Welcome to Raise It Up with me, Danny Kagan, entrepreneur, mom of two, and your host. This is a place for real, unfiltered conversations about growth with ambitious women, mothers, and entrepreneurs who are building businesses while raising families. Together, we're redefining what peak performance looks like, and reshaping modern motherhood. From parenting and personal growth to business and beyond. Let's dive in with practical insights, empowering takeaways, and inspiring conversations. I'm excited that you're here. Let's go. If you're an entrepreneur, you know how hard it is to find real marketing support. I want to share the concept agency with you. They built my website and my Maven Shay website, my brand, and we've loved working with them. They are true marketing partners who actually support your growth, not just your to-do list. Check it out in the show notes. The concept agency, welcome to the podcast. This is a very, very special episode because it's my first live.
I heard it's your first like in person, which is way more intimate than a Zoom call because we all do too many Zoom calls. It's like hard for us to watch another Zoom call, but this is very real.
And this is very special because we're in Vancouver together at the same time.
Yeah. We just did an amazing brunch together and Danny and I both just had babies that are three weeks apart and so we said, 'Look, if we're away for the babies for one day, we better get this all done now.'
We're getting it done now. We're maximizing. Michelle was like, 'We're doing it now.' And I was like, 'You're right. We're doing this now.' No better time than the moment. Yes. Thank you for being here.
Thank you. This is so cool because I feel like so many people are itching to know about mom life, about this new chapter, and where you're headed next, what's going on. And also just like the advice you give to entrepreneurs and women and business owners generally is like gold. And I want to give that to all of my listeners today. So let's go.
Okay. So, I asked you this earlier today and I want to dive in a little bit deeper and I feel like it's a really helpful conversation to start with, which is what are some of those difficulties that you had starting out versus difficulties now at the top?
The real honest answer and the one that no one wants to hear is there's just as many challenges at the start as there are when you're a $100 million company or really big. They're just very different. And so instead of thinking about do the challenges go away, which I mentally told myself all the time to keep going. I was like just get here, we'll get better. Just get here. I think you have to embrace and lean into liking the challenge because at the beginning you're just like you just need a product to work. You just need product market fit. You just need a little bit of revenue there. It'll get better. First employee. It'll get better. Then you have like 100 employees and they're not fighting with each other. It's just like and then you know at $100 million it becomes very different because at least in our business at Clearco, we had created a category and then when we got big it was like we now had competitors competing with us, driving margins down effectively which happens in a lot of spaces. And so you have a very different set of challenges. And so instead of thinking about do the challenges get better or different or does it get better, think about it like I'm a person that loves challenges. I like being uncomfortable. If I had a life motto it would be never be comfortable because you only grow when you're a little bit uncomfortable. And so I think that that's so much of what I've been thinking about.
It's so great because I feel like I live in uncomfortable all the time. And it's like you have to take a second and take a step back and be like this is good. This is a good thing. This is what leads to exponential growth.
And I think that's just a really good reminder for everyone. Reminding yourself that it's only hard things that make you inevitably feel invincible. I still remember we had our first huge challenge in Buytopia. This was my startup in like 2010. We were one of the first e-commerce companies. We had a merchant that was nearly going bankrupt which is putting a lot of returns and pressure on us. Horrible situation. I remember not sleeping for like 4 weeks, waking up in cold sweats at 4 in the morning. I was like, 'We're going to lose our company. We're going to lose our whole team. We're going to lose everything.' And we got to the other end of it and I remember thinking like I was invincible. Like you quit, great, I'll find someone else. You just take these regular business life moment things. Deal doesn't close, great, we move on. All of those became so much easier because I was like I just worked through what I thought was almost losing my whole company, almost having to declare a personal bankruptcy. Like it was really bad at one point. And when you make it through that, you're like, I'll be fine. And then you're a great person to be around because you're way more chill. Way less anxiety that's wearing on everyone else.
It's like you almost need that moment like that. I am so deep in the depths and I am going to quit and this is all going to erupt that when you make it on the other side of course you almost need that moment so that you can be like life is okay. I'm going to live. I'm going to thrive.
What are some of the things that you look for in great founders?
I think that there's a couple of things. The first is that the trait I look for in founders is that same level of resilience and can just every day get up, go in the boxing ring, get punched in the face, and then be like, I'm ready to go tomorrow with the same amount of enthusiasm.
