Episode 115: How to Double Your Business

Will joins the podcast to share his journey to becoming a wedding destination expert and how he is doubling his business year over year with a very lean team.


Time to remove the mystery out of growing your business. Will joins the podcast to share his journey to becoming a wedding destination expert and how he is doubling his business year over year with a very lean team.
Will Medina is the founder of the Destination Wedding Playbook & Destination Weddings Expert, LLC, a boutique travel agency that focuses primarily on destination weddings to Mexico and the Caribbean.  Based in South Florida, Will serves his clients around the world while mentoring dozens of agents around the US in growing their romance travel businesses.


Chris: (01:34) Yes, it is good to hear and Will it’s always good to connect with you. I know when we were in Miami, yes, we were in Miami at the Study Hall just hearing about… Well, first off your excitement around the application was just amazing and two it’s just hearing the nature of your business and how you’ve leveraged the online space to grow it and then give back with something that I was like, oh, we have to get this back to the podcast community. They have to hear this. Let’s start from scratch Will. Tell our listeners a little bit about your background and your business.
Will: 02:13 Well, thank you Chris. I love the application and my excitement is really because this is one of the most cliche things that I’ve heard and I keep repeating but I truly love what I do. Unfortunately, I was coming to an industry that it’s not shaped for a millennial, for all of the techie things that can live out there. In the travel industry I started back in 2009 and I started this side hustle, so to speak, as an online travel agency.
Will: 02:54 It’s really funny because they call it online travel agency and then once you dive into it the first thing that you start hearing is get out and network, go join the Chamber of Commerce, go do bridal shows. And I’m like, okay, wait a minute. But I was really young and just starting out and I’m like okay. I didn’t even know that the possibility of really making a living and just making this a full time job was there.
Will: 03:22 It was kind of like a side hustle while I was doing two other jobs. Anyways, this was back in 2009. I did all of the things that people used to tell me to do in the industry, in the conferences that you went to, training over training. Again, it was to be this online travel agent or travel agency but then the message didn’t carry over. It was all about these manual things. There was not a good CRM in the space, there was not a cohesive system that you could actually do all of that stuff.
Will: 03:59 Then you add to these the fact that people, gurus were, oh, you need an email list and you need a newsletter. All of a sudden your mind is like, oh my God, I went to school for marketing but they didn’t teach me any of this stuff. We did case studies for Harley Davidson in Milwaukee, Wisconsin. All of a sudden it’s like, oh my God, I just want to be a travel agent because I like to travel, but now I have to learn this online space.
Will: 04:27 Fast forward, I spent the first, I would say four or five years, doing that and really to be honest struggling because it was not moving at the speed that I wanted it to be. It was definitely not giving me the income that I needed and relying on referrals in my young brain was not a really good strategy even though that’s how I built my business and how I got it to make money. From there, I want to say about four years ago or so, I was really on this journey of, listen, I was about to quit my full time job at a bank, really top 500 company.
Will: 05:10 I was one of the top 1% in the company 4Xing all of my sales goals and really, really grounded in a really nice job here in South Florida. I loved it. I truly loved my clients. I had a great team and whatnot, but even my corner office in a block away from the beach here was still too stiff for my gypsy heart. I wanted more flexibility, I want it to be able to really travel and really have a little bit more control of my life.
Will: 05:48 From there, about four or five years ago, when I was starting really to get serious and mapping out my exit strategy, I was thinking, alright, there got to be a way where I can take what I’m doing, which is working okay, and take it all online where I can actually meet with these couples for the consultations and whatnot and do it in a way that it doesn’t matter where I’m at.
Will: 06:14 Because I had moved from Milwaukee Wisconsin to Fort Lauderdale here in Florida and I had to start from scratch. I was moving a business that was built on referrals to a completely different state while I was doing my full time job and all of a sudden I was like, oh man. Thankfully, obviously Facebook is a really great platform. I kept my connections and whatnot, but I didn’t have the day to day interactions with people that I knew and people that would spread my message.
Will: 06:44 From there I just went into this journey of the University of YouTube and started researching all of these things of how do I do this and piecing it together. I spent I want to say three months. Literally, I still have a picture here in my office of my first “Funnel” that I wrote. Just mapping this out. I’m like this got to make sense somehow. I was listening to a podcast at the time, that was my first few podcast I was listening to and I heard about this thing about a marketing automation expert.
