Hot Smart Rich with Maggie Sellers Reum - Courtney Reum $210M BÉIS Exit, Canva's Employee Frustrations, Oura IPO & Talking Money in Relationships

Starting point is 00:00:00 I'm going to say something that could trigger a lot of people. I think women are better investors because we are witches. But actually, we do more diligence because every single move is being watched. So much more to lose. Exactly. And the only thing people need to understand about investing is... Today, I brought on my husband, who has started and invested in multiple billion dollar companies to help us navigate the biggest stories in business and consumer today. Canva told investors it was reducing its 2026 revenue forecast by 20%.

Starting point is 00:00:32 I want to dig into what we think is going on. Well? I promise if you listen to this episode, you will not only become hotter, smarter, richer, but you will go from passive consumer to business savvy and understand how to make the world around you work for you. The influencer investor is becoming mainstream. Like Alex Earle invests in symbiotica.

Starting point is 00:00:52 I like symbiotica. I don't think it's a great investment today. Why do you think that is? So let's get into it. Courtney Ream, are you ready to get hot, smart, rich? No one I'd rather get hot, smart, and rich with. Let's get into it. Okay, so we're going to have a little family office meeting today,

Starting point is 00:01:08 but we just spent so much time working remotely, traveling Europe. However, I did not post about anywhere but Santropay, I think, which was very interesting. I don't think it was super intentional, but then once I started not posting, I was like, well, I'm already not posting, so I'm going to as well not. But did you have a favorite part of our trip? She got back from Italy.

Starting point is 00:01:28 That was amazing. Being Lake Como together, your first time, place my parents loved. And since your parents and my parents all got married August 28th, it was such a nice way to honor them. So I'd like to clap on that post. I've been waiting for the invitation. You thought I missed it. So is the person who doesn't go on social media.

Starting point is 00:01:44 I would have, I would think I would have seen that one on my home screen, but maybe not. I feel like we did such a great job doing a differentiated experience this year. but I think it's interesting for people because we are working like an eight hour day, maybe even nine or ten hours some days, just at very different times. Like last night, even when we were flying here to London, we're working on the plane at 9.50 at night until 11. I was working in the black cab, but 11 something. I was going to be asleep. That was new for me before I started dating you where it's like you work from anywhere at any single hour of the day so you can enjoy your life. But I can honestly say that I think my fear.

Starting point is 00:02:23 or hesitation from posting away was like, I don't think that there is that nuance on social media right now where people can see you living your life, enjoying, and think that you're running a company that is growing and hiring people and doing the work that I actually am doing behind the scene. So I think I just kind of fell out of posting and it felt after a while a little bit nice. And then we just spent 10 days in Italy, which was incredible. I did post from there, which was good. I thought you did. Yeah, I was it from Vodeste, where we spent our one-year anniversary, and it's crazy we've been married for a year. Happy anniversary.

Starting point is 00:03:00 Happy anniversary. Thank you for coming on and doing that with me. I don't think I did the best job of what I wanted to do this summer, which was to be Duelipa, because I am Duelipa. Like, if I look at her life online and she's obviously one of the most celebrated and decorated music artists right now, she obviously works so much. But her life looks so much like play. That is what my life actually does look like. but I think there's such a misconception and you even heard me on certain calls this year of people being like, well, Maggie's still in Europe. And I'm like, yes, I'm still in Europe.

Starting point is 00:03:29 But I'm actually working from Europe and we have a base in London. We're going to and from. But I think because there's still such a misconception about working remotely and like being able to travel and still run a company, I felt this fear of like I'd just rather not post because I don't want people to get confused. Like how is Maggie running this company and being able to work from Europe? I think you just also get to a point where. you know what you're doing, very few people, other people do, and kind of who cares what other people say, I've had even business associates of mine this summer say to me, oh, some people are asking me what you're doing or this. And I'm like, that's of no concern to me. Because I know what I'm getting

Starting point is 00:04:07 done. I know what value I add. I know what is actually happening. And whether it's because I'm posting more or posting less or they wonder if I'm working, all that matters is what's, what, what's, you know, what the output is. I have one of my favorite things that I can't wait to put on a caption one day on Instagram and it's like I work hard to make it look easy because I feel like that's what Duelipa, who is a huge inspiration for me. Like I think about personal branding and like my aesthetic and some days it's hard being a Gemini because I'm so like I'm so optimistic and energetic and smiley and the other

Starting point is 00:04:41 days and like, well, I want to feel like my Scorpio moon and like very mysterious and very like you don't really know what I'm thinking. And so I think some days I get confused. with like how much I want to share, like, what my personal identity will be. But I think Duelipa does a really good job of like, she works so hard to make it look easy. And I think that is something that I strive for where it's like no one sees the work that's being done behind the scenes necessarily. But a lot of work is getting done to make it look like that.

Starting point is 00:05:11 The one thing I will say about this summer is it was really nice meeting so many people and they were always like, your husband is your biggest fan. Like he is constantly talking about your podcast, your show. And it's even evident with the shoes that you wore today. Like you wore red burgundy shoes as we switched the set back over. H.SR. APL line. So adorable. Thank you for being my biggest fan.

Starting point is 00:05:34 I'm very comfy. And my pleasure. Yeah. But for someone that just clicked into the conversation, they don't know you. They don't know our dynamic. What would you tell them to get them to stay today? I think I would say in a lot of ways, people might be surprised. I'm not that much different than your average listener.

Starting point is 00:05:47 I have no background entrepreneurship technically. I did work in finance, but that's very different than investing. And both just started from a real place of curiosity and wanting to create things. And through a lot of good fortune, meeting a lot of great people, I've been invested in, I think, over 15 unicorns, started several billion-dollar companies. And I think I've had a really good track record of trying to read consumer behavior and trends. So I hope someone listening goes, okay, this is what applies to me. and this can help me figure out where my unfair advantages are. And that's why I wanted to have our little family office meeting virtually today.

Starting point is 00:06:25 Okay. It's virtual or here in person? Well, everyone's watching virtually. More like a live stream. Yeah, a live stream of our family office meeting. I think the thing I love about our relationship is we have really intellectually stimulating conversations about what's going on in the world around us. So we're constantly looking at what the public markets are doing, what private companies

Starting point is 00:06:42 are doing, different leaders that we admire, different things that are being built. we're so in the entrepreneurial world that a lot of the time we gossip, as I like to say, about the trends and the behaviors and the people that are really pushing the world forward and that ultimately informs a lot of the decisions we make of what we're buying,

Starting point is 00:07:00 how we choose to spend our money, how we choose to spend our time. And so I thought that I would give a promise to the angels that listen to this conversation in full. They already know that they're going to get hotter, smarter, richer, especially since you're here. I knew there was a reason you asked me to wear my glasses today.

