All Things Retreat Podcast

7 Secrets to Successful Women’s Retreats

Holly Porter

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0:00 | 26:55

Summary
In this engaging interview, Caterina Rando shares her journey into hosting retreats, her strategies for success, and her passion for empowering women entrepreneurs. Discover practical tips on starting retreats, building community, and creating impactful experiences that transform lives.




Takeaways
Starting retreats close to home for ease and familiarity 
Building community and connection among women 
International retreat challenges and solutions
Start close to home for your first retreat 
Build community through unique activities 
Use spontaneity and flexibility to enhance experience
Plan your first retreat close to home 
Partner with local experts for international retreats 
Create signature activities that reflect your brand




Chapters
00:00 Introduction to Caterina Rando 
03:23 The Journey into Retreats 
05:53 Empowering Women Entrepreneurs 
08:51 The Importance of Community 
11:39 Transformational Experiences in Retreats 
14:33 Creating Unique Retreat Experiences 
17:02 The Power of Connection and Collaboration 
19:54 Final Thoughts and Future Plans 
25:47 RNR Outro Final.mp4 
26:26 RR.Gift.RetreatRnR.com.mp4



🔗 Connect with Caterina Rando
📧 Email: cat@caterinarando.com
🌐 Website: https://caterinarando.com/
📸 Instagram: @caterina_rando
📘 Facebook: CaterinaRandoTWIBC
🔗 LinkedIn: Caterina Rando


🔗 Connect with Holly Porter | Retreat RNR 
📧 Email: holly@hollyporter.com 
🔗 LinkedIn: Holly Porter | Retreat RNR 
🎵 TikTok: @retreatrnr 
▶️ YouTube: @intlretreatassociation
📸 Instagram: @retreatrnr | @hollyporterinternational 
📘 Facebook: HollyAnnPorter

SPEAKER_01

Welcome to All Things Retreat Podcast. I'm Holly Porter, your host and CEO of Retreat R. With over 25 years of experience in designing transformative retreats. I'm here to share insights and inspiration to help you create extraordinary experiences. Whether you're a pro or just starting out, you'll find valuable ideas here. Enjoy the ride. Let's dive in. Hello and welcome to the show, everybody. We're excited to be interviewing Katarina Rando. She's a best-selling author, podcaster, retreat leader, and woman's business mentor, extraordinaire, who passionately serves women on a mission. She shows women, she shows women sales authentically and more effectively, speak publicly, to build instant influence and scale strategically, all while blissing in business. Katerina is the creator of Sales Bliss Accelerator Program and the Speaker Mastermind Program and the AMP Up Mastermind Adventure and Cruise. Her books include Learn to Think Differently, released in several languages, A Women's Guide to Starting and Giving Circle, and her latest book, The ABCs of Public Speaking. Katerina is also the founder of Thriving Women in Business Center in San Francisco, California. And Thriving Women in Business Giving, an initiative that has raised over $50,000 for women and girls education and entrepreneurship training. Welcome to the show, my friend.

SPEAKER_00

Thanks, Molly.

SPEAKER_01

So I I have a little inside scoop. Katarina and I have been friends for a few years. Did we meet women?

SPEAKER_00

Oh, yeah, we go way back, my friend.

SPEAKER_01

Yeah, years and years. And we've been to events together and we spoke together. We're just anyway, she is a dear person. And I will just brag for a minute because she loves being first. So I knew when we launched International Retreat Association, I was she was one of the first ones I called about it. And she was ready to sign up as a founder. And I didn't even have a payment acceptance plan ready to go. So I um called her when we did launch it and said, Hey, I want you to be my first member. And of course, she did it within minutes, and she's our first founder.

SPEAKER_00

Yay! I'm blissing.

SPEAKER_01

And I think it pays me first because now we're spotlighting her and bragging her up, and we only have a hundred of those. And when they're gone, they're gone. So when we opened up the association, we opened up Essential Membership, which is only $111 a year, and then the founders' memberships, which are $444 one time only. So we're so excited to have her part of that. But she has so much genius in the retreat. Um, I think you told me you had six retreats this year or having seven. Seven. Okay, so there you go. We're gonna be hearing from a real live and true expert that does lots of retreats. That's a lot in a year. Is this the most you've ever done in a year?

