The Risk & Reward of Becoming an Entrepreneur | Jenna Kutcher

29 Mar 2026 · 12 min · 3 chapters

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In short

Jenna Kutcher discusses the risk and reward of entrepreneurship, starting before you feel ready, and treating ideas as experiments rather than “success vs failure.” She also connects identity change to growth, arguing that knowing what you don’t want can clarify your next move, and that side hustles can build toward full-time change.

Guest backgrounds

Jenna Kutcher is an entrepreneur and creator who built businesses through courses and a podcast, and later authored the book Make Money Easy. She also shares personal experience with pregnancy loss and grief.

Key claims

Launch without attaching money/deadlines; use your current job to fuel experiments; evolve even if it contradicts prior identity; waiting seasons should be worked through, not wasted.

Notable examples

Corporate job with a boss giving a five-year plan; trying senior portrait photography for one summer; moving from Duluth to Minnesota after grief work and intuition; pregnancy test immediately after moving; one-in-four women experience pregnancy loss.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Necessity of Entrepreneurship

0:45 to 4:52

Exploring how necessity can drive people to become entrepreneurs.

“because you and I weren't entrepreneurs.”

Identity and Change in Entrepreneurship

4:52 to 9:20

Discussing the importance of evolving identities and their impacts.

“And it'll give you this ability to not feel the desperation that makes us say yes to the wrong things or do things that were never meant for us.”

The Journey of Waiting and Growth

9:20 to 11:16

Understanding the significance of waiting seasons in life.

“When I first was pregnant with my first pregnancy, I was shooting 25 weddings a year.”
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Transcript

Automatic transcript. May contain errors.

0:00One sweet, melty bite of a Hershey's bar and suddenly I'm right back sitting on the front porch with my grandmother on a slow summer afternoon. She doesn't say much, just breaks the bar in half and hands me a piece. I open my mouth to say whatever a nine-year-old wants to say. And she replies with a low, shh, listen. So we sat there, listening. That was the first time I learned that quiet can feel full. Hershey's, it's your happy place. Hi, my name is Lewis Howes, and welcome to The Daily Motivation Show.

0:40I'm curious for people that aren't entrepreneurs, or that haven't done entrepreneurial things, because you and I weren't entrepreneurs. For me, I felt like it was out of necessity at the season of my life, even though I didn't feel like I wanted to become one. It was never like a desire, really. I was kind of forced into it, or there was a necessity to it. For those that maybe feel like they might have something they want to put out there and build, but they're scared. Should they just go for it? Should they test something first and try to get a few sales and something? What do you think is the best approach now in today's time?

1:10Jenna Kutcher:I sometimes don't necessarily know what I want, but I know what I don't want. Like when I was in corporate America, I sat down at a table just like this and my boss said, here's your five-year plan. They never once asked me, what do you want? What's your next move? Where do you want to go? And I wanted to go to corporate. Like I wanted to move back to Minnesota, be in Minneapolis. But here I was in a store, a glorified HR person that had to bring the garbage to the dumpster at the end of the night. Sometimes I think that people get really lost because they're like, well, yeah, if I knew what my passion was, I could go figure out a way to make money, but I don't even know what my passion is.

1:48Jenna Kutcher:Right. And sometimes I think knowing what you don't want is just as important as knowing what you do want. And sometimes it's an easier place to start with. Like, I don't want 10 vacation days a year. I don't want to work weekends and nights, you know? And so it's like trying to figure those things out. But the other piece of that is that we have to like start to be open in saying, I've changed. I'm evolving. Maybe I wanted this thing for a while, but now I want something different. It's like we get so attached to our identities that the thought of like saying, oh, I'm different. Or I know I said I wanted this, but it doesn't feel the way I thought it would.

2:24Jenna Kutcher:And so I want to pursue something different. It's like, there's this notion, Dr. Maya Shanker was on my podcast and she talks about identity for closure. And it's like the reason why you hold on to genes that don't fit you anymore, because you remember how you invested in them or the reason why you get the degree, even though three years into it, you know that you don't want to do the profession. It's this idea of like, so I got to make it worth something, but instead then we're wasting our future, right? And it's fascinating because even being here with you today, having a book coming out, you're seeing a changed mind.

2:56Yeah, you didn't want to do this. At all.