Starting point is 00:07:14 I know it's going to be like a live stream meeting, but yeah, I think I have to clean them at some point. Anyways, continue. I think that if the angels listen to this conversation in full, they will understand the biggest stories in the consumer and business world right now. They will transition from being a passive consumer to a potential investor. They will leave feeling more prepared to become an angel investor and a little tidbit on how to navigate finances with your partner, especially when there's a gap. So can you commit to that promise with me? Yes. And I would say people need to realize that even if you're not someone that's interested in consumer behavior, it affects everything in the

Starting point is 00:07:55 world we live in, even AI, which we might touch on. And I think now the way the world works, if you want to be a better investor, if you want to be a better employee, a better entrepreneur, you have to know what's going on in the world. You didn't have to know that 20 years ago and you have to know it now. So yes, let's commit to it. Actually, let's start there before we get into other stories that are that we've been talking about. How does someone get informed? Because I get that question a lot. Like, who should they be following? How should they be spending their time? What newsletters are they reading? So like if you had to pick the top pieces of advice or things that people can do right now to stay informed, what would it be other than listening to the podcast? Well, we talk a lot about

Starting point is 00:08:31 information diet. I think this is all attention economy. So you have to be really mindful of what, what you have coming in at you, what you, what you have pushed to you and what, you know, you kind of seek out. Tony Robbins says you're the average of the five people you spend the most time with, but you also are the average of like the things you consume, right? And so I do think, I think it's hard to give general advice so much as it depends on the industry and what you're interested in. But being informed is just a general thing. It doesn't matter what industry you're in, I'd say. I think that's why I'm so excited to get into the stories that we keep gossiping about today, because I think that that's one of the pivotal principles of our marriage and of our partnership

Starting point is 00:09:07 is these like intellectually stimulating conversations. And we have been talking about these behind closed doors. So let's just get into the first one. This one, we have not talked at length about the why. So I'm just going to lay out what, what happened. Then I want to dig into what we think is going on. Shea Mitchell just sold base, her luggage brand that had taken over pop culture, social media, especially the Gen Zia and the millennial travel consumer, specifically the female consumer. You have some of her luggage. Tons of it. I love it. The brand had delivered rapid profitable growth generating approximately $210 million of sales in 2025. It had attractive margins.

Starting point is 00:09:46 And in the press release announcing the acquisition by Samsonite Group, it was expected to further enhance their net sales growth profile. But what really we need to talk about as it relates to base being sold is that the numbers at first glance don't make sense to me. So according to the press release, The transaction's total enterprise value was $210 million on a cash-free debt-free basis. Samsonite would acquire 85% of base for $178.5 million. Shea would actually keep her 15% ownership stake.

Starting point is 00:10:27 And Beach House Group, which is the majority shareholder of base, the incubator, would sell its full 70% ownership stake as part of the transaction. Everyone's celebrating this acquisition, but to me, the thing that I'm still stuck on is this fast-growing brand that's keeping its CEO to retain leadership at the company. She's the CEO? No, there is another CEO named Adela Hussein Johnson. Okay. She is going to be continuing on. Shea is taking 15% of her equity. She's obviously cashing out 15% of it.

Starting point is 00:11:04 In another way, she's taking off half her equity. What is the real story about what's going on here? Because why would they sell the company for $210 million when that's how much revenue they're making? Yeah, I didn't know you were going to ask me this or else I would have asked the Beach House guys because I've known him a while. But I think a couple of things jump out in really simple terms. This business sold for basically one-time sales. I don't think I think all of your listeners are sharp enough to know one-time sales. Doesn't sound like a great outcome. I think very few businesses start with. the goal of selling for one-time sales or $200 million, you say, oh, I hope I sell for a billion, and if you sell for $200 million, you might be ecstatic to pay how much money you raised. What we don't know is how much money they had raised. I don't know that. Maybe it's disclosed.

Starting point is 00:11:49 One-time sales isn't great. I think things like hard goods, like a suitcase, is not going to trade for five-time sales, no matter how fast it's growing. But I would have thought it could easily gone for two, two and a half, depending what fast-growing means. I would guess, so Beach House, I would think, force the sale. We own 70 percent, so they could force the sale. And, you know, Beach House has started a lot of brands.

Starting point is 00:12:09 I don't keep up with it as much anymore. I'm not sure they've exited any others. They've done ones with other people like Shea. I think they might have wanted to put a win on the board. And even if it's not a home run or a grand slam, maybe it's a solid double, as I say, in baseball. And they wanted to reallocate the money. And so it could be that Beach House didn't see where it goes from here, meaning how you triple sales, even if it's still growing.

Starting point is 00:12:30 Conversely, well, I think there's also the fear of the companies that came before, right? Away was doing more revenue than that, I believe, and basically went to zero. You know, maybe we'll even talk about other companies today that are headed in the wrong direction. So I think Shea saying she's going to take off half her money, which I've done many times, is me saying, I still believe in it,

Starting point is 00:12:47 but I am going to hedge my bet and take off half. So to me, her taking off half is like a little bit of both. If she said, you know what, I don't want a dollar out of this, I want to roll all my equity, that would be a big statement. Her taking half off means it's good money, I'll take it, but I still believe in the upside. For a company like base, they start this company, they have this amazing luggage.

Starting point is 00:13:07 They want to raise money. Why is a valuation important and how do they decide what that is? I think valuation means different things in the beginning versus the end, right? In the beginning, it's a little bit of like finger in the wind, art and science. You say, oh, it's worth, we're going to raise $2 million at a $10 million valuation. Why? We have this great idea. Shea Mitchell's involved, whatever, whatever.

Starting point is 00:13:30 It's harder to justify it, yet it's also harder to not. it down because, again, if someone's a first-time entrepreneur versus a third time, usually you put a little premium, so all that. Validation at the end, aka what Samsonite, Samsonai, right, bought it for, that's the tricky part because I think what's hard about starting something like base, which seems to have done great, but I don't think a toy maker is going to buy a luggage. I don't think Procter & Gamble is going to buy luggage. So who buys luggage? Basically another luggage company, Ramona, Toomey, Samsonite. So your buyers are very limited. They know that. They don't trade it crazy multiples, so they have to be disciplined. And the only person that buys a

Starting point is 00:14:09 luggage brand, I think, is like a private equity firm. And my guess is, no matter how old base is done, they're not profitable enough that valuing it as a result of, you know, cash flow or something would we get anywhere near the 210? What happens when a celebrity incubates a brand with an incubator? Because looking at this, obviously Beach House group is the majority shareholder and ultimately has control. So to your point, they want to force a sale. And She may not have wanted that. She's like, I think that we could go and get X, Y, and Z. So for me, I think what we're about to see in the market is a lot of people being very thoughtful about how they actually incubate brands. Because to my knowledge, even something like Alex Earle and Real Activs, that was not through an incubation house

Starting point is 00:14:56 where they are pumping out six, seven, eight brands with different celebrities, where the celebrity owns anywhere from 15 to 30 percent. Not that Shea is just a face because I think she's very obviously involved operationally with her business. But ultimately, the question comes down to control. And you tell me this all the time, even about Hot Smart Rich. As we're bringing more people into the company, as we're hiring, as we're raising money, it's like how much control do you really have? How important is control for any business that is being built? Not just celebrity brands. super important because once you give away the equity, just assume it's never coming back, except for in very rare circumstances. So if I gave away 20% of the company, that's 20% that's

Starting point is 00:15:41 never coming back. So you do have to treat it like gold. But I do think it's generally the view of once you take the house's money, in this case, the house is an investor or venture capital from a beach house or whoever, you have to keep taking the house's money. So to put a bow on this, I think it's like, we don't know if they all agreed to a 10 million valuation to start or a 30 million valuation. My guess is it's closer to the latter. And then Shea realized that they need more money because almost all these things would need more money. So at that point, everyone's diluted. And so at that point, Beach House, I think, decided they wanted to take some chips off the table. And if they invested at 10 million valuation, still a really good outcome.

