Ep 237: Grow Your Blog With Email Marketing & Relationship Building with Jessie Festa

Have you tried putting all your efforts into growing your blog but none of them seem to work? While you have been consistent and going the extra mile on creating quality content, you’re not achieving the results you wanted. What could possibly go wrong?

Joining me today in this special episode is Jessie Festa who will change your perspective around growing your blog. 

Jessie is the creator of the travel blogs Jessie on a Journey and Epicure & Culture. She is also the founder of Travel Blog Prosperity – a membership community for bloggers wanting to grow their traffic, community & income – as well as NYC Photo Journeys, a New York-based photography company. Her work has appeared in publications like USA Today, CNN, Business Insider, Thrillist, and WestJet Magazine.

We specifically talked about numerous topics, such as her journey into blogging, her success story, and email marketing strategies. We also discussed digital product sales, building affiliate partnerships, and valuable SEO tips.

Lastly, Jessie also shared her nifty 2-click tip from MediaVine, link building strategy, and her views about AI usage.

Are you someone who just bought a blog and wants to grow it? This episode is what you need! Tune in now to get started.

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Episode Highlights

03:40 Jessie’s travel blogging journey

08:16 Route on growing a blog

10:07 Revenue from blogging

17:53 SEO strategy and tips for bloggers

21:30 Generating revenue through emails

24:23 Growing an online business

26:21 Online business time management

28:34 Relationships in Blogging

34:55 AI tools for online businesses

37:52 Future Prospects in Blogging

Courses & Training

Courses & Training

Key Takeaways

➥ If Jessie would start travel blogging again, she will do it differently. Instead of immediately pursuing brand collaborations for quick earnings, she will prioritize building her website’s SEO and creating her own travel-related courses and memberships. Once she establishes a strong online presence and generates income independently, she will collaborate with brands. This strategy will allow her to have more control over her business, position herself as an authority, and attract meaningful brand partnerships in the long run.

At first, Jessie thought that SEO solely revolved around creating keyword. However, she soon realized that SEO encompassed a broader set of strategies. Jessie learned about SEO strategies and implemented them to her sites. 

Jessie’s income generation strategy revolves around email marketing. She uses social media to encourage her audience to join her email list. Through targeted email campaigns, she promotes her courses and memberships to generate sales. By leveraging the power of direct communication through email, she builds a closer relationship with her audience and nurtures their engagement, ultimately driving conversions and revenue for her travel blogging business.

About The Guest

Jessie Festa is the creator of the travel blogs Jessie on a Journey and Epicure & Culture. She is also the founder of Travel Blog Prosperity – a membership community for bloggers wanting to grow their traffic, community & income – as well as NYC Photo Journeys, a New York-based photography company. Her work has appeared in publications like USA Today, CNN, Business Insider, Thrillist, and WestJet Magazine.

Connect with Jessie Festa


Jaryd Krause:

How would you like to earn 30% of your income from your blog, and your own email list? Hi, I'm Jaryd Krause. I am the host of the Buying Online Businesses Podcast. And today, I'm speaking with Jessie Festa, who is the creator of the travel blogs Jessie on a Journey and Epicure & Culture. She was also the founder of Travel Blog Prosperity, which is a membership community for bloggers wanting to grow their traffic, community, and income, as well as New York City Photo Journeys, a New York-based photography company. Her work has appeared in publications like USA Today, CNN, Business Insider, Thrillist, and WestJet Magazine.

And in this podcast episode, Jessie and I specifically talk about why she started blogging and how she became successful with patience, how that was a big part of it for her and a part-time gig as well, and how that dynamic was very, very important for her. Also, my suggestions for people who want to make money online.

We also talk a lot about how it operates, and we break down the split in revenue between a few different things – digital products, affiliates, ads, partnerships, and all those sorts of things. And there's so many cool things that she's got going on that I feel that you're going to be able to tap into if you're going to buy a blog or re-own a blog.

We talk about things like email marketing. We talk about digital product sales. We talk about building affiliate partnerships and how to have high conversions with affiliate partnerships. She also discusses a nifty two-click tip from Mediavine. We talk about some SEO tips that she's picked up along the way. I asked her about link building.

Does she do it? If so, when does she do link building, and to which pages does she do link building? And we also touch on AI, when she uses it, and why we both don't use it as often at all. And there's so much value in this podcast episode. You guys are absolutely going to love it. Let's dive in.