Will: 07:21 I’m like, what are you talking about? I like this. I was burnt out from YouTubing being and researching and really trying to do it on my own. I contacted this lady that was the guest speaker on the podcast and we had a consultation. I basically told her my idea, my strategy. She’s like, oh my God, I’ve never worked with a travel agent, but you have such a clear vision of what you want to accomplish that I think I can help you.
Will: 07:50 I’m like I just need help with the tech. I was being all cocky and stuff, I just need help with the tech. Well, it didn’t hurt to have a little bit of someone else overseeing my idea and I hired her. It was four meetings and one of the tools that she recommended was ActiveCampaign. We built out this funnel that I had on paper already. I wrote all my copy. At the time I didn’t even know what copy was, I wrote the emails.
Will: 08:23 But going to have my ideal client and I had the foundations of the business offline, but online it was a whole different animal and that’s just the business that I wanted. I did not want to do bridal shows every single weekend. I did not want to be part of a Chamber of Commerce. No offense to those of you out there that belong to the Chamber of Commerce. I’ve done it. I’ve done BNI. It was just a little bit too slow for my taste.
Will: 08:47 Again, I needed something that is very unique. I’m very nichey so I needed brides that wanted to do a destination wedding in Mexico or the Caribbean. My pool of clients needed to be more than just the 20 people in my group. And then from there that’s where I started with ActiveCampaign. I started with just that one funnel and I was like, oh my God, this is magic. I started just working on personalization and the tags and do this and breaking down the automations into smaller pieces as I learned more through your podcast, through the videos on the website of ActiveCampaign.
Will: 09:37 Four plus years later I literally have probably 6X my client base, the number of weddings that I booked. I’m going on 10 years in business and all by myself without employees, without a big team, without a retail office, without a networking group. With automation and with that particular follow up funnel I’ve been able to enhance and close so many more sales in consultations. Last year alone I did 23 wedding groups.
Will: 10:15 This year I’m already at probably 70% of my goal and it’s only quarter one. It just really changed the way I do business. And then if I look at the backend of that, that’s for the marketing portion of that which is really great and obviously what helps me convert. But in addition to that, then for those of you that don’t know how this works, I do destination weddings for couples. I don’t do the wedding planning itself.
Will: 10:49 I am a travel agency that specializes in the group aspect of that. What that means is that with every bride or every bride groom or wedding couple that I book, I am also acquiring between 50 and 100 new clients that are booking into that wedding to go to Mexico, to go to the Dominican Republic, to go to Jamaica for three to seven days. That means that that growth it’s something that you need really good systems to handle.
Will: 11:17 Because now those are 100 people that you have to service, after you invoice them you have to give them travel tips and you have to prepare them because you don’t want to be the agent that takes the money and disappear for the next nine months until this wedding happens. I could not do any of that without ActiveCampaign and I proudly, proudly say that ActiveCampaign was and continues to be my first employee ever.
Chris: 11:45 That’s so powerful. I mean, there’s so many elements of your story that are highlight worthy. A few that stand out is the fact that you just didn’t settle for the status quo. In a service based business where you built it based on referrals, it would have been so easy just to ride that wave. There are times in business where you should, but I think that millennial portion of you really kicked in to say, okay, do I really want to do this? And if I do want to do this, do I really want to do it this way?
Chris: 12:26 Thankfully enough for that forward thinking you were able to prepare for an event that you hadn’t even planned for. You didn’t know that you were going to move. That wasn’t in your mind when you were first building your business. But given the fact that you were aware of the possibilities of connecting beyond your geographical location, it enabled you to make that transition and not lose business and still operate. In fact, you can argue that that transition was really the birth of the next phase of your business from then on and how you would run it continuously.
Will: 13:13 300%. I’ve probably doubled my business every single year since I moved which is not easy to say when you are starting over again. I moved here for following a dream and transfer a job that I had just taken within a year. I moved here by myself. My then fiancee at the time took him nine months to find a job. It was really, really a tough year one here in Florida. You and I talked about that when you were in Miami. But yes, it’s just been double growth every single year ever since. Again, that’s hard to do. The first year you feel like, oh my God, is this a fluke? Did I just get lucky?
Will: 13:59 But then all of a sudden it’s like, oh my God, guess what? Chris, in the travel industry or actually the wedding industry, we have engagement season which is basically the holidays when people get engaged. Most of the people that get engaged between Thanksgiving and Valentine’s Day. That was my goal at the beginning. I just need to be ready for engagement season. I just got to be ready for that so I can get you in a couple of weddings booked. Now, engagement season for me it’s every freaking month.
Chris: 14:35 I can see that because your pool is growing. The amount of people that you can reach and you engage with is growing due to technology. Now that person who is getting engaged in a random month of April can connect with you way easier than before if technology didn’t allow you to create that community.