Starting point is 00:16:20 If they invested at a 30 million or the person who came in after them at 100 million, not a great outcome. My prediction, based on this news, is I think every celebrity is going to be much more skeptical about control and ownership and what it actually means if you're going to put your blood, sweat, and tears into something. Because this is something that she built for eight years. This is not something that she felt like less. Yeah. And so for me, seeing her retain equity in this business be able to take it to a new. ownership team and ultimately do what she believes she can do with this business, which is obviously take over the luxury travel space with luggage, I believe is going to be a prediction

Starting point is 00:17:02 or what we are about to see with way more celebrity brands and teams where they're less focused on going to an incubator where they don't ultimately control the decisions and much more focused on building their teams internally and making sure that they actually can direct the company the way that they want to direct it. That is my prediction. I think you might very well be right. Okay, this is a little bit of a different direction because the last solo that I did, I talked about the power of being an employee and the power of being a corporate body.

Starting point is 00:17:31 And like, we didn't really touch on the equity side of things. But that's how I even started being an investor. Like, I started earning equity through companies that I worked at as part of my compensation package. And there is a large story in the news right now about Canva, who was kind of like the darling of Australia, especially, female founded. And they have had a rough August. The information just reported that Canva told investors it was reducing its 2026 revenue forecast by 20%. And days later, Blackbird and Airtree, two of Canva's longest standing backers cut their valuation by $7.1 billion, taking their mark from $42 billion to $34.9 billion.

Starting point is 00:18:12 And this has caused employees to get very upset about basically no longer being paper millionaires and actually trying to get some of the liquidity out of their equity that they have from being an employee. Yeah, it's tough because if you're an employee, I mean, we saw this with SpaceX, right? Even people who worked for the company for a long time, they're hanging on for that IPO. They're hanging on so that their shares vests and their lockups. And, you know, I know people on the inside who have, you know, one friend of mine who I think you've met has worked for SpaceX for 18 years.

Starting point is 00:18:43 You better believe he's been a loyal employee. But after 18 years, you want to see those shares vests and like have them be real money. Can employees put so much pressure on someone like Canva that they have to do some sort of transaction or have something that happens in the market, whether it's secondary or whether it is IPOing because people are so upset and so disgruntled? I don't think you can put pressure on someone to like sell or to IPO. That would be pretty extreme. But you can certainly put pressure on that they need to like refresh people's options or do a secondary sale and we see that all the time. So what do you think is going on with the employees at Canber today? You know, Australia is a great market.

Starting point is 00:19:22 I used to live in Australia before L.A. I have a lot of great friends there, friends of mine that you know, are friends with Melanie. I mean, she is the darling of Australia, as you said, the darling. I mean, I think by far the biggest venture back company from Australia that I'm aware of. Amazing. She's a female. Supposedly, she's a great person, the whole thing. But it can be isolating me in a place like Australia.

Starting point is 00:19:41 And you hear these stories of the U.S. Or you hear that, again, SpaceX created whatever it was, like thousands of millionaires. You're sitting there going, I've been here. working as an engineer in Australia forever, like, let's, and Australia is an expensive place for people who don't know and haven't visited, their morale can sink in a heartbeat. And you cannot have, you can have, of course, the disgruntled employee, but you can not have your engineering team, the backbone of Canva, be disgruntled, and that could be very well what's happening. And all of these people have been millionaires on paper. Is there any way for them to create leverage

Starting point is 00:20:15 by being a millionaire on paper, by taking their stock or their ownership in Canva and trying to do something else with it? Well, there's lots of ways now you can get liquidity if you're an employee at the company. Some of them are great. Some of them are less great. All of them involve usually a discount, right? So if I want to just go sell my shares in Canva and I was an employee, depending on how the contracts are written, sometimes you need the company's permission, which, of course,

Starting point is 00:20:39 they don't want to do if it's like a 30% discount to your valuation, it sets a bad precedent. but there's other times where you can go do whatever you want or, you know, there's companies now that will help you get a, buy a house against your shares and, you know, all those equations. So that's great, but you have to be really conservative with those. And then I think if there starts to be enough of a groundswell, someone like Canva goes, well, we're going to do a tender for secondary meaning we're going to let a bunch of early employees sell. I think the trickiest part is the people have joined Camvin the last couple years when the valuation

Starting point is 00:21:10 is already really high. I think the early person wants to either sell or get some liquidity because they've been around for a while and it's on paper. But the newer person is like, wait, I came in at $35 billion valuation. Then it went up to $42, which sounds pretty good. It's not a huge percentage increase, but it's a lot of dollars. And now you're telling me I'm actually underwater on my shares at $34.9 billion when I had my strike price at $35 billion valuation. Well, this is why valuations matter so much, right? Because it all depends on what you get in that and then where it's going to go.

Starting point is 00:21:40 And we're seeing so many of these companies, especially with AI, having reached such a high valuation at a certain point, not have a liquidity event. And then all of a sudden, things start dropping. Well, the trickiest part, too, is, you know, there's companies that I was in one that just sold to function, kind of one of these longevity companies. And they just got shares in function. And they said, well, our valuation is this. I said, I don't personally think your valuation is this because I think function is valued very highly. So if I think that valuation is overinflated, your shares might be worth a lot less than that. or at the very least, your fortunes are now tied to whatever happens with function because

Starting point is 00:22:14 that acquisition is a very small percentage of the function valuation. I get asked so many times like, I want to be an investor. I want to be an angel investor. And I always say the best way to practice is literally try to negotiate equity with your company as part of a comp package. Like if you are going to join a new company, practice diligenceing that company like you would practice investing because you're just trying to find answers to all of these questions of like, what is this worth?

Starting point is 00:22:41 What will this be worth in three years? And why try it with your own cash if you can try it with at least your time? Like the sweat equity of putting in the time somewhere. But I don't think that's like a huge mass market thinking for people when they're thinking about wealth creation. Do you believe that that is a real way to go from living paycheck to paycheck or a nine to five by actually earning equity in the companies that you work for and hopefully having an exit one day?

Starting point is 00:23:07 It really depends. what we found, what I found with companies I've started and invested in, I would say among like what I'll call kind of mid-level employees, almost half of them don't understand actually how they're, whatever they are, stock options or equity or phantom stock, whatever it is. They don't actually understand how it works. They don't actually understand how it appreciates. And we found that a lot of people, again, probably something like half, don't actually put that much value in it. Why? Because if you're not a senior executive making a bigger salary, and Sal called salary base plus bonus,

Starting point is 00:23:39 then you're still going, yeah, but having X amount of more in my pocket would help my lifestyle now, and that feels better than betting on something that might take 10 years or in Canvas case, there could be employees that were there even longer, and they haven't seen that.

Starting point is 00:23:52 So it is hard to ask people to put stock in that, pun intended, when you can't. It's not tangible, and you don't know the time. And it's not guaranteed. Do you think that it's changing now with names like Alex Earle

Starting point is 00:24:03 invest in symbiotica and all of these celebrities are starting to show the power of equity because I feel a different sense of the word angel investor today than I even did five years ago when I started doing this. Like there was a recent Vogue article that just came out about the influencer investor, which I was like shockingly not mentioned it. I'm going to say that out loud. I was like, I've literally been doing this for five years, been pioneering it on TikTok.

Starting point is 00:24:30 But I read the article and I was like, wow, it's so funny how now all of a sudden this is becoming mainstream. Like all of these influencers are talking about the power of ownership and the power of equity. And there's even companies that I've introduced you to like bullet pitch last night. I was talking about that company trying to bring creators to dinners and having founders pitch them. I do sense a market shift of the influencers that are starting to think that this is cool and starting to do this as a way to build their resume virtues. Ultimately, that's going to translate down to the mainstream consumer that's like, well, I also want to be getting equity into things. Do you feel like we are seeing a shift?

