TW : fertility, miscarriage, pregnancy loss
“I will never forget sitting down with my boss, and she said, congratulations, we’ve planned out the next five years of your life. And I remember in that moment having this visceral reaction of, they didn’t even ask me what I want for my life. They didn’t ask me.”
In this candid conversation, guest Jenna Kutcher, entrepreneur and host of the renowned Goal Digger Podcast, recounts the realization that prompted her transition from corporate America to the uncharted waters of entrepreneurship. Admitting to wanting more than just a job, she shares that it was a leap of faith, guided by a deep-seated desire to align her work with her passions.
“I wanted to create something meaningful, something that resonated with my soul.”
And the work she was doing, wasn’t it. It was then that Jenna recognized that her values and the values of the company she worked for weren’t the same — she wasn’t impressed by the career trajectory presented before her because she knew it ultimately meant giving them more and more of her time…time away from what she felt mattered in her life.
Despite the uncertainty and challenges that accompanied her decision to go into business for herself, Jenna remained steadfast in her commitment to authenticity and personal growth. Through her candid reflections, she highlights the importance of embracing discomfort as a catalyst for change and trusting the journey toward entrepreneurship. Jenna’s story serves as an inspiration for listeners to pursue their dreams courageously, even in the face of uncertainty, and to embrace discomfort as a necessary step toward realizing their fullest potential.
Hustle culture
Jenna reflects on her early entrepreneur days, sharing that she worked nonstop to the point of near burnout to replace her income from her 9-5. So much so that even though her business had raked in 6-figures, she considered scaling back down to when she was making $55k strictly for her sanity. It wasn’t until she made the very deliberate decision to pivot (yet again) that she was able to get her time freedom back and begin making more money than she ever had before.
Jenna decries the typical business messaging of “hustle harder, wake up earlier, do more,” while admitting that there is a season for hustling — but the season has to end at some point. “I do think that hustle is required to get a lot of businesses off the ground. But if hustle is the only state that your business can profit in and the only state that you can work in, then it’s not a sustainable thing.”
Embracing discomfort
Jenna and Tori talk about the power of discomfort, framing it as a necessary step toward personal and professional growth. Jenna’s statement, “Discomfort is the currency of your dreams,” serves as a rallying cry for listeners to embrace the discomfort that accompanies pursuing their passions. Tori adds to this concept by highlighting the correlation between discomfort and progress, emphasizing that every major decision in life involves stepping into the unknown.
Along with embracing discomfort, Jenna shares insights and a refreshing perspective on success, encouraging listeners to loosen their grip on control to invite ease into their lives. Her thought-provoking question, “What if it could be easy?” challenges the pervasive belief that success must be hard-won. Tori expands on this notion by underscoring the importance of simplifying complexities and trusting the process.
Navigating ADHD as an entrepreneur
Jenna’s candid exploration of navigating ADHD as an entrepreneur sheds light on the intersection of neurodiversity and business ownership. She shares a personal story of how she learned she had ADHD through a listener of her podcast. Acknowledging both the challenges and strengths associated with ADHD, her perspective reframes it as a unique gift rather than a hindrance, emphasizing the importance of self-awareness and leveraging individual strengths. What this looks like for her in business, is asking her team to only bring problems to her with potential solutions, rather than just asking her open-ended questions.
The power of podcasting
Both Jenna and Tori reflect on the transformative impact of podcasting, not only as a medium for driving business revenue but also as a platform for meaningful connection and community-building. Jenna’s passion for podcasting as a tool for amplifying voices and extending opportunities resonates deeply with Tori’s own experiences with the Financial Feminist podcast.
In reflecting on her massive success with podcasting, and the power of putting yourself out there even when afraid, Jenna shares, “Nobody wins when we play small…I love welcoming the evolution of who I am and who I’m becoming. I feel like when we do that, we usher other people in to say, it’s okay to change your mind. It’s okay to learn and grow. It’s okay to evolve as a human. It’s okay to try something new. It’s okay to be a beginner. And I think that that is the most beautiful gift you can give other people.”
Making the most of viral moments
Jenna’s viral post about body image and relationships serves as a poignant example of navigating sudden attention and media features with grace and authenticity. Her advice to “stay true to yourself, reintroduce yourself to new audiences, and embrace the journey” encapsulates the resilience and authenticity that define her approach. Tori echoes this sentiment, emphasizing the importance of remaining grounded amidst sudden fame and leveraging viral moments as opportunities for deeper connection and impact.
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Meet Jenna
Jenna Kutcher guides millions of listeners each week in chasing their dreams on the #1 Marketing podcast in the country, The Goal Digger. A born-and-raised Minnesota wife, mother, and entrepreneur, Jenna has helped women all over the world redefine success and wake up to their lives through her decade-long work as a leading online educator.
Transcript:
Tori Dunlap:
Hi team. Just a quick sugar warning before we get into this episode. There is discussion around pregnancy and fertility and miscarriage and just want you to be aware. If that’s something that’s going to be tough for you to hear right now, no worries. We can either see you back here when you’re ready or skip this episode and we’ll see you back here next week. Thanks.
Jenna Kutcher:
We are obsessed with befores and afters in this society, but you are way better positioned to help somebody that’s just a few steps behind you, right? We want to wait until we’re fully removed from the situation, we have all the answers, when in reality I would much rather learn from someone that is on the same journey. That is just a little bit ahead of me, that’s just figured out a few extra things.
Tori Dunlap:
Hi, team and welcome to Financial Feminist. I’m so excited you’re here. Thank you for being here. As always, if you’re an oldie buddy goodie, welcome back, if you’re new to the show, hi. My name is Tori. I talk about how money affects women differently and also how we can fight the patriarchy by getting rich. I’m a New York Times bestselling author of a book also called Financial Feminist. I am also a multimillionaire, a general money expert, giving you resources about how to save money, pay off debt, start investing, build a business, negotiate your salary, and a whole bunch of other things. So we’re just excited you’re here.
Today on the show, this is a long awaited, many times requested guest. She is such a business icon, but also someone who has become a friend to me. And I tell her this in the episode, but she was one of the first people I ever followed and thought to myself, maybe I could run a business like her someday. And now she’s a fucking colleague, which is just so cool. Jenna Kutcher guides millions of listeners each week and chasing their dreams on the number one marketing podcast in the country, Gold Digger, which also I’ve been lucky enough to appear on. A born and raised Minnesota wife, mother, and entrepreneur, Jenna has helped women all over the world redefine success and wake up to their lives through her decade long work as a leading online educator.
A couple of things we’re going to talk about today, the two types of entrepreneurs. I have this theory that people who are wanting to go full-time with their entrepreneurship or wanting to take the leap have to either be this or that, and we’ll talk more about that. Why it’s so important to understand that time might be your most valuable currency you have? The balance between hustle and rest as a business owner. This is a question I personally get a lot, which is not only how do you do it all, but Tori, how are you taking care of yourself? And I’m like, well, great fucking question. It’s a great question. We also talk about redefining your idea of what success is and what success looks like, and the power of podcasting. If you’ve ever wanted to start a podcast, if you love listening to podcasts and you thought, what if I could do this, and then maybe you thought, oh, it’s too late to start, it’s not. We’ll talk more about that in the episode. So without further ado, let’s go ahead and get into it.
But first a word from our sponsors.
Are you at a cabin?
Jenna Kutcher:
In our lake house.
Tori Dunlap:
Yeah, that’s what I thought. It looks so nice.
Jenna Kutcher:
We’re in the north woods of Minnesota, a town of 1200 people. The nearest Target is two and a half hours away. It’s very quaint and sweet.
Tori Dunlap:
That sounds lovely. Does it get really snowy? Do you winterize the cabin?
Jenna Kutcher:
Well, yeah, we can go snowshoeing. We got the kids snowshoes, it’s so cute. Yeah, it’s beautiful.
Tori Dunlap:
That sounds lovely. That is on my short list of things that I would love to have someday, is a cabin, because I live right by the forest here in Seattle. If you go 45 minutes east, you’re in national forests.