SPEAKER_00

Uh, probably so. Yeah. We're we're doing three cruises, three retreats on cruises. I'm doing and I'm doing four retreats at my center. And three of them are on public speaking and one of them's on scaling. And yes, it's a lot. Next year I'm not doing any cruise retreats. Okay, but I'm doing a retreat in Italy next year.

SPEAKER_01

Oh, I love it. Yeah, I'm headed there the end of this year. I'm going to Croatia to an event, and then I'm, yeah, trying to talk my husband into our 25th anniversary so we can hit Italy too. So there you go. I know, and so I never been there, so I'm excited. Um, so what got you started in retreats?

SPEAKER_00

Here's the truth, Holly. I was at a national conference, okay, okay, and this gal was doing a breakout session on her retreats, like how to do retreats for women. And the truth is I thought it was pretty schlumpadinka. I thought, you know, I could do way better than this. Yeah. And that motivated me to get my party started. I live in San Francisco. My first retreats were in Napa Valley. And I do think that it's good to stay close to home the first time. And the reason is because a lot of your people, they're not gonna have to fly in. Yeah. Also, it's smaller the first time, you're not gonna stress as much about the money because you don't have to drive or fly to Timbuktu.

SPEAKER_01

Right.

SPEAKER_00

And the so my first three retreats were in the wine country, and of course, everybody loves to go there. Yeah, that made it easy for me to fill it.

SPEAKER_01

Yeah.

SPEAKER_00

And you know, you can take and I train women on how to do retreats, but let's be clear. You can learn all this stuff. It's when you're actually doing your first retreat that you learn the most.

SPEAKER_01

Yeah.

SPEAKER_00

And it's real learning. And the thing is that so many women uh you know, there's two sides. One is they plan it too close in, and that has them have stress with their first retreat.

SPEAKER_01

Yes.

SPEAKER_00

Or they take so much time planning that they never quite launch.

SPEAKER_01

Yeah.

unknown

Yeah.

SPEAKER_00

You know, and so I just feel like pick a date, pick a time, pick a place, yeah, pick a theme, and go. And the rest you'll figure out after the first gal writes her check and signs up.

SPEAKER_01

I agree. And and you know, it's funny because when I was starting the uh International Retreat Association, I had an attorney, not my attorney, by the way, but it's their job to poke holes through everything, which I love when people do because I don't have all the answers. I'm always willing and open to listen. My mom used to say, I'll listen to everything you have to say, but don't be offended if I don't do it. Like I thought that was brilliant, you know? And she said it a lot nicer than I do. But it was just like, yeah, take take those and and talk about them. But this attorney said to me, You're gonna just launch this whole thing, like with not having everything figured out. And I was like, I mean, that was a dumb question for me. Because I was like, yeah, because you know what? I well, he was talking about like the membership and things. And I said, I was so inspired to have this answer. I said, Well, how often do you get emails? I get them almost daily of PayPal, eBay, Apple updating their terms and conditions. Why can't we do that? Like if we change something, we send something out, we've updated our our policies and procedures, whatever. And all right, so anyway, I think you're right, 100%. I love that. I love also that you said you stayed close to home for the first three. I I think that's a magical number for me for many things. Um and uh yeah, I just love that because you you kind of got to figure it out in your own backyard before a lot of people when they tell me I just went to an event and more than half of the people that were there hadn't even done a retreat. Good for them for showing and paying a high ticket price to show up at an event to learn about retreats because I like being the dumbest one in the room. I'm you know, that's how we learn. So good for them. But I thought, oh my gosh, when they were telling me they were planning these international retreats for their first one, and I just was like, oh honey. I mean, I was scared for them, but you know, it's okay. It's it's their journey.

SPEAKER_00

But there's so much to deal with internationally.

SPEAKER_01

Yeah.

SPEAKER_00

I mean, I told you I'm doing my first retreat. I've done 30 retreats. I waited until number 31 before international because like I want to put my attention on making sure everyone feels VIP. Yeah. Attention on great swag, great activities, great excursion, great connecting everyone.

SPEAKER_01

Yeah.

