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Retreats in Remote Work World

Jared Kleinert is the founder of, a company that plans retreats that can save you time, money, and stress. Jared is also a TED speaker and is recognized as USA Today’s most conceptual millennial. He has written 3 books and his insights on entrepreneurship, networking, remote work, and offsites have been featured in major media such as Forbes, Time, Harvard Business Review, Fortune, NPR, Fox Business, and more.

“There’s never been a one-stop shop for all things offsites and team retreats, so why not build it?”

Jared KleinertFounder of Offsite


Welcome to Building While Flying, a Sasha Group podcast where we interview business leaders about how they tackle challenges, stay resilient and navigate ever changing skies. Jared, thanks so much for joining us on Building While Flying. Yeah, thanks for having me. Awesome. Jared is the founder of Offsite, which is a company that plans retreats that can save you time, money, and stress.

Jared is also a TED speaker and recognized as usa Today’s most connected millennial. Uh, Jay has written three books and his insights on entrepreneurship, networking, remote work, and offsites have been featured in major media such as Forbes Times, Harvard Business Review, fortune, npr, Fox Business, and More.

So Jared, I wanna start off by just asking about. The origin story of offsite, you founded the company in January, 2021. that was almost a year into the pandemic. So I think, I’m curious if you think back to that time, was launching offsite, a reaction to the pandemic, kind of accelerating the normalization of remote hybrid teams, or was an offsite planning company always in your mind and then, and it just kind of coincided that that’s when you got.

Yeah. Well, thanks again for having me. It’s a mix of both and so I, I like to say that it’s 10 years of my life’s work before the pandemic mixed with some shower thoughts I had during the pandemic. Yep. About the future of work. And so. When I was a teenager I, I started my first business at 15.

We don’t have to talk about that, that didn’t go anywhere, but 16. I started working for a company called 15 five which are one of the leaders in employee engagement and performance management software today maybe like 250 employees, like close to a billion dollar evaluation. I was fortunate to be one of the first 10 employees there just off a cold email that I sent to the founder.

Read about him in Forbes. He was . Called the most Connected man you don’t know in Silicon Valley. And he hadn’t even launched the company publicly, and so I was just trying to work with him. Started working with, with him off a cold email, like offered to work unpaid in exchange for his mentorship.

And found myself at a remote first company 12 years ago that planned offsites for the team. So we got together in person and they were a company that helped other companies with things like employee engagement, retention, and alignment. And so, got that experience. When I left, I took a seven year speaker, author, consultant, turned to my career.

Ended up working with New York Times best line authors as a marketing consultant like Keith Ferrazzi, who wrote the book alone and, and startups and whatnot. Then I wrote some books. The books turned into speaking. Uh, The speaking turned into facilitating, and so now I. Going to offsites and, and conferences as a keynote speaker, and then as a facilitator for like executive teams in the Fortune 1000.

Yep. Wanted to learn how to market some millennials and like all that fun stuff. The young, young person card I was able to play. And yeah. So then right before the pandemic I had a company called Meeting of the Mines, which is like, Gary Vayner truck’s four D’s experience, sort of a mastermind event together entrepreneurs once every three months.

And I found myself basically doing what we do for clients now at offsite where I was finding venues that were inspiring and marketable, you know, to my clients. But you know, for offsite, they wanna market it to their employees, get them excited about. I was negotiating discounts with the hotels.

I was managing some travel for myself and my team. I was planning an agenda hour by hour. I was facilitating, I was connecting with attendees months before, months afterwards. And so, during the pandemic all these sort of experiences came together and I recognized the trend of remote and hybrid work where 12 years ago, Less than 10% of companies were a motor hybrid.

Yep. The pandemic, maybe it was 20% and then it became 80% of companies that were a motor hybrid after the pandemic. At least that was my, my bet. And so, yeah, decided like a company like offsite should exist cuz every company’s going remote. They’re all gonna plan offsite. Those offsite are gonna become really important.