Jenna Kutcher:
The woods.
Tori Dunlap:
Yeah, mountains. Yeah, and I love it up there.
Jenna Kutcher:
There’s something about being in the woods, we’re overlooking Lake Superior, and I don’t know. Everyone is a different person here, I make soup. I don’t normally make soup. I don’t know, I come here and I just want to make soup.
Tori Dunlap:
What’s your favorite soup? What are you making?
Jenna Kutcher:
I made lasagna soup in the crockpot yesterday. It was actually really good.
Tori Dunlap:
That sounds really good. Hi, I’m so excited to have you.
Jenna Kutcher:
Thanks for having me.
Tori Dunlap:
This has been a long time coming. We love asking money experts and entrepreneurship folks, what is their first money memory? What is the first time that you remember thinking about money, considering money? What does that look like for you?
Jenna Kutcher:
Yeah, I will never forget. So my parents gave us $3 allowance every week growing up, and we had to do weekend chores. So before we could do anything else, we had to do weekend chores. And so my mom had these little mason jars on the shelf in my room, and $1 was for saving, $1 was for spending, and $1 was for giving. And so I loved that because it was just that visual representation of what that looks like. And as a mom myself, I feel like there are a lot of different principles that I can now recognize and see just what it instilled in me. So that was probably my earliest memory.
My mom also had this sheet, and if we wanted to earn more money, it would be organize the hair drawer, $1. Clean out the utensils, $2. And if you wanted to earn money for things, you could do specific chores. And that was one of the principles that we walked away with.
Tori Dunlap:
The earning potential was seemingly limitless, which is very interesting.
Jenna Kutcher:
It sure was. If you wanted to get your hands dirty, it was.
Tori Dunlap:
So you and our mutual friend and one of your best friends, Amy Porterfield, who been on the show, have very similar stories, worked in corporate for a while, realized it wasn’t a good fit for you, so you started a business. Can you talk to me a little bit about your days as a photographer and when you realized that nine to five work wasn’t for you?
Jenna Kutcher:
Yeah, I will never forget. So right out of college, I had a job offer and I worked for Target Corporate and I made $55,000 a year, and I was just so grateful to finish out college with a job. And I’m from Minnesota and Target corporate is in Minnesota, and so it really felt very important. It just felt like, wow, she really did it. And I’ll never forget, I was a couple of years into my position there, and Target has an amazing leadership, they really developed their leaders. I commend that company for a lot of the things that they do right.
But I’ll never forget sitting down with my boss, who was a woman, and she said, congratulations, we’ve planned out the next five years of your life. And I remember in that moment having this visceral reaction of like, they didn’t even ask me what I want for my life. They didn’t ask me. And I remember them painting this picture of like, and then you move up to this position, and then you move up to this position, and here’s the path. And every position, you earned more money, but you also had to spend more time. And I recognized that they had never really learned what my currency was, which was time.
And so that was that moment for me where it was like, sure, I can keep climbing, but I’m only going to be climbing further away from what I believe really matters in my life. And so that was that moment for me of this doesn’t resonate, this doesn’t fit. It sounds successful, it sounds impressive, but it doesn’t feel that way. And I’ve had a lot of moments like that in my decade of entrepreneurship, but that was that first one that really said, I’ve got to figure out something different. I don’t know what it is, I don’t know what it’s going to look like, but I’m going to move in a different direction.
Tori Dunlap:
It’s so interesting that it wasn’t here’s what your career path at Target will look like or even your career. It’s we’ve mapped out your life without consulting you for the next five years.
Jenna Kutcher:
Yeah. And it’s crazy too because in that timing, I was planning my wedding to my husband, we’ve been married for 12 years, and I didn’t want children. And I will never forget at that meeting, I looked over and I saw this picture of my boss’s two young children on her desk, and I felt this disconnect of she is working 10, 12 hours a day, if she’s lucky she gets to see her kids before bedtime. And I remember going back and sitting down at my desk and seeing this picture of my husband, you know like it’s on your desk, you put the things that matter the most to you. And I had this moment of, for the next five years, do I want to look at a picture of him or do I want to figure out a way to actually be with him?
And I think that for a lot of people, you can resonate with that of like, I am spending my days in my life looking at what I say is most important to me, but not even experiencing it. And that was just a really interesting play of, whoa, is there a different way? Can I find a different way? What does that even look like?
Tori Dunlap:
So what was that next step for you when you were like, I have had a similar moment in corporate where I was just like, wow, disillusionment immediately, where just the rose color goggles came off and I was like, oh, I thought, very similar story, literally the exact same amount of money. I was making 55K at my first job, was stomping the pavement and was like, I’m going to girl boss so hard. And then I got in and I was like, oh, no, no, this is awful. No, no, no, no.
Jenna Kutcher:
Yeah. You know what’s so interesting, and I think that your listeners can relate to this is that in today’s society, I feel like we are very quick to abandon something. It feels out of alignment and we’re like two weeks notice, I’ll figure it out. And I do believe there are two types of people. There are the people that are like jump and the net will appear, and then there are the people like me who are like, let me weave the net piece by piece until I feel safe to jump.
Tori Dunlap:
We talked about this on your show. I have the same theory that it’s like we are top weavers. I’m like net and then backup net, and then the backup backup net.
Jenna Kutcher:
Yes, yes. And so that’s exactly how I was. And so I have pivoted so many different times in my career as I start to feel that out of alignment again, okay, how do I want to get into alignment? And so for me, I had actually bought this $300 camera on Craigslist because we couldn’t afford to higher engagement photos and all these things in the wedding planning process. And I loved weddings, I loved bridal magazines. It was pre-Pinterest era, I was making collages. I have a binder still to this day from when I planned my wedding. I just loved that world. And so I bought this camera because I wanted to document our lives as we were planning our weddings and these DIY projects, we couldn’t afford to do a lot for a wedding. And so I was reminded that I was creative again.
And it was interesting, because in that nine to five job, I was in HR, I was managing a team of 150 as a 23-year-old, and I didn’t have creativity. I was just following the rules, following the path, following the plan. And when I bought my camera, all of a sudden I was like, oh my gosh, I love creating, I love learning. I’m curious about this. How do I do this better? What does this look like? And I think it just reminded me of, no, you are a human outside of this structure and this work.
And so for me, I ended up building this photography business, having never taken an art class, having never learned photography, having never thought about entrepreneurship. But I built it over time in one year. I said, I’m going to give myself one year runway. If I can match my salary at this job, I will leave. And I was able to do that, and that was the start of my entrepreneur journey.
Tori Dunlap:
Something so crucial that you just said, actually two things. One is building the thing that you want to do eventually while still having the safety net. I did something similar where I was like, I don’t want to ask my business to fund my life before it’s ready, and then become resentful of that business or resentful of the work I was doing. And then two, you gave yourself a very concrete goal. It was similar with my 100K, it was like the 100K is the permission slip I need to leave. So how can somebody listening do the same thing for them if they want to be an entrepreneur someday?
Jenna Kutcher:
Yeah. I think that without having safety and security, it is entirely hard to be creative.
Tori Dunlap:
Totally.
Jenna Kutcher:
And I think that for so many people, they have this big dream of getting paid to do what they love. We hear all of those cliche wall quotes, like if you do what you love, you’ll never work a day in your life. And I don’t believe that to be true. And I also believe that if we are abandoning or walking away from safety and security, we will not stand in our creative power enough to build something that actually feels good. And I think that’s what happens for a lot of entrepreneurs is that they abandon and they’re like, I’m going to figure it out. And in figuring it out, they take on any job, any client, any money to come in and all of a sudden they’re building something that doesn’t actually feel the way they thought it would. And I think so many entrepreneurs end up building jobs for themselves.
And so it’s so interesting because for me, every time that I’ve wanted to pivot or change, I’m like, what is my safety and security amount? What do I need as my enough point? And how do I free up time? When Target told me, here’s what you want for the next five years, you’re going to earn more money, but you’re going to work harder and you’re not going to have time, that didn’t resonate. Time has always been my currency and time as I was unlocked real currency for me.