Starting point is 00:25:07 Earl is probably not hurting for money. So it's easy. And she's getting more equity than average employee. So I think it's pretty different. I think people should be valuing equity, but only when they've hit a certain number, whatever that is for them, or they're making sure they can cover their mortgage.

Starting point is 00:25:22 They're making sure that they're saving a little. But I think that's important. But I told, so I don't, maybe I don't think they're quite as correlated as you are because Alex Earls might be getting 5, 10, 30% of a company, an average employee is getting 0.5%. So it's hard for them to feel that. But I think the Alex Sertil's world and the influence, I totally agree, they want more equity. You know, going back 15 years,

Starting point is 00:25:46 when nobody was calling it creators or influencers or whatever, we had some different, you know, celebrities with some of our brands and we would talk to them. And I'll never forget when I talked to someone who you would know who was on a big TV show, Entourage, when that was a big hit. I went through, hey, here's what we're looking for. Here's what we're looking for. whatever, here's what we can offer, and I'm going through all the list of things we'd like. And this person, he just looks me straight in the eye and goes, whoa, that sounds like a lot of work. I just wanted to get some free booze. And I was like, oh, we're coming at this pretty differently. And there was a time where it could be, that's more like an endorsement deal, right?

Starting point is 00:26:22 Now it is about the ownership. It's about your name and everything else, but it's taking real ownership in these companies. And so that equity is exactly what you said now. Hot take incoming. Making more money as a creator doesn't actually require you to have more followers. I see so many creators getting this wrong. And this is part of the reason why I love what our show partner Stan is doing with their V2 of their funnels and order bumps. Because if someone is already buying from you, that's a completely different moment than someone casually watching your content. It means that they trust you, they're paying attention, they're already in checkout mode.

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Starting point is 00:28:19 or giving your business more flexibility, so if I can help you access the capital you need, so you can stay focused on running your business. Visit sophy.com slash HSR loan to learn more and see if the SOFI small business loan is right for your business. That's SOFI.com slash HSR loan. So I made that video about Alex Earle investing in symbiotica. It has over a million views, was reached out to by UTA, all of these agents.

Starting point is 00:28:50 Like, oh my God, this is amazing because we're seeing the mainstream consumer be super interested in the investing side of what Alex is doing. Why do you think that is? And that's where I feel like there is a disconnect, right? Because there's the consumer that's interested in this. They're like, well, I want to also do that. I got a DM from a girl yesterday being like, I'm so sick and tired of hearing about all these influencers that are going to be creating generational wealth. How do we do that? And I'm so curious if you see that bleeding into like even the public markets and people being more interested in financial wellness and like just their general portfolio diversification or you are saying people are just interested in making money today to cover basic expenses and they're not

Starting point is 00:29:31 thinking about wealth creation or creating generational wealth the way the creators are. I think it's a little bit of like Maslow's hierarchy until you've got like your basic needs met. You can't really think about these other things. And so Alex Earle's different than a main street consumer, but I think everyone wants to feel entrepreneur. Everyone wants to take those swings, but you just have to feel like you have enough of a nust egg to do that for sure. So I still think it's both, but I also think it can be a little bit of a dangerous thing to go, I've tried symbiotica. I love that product. Alex Earle's investment, therefore I should, because now we're throwing out all the principles we've already talked about, and we always talk about entry point.

Starting point is 00:30:13 you know, Alex Earl, we don't know what deal she got. She might have got a discount at the last round. She might have got advisors shares. The average person's not getting advisors shares in Symbiotica. And by the way, I like Symbiotica. I don't think it's a great investment today because the valuation's already really high. And if you look at where it can go, I don't think it can 10x from here personally. I think if it, for almost everyone is in Symbiotic, if it's two X is from here, everyone's super happy. I really like the product. I think one of my very first learnings, back to my Goldman Sachs days of working on things like Procter and Gamble Gillette's merger, Under Armour's IPO and things like that, is there is a difference between

Starting point is 00:30:48 a product that I like and that I consume and what makes a good investment. And sometimes they overlap, but you have to not confuse the two. And that's what can easily happen with Symbiotica and Alex Earl. You have some of my favorite principles of like first principle thinking in terms of like wanting to be an investor. We've talked a little bit about your food and beverage, delicious, nutritious, convenient. When you're thinking about first principles to look at any investment that you get across your desk, what are the things that no matter what deal it is in the CPG world or the consumer world, whether it's beauty, food and beverage, retail, what are those things you always

Starting point is 00:31:26 come back to? Of course, things like the founder. But it really is right idea, right context, and right timing. and I think I might have told you this just off-camera, so I'll share with everyone. I mean, in our real life. So I'll say it to everyone on camera. In our family meetings. In our family meetings that aren't live-streamed.

Starting point is 00:31:47 But is that there's a guy I don't really talk to me anymore but named Howard Morgan, legendary venture capitalist. Now I'm forgetting. I think first round capital, he's the founder up. He retires or semi-retires, but not really retires. He decides to look back on all his deals over 30 years and go, oh, I'm going to do this. And now maybe this was a few years ago, so it was before AI, so who knows. But he's doing it by hand.

Starting point is 00:32:09 He's doing regressions. He's saying this founder, he's trying to draw correlations and say, what would I have done differently? And what would I teach the next generation? And there's only one thing he came up with that statistically was significant enough that would have mattered. What do you think that thing is? Timing. Exactly. Timing.

Starting point is 00:32:29 That's the only thing he goes, wow. I had some right ideas but wrong timing. So timing means a couple things. It means I've had a couple of companies that I even started or invested in. And I was like, oh, you know, as you know, we're investors in Lyft. But we were investors in a company you never were heard of called Wheels with a Z and some other things that could have been the next Uber and Lyft. And they're actually too early for a lot of different reasons I won't go into. But we could do a whole case study on that.

Starting point is 00:32:53 But we were right around it going, okay, something's going to happen here. So we said timing. So timing means a couple things. One is, you know, even our first company we started, like an organic, better for-year vodka alternative with assay and other things that helped with hangovers, I think it was a little ahead of its time. You know, now with people drinking less, now would actually even be a better time. It was a good time.

Starting point is 00:33:13 This would be a better time. So it's that timing. And then timing also means the timing of your investment. And again, I love symbiotica. It's a great product. I try it. The timing is too late, I think. The timing is too late to really have that be something that,

Starting point is 00:33:27 creates generational wealth for you. It can be a nice investment. It's not going to change your life right now. Unless you get preferential terms, like I said in the video, that Alex probably did. Which Alex did. But we're talking to your, the normal consumer. We're talking to people listening to this. They're not getting any preferential terms, and they didn't see symbiotica when it was

Starting point is 00:33:45 just starting out in heroin. And that's a little bit of the key. It doesn't always have to be early. It's just why we talk about if there's one or two things I think I've been good at, one of them is just your Canadian. So we'll do the hockey analogy. seeing where the puck is going a little bit before everyone else. And I always say to people, I don't know.

Starting point is 00:34:01 I think a lot of times I'm like six months ahead. I don't know. Six months. I think in the world of AI, six months ahead is like your models ahead, your functionality ahead. So people understand it now. But six months ahead in trends can be really big. And so I think it's really important for that timing piece.

Starting point is 00:34:17 The way that I think about investing in my framework is like, I'm putting this capital at risk for what return. And like if the return is only going to be a one. a two, a three X, you could get a better return just in the public markets of investing in something a little bit more sure. But I think it's not even about getting a better return. It's about what risk did you take for? What risk?