And there’s never been a company out there that’s like the one-stop shop for all things offsites and team retreats. So why not? build it Got it. Yeah. So, I love the fact that you were building something that was useful to yourself with prior company, and then that became kind of the. The offering.

Right. I always love talking with founders and it’s almost like what would you have taught yourself five years ago with all the knowledge you have now, and then built a service or a company kind of around that knowledge you’ve gained around that. So, could you maybe dive in a little bit to what the business model looks like?

Is it a flat fee for services? Is it a percentage of a total project? Like what is that ultimately, like how did you, I guess, arrive at at what that was gonna. Yeah, so it’s a flat fee. We charge $250 per person, per offsite. And scale that up or, or scale it down if you have a lot of it, right? And then we do end to end offsite planning.

So we help you with your venue, with your travel on the ground travel support, planning the agenda, hour by hour helping you find all your non meeting space vendors like photographers, videographers, speakers, facilitators, activity providers. So, yeah, pretty simple. And we decided to do that as opposed to taking a percentage of total spend because we wanted to be on our client’s side in multiple negotiations as opposed to trying to like artificially increase the spend.

So right for the saving time, money and stress comes into play. We gotta save money and pay for ourselves, otherwise no one’s gonna hire us. What you kind of just described of that the curated experience that you’re bringing to clients, was that something that was always at the heart of the business or was that something that you kind of realized you needed to formalize that while you were building the company? long term, uh, We’re sort of building Airbnb, you know, a curated marketplace. Venues and other vendors with a platform like Rippling or Canva that gives you everything you would need to plan without us.

So I think the business model is going to evolve over time to more of a SaaS or like subscription model. Yeah. But we started as a hundred percent service and then moved to sort of tech enabled service, and then now we’re building software. And that has its own challenges, but there are a lot of benefits to doing that move because you’re learning like what to productize in building software.

And then you’re learning the business model over time as you’re talking to clients and figuring out what’s valuable to them. And so it became pretty clear from a software standpoint that the. Pain point was finding venues for the offsite. nothing happens unless you find your hotel, your meeting space.

Like you can’t book flights. You can’t find your photographers videographers unless they’re willing to travel, but it’s cheaper to find ’em local. You can’t plan activities like you have to find where you’re having it first. Without offsite, you know, for example, or a marketplace like offsite you know, you might be emailing like info, some random hotel.

You’re gonna start Googling and like find hotels that have great wedding experiences or good, like personal experiences. Yeah. But the rating systems aren’t built for offsites and like business group travel even like the Expedias of the world aren’t built for groups of larger than eight people, for example.

And so we decided to just build the marketplace side of what we’re doing first. And we’ve, you know, recently are recording this in like early April 2023, like two or three years from now. But we’ve, we’ve been pri prioritizing all things marketplace. And so now we have over 200 hotels. So we’ve signed a master service agreement, so pre-negotiated.

Discounts and favorable treatment and all that. And then we built out like the marketplace for speakers and facilitators. Kind of like our own speakers bureau, I guess. Yeah. And then we have you know, a partnership with SwagUp to do your swag. We have partnership with a company called Allflight to Book Flights and just thinking like all the different vendors that you might need.

While we’re still doing the agenda creation, the budgeting service, all that as a service. So we’ll eventually come back around to building the rest of the platform. But I guess the, the lesson here is the service and starting without expensive software engineering and, and all that, like taught us what to build and hopefully that’ll save us time and sort of getting to market with our sort of grand vision.

you brought up a point I wanted to touch on today at some point, which is this kind of the, the rise of tech enabled service and looking at industries that historically have been localized or relationship based or, you know, old school yellow pages. Just like Googling, what’s the least expensive kind of option I’m thinking of like moving and things like that.