And so for somebody listening, you have to figure out what is that enough point and how do you have that safety and security? And then really value your time above all else to pursue curiosities, to be creative, to figure out what type of business you want. And I love that you said, I didn’t want to make my business try to create results that it wasn’t ready for. I think a lot of people do that and then they end up building something that a year from now, two years from now, five years from now, they’re like, this is not what I wanted, or this is not the business I imagined.
Tori Dunlap:
I remember I’ve told you this, and I think I said it on your show as well, you were one of the people I looked to when I was building Her first 100K. And I thought to myself, I know I’m capable of that and I want it right now. I was very impatient. And I had not cut my teeth, I had not built a kind of business to support what I knew I was capable of. And if I did, magic Genie popped up and was like, here is a business Allah Jenna Kutcher. At the time, I would not have been able to handle that.
And so I think that’s the other thing is everybody looks like an overnight success if you discovered them last night.
Jenna Kutcher:
Yes.
Tori Dunlap:
It’s one of those things where I was looking at you and folks like you and Amy and being like, that’s the kind of business I want. And then if I had magically acquired that business somehow, I would not have had the tools or the expertise to be able to run said business. And so there’s a lot of that time where you are building and testing and not making money. And for me, that was largely done while I still had a nine to five paycheck. And I am really thankful I did that, and I think you are too.
Jenna Kutcher:
Oh, absolutely. You know, it’s so interesting too, because I was still shooting weddings five years ago. So I go on to be this wedding photographer and then I have this other experience where I’m like, oh my gosh, I built another thing that requires me to show up. And again, didn’t abandon that thing, it was working for me. And I think so many of us have aspects of our lives that are working for us. Even if the whole doesn’t feel like we thought it, there are gifts in the grievances. There are things that we are missing right now. And it’s so wild to me because it’s like, a lot of times we just think we’re going to throw out the baby in the bathwater, that is how we feel about things, when it’s like, take an inventory. There are things in your life right now that are working for you, that are resonating. It’s not all bad.
And so I think that for so many women, especially when we start to feel that out of alignment, we want to do everything to get right back into alignment. And it’s like, it doesn’t always work that way. I feel like the path is very windy and it takes time, and we don’t often give it the time it needs.
Tori Dunlap:
I would love to hear after you quit, you’re starting to do more photography, you’re featured in all these wedding magazines, what is the next point where you go, oh shoot, I do have to show up for this all the time? This isn’t as may be as passive as I’d want it to be. And I think of people out there who are hairdressers or other photographers or people who are actually showing up or have to show up to do something, what does that transition look like from, oh, I’m building a business, but I’m still showing up my own employee to something more passive?
Jenna Kutcher:
So I want to give a trigger warning for your audience just in the form of fertility and miscarriage, because that was a huge piece of my journey. So if this doesn’t align with you or resonate in your story, just skip ahead three minutes. It was so interesting because I was at the top of my career, and I’ll never forget the day that I hit six figures. I literally was standing in the shower and I was washing my hair with the same Herbal Essence that I had the day before thinking, I thought this would feel different. And if I was really being honest, I was super burnt out. Being in the Midwest, our wedding season is very condensed because of winter. So I was shooting every single weekend, sometimes back to back doubleheaders, driving across states, charging gear overnight and offloading pictures, and it was just a lot.
And so my husband and I had been married for over five years and we were like, we don’t want kids, we’re never going to have kids now. No, no, kids aren’t for us. And something just changed and it’s really hard to describe it, because I admire people who choose to not have children. I respect the people who are on the journey of having kids, and I love the people who have chosen that for themselves. And for me as a wedding photographer, I literally had to plan our future family around my career. I was the breadwinner. And so I was like, I have this very short window of time each year that I can get pregnant. And then by the time I’m out of my first trimester, then into my second trimester, breastfeeding, I had to think through the logistics of all of this so deeply because of the type of business I had.
And our story was one where we got pregnant, had a loss, waited an entire year again to try again, got pregnant again, had another loss. And that was when I had to show up. I got the news that there was no heartbeat, and I had to show up for a wedding the next day. And I had to put on my happy face, and I had to just have joy coming out of my body when all I wanted to do was be in the fetal position. And it was one of those moments in life where it was like, nothing else matters. Everything feels so trivial. Doesn’t everyone know my world is caving in on me, and here I am shooting photos and telling people to smile on the happiest day of their life.
And I vowed that day that I would figure out a different way, because I had built this business that couldn’t run while I rested. If I stopped, the business stopped, the income stopped. And that’s scary. That’s this scary realization of I built something so wildly successful and in this moment where I need to be a human being, I can’t. I have to perform. I have to show up. And so many service-based business owners, and even people just in the service industry can understand that if you don’t show up, you don’t get paid. That’s really scary, because there will be times that life doesn’t allow you to show up, whatever that looks like for you.
And so in that moment, I just said, there has to be a different way. There has to be a different model. And that was when I really started on this path of going more into this online world and this online space and sharing the things I had learned and how I had built that, and what I regretted building and how I would build it again and all of that. And that really changed things for me and my career.
Tori Dunlap:
Before I launch into the next question, I’m tearing up over here. Thank you for your vulnerability.
Jenna Kutcher:
Miscarriage is unlike any loss, and I don’t think people, if you’ve never experienced it, you don’t understand it, because not only is it the loss in the moment, but it’s also the loss of future joy. You never get blissfully ignorantly pregnant again. And it brings so many emotions. It’s robbing you of this future where any other type of loss, it’s this finality, but miscarriage really does steal future joy. And that’s a really weird thing to walk through. And it’s a really weird thing to experience. And it’s interesting because I’m at this place now in my life, I have two beautiful daughters, and I have been thinking about my losses a lot. Not in a way of everything happens for a reason because I think that is the least helpful thing you could ever say to someone, but in a way that I learned so much through those losses and I learned how to move with them, not move on from them.
And it’s interesting because if I would’ve had that first baby when I was a full-blown wedding photographer shooting every single weekend, I would not be the type of mom that I imagined myself being. And so it was a very interesting thing where I was given the gift of time, even though it didn’t feel like a gift of figuring out this waiting season, I’m not going to waste it. I’m going to work through it, but I’m going to work really intentionally to build something that is worth waiting for. And so it’s been an interesting thing, for sure.
Tori Dunlap:
Yeah. Was that transition from shooting every weekend twice a weekend to coaching other business owners, did you receive any pushback? I think you were one of the first, at least one of the first people I remember doing the coaching other business owners about how to be a business owner. Was there pushback? Was there confusion at that pivot? How did that feel?
Jenna Kutcher:
Yeah, no, it’s interesting. If there was, I’ve blocked it out. I’ve blocked out a lot of things in my life, like childbirth. And it’s interesting, so the day that I hit six figures, I’ll never forget, recognizing and waking up to this doesn’t feel the way I thought it would. And the next day, my husband came home from work, he was selling wine in grocery stores, and I said, I’m going to say something kind of crazy. And he said, what is it? And I said, screw six figures. I was so much happier when I earned $50,000 a year and I had a life. And I asked him and I said, what would you think if we went back down to that? And I said, we have been living from our enough point, we could do it financially. I want to have my life back. I want to have weekends, I want to have summer. I want to enjoy the weather when it’s beautiful. And he was totally on board.
And what ended up happening is that when I claimed back that time and said, I’m going to work half the amount of time I’m going to shoot half the amount of weddings, I got back time and capacity in my life, and I got creativity back again. And when I got that creativity and that curiosity, that was when I started to learn about this different way of doing business. And so it was wild, because in the year that I planned to earn 50K, it was in the year that I quickly approached earning seven figures. And it was totally unplanned, and it wasn’t, it wasn’t the journey. And it wasn’t about the money, it was about unlocking this different way.
And I had been coaching other photographers in my tiny little apartment that I lived in because people had paid attention. They’re like, where did she come from? How did this work? How did she get all these clients? What was this? And I recognized that I was doing something different, but I didn’t yet know that it could translate beyond the photography realm. And so that’s when I started my podcast. And my podcast was really an experiment. I had taken the season off during the winter and I was lonely. I know you get this, Tori, when we first connected, we’re like, is there anyone else out there doing this, because I feel so isolated and alone?
