In short
Courtney Reum and her husband discuss business/consumer investing through recent headlines: Base’s $210M sale to Samsonite, Canva employee frustration after a 20% 2026 revenue forecast cut, influencer/creator investing (Alex Earl/Symbiotica), and the potential Oura IPO, plus how to think about diligence, valuation, and timing.
Guest backgrounds
Courtney Reum is a finance-trained investor/entrepreneur who says she’s invested in 15+ unicorns and has started several billion-dollar companies. She frames her expertise as reading consumer behavior and trends. Her husband is described as having started and invested in multiple billion-dollar companies.
Key claims
Celebrity/incubator brands often sell for “one-time sales” multiples because buyer options are limited (e.g., luggage buyers are mostly other luggage companies). Employee equity can drive morale and liquidity pressure, but companies can refresh options or run secondary tenders rather than being “forced” to IPO. Valuation and timing determine outcomes; liking a product isn’t the same as a good investment. For wearables/health, data helps but basics and women’s health are underfunded.
Notable examples
Base (Shay Mitchell) sold 85% to Samsonite for $178.5M; Canva forecast cut and backer mark-downs; Alex Earl investing in Symbiotica (valuation too high to 10X); Oura rumored IPO raising $3B at ~$16B valuation; SpaceX employee lockups/vesting.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOWomen as Better Investors
0:53 to 2:55
Exploration of why women might excel in investing and the pressures they face.
“Get more with Northwest Registered Agent at northwestregisteredagent.com slash hsrfree.”
Travel Experience and Personal Branding
2:55 to 4:33
Discussion on travel experiences and the impact of social media on personal branding.
“Being in Lake Como together, your first time, place my parents loved.”
Work-Life Balance and Perceptions
4:33 to 6:41
Examining the misconceptions of remote work and balancing personal and professional life.
“I don't think I did the best job of what I wanted to do this summer, which was to be Dua Lipa because I am Dua Lipa.”
The Importance of Being Informed
6:41 to 7:55
Discussing the need for staying informed and understanding consumer behavior.
“The one thing I will say about this summer is it was really nice meeting so many people.”
Navigating Financial Conversations with Partners
7:55 to 9:35
How to approach financial discussions with a partner, especially in relationships.
“Yeah, a live stream of our family office meeting.”
Analyzing Shay Mitchell's Base Acquisition
9:35 to 11:03
In-depth analysis of Shay Mitchell's luggage brand Base and its acquisition by Samsonite.
“You didn't have to know that 20 years ago and you have to know it now.”
Evaluating Company Valuation and Market Trends
11:03 to 14:00
Discussion on market trends, company valuations, and the implications of selling businesses.
“The brand had delivered rapid profitable growth, generating approximately$210 million of sales in 2025.”
Navigating Valuation and Control in Startups
14:00 to 18:50
Learn about the complexities of startup valuations and the importance of control for founders and investors.
“Conversely, well, I think there's also the fear of the companies that came before, right?”
Canva's Employee Equity Challenges
18:50 to 23:20
Explore the recent challenges faced by Canva employees concerning equity and company valuations.
“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 baddie.”
The Evolving Role of Influencers and Equity
23:20 to 27:42
Understand the shift in how influencers engage with equity and ownership in startups and brands.
“And they said, well, our valuation is this.”
Show all 25 chapters
Maximizing Revenue as a Creator
28:01 to 29:17
Learn how to optimize your sales funnel to increase revenue without more followers.
“Making more money as a creator doesn't actually require you to have more followers.”
Consumer Interest in Investment
30:04 to 35:58
Explore the disconnect between influencer investments and average consumers' financial aspirations.
“Ready to make anything online make sense?”
Timing in Investment Decisions
35:58 to 38:29
Understand the crucial role timing plays in making effective investment choices.
“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 you're Canadian, so we'll do the hockey analogy, seeing where the puck is going a little bit before everyone else.”
Oura IPO and Women's Health
38:29 to 42:00
Discuss the implications of Oura's IPO on the health and wellness market, especially for women.
