Welcome to Invest in Yourself, the Digital Entrepreneur Podcast. Join the podcast mogul Phil Better as he interviews successful entrepreneurs that make their living in the digital world. Now, let's join your host Phil Better and his special guest today on Invest in Yourself, the Digital Entrepreneur

podcast. Welcome back to another exciting episode of Invest in Yourself, the digital entrepreneur podcast. I am, of course, your host, Phil Bitter, the podcast mogul, and today's guest is someone who is taking adventure to a whole new level. She's the mastermind behind unforgettable experiences, blending travel and personal growth in ways that leave a lasting impact on all who attend. As the founder of Wandering Roots, she's created life changing retreats for women across the globe, empowering them through exploration and connection, both but that's not all. She's also a mentor to entrepreneurs, helping them design and host their own highly profitable retreats. So get ready for an episode packed with inspiration and insight because today, we are thrilled to welcome the incredible Anna. Anna, welcome to the show.

Thank you. Thank you for having me.

I am very excited to have you. I'm all I I don't know a lot about retreats, other than, you know, going on a vacation and, you know, enjoying the treats of the vacation. So I'm very happy to have you here to learn all about what you've done and what you're doing. So thank you so much for being here. But as usual, the first question is why? Why did you decide to shell off the nine to five corporate world and go into the craziness that is entrepreneurship?

Sure. I will give you the Cliff's notes. It's a long story. I, I had a thirteen year, stint in molecular diagnostics. And in my last job in that field, I was sort of given the I wasn't sort of. I was. I was given the opportunity to be an entrepreneur without any financial risk. So I got I was the first employee.

I built the lab. I hired the staff. I bought the equipment, managed the inventory, all of that. And it honestly planted a seed that I wasn't super aware of yet. But then about six months into it, I had to have neck surgery. I was in two bad car accidents as a kid. And, I was in a neck brace for four months, and I couldn't drive. First honestly, the first pause in my life.

I was 28. I, felt my you know, not that I was gonna die, but I just felt that, like like, my own mortality for the first time. Like, that was just something that happened to old people. And then all of a sudden, I was like, oh, shit. No. This is it. You get one chance at this, and I'm pretty miserable. I'm not jazzed at all about my career even though I had attained wildly more success than I ever thought possible.

And, honestly, that just kinda I sat in a sort of fear paralysis for a while of, like, what do I do now? I mean, I've worked so hard to get here. And, so, anyways, I I sort of found yoga to deal with chronic pain. They sort of undersell you the surgery of that. It's not the solution. You have to live with new hardware and figure that out, so that sucks. But,

anyway, so I I just, did that to sort of manage my pain and not have to

be one of those pain clinic patients. And then I, just started doing things that terrified me. Like, I just said yes to anything that intrigued me but terrified me. That was just outside of my comfort zone. And, eventually, I tried to quit, and I was going to pivot and take more of a role in, like, a sales sort of background, I thought I was still thinking narrow. I was like, okay. I'll stay in the same field, but I'll do something different, and and I won't be so bored and whatever. But my company gave me $40,000 to stay a raise, which was more than my, honestly, my first job out of college.

I was, like, in the early two thousands. I was like, oh god. So I went to my husband, like a coward, and I said, if I say I think the thing we should do with this money, it's you should go off on your own in landscaping. He had been doing it for almost twenty years, still loved it. And I just thought if he was gonna work that many hours, he should work for himself, and we could figure it out. So I did all of, like, you know, the things you don't think of about running a business, like website, socials, logo, things like bookkeeping, whatever. And

then fun activity.

Oh, yeah. The things that take up most of your time. Right?

Yeah.

But, anyways, he had a lot of success in the first year. Then next year, I was just sitting at a, I was at lunch with a friend, and I said, you know, I wanna host a retreat. I think that I had just taken yoga teacher training, and I had never been in a situation where I was there with so many strangers that were just, like, showing up just as who they were, not who they were trying to be, and everybody's accepting them. And I've I had been traveling a fair amount, and I thought I could combine that type of, like, a vibe with travel and host my own. So I did it. I did my first one in August of twenty eighteen, and then I side hustled the business for two years, and then I left.