Tori Dunlap:
So lonely.
Jenna Kutcher:
So lonely. And so I started my podcast as a means to just talk to other people who were entrepreneurs who were doing it. And there wasn’t really pushback because it wasn’t coming from a place of I figured this all out and here are all the answers. It was, I am figuring this out and I’m taking you with me while I do it. I think nowadays, there is this strong opposition of people wanting to be seen or being willing to be seen as a beginner. We want to show up when we have it all figured out. And when I look at the last decade of my life, it has been a series of saying, I have no idea what I’m doing, but I’m taking you with me and I’m sharing as I’m learning. And that’s so fascinating to me is, nowadays people blanket it saying, I’m an imposter. And you’re not an imposter, you’re a beginner. You’ve never done this before, and you’re just afraid to be seen as a beginner. And that’s the problem is, I am constantly a beginner and I’m willing to take people with me on it.
Tori Dunlap:
Or we get the cringe comments. And it’s like, great. You look back, if you have time, you can scroll all the way back to her first 100K’s Instagram in 2018, and it is cringey as hell. It is so cringey. Same. And I love that for us.
Jenna Kutcher:
No, exactly. I look back at it and I’m like, oh, she was so cute. She was trying, I have no shame. I’m like, you know what? She was trying, she trying to figure this out.
Tori Dunlap:
Yep. I love that.
Jenna Kutcher:
I know I haven’t deleted anything either because I’m like, go back and look, because it’s just showing up. It’s literally just showing up. And I think people don’t do that anymore.
Tori Dunlap:
If you’re willing to be super transparent, you mentioned the transition from six figures not feeling the way you wanted to feel to then almost seven figures, but cutting your time in half? Was it like half? How did you do that? Were you raising your rates? Were you working with a different kind of client? What were you doing to actually make that happen?
Jenna Kutcher:
So the first year, I shot 25 weddings. The second year, I shot 27. The third year, I shot 30. And that was the year where I was like, I am at the top of my game and I feel like crap. I just had hit burnout, which I think so many of us have experienced. And so that year I said, I’m going to go down to 15 and we’re going to see what happens. And so for the next two years, I shot 15 weddings and then I went down to seven. My rates were increasing, but I didn’t honestly care. Again, I was willing to go back to $50,000 a year if it made me happier and gave me more time.
And what was interesting is that as I started to do more in this online space, I took all of the things that I had learned from mentoring other photographers and created my first digital course. I had 500 people on my email list and I put it out into the world. I was actually just reading those emails the other day, because I love looking back at that version of me and figuring out, wow, she really just went out there. Wow, she had a header in her email with puppies in it that had nothing to do with puppies, just random things like that. And I’m like, you go girl.
But as I started to recognize, okay, I’m telling these photographers the same things. They’re all wondering about branding, they’re all asking about email templates, they’re all looking at my pricing guide. They’re all wondering what I say on my website and how I say it. When I started to see these trends, which I think so many of us can identify if we put ourselves in the position to allow people to ask us questions, I recognized, wait, I can help more people outside of central Wisconsin and I can teach them these things in a bigger way, in a bigger scope. And the first time I ever launched a course, I ended up earning $25,000. And I was like, wait a minute. This is something that’ll allow me to make the impact I want to make, but also give me that time freedom that I really deeply crave.
And that’s where I started to go deeper on that. I was still shooting weddings just a few years ago because that part of me was still working for me. It still gave me that safety and security I needed to keep spreading my wings. But it also was that launchpad of like, okay, what is the next thing? And okay, now I have safety and security in that, okay, what is the next thing and what does that look like?
Tori Dunlap:
I did something extremely similar where I was one-on-one coaching with people at a Starbucks in Seattle, and then was like, oh, people are asking me 90% of the same questions, let’s turn that into a workshop. And then I did the workshop for a while where it was as many of the 100 people could show up, and then it turned it into a course. And so very similar, almost any business owner can kind of do this by, to your point, saying what questions do people always ask me? Or with the clientele I’m trying to appeal to, what are their pain points? What are they always confused about? And then serving them in that way.
Jenna Kutcher:
Yeah. And I feel like too, people are too close to their own genius to see it. What is common sense to you could be life changing to someone else. And I think that we forget that. And the other part of it too is like we were saying, you and I have both showed up in the middle and been like, here we go. We’re trying, we’re doing the thing. And what I think people forget is they want the after photo, we are obsessed with befores and afters in this society, but you are way better positioned to help somebody that’s just a few steps behind you. We want to wait until we’re fully removed from the situation, we have all the answers, when in reality, I would much rather learn from someone that is on the same journey, that is just a little bit ahead of me, that has just figured out a few extra things.
And so we discount the fact that not being further ahead is actually a really great way to connect with people on a much deeper level, because you can relate to them, you understand them. You know what they’re going through, you can anticipate their problems before they run into them. And so this is your reminder, don’t wait to start showing up. Showing up right now is what is going to help you unlock it.
And then also, Tori, you and I have done this for each other where we’ve been a mirror for each other, is invite people to reflect into you what are you great at? What are you known for? What would we love to hear you give a presentation on for the next hour? There are so many things within you that just come innate that are so beautiful and maybe even simple, but you discount them and think, surely everyone knows this. Let me tell you, everyone does not know what you know. And I think that that’s a beautiful reminder.
Tori Dunlap:
I love what you just said too thinking about the person who’s just a couple steps behind you. I think now, I love folks like Sara Blakely who runs Spanx. Sara Blakely is in an upper echelon that I am not in. And so it doesn’t make sense if I was looking for mentorship to reach out to Sara Blakely. One, her inbox is crazy. Two, she runs an e-commerce goods business. That’s not the kind of business I’m trying to run. So it’s so helpful to think about reaching out or learning from the person who’s just a couple of steps in front of you and doing the same thing for you of like, yeah, what did I learn last year? Or what did I learn two years ago that could be helpful for somebody?
Jenna Kutcher:
Yep. I love that.
Tori Dunlap:
We get questions from our community on starting that small business when they don’t have a lot of money to invest, and maybe they don’t even have a lot of time or they don’t know if they have a lot of time. What advice do you have for people in that camp?
Jenna Kutcher:
Yeah. So I always ask the question, is this a nice to have or a need to have? So when I was starting my photography business, oh my gosh, I wanted to buy all the lenses, all the cameras. I wanted to buy all that gear. I didn’t have the money to do that. Remember, I started my entire career on a $300 camera from Craigslist, and I didn’t even know what the numbers on the lens meant. I was literally someone starting blind.
And so there are so many things as an entrepreneur that are nice to have and very few things that are need to have. In order to be a business, you need to have an offer that you can exchange for some sort of currency, whether it’s time, money, energy, however you’re getting it back. And so when you are starting out, you need to do the lowest level of investment, but you have to have the greatest level of buy-in, personal buy-in. If you don’t really believe that this can become a thing, if you don’t really do it. I mean, the amount of times that I created a logo in Microsoft Word because Canva didn’t exist and I built a free WordPress website, there were so many things that would’ve been amazing to have, but I didn’t need to have them.
And the other thing that I did, and Tori, you’re very similar on this is, because I was working my nine to five job, I was also paying off student loans, there was a lot of other things happening, paying for my wedding, all these things happening, I just barely had pennies. And so for that first year of my photography world, any money that came in went straight back into the business. I was just breaking even so that the next year I could really profit. And so how can you continue to reinvest wisely and leverage that safety and security to give you that feeling that you’re not in that scarcity place?
And so ask yourself, is this nice to have or is it a need to have? You don’t have to have a perfect logo or a perfect website or even business cards to have a business. You have to be selling something and you have to put something out there that people can exchange something for, and it’s way simpler than you’re making it.
