The Five Lessons That Shook Me This Year

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3:09So I don't know about you guys, but when I listen to a podcast that I really love, I tend to go back again and listen for a second or even a third time because there'll always be something in there that either I loved and I want to double down on or something that I completely missed. Now, we've been doing this podcast for almost seven months. And so what I wanted to do was pull out some of the parts that have been the biggest game changers for me, the things that I've taken into my routine, the things that have shifted my way of thinking, and the things that really moved the needle for me. Because when I decided to do this podcast, it was really about sharing information, giving you an insider's look on how excellent people get stuff done.

3:49But it was also about finding more ways to connect with people and ultimately finding more ways to learn and to feed my own appetite to learn. So today I'm going to go back to some of my favorite episodes to show you the things that moved me the most. For me, there is no one more helpful when talking about business than Mark Cuban, because he ain't going to sugar coat it, but he's also never going to overcomplicate things. And sometimes a simple answer is all that's needed. So when I asked Mark, what's the one thing you wished every founder knew? He told me this, sales cures all. Meaning that you either have the sales or you don't have the sales.

4:29And therefore, one of the most important traits any entrepreneur can have is learning to sell. Now, listen carefully to this one because sometimes the best stuff is so simple, it just passes you by. This wasn't just a simple answer. It's the ultimate business truth because if you have sales, you'll figure everything else out. And if you don't, you don't have a business. You have a hobby. So thank you, Mark, for making it so simple. It's free visit. What's something that you wish every first time founder knew? Sales cures all. Sales cures all. No sales, no company. That's it. No exceptions to that rule.

5:05Because people get amored with all the other stuff, amored with their model, the marketing, and it's like, you need sales. I talk about this all the time. It's like, focus on distribution, focus on your sales, focus on like owning that story and just being the best salesperson possible because that's all you need at the end of the day. Right, because if you can sell. Yeah, you'll figure the rest out. Yes, because everything follows through to that sale. If you can't sell, it doesn't matter what you're good at. It doesn't matter anything else for that matter. You're stuck. Why do you think people avoid that?

5:38Because people don't like to be told no. Oh. You know, I tell people all the time, every no gets you closer to a yes. Every no, and I would tell that to myself. I was selling magazines door to door, right? And I'd walk up, are you telling me that for$5 a week, this wasn't going to improve the education and enjoyment of your family? No. Bye. On to the next one. And it's the same. Selling Mavs tickets. Switch up your pitch. You know, when I first bought the Mavs. Hey, it's less than McDonald's. No, you guys suck. Boom. On to the next. Right? You've just got to be relentless. And most people are afraid of the word no.

6:12Are you afraid to give the word no? Because I feel like getting the feedback is really hard. You just give the feedback, right? I don't like to say no to people. That's my problem. That's why I don't do hiring in my companies. Oh, is that true? Oh, yeah. Because I'm awful at hiring people. You're just like, come on board. No, I'm like, I'm a sales guy, right? So like, I think I can make this work. What is the truth then in entrepreneurship that no one actually tells you? The truth? Yeah, what's the truth? It's hard. You know, I think you're not automatically going to make money. most people don't make it.

6:49Most people fail. It's hard. Yeah. That's, I think, what I've seen. And it's interesting, actually, as you go into the tank, because even if you think an idea is a great one and you think it has a market, like not everything works out. No. And you can give the funding and it just for, I don't know, a myriad of reasons might not work. It fails. Yeah. Most companies fail. Have you failed? Yeah, of course I've failed. You never heard about my powdered milk company? No. When I started out of college? No. Yeah. Not a good one? Not a good one. It was cheaper. It didn't matter if it didn't taste. to like milk.

7:18It was powdered milk. All right. Tell me about the powdered milk company. I want to know about the failure. I want to know what it, what does it mean to fail and get back up and do it again? Like what is it in you that allows you to take the failure and it not be about you? Damon John says it's best. It's the power of broke. If you're broke, what else are you going to do? I mean, I was eating mustard and ketchup sandwiches. I was going to a bar with $5 buying one beer and eating all the fried mushrooms and the peanuts and whatever shit they offer. Broke is good. Broke is great for a period of your life.

7:52Yes. Right. Cause you learn. Yeah. Yeah. It's really true. But what have you learned? Do you feel like the failures that you've had, have they amounted to something that you've been able to see like as a pattern in your life or is it more just about the individual circumstance? Cause I feel like I could look at every failure I've had and I'm like basically the same thing. I don't know if it was basically the same thing other than maybe shit didn't sell, right? It's that. Powder milk. Yeah. It didn't sell. It did not sell. I remember taking samples to people, mixing up like, look, milk's expensive.

8:27We're broke, right? This save you money. It is some gravy shit. Mixing it up and try it and just seeing the look on their face. No, you can do about that. Point taken. You're like, I got it. But it's just you. Your taste in milk is different, right? All right. So how long? Because this is about a month. A month. Yeah, about a month. Yeah, but isn't that the thing? At least you didn't try to do that for a year. Because some people just don't know how to step away. It was like doing no sales. It was going nowhere, you know? I know, but people don't always hear that. Don't you think? You must deal with a lot of early stage founders that just don't read the signs.