What's up? This is Jaryd, and I am stoked to have you here. Before we dive into the show, I want to remind you that for a limited time, you can get one-to-one voice note mentoring with me to help you buy and grow your online business. I'm opening up just a few slots of voice note coaching to give you one-to-one access to me via Coachvox. You'll tell me your goals and challenges, and we'll work through them together.

I'll ask questions, I'll tell you what I think, and we'll get you ticking boxes and achieving your online income goals. You can message me anytime, and I'll respond within 48 hours. Right now, you can get 20% off by using the coupon code JARYD. That’s J-A-R-Y-D. And I'll drop the link in the show notes so you can find out more. Until then, let's get on with the episode.

Jessie, welcome to the pod.

Jessie Festa:

Thank you for having me.

Jaryd Krause:

I am curious to hear your story because it could have been mine. I first started trying to make money online with a travel blog as well. It was called Aus Globetrotter (ausglobetrotter.com). I literally typed into Google when I was living in Egypt. I'd done a lot of traveling, 40-ish countries or so, and I was like, I don't want to go back to plumbing, my job at the time. And I was living in Egypt, working as a divemaster, and I typed in, How do I travel the world and make money online? And that's what popped up, and I became a travel blogger for two years. And I realized, damn, it was pretty tough for the first two years. You are a travel blogger. Congratulations on making it. How long have you been traveling and blogging?

Jessie Festa:

So I started in 2011. And yes, in those early days, it is definitely tricky because you're working towards something that you kind of hope will come, but it's so different than if you get a normal nine-to-five job and it's like, Here's your salary and here are your benefits. You're kind of working towards something that you have in your head but that isn't there yet. So it can definitely be really, really tricky.

I definitely had another job on the side. I was a waitress and a freelance writer. So while I built it up, I still had money coming in. And I think that was really, really helpful versus kind of just canceling all that and just doing the blog on its own. I found it really helpful to have that side income, but it was also very flexible. Like it wasn't a nine to five, especially the freelance writing. I could do it from anywhere in the world, but I was still having money come in.

Jaryd Krause:

So you were doing freelance writing as your side gig while you were working on the blog?

Jessie Festa:

Yes, in those early days. I will sometimes freelance now, but not so much. It's pretty much all stuff with the blog unless a great opportunity arises. But yeah, for the first, I'd say two or three years, I was definitely doing a lot of freelance travel writing.

Jaryd Krause:

I love that. How do you think that is for a sense of security and for allowing less stress and emphasis on the blog panning out perfectly and working ASAP? How did you find that? Because I'm a big advocate for people, they want to buy a business, and I'm like, “Cool, let's go do it.” And they go, “I'm going to quit my job and we're going to buy a business.” I'm like, “No, don't do that.” It's worth having this other thing that's giving you an income still until you replace that income with another venture. What was that like for you? And do you recommend that to people when they start travel blogging or any online venture?

Jessie Festa:

Absolutely, yeah. I wanted to live on my own, go to restaurants, pay my bills, and pay my student loans that I had at the time. So, oh my gosh, I can't imagine if I didn't have some income coming in. I would have been a very nervous wreck about how I was going to pay my rent and stuff. But the thing with freelance travel writing that was so great was that while I was earning an income, I was also building backlinks.

I was building my brand because, when you freelance, you often get a bio. I was making amazing connections in the industry and really getting my name out there. So it was a way to make money, but that job in particular was also a way to help me grow my blog at the same time.

Jaryd Krause:

I love it. It's income that you can use to pay bills and also invest in the business. Why did you get into travel blogging or this whole make money online space? What was the motivation for that?

Jessie Festa:

Yeah. So I originally went to college with nonprofit PR in mind, but then I studied abroad, and I became hooked. I did travel more growing up with my parents, like to amusement parks, on road trips, and on Caribbean cruises, which I absolutely loved. But there was something so different about going across the world on my own.

I live in New York, and Australia is pretty far from there. So it was just such an incredible experience to be on my own, seeing these places that I'd never seen, having these new experiences. And I just really knew at that moment that this is something I want to continue doing.

I did not know what blogging was at this time because I don't remember what year it was. I started blogging in 2011, and I barely knew what a blog was at that point, but I had kind of researched travel jobs. I was a travel agent for a very short time. Didn't love that. I felt like that was more like sales than I thought it would be.

