Young and Profiting with Hala Taha - Jenna Kutcher: Turn Your Side Hustle into a 7-Figure Online Business | Entrepreneurship | YAPLive

Episode Date: July 11, 2025

Now on Spotify Video! After realizing that climbing the corporate ladder didn’t bring fulfillment, Jenna Kutcher left her stable job to start a photography business. But by the time she scaled it to six figures, she was burned out. Determined to create a more sustainable lifestyle, she pursued multiple side hustles, worked on her own terms, and built various income streams, ultimately creating a multi-million-dollar online business. In this episode, Jenna shares the strategies that helped her build passive income, scale her business, all while fiercely protecting her work-life balance. In this episode, Hala and Jenna will discuss:  (00:00) Introduction (00:53) Quitting Her Corporate Job to Start a Business (05:21) Creating Online Courses as a Side Hustle (09:10) Growing Your Audience on Social Media (14:32) Scaling to 7 Figures Through Affiliate Marketing (18:30) Marketing Tips for Entrepreneurs with a Small Following (22:01) The Journey to Real Estate Investment (30:58) Building a Business with Your Partner (32:58) Prioritizing Family Over Opportunities Jenna Kutcher is an entrepreneur, online marketing expert, author, and the host of the Goal Digger Podcast. She is also a digital educator and has created multi-million-dollar revenue streams through online courses, affiliate marketing, podcasting, and real estate. Jenna has built a massive online following by authentically sharing her journey and empowering women to create businesses they love and lives they enjoy. Sponsored By: Shopify - Start your $1/month trial at Shopify.com/profiting. Indeed - Get a $75 sponsored job credit to boost your job's visibility at Indeed.com/PROFITING OpenPhone - Get 20% off your first 6 months at OpenPhone.com/profiting. Airbnb - Find a co-host at airbnb.com/host Boulevard - Get 10% off your first year at joinblvd.com/profiting when you book a demo   Resources Mentioned: Jenna’s Podcast, Goal Digger Podcast: bit.ly/TGDP-apple  Jenna’s Instagram: instagram.com/jennakutcher Active Deals - youngandprofiting.com/deals  Key YAP Links Reviews - ratethispodcast.com/yap Youtube - youtube.com/c/YoungandProfiting LinkedIn - linkedin.com/in/htaha/ Instagram - instagram.com/yapwithhala/ Social + Podcast Services: yapmedia.com Transcripts - youngandprofiting.com/episodes-new  Entrepreneurship, Entrepreneurship Podcast, Business, Business Podcast, Self Improvement, Self-Improvement, Personal Development, Starting a Business, Strategy, Investing, Sales, Selling, Psychology, Productivity, Entrepreneurs, AI, Artificial Intelligence, Technology, Marketing, Negotiation, Money, Finance, Side Hustle, Startup, Mental Health, Career, Leadership, Mindset, Health, Growth Mindset, Entrepreneurship, Entrepreneurship Podcast, Business Podcast, Startup, Solopreneur, Founder, Networking

We focus so much on, like, leaving a legacy, but I think in reality, we have to focus on living a legacy. Jenna Coochard. Jenna Coochard. She's the host of the Gold Digger podcast. She's a bestselling author, and she's also an entrepreneur of many different businesses. You've got like a million plus followers on Instagram. You're huge on Pinterest. How did that piece come about?

It all grew super organically until it didn't. Even in the early days, I would just share my life. And it really made me realize, like, people need to connect with people. I heard this statistic of, like, the average millionaire has seven revenue streams. And at the time, I had one. And I was like, how do we figure this out? Like, what could this even look like? It felt so crazy.

I have had to learn how to discern, like, what are my best yeses? And, like, what can I say no to without having FOMO, without having guilt? In the beginning, you have to trade time for money. That is the hustle that is required. Boundaries aren't bad. It's a muscle that you have to learn to flex, and it takes time. We do seven figures in affiliate marketing each year. I look at marketing very distilled down.

There are two focuses. The first primary focus is... Hey, everyone. Welcome to the show. We've got an exciting episode in store for you today. We are live in an Airbnb location, which is coincidental because we actually talked about Airbnb in this episode. Today, I'm interviewing Jenna Cutcher. She's the host of the Gold Digger podcast.

She's a bestselling author. And she's also an entrepreneur of many different businesses. So we're going to talk about all the different ways she makes money from her courses to affiliate marketing to podcast sponsorships to hosting a property on Airbnb. I absolutely love this conversation. Jenna is one of my close friends. And she's so smart. She's so brilliant. I can't wait to share it with you all.

So without further ado, here's my conversation with Jenna Coucher. Jenna, welcome to Young and Profiting Podcast. Thank you. I mean, let's talk about money, but money is such a taboo topic, especially with women. And so we're going to kind of dive off the deep end together. Yes. Let's do it. So, first of all, tell me, what was the first way that you started to make a lot of money?

Like, when did it all start to really come together for you? Okay. So when I was 23, I worked in corporate America, and I had a great job, but I very quickly realized that climbing the corporate ladder was just not for me. And it is an amazing option for a lot of people. It just didn't resonate with my soul. Like there was just this feeling of like, I've got to figure something else out. So I started as a wedding photographer.