Starting point is 00:34:36 This is what people need. This is the only thing people need to understand about investing. Private invest in public investing is what is the barbell or what is the teeter-totter of risk reward? Because people bring me something all the time and I'm like, and I'll say to them, no, it's a bad investment. They go, why? I think this will be a two. I'll double my money.

Starting point is 00:34:57 I think you're probably right. But I think you took, this could still go to zero. And you're hoping it could double your money, which is good. But you're taking the risk it goes to zero and that's still a very real risk. Whereas, let's say, you know, if you'd invest in Apple, I was just reading because there's a transition between Tim Cook and the new person. Very little chance that Apple goes to zero, but Apple could double too. In fact, during Tim Cook's tenure, Apple has like 10xed. So you got like a venture style return for very little risk, risk that it goes to zero.

Starting point is 00:35:32 Maybe it doesn't appreciate it. So a lot of times someone shows me something, I go, but I'll show you something that I think has the exact same chance to go to zero in my estimation, but could be 5x or 10x or maybe even 100x. So do you want to join me for that? Because there has a chance to be 100x, not a high chance, but a chance. And both the things, the thing you showed me in my thing, in my opinion, have the same chance to go to zero. Now it's all about the person procuring those odds, but that's what's important. investing is all about asymmetric risk reward and trying to find that. And timing is a big part of that to bring it all full circle.

Starting point is 00:36:04 So I feel like if anyone's going to get one thing from this conversation, if they're thinking about investing in their friends' companies, it's like what is the timing of that product and service in the market and what is the timing of your investment based on the value of the company today? Fair? Fair. So let's turn the combo to probably one of our favorite companies that we use every single day, an industry that we're both obsessed with.

Starting point is 00:36:27 Choms? Not choms, but close. How many choms did you have yesterday? Five. Okay. That's an everyday product. We love daily habits. I love daily habits.

Starting point is 00:36:37 Wearables are heading to Wall Street. According to the rumors, ORA is rumored to be going public, raising $3 billion for their IPO, potentially worth $16 billion. They would raise three valued at $16. Yeah. Okay. Is that seem fair?

Starting point is 00:36:55 I don't know why they raise quite so much an IPO, but meaning I just wouldn't take that much dilution. But Sean Brecker is the CFO who's a friend of mine because he's also the co-founder of Headspace that I invested in. He knows what he's doing. So anyways, if they can raise $3 billion, probably means they have big, big plans. What do you think about that?

Starting point is 00:37:13 Like, what does it signal for you? It signals that health and wellness and longevity and whatever term you want to use is alive and well. I think it means that it's coming to, the Main Street. You might have the stats there, but how many millions of people are wearing an aura ring? And I think it's great because I think it's just, even if you don't change what you're eating or change your sleep, this little thing will help you be more aware of it. And so I think it's great. I think all these, not all these, but many of these health companies are converging toward

Starting point is 00:37:42 the same thing. They just have different entry points. And whether you're Equinox Gym or ORA or one of our, you know, companies like Life Force, eventually you're also going off the same consumer, but you're building trust or having your hero product, your entry point at a different place. There's also an interesting conversation in pop culture right now about what is too optimized. And I think that we have a very healthy balance of letting data inform how we can better our lives. But you and I are not obsessed with it. I've always felt like knowledge is power. It's great to have the data.

Starting point is 00:38:15 If I feel good, I don't need a ring to verify what my sleep scores. And sometimes even it says I didn't have an amazing sleep. And I was like, but I feel great. So that's all that matters. But it's nice to have the data there as a leading or lagging indicator. And then once you have the data, you can always go back and, you know, have AI and other stuff analyze it. And do you think that society is moving to be too optimized right now with all of these wearables? And it will only become more so with or IPOing.

Starting point is 00:38:38 I think people are a little too into the biohacking optimization without doing the basics. Like get some sunshine. Have some relationships. Laugh. Walk around the city. Like all that stuff. That's the baseline that I still think is missing. versus spending your time indoors on a device, feeling lonely, scrolling, and reading about, you know, hanging upside down.

Starting point is 00:39:00 Like, those are not the, to your question about first principles, that is not the first principle. That's like the third principles. But I think for me, what I have become fascinated with and where I see a huge opportunity and we even spent a few nights ago at dinner with our friends talking about was the women's health story to this. because ORA has recently found a huge part of their ICP, their customer base with women that are either layering hormone tracking, pregnancy tracking, paramedopause, taking their temperatures. Fertility stuff. Fertility. Like for you and I even when we're thinking about, okay, we're trying to actively not get pregnant before we freeze our embryos, like I'm checking when I'm ovulating so you and I are not intimate with each other. And for me, I think what I'm excited about with ORA's IPO is the focus and hopefully trickle down a fact that this will have on women's health companies.

Starting point is 00:39:49 I know that sounds crazy, but I was even having a conversation with one of my founders that's in women's health, Laura. And she was saying it is still so hard to raise funding as a women's health company. Everyone says that they want to do it. But actually who is writing checks for people is a small number of venture capitalists. And I'm hopeful that whether it's ORA going public or even whoops, seeing their appeal to a much broader audience by broadening up their women's health, I'm hopeful that this is the sign to the market of the importance of women's health and how much more technology and how much more products need to be servicing that customer. Your point. ORA probably didn't think about this when they started. Or if they did, they said our technology is not there, but hopefully if we get, if we're successful enough 10 years down there, it will be.

Starting point is 00:40:36 and I don't know what the things have come out of aura specifically for men are, but you didn't name any. I don't know any. And everything else that I find interesting about HRV heart rate variability, that applies to men and women. So my guess is many more things have been the ripple effects of aura for women, which should be a sign that one, it's probably more complex. I forgot what you told me.

Starting point is 00:40:59 Your hormones change more in several hours around me than in my whole life. No, our hormones change more. a day than yours do in a month. For sure, and I see that. Don't cut this. I'm curious for you as someone who does invest, obviously, personally, also as a venture capitalist. Like, what is the level of diligence that the consumer can trust when a big VC splashes their name as like leading the series A? Like, are they diligently to that level? I think it really depends on the category, but I would love to see it higher as an industry. That's the truth. I mean, again, it really depends if it's a physical product, if it's an AI product that shipped,

Starting point is 00:41:39 if it's something a little more predictable, a little less predictable. But in the case of a shopping app, yeah, I think if you're leading the series A, but certainly like a series B, like if I was putting that money in it and it was like my money, I would be like, I want to come see the back end. I want to see how the flow goes. I want to like really get in there. And the truth is people don't do it enough. And I'm not saying we haven't been guilty of following someone or trusting that,

Starting point is 00:42:05 oh, this bigger firm who's been around for 30 years must do a diligence. But I think you've seen it recently with some of these companies that it's a lot of like, wait, I thought you were doing the deal. I just assumed that your people are doing it. And that's scary. And so forget investing. I think as a consumer, it is hard to do research on things like supplements, but even food and even apps like Yucca, where you scan the barricone and tells you if something's healthy.