SPEAKER_00

And if I'm also having to deal with all the international challenges, and there are international challenges, and I haven't figured out all that other stuff, yeah, then it's not gonna be an amazing street because you have to put your attention there. And I've had I believe me, my the horror, you know, like you, Holly, I hear all the retreat horror stories and more about international. Because the other thing is, some gals are hosting retreats in places they've never been. They've never been to the venue, they've never been to the country. Yeah. And they well, you know, it'll be all right. Let me tell you, I lived, I'm I'm going to Italy. I lived in Italy for the year a year, but also the exact retreat that I'm doing, I did it two years ago with somebody else, and she's my on the ground partner, and we're making I love that. But that's the way to do it, not just like, oh yeah, let's let's go to an exotic location with everything figured out.

SPEAKER_01

There's um, I don't know how we're gonna do it yet. Like I said, I just need to find the people that know how. That's my lesson here. Um, is in the association to do some international things where we have a list and these are the things you need to be aware of. These are the things, these are the four states in the United States that you need to go through a travel agency to do it legally. Like those are, I feel like the responsibilities of an association to be able to pass along to our members, but what invaluable information to have to know all that stuff and not have to figure it all out on your own. So it'll be a definite growing list, but um, yeah, that is like one on on definitely my my list of things to do for sure is to start that. And so yeah, we'll love it when people can contribute to that list for us because you've been there, you've done that, you know, and hey, watch out for this. And oh, this is a good contact. Love it, love it, love it. And I love that you partner with someone there.

SPEAKER_00

Absolutely. Partner with someone on the ground. You definitely want to do that when you're doing international. Totally does have her own retreats, so she knows the business. You know, I want to say people think of sometimes people think of retreats as exotic locations, yeah, or international. And you can do a retreat, you know, in your living room to get started. You can do a retreat in your city, you can do a retreat at a retreat center hour from your house. It doesn't, it can look a hundred different ways. And I like to say phase one, phase two, phase three. Yeah, you know, start with the easy one, start with whatever's not gonna make you stressed financially, and then build from there. You don't have to start with your you know, Orient Express train retreat the first time.

SPEAKER_01

Yep. No, I I so agree with you. We're that's why we're friends, we're so in alignment. I love it. And I yeah, I say I call them a day treat or a night treat. Start with a day only and then do an overnighter, which is day treat, night treat, right? Um, so I know that you specifically work with women and your brands around helping women thrive in business. So, what first inspired you to dedicate your life to serving women entrepreneurs?

SPEAKER_00

I used to serve men too, Holly. But the truth is I'm born on March 8th, which is International Women's Day. Oh, yes, it is. I I worked on the ERA countdown campaign when I was in high school with my Oh, I used to do that too. That's funny. And um, I went to Catholic school where you do, you know, you get uh I mean it's challenging Catholic school, but also it's a bit of a feminist education, even though they would never admit to that or say that. Because these are all independent women that are teaching you. So I learned a lot from the nuns. And when I got into business, I felt that it's my calling to help them. And you know, about you know, women and money and asking for money, and we don't want to be salesy and we all start businesses not because we're thinking, oh, I'm gonna make so much money. We start a business because we want to be of service. Yes. You were telling me earlier about when you did style and color and all that. You know, I don't know if you know this, Holly, but I'm super style enthusiast, and I don't think that will be my profession. Yeah. Why do women start that business? Because they want to help other gals look good and feel good. That's why, and and that's the thing. It's more of a mission and a calling than excluding guys. It's simply that I love to serve the ladies. And the other thing that you know is that women thrive in community, and sometimes that community is just women where we feel like we can totally be ourselves and and also sometimes you know, guys have to take up a more space in the room, and their voices, their voices are much more dominant in the room. And I've also found it's challenging for them to let a woman not all for all guys, and you know, I'm sure they've gotten more enlightened over the years, right? But you know, when you're a woman leader, sometimes it's challenging.

SPEAKER_01

Yeah, that's right.

SPEAKER_00

Um, and we just have a great oh, and you know, the other thing is we do a lot of girly stuff. We do you do jewelry exchange at every retreat I do. And by the way, it's good to have some signature things that you do that are unique to you and your retreat or mostly your retreat. We do an accelerated jewelry exchange, we do afternoon tea with fascinators, we have a gem and sticker party. I mean, we do this at all my retreats, so love it. It's very girly.