Most people know my story. I bought a $300 camera on Craigslist, ended up starting a wedding photography business, taught myself everything. And within three years, I was earning six figures, which at the time was more than I had ever even dreamed of, right? In my corporate job, I was making $50,000 a year. I felt so rich. making six figures felt like this amount that was like impossible. And when I was growing my business,

I was also experiencing burnout. And I had grown so quickly, which was such a blessing. But I also just hit this place where I was like, I can't imagine doing this for the next five, 10, 15, 20 years. Like there's got to be a different way. And I committed to figuring out a different way through loss. And I shared this story many times, but when my husband and I finally decided that we wanted to start a family, it didn't happen as easily for us as it does for other people. And I know a lot of people experienced this, but we went through two miscarriages. And I was planning my pregnancies around my photography business because I was shooting in the summer and I had to figure out, like, how was this going to work? And when I had my second loss, I had to show up and shoot a wedding the next day.

And I was like, there has to be a different way. Like, I built this amazing business, but if I don't show up and shoot, I don't get paid. And there's got to be a different way. And so I committed then and there in this moment of like agony of like, I will figure this out. And I remember around that time, I heard this statistic of like the average millionaire has seven revenue streams. And at the time, I had one. And I was like, how do we figure this out?

Like, what could this even look like? It felt so crazy. And so I. started many different side hustles. Do you want to dive? Yeah. Okay. So my first side hustle was I became a watercolor artist. Oh my god, no. So my mother-in-law was an elementary art teacher and in the basement of her house, she had all of these art supplies. And in my season of burnout, I was like, I need to do something to connect back to my creativity. Like at first, my photography was my creativity and then it became my job. And so I went home with all these watercolor supplies. I started painting every day. I forced

myself to sit in a chair and paint for 20 minutes a day. And I started sharing these paintings on the internet and people were like, can I buy that? Amazing. I ended up figuring out a way to scan these watercolor prints and sell them online. And pretty soon we were paying our mortgage with the print revenue. Your first sort of passive income revenue. Totally, because that was what made me realize I could create something once and sell it a bunch of times. So it started as like a joke and it turned into something where I was like, wait a minute, like we're on to something. Also around that time was when I had realized after hitting six figures that I was happier when I was working less. And I had hit this point. And I think a lot of entrepreneurs hit this point where in the

beginning, you have to trade time for money. There's really no other way around it. That is the hustle that is required. But at some point, when you start to get the money, you recognize that I will spend money to get back my time. And I'd hit that point in my photography business. And I was like, you know what, I will go back to earning $50,000 a year if I can have a life. And so I committed to booking half of the weddings that I had been shooting. And I said, I'm going to figure something else out. And so that's when I started learning about online courses. And I had scaled a business from zero to 100K in three years. I knew something that a lot of people didn't. And so I started mentoring other local photographers, having them come into this little condo we lived in. And I would walk them through,

pricing, marketing, social media, like all the business stuff. Because I'm like, these people are so good at their craft. They don't know how to like sell it. And so I started coaching. Then I started looking into online courses. And that's kind of where the business that people see today started to form. But it was years in the making. I love that. It's so inspiring. So in terms of your courses, how did you first like figure out how to go from one to one to one to many? Because that's really the secret. It's like, how do you take what you do to individuals and then make it possible that many people can take this course? Like, how did you first start to figure that world out? Yeah. You know, it's kind of funny because I don't know if I've ever drawn the parallel of like making a watercolor print,

scanning it, figuring out one to one or one to many. And that is exactly what online education is. And it was so funny because I ended up coaching five local photographers and they all had the same questions. And all of a sudden, I found myself, I'm like, I am a broken record. I'm teaching them the same things. I'm showing them the same pricing guides. I'm walking through the same things. And that was when I really started to discern, like, there are trends and questions that everybody has. And that is the type of content you want to put into an online course. And I am so grateful that I took the time to sit down with people face to face, hear their struggles, understand, like, well, what am I actually doing different? Because I think that so often we are so

close to our own genius that we think everybody knows this. Surely this is easy for everybody. And so when I started to identify these trends, I was like, oh my gosh, I can, I can teach branding and I can teach social media and I can teach pricing and I can teach email communication and all of these things. And so I created my first online course after taking an online course. So I was like, I'm going to buy an online course and figure out, okay, how did they deliver it? How was it recorded? How was it like spread out over the weeks? Yes. That is like my secret. sauce is like reverse engineering. Like I see an end result as a wedding photographer. I would see the finished shot and I would think, how did the photographer pose these people this way? What were

the cues that they gave them? What was the lighting? And I reverse engineered course creation because I was like, I can figure this out. I know I can. It's like the people that can take a part of car and figure out how to put it back together. I can't do that. But when it comes to digital stuff, I'm so good at that. And so online courses like cracked my life open in such a beautiful way. But it did, it allowed me to reach people outside of where we lived in this tiny village in Wisconsin, and it allowed me to connect with other photographers who were struggling with the same thing so that they could really focus on the art and their craft. Yeah. Yeah, we have a super unique company culture. We're all about obsessive excellence. We even call ourselves scrappy hustlers. And I'm really

