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Hala Taha
Today's episode is sponsored in part by indeed, Shopify, Mercury, Open Phone, Airbnb and Boulevard. As always, you can find all of our incredible deals linked in the show notes or@youngandprofiting.com deals.
Jenna Kutcher
We focus so much on, like, leaving a legacy, but I think in reality, we have to focus on living a legacy. Jenna Kutcher. Jenna Kutcher.
Hala Taha
Jenna Kutcher. She's the host of the Gold Digger podcast. She's a best selling author and she's also an entrepreneur of many different businesses. You've got like a million plus followers on Instagram. You're huge, huge on Pinterest. How did that piece come about?
Jenna Kutcher
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 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.
Hala Taha
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, we actually talked about Airbnb in this episode. Today I'm interviewing Jenna Kutcher. She's the host of the Gold Digger podcast. She's a best selling 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 Kutcher. Jenna, welcome to Young and Profiting Podcast.
Jenna Kutcher
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?
Hala Taha
Yes.
Jenna Kutcher
Let's do it.
Hala Taha
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?
Jenna Kutcher
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 5, 10, 15, 20 years. Like, there's gotta 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 experience 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 is 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 in? Yeah. Okay. So my first side hustle was I became a watercolor Artist.
Hala Taha
Oh.
Jenna Kutcher
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?
Hala Taha
Amazing.
Jenna Kutcher
I ended up figuring out a way to scan these watercolor art prints and sell them online. And pretty soon we were paying our mortgage with the print revenue.
Hala Taha
Your first sort of passive income revenue stream.
Jenna Kutcher
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 onto 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 0 to 100k in 3 years. I knew 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.
Hala Taha
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?
Jenna Kutcher
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. Yeah, 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 week? 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 apart a car and figure out how to put it back together. I can't do that. But when it comes to digital stuff, I am 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.
Hala Taha
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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 masterclass 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?
Jenna Kutcher
No, I mean, it. 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 filter, I would just share my life, like, and 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 a wedding photographer, I just hid behind my work. It was like this 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'd 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. I 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 figured 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 girls date with my girlfriends, by the end of the day, I've dropped like 10 lips. 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 loss. 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 and what are they watching for?
Hala Taha
That's when I first found out about you because I was starting to podcast and I was growing popularity in podcasts. And then I remember hearing about Jenna Kutcher and your likeliness 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.
Jenna Kutcher
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 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.
Hala Taha
I Want to dig into the course thing and how it lended itself so nicely to you doing affiliates.
Jenna Kutcher
Yeah.
Hala Taha
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.
Jenna Kutcher
Yes.
Hala Taha
And I was even talking about this yesterday. Me and Jenna were at the IAB upfronts. 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 sponsorship. 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?
Jenna Kutcher
Yeah. Oh, my gosh. I love affiliate marketing.
Hala Taha
I know. I don't do any of that.
Jenna Kutcher
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 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. Like, 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.
Hala Taha
Yeah.
Jenna Kutcher
And so it is like, 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 has 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. 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?
Hala Taha
But go into the nitty gritty. Like, what are you doing? I know you're using manychat automation. Like, what you doing? Are. Are you leveraging an email list? Just tell me, what are you doing?
Jenna Kutcher
Okay, you want me to give you the lay of land? Okay, so if somebody's listening to this and 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 something.
Hala Taha
That's what we did when we did my LinkedIn course.
Jenna Kutcher
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 emails. I could do an Instagram live with them and 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. If it's the right offer for them, they'll take it.
Hala Taha
So now you've got, like, millions of followers. Take us back to when you didn't have millions of followers.
Jenna Kutcher
It wasn't that long ago.
Hala Taha
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 do something well, but you just don't have a lot of followers. How would you then either sell courses or affiliate marketing?
Jenna Kutcher
Yeah, so I would say two channels. So Pinterest is huge. And I love.
Hala Taha
That's a juicy one. No one talks about this, y'.
Jenna Kutcher
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 onto 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 are 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, the same strategies you would use for search engine optimization. Just using keywords.