2:58Jenna Kutcher:I mean, you are the one person who truly witnessed how much I said I wouldn't do this. Yeah, you're like, just go launch a course and make a bunch more money and have less stress. Yeah. We are so afraid of changing and not just changing, which is scary and uncertain. We're afraid of people seeing us change. We're afraid of being like, I know I said this one thing, but I don't believe it anymore. And I think that change is like growth and evolution. And like, we're in this thing called life school where we are learning. And if we're not learning and evolving, like, what are we doing? We're missing this opportunity.

3:31Jenna Kutcher:But I would say for those people who are like, maybe I have this idea or whatever, do it as an experiment. Don't attach money to it. Don't attach deadlines. Look at how I wrote the book. Do it in a way that proves to yourself that one, you're capable of taking action, but in a way that doesn't necessarily paint things as like black and white success and failure. Look at everything as an experiment. I'm going to try this thing. All it's going to do is yield a result and that result is going to guide my next step. And I feel like nowadays it's like we have to like define, is this a success or is it a failure?

4:04Jenna Kutcher:No, no, no, no, no. I've done many things and failed. I've tried many different things and been like, oh, that was not like I did senior portraits one year. So I was like, I can make bank shooting seniors. I hated it. Did it for one summer? I was like, never again. Was it a failure? No way. It was just a point on the path that was guiding me forward. And the other part of that is that every single time I've tried something different, it's always been a side hustle. I have not abandoned the nine to five to jump all in on something. I've used the nine to five to fuel the other something. Then when I did courses, I used the courses to fuel the podcast.

4:41Jenna Kutcher:And when I did the podcast, you know, it's like they all pour into each other. And it's like we're so quick to neglect something because it wasn't the perfect fit when it's like that can propel you forward if you lean on it. And it'll give you this ability to not feel the desperation that makes us say yes to the wrong things or do things that were never meant for us. What was the biggest identity foreclosure you've had in the last few years? I think for me, Drew and I met in college in Wisconsin, lived in Wisconsin for over a decade, and moved back home to Duluth, Minnesota. And one, I never thought I'd move home.

5:17Jenna Kutcher:There was just something about it where it was like, people that are there are still doing the same things. Right. Still the same people. Different mindsets, stuck in a ways or whatever, yeah. I had this vision. After our second loss, I hired someone to help me unpack the grief because I skipped denial and went straight to anger after our second loss. So I just was like, what is wrong with me? Why is this happening? I was very public about our first loss and felt like there was purpose there. Yes, the second one, you were like, this is frustration and anger. Yeah, and I was like... I got the lesson already.

5:48I don't need this again.

5:49Jenna Kutcher:Right, and I was like praying to God, like, where is your redemption song? Because I want to, like, prove how great you are, and now you've let me down again, and, like, I don't even know where to go from here. And I hired this person to, like, help me unpack my grief, because I was like, I'm angry, I hate my body, I don't know what to do. And she, like, led me through this exercise. And we were, like, sitting together. And we would get on the phone once a week. And every time I wanted to, like, hit ignore. You know, like, I was just, like, didn't want to do the call. Didn't want to deal with it, yeah.

6:16Jenna Kutcher:Yeah, because I was just, like, I know this is going to suck. And we're, like, on the phone. And just, like, okay, we're going to do a little exercise. And I want for you to close your eyes and, like, breathe. So she's, like, having me breathe. And she's, like, I want for you to envision, like, the most vibrant version of yourself. like you are happy and energized and alive and it didn't just stop at like the vision she's like put your fingers in your finger slots like step into your feet like I want for you to be there and like feel what it feels to like be fully alive and to enjoy your life and she said this line and it was like like a dial on a stereo I want for you to turn your intuition up and turn the noise of the world down and I was like envisioning all this and in the vision I saw this little girl and pancakes and a Persian rug and I was wearing jeans and a white linen shirt and I opened my eyes after the vision I was like bawling she goes you know what came up for you and I was like I think we have to move and she was like what do you mean and I was like I love the house we're in but there's this bedroom and it was always going to be our baby's bedroom and I'm like every time I walk by it I just think about what hasn't happened yeah I was like I just this vision of like this long table and like this rug and this baby and like i see it i was like i think we've got to move that day because i'm a quick action taker you're like looking at houses you're like literally fighting an agent i get on zillow and i type in duluth minnesota and drew and i had never talked about moving home like it was like maybe we'll move to minneapolis someday and i found this house on zillow and i text my family text thread as a joke and say maybe this will be the Kutcher craftsman.