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I really want your help, but I can't afford your services. I really want your help, but I can't afford your services. And then I realized that this agency that I'm building, in order to get more clients, every time I get three more clients, I have to hire five more people. And I don't want to have like a 3,000 person organization. That's a lot of stress on me. So I was like, what can I do to sort of lay it all out and the same trainings that I give my team, the same checklists I give them? How can I take what I give my team to service my clients and then turn it into a class. And then I did that and I just used everything that we already had. So the course was like very fast to put together because I think a lot of people don't realize that if you have an agency,

you probably have a course because whatever you're doing, you can package it up and teach other people how to do what you do to service your clients. And I feel like a lot of people don't realize that. The other thing with courses is that it just gives you so much content to then create an audience and attract an audience. So for example, I have like a two-day master class. on LinkedIn, and my team literally just goes to the slides that I created and then creates posts. You know what I mean? Because they have all the content. I've written it all down. So I'd love to understand how did you end up becoming an influencer? Because you've got like a million plus followers on Instagram. You're huge on Pinterest too. And so just curious of how did that

piece come about? Was the podcast the first thing that kicked that all off? No. I mean, it all grew super organically until it didn't. So when I was a wedding photographer, I realized really quickly that there were a million wedding photographers in my area that were really talented. And the only thing that made me different was me because we were all delivering a very similar finished product. And so even in the early days, and I mean, this is like OG Instagram. We're talking here. Like when we used to use those weird like Valencia filters, I would just share my life. And I I would just share who I was and what I was struggling with. I would share working from home with no makeup on. Like, this is the reality of it. And it was so interesting because when I first became

wedding photographer, I just hid behind my work. It was like the safe spot. I figured surely everyone only wants to see my work. And I remember years and years and years ago polling my audience of like, what are your favorite posts? And it was all personal. And I was like, what is this? And so fast forward a few years. We went to Hawaii and I wanted to do an experiment and I love experimenting. I am like a huge experimenter. And so I said for 30 days, I'm going to only post me. And this is at a time when I've been hiding behind my work for years. And my engagement skyrocketed. My confidence in myself grew. My connection to my audience grew. And I was like so fascinated by it because I was like, this seems like the least interesting thing of like what I'm doing. It was just sharing my life.

And it really made me realize like people need to connect with people. And I never set out to be an influencer. I really wanted to just like continue to grow and share. And I really have realized over the last few years of like my dream is to like help women build businesses they don't hate and build lives that they love. And I have been taking people on this journey, not as like I have figure this all out, but like, I am still learning. I am still growing. I'm still figuring this out. And so when I started doing like social media collaborations and social media promotions and different things like that, it just felt so natural because I am the kind of person where I'm like, oh my God, have you tried this new lip gloss or like this skin like cleanser is life changing.

Like I am naturally like when I go on a girl's date with my girlfriends, by the end of the day, I've dropped like 10 links of things that I'm just telling them about because I'm like, if this works for me, this could work for you. Like I just love not gatekeeping, whether it's business or like beauty products or whatever that is. And so that was just such an interesting like facet for me to realize like people care about the business, yes, but they also care about like what's happening behind the business and like what's fueling it. And so that was interesting. We did have a viral moment. So I grew very organically. I felt like I knew every single follower. Like I just, it felt that way. And we had a moment go viral. And it was a photo of me and my husband on the beach in Hawaii. And I was talking about,

body image. And it was the funniest post because I just, I never expected it to go viral. I think that's what happens with viral posts. And I was clapping back at someone who had said, how can a woman like you get a man like him? And my husband is very fit. He's very in shape. At the time, I was curvier. I had been going through miscarriages and lost. My body had been through so much. And I was just angry. And I was like, who are you to say this? Like, we have been together for a decade. He has loved me through every pound, every pimple, like everything. And that post like blew up. And overnight, we got hundreds of thousands of followers. And blessing and a curse, right? Double-edged sword. Because, wow, this is amazing. But also, like, who are these people and why are they here?

Yeah. And what are they watching? That's when I first found out about you. Yes. Because I was starting to podcast and I was growing popularity in podcasts. And then I remember hearing about Jenna Coucher. And your likelihood was so tied up with like, body image. And so like you were the body image girl that was like spreading body positivity. And that's what you were known for. Was that hard to sort of like get out of that box? Because now you're out of that box. It was, well, it was so confusing because I had talked about body image for years. I think it's a lifelong journey to learn how to love yourself. And I don't think it ever ends. And so the fact that like one random post goes off and then here I am running a business,

teaching entrepreneurs and now all these people are following commenting about my body wanting more of that content that I'm not monetizing because I didn't want to monetize it. It was very confusing. And again, it was such a blessing and a curse because so many people resonated with the message and it connected with them and they felt seen and they felt understood. And at the same point, too, as a creator, it's like, what do I do with this? And as a business owner, where do we go from here? like, I'm not going to sell a course about body image. And so it was a really interesting time. And I think that I just did my best to like stay very true to myself, stay very grounded in the message to be clear of like, here's what you can expect if you stick around here because this isn't

going to become this type of account. And so yeah, it was very interesting. I want to dig into the course thing and how it lended itself so nicely to you doing affiliates. Yeah. Because something that a lot of entrepreneurs don't realize is that like once you figure out how to promote something well. You can then just take that and replicate it in a million different ways. Yes. And I was even talking about this yesterday. Me and Jenna were at the IAB upfrence. We were both like very integrated into this big podcasting event for advertisers. And I was telling the advertisers, yeah, media, my network, we're all business owners. And so we understand how to promote our own products and services. And then we turn that into podcast sponsorships. So that's what I've been doing.