Tori Dunlap:
Yeah. And I think it’s also running a lean business too. I chose something that was like, okay, it’s going to take a lot of my time, but that’s what is available to me. I don’t have a bunch of money, I am not trying to invent something or put an app together. I am just trying to build a blog, and I can do that with my own time. I think a lot of people, the big dream business idea they have is something that’s going to take millions of dollars of funding. And then they’re like, well, I can’t do that. I’m like, yeah, you have to get funding from somewhere else. That’s a VC focused business. If you want to do that, great, but that’s a different kind of model.
For you and I, it was like, okay, the thing we do have, we don’t have financial currency, we have time. So how do we make time because this is something we want so badly? And that’s the other thing is it’s like I was willing to sacrifice some of my nights and weekends because it was the thing that I wanted really badly.
Jenna Kutcher:
Yeah, absolutely. And I think you and I have a very similar outlook on hustle culture and what that is. And it’s really interesting, because I do think that hustle is required to get a lot of businesses off the ground, but if hustle is the only state that your business can profit in and the only state that you can work in, then it’s not a sustainable thing. And so when I look at my business and when I think of a lot of successful entrepreneurs, they did work to burnout to have the breakthrough of there’s got to be something different, there’s got to be a better way. And I think that the problem is that we’re perpetuating this hustle culture in the sense of hustle is the only way forward and it’s the only way to grow. And I think it is a way to level up, but you also have to be able to draw a line in the sand and say, enough is enough. Now I rest. Now I recharge. Now I come back to the vision. Now is the vision aligned?
And so it’s really interesting, because I think that there is this polarizing messaging in the business world of like, just hustle hard or wake up earlier, do more. And I think there is a season for that, but that season has to end and it has to have a line where you’re like, okay, enough is enough. Now I’m going to move on to the next part.
Tori Dunlap:
Yeah. That’s so hard, because I completely agree and also I can hear the comments where they’re like, capitalism and hustle, and I don’t think it’s the hustle forever.
Jenna Kutcher:
No. Oh gosh, no. That’s why it’s like, we gave ourselves that one year. Because I worked nights and weekends for a year on top of a corporate job.
Tori Dunlap:
Because you wanted it, right? It’s kind of like when I talk about spending money, it’s not like, don’t ever spend money. It’s you’re not spending money here so that you can spend money over here. It’s not deprivation. It’s oh, I’m doing this thing because I really want it.
And you and I are both under the same imprint for our book, like you know, we were texting back and forth, I sprinted so hard. My team, God loved them, sprinted so hard during that time. And of course we have to continue running the business, but a lot of things were like, okay, we don’t have the book anymore to worry about. I was willing to sprint. I’ve never been on a run in my life, so this is a bad metaphor, but when you run, it’s like sometimes you’re jogging, sometimes you’re sprinting, sometimes you’re walking, sometimes you’re doubled over. Maybe just me.
But that I think is the metaphor for business owners is like, yes, sometimes for me, me wanting this, I was willing to work the time and spend the energy and do that because it’s what I wanted more than anything.
Jenna Kutcher:
Yeah. And for when I launched my book, it was a grind time. And then I literally said, one month after my book comes out, I’m taking an entire month off. I have to put parameters into my life that help. I always think of them as when you go bowling and there’s bumpers and it keeps the ball down the path, I’m like, I need bumpers in my life in the form of boundaries or else I could be my own demise. And I think a lot of people can relate to that, I am my own worst enemy at times.
Because a lot of people listening to this might relate, and we don’t often talk about it, but hard work comes easy to me. I was raised, I had multiple jobs growing up. I cleaned limousines, I drove a forklift, I worked in a pro shop. I worked for Abercrombie and Fitch, I did all the things. And hard work is easy, hard work is my autopilot, hard work is my go-to. Rest takes me a lot of work. I had to learn how to rest and relax without guilt. And so it’s finding that balance and putting up those bumpers and boundaries in your life if you know that you’re prone to one way or the other, so that you can stay in check and stay in alignment, moving towards what you really want for your life.
Tori Dunlap:
I’m giggling because you just added me so hard. I was yeah, it’s so hard.
Jenna Kutcher:
I know. I know that about you. I mean, what do you think that is? Because hard work, it can come easy to us, but also rest can be really uncomfortable, right?
Tori Dunlap:
Oh, so uncomfortable. The way I phrased it is like, my ambition is a drug, and it’s part of the reason why I’ve gotten where I am is it’s like, sometimes that drug is caffeine, and sometimes it’s something harder where I have overdosed and then I am burned out and sick, sometimes physically sick. But then I think, oh, I just got to keep going. I got to keep going.
And so I have the past couple years especially, tried to get really, really honest with myself about how I use my ambition, when I use it and when I need to just leave it for a while. And I’m still bad at it. I’m working at it.
Jenna Kutcher:
Yeah. I think a lot of people can relate too, because part of the reason why entrepreneurship is beautiful and it is not for everyone, is that at the end of the day, if it’s successful, a lot of it hinges on you. And if it’s failing, a lot of it hinges on you, and we take that responsibility on and wear it like a badge. But at the same point too, the ambition that got us to this point can also be the ambition that leads us to other places like burnout.
And so it’s really interesting for me because I’ve really had to learn what is my life outside of this? What is my identity outside of this? And I think this goes whether you’re in a corporate setting or an entrepreneur. When I left my corporate job, which had a long title that sounded very impressive and became a photographer, which sounded like a cute little hobby, I really had to get comfortable with what is my identity and where is my worth coming from? If people think this is just a cute little hobby and they don’t realize it’s a booming business, does that really impact what it is in my life?
And so it’s really interesting because I think a lot of people listening to this are deeply ambitious, and they are willing to pursue things with a great deal of work and ethic. And I think at the same point too, it’s this constant redefining of what does success look like for me right now? Because it changes, right? As life changes, we change.
And so if you’re listening to this and you haven’t really evaluated, what does success look like for me right now, and what does it actually feel like and when do I feel most successful in my life, those are some really great questions to figure out is time your currency right now or is money your currency? And I don’t think either one is good or bad. There are times in my life where all I want successfully is to put my kids to bed at night and be there when they wake up in the morning. And that has nothing to do with money. And there are also times in my life where I want to earn enough money to help pay for my parents’ medical bills or to do different things like that. And so it’s like, what does it look like for you right now? And I think that’s a really beautiful question to start with.
Tori Dunlap:
I might be journaling about that tonight. What does success look like for me?
Jenna Kutcher:
I can’t wait to hear your thoughts.
Tori Dunlap:
It’s going to be interesting.
Jenna Kutcher:
So Tori, finish this statement for me. I know I’m being successful when?
Tori Dunlap:
Oh, my entire body just flooded with sweat.
Jenna Kutcher:
Ooh. All right.
Tori Dunlap:
And I’m a little teary. I’m a little teary.
Jenna Kutcher:
This is why we’re friends. We’re mirrors for each other.
Tori Dunlap:
Oh, interesting. Okay. I’ll just be really honest. I don’t actually believe this, but you said success and I thought money. That’s the first thing I thought of. That’s part of it, but I have a lot. I’m good. At least in this season of my life. The business needs to make more money to keep the lights on, but I personally am good for a little bit. And also I’m like, yeah, but isn’t it? Interesting, okay.
This is not what I actually believe though. I feel like it was a immediate word association. Will you ask me the question again and I’ll sit with it?
Jenna Kutcher:
Yeah. I know I’m being successful when?
Tori Dunlap:
I think, first of all, making an impact in the world. I think that’s my true answer. And also I think where for me, I don’t have to work so hard for the result that I want.
Jenna Kutcher:
Ooh, that’s good. I like that. More ease.
Tori Dunlap:
Yeah, because of my ambition. I don’t know how easy it’s actually been, because I’ve kept going. And so it’s felt hard recently.
Jenna Kutcher:
Yeah, I agree.
Tori Dunlap:
Anybody listening, and also Kristen will know-
Jenna Kutcher:
Yeah, it’s like new lows, new devils.
Tori Dunlap:
Yeah, sure. She’s a poet, she didn’t know it, baby.