9:03They don't see it. And I think it's really important to talk a bit about failure and to talk about when it's time to pack it in. You know, I never really thought of it that way, but you're right. You have to have a lot of self-awareness to be an entrepreneur. It's no secret that I love Michelle Obama. But what she left us with after her episode was more than just great, quotable Michelle moments for me. The biggest single takeout was this idea of there being these defined chapters in your life and bringing an awareness to the fact that life doesn't all need to be figured out in one day. For me, this was more than a little bit reassuring because as a highly ambitious person, I do find myself in a rush to get to the next big thing.

9:43Every now and again, I wonder why what I'm working on isn't happening faster, why I'm not seeing the results that I want right away or the sales that I want right away, or thinking like, why didn't this thing happen exactly as I'd intended? But Michelle made that all go away with just this very simple reflection. When I look at my life so far with the benefit of hindsight, I know that there've been chapters when all I've done is work. There've been chapters when, honestly, I haven't had as much work as I would have wanted. There've been seasons where everything I tried didn't have the desired effect or flat out just didn't work.

10:21But this idea of your life coming in chapters or in seasons is a really helpful framework, especially for those of us who need to make sacrifices, sacrifices that slow us down or when something stands in the way that you didn't choose, like losing your job, someone getting sick in the family. What I know for sure is that life will throw you curveballs because you can be in a season that quite frankly, isn't about you. It's about your kids. It's about somebody that needs something from you that takes precedent. But knowing that nothing is finite, we don't actually need all the things in the exact moment because there will be another moment.

10:55And allowing yourself to be at peace with the decisions that you sometimes have to make was so liberating. you know being a wife to the leader of the free world to you know your own you know your own career ambitions and all your own aspirations as well and I wonder if there is like a critical and honest piece of advice that you can give or that you can share based on your own journey and what you would say to women that are trying to seemingly have it all do it all live to the fullest. I've said this a lot. It's impossible to have it all. So stop with that. First of all, you can have it all over a period of time, but this impatience and this feeling of like, I've got to be, I've got to have the exact job at the top of the game.

11:50And I want to be the best mom to all to the, you know, I want to be there, be at all the stuff. And I want to look my best and be in my best shape and be emotionally in tune, la, la, la, la, la. And my marriage has got to be on point. Like it's, it doesn't, you can't do all of that. There are trade-offs and it's okay. You know, if we're blessed and we can take care of ourselves emotionally and physically, life is long and you can have chapters and you don't lose out because you, you know, you didn't read the whole book in one sitting. Each chapter can be really special. When my kids were little and I was sort of ready to drive in my career, but Barack was a state senator and then he ran for Congress and lost, and then he was a U.S.

12:44senator, he was away more than he was home. I got to a point where I said, I can't be in the highest driving point in my career life. I just can't. So I left running a nonprofit that I enjoyed running, but running a nonprofit is an all-consuming, and the nonprofit didn't have a lot of money, and I needed flexibility. Did you do it happily, or was there resentment there? There was a little resentment, but I was happy because I love my girls, and I love the time that I spent with them. And I felt more at peace with that decision because it was the right thing for them. And ultimately for me, because it gave me balance that I needed at that time.

13:36And I use myself as an example. I did that and it didn't stop my growth. It didn't, you know, I went on after that. I became an associate dean. I was the vice president and head of community outreach for the University of Chicago Hospitals. As the girls grew and I felt more secure, I started realigning myself. People don't realize they can take a little pause. Life doesn't really give you the feeling right now that you can just be like, hold please. That's right. For whatever reason. And you can, and you don't have to stop. Like I didn't stop. I thought about quitting completely. And then I got an opportunity to get a good job that I enjoyed in a flex situation.

14:20I negotiated flexibility for myself. I negotiated flexibility first that wasn't flexibility. It just was less pay. And I was irritated at that because I got half the salary and was still doing a full-time job. So I learned from that. I was like, never again. And I'm too much of a driver to ever get paid less. Right. So the next job I was like, pay the full salary, but give me hard blanch over my schedule. I will get the job done, but I'm picking up my kids from school. I'm going to the Halloween parade and I might not be here on Friday, but I'll be here when I need to be here. So pay me. All right.

14:59I learned that. So I would just say out there to women, it can come. And if you are choosing to drive, which that's a choice, then don't parent from guilt.

15:15At the end of each year, I often think about the moments that made me feel most connected to people, to places, and to the communities I've been lucky enough to experience. I remember a trip when my girlfriends booked a little place through Airbnb in a tiny little coastal town. And that host left a handwritten note with recommendations for local cafes and a weekend market. That note led us to some of the best coffee we'd ever had. And eventually to conversations with locals that shared stories about the town. It was a reminder that travel isn't just about seeing a new place. It's about feeling welcomed into a community, even if only for a short time.

