Uncharted Entrepreneurship - hosted by Brent Peterson out of the Minnesota chapter of Entrepreneurs’ Organization – brings you daring stories straight from the trailblazing entrepreneurs who are unmapping business frontiers across every industry. Settle in around our virtual campfire as Brent sits down to pick the brains of startup pioneers, visionary founders, and intrepid CEOs whose origin stories - marked by unexpected twists, lessons, and stumbles along unpaved paths - will inspire your own trek in launching a boundary-pushing venture. Trading war stories, strategies, and even warnings, these audacious guests invite fellow founders and future leaders into their confidential circles in a uniquely transparent, wise, and motivational way. So join us off the beaten business trails to light your entrepreneurial fire!
Bobbilee Hartman (00:22.506)
Yeah. So yeah, my name is Bobbi Lee Hartman. I'm originally from Victoria, Minnesota. So that's how I found out about EO Minnesota chapter. And I now live in Seattle and I've been running lodged out. Originally I started running events in this, in this type of fashion in 2014, but I didn't start lodged out till 2017. And.
I could talk more about that role in a bit, but one of my passions in life would be trail running, which has led me to move to Seattle, doing more mountain running and elevation and gain and back country skiing.
Bobbilee Hartman (01:07.958)
Mm-hmm.
Yeah
Bobbilee Hartman (01:24.268)
Okay.
Bobbilee Hartman (01:47.146)
Yes, I think you should pay for that show.
Bobbilee Hartman (01:55.75)
Okay. Okay, yeah.
Bobbilee Hartman (02:06.826)
Yeah, no, but I like to follow the professionals in the area and, um, do the reps that they're doing and learning a little bit more about the terrain that they, I find it to be fun that they're doing similar train that I am. And so I try to see what the Strava, you know, what they're doing on Strava. And then I'll try to beat it or I just have fun in that way versus being, um, racing a bunch. I kind of raced a little bit when I was younger and I got, um,
Just yeah, kind of emotionally made me just feel not as connected to the sport and just made me shut down and not do as well. But when I'm out there in the wild and just running and competing on my own terms, um, I found to, yeah, just do some really fast times and just get really into it and get excited about it again. So. Yeah.
Bobbilee Hartman (02:57.514)
No, I don't know what that is.
Bobbilee Hartman (03:02.215)
Oh really? Okay.
Oh my gosh. Wow. I've thought of trying to do compete in Europe and doing UMTB. Um, the shorter races, I liked shorter and steep. That's kind of how I train. So.
I don't know if I'll become an ultra runner. And I think that's what's pushed me away also from racing because I love trail running, but I don't know if I want to push my body to the extent that some of these athletes are in these really long distance races, but I like short races, you know, half marathons or less on the train, um, on the trails. And yeah, so there's shorter distances I've now found that UMTB has. So I've excited me to try and compete in one sometime.
Bobbilee Hartman (03:49.015)
Yeah.
Bobbilee Hartman (03:54.025)
Yeah.
Bobbilee Hartman (03:58.56)
Yeah. Okay.
Bobbilee Hartman (04:08.199)
Yeah, so LodgeDownt has changed over the years, but in its current phase that it's in, for the last three years, it's been running off sites for companies, running off sites for entrepreneurs, leadership teams. So anything where I'm not selling the tickets and I'm not marketing it, you're bringing the people, and I'm helping you facilitate the venue, transportation, food, finding unique venues that are
Some are unplugged, that's where Lodged Out came from, was having these off-sites that are no cell reception, no Wi-Fi, but with businesses, everyone typically needs some form of being plugged in. So I've found to what I bring there instead is a super beautiful location that's relaxing, just well-designed, finding interesting boutique hotels that are smaller depending on the size of group.
or finding Airbnbs that are in a beautiful setting, with their style, in a beautiful way. Yeah, that's kind of how I've shifted things. But it started way back in 2014. I was going to tech conferences all the time, and I was finding people were not really connecting with anyone during the day, during the talks. They were kind of on their computer, they're on their phones looking down, not even really listening.
companies are spending thousands of dollars to send their employees there, and I felt that the impact was not, the return on investment I didn't find to be pretty that impactful. But what I did find impactful were going to Q&As, or panels, or going to the happy hours, going to some of the fireside chats, just the smaller setting environments where people were talking more and engaging more with the content. And at the time I had grown up going to summer camps, I had...
growing up going to a trail running. And I just found the outdoors to be, yeah, just totally part of my life and something I couldn't do as much while I was at these conferences away from my home. And so, I don't know, I just was thinking about the two of them together. And I always thought, you know, I always had these big projects I wanted to do or these side projects. And I always thought, hey, if we could all just get together, and that was our only focus that this whole week, we're just gonna spend time on these side projects. That was kind of the first spark.