Starting point is 00:42:28 It has its limitations, but it's about trying to do your best to triangulate that. You know, I was invested in a company called SUPCO that was doing the same. same thing for supplements. And I think they have some limitations, but overall, they're doing a good service in the sense that they're trying to prevent someone from going from something really bad, but it doesn't mean that everything that they've certified is exactly, no, but I think directionally it's good. But that's the part. People need to like be there. It's also like what is good for me and might not be good for you, right? It's the, it's the Socratic, like you should be able to be your own doctor after 30 and you have to figure out and do your own research,

Starting point is 00:43:02 but it is hard. I think, though, that's where they say that women statistically are better investors, only because I think that we feel we have to do so much more diligence because we have such a target on our back. I was on a phone call the other day in the car where I was like, I am held to a higher standard than other people in my space, whether it's because of my last name or the fact that I've raised money from Stephen Bartlett or whatever it is, I feel like my every single move is being watched and someone is just waiting to pull me down, right? And be like,

Starting point is 00:43:35 oh, look, she missed that. And so for me, when I look back, even I showed you my Mix Lab in deal memo, you're like, why did you make this deal memo at a seed stage when, like, you were investing 250k? That is a level of diligence that you probably didn't need to do. But the way that I've always thought about it is like, I have such a target on my back that I have so much more to lose. They're so far to fall if I'm not so thorough. And I think that's what's frustrating to me about the VMS of the supplement categories, I'm like, no one is able to trust these supplements because there's no FDA regulation. Like, there's no one that's actually keeping consumers safe.

Starting point is 00:44:14 And so for the consumer, they see, oh, well, this company just bought it or this company just led the series A, it must be safe. But I think what the story here is, is like, it's actually not enough to do that because so much of VC still today is like, oh, to your point, I thought you guys were doing the diligence about that you were. This brings on also even like governmental stuff that didn't use to matter. Depending on your view of RFK and Maha and all that, some people might think they can trust that things are recommending.

Starting point is 00:44:41 Some people might not. I'll let people opine on that. But it's it's all that, right? It's so hard to know and there's not a single source of truth and, you know, peptides are going crazy. If somebody watching this has like the, the killer. clinical thing and the research you would like to send me to convince me that peptides are a great thing and really effective and limited downside, please send it to me. I have not seen it.

Starting point is 00:45:11 No reputable doctor I know has seen it. Everyone's curious. Everyone's dabbling. Everyone's saying, hey, I think if you do a little of this and don't overdo this and cycle this and stack that, but it's all speculation right now. Something like GLP1s at least has a lot more research. It's early and whatever else and it all depends on the dose. But I think there's a lot more research on smaller dose of GLP1s than there is on any peptide. I think it's hard to be a consumer right now. It's hard to be an investor. It's hard to know because there's so much saturation in the world.

Starting point is 00:45:39 Like there's just so much. And that's where not to take it back to the beginning of this conversation, but like I really, this post really stuck with me. It was like the consumer that you want to reach is no longer spending time online. And it's a conversation that even Stephen and I had recently, which is like sovereignty and ownership and owning your audience. because we are slowly going to start to see people navigate away from social media. They are going to, whether it's prioritize their newsletters, prioritize in real life events,

Starting point is 00:46:08 trust word of mouth more. I saw this really funny thread this morning that was like, if you're thinking about marketing to your customer, think that you are in 1988. Like how would you reach that person? Because that is what it is going to start to become where it's like it's not about the best social campaign anymore. It's like how can you be in someone's mailbox? Like how can you surprise and delight people? If you're at a grocery store and your product, yeah, people look at their phones while we walk down the aisle, but I argue you're not really doing either well.

Starting point is 00:46:35 So it's like theoretically you'd be looking at your phone. And when you say online, I think you mostly mean social media. I take it to mean maybe they're on, you know, AI mode of Gemini or chat GBT or a private meta thing, whatever they're doing. I think they are doing that, but that's really different because it's theoretically not traceable and trackable. But your 1988 thing is like, okay, pretend I've actually been an adult and put my phone away. and I'm going through the grocery store and looking. It's this attention economy. That is a captive audience.

Starting point is 00:47:02 This product on the shelf, whoa, I never noticed that. What is that? Like, that is a moment of attention economy, but, like, that's the kind of marketing you need because in real life still matters. And I'm not looking at my phone. Love it. Okay.

Starting point is 00:47:16 We're not done. No, but I just love you. I love you do. Courtney, I had to ask the angels everything that they want to know from you. I picked three of the best questions or the ones that were submitted the most. So let's get into the questions from the Angels. The first one.

Starting point is 00:47:33 I hope these are good, because this is the only way I'm getting invited back. How did you approach your partner, making or having less money than you, when you were first dating and having to talk about money and finances? Well, I'll start by saying I don't remember exactly, but I remember that I think I probably could have approached it better, but I did my best. I don't know your view.

Starting point is 00:47:56 But I think, you know, you're a completely, competitive person, as I do believe, like comparison can be the thief of joy. And so I think part of it's just remembering, like, we are not the same people. We are not the same age. We're not at the same point in life comparing whatever you're doing, which is amazing to whatever I've done or haven't done isn't probably in a marriage, like a useful activity. You know, I am. Not everything that, you know, not everything that you can measure matters. And so for me, having a partner who's ambitious and wants to have impact, money can be. a part of that or it can be a resultant of that, I like that I don't think that you're guiding or gating thing. So I think bringing it up in a way that's like forthright, but also, I think it's, it's also like an iterative conversation because I don't care who you are. I think if I tried to explain you all my financial situation in one sitting, I think there's like managing directors of Goldman Sachs who won't follow it. I know there aren't because I've been with private wealth

Starting point is 00:48:56 managers who I've talked to about my own and they can't follow. So it's like I can't try to boil the ocean. I have to start to explain stuff to you. And then there's, you know, concepts to come into play that are part of our pre-nup, like, hey, here's something that has been valued by someone for some reason and somehow on paper. That is not what's in the bank. That may or may not happen. Here's what I have more higher confidence in a little will happen and all that.

Starting point is 00:49:20 So I think it just has to be like a layering and iterative thing. I think it has to feel like, I don't believe like everything has to be sure. it all at once. I mean, there's things you still maybe don't know, not because I'm trying to keep them from you, but it's just because, like, there's a lot of parts. And I'm like, when something comes up, I'm like, oh, wait, I probably never told you about that. Let me fill you in, right? If it's something big and meaningful, of course, but the long tail of things. I think it's just about being general, just are gentle and just kind of educating. What else? What did I miss? What do you think? I think coming at it from the partner that definitely did not have the same financial situation that you

Starting point is 00:49:59 had. Like I think that I was maybe worried about being embarrassed or being like, oh, is he going to think that I'm less than or that I'm not bringing as much to our relationship? And I think the way that, you know, you were even funny because you had watched a few of my TikTok videos and you thought, because I'm very masculine at work and I'm very like opinionated and go get her and direct and that's not necessarily how I am all the time at home. I'm still working on being a lot more soft, a lot more gentle, a lot more feminine, which you do a good job of allowing me to do. I can tell you that with previous relationships that didn't feel safe and secure, I approach those conversations with a guard up. I'm protecting myself. Whereas with you, I think the

Starting point is 00:50:43 environment that we created to first talking about money happened very organically because it was our fourth date. We were talking about my business because you were trying to help me. And I was like, I don't really make money in a bunch of different revenue streams right now. So as soon as I tell him the number that my business is doing, a lot of the money conversation, at least from my side, is going to come out pretty naturally. And I think what I tried to do was not approach the conversation of like, I'm this weak little person that is at a completely different level than you. I was like, I believe in my potential.