“So let's turn the combo to probably one of our favorite companies that we use every single day.”
The Challenges of Funding in Women's Health
42:00 to 48:28
Learn about the difficulties women-led health startups face in fundraising and the impact of consumer diligence on investments.
“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.”
Navigating Money Conversations in Relationships
48:28 to 56:47
Discover effective strategies for discussing financial disparities with a partner and fostering an equitable dynamic.
“Because that is what it is going to start to become, where it's not about the best social campaign anymore.”
Navigating Money Conversations in Relationships
57:14 to 58:28
Discover effective strategies for discussing financial disparities with a partner and fostering an equitable dynamic.
“You think you know a browser, but Gemini and Chrome?”
Navigating Friendships and Finances
58:42 to 1:01:14
Discussion on managing friendships as income levels change and the importance of supportive social circles.
“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.”
Knowing When to Pivot in Business
1:01:14 to 1:03:42
Exploring how to evaluate when to persist or pivot in business based on market feedback.
“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?”
Intuition and Entrepreneurial Decision-Making
1:03:42 to 1:07:40
Emphasizing the importance of intuition in making business decisions amidst conflicting advice.
“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 over complicate it.”
Being the CEO of Your Life
1:07:40 to 1:09:41
Reflecting on personal agency and decision-making in life akin to running a business.
“It's not me as a five-time founder giving advice to a new person.”
Celebrating Anniversaries with Meaningful Gifts
1:10:01 to 1:10:51
Discover the emotional impact of thoughtful gifts in relationships.
“I think the last most expensive credit card was some really nice flowers for you for our one-year wedding anniversary that I surprised you with.”
Deep Conversations with Courtney Reum
1:10:51 to 1:11:09
Reflect on the value of intellectual discussions and insights.
“Courtney Ream, thank you so much for coming on Hot Smart Rich and having a very intellectually stimulating conversation with me.”
Deep Conversations with Courtney Reum
1:11:19 to 1:11:38
Reflect on the value of intellectual discussions and insights.
“So everything that relates to the creative, the name, the brand, the website, the vision board.”
The Love Story of Real Couples
1:12:15 to 1:12:36
Explore a unique love story narrated in an engaging way.
“This is the love story of real hinge couple Daniel and Roisin, written and read by me, Rufy Thorpe.”
Transcript
Automatic transcript. May contain errors.0:00If you're starting a business, there are certain things that are so fun to think about. Y 'all know I love a mood board, so everything that relates to the creative, the name, the brand, the website, the vision board. But then there are the things that make you pause and ask, am I even doing this correctly or do I even want to be doing this? Like forming your business, getting the right documents, keeping your personal information private. This is where our sponsor, Northwest Registered Agent, is so helpful. They're a one-stop shop for founders who want to launch and legitimize their business without turning it into a giant admin spiral.
0:33They help you form an LLC or a corporation, act as your registered agent, and give you tools like a business address, operating agreement, website, phone number, professional email, and free guides. They also have real corporate guides who know your local laws. Visit northwestregisteredagent.com slash hsrfree and start using free resources to build something amazing. Get more with Northwest Registered Agent at northwestregisteredagent.com slash hsrfree.
1:26Availability varies 18+. 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%. I wanna dig into what we think is going on.
2:04Well. 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. 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, but we just spent so much time working remotely, traveling Europe.
2:41However, I did not post about anywhere but Saint-Tropez, 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 might as well not. But did you have a favorite part of our trip? Just got back from Italy. That was amazing. Being in 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 collab on that post. I've been waiting for the invitation. I thought I missed it. Says the person who doesn't go on social media.
3:14I 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 10 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 950 at night until 11. I was working in the black cab at 11 something and then I'm falling 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.
3:50But I can honestly say that I think my fear 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 scenes. 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 posted from Villadeste where we spent our one year anniversary.
4:26And it's crazy. We've been married for a year. Happy anniversary. Happy anniversary. Thank you for coming on and doing this with me. I don't think I did the best job of what I wanted to do this summer, which was to be Dua Lipa because I am Dua Lipa. 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.