15:51And that's what makes hosting through Airbnb so special. Hosting isn't just offering a property to stay in. It's inviting somebody into a neighborhood and the rhythms of everyday life. It's sharing a favorite bakery, a morning coffee spot, or the sunset view from a local park. It's giving guests a glimpse of what makes that corner of the world unique. Hosting also has a way of helping you see your own community differently. You might rediscover a market you haven't visited in years, or a holiday tradition that feels new again when it's shared with someone else. For so many, hosting a place through Airbnb has become a thoughtful experience in anticipating needs.

16:29Preparing a space isn't just about tidying up. It's about asking, what would a guest want after a long journey? Where's the coffee? Are the towels easy to find? Is the Wi-Fi password obvious? It's about removing friction, creating comfort, and viewing the stay from another person's perspective. And that kind of proactive problem solving, well, it translates everywhere in business, in friendships, and in daily life. It encourages noticing small details, thinking ahead, and anticipating needs that in ways make every interaction smoother and more meaningful. Because at its core, hosting through Airbnb is about connection.

17:08It's about creating a space where someone feels welcome, seen, and cared for, even if just for a weekend. and those moments, will they ripple outward? Guests carry stories of that community back to their own lives. So when someone considers hosting through Airbnb, they can think about the power of opening their home and community. Think about the young family visiting for the holidays, the solo traveler looking for grounding, the old friends reuniting in a familiar place. Think about the stories that begin with a simple welcome, because sometimes the most meaningful opportunities, well, they start with the simplest gesture, just opening a door.

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20:47It will probably go down as the most succinct message ever delivered on the show. But when And Melody Hobson said, you have to have a sense of urgency. You have to want to be great. To me, it was like, here's what separates the best from the rest. I've said it on many occasions that not everybody has to be ambitious. We don't all need to start businesses or want to be at the very top of our career. But if you do, there are a couple of non-negotiables. And a sense of urgency and how much you care are two of the most important traits of any successful person that I know. Now, when we hear stories about people that do things that should take five years in one year or should take five weeks in one week, there is no secret.

21:34You know, you simply cannot underestimate the importance of moving fast and a first mover's advantage. I've worked in fashion for most of my career and sweating the small stuff or caring the most, as Melody says, is what the best people in the business do. The ones that care about every component of how a product is made, every stitch, the lining and the trim package and the fabric and the construction, then how it's folded when it gets on the shop floor, how it's put in the bag, how it's packaged to the customer, the experience of unboxing and on and on and on. That, that is the difference between the best and the rest.

22:09There's just some stuff that you cannot argue about. If you want to be great, urgency and caring the most is a great place to start. so many people that are sitting there in a corporate career. And I do think to some degree, there is a blueprint for getting promoted, for moving through a job in the way that you have. So what do you tell people? I mean, because you're on an 11, do you need everybody else around you to be on an 11? And what is it that people need to do in order to be successful and to be promoted where they're at. Okay, this is going to sound strange, and I'm going to make it hopefully not sound not great, but it's how I think about it.

22:55My mom had six kids. She mothered us all differently. That's just a fact. No siblings have the same parents. No. That is a fact. It's a fact. In my group of people who work directly with me, I understand what they can do and how they can do it. John Rogers always used to tell me that the World Championship Chicago Bulls that won seven championships, he said, Dennis Rodman rebounds, Steve Kerr shoots threes, Michael is the greatest player of all time. You know, he would go through each player and he said, but each one is really important. Michael can't play without them. They can't win. So Dennis may be out at night, but everyone makes sure Dennis is on the court so that he can rebound for them.

23:43And he's like, so he doesn't have the same rules as everyone else. And so Melody, you figure it out that you get the best out of each person but everyone's not going to run the place. But what happens if your aspiration is to operate at the highest level? Like what are the non-negotiables do you think for people that want that type of career? What do they need to do? You must. and I mean this with serious intensity, I think you have to care a lot and have a sense of urgency. You have to have a sense of urgency. You have to want to be great. And if you want to, there's a, you know, I love that book by Jim Collins, Good to Great.

24:22And the first line of the book, good is the enemy of great. Good is the enemy of great. Plenty of people are happy with good. They say the worst student is the B plus student. Because the B plus student, I was like, it's fine. They were like, the C student aspires for something better. And the A student is just the A student. But the B plus student is, they live in that no man's land of it's fine. And so it's almost like the worst situation that you can be in. So if good is the enemy of great, I want the person who wants to be great. But understanding that differential between good and great is really hard.

25:00Do you think you can train people into that? Or do you think it has to come from somewhere within themselves? It has to be there. Yeah, some people just, you know, they come out of the wound with it. Some people don't, but that doesn't make them, they can still be very valuable. They're just going to be a certain kind of player. And that's what John said. He's like, there are going to be other people. They're just not going to run the place. So you think people have to just work really hard, want to be great, and they need to have a sense of urgency? I think they have to want to be great. Let's start with that.

25:28And, you know, some people have to work harder than others. So I remember going to school with geniuses at Princeton. They didn't have to work as hard as I did. They, you know, sort of like skimmed the page and got it. And I'm like writing notes and checking, you know, flashcards and doing the whole thing. But, you know, it came easier to them. Some things come easier to me. So I think it's just a function of you understanding yourself.