Starting point is 00:51:17 I believe in what I'm building. I'm reinvesting into my business. But here's where I'm at cash wise. Here are my constraints. here is what I have in my savings because I'm trying to grow this thing right now. And all I can say if you're the person that's coming at the relationship with definitely less money, less experience, it's not just about the number that's in your bank account. It's also about the life experience that you have, the potential that you have and don't

Starting point is 00:51:45 devalue those things because I think what I did was I didn't try to protect myself and put my guard up, but I also didn't try to be like, I don't have potential and I don't have a place to go. And I'm some weak person that's always going to be in this power dynamic that's not slowly closing the gap. Like not that I think that we're here now, but I do think when we started based on how I approached it, it started to feel a lot more equal, even though, of course, on paper, our financial situations were completely different. I think money's always going to be one of, if not the easiest scorecard or scoreboard. but it's certainly not the only one. It might not be the most important one. You definitely don't get to take it with you when you die,

Starting point is 00:52:29 so I think that's a big thing to think about, right? And making sure you knew where stuff is, what you would have, who to talk to, like once you decide this is your person, is really important. Hi, Angels. This is new, but also kind of not, because most of the guests that I had had on Hot Smart Rich

Starting point is 00:52:46 have been recommending one product in their top 10 every single week. And it is the eight sleep. So I was very curious. I had to get one. And then they became a sponsor of our show. And it makes sense now that I've been sleeping on it for a few months. It is a game changer. You guys know that I am obsessed with getting eight hours of sleep,

Starting point is 00:53:10 especially being a female entrepreneur. Why being a female entrepreneur? Because we have a different set of considerations than male entrepreneurs do. we have our hormones fluctuating, we go through so many different stages in one month period that having a mattress that can acclimatize to your temperature is key, especially if you have a partner that sleeps in your bed with you. For me, I'm complicated. I fall asleep when I'm freezing. I end up getting burning hot at night and then I wake up freezing again. So having a temperature controlled mattress like my eight sleep pod is.

Starting point is 00:53:50 critical. So I want you to try it for yourself at 8Sleep.com slash HSR and use code HSR for up to $350 off your order. I just asked all of you guys this one question. What is the one thing holding you and your team back from using AI properly? The answers were fascinating because everyone was basically circling the same problem, the same one that I had. They don't know where to start. People said things like, we don't know the right prompts. We don't know how to set up an AI agent. Our systems don't talk to each other. I think every company today needs someone thinking about this properly. How can AI save time or increase output? How can it make your business smarter with it replacing the human judgment that actually makes the work

Starting point is 00:54:35 really good and unique? That is where our sponsor, FiverPro, is so valuable because it connects you with vetted specialists who understand AI and more importantly understand how to turn it into a real outcome for your business. So instead of your team trying to figure it out alone, You can bring an expert talent who can move quickly, plug into what you're building, and help you use AI in a way that actually works. Visit pro.fiber.com to learn more. This one's very interesting. My friends are all starting to make more money than me, and I feel like I can't keep up with their lifestyle. How do I have that conversation with my friends?

Starting point is 00:55:12 Do you want to hear the first answer that came to me when I was free of these? I made a joke, and I was like, all I do with my friends now is go for a walk. first of all, because I think it's the easiest way to like catch up, do something active. You and I talked about this recently that like people are drinking way less and less. And for me, because I'm working so much or wanting to spend time with you, like the easiest and best way for me to spend time with my friends is legitimately going for a walk or finding an activity that isn't, I hate to say it, but like so much effort of like getting dressed up, putting on the things.

Starting point is 00:55:42 Like of course a girl's night is nice every once in a while. But if I had a girl's night twice a week, like I would just be exhausted. by that and wouldn't be able to handle it. And I think that's where when you once started spending $10 on a cocktail starts adding up to 18, that can accumulate really quickly when that's like constantly the activities that you're doing with your friends. So for me, I even remember this advice when I was suddenly the only single person in my relationships with my friends.

Starting point is 00:56:10 So when I broke off my engagement and I was the only single one, I remember my friend sitting me down and being like, I hate to tell you this, but you can't be friends with couple people anymore only, you need to go and make single girl friends because otherwise you're always going to feel left out. And although that really stung at the time, it was actually the best advice I've ever gotten from a friend because I did need to find single girlfriends to go out with, to have to have fun with, to go to the concert, to like not have to be like, check with your husband or check with your babysitter. Can you come out on a Friday night? And I think the same is kind of true with friends as you start to be making more money than each other. With those friends

Starting point is 00:56:45 that you want to keep, it's like find activities that are free or don't cost. a lot of money. I'm going to assume that the person who wrote that question isn't saying, oh, we're spending all our money on skydiving and like whatever else. And so if you're not someone that values adrenaline experiences or big trips or whatever else, I think part of it is maybe even taking stock of, hey, doesn't mean they're bad people, but if people are spending their money on this, on material things and that's not something I'm into, maybe it's a different friend group or sure is interesting to say to you, if you said to your friends really honestly that are they still your friends? Because if you can't tell your friend,

Starting point is 00:57:18 honest like, hey, that's a little too expensive for where I'm at budget-wise or what I want to do or how much I'm trying to save this year. I don't know. Maybe there are friends don't really care about you in the way where there are certain kind of friends, right? They're more of a party friend than a first call from jail or someone you call when you're upset sort of front. I think that was the thing that I had to learn when I became an entrepreneur was like, how do I categorize my friends? Who are my couch friends? Who are my girlfriends? Like going out girlfriends? Who are my couple friends and I think when you're in your 20s you have friends for usually those friends are for the same like they're they're across they're across the sphere of what you're going to have for a

Starting point is 00:57:56 friend when I did enter my 30s and my marriage became important my business became important my family my health became more important I started to have to categorize friends as to like are you a couch friend are you a walk friend are you a going out friend are you a business friend I think I've always done that because I've been like this is my workout buddy and this is the one that I watch sports with because he doesn't really work out. Or this is kind of my person I picked their brain on business. And there are those kind of Renaissance people who transcend them all, but it's very few. It's most people are a little more like, great. I love, I used to love going out with you, but we're not going to do business together, right? And it's just hard to be all things to all people.

Starting point is 00:58:36 Okay. Last question from the Angels. I started building a business and it's not going well. How do I know when it's time to quit something and start again? Yeah, this is a tough one. I think it's that, you know, to be an entrepreneur, you have to be an eternal optimist, but you also have to be a realist. And I think if I, like, got to spend five minutes interviewing this person, I'm not saying I would know the answer, but I think I could lead them to the answer. And my guess is the person who wrote this knows, but they just have to, like, prod themselves

Starting point is 00:59:12 or someone has to prod them a little because it's like, as I've always said, it's, you know, it's, you know, it's, thing about being an entrepreneur. microscope in one eye and a telescope in the other eye. They probably haven't even gotten to the telescope, like what's on the horizon. And maybe they're too focused on the microscope and you're like, oh, okay, these things that I thought were early hypotheses or not, or maybe it's like, if I could just get past this one little, as your business partner, Stephen calls it paper wall, all of a sudden it's like Christopher Columbus, like a whole new world, like I see the horizon. And that's what's just hard to say. I believe there's no one that's ever going to know how better than

Starting point is 00:59:49 the person who wrote this question and she just has to sit with a few things and just really try and see what's important. I would encourage that person to focus very little on things like dollars and cents and whatever else and focus on are the anecdotal signs there. Is it like, whoa, this is kind of crazy. Like I have almost no sales, but I have these like 100 rabid people who are loving my thing. That tells you something, right? I would be pretty encouraged. Or it's like, hey, I just, if it's something like, hey, I can't find the consumer, but the ones I have found are rabid, well, there's potential there, right? Like, you have a leaky bucket, you have a broken funnel. You need to figure out how to find this, this elusive customer, but the ones you have found