8:01Jenna Kutcher:Like it was this beautiful home in Minnesota. We had never talked about it. Drew was out on a run and his phone starts blowing up because my family's like, move home, move home, come home. He's like, what? We never talked about this. Yeah. He gets home. He's like, what is going on in your family text thread? Like it's going crazy. And I was like, did you see the listing? He's like, what listing? And I was like, saw this house in Minnesota. And I thought he would be like, you know, maybe three years from now. And he's like, oh, we can do that. You know, It's crazy because I didn't necessarily move because of the vision, but it was the first thing where I was like, where we are is not working for me.

8:35Jenna Kutcher:The craziest part is this, Louis. We didn't move for seven, eight months. The day after we moved in, I took a positive pregnancy test. I always say, it's like I had to move home and be grounded at home. It just felt like this crazy moment where it was like, I'm home and I'm ready and this is it. And that next day you moved in. That's crazy. And here's the thing that's so wild about my journey, because one in four women experiences pregnancy loss. When you're in it, I mean, it is dark. I can imagine. Our, like, three-year waiting season, I can see now with hindsight, was required for me to build a life that supported what I was waiting for.

9:20Jenna Kutcher:When I first was pregnant with my first pregnancy, I was shooting 25 weddings a year. I remember we were in Hawaii and I looked up the due date and I was like, I can't be due then. I have like four more weddings. I mean, I like have to cancel on these. Like I literally was like. It's like you were sabotaging your body. It was like I didn't know how I would do it. You know what I mean? Your body's like, we're not going to let you do it then. Yeah, like it's crazy. And then the second time around was a huge wake up call because I found out that I had lost the baby, but my body was still pregnant.

9:52Jenna Kutcher:and I had to show up and shoot a wedding the next day. And so I had to pretend like I was the happy wedding photographer. And so when I look at those losses, they were massive teachers in my life. But by the time I was pregnant for the third time, I had built a life where I was able to move and I wasn't tied to anything and I had no clients to answer to and I had built that. And so there's this quote that I heard from a preacher and it's like sometimes the season of waiting is just as important as what it is that we're waiting for. I think a lot of people find themselves in seasons of waiting and it's really easy to want to like twiddle your thumbs and just sit there, right?

10:34Jenna Kutcher:But I think we waste it. And it's like, I worked while I waited and I don't mean like I hustled. I worked towards the life I wanted for when the time came. And it was so evident when it happened.

10:52I have a brand new book called Make Money Easy. And if you're looking to create more financial freedom in your life, you want abundance in your life, and you want to stop making money hard in your life, but you want to make it easier, you want to make it flow, you want to feel abundant, then make sure to go to makemoneyeasybook.com right now and get yourself a copy. I really think this is going to help you transform your relationship with money. this moment moving forward. We have some big guests and content coming up. Make sure you're following and stay tuned to this episode of The Daily Motivation Show.

11:33Thank you so much for listening to today's episode of The Daily Motivation, and I hope you have an amazing rest of your day. If you enjoyed this episode, make sure to click the link in the description. That will take you to the full episode of our main podcast on the School of Greatness. And if you are loving the daily motivation, please follow us over on Apple Podcasts and Spotify and leave us a review over on Apple Podcasts right now. And if you want more exclusive content and ad-free listening experience, make sure to subscribe to our Greatness Plus channel on Apple Podcasts right now. And if you wanna get even more inspiration from our world-class guests and learn how to improve your life and take it to the next level, then make sure to sign up for the Greatness newsletter and get it delivered right to your inbox over at greatness.com slash newsletter.

12:23Again, have an amazing day, and I'll see you tomorrow with another episode of the Daily Motivation Show.

12:35One sweet, melty bite of a Hershey's bar, and suddenly I'm right back sitting on the front porch with my grandmother on a slow summer afternoon. She doesn't say much, just breaks the bar in half and hands me a piece. I open my mouth to say whatever a nine-year-old wants to say. And she replies with a low, shh, listen. So we sat there, listening. That was the first time I learned that quiet can feel full. Hershey's, it's your happy place.

From the publisher

Leave an Amazon Rating or Review for my New York Times Bestselling book, Make Money Easy!

Check out the full episode: https://greatness.lnk.to/1271DM

Jenna Kutcher shares her personal experiences, highlighting the importance of taking calculated risks, embracing vulnerability, and maintaining a resilient mindset in the world of business. This episode offers invaluable insights into the entrepreneurial path and inspires listeners to pursue their dreams with determination and a willingness to face challenges head-on.

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