I love it. Just you're like, okay. I've I've got this. My husband's taken care of. His business is kicking ass and taking names. Yeah. I've I've done some retreating every once in a while for the last two years. I'm ready to go full boy.

Yeah. I mean, I'm a numbers nerd, so I was just shoving money savings and watching all of that and, like, sort of trying to be calculated. But I quit October 2019, and then next year, twenty twenty, I had to cancel all of my events. So I'm like, awesome. Thank you so much.

Yeah. So Yeah. Twenty twenty was a very interesting year for a lot of entrepreneurs and nonentrepreneurs.

Yeah. I mean, if anything, I I was firm and that I didn't wanna go back. I got asked so many times to come back and help set up COVID testing in my previous and and I was like, no. I don't want to. I'm not I will figure this out. I'm not interested in in going backwards. This is a test, and I will not fail it.

It's one of those tests that the universe is like, are you really ready for

the big

change that we're bringing you? I love how your first attempt, the universe is like, we're gonna test you, and you're like, I I'm gonna stay. Yeah. It's a nice it's a it's a big test. It's a one that I can't may not be able to pass. But I love how you took it, and you're like, okay. We can use this for my husband. Like, if I can't go on, at least my husband can take it to the next level and can have that freedom that we're looking for. With doing your first retreat, a a big a big theme is entree in entrepreneurs, not knowing how hard it is when you first when you first jump into this world.

And I can only imagine, like, talking with just regular entrepreneurs about a regular business. You know? Like, oh, I have to help them, you know, do social media. You're you're planning to move people away from their comfort zone into a new area. Gonna have to

deal with strangers.

Strangers. That's kind of it. Dealing with the logistics of, you know, making sure everything's going great for the retreat, plus you don't know what's gonna go wrong, so you don't have those plans. What was it like what was going through your head when you're like, I'm gonna plan this retreat, and then you start planning it, and then you have to, like, pull the trigger and have the event? And, like, I can't imagine the amount of thoughts that were going through your head

to keep Yeah.

What was going through your head? Like, how much doubt did you have? Did you have doubt? Like

So much doubt. I had no idea what I was doing. And, I mean, most people don't the first time they try something. You just gotta keep beginners are beginners. Right? I mean, I probably learned the first the most in the first two I ever hosted. It's not that I don't learn something in every single one I host, but the the most the majority of the lessons came in the first two, mostly of what not to do. I, it's a lot of work. I now with planning other people's other entrepreneurs, like, the two biggest things I always tell people is it's a marathon, not a sprint.

So, like, you have to have downtime too. You can't most people don't sign up for a twelve hour shift. You know, people that work in the hospital do that three days a week, and then that's it. They don't do it for an entire week straight. And, so don't jam pack your itinerary. You have to rest as well, and you don't want your guests to be exhausted. But, also, like, hire help. Don't do it by yourself.

You it's terrible idea. It's like an overnight event. Nobody would host a wedding by themselves. You know? So and that's one day. So, yeah, that I I also like dealing with weather is tricky because we do so many things outside. So even now, even though I've done I think I've done 22 now, I still wake awake at night sometime like, oh god. What are we gonna do tomorrow if it rains? You know? So rain is rain, and we're all pretty flexible, but it doesn't mean that I don't, kinda want a plan b. So

I love that. Yeah. With with, planning retreats, and they often rely on, you know, the creative personal transformational experiences. You've scaled the wandering roots. How have you maintained intimacy and connection in larger, more frequent retreats? How do you keep those, like just, like, that intimate feeling of smaller ones?

Group size. It can be a longer offering, but I never bring more than I'm usually within the 10 to 12. I think the most I've ever had is 18, but that was a long weekend, and I had way more staff there. It was more of, like, an interactive, workshoppy, type of thing. So I 12.