And then I saw these kinds of normal people who seemed just like me. When I thought of travel content creators at the time, I was thinking of Rick Steves and Samantha Brown. But these were normal people, not celebrities, getting paid to write about their travels. And I was like, Okay, I'm going to figure this out. I don't really know what this is, but I'm going to figure it out and make it happen.

Jaryd Krause:

Yeah, cool. That was the same energy that I had when I was like, I'm going to make this work no matter what. And I gave up on travel blogging. I started at a very similar time as you. You started in 2011. I started mine in 2013. I started it in 2013, ran it for about two years, and realized I wanted to make money faster. And I was just impatient. Tell me about impatience. Tell me about your patience or impatience with this whole journey.

Jessie Festa:

Yeah. I was able to take it full time in about a year, but it was mostly working with brands and sponsorships. Everyone is different. Personally, if I started again, my focus would definitely be on the SEO, the traffic, and getting the passive income first. I do still work with brands, and I do like paid press trips and stuff. But it's funny.

I feel like those are the things that get people into this, particularly travel. It's like, “Oh, I want to travel for free. I want to work with brands. I want to work with hotels.” But what people don't realize is that it is such an active way to make money. Sometimes even just setting myself up as a vendor in their system takes over an hour. And you haven't even started the project yet, right?

So if I were starting over again, I would definitely have worked hard on mastering SEO from day one, working towards Mediavine or whatever ad network you want to work with, and that affiliate income. And then, over the years, I've also launched my own kind of courses and memberships. I do tours and things like that. But yeah, I would have done passive first, then my own products, and then working with brand stuff would come kind of after that for me. For me personally. Everyone is different.

Jaryd Krause:

I think that a great way to go is to work on the SEO, make the content so damn good that you're going to get the traffic, build out some digital products, and have some affiliate programs without being affiliate partnerships where it requires you to actively work on it, like you mentioned before.

So what does that look like for you now? Since 2011, what's that? In the 12 years you've been blogging, Where does most of your revenue come from now? Is it, say, from Mediavine, 70%, or an affiliate and digital products? What's the split between those two, three, four, or five, however many you’ve got?

Jessie Festa:

Yeah, it's kind of split. Well, the way I kind of have my spreadsheet laid out, it's like Mediavine is one thing. I separate my products into courses, memberships, and tours, which I call influencer shoots and photo shoots here in New York City. So that's a separate thing. And I would say those three things are kind of even. Then it would be affiliate marketing and then working with brands and paid press trips for me at this point.

It's kind of when a great opportunity arises that I think sounds fun and something my audience would like, and it kind of lands in my lap, then I'll do it. But I don't actively pursue those things as much as I used to. It's still a good moneymaker, but it's got to be really good for me to want to. Like I said, it’s very active and time consuming to put together a campaign.

Jaryd Krause:

So what's the split between those? Would you say Mediavine is responsible for most of your revenue, followed by affiliate programs?

Jessie Festa:

I would say it's kind of split evenly. In the top three, it would be Mediavine, my courses and membership, and then my tours and influencer shoots. Mediavine is my favorite because it's totally passive. But with the courses and membership, the membership's great because you get the recurring revenue.

But I have loads of different kinds of sales funnels set up in the backend and things like that. So it's not a totally passive income because you do have to answer emails with the membership. I'm creating new content all the time, but I don't have to email my list every single day and say, “Hey, join my course.” It's kind of all running in the backend.

Jaryd Krause:

Yeah, definitely. Definitely. Memberships are a beautiful thing. They're so valuable for the people who are in them as well. As it scales, it just gets way more valuable. I run a membership, and people love it. I'm sure they love yours as well.

So there are so many things I want to dive into here in terms of your 80-20 in your day and the work that you are doing. What's your Pareto Principle? And what do you spend your time on? First, I want to dig into SEO. How did you learn SEO, and how did it evolve for you? Was it something that you were like, “Oh, I'm going to start a blog,” and then you started writing, and then did you realize, “Oh, I need to learn what keyword research is,” and stuff like that? How did this evolve for you, and what did you learn at different stages and why?