you've been doing that with affiliate marketing. So I'd love for you to walk through, like, how do you actually promote your courses? And then how is that very, like, what is the relationship to that and then how you started affiliate marketing? Yeah. Oh, my gosh. I love affiliate marketing. I know.

I don't do any of them. Oh, my gosh, people. Okay. So we do seven figures in affiliate marketing each year over seven figures. So, like, if people are wondering, like, are you getting pennies to the dollar? Like, this can be a very lucrative thing, especially if you. if you don't have a ton of offers that you are selling on your own. Affiliate marketing is literally just recommending someone else's product

and getting a commission when people buy it. And so if you have gotten people's trust in what you are recommending with anything and they do trust you, they will follow you wherever you lead them to in a beautiful way, right? And so I love affiliate marketing, whether it is skincare, whether it is jeans, whether it is another online course. I just think it's so powerful. And the reason why I love it is because I am not an expert in everything. Very clearly, I'm not an expert in all the things. And I want to recommend things and

people that I love to the people that I love. And so I am a natural connector. My greatest joy in life is like connecting people that I love to each other, connecting people to products that they love. So one of the things that I've realized is like I can sell my own stuff. That's wonderful. But what does it look like when I partner up with brands that I love and with people that I love and help promote their business. We recently partnered with one of my dear friends who I've literally known for almost a decade and she's my copywriter and she is an amazing course. And I was like, Ashlyn, let me talk about your course. Like your work has changed my life and so many people could benefit from this. And I am not a pro copywriter. And it transformed her business. It changed her launch. It made her

show up differently. My audience was like there. We had thousands of people sign up for her masterclass. And so it's like so fun for me because I'm like, I get to support the people and brands that I love. I get a commission from what I'm selling. And I get to kind of experiment with different marketing strategies because there's less skin in the game and I get to be more creative of like, what does this look like? But go into the nitty gritty. Like what are you doing? I know you're using many chat automation. Like are you leveraging an email list? Just tell me like, what are you doing? Okay. You want me to give you the lay of land. Okay. So if somebody's listening to this you have a podcast, a very natural way to do this is to have a podcast interview and to be able

to tie it to some of the job. That's what we did when we did my LinkedIn course. Yes. And so just naturally integrating what that person is an expert in and inviting people with a call to action at the end of the podcast. If you have an email list, sending out emails about, hey, this person that I trust, this is my experience with them. This is how they've transformed things for me. This is why you should trust them or join their free masterclass. If you have Instagram, sharing about it on Instagram. So we've basically built this almost like flywheel where we could have a guest on our podcast. We could send out a couple of emails. I could do an Instagram live with them in a few Instagram posts. And that's honestly it. And they take care of the rest. And it's people that I trust

that are going to serve my audience well at the highest level. And then if it's the right offer for them, they'll take it. So now you've got like millions of followers. Take us back to when you didn't have millions of followers. It wasn't that long ago. How would you promote something then? Like if you're like maybe you've got a couple thousand followers, but you're really smart. You already make money doing something really well. Maybe you have a job and you do something really well.

Maybe you have a company. You do something well. But you just don't have a lot of followers. How would you then either sell courses or affiliate marketing? Yeah. So I would say two channels. So Pinterest is huge. And I love.

That's a juicy one. No one talks about this. Y'all, Pinterest is a search engine. It's not social media. And it's so crazy to me that people think that it is just like a place to like plan your dream life but not do anything about it. When people go on to Pinterest, they are typing in recipes with sausage or, you know, makeup looks for work or, you know, capsule wardrobes for vacation. Like people are typing in keywords. And they're typing in stuff that you have created or work that you

could create. And so we get millions of views on Pinterest a month just using like this. same strategies you would use for search engine optimization, just using keywords. That's so smart because nobody's doing that. Nobody's doing it. Especially for targeting women. Yes. And the cool thing about that is like with Pinterest being a search engine, it's not a popularity contest.

So unlike other social platforms, in order to get your work seen, you have to have a massive following because it is a search engine. If you are search engine oriented, you will be found. And so if you are someone listening to this and you're like, great for you, I don't have a million followers or I don't have this. Pinterest is an amazing place. So we use Pinterest to grow our email list. I look at marketing very distilled down.

There are two focuses. The first primary focus is growing your email list. Why it is an asset that you own. It is something you can control. Social media is amazing. It is rented space. You do not own it. You can't control it.