Like there’s been a couple different. You know, companies that have come along that have built that kind of layer of tech enabled service. And so what advantages has that given you to kind of bring that mindset to the event planning, but then even within event planning niche kind of category of, of company o corporate offsite Yeah. There, there’s a lot of like startup axioms and like isms that are worth listening to. Maybe, maybe over drinks one day. I’ll tell you all the things I didn’t listen to. Like I wanna hear about those too. Yeah. But you know, sort of the doing things that don’t scale idea or. Finding the fastest way to make money to prove out a concept.

I think that is one thing we did right. And I try and continue to do with the team in terms of launching like new pricing options or, or things like that. And so the name of the game at the very beginning of offsite was to see if we could get someone to pay us to plan an offsite. And we could have built a website, we could have built technology, could have done all these things.

but The real answer is like, will someone pay us? You know? And so, right. Yeah. Back when it was, just me and, you know, the co-founder at the time we just pitched a couple people. They gave us money and we started planning an offsite, like we didn’t have a website. We had nothing to show other than just like the.

Two page contract of like, Hey, we’re gonna do abcd and e. And I was leveraging my network. I was leveraging, I guess, past planning experience with meeting of the minds and things like that. But we were just trying to prove if someone could pay us for that. And so I would a hundred percent recommend that.

With any type of business, even if it’s a complicated software that you’re envisioning, like what’s the simplest version of delivering that and then what’s the fastest and simplest way to get someone to pay you for it or even do a deposit or, or something like that. Because it’s one thing for someone to say they want what you’re offering, it’s another thing for them to vote with their euros or and so I think we did that right.

Our industry is SaaS which is software as a service. Yeah. But, you know, it makes sense to start with the service and then turn it into software and Yep. There’s, there’s pros and cons to that. But I think it allowed us to get to market faster with initial clients get some case studies outta that for marketing purposes.

And then as we talked about earlier, like learn what software to. And hopefully save some time and and money there. And so I imagine in those early conversations, some of that was around getting people to think of investing in offsites as a nice to have to a must have. And some of that might have just been the acceleration of remote hybrid working that is made the need to kind of get together part of your business operations.

But, but I imagine still most people think of that as well. How can I do. In the least, you know, the least cost or maybe people think that like, oh, my business is too small to invest in an offsite. What, what messages did you use to over overcome those hurdles?

How did you kind of break down some of those, those barriers as as they were coming up? Yeah. I think another thing we did well is we chose the right type of client to target. And this is something I saw 15 five do really well. They. Whether purposely or by happenstance they chose to work. A certain stage like startup, for example, that was high growth.

Or, or just a small business, doesn’t have to be startups. But they worked with companies that were 10 to 20 people now, but could be 200, a thousand people in the future. And so we have done the same thing where, you know, our initial clients were 20, 30 person companies. But like our first ever client raised a series A.

Double their headcount and suddenly one offsite became a whole year’s worth of offsites. we were able to help them build the cadence of offsites and actually teach them how they should schedule this. You know, our, our second ever client was a marketing agency that like has also doubled in the last two years in headcount.

Third client sold to Plaid, you know, which is a massive you know, FinTech company. And so we just chose our client profile pretty well. And you could do that as a business owner, right? Like you could choose who you wanna work with and who you want to. So I think choosing that clientele intentionally.

Something that we did well, I did it well with my marketing consulting firm in my late teens, early twenties. Like my first ever client was a number one New York Times bestselling author. And it doesn’t matter what he paid me, it doesn’t matter what I did, just you was able to go in, do work, get a case study and, and build from there.

And so I would definitely recommend that for other business owners. And just cuz you are a year into your business or two years into your business, doesn’t mean you can’t do the same thing, but with. Product or different offering or, or packaging your product in a different way. And so we’ve been able to grow with our clients.

Right now, I would say 10 people or more is where it makes sense to start planning an offset. We do have some office first clients, but a vast majority of our clients are remote first or they’re hybrid. Yep. And they’re already feeling the pain points associated with not doing offsites. If they aren’t It’s hard to build trust.