But how do you know that when you just meet someone and they're pitching to you?
Because you're seeing how many struggles they've been through in their life personally. You're seeing how many iterations they brought through their company. Almost no one is successful on their first idea. You have to do lots of different ideas. I mean Clearco was like we funded Uber drivers, we funded Airbnb hosts, we didn't even get to this e-commerce thing until like 2 and a half years into the business. These take a really long time to build and that's true of many of the largest companies. And so you want to see someone that's had those struggles. I think people that have also had struggles in their personal life and made it on the other side of that, it's a lot to live through just some of the things that life throws you. And so when people can be really resilient, and then you just need someone who is constantly on, constantly getting shit done, constantly responsive, thinking about things, making fast decisions because innovation comes from iteration. It comes from trying a lot of things. And so if you're dwelling on the past, if you're not iterating fast enough, you'll never figure it out.
With that said, what's a moment for you personally where you can look back and be like, 'Oh, this was a moment where I realized I'm actually really cut out for this.'
I think I just felt joy in certain things that I was doing and there were these moments. You have to get really excited about breaking an old existing industry. In yours, you're like, why hasn't there been orthopedic slippers? How have we just missed this entire category? And it could be anything. I remember we had an early AI business that digitized a lot of couponing back in like 2013. We sold this company to Groupon in 2014. It was like early machine learning. It's pretty wild now thinking back on it. I was just so excited because this is so archaic. Coupons like physical coupons are counted in garbage bags and they're shipped to this place on the east coast in like Newfoundland and some dude counts the coupons and does a manual tally. I was like, 'This has to be broken.' Obviously that's not the most glamorous industry to be disrupting, but the excitement of changing things over has to get you excited. I actually still remember we were like 2 years into Clearco. And we were one of the first big companies that had done a large amount of credit for founders without personal guarantees. This is a big deal because if you take a loan with a personal guarantee, if the company doesn't pay it back, they literally go after your house and your life savings. It's extremely punitive.
It should be really scary because they have a lot of leverage over you. And so we said, 'Look, we'll fund these businesses without personal guarantees.' I still remember the day that Amex launched their first credit card product that didn't have a personal guarantee. And I was like, we did this. We got a Fortune 50 company to copy us because we had introduced something else to the market. There's lots of downfalls of capitalism, but one of the great parts is people have to compete when you release something better. They have to respond. So I think if you like that, it's really good. So you got to look for people that are really resilient and then you got to look for really good business models.
I want to go back to the first thing you said when you answered this, which was you have to find joy.
Yeah. And I really feel like a lot of people are just after the end goal, but there is no end. There is no end. The limit does not exist. And it's just such a great reminder for all of us to be like you have to find the joy and if it's not feeling joyful, it's okay. You have to just do something else because you have one life.
Yeah, for sure. I want to talk about the fact that you just became a mom.
Yeah. Thank you. Our kids are the same age, which is pretty much the coolest thing ever. Sasha was three weeks ahead of yours, which is amazing. So, it's been very fun. Danny also does really nice check-ins where she just texts me. She's like, 'Just seeing if you're okay.'
I didn't eat at that point. You're like, 'Are you still have a pulse? Are you okay? Are you alive?' I felt like with my first and I was one of the first of my friends to have a baby, we were so lucky that we could check in with each other but I was like if I didn't have that, no one was checking in with me. And they always just asked about the baby.
Well they always asked about the baby and I also think things have really generationally shifted because I'm almost 40 when I had a baby. Most people historically had a baby when they were 20. So you were 20 years apart from your mom. So your mom could still remember what that is. 40 years is a lot to remember what it's like having a newborn. And so I think that dynamic has also really shifted.
Well, my mom had me at 40 as well.
Oh, really? Okay. It's amazing. And I think there's a lot of beauty in being an older mom.
Oh, you're so much less anxious.
Yeah, I'm sure you are. You're so much less anxious, I think.
Yeah. And you also know who you are right now.
Of course. And I feel like I have no... I'm always one of those people that I would have been happy if I had kids, if I didn't have kids, but I wasn't dying to have kids. And now I think it's the best thing ever. Obviously, you get bought in pretty fast. What's your favorite thing right now about being a mom? And then I also want to understand how are you doing everything you're doing and being a mom? Because I think for all of us entrepreneurs that don't really get the mat leave and are choosing not to do that, we're looking at people like you and we're like if Michelle can do it, I can do it.