You are battling multiple algorithms. Your email list is a true asset. If you are somebody listening and you want to be in business, three years from now, five years from now, 10 years from now, you have to have an email list. That is the only way. So priority number one in marketing is an email is. Priority number two is any other platform that you are using, whether it is LinkedIn, YouTube, a podcast, Instagram, all of those efforts need to be getting people off of those platforms and onto your email list. That is it. And it's so funny because we overcomplicate marketing and we're like,

you know, Instagram doesn't work. How are you using Instagram? Are you serving or are you selling? If you are selling, no wonder it doesn't work. And so your primary focus as a creator is to start your email list and then any efforts that you have, the goal should be to get people off of whatever platform they're on and onto your list because, again, you own that. And you get them off of the platform by serving them and then retargeting them in the DMs to get them in your email list. One of the biggest regrets I have is not starting my email list until like just a couple

years ago I started it. And my favorite way, I don't know if you do this. to get emails is to do webinars. Yes. So I do these private Zoom webinars where I'll do like LinkedIn training, sales trainings. I'm doing like a mental health one for entrepreneurs later this summer. And then I'll get like a thousand, two thousand people registering. Boom.

I got 2,000 emails now. And they opted in so I can communicate with them now. And there's so much clicks and conversions that happen in email. Like it's a lot of sales are happening on email. So I love that. Young and Profiters. I know there's so many people. tuning in right now that end their workday wondering why certain tasks take forever, why they're

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monthly overhead and stay connected. Yeah, Pam, you should definitely take advantage of this offer. It's free business internet forever. Visit Spectrum.com slash free for life to learn how you can get business internet free forever. Restrictions apply. Services not available in all areas. Okay, so we talked about a number of your revenue streams already. We talked, talked about your watercoloring business when you first started out. We talked about courses. We talked a little bit about podcasts and your different sponsorships and affiliate marketing. What other revenue streams do you have? So one thing that we are super passionate about is real estate. And I love real estate.

I love property. I love looking at houses online. Like I just, there's something about making a space a home and sharing it even that just feels so powerful to me. And years and years ago, Drew and I used to spend multiple months of the year in Maui. And it was after I had had this revelation of like, I can build a business that can run while I rest. Like, what would it look like if we spent a month on Maui? And then it turned into two and three. And we started to fall in love. But we were also spending a lot of money staying there.

And we would stay in Airbnb's each time. And we started to like ask ourselves questions like, okay, we're spending a lot of money here. Like what would this look like? Like could there be a possible? that like we could do this ourselves. And I'll never forget a trip. My parents came to visit us and there was an open house. We were walking down the beach and we're like, I don't know, let's just pop in and look. And I started to really dream bigger. And at the time, my business was not at all the size that it is today. And I remember we went through this open house. I took the little flyer and I went and sat in a coffee shop and I started doing

math. And I started thinking about, okay, how much are we spending a month when we're here? How much rent could we potentially earn? What would the expenses be? What are the HOAs? What does this look like? And one thing that's super interesting about Hawaii is there's a lot of different zoning. So there's apartment zoned and there's hotel zoned. And the place that we were looking at used to be a hotel. It literally is zoned as a hotel. And I remember just thinking, this is so peculiar that this was an operating hotel and they have now created it into spaces that people could own. And I sat down in this coffee shop and started running the numbers and I'm like, I think we could make this work. And I remember telling Drew, I am committed to eating ramen noodles for a year if we do this because we just loved

being on the island and we loved having this space and the thought of like doing it was like just so exciting. And so we ended up putting in an offer. I will never forget. We flew back to the island. So we got this place and I've been owned by this sweet, sweet old couple for years. And we had one week to like flip the unit and get it ready for Airbnb. And I literally thought we were going to get divorced that week because we were like painting and getting the couch and the couch was too big. It couldn't fit through the door and all these like silly things that we were like, what did we get ourselves into? And it ended up being one of like the biggest blessings. We have hosted hundreds of couples over the years. We have had so many repeat guests come back to

space and we have been able to kind of just create a community with our guests, with the team that helps us like take care of our property. It's been so beautiful. We've also been able to give back so much to the community. Like we bought a place on the island because we care about the island. And so last year alone, we donated over 30% of our profits to locals and to support them. We were able to help people in need when the devastating fire went through Lahaina. we opened up our doors. We housed locals for over two months in our unit and we just took care of people. We used our network of other Airbnb hosts and we said like open your doors. We will pay all of your expenses. Just get people in. And so it was amazing to see like, yes, it is a property and yes,

it is this place where people can rent and stay, but we're also doing something a lot bigger with it. And that matters to me. Like anything that I do has to have meaning. And I care so. I care so deeply about like the why behind our work that like I want to make sure that there is always facets of like respect and community built into everything that we do. And so it's been beautiful. My parents were just down there and stayed and to be able to like see our space be shared and loved by people we love, but also taken care of by people we love and enjoyed by people we love. Like it just feels like this trifecta of like blessings upon blessings. And I just, I love property and I love the idea of like putting together a space where people are making lifelong

memories because when we went to Hawaii, it was like a bucket list trip. It was like someday in our lifetime, I want to go to Hawaii. And the fact that like now we get to host people on their bucket list trips, like how cool is that? I love that. I could see like the joy exuding from you. Like it makes you so happy to host these people in your home and make your home beautiful. So like how does it work because you're not physically in Hawaii? Do you have some somebody managing the property. You obviously need to get it cleaned and if somebody needs something, like, how does that all work? Yeah. So we've had the same team of people since we first started. And we met them at church in Hawaii. And we have a property manager and we have a cleaner.