It’s hard to build comradery. Yep. It’s hard to do strategic planning. It’s hard to solve pressing problems. You might lose top talent if you don’t keep them engaged cause they can just open up another tab on their computer and. And if you know companies, those are, for the companies that aren’t planning offsite regularly or at all.

For the ones that have planned offsite, they’re probably already sold on the importance of planning offsites, but then they’ve done it themselves and like they’re chief of staff, executive assistant, head of people just spent 50, a hundred or more hours while doing all these other jobs and just hated their lives.

And so the pain’s really high for us to, to go and. Sort of take that stress away. Or they just see that we’ve done it hundreds of times, and at most they’re gonna do it, you know, four times a year, 10 times a year for larger companies at a department level. So we’re just getting better at it, you know, like chat c, pt, and, you know, we’re the AI for offsites if you want a quotable.

Yeah. So we’re love it. You mentioned being intentional about who you’re going after with prospects. I’m curious kind of where your best leads come from and how you’ve cultivated those. Has that been through referrals? Has that been through? I, I know you’re pretty active yourself on LinkedIn. You know the, is that through company social channels?

where do you feel like you’re kind of best sourcing? Yeah. About 60% of our business is outbound actually. I think that’s also part of choosing an ideal client profile. Yep. For us, we were able to identify what titles people are gonna have. there are negatives to targeting like venture backed startups, but one of the benefits are we can see, you know, if they raise the series A or like that’s public info in most cases.

And we can. See if they’re remote or hybrid because we can just go to their company profiles on LinkedIn and like look at their employees. And if one’s in New York and one’s in Chattanooga, Tennessee where you’re at Yep. You know, Miami, then like they’re probably remote. So, we’ve just developed a easy to target client profile.

And so then I, I started doing some outbound emails and that started working. So we did more of them and then we sort of ramped it up to having an outbound SDR service that we hired, and then we hired an SDR full-time to sort of Yep. Replaced that service. And so we just experimented with a couple different marketing channels, but found one that was working and, and started to scale it up.

Now I’m trying to do that with. Different marketing channels in sort of a founder led marketing capacity. And so now a lot on the inbound ones, like channel partnerships content seo, which is longer term. And like we, we bought, which was not cheap. Wanted to do that as being part of the SEO juice.

And. Yeah. You know, social media, like there, there’s a bunch of like organic options we’re, we’re playing around with, but then also referrals going into a business with a network, like a, a founder market fit they talk about. Yep. And having your network align with the industry you’re in is important.

I speak at conferences and get leads that way. Yeah. So we’re, we’re just playing around and, and trying to figure. Awesome. Well, I think one thing we’ll talk about maybe offline is, how do you scale that on the content side, right? With social and like you talking about how you’re speaking at conferences, how do you capture that and then turn that into content that you can be using on social and, and helping to build the brand that way.

Cause I think there’s a lot of opportunity for y’all there and just kind of what I was, was looking at. But I’m excited for y’all for that. I’m curious as well to hear about. 

Are there sectors or industries that, that you target or that you at least gained insight on? I kind of had, I had this idea when I was researching the company and learning a little bit more about y’all that like, is offsite one of those companies that can be like an, a leading indicator on like the health of the overall economy?

Like if people are booking more offsites, is that like a, showing that the economy’s doing well in these, but I’m just curious if you’ve got like market level knowledge, sector-based knowledge just by. Thinking about how people are allocating their, the demand and budget towards offsite needs. I, I hope we get there at some point.

I think, I think offsites are still so new that it’s one of those like to be determined things. I will say that in the last. Year tech companies have been hit really hard by the macroeconomic circumstance and that is our main clientele. And so we’ve been growing through it, in part cuz we’re new.

And like the amount of companies planning offsites the first time is, far greater, you know, than the ones cutting offsites. Yep. There’s definitely some pain and so like maybe. 3, 5, 7, 10 years from now. Like, we can be the bellwether to see like, or the’s going down screwed. But I, I think there’s some macro trends here like.