Jenna Kutcher:
I mean, it’s interesting because there have absolutely been seasons of my own life in business, and I think for anyone listening too, it’s like there are times in your life where you’re just like, this is it. I’m in alignment, I’m doing what I’m meant to do, everything feels good, there’s that flow to it. And then there’s also those seasons of resistance, and it’s not always a bad thing, right?
Tori Dunlap:
No.
Jenna Kutcher:
That’s where grit comes in. But yeah, for me it’s like I know I am being successful when I feel peace in my day, whatever that day is, whether it’s being a mom or it’s working hard, and that’s what I keep coming back to.
Tori Dunlap:
That’s really what my answer, it’s easier.
Jenna Kutcher:
I saw one of my friends recently said that the best sign of success is a balanced nervous system, a regulated nervous system. And I loved that, I was like, wow.
Tori Dunlap:
And mine is not, I just went to a naturopath and I was like, my hormones are nuts. And she’s like, talk to me. She’s like, is your work stressful? And I was like, how long do you have?
Jenna Kutcher:
Many women can relate.
Tori Dunlap:
Yeah, I’m in fight or flight constantly. But the interesting thing was since I saw her, I’ve made more intentional choices. This was only a couple of weeks ago, and I feel better.
Jenna Kutcher:
Good.
Tori Dunlap:
Even in the past couple of weeks, I feel better. So yeah, it’s interesting, that’s the other thing about brains is sometimes your brain says something that you don’t actually believe, because for me, at least in this season, it’s not really about money for me personally. Of course, the business has to make money to keep the lights on, but that’s not what I actually feel. That would be a great question is the difference in your brain and body. That’s something that I’ve learned a lot, especially as an entrepreneur, is like, I am such a cerebral person, I always want answers to things, I want the explanation. But often my brain thinks things that I either don’t believe or don’t want to think, and my body knows differently, but I’ve had to learn to tune into my body. And I think you’ve been on a similar journey too.
Jenna Kutcher:
Yeah. So I wrote a book called How Are You Really, because the really part is the part that we never get to in this life. You think about it, you go to the grocery store, you see a friend and it’s like, hey, how are you? Good, busy, whatever, and then you move on. And it’s like there are very few times where we actually lean into that. And I think what’s so interesting about that is for me, I need time to sit before I make decisions. I’ll have that gut response, which is usually yes, more, let’s do it, all these things. And then when I have a moment removed from the emotion of a question, I’m like, does this really fit with me? Am I actually excited about this? Will I be excited about this three weeks from now when my period begins? How am I actually going to feel about all of these things?
And so it’s interesting, I think the more that I learn about myself, the more that I give myself that time that I used to not allow in making some of those decisions. And it’s interesting because I feel like I’ve been an entrepreneur for 12 years now, and I’m at this place where I’m very much redefining what do I want this to look like and how do I want this to feel? And what is the true mission and what does that look like? And a lot of people never take that beat to re-ask those questions because we don’t recognize that they change. And I think for so many of us, we’re multifaceted, ever evolving humans if we’re on this journey of learning and growing.
And so it’s so interesting to really ask yourself those questions, how am I really? Does this feel successful for me? Am I on the right path? Am I bringing the right people with me? What does that look like? And so I am the queen of 21 questions, both for myself and for the people I love, because I feel like often we don’t even pause long enough to think of what that answer would look like.
Tori Dunlap:
The recurring theme of the show in the last year has been this element of discomfort and embracing the discomfort, especially when you know that you want your life to change or you know that your life needs to change, but you’re really scared to make that call, whether that is leaving your relationship or leaving your job or starting a new business, or at least just putting yourself out there. And I think a reaction I even had to just you asking me questions and saying that was like, do I even want to know? Because if I ask myself-
Jenna Kutcher:
You have a responsibility then.
Tori Dunlap:
… then I’m going to have to make a decision. So how do we learn to embrace that, especially in regards to entrepreneurship or some sort of big life change?
Jenna Kutcher:
Yeah. Oh my gosh. Okay, so there’s two different things that I want to share that have just been a theme in my life that I think you can just carry with you wherever you go after this. So the first one is, is a lot of times when we think of letting go, it feels very scary. We don’t want to let go of things. Even if we know they no longer fit us, they’re no longer serving, it’s exactly why I still have pants from when I was 18 years old that I will not let go of.
But I have been thinking of this theme of loosening the grip. I think a lot of times we are white knuckling our way through life, through relationships, through careers, and we’re just holding on so tight and believing this deep level of attachment to whatever it is, whether it’s the identity, whether it’s the notoriety, whether it’s the money. And so I’ve often been thinking about what would this look like if I just loosen the grip? If I let go of control just a little bit? I don’t have to fully let go yet< I’ll know when that time is, but loosen the grip.
The other thing that I’ve been thinking about so much this year is what would this look like if it were easy? How do I invite more ease into my life? And whenever I get stuck, whether it’s a business question or a life question, it’s like, what would this look like if it were easy? And a lot of times it removes that extraneous stuff that’s either holding us back from actually taking that first step, or we’re overthinking it so we’re over analyzing it, or we’re trying to be perfect so we’re procrastinating. And so I often just think of, what would it look like if it were easy, and how do I let it be easy?
And it’s interesting to think that, because there’s so much hard in this world. It’s what a place of privilege to be like, I just want more ease in my life. I can afford to have more ease in my life right now. Most people cannot. But what would it look like if we were to kind of simplify some of those complexities that we’re just overthinking or those thoughts that keep us up at 1 in the morning or 3:00 AM when we’re really asking ourselves, is this my life? Is this what I’ve worked so hard for?
And so those two thoughts have really stuck with me this year of loosening the grip and letting it be easy. And I do think that there is something to be said about you will not miss something that is meant for you. And this isn’t manifesting mumbo jumbo, because I live in this space of where the woo meets the work. I want to have the vision for my life and I want to have this dream of what my life can be, but I also recognize that there’s a lot of work that has to go into making that happen.
And so even when I wrote my book and thought about leaning into that discomfort, I think so many of us don’t even want to admit that we’re faking the enjoyment of our lives, because the second that we admit, that means we have to do something. We’re accountable to actually doing something about it. And the interesting thing is, when we start getting into action, confidence comes from consistency. And when we start to feel confident and when we start to feel worthy, our lives start to unfold in an entirely different way. We see the world in a much deeper way.
And so for me, when I feel out of alignment, when I feel that discomfort, I have to really intentionally set aside time to lean in or else I’m just on autopilot in my own life, but I have to wake up to the reality of like, something’s got to change and I have to be the change maker. And yes, this might be at the expense of other things, but if it’s important enough, I will make time for it and make space for it. And I just think so many of us, we’ve gotten comfortable with living lives that look good, that we haven’t gotten honest about. We’re living a life that doesn’t feel good, and I think that’s a hard reality that a lot of people are facing right now.
Tori Dunlap:
We had a previous guest, Ashley Stall, who said-
Jenna Kutcher:
Oh yeah, love her.
Tori Dunlap:
… if you don’t make the change, the universe will, and that’s going to be the more painful way. So if you have the opportunity to make a choice-
Jenna Kutcher:
I love that, of just loosening the grip a little bit, as someone with control issues, big fan of that.
Tori Dunlap:
I do think there is this element though, where the universe will make the change for you and it will likely be more painful. So if you can make a step towards working to actually change your life-
Jenna Kutcher:
You’ll feel more in control of it, if you’re the one doing it totally. Yes. We’re all control freaks, let’s be honest.
Tori Dunlap:
Oh God, yeah. Speaking of previous guests, we had Dr. Sasha Hamdani on to talk about ADHD in adults and in women, and you were diagnosed with ADHD as an adult. You’ve talked about how it’s made you, or you think it’s made you built for entrepreneurship. Can you talk a bit about that and how you’ve harnessed it as actually a superpower?
Jenna Kutcher:
So it’s kind of wild, because I did this podcast interview with this amazing woman named Tracy Otsuka, and she came on my podcast and I just was interviewing her about ADHD. And at the end of the interview, after we had stopped airing, she goes, you know why I wanted to come on your show, right? And I was like, no, why? And she’s like, you 1000% have ADHD. And I was like, what?