Bobbilee Hartman (06:20.522)
of an idea that I had was just, if I could just get away and not be distracted by these other things I have to do in my life, I could just finish some of these side projects and I would talk about it with friends and they're like, yeah, that sounds like that's totally something I would love to do too, or learn a new programming language. Yeah, there was this stuff like that was kind of going on in my community. And so I started talking about it a lot with others just at conferences and meetups and I had learned about this group in Australia that had started a...
summer, like a summer camp conference, basically. So there was normal talks and there was normal, it was an unconference, if you will, at, um, at summer camps. And so they said, why don't you just create the U S version of that? So that's kind of how I started. I just met them and I was thought about it for a couple of weeks after I met them. And then I was like, yeah, I'll just start the U S version of this event. And so that event is called rails camp. And I still run that event.
and I sell tickets to it and I promote it, do the marketing, everything, I own all of it. So as I was doing that, it started in 2014, as I was doing that, I found, you know, a lot of my friends aren't software engineers, but they like what I'm doing and they'd love to go to my events, but they just don't find that this is the enthusiast group that they are a part of. So through that time and through just talking to more people, I thought I need to make an umbrella brand around.
this concept that I've created in this community that I've curated. So I'm gonna call that Lodged Out. And so that was in 2017. And when it first started, I was running, I was selling tickets to events. I was promoting events for different enthusiast groups. So the first one was for makers. So people, if you think like Etsy, making things and designers. And then I made it for trail runners, lawyers, entrepreneurs.
and then some companies I was doing custom events for. So that was all before COVID and charging more for these events, nicer venues. They were no longer at summer camps. They were at lodges, boutique hotels. And through that time, I found again that maybe I wanna do more custom. So I'm a little busy. I also was working full-time as a software engineer. I forgot to mention this was all kind of a side project for me, honestly.
Bobbilee Hartman (08:44.358)
in those years. And so during that time, I don't have a lot of bandwidth, so I thought I'll just do custom and focus on custom events and find my own clients and they'll bring the people. So I just have to focus on what I really love, which is finding these venues, curating the whole experience, designing the agenda, making it not too packed so people had time to connect and think and have time for themselves at events as well, which I found that missing in a lot of events I was going to. And that's kind of where it's at now. So that's.
around right before COVID and after COVID, since COVID it's been in the form that it is now, which is the custom events off sites. And sizes of people, I've done five to 150. So, and that's about the size that I think it's a good fit for due to the impact I'm trying to have, which is like building connection in a beautiful setting. And when you get a little bit more than 100 people.
you have to spread them out to two hotels, and they're not typically as boutique anymore, they're quite larger, and yeah, so that's kind of the style, the form that it's in now. And they're all over the US and some in Italy as well.
Yeah.
Bobbilee Hartman (10:20.434)
Yeah, so some of the retreats have been fully off-grid where they actually cannot use their, there's no cell reception and I tell the venue to turn off the wi-fi. So if that's the style that they want it in, then they really don't have a choice. So, and it's been so impactful, the testimonials after those events is just, it's something people have never even done or thought that much about, the impact that it could have. So it wasn't like I had to fight them to take
to shut down, they actually had to. So when it's in a setting where there is cell reception and wifi, it's different because it can depend on what the client wants. They might wanna have meetings where they need to have their computers out, they need to be connected. Or is it a culture-based offsite where they're just all hanging out and...