4:57And I'm like, yes, I'm still in Europe, 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 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 asking me what you're doing or this.
5:33And I'm like, that's of no concern to me because I know what I'm getting 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's, you know, what the output is. I have one of my favorite sayings 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 Dua Lipa, who was 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.
6:11And then other days I'm 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 Dua Lipa 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. The one thing I will say about this summer is it was really nice meeting so many people.
6:46And 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. That's our APL line. So adorable. Thank you for being my biggest fan. I'm very comfy. I'm 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.
7:17I have no background in 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, OK, 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.
7:54OK. 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 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.
8:25and that ultimately informs a lot of the decisions we make of what we're buying, 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. 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.
8:56They 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. 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 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.
9:35You 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 we've been talking about. how does someone get informed? Because I get that question a lot. Who should they be following? How should they be spending their time? What newsletters are they reading? So 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 information diet. I think this is all attention economy.
10:03So you have to be really mindful of what you have coming in at you, what you have pushed to you, and what 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 is these like intellectually stimulating conversations.
10:38And 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 happened. Then I want to dig into what we think is going on. Shay Mitchell just sold base, her luggage brand, that had taken over pop culture, social media, especially the Gen Z 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.
11:15And 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. 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.
12:07Everyone'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's another CEO named Adela Hussain Johnson. Okay. She is going to be continuing on. Shea is taking 15 % of her equity. She's obviously cashing out 15 % of it. Put it 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 them a while.
12:51But 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, maybe it's disclosed. One-time sales isn't great. I think things like hard goods, like a suitcase is not going to trade for five times sales, no matter how fast it's growing.
13:25But I would have thought it could have easily gone for two, two and a half, depending on what fast growing means. I would guess. So Beach House, I would think, forced the sale. We own 70 percent, so they could force the sale. And, you know, Beach House has started a lot of brands. 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 they say, in baseball. And they wanted to reallocate the money.
13:52And 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. 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. 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, 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.
14:23If 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. 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.
14:55Why? We have this great idea. Shane Mitchell's involved, whatever, whatever. It's harder to justify it, yet it's also harder to knock it down because, again, if someone's a first-time entrepreneur versus a third time, usually you put a little premium. So all that. Valuation at the end, aka what Samsonite, Samsonite, right? Bought it for. That's the tricky part because I think what's hard about starting something like Bass, 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.
15:32So your buyers are very limited. They know that. They don't trade at crazy multiples, so they have to be disciplined. And the only person that buys a luggage brand, I think, is like a private equity firm. And my guess is, no matter how well base is done, they're not profitable enough that valuing it as a result of cash flow or something would 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 Shay may not have wanted that.
16:08She'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 Earl and Real Actives, that was not through an incubation house where they are pumping out six, seven, eight brands with different celebrities, where the celebrity owns anywhere from 15 to 30%. Not that Shay is just a face, because I think she's very obviously involved operationally with her business. but ultimately the question comes down to control.
16:43And 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. It's 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 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 firm or beach house or whoever, you have to keep taking the house's money.
17:23So 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 a 10 million valuation, still a really good outcome. If they invested 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.
18:08Because this is something that she built for eight years. This is not something that she built for eight years. It 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 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.
18:48That 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 baddie. 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 is kind of like the darling of Australia, especially female founded. And they have had a rough August.
19:24The 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. 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.
20:02They're hanging on so that their shares vest 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. You better believe he's been a loyal employee, but after 18 years, you want to see those shares vest and 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 IPO-ing because people are so upset and so disgruntled? I don't think you can put pressure on someone to sell or to IPO.
20:36That 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 Canva today? You know Australia is a great market. I used to live in Australia before LA. 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. I mean I think by far the biggest venture-backed company from Australia that I'm aware of. Amazing she's a female. Supposedly she's a great person.
21:08the whole thing, but it can be isolating being in a place like Australia. And you hear these stories of the US 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 cannot have your engineering team, the backbone of Canva, be disgruntled and that could be very well what's happening.