Jessie Festa:

Yeah. So I'm trying to remember. When I started, I thought SEO was just like choosing a keyword and thinking about it in your head. I don't think I fully understood the strategy involved. Even when I talk to a lot of my students and members, I'll ask them, “How's your knowledge of SEO?” And they're like, “Well, I put the keyword into the Yoast plugin.” And what they don't realize is, okay, that's not SEO. You need to have a strategy. Did you do keyword research? Did you find supporting keywords? Did you see that you could actually rank for this? There's so much more that goes into it.

In those early days, how did I learn SEO? When I first started, I definitely took a course. I don't think the course I took exists anymore, but that was step one for me because it was something so unfamiliar to me. I mean, even blogging in itself was super unfamiliar to me. So I wanted to learn what everything was. That course was definitely a little more geared towards how to be a better writer, how to work with brands, and learning about paid press trips. So it didn't get into SEO so much.

I think I learned it from an eBook and watching YouTube videos, kind of learning as I went. Now the main tool I use for everything is key search. Looking at that first page, I wondered if I could rank for something. There are a few keyword research strategies I use. Sometimes I kind of start with an idea and look at the supporting ideas.

Sometimes I'll do competitor research. I always think that's a great way to go because you have that hard data of what's actually bringing people traffic. I'll do research sometimes to see if there's maybe a forum post I can outrank. So now I have a few different strategies that I use to find keywords.

But yeah, at this point, I think one of my favorite little tips that's non-technical is to write about the same topic all the time. It's going to make it a lot easier to rank. So for me, at this point, because I'm a solo female traveler, if I want to write about a solo female travel guide, that's usually my go-to type of content. I have a pretty good idea of what I want to do, if I could rank it, what the outline will be, and things like that.

Jaryd Krause:

I love it. And I want to talk about what you mentioned there and break it down. And why is it easier to rank a certain topic if you cover it multiple times? For example, for solo female travel, I want to explain this to people listening so they understand what topical authority is and how you can generate it.

You want to rank for solo female travel, but there's a longer phrase or long-tail keyword at the start or before the three words “solo female travel”. That could be solo female travel in Bali, solo female travel in Australia, or solo female travel in all these different places. But what you're doing is showing Google that the more content you create around solo female travel, the more authority you're building in that space. And when you do create another article around that, it's easier for you to rank for it because you've already established topical authority in that space. And Google's like, “Yeah, cool. You've nailed this topic. We're going to rank that.” Is that what you mean by that?

Jessie Festa:

Absolutely. And I see it with my own students and members all the time. They're so resistant, and I get it. Because we're all multifaceted people, we want to write about everything. But once they niche down, for the people who actually are like, “Okay, I'll do it,” the results are incredible. Like one woman, I hadn't seen her in a bit, and I knew she had been struggling for a while. I connected with her two weeks ago.

I'm like, “Wow, you are doing amazing online.” Just her site has improved, and her social media has a ton of engagement. And I was like, “What'd you change?” And she's like, “Now I just write about the city I live in.” And it just made all the difference for her.

And I know, for me, I have Jessie on a Journey, but I also have a much smaller site that outranks other sites all the time because it's for my tour company. It's all about NYC travel. So I outrank bigger sites all the time. And I know I have another friend who has, I would call a big travel blog, but they kind of cover everything. Her and her husband just started a fully Brooklyn travel site, say, a year ago. And they're kind of focusing fully on that now because they're like, “It's just so much easier to grow.”

Jaryd Krause

: Yeah. Because you got hyper focus. Hyperfocus and Google know, “Okay, this is what this is about. Yeah, you're covering the thing that you're actually talking about in multiple different places.”

So thinking about SEO, you've mentioned keywords and how you go about that. And then we also covered topical authority. What do you think is the most important SEO strategy, SEO tool, or SEO tip that you use on your blog?

Jessie Festa:

Yeah. So along with the topical authority, one tip I always give people is to try to move your links as close to the homepage as possible. So what I do is create what I call a silo page. I mean, there are so many different names for this thing, like cornerstone content or hub page. But on a page where, let's say, you have three main topics you cover, You'd create a page for each of those topics and link each of those pages in your main menu or somewhere on your homepage. The main menu, I think, usually makes the most sense. Then, when new content gets published on one of those topics, you link it to the relevant page.

So for me, I have a solo female travel guide silo page. And if I write about solo female travel in Bali, I will then link to it on that page. If I write about solo female travel in NYC, I will link it to that page. And what I'm always trying to do is get my links no more than two clicks from the homepage. This is actually a tip I learned from Mediavine themselves.