There's kind of the agenda is designed for activities where they're using their hands or they're there. It just doesn't really make sense for them to be all just sitting at a table on their phones. They'll do that in their own cabins and their rooms, of course, but the agenda is designed in a way that they're thinking less about being on technology because their mind is being used in different ways and they, you know, they're not using it for a distraction. And if the energy in the way that I introduce the event when I get there, I say, I...
presented as, you know, this is up to you. You can do what you want, but this is an opportunity for you to see what it feels like to just put your phone on airplane mode, or I'll tell them that there is no reception at the venue, and they have to expect that. So they prepare their life, they prepare before they get there, you know, they put on vacation mode, or they'll tell their family, you know, here's the emergency number to the venue. All of that is kind of prepared so that when they get there and they realize it works, they're like, well, I'm already...
prepared to be offline, right? So sometimes I've done that for smaller events. But yeah, it just depends. A lot of people definitely don't want to. I've given throwaway cameras and stuff like that so they don't have to take photos with their phone. Or I'll have a photographer there so they don't have to take as many photos. But they don't usually want to actually give me their phone. That's never really been a thing. So.
Bobbilee Hartman (12:38.494)
Yeah, it's usually like if it's not there, then they just can't use it.
Bobbilee Hartman (12:50.482)
Yeah, those 5Ks.
Bobbilee Hartman (12:55.486)
Yeah. Yep.
Bobbilee Hartman (13:07.488)
Yeah.
Bobbilee Hartman (13:15.85)
Yeah. Yep. Yeah. So, um, it's funny you say that because I started to notice that some of the Ruby on rails conferences, there were five case, there were a lot of five case happening and I loved, and I love that. So, um, that's kind of also what gave me the inspiration of adding it or having the, being at summer camps. So they always provide activities. So yeah, I curate activities for people that are, first I kind of asked the client, do you want to be on a lake? Do you want to be near trails that you can just walk to from the property?
I design things in that way if that's kind of what the group might be interested in. So curating different activities and stuff that's off campus. I'll find parks to go to or hikes that are nearby I can drive to. A lot of movement is always built in because they are outdoorsy events typically. So.
If it's on a lake, making sure that there's kayaks or stand up paddleboards, fly fishing guides. I've done ice fishing guides, cross country skiing. You know, there's been these places in upstate New York I love to bring people that are made for cross country skiing and they have trails on the property. Yeah, a lot of things in mind are built into the agendas if they're interested in that.
And I was just talking to a client recently and they wanted to do meditation before certain things. I know it's not like moving your body, but it's definitely like mind body wellness built into the events because a lot of people, yeah, there are a lot of clients aren't just there to talk business. They're wanting to kind of create a unique culture mixed with business. So that's where some of the ideas for activities I've done like beach Olympics.
if it's on the beach. Yeah, pickleball tournaments, stuff like that is kind of the fun you can have with these.
Bobbilee Hartman (15:27.967)
Mm-hmm.
Bobbilee Hartman (15:34.839)
Yep.
Bobbilee Hartman (15:41.79)
Yeah, so I've definitely done a lot of bringing in speakers. So if they want a fireside chat at night or an inspirational talk, that could be in the evenings. During the day, if they need a facilitator, I just kind of, it depends on what the client is interested. If they're trying to learn a specific thing, like everyone at this group or everyone that's here needs to learn XYZ. Maybe it's JavaScript or something like that. Yeah, definitely curated and brought in different.
guides for specific something that they're learning. If it's just moderating something, it depends on the size of the group. If there's someone moderating like, you go in this room, you go in this room, it's typically what I would do by creating the agenda. But if it's guiding conversations, let's say it could be a, I don't know, a therapeutic conversation or a cultural shift that's happening within the company and guiding some of that, I've definitely provided outside people for guiding conversations.
Sometimes people have someone in mind already and I'll curate their travel and figure out where they're, they'll probably stay at the venue and if they don't want to, I'll find something nearby. So coordinating with them or finding it is something that I've done for different types of clients and depending on what they're interested in learning or facilitating.
Bobbilee Hartman (17:21.903)
Mm-hmm. Let's see. I guess in the planning the challenge, or like actually after it's planned, getting them there.
Bobbilee Hartman (17:40.99)
Yeah, yeah. It actually, you know, I would say some of the challenges people...