Did you keep it? You just you just keep it. Keeping that FOMO going so people are fear of missing out too. That's what

I'm saying.

Yeah. But it's easier for you than my.

It's like herding cats sometimes, truly. Like, I always say the hardest part is just getting everybody in the damn car. But, it's just I don't know. It it is a lot of work, but it is very fulfilling too. People really connect. You watch strangers become best friends almost, like, right away. It's like everybody comes super nervous that, you know, they're not gonna make any friends or they're not gonna know anybody. And then by the first dinner, it's so loud and everybody's hanging out and all those, like, nerves and icebreakers and weird things are out of the way, and it's really fun.

It's like the first day of school again.

Yeah. It really is. It's that feeling. I kinda have it too. Like, I'm like, oh god. You know, sometimes we get a lot of repeats now, but we still get new people and someone was a little bit nervous.

I like that. Means you're still on the right path, and you still got a lot of Yeah. Same thing with me. When I've done over 600 interviews, and I still get nervous just before the interview because I'm like, what happens if the guest doesn't show

up? Yeah.

Like, my questions, they just give me one answer like, one word answers. There's no conversation. Like, I wanna make sure that everything goes great. With that, what has been kind of, like, one of the biggest lessons you've learned from some of the mistakes that you've done or that have happened or kind of like the like, I don't wanna say mistakes like you purposely did the error, but it was like it was a miss it was a mistake because no one thought that this would happen type thing. That's that's what I mean by mistake.

Good question. I mean, we always have travel delays. People lose their luggage. So I'm pretty much, getting used to handling, and we usually now always run somewhere that has a washer and dryer in case somebody does not add their stuff in two days. At least we can wash it. I in the beginning I don't like to do anything small. And in the beginning, I just was, like, went from to no audience at all. And I was like, I'm gonna host international on my second one, and I got two people to sign up.

So it's it's hard to build an audience from scratch. It's not it's not impossible. It just takes time. There's an added layer when, you're spending the night with your clients. You have to also convince them that it's valuable, but you're not a serial killer. So it's a little bit of a larger ass. Right?

I promise you won't die Yeah. On the Halloween weekend.

Life, and also I'm not weird. Yes. So, but so, anyways, I I think I was really surprised at how long it took to build an audience, and then, I'm sure you've encountered this, but they always tell you in any kind of sales course to have a small offer and kinda nurture them and, like, get earn their trust and stuff. And I never had a small offer. I started doing, like, a, long weekend locally, because that was where more most of my audience was coming in the beginning. And, beef but I was hosting five to seven days within the second, third year, so international too. So this is a big it's a big it's a big ask. And, also, so, yeah, I guess the thing that surprised me is just how much, probably I don't wanna say wise.

I don't have any regrets of the way I did it. But I do think that it would have been a better idea for anyone starting new, especially if this is a, brand new business to start a little bit smaller. Maybe do local shorter days for a few few years. Good idea.

Instead of going, we're gonna do a full international retreat. Yeah. To find out the gate.

Yeah.

Out of all the the events that you've heard, all these, not events you've heard, events that you've hosted, the retreats that you've done. Has there been one that kind of, like, sticks out as maybe having the most impactful lesson to you doing this, or one that just, like it just stands out because it was, like, the craziest things happened at all times. Like, it was just, like, everything that could go wrong went wrong, or everything that could go right went right, and it was just, like, superbly amazing.

Superbly amazing. I would say that always the failures stick out more than the successes of human. But so two. One, my second one, I hosted in Banff National Park in Canada, and, it we got hit by a massive blizzard fairly early. And so lots of people's flights got canceled, not rescheduled. My one of my chef and then another guest lost their luggage for forty eight hours. I got a speeding ticket on the way to pick up my photographer from the airport because I was so distracted. Just so much shit.