Jaryd Krause:

What do you mean by no more than two clicks from the homepage?

Jessie Festa:

I can't link to every article I write in my menu. That would be crazy. I have over 1,000 blog posts. So the first click would be on the actual silo page, and the second click would be on that silo page. Does that make sense? I know that's hard without a visual.

Jaryd Krause:

Yeah. So solo female travel One click would be on a solo female traveler. Another option would be solo female travel in Bali. And that's two.

Jessie Festa:

Exactly, yeah.

Jaryd Krause:

Yeah. Okay, got you. So you never want any one piece of content to be more than two clicks away from the homepage.

Jessie Festa:

At least the ones you want to rank. Some people have pages that maybe have no index or whatever. But for the blog posts and pages that you want to rank, I would get those closer to the homepage.

Jaryd Krause:

I love it. I love it. It's great for the user experience, too. That's what Google is all about. What other cool little nifty tricks have you learned from either Mediavine, some of the courses that you've taken, or just the data that you've found yourself?

Jessie Festa:

Yeah. Not so much SEO, but one thing for traffic. Because I know SEO and traffic are really related, I think a missed opportunity—I work with bloggers in the travel space, so I really know that niche—is growing your email list.

I always get people saying, “Oh, I'm posting on Instagram all the time, but I'm not getting traffic.” And I kind of remind people that Instagram is great for working with brands or connecting with your community. But people are scrolling on that; they're not really clicking away. On your email list, you can not only promote your own products and affiliate links if the affiliate program allows email promotion, but you can also let them know about your new blog posts, your podcast episodes, and your YouTube videos. And I do great with traffic directly from the newsletter. I mean, I would say 90% of my traffic is SEO. But after that, in terms of newsletter versus social, my newsletter would be the next thing.

Jaryd Krause:

You're singing my song here. I don't think enough bloggers use their email list as well as they should, and leave so much on the table, especially in terms of revenue. It's cool to see that, yeah, we're getting a bunch of traffic coming back from the email list to the site. That's great for SEO. But the amount of money people leave on the table without tapping into their email list is insane. So tell me about how you generate revenue through your email list.

Jessie Festa:

Yeah. So along with sending traffic to the site, which could be maybe Mediavine and affiliate income, I would say, Oh my gosh, probably 100% of my core sales come through my email list in some way. Whether it's through a sales funnel that gets them onto the email list, or, I mean, the way I really use social media,

If I'm launching a course or relaunching my membership, I'll mention it on social media. But really, the way I use social media to sell is to promote opt-in freebies or some kind of incentive to get on my email list or join a webinar or whatever, which is essentially an opt-in freebie, getting people onto the list, and then I'm promoting.

Yeah, I would say probably 99% of my sales are from the email list. Or at least from people who, if it's not from a sales funnel or a launch, they've been on my list for a bit and they're kind of like, “Okay, I'm ready, Jessie. I know you tell us about blogging tips every week. I know you have this membership. How can I join?” All the magic is on the email list.

Jaryd Krause:

That's just so good. So you say that the most important thing between the top three is Mediavine, affiliates, and your digital products and course sales. So let's just say, for example, that it’s 33% recurring between those three, and then about 100% of your sales for the course and digital products are from your email list, which means roughly 33% of your revenue for your whole business is through email.

Jessie Festa:

Kind of. And then my tours. So the tours and photo shoots I started selling on my blog were because I basically had a lot of readers asking me to show them around New York City, and I never thought I would start a tour company. I just had so many readers ask this. I was like, Okay, I see an opportunity here.

So at first, I just sold those through my blog. It's a very active way to make money. It does very, very well for me, so I nurture it for now, but it is a company that I will eventually want to sell. So it's NYC Photo Journeys. It has its own website, but I link it to all of my New York City content in Jessie on a Journey.

So actually, almost all my sales for the tours come through SEO traffic, either through Jessie on a Journey blog posts or blog posts and pages directly on that website. A little bit of affiliates. I do have an affiliate program for the tours, and I do have some affiliates sending bookings my way. But it's a lot of SEO. And then TripAdvisor reviews too, so TripAdvisor bookings.