I would say most of the people that have come are actually excited because it is different than any other event that they've maybe already been to with their company or they're just paying to go themselves, right? So they're just, I think it just actually curates the perfect group on its own sometimes because it's a little bit of a different experience that someone is already kind of seeking something that's different. So they go along with how we're connecting and being at a table and like people are actually talking and they're not looking at their phone.
part of those, I've had like, I brought someone in Montana that was a swing dance instructors. So everybody was doing just something that they're totally not normally comfortable with. And I was like, just do it, it's funny. And like, just grab a beer and like, it's just funny. And I think I have this approach that's very open and I like to try all these kinds of different activities, even though they're just like fly fishing is something that people have never really done. And I found that people.
are connecting in a way that they're all new to some of these things. So they all just kind of connect together, and especially in a smaller setting, they bond. The biggest thing I noticed at these events is they're bonding in different ways because they're disconnected typically, and they're doing stuff that they don't normally do at all in life. And so it's just a funny experience. So you see people open up a lot faster and get close to one another quite a bit faster.
in just two days or three days than they have with any other strangers they've maybe met before, for example, because they're just in an environment that's so different. There's fun examples. But I'd say the challenging thing is sometimes I brought speakers in before and they kind of just come and talk and they go in their rooms and they don't communicate with the group and that can cause kind of a disconnect, you know, because it's like we're not all in this
Bobbilee Hartman (19:45.034)
this is fun, like, you know, so I have had challenges with that. So you kind of have to figure out, find these speakers that want to be there and want to be part of it versus hiring someone that's very famous and bringing them in and they're not part of the, they're not part of what is cool about the magic of the event. So, but I haven't really seen a lot of, I haven't seen a lot of things where, you know, if I love going to the event specifically, if it's larger than eight, for example, going to it and seeing if someone's sitting in the corner or not.
talking as much or they don't feel as extroverted as some of the others. So I kind of create agendas that there's a lot of spaces for people to, if you don't wanna be around everybody all the time, especially if there's shared lodging at some of the bigger events. Yeah, just kind of creating spaces where people have their alone time mixed in. I've learned that through design of a venue, the layout of a venue. I can kind of figure out if this is a good venue or not, depending on the spaces that are.
that it's the way it's designed, making sure there's separate rooms for specific things, a quiet room and a louder room with people on do karaoke at night or something that's louder. Yeah, so those are all things I have kind of in mind, depending on the, I know there's different types of people. I have puzzles that are out, that are on tables, people get there, if they don't feel comfortable, they can just sit at a table and maybe play a puzzle with someone. I've seen a lot of these things that kind of mix into my events due to the different types of people that I know are coming to them.
Yeah, so I'd say the challenge is kind of, they were early in my days of starting these and now I've realized what to do with those types of environments.
Bobbilee Hartman (21:25.656)
Yeah.
Bobbilee Hartman (21:35.763)
Hmm
Bobbilee Hartman (21:43.742)
Yeah, yeah, I love having unconference because again, it's just so much more engaging. People are actually thinking and they're allowing other and the facilitator is good because there's some people that would speak over others or put more ideas than others. So that's kind of good to have a facilitator there. But the creative, yeah, the creative energy that comes from unconferences versus, and also there's some people that would never want to say, hey, I want to speak and tell me they want to speak so I have a set agenda at a conference.
People are, you know, maybe don't feel that they're worthy of some sort of thoughts that they have or ideas that they have, right? So Young Conference has been good for that too, is there's new ideas that people would not normally share, but they feel comfortable because there's just casual ideas that are up there maybe and not such, I know this, you know, like you're an expert in this one thing, but you might not be, you know, and I've had people think of things like, hey, I'd like to teach everybody how to make like,
maple bacon or something, you know, it's like something that's so unrelated to what you would think at a tech environment, you know? So there's cool stuff that comes a bit from that too, that I just didn't even expect. So, and it's interesting because it's kind of going along with when I was talking to Jeff in one of the forums, Jeff Lin, he was saying, you know, we're not just here to talk about business ideas all day, every day. It's, we're trying to become better founders or better...
human beings with our families or with our friends, there's better people overall. So I think that's, it's kind of a cool idea having some of those other ideas mixed in because it is interesting to learn about different things or books people are reading or, yeah, I just think that's kind of what drew me to some of wanting to help with some of these forums because I found that that's kind of the style that these are already being designed in. Yeah.