And they are like dear friends to us. And our cleaner is a single mom of three boys. And like, we work with her. So we share our calendar with her. She knows when people are checking in, checking out. She lets us know like, hey, guys, can you order a new rug for this? Or can you get some new sheets or we need, you know, a new laundry basket. And she kind of keeps the eyes on our property. And then on island, we have a representative so that, let's say somebody got locked out or they needed help immediately. Obviously, we're in Minnesota. We can't do that. And so it's actually not that complicated. And what's beautiful is it provides for the local economy. Like, we're creating jobs for the local economy. We have a handyman that we've employed for years.

So like, it's this beautiful web of how you can create opportunity. for other people if you personally or physically cannot manage it yourself. And a lot of companies excel at helping manage it. So like while we still do all of the touch points with whoever is staying with us, then we have this like second line of defense to help make sure that like everything is safe. Everything is protected. Everything is clean. And it's, you know, honestly, it's not as stressful as it sounds. Yeah. I love the fact that as you're talking about this and I didn't expect to get this out of you is that it's about like building community. It's like you're building a community with the people that are coming in staying at your Airbnb, the people that are working for you. And even the relationship and the bond that you're deepening with your husband. And something that people don't realize is that you don't necessarily need an investment property to do this. You could do this in your own home now. You can host a room in your house.

Yeah, that is something that is coming up a lot lately. And it's an amazing way for people to supplement their mortgages or to, help pay their rent. And we and Drew and I experienced this years ago, and I feel like these people were ahead of the curve on this. But we went on an anniversary trip, and we were driving along the coast of California. And we rented a room in this like bed and breakfast type house, but they owned a farm. And I was like, I want to see the alpaca. I want to check out the goats. I want to collect the eggs from the chickens. And it was a whole different life than what we were living. And I remember we showed up and they greeted us at the door and they had a bottle of wine chilled. And they had like

sharkoery boards out and like we sat and talked to them. We got to know about like their life of living on this farm and why they were doing it. And it was such a cool experience where it opened my eyes up of like, yeah, it doesn't have to be a whole house. You don't have to buy a condo. Like you can literally do this wherever you are and start to share your space in such a meaningful way. Love that. So something else that's really popular now is working remotely. So many people can work from anywhere now. And so I imagine that if, you know, you explore it and it's possible, you can just put your apartment or house on Airbnb and then go work remotely to someplace that you've never been. It's such like a win-win solution because it would offset any costs of you going and working from somewhere else. Yeah. Remember I see the movie,

the holiday? Did you ever see that movie? No. Oh my gosh. They like house swap. So like one person goes to L.A. and one person goes... I can't have seen this. And they like trade houses. And I'm like, that is so genius because it is true like a lot of people these days have a lot more freedom and flexibility to work wherever i know um during the pandemic we moved up to our lake house in minnesota and our neighbors there have spaces that they rent on Airbnb and during the pandemic we would go on walks with them every day and they had this huge dream of like living in hawai that's where they had met initially they wanted to live in hawai they were able to rent out their spaces in minnesota and now they live in hawaii and it's like crazy because I'm like, you just see that there's so much possibility there and a little bit of

creativity, which I think entrepreneurs naturally have. And so it's like maybe this is something that you haven't even been considered, but like what would it look like if you explored it? So I am curious about starting an Airbnb. And one of my fantasies is I'm not married yet. I was in a long-term relationship. And I was like begging him to do Airbnb with me to host an every and be because to me I feel like it's such a fun project to do with a partner. Like it just seems like the perfect business project to work on with somebody that you love because it's relatively easy. It's an investment that both of you guys will like be a part of. There's like enough things for both people to do. And to me it just seems like such an awesome

thing to do with your partner. So can you talk to us about doing this with your husband and what that is like? Yeah. So I got a shout out my husband, Drew, because he does most of our work with the Airbnb's and he loves it like he is our real estate professional in our family he really enjoys it um and so he does the majority of it and it is so fun because like i love i love the decor i love the messages i love like making sure our guests feel cared for i love the recommendations like all things we've talked about in this episode and he is very good at like the financial side and the organization and managing our cleaner and just like different things like that where he has more of like the boots on the ground mentality and I'm more of like, here's the experience. I'm going to

paint this picture. And so it is so fun. And we always want to pick places that we love and enjoy ourselves. And so it's like, we love this and you will love this too, which is a theme. Have you noticed? I love telling people about business. I love telling people about the products. I love, I love just sharing experiences with people. And so it was such a natural progression. And for us to do it together, it was our first big investment as a couple. Like we really had to have conversations. of like, can we do this? Well, we do this. What does this look like? And it felt like a huge leap of faith. And it's just been one that has been this, like, beautiful journey for the both of us. And I feel like it connects you guys closer because you guys are in business together. You're making