But and I had to almost do just change the entire itinerary. Some of the trails were too icy and, like, some of the roads were closed, like, whatever. And then when I hosted it in Sicily, it was 2021, fall '20 '20 '1. We covered too much ground. I wanted to show everybody everything, and, I shouldn't I've ever since then, I've hired drivers. It's just too much. I don't have any first of all, I I can't multitask when I'm driving. So I can't interact with the guests at all.

Like, they could be talking to me, but I'm not hearing anything. I'm just trying to figure out where the hell I'm going. And then, it's just it's a night. Especially if we have maybe an hour one way, it's a night it's a nice opportunity to be able to connect one on one with guests and see. Those moments are not fleeting, but they are sort of precious because there are 12 people in one meeting. I'd like to, like, take time to interact with everybody one on one. So, anyways, I now hire a driver so that I have the opportunity and I'm not, always just on a different capacity. Getting to the excursion and figuring that out is enough work than having day there as well.

So

Plus, you don't have to worry about getting speeding tickets anymore.

No. Exactly. God. I I think I was a race car driver in a past life. I just have such a hard time not speeding.

That heavy foot. That's terrible. It it's fine. It's our little secret. No one needs to know it. It's only going well or two about the

You're gonna edit this out. Yeah.

Okay. Of course. Of course. I love that. I love how each each iteration of your retreats, you learn something. You you improve upon it.

Mhmm.

And and it's like you're investing in yourself. And I'm curious, what do you do to invest in yourself to make sure that you're always showing up as the best version of yourself?

So a couple years ago, I decided I should be a guest on a retreat. If I'm preaching to everybody to, like, take care of themselves and invest in themselves, then maybe I shouldn't be such a hypocrite. So I did go on one last fall, and I went on one this year. This one was a shorter one. It was more for professional development sort of business y. But I still like to first of all, I never like the host to know that I'm a host. I just I don't it's like going to a a yoga class and, like, knowing that there's teachers in your class. Like, the more you do it, the more you're like, oh, those are the peep easiest people to teach.

There is no pressure, and there's no judgment because they've been in your shoes. But I think with new hosts or teachers, they're always like, oh god. She's she's watching me. And I'm like, no. I'm like the most graceful client you have here. I'm are gracious. I've, I've been in your shoes. So, anyways, but I also don't wanna talk shop.

I just wanna be a guest and, not there to steal ideas. I'm just there to sort of be in the other the other side of the coin. Right? Be in my guest shoes and remember that it is a little nerve wracking and, but also remember why I do it. So that would probably be the biggest way. I still invest, I think the most financial energy I've put into this business is always marketing. It's the thing I can't not it's not the thing I can't figure it out. It's the thing that I, feel the least confident in just coming from a very corporate world. Even though I worked for a lot of startups and I always wore a lot of hats, that definitely made me a troubleshooter and flexible and willing to learn things, but marketing is like this beast.

Sometimes what works won't repeat and work again. Like, like, from a data side of things, I'm like, well, that's stupid. You know? So

Yeah. You have a scientific background. So it's like Yeah. It's the the hypothesis, we proved it once. We need to prove it again. It's not working. What's going on? This doesn't make sense.

Yeah. No. It doesn't interest. It just doesn't work. It doesn't compute. Yeah.

The math isn't mathing. Yeah. Where do you see yourself in ten years from now? Because this this Mhmm.

You know,

doing it for quite some time now. You you've had the success. I'm pretty sure you're hitting the levels of success that you you you, you could, thought you would. But I'm wondering, where do you wanna go? Like, what's next for Anna and, the the the retreats?

Yeah. So I am definitely shifting a little more into helping other people plan and host theirs because it's a lot more flexible on time wise and being gone and all of those things. I'm I'm hoping to, like, reclaim travel for just vacation again for me instead of taking your hobby and your passion and making it your career. But, I I'm also the person that, like, feels that I will reinvent myself entirely almost every seven to ten years. I just I have a lot of interest, and, I don't wanna say I get bored easily, but I think the more you grow and change as a human, why wouldn't your career grow and evolve and change as well? That seems silly. So, I don't know. I just I'm I'm pretty tapped into my gut, and if it doesn't feel right, I'm not gonna do it. And if it doesn't, I'm just gonna give it a try and see where it leads me.