Bobbilee Hartman (23:45.342)
Yeah, so actually it was in Minnesota. I got an email once from someone completely random saying that I have this venue that I think perfect for your off sites. And it's in upstate New York and I think you should just come and see it. And so that was probably the most memorable trip I've ever had and running all of these. And I've run events at it since. It was in this tucked away old historic lodge that they...
It's run by a university now and they don't really rent it to the public unless there's learning involved. So you can't have a wedding there, you can't have any typical large, yeah, large random event. It's very specific who they let in. And when I toured it, there was, it's on a lake and they have all the different boats and you can go throughout the day, do what you want. There's hiking on property and everything is owned by, it's one of the great camps, which is a famous,
I don't know how many great camps there are, but they're all from the large families of Vanderbilt's. And yeah, I can't think of all the different families, like old money families. And they own these lodges in upstate New York and in the out east. And yeah, I just got to tour it and there's a chef that's there that lives there. So there's a large area for group meals and all the rooms have these historic bedding and walls and furniture. And
Everything about it, there's so much history. There's old bowling alley that's there. And in the back of the property, there's another hidden place that they don't rent to anyone. It's just for families now, but it's another beautiful venue that's just, it's as if you step back in time. And these old little restaurants, it reminds me of the Boundary Waters up in that area, Minnesota Boundary Waters. And there's these old little fishing little stops where you can go.
You can buy your bait and get sandwiches and it just has this totally old Minnesota charm to this whole area. And yeah, it just was the, I can't even describe it. It's just this tucked away on its own private lake. And that's kind of the exact experience that I'd love for everyone to have at some point in a lodged out is to bring them to these private lake, private experiences where you tucked away and there's no cell reception and you're totally.
Bobbilee Hartman (26:06.354)
immersed in nature, but you're also in a cozy place. And there's something about, I really love finding venues when there's not any shared property lines with another property. So it's either just the woods or maybe there's like a national forest next to it where you don't really see anyone else but the group that you came with. And I think that's kind of when I started to really see the power in that. And so that's kind of the venues I try to choose. If a...
If a client is open to that, some like to be near a town, they can walk to restaurants and everything. But if they really wanted to do the special secret that's out there, there's these really beautiful venues that have that experience where you're totally just immersed with this group. And yeah, so that's kind of one of my favorite venues ever. I think they've had some photo shoots there with Vogue and different stuff like that, but it's pretty off the grid and pretty secret. And it's just one of my favorite experiences was kind of
getting someone who's from Minnesota find me and knowing this would be a cool experience. And then they, and then it happened to be in New York. So yeah, that was just one of my favorite experiences.
Bobbilee Hartman (27:29.85)
Yeah, I guess I'd love to, if anyone is interested in working with me for their EO retreats and help, I can help you find different Airbnb's. I think that's the best style for the size of groups or small boutique hotels where everyone has their own cabin. And then a big, you know, a nice meeting space, everyone can hang out. That's kind of what my goal is to work on more EO forums this year and helping with any catering or private chef or.
restaurants that you'd like to go to if you want to be near a town. Um, but yeah, if anyone's looking for some interesting and more boutique experience and, um, doesn't have time to work on it, I'm here to help.
Bobbilee Hartman (28:14.518)
Yeah, they get a hold of me. So lodgedout.com or my email, I can put in the description, but it's bobbylee at lodgedout.com. And then, yeah, that's how we can start working on the bid. There's also a form on the lodgedout.com slash offsites, the offsites page. There's a form you can fill out that asks a few questions about, you know, how many nights, how many people, dates they have in mind, a location you might. If you don't have location in mind, that's okay. I have locations.
that I've used in different vendors and partners that I work with all the time. Yeah.
Bobbilee Hartman (28:53.536)
Yeah.
Bobbilee Hartman (29:01.077)
Oh really?
Bobbilee Hartman (29:05.307)
Oh my god. Really? Okay, I was like, okay. No, I don't know.
Got it. Got it. Ruby. Yeah. No, Ruby is language too. So I was like, Oh, maybe. I mean, obviously Ruby is built a rails built on Ruby. Yeah.
Bobbilee Hartman (29:29.062)
Yeah.
Bobbilee Hartman (29:38.635)
Yeah.
Bobbilee Hartman (29:43.338)
Great. Yeah, thanks so much.