But yeah, what's your favorite part about being a mom right now?
It's just like a really magical... it's magical to have something grow inside you. I had a really cool doctor deliver Sasha and at the end her head was out, her shoulders out. He's like, 'Put your hands out.' And I'm like, 'What?' Like, 'Put my hands out.' And I actually pulled her out of me which was one of the most mind-blowing, beautiful things ever.
You're so brave, by the way, because my doctor did the same thing with my first and I was like, 'Just get her out.' You're like, 'Wait a second. You're the expert in this. I am not the expert in this.' But I look back and I'm like, 'I should have done that.' That is so cool.
It's really cool. It literally makes me cry thinking about it. I don't know. I think there's just unlimited joy with these kids. You walk into their rooms after they've slept and you're like, 'Hello.' It's like really cool.
I know. I love that you're getting emotional about it because it is the little giggles. And look, all of this changes. I've also mentored and had so many people in my life that have to go through all the years of parenthood and these messy teenage years and the messy years where your kids are not doing what you want them to do. I don't think this is one of these things where having a child is like having a puppy. They're not an unlimited love thing. I think they're an unlimited thing that you have to mentor and there's going to be moments where I'm sure you will be very frustrated with them. But anyway, it's great being a mom. I don't have any... I'm also 6 months in. I have no perfect formula on how to do that. I think I have an incredibly supportive partner. Supportive family. I have a nanny that's been amazing. And then the biggest thing is I want to spend all of my time with Sasha. And so I just have to be very organized when she does go to bed and when there is time off. And it's kind of like what we did here. It was like I was like look we have one day I'm off. This is done. Let's actually get it done because your ability to move things. I think you can get a lot done in business when you're just very clear this is what we need to achieve, this is what we're looking to do. And so it just helps you be that much more concise when you have a little bit less time.
Do you feel like you're actually more organized now because you have more on your plate like with Sasha?
Yeah, I think there's always been this line about if you want something done, ask the busiest person to do it. Work expands or contracts given the time you give it. So if you have an hour to draft a contract, it will take you an hour. If you have four days, it will take you four days. So you just have to jam it in and you have to be at at least one point in your career where you've really produced a lot of content and a lot of work. Content is the one word but like you just got a lot of stuff done and you kind of know what the limit is. I remember our limit at Clearco is we believed that there was four days in every day. There was a day before 10:30, there was a day before lunch, there was a day before 5:00, and a day before midnight. And if you could, you literally got a week in a day if you iterated fast enough and if you made those checkpoints fast enough. And so yeah, I can't do that because now Sasha is my every 2-hour activity. But I do know that if I have 2 hours uninterrupted, I can really get a lot of stuff done. And I think there's a really cool unwritten rule of cadence. And I always knew this with my own employees that had kids is like I could always call them after 8 because the kids were in bed and it was really quiet and they would literally talk to me until 11:00. They had all this time at night but I just like you couldn't call them during bedtime bath time. That was a no no because it's such a big and cute thing to be a part of. You want to be there for all those moments. But you know what? Look, I'm doing this in real time. I have a whole new level of appreciation for women and sisterhood and all of this because this is a very unique experience that even with the most supportive partner you do alone. It's your body. You have to give a lot to the baby. And no matter what kind of support you have, it's just the biology of it.
Yeah. You really only understand when you become a mom how much is on you.
Oh yeah. And talk to me about your journey with breastfeeding like we all do.
Oh my gosh, I've done it so far. Thank god. It was just... the pregnancy was easier than I thought. The breastfeeding was way harder than I thought. I just didn't appreciate that this is every 2 to 3 hours. It's a biological system. There's no hack for it. There's no like, oh, just sleep 8 hours and you'll be fine. If you sleep 10 hours, you're going to have a clogged duct and it's going to be a real big problem. So I don't think I was fully mentally prepared for that. As much as I love technology, a breast pump is not the same as a baby. There's nothing close to everything from the latch to the biofeedback of it to the hormone release of it. So I'm happy I checked it out and then you gave me some really good advice which is just make it to 3 months because it is truly so incredibly painful, at least it was for me, until you get to 3 months and then it gets a lot better.
Yeah. And I got that advice from someone else and I also pushed myself and both times it was really good after that. But until that time it was excruciating.