I think the more the older you get, the more you know that you're always being nudged somewhere that you had no clue was coming down the flights for you. So, I don't know. I'm just being open to it and trying not to control everything is sort of the space I'm living in now.

I like that. That's it's a very zen like mentality.

Demon.

Yeah. Yeah. For a speed demon, it's very zed. Very sloth like. It's very weird.

Yeah.

Yeah. Just remind me of that Zootopia scene Yeah. With the sloth driving the fast car. Yeah. Yeah. How do you build the trust? Because you're asking people, like you said, like

Oh, yeah.

You're you're you're asking people to fly to a remote location, maybe not fully remote location, but remote for them.

Pretty remote.

Trusting.

The beautiful places are never by the airports. No. It's We travel.

They're they're never closed and comfortable. You know? There's a long, uncomfortable journey usually. Yeah. You get to this comfort. But how do you convince them, like, to put their trust in not only you, but that the other people coming aren't also serial killers?

Yes.

Or they're not being led to, like, you know, the hostile films

Right. Right.

Who have their own films. Like, how did you build that trust, and how do you continue to build that trust?

So, when I first started, I and on the very first retreat, my girlfriend is a professional portrait photographer. And, she came. She was helping me make my sales page, and she's like, you know, I'm just gonna come. And I was like, I think that would be a great idea. I'm totally terrified. Like, it'd be nice to have you. And, initially, we pitched it as, if people really wanted to unwind, and disconnect from their phone and everything. If you still were going to some beautiful places, you want your picture taken, she'll take it for you.

And it also was a way for me to build some content that wasn't just stock photos in the beginning. And then it really turned into, we now do these flying dress things that we saw on the Internet and people really get into and whatever. And, women really connect over it and bond over it. But, I I just was like, I'm going to show up authentically. That's how it feels good to me. And when I would get on Instagram or do stories or we would share anything from a retreat, we just shared everything. We shared how sometimes I'm a super chef and everyone needs a hand in the kitchen or how we, handle food allergies. That's, like, a big one and a scary thing for people.

We just talked about everything. I would get on in the morning and be like, okay. Well, we have lightning. Usually, we will hike in the rain, but today, we have a major storm. So instead, we're gonna whatever. And I just tried to I wanted to be the approachable brand right from the beginning. I didn't want everybody to think that retreats are only, like, green juice and yoga 800 times a day. We really practice just I believe that wellness looks different for everybody, and it looks different for you day to day.

And so I just wanted people to come and choose their own adventure, choose in the moment what felt the best to them. If they didn't wanna do yoga the entire week, I don't care. That doesn't matter to me at all. If you'd rather take a nap than skip an excursion, awesome. We'll make sure we have some food for you if we're gonna if you're gonna miss a meal or something. I don't know. It just people come for the host. That was really hard for me to get in the beginning because I that seems a little bit scary and, like, a little too much, But they do.

They wanna come spend time with you, so I try to just just be who exactly I am on a retreat online. I also started blogging a lot, and I just shared very vulnerable things. And that connected me, I guess, on a deeper level to most strangers on the Internet, just getting out there and sharing things. So I wrote a lot about my, just recovery after having surgery. I wrote a lot about burning my life down and starting over. So get a lot of people that are sort of in transitional phases. I think that connected with most of the clients we get.

Yeah. I love how you were you used your vulnerability to build that trust saying, hey. I'm willing to be this uber vulnerable person online so the world can see. And you can trust me that I'm not gonna kill you if you come to my retreat.

I did joke about that a lot. I think this is, like, promise we're not serious. Because I also like, we're we all have a great sense of humor, me, Abby, and Elise, and, we're very laid back. So we would we would joke like that too.