Will: 15:00 Absolutely.
Chris: 15:01 Oh man, I love it Will. This is really the reason why you’re on the podcast is because this is the challenge that every business owner faces. You’re looking at your business and it really does not matter if it’s traditional or primarily digital. You have to look at what you’re doing, how you want to operate and figure out what does it look like for you? What tools best serve you? What processes can the tools handle and which ones are you going to take on yourself?
Chris: 15:35 How many people are you going to hire? You mentioned ActiveCampaign was your first hire. That first hire, getting the most out of the platform really sets the table and allows you that freedom to decide, okay, I like this. I’m going to keep doing this. This is working. Or there’s no harm, no foul if you say, okay, I like this. I want to bring on some other people to help me run this so I could focus on something else.
Chris: 16:01 The point is you understand the evolution of technology and instead of running from it and trying to prevent it from happening because it’s inevitable, it’s going to hit every single market, you embraced it and allowed it to help you redefine what your business would look like. I just loved that piece about your business, but let’s talk a little bit about some of the processes in the business. As you mentioned, you have destination weddings.
Chris: 16:40 That’s what people come to you for. It’s like, hey, I want to go somewhere. I want to get married here. There is a lot of coordination, but like you said, you’re not a wedding planner. I have two questions for you Will. One is how did you define and stay in that lane of just the destination piece of the wedding and then two, talk to us a little bit about how you’re using ActiveCampaign to coordinate all of those dates.
Will: 17:05 Oh man, this is a really good one because the funny thing is that maybe because of a stigma or I don’t know. But I really didn’t consider destination weddings when I first started my business. In fact, it took me almost three years until I did one of the biggest bridal shows that I did back in Milwaukee. I remember I did that bridal show just because that’s what people told you that you needed to do if you needed more bookings.
Will: 17:41 Outside of joining the Chamber of Commerce and whatnot, that was one of the strategies that people used to talk about at conferences. I booked days with a couple of colleagues, and I kid you not Chris, I was so excited for this bridal show. It was huge. I remember, and my students all know this story, David Tutera was the keynote speaker and it was a big deal. But again, I didn’t go there to sell destination weddings.
Will: 18:18 I went there to sell honeymoons essentially because these brides were engaged, they weren’t going to have local weddings. Destination weddings was really not in my radar. I left that bridal show. Of course, I didn’t have ActiveCampaign. Of course I didn’t have an email sequence or any of that stuff. I was following up with these people manually via email. Of course I was not going to call them, I was scared of them telling me no.
Will: 18:42 I was like, okay, I didn’t know what I didn’t know back then. And after that I remember I left that, it was a big investment for me at the time and I made $0. That was almost $1,000 thrown down the drain were between the fee and printing brochures and things like that. I left there just feeling so defeated because nobody booked anything and I’m like, oh my God, I must suck.
Will: 19:13 After that I remember calling a member of the company I was affiliated with, we call them host agency, and my mentor at that time from the company I was like, hey listen, I’m calling to cancel a membership of being a travel agent. I’m calling to cancel because this sucks. I don’t know if can be paying this monthly fee and I just need to be done with this. I had already done one wedding for a former client of mine or a previous client of mine that I took on a group trip and that’s how I did my first one.
Will: 19:50 My mentor she goes, hey, let’s work it out. What if you did destination weddings? I think you have the personality for that and they’re really starting to come up and I’m like, what? Again, in my brain and where I was at that stage of my life there was kind of a stigma of me being a wedding planner. That’s what I thought that meant and I was like, oh, hell no. My family will laugh at me. No, that’s not what I want.
Will: 20:21 But I didn’t want to let her down. I went on to research a little bit about what were destination weddings and I found out that the key of the destination wedding was the group. Yes, you’re getting married but you’re bringing 50 people, 70 people, 100 people, whatever. From there I went to do all the training I could find online which was very, very limited. At the time it was basically just one on one how to and then what do I do next.
Will: 20:51 But I was like, okay, I’m game. I was already losing money anyways so I decided to rebrand. I rebranded, ordered new business cards and I really just went after destination weddings while booking my other travel clients that my referrals had gotten me to where I was up until that point. And then from there I really took a lot of just soul searching and really training and just exploring what that’d look like for me to niche down.
Will: 21:28 Once again, I was already not where I wanted to be so what did I have to lose by trying this niche for a year? That’s when things just started to roll in. I made the conscious decision that I wanted people to forget that I was a travel agent that could book their Disney trip for their family of three as long as they remember that I do groups and destination weddings once a year when someone gets engaged.