SPEAKER_01

Wow. We when when you were saying about how you did the philanthropy work, you know, and raised them, you're gonna love it because we rebranded my nonprofit just recently. We're still like putting the final little uh touches on it, but it's RBL Women, which is Rebel Women. I love it. Rise, build, lead, and it's all about women that have gone through adversity, which is every woman, if you think about it, and teaches them how to find their purpose and build and lead in a stronger way. So you and I are gonna have to chat about that'll be a whole nother thing that I'm sure we'll be on board with doing together. That's gonna be a great collaboration.

SPEAKER_00

I'm sure you have a Rebel Woman retreat in your future, my friend.

SPEAKER_01

We do. Yeah, yeah. We I have a great board um that you know saw me through my whole COVID almost dining journey. And that's why we that came out of the nonprofit came out of that. And but it was time to um rebrand and and uh move into this space. And I love it because it goes so well with the retreat association as well. Um, but that being said, of course, that's for women. I also want to put a little plug for the listeners listening that in the association, I am so supportive of men's retreats, but separately, right? And so, like you've got this space where that's where you've chosen to spend your time. There's there's a guy I'm trying to get on my leadership council that does specializes and does events for men. And I love it because like my husband's their avatar perfectly. And I love that they're doing that. And so I really want people to hear this that you're thinking you're a woman, you're listening to this, maybe, and you're thinking, well, what about the men? Trust me, I am so on board with that. So there's stuff coming to the association for men too. So we need it. I I call it balance.

SPEAKER_00

Yeah, well, I think retreats are, you know, I've been saying to my client base and and in my posts, I've been saying two retreats a year, you got to make it an SOP standard operating procedure.

SPEAKER_01

Oh, I agree.

SPEAKER_00

Yes, and it's not about decadence or spoiling, it's about time for a reset, a revitalization, a refresh, a reflect, a renew. And in our so full lives, it's a really good strategy to have two retreats a year.

SPEAKER_01

Oh, I love that idea. It I love that you said standing operating procedures. You know, for a business person, listen up, people. Uh that is like gold nuggets there. She's dropping. So I I think, yes, it just you gotta have some RR. And it's okay to do things like that without your partner, spouse, whatever they are to you. Um, you you gotta do some things on your own.

SPEAKER_00

Yeah. I have women tell me I have it's amazing when I have women that have come to a retreat that have never traveled without their husband, and they are flourishing because it's a different type of experience. Yeah. And you know, you have time to be with gals and blah blah blah. You know, I the the way I started my uh I do this amp up adventure, which is a mastermind cruise for women. We have like 30 to 50 women.

SPEAKER_01

One day I'm gonna come.

SPEAKER_00

2028, okay? I'll put you on the list right now. I'm getting it ready now. Anyway, I'm I did this retreat and there was about 10 gals there. And I said to them, okay, let's go to my suite. I always get a suite when I'm on a retreat, and we're gonna mastermind for 90 minutes, and then we're gonna go to dinner, okay? That's what I said to the gals. So they come to my cabin for afternoon masterminding. We're still there masterminding seven hours later. And that's when I said, Okay, obviously they want to be together and share ideas and tell stories and ask each other's opinions and share resources. And here's the thing at the end of the retreat, when I said, Okay, my friends, what did you like the best? My excursion, I think we went to like a dolphin excursion. Okay, we would did a silent disco. Of course, I told you my signature stuff. Do you know what they said? Masterminding masterminding.

SPEAKER_01

Totally.

SPEAKER_00

That's what they like the most. Yeah. So that's where my whole idea to do the mastermind retreat came.

SPEAKER_01

Oh, totally. Yeah.

SPEAKER_00

And it it solidified the awareness that women want to connect and visit. And in our business lives, especially if we're working from home, we're not doing enough of that. And and also when you know, we go networking events and all that, you know, we both love that. But then, okay, that's two hours. And you know, you got a speaker and you got announcements, so there's not even a lot of connection time. And when you're on a ship and you're stuck with these gals for a week, like you make such friendships and yeah, collaborations and clients, and they have so much fun. And I want everybody to recognize that yes, you can do great programming for your retreat. You know, we do movement in the morning. We, you know, we have all kinds of things that we want to do to make it a great retreat. But the truth is, if I just open the door and put them in the room and welcome them and say thank you when they leave, they would tell me what an amazing retreat it was because they just want to be together.