Hala Taha
That's so smart, because nobody's doing that. It's basically a search engine, especially if we're targeting women.
Jenna Kutcher
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, like, we use Pinterest to grow our email list 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 list. 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, 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 them and you.
Hala Taha
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. 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.
Jenna Kutcher
Yes.
Hala Taha
And conversions that happen in email. Like it's a lot of sales are happening on email. So I love that. When I first started Young and profiting podcast back in 2018, it was just a hobby. And for two good years I poured more time and money than I got back. At times I kept asking myself is this worth it? What if it never works? What if I don't have the tools, the time or the team? But I just pushed through and I was consistent and now it's one of the top entrepreneurship podcasts in the world. I almost let those what ifs stop me from building something incredible. If you're sitting on a business idea, it's time to stop overthinking and start doing with Shopify. Shopify powers millions of businesses worldwide and 10% of all US E commerce. From giants like Gymshark and Mattel to startups just getting started, no team, no problem. Shopify handles everything from web design to inventory to customer service and shipping all in one place. If you're on a tight budget, their built in marketing and email tools help you find and keep customers selling in person. Is also seamless with Shopify's award winning Point of Sale which connects your online and offline sales. Want to go global? Shopify supports sales in over 150 countries with tools for translation, international shipping and local currencies. And with 99.99% uptime and the best converting checkout on the planet, it you'll never miss a sale. Turn those what ifs into and keep giving those big dreams the best shot with Shopify. Sign up for your $1 per month trial and start selling today@shopify.com profiting. That's all lowercase. Go to shopify.com profiting again, it's shopify.com profiting. My business partner, Kate and I traveled to London for a podcast conference and we stayed at the most gorgeous Airbnb. It was a top floor flat with a private terrace and views for days. And after those long conference days, we'd sit outside, decompress, chat and watch the sunset over the city. Having our own bedrooms and bathrooms made those early morning prep sessions so much easier too. Trips like that are a big part of my lifestyle. And between all the traveling, I see so many incredible spaces sitting unused. The good news is that even if you're not there to enjoy your home, somebody else can. Because hosting with Airbnb just makes sense. And if you don't have time to manage it yourself, that's where the co host network comes in. A co host is a local partner that you can trust to handle day to day, like guest messaging, restocking, and keeping the space guests ready. It's perfect if you love the idea of hosting but are too busy to manage all the little details. You don't have to be hands on to be a great host. Find yourself a co host@airbnb.com host. Okay, so we talked about a number of your revenue streams already. We 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?
Jenna Kutcher
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 Airbnbs 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 possibility 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. 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. It had 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 in, 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's 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 our 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. Like, 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 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 now we get to host people on their bucket list trips, how cool is that?
Hala Taha
I love that. I could see the joy exuding from you. It makes you so happy to host these people in your home and make your home beautiful. So how does it work? Because you're not physically in Hawaii. Do you have somebody managing the property? You obviously need to get it cleaned. And if somebody needs something, how does that all work?
Jenna Kutcher
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 a new laundry basket? And she kind of keeps. 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 are 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 opportunities 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.
Hala Taha
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.
Jenna Kutcher
Yeah, that is something that is coming up a lot lately, and it's an amazing way for people to, like, supplement their mortgages or to help 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, like, showed up and they greeted us at the door, and they had a bottle of wine chilled, and they had, like, charcuterie 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.
Hala Taha
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. 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.
Jenna Kutcher
Yeah. Reminds me of the movie the. The Holiday. Did you ever see that movie?
Hala Taha
No.
Jenna Kutcher
Oh, my gosh. They like house swap. So, like, one person goes to LA.
Hala Taha
And one person, I've seen this, and.
Jenna Kutcher
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. 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 Hawaii. That's where they had met. Initially they wanted to live in Hawaii. They were able to rent out their spaces in Minnesota, and now they live in Hawaii.
Hala Taha
Amazing.
