're resonating. Everything you're saying is resonating with them. Where can they find you? Where would you like to point them?

Jared (00:56:22) - Yeah, you can email me Jared@Offsite.com if you have interest in working with us, happy to give you a 10% discount on your first contract with Offsite. Just tell us that Ariana sent you or Secret Ops on you. You can just go to Offsite.com for that. We also have free to use software in that marketplace so you can work with us for planning, or you can use the marketplace like you would use Airbnb and happy to have you there either way.

Ariana (00:56:55) - Amazing. Thank you so much for coming on and talking about this topic that I feel like goes under the radar but is so, so important, especially now in today's world. Just thank you.

Ariana (00:57:05) - I really appreciate your knowledge and your expertise and your humor.

Jared (00:57:09) - Thanks for the rapid fire questions. You have me questioning every aspect of my life now.

Ariana (00:57:16) - Yes, I even let you go on some of the harder ones, but we'll come back to them for part two, part two. We'll do the next round. And of course, listeners, thank you so much for listening to Secret Ops. Please remember to follow us wherever you find your podcasts. We're also on YouTube now, and check us out at secret-ops.com.

Ariana (00:57:34) - We'll see you next time.