Chris: 21:58 Oh, that’s powerful Will.
Will: 22:01 I was willing to lose that business that I was already known for because I was at that point when I needed a transformation, I needed a change. Keeping those few families worked good, but I was going to pull out of business if I stayed with that because it was just not evolving fast enough and I was tired.
Chris: 22:27 I love it man. I’ve never heard it put that way but it immediately resonated when you said I was willing for them to forget me in this capacity in order for them to remember me in my new capacity. I have to say that is one of the pieces I see business owners struggle with so much because of course when you don’t understand marketing, you start out everybody’s your customer. My products are for everybody. And then as you realize that’s the fastest way to go broke and you start targeting your messaging and understanding that there’s a specific market that you need to target.
Chris: 23:07 And once you do that Will you’ll start attracting other people and you understand that dynamic, it’s really easy. It’s really easy to say, okay, I got it. It’s working great. The idea of pruning or cutting that out to operate in a new capacity. I see so many people in prison by the necessity of pruning that they never evolve in their business Will. Oh man, that was such a powerful statement you made.
Will: 23:36 I live by that because I see so many people in my community, in my industry struggle with that very decision and what is a definition of insanity. You’re doing the same thing and expecting different results. For me that was really powerful. I loved my business. I became a travel agent because I like to travel and I wanted to help people visit my home country which is the Dominican Republic so why don’t you help people do that? But then eventually after two or three years of you throwing money at this thing you just have to realize that it just becomes a very expensive hobby.
Will: 24:26 That’s not to say that travel agency and different niches are not making money. I have agent friends killing it even selling Disney vacations only. I have other agent friends killing it selling only cruises. I think the message there it’s really about following the passion, which as I mentioned before, might not necessarily be what you started with. But it’s just following what you’re passionate about and what pays the bills.
Will: 24:57 In my case I really just found a way to my initial niche or what I really knew was all inclusive vacations at resorts or beach resorts in Mexico and the Caribbean. Now I was just going to repackage that and instead of selling it to five different families a month, I was okay with selling it to just one couple for their weddings a month.
Chris: 25:23 Got it. I mean, it helps that you understood the space because even though you didn’t know what destination weddings were, you were still in that industry, in the wedding industry. You just changed your capacity. One thing that I learned about you just even more talking to you now is that you weren’t focused on engagement for the sake of engagement. It wasn’t one of those things where you were like, look at how many people we engage with every month, look at how many people joined my group. It was engagement to truly provide a service and understand the needs.
Chris: 26:02 That is of course admirable. But in our last few minutes Will, I’m looking at this thing and I’m seeing all of these moving parts. Destination wedding you have one person, you have their group of friends, maybe both parties group of friends just trying to coordinate and collaborate. This is briefly, but when it comes to facilitating that, managing that. Is the key that you identify the main stake holder and is that who is in the CRM? Is that who’s in ActiveCampaign with all of the date reminders and everything or how does that look?
Will: 26:40 Chris, I’m about keeping it simple. Here’s a big secret, everyone thinks I’m really techie and don’t get me wrong, I love technology but I’m not the guy that gets on the line for the new iPhone that comes out and I’m four hours standing in there. I don’t do that. It’s really funny because I always say I’m fast to try and slow to implement. Before I make a move I need to really analyze how all of these things are going to work for me and I’m not going to go and crazy in a week and try to do it all.
Will: 27:21 The way I use for my business in ActiveCampaign is actually really simple. I have two sides of it. The decision makers or the bride in this case, sometimes the groom, they connect with me somehow through my social media, through my consultation landing page, and automatically when they request information that links them to my nurture campaign which is automated in ActiveCampaign.
Will: 27:51 That is a very simple, I want to say I have 12 emails in there. Again, they’re simple, one, here you go. And then if they book the consultation, they get a tag and that tag now sends them a couple of different emails because they already booked a consultation. Then third part of that is if they hire me after that one hour complimentary consultation, then they get the next step emails.
Will: 28:21 Hey, thank you. Here’s what you should expect. I’ll be in touch with you within 48 hours and read this link, go to this link and I’ll be in touch. And then I take it from there manually because now we’re working one on one. And then the second piece of that is after they hire me, we choose the resort and let’s say we’re going to Cancun, Mexico and I spend the next 9 months, 12 months, sometimes even 15 months booking them and their wedding guests to this wedding.