Jenna Kutcher
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 considered, but, like, what would it look like if you explored it?
Hala Taha
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 Airbnb, because to me, I feel like it's such a fun process 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. What that is like?
Jenna Kutcher
Yeah. So I gotta shout out my husband, Drew, because he does does most of our work with the Airbnbs and he loves it. Like, he is our real estate professional in our family. He really enjoys it. 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? Will 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.
Hala Taha
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 reels. 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 could 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.
Jenna Kutcher
Yeah. I mean, first off, it is such a privilege to be in a position.
Hala Taha
Yeah. It wasn't always like that.
Jenna Kutcher
No.
Hala Taha
You've got to sacrifice.
Jenna Kutcher
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 sponsorships to take on? 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 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 point, 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, 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 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.
Hala Taha
She'll even turn down things that are a good fit.
Jenna Kutcher
Totally, totally.
Hala Taha
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.
Jenna Kutcher
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 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 blessing 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.
Hala Taha
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 worked so hard. And we were with our other friend, Amy Porterfield, and she was saying, I'm the same way. I work really hard sometimes and burn myself out. And Jenna was like, I don't know how you guys do that. I would never do that. I would never choose to kill myself on anything. And I always, a 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.
Jenna Kutcher
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 fomo, 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 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. 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 realized that, like, money isn't the answer. Like. 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 at a place in my life where I'm like, I just want to enjoy it.
Hala Taha
Yeah. I love the way that you and your team handle it. You guys take Fridays off.
Jenna Kutcher
Yeah.
Hala Taha
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 are such a great example of that.
Jenna Kutcher
Yeah. There's this quote that I heard that totally changed 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, I have been wired of. I just need to get this done and then I can rest. And I was like, what if we flip this on its head? And it's just been so transformative for me because I'm like, no, I need to come into this feeling rested and well to do my best work. And that has totally shifted things.
Hala Taha
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 you hosting a property on Airbnb, and also about your mindset. I loved 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.
Jenna Kutcher
Thanks for having me.
Hala Taha
Yeah. Bam. I absolutely loved having Jenna on the show. And honestly, this. 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 podcasts 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 podcast 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 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. 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.
Jenna Kutcher
If you have.
Hala Taha
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 a year 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 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 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 and 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 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 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 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 yaffwithhala. 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 gas guests like Gary Vee, Jenna Kutcher, 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 yap media.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, Hala Taha, AKA the Podcast Princess, signing off.
Podcast Summary: Young and Profiting with Hala Taha featuring Jenna Kutcher
Episode Title: Jenna Kutcher: Turn Your Side Hustle into a 7-Figure Online Business | Entrepreneurship | YAP Live
Host: Hala Taha
Release Date: July 11, 2025
In this insightful episode of Young and Profiting with Hala Taha, host Hala Taha welcomes Jenna Kutcher, a multifaceted entrepreneur renowned for her Gold Digger podcast, bestselling authorship, and expansive online presence. With over a million followers on Instagram and a significant following on Pinterest, Jenna shares her journey from corporate America to becoming a powerhouse in entrepreneurship, sales, and marketing.
Jenna recounts her pivotal decision to leave a comfortable corporate job at the age of 23 to pursue her passion for wedding photography. Armed with a $300 camera from Craigslist, she taught herself the craft and rapidly scaled her business to six figures within three years. Despite this success, Jenna experienced burnout and sought a more sustainable business model.
Jenna Kutcher [02:28]:
"When I was growing my business, I was also experiencing burnout. I can't imagine doing this for the next 5, 10, 15, 20 years. There has to be a different way."
Inspired by a statistic that the average millionaire has seven revenue streams, Jenna embarked on diversifying her income. She highlights the importance of discerning profitable opportunities and setting boundaries to prevent burnout.
Jenna Kutcher [01:26]:
"I have had to learn how to discern, like, what are my best yeses and like, what can I say no without having FOMO, without having guilt."
Jenna’s first side hustle involved becoming a watercolor artist. Utilizing her mother-in-law's art supplies, she began selling her watercolor prints online, which quickly became a passive income stream covering her mortgage.