SPEAKER_01

But it's good to recognize that and not be so structured or rigid in your thinking of it all, but you can't be flexible. Um, a lot of retreat leaders think I have to stick to the schedule. And I think the best retreats are when you don't know you have an outline, don't do a play by play, minute by minute. I don't think people necessarily need that. I think they need a structure or an open space of this is what we're gonna do. If something changes, just ask for permission. Are you are you okay if we decide not to do that? Or are you okay rarely? They're gonna disagree with you.

SPEAKER_00

Well, Holly, let me give you my super tip, okay? Yeah. So I do not give, I give them a schedule. Okay. Group session, group session, blah, blah, blah. I give them a schedule. I do not give my retreat participants an agenda of everything we're gonna be doing. Yeah. And the reason is so we could do this, so you can dance in the moment. Yeah. On our last uh cruise retreat we did, I met the comedian that was gonna be on the ship a couple days before. He just happened to be know a friend of mine at the hotel before we went. And I said to him, Will you do a special session with my gals on using humor in their speeches? And we do like a talent show, so you know, how to be funny. Oh my god, the ladies loved it so much. Now, and by the way, when you can give people something on a retreat that they couldn't do on their own, like this special session with professional comedian, they love it. You know, when we went to Napa Valley, I hired a company that does grape stomping for corporate groups, and that's something most tourists can't do on their own, you know. And so whenever you can find something that is special just for your retreat, yeah, it is absolutely a hit. But sometimes those things are happening organically. You didn't know before you got there. So that's why don't give them the every second what we're gonna be doing. Just say, show up at this time, we'll be done at this time. Okay.

SPEAKER_01

And it's okay. Let go, let go of that. If yeah, I'd love that. And I think the attendees appreciate that and respect that. At least I would hope they do. I think they do.

SPEAKER_00

I think, well, they they, you know, I say, hey, this is how we do it on my retreats, okay? Yeah, don't apologize for it being different because uh I always get the question, well, what time if I want to book some spa services? So I say, do it very early in the morning because we don't start till 9:30 or 10 or late in the evening. That's what I tell them.

SPEAKER_01

I love it. Yes. Oh, well, and it looked, I saw all your photos coming up on Facebook. I'm like, oh, they're having so much fun. I'm so happy for them. And I just think it's retreats are such a world changer. It's it's like in a short time. There's two things, two, two things that I've done that I feel like I get that joy from doing for others. Retreats are definitely one, but in a little longer sense. But my best job I ever had was delivering flowers because you saw the joy in their face. Even if they got flowers from someone they didn't want them from, you didn't know that till you walked away and they read who they were from, right? I only saw the joy, I only saw the good. That was the best job when I was like 17 years old. So it was so great to feel that. And the other thing was I had a salon spa for 20 years. When someone can sit in my chair for two hours and walk out transformed and feel like a totally different person, man or woman. To me, it's like that gave me joy because I saw that that light in their face. And I think retreats do that just in a little bit longer of a sense.

SPEAKER_00

They do that. I'm thinking of a gal right now, Holly. She's come on two retreats with me this year. She came to my speaker retreat first. Not only did she transform her speaking, but she found her voice to use in her marriage. You know, she's a younger woman, and now she's asking for what she wants, and she's happier. Her partnership is much better. And that's transformation. You know, it's it's and then of course she came on the other retreat, and she's uh she did uh dancing at the talent show. I mean, she's a very introverted person, like she totally has come out of her, and she's gonna be quite a business leader, and the retreats have really catapulted. That that coming out, that empowerment. And that's the other thing we haven't said yet on this call that we're doing. You know, we're in the empowerment business. And I love the empowerment business. Because you get to see that transformation. And it's quite wonderful.

SPEAKER_01

And I have to add another word to that that I feel like is happening because of the empowerment impact.

SPEAKER_00

Yes.

SPEAKER_01

There's impact coming from being empowered.