Will: 28:56 Now, wedding is 10 months away. When we are finished with taking the payments from all of the group, then I have a very simple automation, with a personalization tag of course, that goes, hey Chris, you’re paid in full. Now what? I have perhaps 10 different emails that go out there based on the destination. Whether it’s 10 people going to that one wedding for Chris and his future Mrs or 150 people, they all get added to that one automation that goes to Cancun, Mexico and everybody over there gets into the same sequence over the next let’s say 60 days to prepare them.
Will: 29:40 These are their travel tips, getting ready type of thing. And to be honest, that’s as simple as I keep it in ActiveCampaign. Of course I’ve been using it now for a few years so I’ve tried up and down. I tried the CRM and this and that, but for my needs, the light plan has worked just fine.
Chris: 30:04 That’s powerful. I love it. You get the most out of it when you know exactly what you need it to do. It’s when you’re unclear on your own processes and you start using technology that you end up with more than you need or just enough but you don’t know how to use it Right.
Will: 30:25 Chris, can I say something real quick?
Chris: 30:27 Go ahead Will.
Will: 30:28 Let me have a fan girl moment here. Let me tell you something, I’ve heard that before and I’ve used that analogy, but it wasn’t until you said it in one of the podcast episode that I was listening to that you were talking about that. It feels so genuine to me that you were basically saying that ActiveCampaign may not be the answer, but you definitely start with a tool. I just never heard anyone say it like that before. And even though I practice that and I preach it and I teach to my students, I just never heard it set like that.
Will: 31:07 I’m like that makes sense. Now I’m having that same kind of challenge because people in my industry have gotten to know me as I speak about these systems and automations and whatnot and I have a lot of colleagues that they come to me and they want to hire me to show them the automation piece of my training in my business. I feel so challenged by that because I feel that I would be doing a disservice to them if I just took them through ActiveCampaign or whatever platform and just told them this is what you do. Take my template and pay me your money.
Will: 31:46 I have so much love and respect for my colleagues that I would never do that. I know that it took me a lot of learning and training and really digging into marketing to understand that if I have them jumping to the automation piece of the training or of their business before they actually even know who their ideal client is, how they want to systematize a certain processes or even have any emails written, I would be doing them a disservice.
Will: 32:18 I would just be taking their money. I don’t want to say that I don’t need the money because obviously we could all use more money, but it doesn’t go with the way I operate. If I’m helping you with something I want you to really understand it because I got burned by enough gurus showing me just one piece of the puzzle and then I was left in the dark and I had no idea what to do next.
Chris: 32:47 We see it a dime a dozen unfortunately. The good part is that we’re seeing a trend, a rise of more business owners like yourself who are willing to dedicate the time to learn how to use technology the right way to build a sustainable business and teach others to do the same. Thank you for that Will and thank you for coming on the podcast. This is door because I really want to hook you up here. If people want to know about planning a destination for their wedding or since you also do training Will, you also train other people. If there’s somebody on listening to this podcast who’s like, man, that’s really cool. I want to learn how to do that. Where should they go?
Will: 33:35 Thank you Chris and again, thank you for having me. I’m a fan of just your way of thinking and I think I over expressed in Miami when we met. But I genuinely meant that where I just feel that there needs to be more people like you that break it down and reput the strategy first before the tools. I’m super happy to hear that there is a rise on those business owners doing that. Anyways, about me. Very simple. I am known as Destination Weddings Expert. If you go to Instagram you find my account.
Will: 34:15 If you’re getting married and you need an agent that knows destination weddings, that have done dozens of them, you can just go to that account or destinationweddingsexpert.com. But if you’re a travel entrepreneur or a travel agent, travel consultant, looking to really niche into either groups or specifically destination weddings and systematizing all of those repetitive tasks and all of those awesome travel tips so that you don’t feel like you disappear after you collect the money and even convert.
Will: 34:48 I’m really good at sales if I say so myself. A big part of my training which is called the destination wedding playbook, it’s really about converting in sales because it’s not just for likes and followers on Instagram. We need to make that money. The website for that is willmedina.us as in the USA and you’ll be able to find me there and connect on Instagram. I love making friends and just talking business with people. That’s my jam.
Chris: 35:26 Great. Well Will, we have all of those links. They will be available in the show notes for everybody to easily click or if you just didn’t capture it for some reason, they will be there. Again Will, thank you so much for coming on the podcast. It’s always a great time. I’m so excited about what you’ve done and even more excited about what you’re about to do. Thanks again.
Will: 35:50 Thank you so much Chris.
Chris: 35:51 Okay, no problem. I’ll see you online.
Will: 35:54 All right, bye bye.