Jaryd Krause:

Awesome. That's really cool, setting it up. And that's a really good thing for people to think about. When they're in business, they think, “Well, how do I grow this business?” And they go away outside of their business and research ways that they can grow the business. Whereas if the business and the people on your email list and people on your blog reading your posts are saying, “Here, we want this,” you give them that, and they'll pay for it. That's the best way to grow your business; it’s inside-out growth, right? Have you found that to be the best way you've grown your business?

Jessie Festa:

Yeah. And it's always amazing to me how many people don’t—not so much the bloggers I work with, but other business owners. I also know a lot of tour company owners in New York City, and I don't think almost any of them have a blog. A lot of them are kind of doing social media, but I'm not really sure how they make most of their sales, to be honest.

None of them are utilizing blogging, though. And it's just, to me, such a missed opportunity. Because, yeah, you do have to put the time into learning SEO and creating the content. But articles, for me, once they're ranking, they rank for a really long time—years and years and years—so that blog post that's ranking today could keep bringing you bookings for years to come.

And one thing I like to do, and I try to do this every month, is look at my analytics and see what my top posts are. Because sometimes that changes based on new content and things shifting around. And I'll check, did I add affiliate links, did I add calls-to-action, did I add opt-in freebie calls-to-action, getting people onto my email list? And every single time I see a ton of missed opportunities, Maybe some of the affiliate links are broken. And those are posts that already have a ton of people reading them. So you want to make sure those are well-optimized since you already have the eyes there.

Jaryd Krause:

Yeah. So I guess that brings me to the question I want to find out. Where do you spend most of your time on your blog? And is it creating new content? Is it going back and updating the content? What are some of, I'd say, the top three tasks that you do for running this blog to get the best results?

Jessie Festa:

Yeah. It looks so different all the time. I'll say that today I spent most of the day editing a blog post, and now I'm fortunate that I'm at a point where I do have some people helping. I have some writers. I have some people who post updates, especially for SEO. You could always look in your Google Search Console. For anyone who uses that tool, you definitely should if you have a website. It's free.

Jaryd Krause:

So maybe we go high level and not just into the tactical of if it changes day to day, which I'm sure it does. What about from quarter to quarter or each year? What are the top three buckets that you would focus on for growing the blog?

Jessie Festa:

Yeah. So I mean, for just strategies for growing, I would definitely say creating new content. I also update every month, but I could do that quicker. I could really dedicate three days to doing a couple updates. So I would say creating new content and doing outreach to do collaborations with other creators and affiliates

So I will swap, say, webinars, so I'm able to promote my courses to their audience, they can promote theirs to mine, and we get in front of each other's audience. That's another thing I put a lot of time into. And my email list, setting up, and kind of making sure all my funnels are working properly.

Today, I actually realized that one of my webinar videos hasn't been working for over a month. I've been away traveling. So now I'm like, Okay, I've got to fix that. But you need to kind of check in on these things. Realistically, I should have checked that a little sooner. But that is an important thing to check since that does bring a lot of new people into my business.

Jaryd Krause:

Sweet. So new content, email, and relationships—how important have you found relationships in blogging?

Jessie Festa:

Yeah. I try to do one day a month where I also just do outreach. I reach out to people who might want to be guest teachers in my membership, who might want to swap guest emails where I'm sharing tips, and also offer an opt-in freebie to get people from their audience onto my list. Swap webinars. I'll reach out to people that I think would be great affiliates for either my courses or my tours. And some of it might be working with brands or pitching. But, like I said, I do that a lot less nowadays. I'd rather focus on growing my digital products, my membership, and things like that.

But yeah, I definitely have found that to a) be a really great way to grow quite quickly, and b) be a lot of fun. It's fun to connect with other bloggers. But if you find another blogger who has a really engaged email list of bloggers, particularly if they don't have competing products with you, but have the audience you want to get in front of, that's a great way to get a bunch of people on your list right away.

Jaryd Krause:

I love that you said non-competing products, but at the same time, if they have a complementary audience to your products or what you do, it's a huge win for you both, right? You can sell their products and get an affiliate commission, and you can give them an affiliate commission for selling your products.

And even if somebody doesn't have an affiliate product or their own digital product, you could just give them free gifts. Like you said, a webinar or even the basic old eBook, which has been beaten to death, I believe people should have far smarter and cooler opt-ins and stuff like that these days. But you can just share, “Hey, how would your audience like this?