And you know what the other good piece of advice is? When things get really hard, no matter in what scenario, in what part of your business or your personal life, I always just am like I just keep buying myself time. I'm like Michelle just try for another two hours. Just try for another day. Just try for another day. I have gone in the hardest part of my business career. I remember I just bought myself one more day for 60 days. It was like every day I wanted to give up and I was like I'm going to fight for one more day. I'm going to fight for one more day and it's exactly like that. It was like a bit of this breastfeeding thing. It's like this is so hard and so miserable and so painful and I'm so sick doing this and I can't seem to... and then it was like one more day, one more day, one more day and then at some point it just got a lot easier and a lot less painful.
Please tell everyone how you were breastfeeding Sasha at one point. Oh my gosh.
She told me this earlier today and I cannot believe this woman.
Not everyone has painful breastfeeding.
No, not everyone does. There's whatever 5% of women who vomit their entire pregnancy and it's horrible. I had a friend that was 82 pounds, 92 pounds 6 months in and they couldn't do anything about it. They were tube feeding her at the hospital. She vomited. It was awful. You have 40 symptoms, choose five, and you have no relation to the 35 you don't have. And the five you have, they're so intense, you're like, 'Oh yeah, the heartburn.' And everyone knows about it. But there's women that have no heartburn. You're like, 'How is that possible? There's an entire baby pressing against your esophagus for 9 months.' It's crazy. It's absolutely ridiculous.
Yeah, it's crazy. Okay, but please go back and share how you were breastfeeding Sasha at one point because I can't believe the fact that you actually persevered and did it like this. I would have quit after 5 seconds of doing this.
Oh my gosh. So I filmed Dragons 2 and a half 3 months postpartum and studio. I don't know. It was just really hard. My partner was amazing and he really showed up to set and really helped and we had a nanny and it was just amazing. And so I'd literally walk off set and breastfeed her. She was sleeping. I couldn't pump. I would just do my very best. But then whatever happened, she just stopped wanting to latch the same way, which is really heartbreaking. Because you're like, 'Oh my god, what's wrong with me?' And so I kept reading ChatGPT. I kept saying you can get babies to relatch. I was like, 'Fuck it. I'm doing this. I'm figuring this out. I'm using every trick. I put a bottle in the breast pack in anyway.' Finally I figured out she would feed if she was lying down on the bed. And I literally planked over her. And so I basically just breastfed planking for a solid 4 months. And everyone thought this was so hilarious. Like what are you doing? I'm like getting stronger. I'm like, no, the only way she'll do this. This is so good for her. I'm making my best effort.
I did not realize you did that for 4 months. It's insanity.
I thought that was like a few weeks.
No, no, no, no. It was like a long time. And every time I'd be like, 'And now let's transition to the normal hold.' People talk about there's a hold this way, which is the classic picture. There's a football hold, which is their body this way. No one talks about the plank hold. You're going to write the next mommy book being like, 'No,'
Try the plank hold. You get a workout. You empty your boobs and the baby's relaxed on the ground.
She loved it. I mean, imagine eating like that normally. She's like, 'Oh, no.'
I feel like she would choke, but I guess that's every. She literally that was the only way she'd eat. She liked it right away. She'd fall asleep and then occasionally I could start like that and then I could roll it to our sides and I was like, 'Oh, thank God. Thank god I can stop the plank.' I feel like the sideline feeding has saved me with this one because she gets so distracted and she will like pull my nipple and rip it off and I'm like, 'We just got to be in a bed like teeth really early.' So we've had a lot of.
Does she have teeth already?
Oh, yeah. She has her bottom two and her top two teeth.
She got her bottom two teeth like at 3 months or something. Like three.
Oh, you're. She's already a powerhouse.
Yeah. Yeah. Oh, yeah. Like the nipping is very real.
Holy crap. My dual one of my doulas was like she. I was like, 'How's breastfeeding?' She's like, 'Well, if you look like a turtle chomping on your nipple 20 times a day.' And I was like, 'Oh, I'm not ready for this.'
Oh my god. I cannot believe that. That's crazy.
Anyway, if you can, you should do it because it's like one of those things that's just there so many benefits for the baby and it's just one of those things where you like fight it out and try and do the right thing.
Yeah. But it is so tied to entrepreneurship. It's like that.
I'm just going to do another day. I'm just going to get through today.