money together. I just feel like that's such an awesome thing to do with your partner. So I love that you do that. So something else to know about Jenna is that she only does stuff that brings her joy. You only do things that you want to do. I bring Jenna opportunities all the time. She's in my podcast network where I'll be giving her, like, I booked sponsorships for her. And she'll be like, I don't want to do that. I'm burnt out. I'm burnt out on IG Rails. And I'm like, but it's thousands of dollars. Are you sure? And she's like, yeah, I don't care. I'm burnt out. I'm not doing that. You can do it. You can book it in two months or whatever. So talk to me about that. Like, how are you able to sort of just put your foot down? A lot of people couldn't just turn down

money like that. Yeah. I mean, first off, it is such a privilege to be in a position. Yeah, it wasn't always like that. Oh, you've got a sacrifice. But I've realized, and here's what I've really realized, is if you have listened to this whole episode, you recognize the power of trust. And I want my community to trust me. And if something isn't in alignment, not only do I feel it, but they feel it. And so I have had to get so good at discerning what are the right partners, what are the right

opportunities, what are the right like sponsorships to take on? Like, is this in alignment? And I feel that way with every opportunity, whether it is getting asked to speak on. stages that I would have once dreamt of being on, but now I'm saying no to or whether it is, you know, hosting a mastermind or all these things. I could do a million things. I don't want to. And I think that I'm just at this place in my life where I just recognize that like peace is needs to be protected. And right now in this stage of my life, like my priority is my family. And anything that I'm saying yes to is a no to them and what is the most important thing to me. And so, you know,

turning down things like recording another social media reel. To me, it's like, but this is more time with my kids or this is protecting and preserving the integrity of my followers. She'll even turn down things that are a good fit. Totally. Totally. She'll turn down things that are a great fit for her because she's like, no, my time with my family is more important.

Yeah. And I think that like boundaries protect what's sacred to you. And I've just had to relearn this lesson over and over and over again of like, boundaries aren't bad and boundaries like keep what I say most important to me and they they exemplify that like what I am saying is most important to me is reflected in my calendar it is reflected in my bank account is reflected in the way I show up every single day and so it's it's a muscle that you have to learn to flex and it takes time because I think that you know there was a time in my life where I got paid $50 to take pictures of a cat and I couldn't believe it like somebody

is paying me to do something I love this is amazing and what a black thing that is. And the better that you get out listening to your gut and discerning like, well, this is a great opportunity, but is it the right opportunity for me? It keeps you in alignment so that you are not passing up things that you should be saying yes to and that you are not saying yes to things that you should be saying no to. And so I feel like I just have like a really strong intuition and a gut game. And I don't apologize for saying no any longer because my no is literally just a reflection of like what is mattering the most to me right now. Yeah, but let's stick on this mindset because yesterday I was talking to Jenna I had when working on this crazy presentation for like

three months and I was like guys I killed myself on this I I worked so hard and we were with our other friend Amy Porterfield and she was saying you know I'm the same way like I work really hard sometimes and burn myself out and Jenna was like I don't know how you guys do that like I would never do that I would never choose to kill myself on anything and I always always always always lot of the times take the hard route. I don't know why. It's my personality. Why are you like this? Like, how did this come about? Were you always like this? Where you're just like, no, I'd rather just have my joy than the money. I feel like I've realized that like our piece is so expensive and life is so short. And I definitely am not anti-hustle culture because I do believe hustle is required

to get the dream off the ground, no matter what the dream is. There have been so many points in my career where I get an idea or have a project or something like yeah, I can hustle. But if hustle is the only way that you can operate and sustain what you're building, that is not a business. Like, you are building a prison for yourself. And I've watched so many people who have really successful businesses and really lousy lives. Like they are rich in their bank accounts and empty in relationships. And like to me, that's just not worth it. That is such a high cost. And I feel like I have had to learn how to discern like what are my best yeses and like what can I say no to without having phomo without having guilt and it's interesting because I think becoming a mom really shifted that for me of like

anytime I'm away from my kids I want it to be worth it and the only way for me to alleviate mom guilt was to know that like I was doing work that I love work that I enjoy work that gives me peace that excites me so that whenever I'm working, I'm not there thinking, I should be with my kids. And whenever I'm with my kids, I'm thinking I should be working. It's like the only way to get past that was to just be in total alignment of like, what do I want for my life? And I think we focus so much on like leaving a legacy. But I think in reality, we have to focus on living a legacy. And I'm like, I want my kids to see the joy. I want them to see the peace. And, you know, I've had so many turning points in my business where like, I've just,

realize that like money isn't the answer like at times in my business where I've earned the most money I've been the most miserable and I just feel like there's this threshold of like where do I get more joy how do I derive joy like what does peace look like like when I go to bed at the end of the night how do I truly rest and it's just been a huge shift and it's not easy and it doesn't come naturally because I am an achiever and I am a hard worker and I am driven but I'm just just had a place in my life where I'm like, I just want to enjoy it. Yeah. I love the way that you and your team handle it. You guys take Fridays off. Yeah. So they don't work on Fridays, but you're still crushing it and getting so much done. Like, you don't have to overwork yourself to be successful. And you were