Jenna Kutcher [05:10]:
"I ended up figuring out a way to scan these watercolor art prints and sell them online. Pretty soon we were paying our mortgage with the print revenue."
This experience taught her the value of creating scalable products that generate income without continuous time investment.
Transitioning from one-on-one coaching to creating online courses was a natural progression for Jenna. By reverse engineering successful courses and leveraging her hands-on experience, she developed comprehensive programs that catered to the common challenges faced by photographers and other entrepreneurs.
Jenna Kutcher [07:03]:
"My secret sauce is like reverse engineering... online courses cracked my life open in such a beautiful way."
Jenna emphasizes the importance of identifying trends and common questions among her clients to create valuable course content.
Jenna discusses her organic growth on social media platforms, particularly Instagram and Pinterest. A pivotal moment was a viral post addressing body image, which significantly increased her follower count and solidified her role as a trusted influencer.
Jenna Kutcher [15:41]:
"I realized people need to connect with people. When I started to identify these trends, I was like, oh, my gosh, I can teach branding and I can teach social media..."
This authenticity in sharing her personal struggles and successes resonated deeply with her audience, fostering a loyal community.
A significant portion of Jenna’s revenue comes from affiliate marketing. She explains how recommending products she genuinely loves not only supports her audience but also creates a substantial income stream.
Jenna Kutcher [22:17]:
"We do seven figures in affiliate marketing each year. Affiliate marketing is literally just recommending someone else's product and getting a commission when people buy it."
Jenna highlights the importance of trust and alignment with brands, ensuring that her recommendations genuinely benefit her audience.
Jenna and Hala underscore the critical role of an email list in sustaining and scaling a business. Unlike social media platforms, an email list is a proprietary asset that offers direct communication with an engaged audience.
Jenna Kutcher [25:11]:
"Growing your email list is the primary focus in marketing. It is an asset that you own. Social media is rented space."
They discuss strategies such as using Pinterest for SEO-driven traffic and leveraging webinars to capture email subscribers, ensuring long-term business resilience.
Jenna delves into her passion for real estate and Airbnb hosting. By investing in properties zoned for short-term rentals, she has created a sustainable income source while fostering community and giving back, especially during crises like the Lahaina fire.
Jenna Kutcher [31:15]:
"We have hosted hundreds of couples over the years. When the devastating fire went through Lahaina, we housed locals for over two months in our unit."
Jenna emphasizes the joy and fulfillment derived from creating memorable experiences for guests and contributing positively to local communities.
A recurring theme in Jenna’s journey is the balance between hustle and personal well-being. She advocates for setting boundaries, saying no to non-aligned opportunities, and prioritizing peace and family over relentless work.
Jenna Kutcher [43:50]:
"Boundaries protect what's sacred to you... My no is literally just a reflection of what is mattering the most to me right now."
Jenna shares how motherhood has shifted her perspective, making her prioritize work that brings joy and aligns with her life’s values over sheer monetary gains.
Hala Taha reflects on the enriching conversation, highlighting the diverse revenue streams Jenna has built—from courses and affiliate marketing to real estate and Airbnb hosting. She underscores the importance of building an email list and leveraging platforms like Pinterest for organic growth. Inspired by Jenna’s approach, Hala has begun her own Airbnb journey, demonstrating the tangible impact of the episode's insights.
Hala Taha [50:34]:
"If you haven't started with your email list yet, please, please make it a business priority."
The episode serves as a comprehensive guide for entrepreneurs seeking to diversify their income, build scalable businesses, and maintain a healthy work-life balance.
Key Takeaways:
This episode of Young and Profiting with Hala Taha offers a treasure trove of actionable advice and inspiring insights from Jenna Kutcher’s entrepreneurial journey. Whether you're launching a startup, scaling a business, or seeking to enhance your sales and marketing skills, Jenna’s experiences provide valuable lessons on building a profitable and fulfilling business.