Tori Dunlap:
She diagnosed you from your podcast.
Jenna Kutcher:
She’s a listener of my podcast for many years. And she goes, the things that you do in order to be productive are great signifiers that you likely have it. And so it was fascinating because I went home, I was talking to my parents and my mom goes, oh yeah, your dad had ADD as a kid. And I was like, literally in my entire 35 years of my life, no one once referenced that. No one had talked about it. And my mom was like, oh yeah, he totally had that.
So then it really unlocked this feeling of kind of, again, rediscovery. And it’s so interesting, because I still feel like I’m on this very new adventure of figuring out what does this look like? What does this mean for me? How do I not berate myself for things that just don’t come easily for me, and how do I celebrate the things that do? And it’s been so interesting because I think too, being a mom and trying to manage the mother load of motherhood on top of entrepreneurship and just all these things of the mental checklist that is constantly running in my mind of nap time, bedtime, do they have snacks? Do they have a raincoat for school? What does the school lunch look like? All these different things that I’m trying to juggle, it has only exasperated it to a level of, okay, I’ve got to start working with this and not against it.
And so it’s really interesting because I can see different tendencies within myself. If I am very excited about something, I can joyfully put my head down and work on it for 10 hours a day, and it’s not possible as a mom to do that. And if I am struggling with something, it’s a good signifier that maybe I committed to something when I was in a different head space or in a different part of my menstrual cycle or in a different energy. And so it’s been really interesting to try to figure out what works, what doesn’t work, and communicate that.
And even the other day, I told my husband, I said, I learned something new about myself today. And he is like, oh gosh, what did you learn? And I was like, if you come to me with an open-ended question of what do you want for dinner, my brain goes into a million different directions and I start tracing thoughts, like 10 thoughts in front of the question that he’s asking. I said, if you were to ask me do you want chicken or steak, I can very quickly give you a visceral response and with certainty, I know. And so I’ve been learning just different things like that within me and even to my team, don’t come at me with an open-ended problem. If you were to come at me with a problem and say, here are three potential solutions, which one feels the best for you, I can make very quick decisions. But if it’s this open-ended, I usually go down rabbit holes.
So it’s interesting trying to just learn like, okay, this is why I am this way. It’s not a bad thing. But there are areas that we can work on and there are areas where we also just have to have a little bit more grace for ourself that this is hard for you.
Tori Dunlap:
I love that. I’ll also say as someone who has at least not been diagnosed as neurospicy, just what you said was so helpful and everybody should take note. As opposed to, especially business owners, don’t bring me a half-baked problem. Tell me, here’s the problem, and here are the three solutions I’m proposing. Here’s the one that I like, what do you like? Oh, chest kiss.
Jen, I have to ask you, as someone who has been a long time listener and who has of course also now been on the show, which is so exciting, you host Gold Digger, which has been on the air for several years now, 700 episodes. You’re also someone who encourages other small business owners to start podcasts. What has your podcast done for your business? Why has it been so pivotal? And this is my own personal question, as someone who also hosts a show, is it too late to start a podcast? Because it felt like-
Jenna Kutcher:
Yeah.
Tori Dunlap:
Okay, great. Talk to me.
Jenna Kutcher:
I love it. I mean, I love podcasting and my podcast started as an experiment. And I would say anyone that is listening to this who has had the thought, maybe I could start a podcast, let it be an experiment. Try it out, see if it works, see if it resonates with you. Commit to doing 10 episodes and see how it feels. It is not too late.
One thing I love about the world of podcasting is that people listen to many podcasts. I don’t know a single person who only listens to one show. I listen to celebrity gossip, I listen to health podcasts, I listen to business podcasts, I listen to author podcasts. I listen to a million different podcasts. And I love that, because so many people are craving that diversity in the content that they consume, and so I do not think it is too late.
The ways that my podcast has supported my business is one, it gives me an opportunity to extend a platform to someone who I might not have access to. So many times we want to connect with people and we’re like, I have nothing to offer, and it’s that what’s in it for them mentality. And having a podcast and a platform where you invite people to share their story, share their truth or what they’re learning, that is a huge privilege to be able to extend to someone. And it likely can put you in “rooms” or spaces with people that you might not have had access to if you didn’t have something to offer.
My podcast also has been a huge way of driving revenue, and it wasn’t for many years. And that wasn’t because it wasn’t possible, it was because that was not its purpose. But we have done many different sponsorship models, from sharing about our own products and offers to using affiliate partner links, to having direct sponsors, to having a network. There are many different ways that you can monetize a podcast, and I truly believe that you can monetize a podcast from day one if you go into it with intention.
So what that could look like is saying if you have something that you love, I remember at the beginning of mine, we have been subscribers or users of HelloFresh for years and years and years, and so I just brought up HelloFresh and dropped my own partner link. They weren’t paying me to say it. It paid for our groceries for months and months and months, and we forget that people are always going back to episode number one. Even when you’re at episode 700, there are still people going back to episode one. And so there are different ways that you can monetize it, but I would say if that is your main goal, then it’s probably not the right channel because it takes a lot of consistency.
My podcast has also just been a way to share the evolution. So I have been a blogger since the day I started my business, and I still blog, but it gives me this audio way of navigating life and business. Just as we were talking about looking back at the “cringe” Facebook or Instagram posts, your podcast is this beautiful way of documenting your life and what you’re learning and exploring, and I love that about it.
And then lastly, I would just say too, your podcast is a way to really make an impact and give people that free content. I think there will always be people at the beginning, at that starting line, that just need that free encouragement to get off the ground. It is a way to help open people’s eyes and get them quick results. I love getting people a quick win. I want to say something on my show that you listen to, you apply, you get a result. If you can trust me to get you results for free, then you will absolutely be willing to invest if there’s a different opportunity that you are available to take part in.
And so I love that, because it’s like, I can’t serve everyone for free and not get paid. That just doesn’t work. It doesn’t work in the business world. But my podcast is that free channel that allows people to get that content in and take action on their own to prove to themselves that they’re worthy and able and capable of getting results. And that helps boost their confidence in making the investment, whether it’s with me or anyone else, to take that next step. And I want to be that first person that gets that ball going and gets that momentum started for you so that you believe that you are worthy of taking the next step and the step after that.
Tori Dunlap:
Yeah, that’s so valuable. And to your point about a catalog of content, we can see anytime we go viral anywhere, anytime somebody discovers us, they actually do go back. They go back and start at episode number one. And we don’t have the back catalog you do, but we’re at over a hundred episodes now. And still we know from data that you might be listening, hello, this might be new for you, and you probably started at episode one. It’s crazy to think about the value of what you’re building as this foundation, not only to serve your audience, but for your business as a whole. I think it’s so important.
Jenna Kutcher:
Yeah. And it allows you too, when people ask you questions, I can literally just point them to an episode. We have an episode about that. It actually helps kind of take your frameworks and your brain space and what you’ve learned into a way that is digestible and it lives on. And so it’s like people are searching specific topics and finding episodes from three years ago or four years ago or five years ago. And so it’s this beautiful library of content that allows you to talk about what is most important in your life today while still having and preserving all of those other things that you’ve gone through, learned about interviews, and it’s like this beautiful library of like, oh, just search. I’m sure we’ve done an episode on it, which is awesome.
Tori Dunlap:
Also, Matthew McConaughey.
Jenna Kutcher:
I know. He was so fantastic. He was lovely. Oh man, that was wild. I remember my parents were in Florida that day and I hadn’t told anyone I was going to do it, because I’m always like, you don’t talk about things like that unless they actually happen. And my dad was on the beach and then I messaged him and he had called me and I was like, oh, sorry. I was on the phone with Matthew McConaughey, and he was like, oh, what?
Tori Dunlap:
You also have shared some of the secrets to your success with podcasts and the big things that hold people back from sharing their podcasts. Can you talk about a couple with our audience?