Commercial real estate’s being tormented right now. That money is going to things like offsites or hiring remote, which then leads to planning offsite. And remote and hybrid is, is not going away anytime soon despite what maybe Apple wants or Meadow wants and so, Elon Musk gonna fight me on this, but hopefully, hopefully I’ll win.

Yeah, hopefully he doesn’t tweet at me. But no, I think that, I think the workforce, I think he’s busy enough, but I think the workforce is speaking pretty well. I mean, we are a, we’re an agency that is built on collaboration among people and, a we proved through the pandemic we could do this remote first when we had to be, but we have now kind of settled more into a hybrid model where, We would lose talent just straight up.

People would quit if we said, you’re gotta be in office five days a week. And so now we have taken that more hybrid approach. I don’t think we’re ever going back. I don’t know if the ad advertising marketing industry, I, I agree. I hope that we’re not just handling the logistics of offsite planning, but that our clients today and the ones in the future view us as extensions of their team when it comes to building amazing company culture.

Kind of what 15 five does for their partners, where they, they become so invaluable, so sticky to running an effective company and, and sort of increasing employee engagement, alignment, retention, that you’re never gonna drop them. And so, yeah, that’s what I’m most interested in. Like I’m, I’m most interested in seeing offsite becoming a connection company and becoming part of the tech stack of running a remote hybrid company.

You use ramper bricks for your expenses, use a sauna for project manage. Nokin for your wiki and then you use offsite to connect your employees. And so that’s my hope. And you know, in the meantime, like we’re planning really fun offsite, so that’s uh, those worst things in the world. Absolutely. I do wanna hear you mentioned, I’m in Chattanoogans, Tennessee.

You’re in New York. I spent the first part of my career in New York. And you’ve got a large part of your team that’s based in Chattanooga. I’m curious how. You found them, how that happened? I mean, obviously you’re a remote first company, but and so people could be anywhere, but the fact that they’re all, they’re in my shared backyard is, is interesting to me.

Yeah. We, we live in a relationship economy and so, yep. Our second employee, Andrew, who’s our, our head of engineering I met him about a decade ago through the teal found. Bunch of young people coming together a couple times a year who either dropped out of college or thought about it, or Yep.

Didn’t go, like I, I never went to college myself. And so we knew each other since our, our teenage years and then sort of kept in touch over time. Yeah. Not very closely but sort of knew of each other. We’re sort of tracking each other’s careers and then was able to convince him to join us at offsite as employee number two and like the first.

Engineer. And then he built his own, you know, friendships and relationships in Chattanooga. And so when we had the opportunity to hire some of his very talented friends, you know, he just coaching them left and right from uh, you know, that’s amazing. Attractive companies in Chattanooga. So do y’all do offsites in Chattanooga?

We haven’t done an offsite in Chatanooga yet. But I go to When you do, you’ll hit me up. Yeah. I go to Chattanooga like quarterly. You, and, and maybe that’s, that’s like another nugget. Anyone listening is like, if you are a leader of a team, you’re running a company, like it’s on you to get on the plane, like go visit your key people.

If you’re not hosting an offsite, But let’s get the benefits of remote and hybrid work for, you know, 95% of days. But then there’s 5% of days and conversations where it has to happen in person. You have to, you know, invest in your relationships and that lasts you through some of the more difficult moments of running a company or life in general.

So yeah, we, we we do have a nice Chattanooga team. Love it. We have team members in Spain and Canada and, you know, throughout the United States, Puerto Rico. And you know, I, I just love my team and we’re able to hire yeah. You know, anyone who’s awesome wherever they are, and I love that they’re all in beautiful places so that you can go visit them for those 5% of days.