SPEAKER_00

Yeah. And you know, with that, and the other thing, Holly, is that you have the ripples. I mean, I I'm thinking of a gal now. She's doing she's doing like six retreats of her own this year. And she came to the program on how to do retreats, and she turned around and is building her femre with it. I've got, oh my god, I got I told you I'm doing my retreat in Italy with my Paula's her name. She is my client and also did this retreat. I got three other clients doing retreats in Italy with Paola because of the the the ripple of it. And that's what we well, that's what happens.

SPEAKER_01

Well, I might need to meet her when I go there this year.

SPEAKER_00

Absolutely, my friend. I'm I'm I'll make an introduction.

SPEAKER_01

Let's do it.

SPEAKER_00

Exactly. Empowered women empower women.

SPEAKER_01

Yes.

SPEAKER_00

And that's the other thing women are great at. We're great at connecting. We're great at putting Mary with Jane and Jane with Cela. Yeah.

SPEAKER_01

Oh. Okay. We're coming at the end. Dang it. I'm like, we could talk forever. But I'll tell you what, let's have you back on another show.

SPEAKER_00

My friend, you know, I'm an insta. Yes for you.

SPEAKER_01

I didn't have I I only got through like three of my questions and I had like 20. I knew I wouldn't get through them all, but I wanted anyway, because I knew we'd do more conversation. Um, okay, I'm gonna do a couple rapid fire before we wrap up. Morning routine must have. Oh my gosh. Movement. Introvert or extrovert.

SPEAKER_00

Ambivert in the middle.

SPEAKER_01

Love it. If you could host a retreat anywhere in the world, where would it be?

SPEAKER_00

Well, I told you I'm doing my first Italy one. I think you know, there's the retreats you host and the retreats you go on. And I go on at least well, last year I did four that I was the participant. So I'm I really want to go uh do something on the Orient Express. Oh that I don't want to be in charge.

SPEAKER_01

I just want to be Oh, when you find that, let me know. That that I that's on my bucket wish. Okay. I love it. Okay. Well, we're gonna put all your information, how they can get a hold of you. Um, does your website have a list of your retreats that you're doing as well?

SPEAKER_00

I do have a list of my retreats and also I do a free workshop every month. And when you're doing retreats, you have to learn how to sell. You have to learn about speaking so people get to meet you. And I'm all about using it to grow your business. So yeah, please connect with me. I I love meeting retreat gals and also come join me for a free workshop. Oh, and I've got a podcast too, Holly, which I'll have to have you on. It's called Expand Your Fempire.

SPEAKER_01

I love it.

SPEAKER_00

About building your business and it's very inspirational. You always will leave more uplifted than when you showed up for an episode.

SPEAKER_01

Well, I know our listeners can expect that after hearing hearing you speak today. So thanks for coming on. We'll do it again. Yes, we'll do it again. And um go check Katarina's website out, and I can tell you, I have been on one of her retreats yet, and I can tell you just from watching everything and knowing her personally for many years, it's gonna be amazing. It's just one day our dates are gonna match up and it's gonna happen.

SPEAKER_00

I'm gonna give you my 2028 dates very soon, and you're not gonna be able to tell me your book.

SPEAKER_01

That's true. That is so true. I'll plan around it. So I love that. Um, anyway, okay. Well, thanks again for joining us. Um, everybody, come join us next time and go check out Katarina's website. Bye for now. Thanks for joining us on this episode of All Things Retreat. We hope you're leaving with new ideas, fresh inspiration, and the motivation to take your retreats to the next level. Don't forget to subscribe and leave us a review. It helps us grow and reach more retreat leaders like you. And if you have any questions, topics you'd like us to cover, or just want to say hello, send us an email at infoweetreatrnr.com. Follow us on social media to stay connected and catch all the latest updates. Until next time. Remember, great retreats start with great intentions. Let's make them extraordinary one step at a time. Thinking about hosting a retreat? Before you dive in, let's make sure you're really ready. Grab your free Are You Retreat ready checklist and find out if you've got everything in place from your purpose to pricing to your audience and agenda. Don't guess, get clear. This quick checklist will show you exactly where you stand and what you need to make your retreat a success. Click the link below in the show notes to grab your gift and take the first step toward hosting this conference.