such a great example of that. Yeah. There's this quote that I heard that totally changed my, my mentality. And it was instead of asking yourself, if you've worked hard enough to earn your rest, ask yourself if you've rested well enough to do your best, work. It was by a girl, Nicola Hobbs, I think is her name, or Nicola Dobbs. And I heard that and I was like, whoa, like, I have been wired of like, I just need to get this done and then I can rest. And I was like, what if we like flip this on its head? And it's just been so transformative for me because I'm like, no, I need to like come into this feeling rested and well to do my best work. And that is like totally shifted things. I love that. So this has been such an awesome conversation about all

the different ways that you generate revenue. We talked about courses, affiliate marketing. We talked about courses, affiliate marketing. We talked about you hosting a property on Airbnb and also about your mindset. I love learning about that because I need to have some more boundaries. So thank you for sharing that and thank you for joining us on Young and Profiting Podcast. Thanks for having me. Yeah, Bam, I absolutely loved having Jenna on the show. And honestly, this conversation holds a special place in my heart because this was one of the first times that I met Jenna in person. And I swear, even though it was one of the first times I met her in person, I feel like I've known her forever. Jenna is somebody that I've looked up to for years. I've listened to her podcast for years and

she's just so genuinely bubbly, so warm, so real. And what you see with her is exactly what you get. And it's so obvious why she's become such a powerhouse. She's literally the OG female podcaster. I've been admiring her work since I first started this crazy podcasting journey. And when I first started my podcast seven years ago, I wanted to be just like Jenna. What blows my mind is that now Jenna is in my podcast network, the Yap Media Podcast Network. I am exclusively responsible to get all of her sponsorships. So we're essentially business partners. And I get to call her my friend and mentor. So what a full circle moment. Now, this Yap Live episode was recorded in person in an Airbnb and the vibes of being in person is just so much different. And so it's really relaxed and authentic. And I'm just

so excited to do more in person interviews like this. And Jenna absolutely delivered in this conversation. and she didn't hold back anything when it comes to breaking down her multiple revenue streams. We dove deep into affiliate marketing, podcast sponsorships, course creation, and something I cannot stress enough. Building your email list. If you haven't started with your email list yet, please, please make it a business priority. I'm literally kicking myself for not starting it years sooner. We've had our email list for three years now, and it's been amazing for driving ROI, for driving subscribers and listens and webinar attendees. We use it for all of our initiatives.

And it's like having a security blanket for your business because here's the harsh truth. You can spend all this time creating content on Instagram, YouTube, TikTok, but you don't own that audience. You've got to pull those people into your email list where you have control. And by the way, email is like a social media algorithm that you have control over. You have a number of subscribers and you get to hit them directly in the inbox. If you guys have been listening to the show, you know all about interest-based algorithms. And on social media, it's really about your topic and the algorithm controls who gets to see your content. With email, you control who gets to see your content, and that is so important moving forward

in this creator entrepreneurship space. Another hidden gem from our conversation was Pinterest. We do not talk about Pinterest enough. It is still absolutely a massive platform, especially amongst women. And here's the kicker. It functions like a search engine. If you're serious about SEO and want to be discovered organically, Pinterest should definitely be a part of your strategy.

But honestly, the part that got me the most excited was when we were talking about real estate in Airbnb investing. You can literally see Jenna's entire face light up when she starts sharing about her hosting experiences. The pure joy she gets from creating these amazing spaces for people and getting the feedback from guests. It was so infectious, so much so that she inspired me to start my own Airbnb journey

and I've started to host out my apartment in Jersey City. And who knows, maybe I'll be starting my own Airbnb empire like Jenna. I've been thinking about investing in some more real estate. And of course, you guys will hear all about it since Airbnb. is one of my long-term sponsors. Thank you so much from the bottom of my heart for tuning into this Yap Live episode. It means absolutely everything that you chose to spend your time with me and Jenna.

If you watched us on video, Spotify video, or YouTube, I hope you sincerely enjoyed it and drop us some comments and leave some engagement so we can get more people checking out this awesome video. Nothing means more than growing this community by word of mouth. And if this conversation sparks something in you, I would love a five-star review on Apple, Spotify, CastBox, Wherever you listen to the show, I love reading your reviews that keep us going here at Yap.

And I'm so excited to tell you that now all of our live and in-person videos will be on Spotify video. We're going to release one a week. I've been doing so much in-person content. We've got enough for one a week for the next six months or more. And I'll be doing more and more. You can, of course, always watch our videos on demand on YouTube. We've got close to 60,000 followers on there.

And if you guys want to connect with me on Instagram, holla at me there at Yaff with Hala. You can also follow me on LinkedIn. Just search for my name. It's Hala Taha. And before we go, I want to shout out my Yap Bookings team, Hisham for Khan and Joshua. You guys do such an incredible job. You are the secret sauce behind the show, helping me secure guests like Gary V, Jenna Coocher, Damon John, Matthew McConaughey. We are incredible at booking guests. And now we actually offer this as a service for other people. So if you're interested in that, go to yapmedia.com to learn more. Well, that's all the time we have for today. Thank you so much for tuning into this Yap Live episode.

I hope you guys are enjoying this Yap Live series. This is your host, Halitaha, aka the podcast Princess, signing off.