Let's do swapsies.” I like that rather than you just going, “Hey, can I give this to your list, and they get on my email list? ” and they get nothing in return. How big is that in terms of creating a successful partnership by giving the same amount of value back to one another? How big is that for conversions for you?

Jessie Festa:

In terms of making it an equal partnership?

Jaryd Krause:

Yeah. Or making it a partnership that works and that people want to say yes to, I guess.

Jessie Festa:

Yeah. For me, whether I'm pitching a brand, an affiliate, I'll swap webinars, not really swap webinars. I've reached out to certain affiliates to teach a webinar for my audience and use my affiliate link. I do that too.

If I'm pitching an idea, I'm re-reading it to make sure it sounds like a win-win. If I'm asking for something, I'm always putting something in there where it's like, “What can I do for you too?” Especially if it's someone that's not a close personal friend, let's say, which is most of the pitches I send. A lot of them are maybe people I've met once, or maybe we've spoken at an online summit together or done a bundle together.

I always note the names of those people. I actually have a whole spreadsheet just because I'm like, Okay, these are people that are probably collaborative. Next time around, when I'm reaching out to people, I'm going to look at what they do and see if there are maybe some opportunities for us to work together in some way.

Jaryd Krause:

I love it. In our business, we have a relationship spreadsheet for each different department. You just see Google Sheets, and different people that run the different parts of that will put in names and emails and what they're on the list for. And it's so important, I think, to track relationships because relationships are everything, in everything,, in business and life. The quality of your relationships is so important.

I want to speak about link building. Is this a thing that you do? And when do you decide to do it and for which pieces of content?

Jessie Festa:

Yeah. When I have new content, I always try to find opportunities for link building. I think it's really important. I think it's always important, but I always tell newer bloggers that it can definitely help you grow much quicker. When you first start a new blog, it does take time for Google to trust you. But if you could get the backing of other blogs, bigger blogs, you could guest post, or do collaborative posts. I publish a lot of those, and I take part in a lot of them. It could be really, really helpful to just get those votes of confidence from other people.

Jaryd Krause:

And so for each new blog post, do you do a link building campaign? Do you ever do it when you realize, Oh, this post has done well, or I want it to do better? How do you decide which blogs or posts to build links to?

Jessie Festa:

Yeah. I kind of do a mix. And I'll be honest, I don't track this as much as I should or do full-on campaigns for it. It's kind of two totally different things. Either one has really high-traffic potential and a high ranking, but I want to keep it there. I will continue to build links to it because I don't want to lose its position. Or if I see one that's maybe in position three or four and I want to bump it up a little bit, I'll do that. If I publish a post and it's in the middle of page two, I usually don't try so hard. I'd rather move a post from position six to three than from 20 to 15.

Jaryd Krause:

Yeah, yeah, I agree. Focus on more of what's working and less of what's not working. It's a great approach.

What's interesting is AI. AI has become, I would say, the biggest shiny object syndrome in online businesses—maybe not today, but as of right now. And I'm all for it. I think it's good, and I have zero fear of it. I love change because it forces everybody else to change, and I'm super adaptable. And I think everybody else listening should be adaptable and not worry about it. Because if you're open to change, then there's a massive opportunity in that. With AI, do you use any AI tools for your business?

Jessie Festa:

Very little. I'm not against it. I have such a flow and strategy for what I've been doing that I haven't really felt the need for it. But one thing I do use it for—this is brand new; I've just started kind of doing this—is to keep it open. And usually, if it's a guest post, it's more on a topic I'm not totally familiar with. Like today, I was editing something about Lyon in France, and I don't know that city super well.

So the writer didn't. The nightlife section was really short. So I wanted to add to it. So I went to ChatGPT, and I was just kind of like, “What nightlife options are there in Lyon?” And then I kind of took a few of those ideas and asked it more questions to just get ideas about what I could add to it very quickly and easily.

But in terms of having it create outlines or really having it create the content for me, I haven't done so much. I have used it for Pinterest pins. But for the blog, not as much. Just more like that assistant to help me do a little research.

Jaryd Krause:

It's fascinating and interesting, and I find this in my own business, that when you've owned your business for a while and you've got your own systems and processes put in place to create or finish a job or create content or whatever it is, often those systems and processes are so heavily refined to provide the content or create the thing that you actually want in your business exactly how you want it.