Starting point is 01:00:30 sure love it. And that's just like a matter of time and timing. And then other things you're like, yeah, I thought this would be better received and there's not, I create something that wasn't looking to be solved. I created something where there's already a better solution, whatever, is. It's hard to say. But I think I think that person knows. And then from a from kind of an emotional energetic point of view, Harvard professor of mine, Rob Kaplan, who also used to be the vice chair of Goldman Sachs when I was there, he said, we all overcomplicate it. It's like, this is your business. And you're thinking about like, like kill it or keep it. From an energetic emotional point of view, he said, it's just a house. The house is on fire. Is your first

Starting point is 01:01:12 thought? Run in there and save all the things. Grab as much. you can get all the people out, get the cats? Or do you sit there and go, yeah, I'm going to let that burn down and collect the insurance money, right? Like, it's that simple. I think that's what's so frustrating about the internet today is there's so much advice, and it's so contradictory because on the one hand, I hear advice that's like, if you knew that you were 99 rejections away from your dream situation, your dream business, whatever,

Starting point is 01:01:44 like, wouldn't you keep going? And so you hear that and you're like, yeah, I'm just going to keep going and like keep getting rejected and whatever. And then on the flip side, you're like, it's the complete opposite. Like there are some people's stories. And I even have a failed. The market has spoken. The market has spoken. Doesn't mean you're a worthless person.

Starting point is 01:01:58 It means the way you're presenting yourself, the way you're organizing this, the way, the things you're applying for. Or if it's a company, if 99 investors said no, it means you're just not organizing something, right? Because if 99 investors said no to Airbnb, it either means they're organizing it wrong or they're all missing it. And it could be the latter. But you still need the money to prove them wrong. But then imagine Airbnb just quits after the 99 rejection and doesn't get to the 100th. So it's like, how do you know which path that you're on? And I think because they saw something there when it was air bed and breakfast that somehow people were liking it.

Starting point is 01:02:31 Or they believed, I think they believe in a simple insight that no one believed that. Like, wait, I'm going to let a stranger into my house and stay there. Forget if they're giving me money or not. Like, I'm going to like in the early days. I'm not even going to lock my closet. My flannel shirts are in there. they're probably wearing one parade around the house. I'm going to let someone do that.

Starting point is 01:02:46 No way. No one's going to go for this. And if they haven't seen what's that movie, the holiday where you switch the houses. I think that seemed crazy. So that was avant-garde. But then they saw something else. Oh, this wasn't like a bed and breakfast thing.

Starting point is 01:02:58 This is like your home, maybe even your primary home, maybe a room in your house. I think they just saw it before other people. So it didn't matter the rejections. But I do think they changed how they repackaged it. But I think that's what's hard about the internet and giving advice is like you can see all these things.

Starting point is 01:03:12 my piece of advice is like when you're even listening to this conversation if you wrote that question in, you're going to feel one way or another based on the answer. Like if we say, yeah, shut it down and you get that gut instinct, we're like, no, I'm not shutting this down. Like, I have this thing here. I think that's your sign to keep going. Whereas if you're seeing the advice on the internet, that's like, no, you know, you're not finding your customer. It's not working. Shut it down. And you feel the sense of like, yeah, like I'm actually going to shut that down. That is what your Harvard professor is saying, where it's like, that gut instinct, that intuition that I fundamentally believe women have an advantage of because like we are witches. We have that intuition. We know things in our bones and in our gut.

Starting point is 01:03:53 That is what you listen to when the market does feel so confusing. And there's so much different information. But I think the way that your body reads it, the way that your body feels after you ingest something on the internet, I think that's why, you know, I think there's so much power of the internet. Like, I wouldn't be sitting here today with this business had I not started posting on TikTok. Like, I am not one of these people that is like, I think social media is bad. It's going away. However, I think that the new era of consumption of social media is going to be conscious consumption, the same way that I'm a conscious consumer in real life. I think as you're scrolling, instead of aimlessly letting things affect you, you have to really sit with yourself. Like, how do I feel

Starting point is 01:04:37 after consuming this piece of content. And if it makes you feel good, take that into consideration. It makes you feel bad. Make a different decision in your life. Like that is where I think the internet is going. Yeah. And I think of it, I think that's true. And I was just going to say, you know, in this group I've been in for 17 years called

Starting point is 01:04:55 YPO, which is the biggest worldwide CEO group, basically. There's a saying they have. The only vice is ad vice, meaning it's a peer-to-peer group. it's different, right? It's not me. It's not me as a five-time founder giving advice to a new person. It's like peers, so we're all like founders and CEOs. So it's saying like, I shouldn't say, Maggie, you should do this and do, blah, you start by saying things like in my experience or, oh, that reminds me of the time that in my 3PL trucking logistics business, I had something sounds like the recall of your food brand. And I think it's really helpful. It's different when it's a

Starting point is 01:05:31 peer situation. But I think what most people lose track of, and this is probably my final halfway a decent insight for the day is you are the CEO. Even if you don't have a business, you are the CEO of your own life. So don't just have things coming at you. It's not happening. Life is not happening to you. It's happening for you. The job of a CEO, black and white decisions are relatively easy. It's black and it's white. The hard part is the gray area. That is a CEO's job. But you're the CEO of your own life. You have to take in some of that gray area, whether stuff pushed you on Instagram or the things that AI is telling you, how many times do I, do you pull up sign AI and I go, I'm sorry, I'm not going to listen to AI. I'm going to listen to myself.

Starting point is 01:06:11 Part of that's that AI is not foolproof yet, maybe at some point, but part of it's that like I know something either in my gut or experience should be a different than a way to what AI is telling me. So I will continue to have views based on my experience in the gray area and being CEO of my own life. I just encourage everyone to take in this firestorm of everything assaulting you and just remember like you have. to discard what doesn't work for you. I said stuff today that might not work for 99% of your audience, but if 1% finds it useful, great. And maybe there's other things that are more relatable, but you have to decide what to adopt, what to let permeate you, what where your attention and

Starting point is 01:06:46 energy goes. Love you. Okay, we have to finish with just quick rapid fire like we do every episode. Okay. Okay. Courtney Rame, what is the last thing you put on our credit card? It's the last thing you put on our credit card was our laundry. are wash and fold. We've been moving around, wash and fold. Last thing, but a key thing. What is the last most expensive thing you put on our credit card? I think the last most expensive a pocket card was some really nice flowers for you

Starting point is 01:07:17 for a one-year wedding anniversary that I surprised you with. And I cried. I have a video of people. We'll post it online of her being surprised and crying. Her say, I need to go in the room. I got to pee. And next thing you know, she's crying. What is the current book you're reading?

Starting point is 01:07:31 One of my favorite authors, David Brooks, formerly the Atlantic New York Times, called How to Know a Person. Great book. He's written other books I love called Road to Character, where the line that I use, but I know you've used now is resume virtues versus eulgy virtues and what do you want to pursue at different points in your life. But this book, How to Know a Person, is really a good synthesis of a lot of his other books, so I'm loving it. Trying to make me a kinder, gentle, more empathetic person. Courtney Ream, thank you so much for coming on Hotsmer Rich. having a very intellectually stimulating conversation with me. We love you. And don't forget to comment on this episode because we want Courtney to come back and give us all of his plus one secrets of everything that you've been able to build and give to us. So we love you. And we'll see you

Starting point is 01:08:19 next time. I love HSR and all the angels. I just want to get invited back. So please.

Hot Smart Rich with Maggie Sellers Reum - Courtney Reum $210M BÉIS Exit, Canva's Employee Frustrations, Oura IPO & Talking Money in Relationships

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