You have to go into nice places. Yeah. Next, next. Offsites in. Yeah, exactly. Awesome. My last question is, kind of a question we ask everyone, which is around, you know, when you’re Building, While, Flying it’s important to keep calm under pressure or you think about like a pilot’s checklist that when something you know goes wrong, they, they kind of immediately get, stay calm and work through.

And so when you’re backs against the wall and you’ve gotta make a tough decision for your business, what’s that kind of internal pilot checklist for you that helps you? Get through it. I dunno if I have a checklist that I run through, like in the moment, but I do a lot of work to prepare myself for the moment if that makes sense.

And so, maybe unorthodox, but I’ve started doing jiu-jitsu okay. Uh, Five months ago and like, In class. I’m literally, you know, someone’s literally trying to choke me or break my arm or leg, like tap beforehand. But like you’re in pressure and, and so I’m getting a much worse experience in class, you know, three times a week versus running a company.

And so that’s prepared me. I also run ultramarathons like once a year and purposely under train and have it be just the worst day ever. But you don’t know. I’m gonna finish. And so I, I do some crazy stuff to like build mental. But, you know, something that everyone could do or, or may want to do is yeah, an executive coach.

And so, I’ve been working with an executive coach for many years. And actually a couple of our investors are also executive coaches, so I, I like pull them in for sessions. Sure. And, you know, I, I share with my team so I don’t wallow in the experience alone. You know, I get smart people at the table to solve the problem with me which is sort of the whole point of meeting in minds and.

Why Yep. Offsites are so important cuz you’re getting everyone at the table to solve pressing problems and then scale the solutions and, and run better companies. So that’s kind of why offsites like my life’s work at the greatest scale cuz this whole meeting of the minds concept of getting diverse minds at the table to like solve the problems.

Is what happens at an offsite, just for companies for nonprofits. So, yeah, I think getting a coach you know, bringing smart people to the table to solve the problem with you, that’s something everything can do. And then if you want to take it to the next level, like, you know, train for yourself up, juujitsu.

Yeah, beat yourself up physically, ultra marathons in Jisu. I love it. Awesome. Well, thanks so much for joining us, Jared. And, and next time you fly down to Chatanooga, we’ll we’ll meet up in person as well. Yeah, absolutely. Thanks so much.

Thanks for joining us for Building While Flying today. I hope you learned as much as we did. We’ll meet you right back here next time for another flight.

Welcome to Building While Flying!

This weekly podcast is brought to you by Sasha Group. We’re the consultancy meets agency arm of the VaynerX family of companies. We help ambitious companies build strong brands that flex with the times through strategy, branding media and marketing.

In ever-changing times, businesses and brands have to shift and adapt. And across all sectors, there is an air of experimentation. Business owners are trying new things out in the wild;  building the plane while flying.

Our pilots, Katie Hankinson, Mickey Cloud, Maribel Lara, and Joe Quattrone will be talking to a diverse range of business leaders and founders. They’ll explore how these guests tackle various challenges while staying resilient and committed to growth. Through these real-life examples of strategies put into practice, we hope to inspire you to experiment and develop your own strategies as we all navigate these uncertain times together.

Importance of Retreats in Remote Work World.

Jared Kleinert is the founder of, a company that plans retreats that can save you time, money, and stress. Jared is also a TED speaker and is recognized as USA Today’s most conceptual millennial. He has written 3 books and his insights on entrepreneurship, networking, remote work, and offsites have been featured in major media such as Forbes, Time, Harvard Business Review, Fortune, NPR, Fox Business, and more.


In this episode of the Building While Flying podcast, Jared joins Mickey Cloud to explain how he scaled his business. He gives some insight into its beginnings, why he prioritized service before software at first, and the unconventional ways he keeps calm under pressure.

In-flight topics:

  • The origin story of Offsite
  • Their business model and how it will evolve
  • Prioritizing service over software
  • Choosing the right clients to work with
  • Could Offsite be a leading indicator of the health of the economy?
  • …and more!

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