Jenna Kutcher:
Yeah. I mean, I think that for so many people, we don’t want other people to see us trying something new. And so it feels like who is she to do this, or who is she to talk about this? And I understand that, and I have felt that way about other people. And the funny thing is that so many of us, we forget that we have a microscope onto our lives. Everyone else is doing the same thing. No one else is refreshing your feed or watching everything that you’re doing.
And so I think that is literally the number one reason why people aren’t doing what they know they should do, what they want to do, what they desire to do, is out of that fear of judgment. And it’s so sad to me, because it’s like the people that are judging you are likely the people who are staying stuck where they are, and your growth is intimidating. It is. It makes people see maybe where they’re playing small in their life and it’s up to them to choose, do I want to do something different or does this fit me right now?
And it’s so hard because a lot of times when we fear judgment, it keeps us from actually going forward. And fear is the lowest vibration that we can operate out of as human beings. And so if you are somebody who wants to start a podcast or start a business or start a blog or start a side hustle, you have to be so aligned and anchored to why you are doing it and what you are doing it for, that nobody’s judgment can make you play small. Nobody wins when we play small, nobody wins.
And so I would say that’s the number one reason of just who am I to do this? And it’s like, who are you not to? And I know that is cliche, and I know we’ve all seen a poster with that on the wall, but there are so many times in my business where I’m like, oh, I said I was never going to write a book. Should I not write a book because I once said that? Or am I going to show up as the evolved human who changed her mind? There’s so many different spaces. I said I wasn’t going to have kids, now I have kids. I love welcoming the evolution of who I am and who I’m becoming. And I feel like when we do that, we usher other people in to say, it’s okay to change your mind. It’s okay to learn and grow. It’s okay to evolve as a human. It’s okay to try something new. It’s okay to be a beginner. And I think that that is the most beautiful gift you can give other people.
Tori Dunlap:
One of my last questions for you, one of the ways that I got introduced to your story, and I think a lot of people was the Mr Six Pack post. You remember back in the day the Mr Six Pack post?
Jenna Kutcher:
Yes.
Tori Dunlap:
I will let you also tell the story, but basically you had this huge post. You had this post just blow up with a bunch of media features. I had something similar where you had this viral moment and then you’re scrambling to figure out like, oh my God, as a business owner, how do I take advantage of this? So for someone who does find themselves maybe on the other side or in the midst of like, oh, this moment or this press feature, how do you make the most of it?
Jenna Kutcher:
Yeah. So it’s so funny to this day, the headline was Curvy Woman Fights Back with Six Pack Husband. I mean, it was literally laughable. And the whole context of the post was just that I was clapping back at someone who had said, how does a woman like you get a man like him, referencing our bodies? Because at the time I was a size 12, I had experienced two miscarriages, I had been growing a business for five years. I was just in a different spot in my health, in my life. I was starting to unpack a lot of different things that weren’t working for myself and my body.
And it was wild, because I had grown my business and my following, at the time, I had maybe 100,000 followers, like follower by follower. I felt like I knew these people, I know parasocial relationships are really weird, but I had grown it in this way of like, okay, these are my people. They know what they’re getting, they accept the real Jenna. And then overnight, hundreds of thousands of people jumped on. And it was really scary, because it’s like, what do they want from me? What do they expect from me? I’m a wedding photographer. I had been talking about my body for years before that post went viral. It wasn’t a random post. Because I truly believe that how we feel in our bodies affects how we show up, and how we show up affects what we do and the way that we speak up and the way that we create in this world. And I think that not enough women talk about that, because we are withholding success and joy and leverage in our lives because we don’t feel confident in the skin that we’re in.
And so it was wild when this moment went viral because behind the scenes, we had suffered two miscarriages. We were in the process of trying again for the first time. And I remember fielding calls for the Ellen Show and being in my fertile window and being like, what is that? If only people knew what this quote curvy body was going through and what that actually held in my life at the time. And it was such a double-edged sword, because as a business person, you’re like, who are these people and what do they want for me? And what does this mean for me and my business? And it’s been beautiful because the same messages that I said that day are the same messages I still hold true of like, we are so much more than the way we look, and we are so much more than this meat suit that is housing our soul and this life. And we are so done with withholding all of that because we believe that how we look impacts everything else.
And so it was fascinating. But if you ever find yourself in a moment like that, I think it can also be really hard because you’re like, do they just want me to talk about this one thing over and over and over again? That’s not a business, that’s not a model, and that’s not what I do. And so it was really interesting to kind of reintroduce myself to my audience and say, okay, in case you’re new here, this is who I am. This is what I do. These are the things I believe, and you’re welcome to join me on this journey.
And so it’s still one of those things that we just laugh at in our lives. And now I tease that, I’m like, it’s Mrs. Six Pack because I’m coming for you, Drew Kutcher. And it’s just a beautiful to take people on that ride. But you’ve experienced it as well of who are these people and what do they want from me? And just staying in alignment with what you know do and who you are, and the right people will stay and the others will fall away.
Tori Dunlap:
Jenna, thank you for your time. Thank you for your work. Thank you for your friendship. Where can people find more about you?
Jenna Kutcher:
Oh, thanks for having me. So everything is at jennakutcher.com. It is the hub of all the things, my online courses, my podcast, my blog. My podcast is the Gold Digger Podcast. So if you love Tori’s show, I would invite you to become Gold Diggers, G-O-A-L Digger, wherever you listen to your podcast.
If you want to start a podcast, I would love to teach you how to do that. I have an online course about it, and you can find that all at jennakutcher.com, Instagram, Jenna Kutcher, it’s all there. Spelt like Ashton, no relation.
Tori Dunlap:
Thanks for coming on.
Jenna Kutcher:
Thanks for having me.
Tori Dunlap:
Thank you so much to Jenna for joining us. You can listen to Gold Digger wherever you’re listening to podcasts right now. You can also buy her book, How Are You Really, any place you buy your books. And as always, it makes the good little companion with Financial Feminist the book.
Thank you as always for being here. Feel free to rate and subscribe and share this episode if it was impactful for you. We appreciate your support. As always, we are so thrilled that you’re here and that you continue to come back and listen to the show. And if you want more from Jenna or more information about anything we discussed in this episode, you could go to our show notes and we spend a lot of time making those really pretty and detailed so you can head on over there.
Thank you so much for being here. As always, financial feminists, have a kick week. We’ll talk to you later.
Thank you for listening to Financial Feminist, a Her First 100K podcast. Financial Feminist is hosted by me, Tori Dunlap, produced by Kristen Fields, associate Producer Tamisha Grant, researched by Ariel Johnson, audio and Video Engineering by Alyssa Midcalf, marketing and operations by Karina Patel, Amanda Leffew, Elizabeth McCumber, Masha Bakhmmetyeva, Taylor Chou, Kailyn Sprinkle, Sasha Bonar, Claire Kurronen, Daryl Ann Ingram, and Jenell Riesner. Promotional graphics by Mary Stratton, photography by Sarah Wolfe, and theme music by Jonah Cohen Sound.
A huge thanks to the entire Her First 100K team and community for supporting this show. For more information about Financial Feminist, Her First 100K, our guests and episode show notes, visit financialfeministpodcast.com.
Tori Dunlap
Tori Dunlap is an internationally-recognized money and career expert. After saving $100,000 at age 25, Tori quit her corporate job in marketing and founded Her First $100K to fight financial inequality by giving women actionable resources to better their money. She has helped over one million women negotiate salary, pay off debt, build savings, and invest.
Tori’s work has been featured on Good Morning America, the New York Times, BBC, TIME, PEOPLE, CNN, New York Magazine, Forbes, CNBC, BuzzFeed, and more.
With a dedicated following of almost 250,000 on Instagram and more than 1.6 million on TikTok —and multiple instances of her story going viral—Tori’s unique take on financial advice has made her the go-to voice for ambitious millennial women. CNBC called Tori “the voice of financial confidence for women.”
An honors graduate of the University of Portland, Tori currently lives in Seattle, where she enjoys eating fried chicken, going to barre classes, and attempting to naturally work John Mulaney bits into conversation.