Just I I get that feeling that you have a very zen, like, relax, say sensation when you work together just from this interview, and that it's probably a lot of fun on the retreats, and there's a lot of ton of fun. I'm guessing, like, it there's 90% laughing Yes. With the inside jokes that you guys have. I I I'm curious. Was there an moment at one of the retreats that you had that just kinda, like, stick out going, this is why I do this, or the particular moment changed something indefinitely in your life. Like, it was like, oh my god. This is a new way of doing something.

New way of doing something. I'll think on that. A lot of, the ladies will give me very heartfelt, like, thank yous and hugs at the end and thank me for doing it and telling me, like, how they've never been taken care of that much, like, ever in their life in that way or how they, you know, I never really felt seen in that cap in a different capacity in that way or, a lot of people have a really transformational experience, in front of the camera in a gown and things like that. That's always because, I mean, I'm usually pretty tired by the end of the week, and then I'm I'm like, okay. I'll do another one. Fine. But, doing things differently, I I send feedback forms, and I, almost immediately when they get home. And I I always tell them I'm more interested in the things that, we could improve on because I am not a guest as many times as we have guests, and I can't read anyone's mind, and everybody's different.

And I've learned a lot from those. I really, really appreciate construction constructive feedback. So people usually give it to you. Yeah.

Yeah. When you you generally ask, they're they're very kind in saying how they can help you get better. Was there one piece of feedback that really did change how you run your your, retreats?

I think in, Ireland, which was a couple years ago, a lot of people said they felt like they were in the car too much. And I was like, okay. That is the permission I need to to do half day excursions and only one full day or something like that. I really changed how I structured the activity after that. It was like a permission to be like, you don't have to give them everything. They wanna explore more of the area. They can come back by themselves. It's okay.

It's also not ever the primary reason that they're there. It's it's just, like, nice to be in a beautiful location, and we always stay at very beautiful homes. But, and it adds to the vibe for sure, but it's never the primary reason that somebody's there. So

I love that. We are coming to the end of the episode, which I hate because you are a fantastic and I'm pretty sure you can tell us about a dozen other crazy adventures that you've had on your, your excursions.

We need Jen for that, though.

Oh. Just

kidding. That's not kidding.

Then I'll get Jen on the next episode so we can get all those juicy, juicy details. But, with with that said, I have your 10 year old self right beside me. She's an amazing person. She's full of energy in life. And I'm wondering what advice you would love to be able to hand back to your 10 year old self.

I always still tell myself, keep going and believe in yourself. I really think the difference between the people that do and the people that don't are just the ones that keep showing up and keep trying. So just keep going. You're learning a lot of lessons. If it doesn't feel great, it will. It's the highest highs, the lowest lows. Just keep going.

I love it. Anna, I'm gonna off stage here. I want you to let my audience know where they can connect with you, how they can connect with you, and if they're interested in, checking out maybe a future retreat so the floor is yours.

My website is Yoru, y 0 u r, wandering roots Com. You can connect with me there. You can send me an email or book a consult. Some people like to chat in person to verify that I'm not a serial killer. And, we have only a couple spots left to Iceland. The Italian Dolomites sold out immediately, and we still have spots for Belize. Those are the only two chances to retreat with us, but they're they're both amazing, and we'd love to have you. And if you're an entrepreneur that wants to plan a retreat, you can also find all the info there.

And I'm on Instagram at your wandering roots. I'm terrible about being on it unless I'm on retreat, but just keep an eye.

I love that. Anna, I wanna thank you so much. I'm possibly gonna be looking into some of your retreats. I I like that Iceland and Belize idea.

Yeah. Thank you.

Sounds, sounds very relaxing and very beautiful. So, maybe maybe get to see the, northern lights as well,

in

the horizon, which would be amazing. But I wanna thank you so much for spending some time with us today and all the all the the stories you shared with us. It was a pleasure having you.

Thank you for having me. It was lovely chatting with you.

To my audience, make sure you check out the show notes down below to connect with Anna and, see maybe if I will see each other on a retreat one day. Remember that you have the control to make your life as amazing as you want, so remember to always, always invest in yourself. Thank you.