And then in come these AI tools, and I'm like, “Oh, I can make this process faster, simpler, and easier.” Yeah, cool. And I've tried that with a lot of different things in my business and realized that, hey, I've just wasted my time here with this tool because it's not providing the result that I actually want. It's just been a distraction. I'd have to pay for this tool and get all these other tools that aren't going to give me the great quality content or whatever it is that I'm doing in my business that I'm already getting.

Jessie Festa:
Exactly. Again, I have such a system down that I'm just like, Oh my gosh, it's going to take me so long to invest in refining it because I know you have to be very specific with the exact prompts. Because I've done general testing, I said, “Create an outline for this.” And the outline it creates is just a crazy mishmash of what already exists, and it's not great.

I would need to completely redo it. So at first glance, I feel it's a little more work than necessary. However, I do have friends that use it and love it, but they say it does take time to understand the correct prompts and refine them. So I'm like, Well, if what I'm doing already works for now, I'm going to keep doing what I'm already doing.

Jaryd Krause:

Yeah, exactly. I love it. So as your blog continues to grow and evolve, are you looking to take it in new directions or do different things? And what's that going to look like in the future for you?

Jessie Festa:

Yeah. The one new thing that's kind of becoming bigger this year almost by accident is speaking, which I really like. I've always spoken at travel conferences. But this year, I've just been asked to do a bunch of different kinds of speaking gigs that I've really loved. I've kind of done one a month, and I've loved it.

So I'm going to try to keep that going. But other than that, just building out—not necessarily building out more courses but perfecting the ones I have and just continuing to build on my membership—Of all the things I've created, my membership is really like my baby. It’s Travel Blog Prosperity.

It's such an amazing community that's just super supportive. I mean, we have the educational portion, but I think you said before that the community aspect is just so incredible. And not only do I love it for the monetization that it brings to my business, but I actually love hopping on the calls with everyone.

And I was on a call right before this with one of the members, and I just absolutely love being a part of it too. So just continuing to grow that and take it to the next level would be the other focus. And then continuing to build the traffic because Mediavine is the other beloved monetization stream.

Jaryd Krause:

Yeah. And you've got the Profitable Travel Blogger Podcast, right? And how often do you publish?

Jessie Festa:

Yeah. So I take summers and winters off. Not full winters, but kind of like the holiday break. But outside of that, I publish every other week.

Jaryd Krause:

Cool, cool. Yeah. Well, thank you so much for coming on and sharing where you're at and what you've done. It's absolutely awesome. I'm absolutely stoked with how much you lean into your email list. It's really cool. Especially with people listening, they just don't tap into it.

Jessie Festa:

Yeah. Oh my gosh. If you are not growing an email list, don't wait. Make that next on your to-do list.

Jaryd Krause:

Definitely leaving money on the table. So I want to link to your site, jessieonjourney.com. I'm also going to link to your podcast as well. Is there anywhere else that you want to send people to check out more about what you're doing?

Jessie Festa:

Yeah. If you go to my site, jessieonjourney.com, there's a blogging tab in the menu, and then you'll be taken to a whole other section of my site with free webinars and different principles and things like that if you are specifically interested in learning how to grow a blog. And then beyond that, I do have a YouTube channel called Make Money Travel Blogging w/ Jessie on a Journey.

Jaryd Krause:

Awesome, guys, check it out. I'll put links to those in the show notes. Jessie, thank you so much for coming on. Everybody who is listening, thank you for listening. I really do appreciate your love, your support. I don't ask for people to subscribe or leave reviews, but if you could share the love by sharing this podcast episode, that would be greatly helpful for someone who is wanting to buy and scale a blog. So that would be really cool. Thanks, Jessie.

Jessie Festa:

Thank you.

Jaryd Krause:


Jessie Festa:


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Jaryd Krause is a serial entrepreneur who helps people buy online businesses so they can spend more time doing what they love with who they love. He’s helped people buy and scale sites all the way up to 8 figures – from eCommerce to content websites. He spends his time surfing and traveling, and his biggest goals are around making a real tangible impact on people’s lives. 

Resource Links:

➥ Buying Online Businesses Website – https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework – https://buyingonlinebusinesses.com/freeresources/

  Get 1-1 voice note coaching with Jaryd – https://app.coachvox.com/profile/jaryd-krause

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Semrush (SEO tool) – https://bit.ly/3lINGaV

Surfer SEO (SEO tool for content writing) – https://bit.ly/3X0jZiD

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