21:40And all of these people have been millionaires on paper. Is there any way for them to create leverage 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 wanted to just go sell my shares I was in Canva and I was an employee, depending on how the contracts are written, sometimes you need the company's permission, which, of course, they don't want to do if it's like a 30 percent discount to your valuation.
22:11It 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 who have joined Canva in the last couple of years when the valuation is already really high.
22:41I 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. 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.
23:17And then all of a sudden things start dropping. Well, the trickiest part, too, is 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 and 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 that acquisition is a very small percentage of the function valuation.
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23:49I 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 diligencing 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? 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.
24:26Do 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? 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.
25:03Why? Because if you're not a senior executive making a bigger salary and I'll call it salary base plus bonus, 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. 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 timing and it's not guaranteed. Do you think that it's changing now with names like Alex Earl invest in Symbiotica and all of these celebrities are starting to show the power of equity?
25:38Because 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. And 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. 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.
26:18I 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? Earl's probably not hurting for money, so it's easy. And she's getting more equity than an 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, they're making sure that they're saving a little.
26:54But I think that's important. Maybe I don't think they're quite as correlated as you are, because Alex Orwell's 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 Orwell's world and the influence, I totally agree. They want more equity. Going back 15 years when nobody was calling it creators or influencers or whatever, we had some different 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.
27:31I went through, hey, here's what we're looking for. Here's whatever. Here's what we can offer. And I'm going through all the lists 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? 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.
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30:26Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required. Compatibility and availability varies 18+. Propel Fitness Water with Gatorade Electrolytes, zero sugar, and vitamins. Propel hydrates better than water to help you get the most out of your workout and get back to your best self. What propels you? Propel with Gatorade Electrolytes. So I made that video about Alex Earl investing in Zymbiotica. It has over a million views, was reached out to by UTA, all of these agents 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.
31:09Why 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 of 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 thinking about wealth creation or creating generational wealth the way that creators are.
31:46I 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 Earl's different than a main street consumer. But I think everyone wants to feel entrepreneurial. Everyone wants to take those swings, but you just have to feel like you have enough of a nest 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 Earl's invested in it, therefore I should because now we're throwing out all the principles we've already talked about and we always talk about.
32:23entry point. Alex Earl, we don't know what deal she got. She might've got a discount to the last round. She might've got advisor shares. The average person is not getting advisor shares in Symbiotica. And by the way, I like Symbiotica. I don't think it's a great investment today because the valuation is 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 who's in Symbiotica, if it 2X is from here, everyone's super happy. I really liked the product. I think one of my very first learnings back to my Goldman Sachs days of working on things like Procter & Gamble Gillette's merger, Under Armour's IPO and things like that, is there is a difference between a product that I like and that I consume and what makes a good investment.
33:03And sometimes they overlap, but you have to not confuse the two. And that's what can easily happen with Symbiotica and Alex Oro. 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 come back to?
33:37Of 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, when I say off camera, I mean in our real life. So I'll say it to everyone. In our family meetings. In our family meetings that aren't live streamed. But is that there's a guy, I don't really talk to him anymore, but named Howard Morgan, legendary venture capitalist. Now I'm forgetting. I think first round capital. He's the founder of. 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.
34:14And now maybe this was a few years ago. So it was before AI. So who knows? But he's doing it by hand. 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. That's the only thing he goes, wow, I had some right ideas, but wrong timing. So timing means a couple of things. It means I have had a couple of companies that I even started or invested in.
34:49And I was like, oh, you know, as you know, we're investors in Lyft, but we're 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. But we were right around it going, OK, something's going to happen here. So we said timing. So timing means a couple of things. One is, you know, even even our first company we started, like an organic, better for you vodka alternative with acai and other things that help with hangovers.
35:17I 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. 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 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.
35:48Which Alex did. We're talking to people listening to this. They're not getting any preferential terms, and they didn't see Symbiotica when it was just starting out in Erwan. 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 you're 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. 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 model's ahead, your functionality ahead, so people understand it now.
36:22But six months ahead in trends can be really big. And so I think it's really important for that timing piece. 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 1, a 2, a 3x, 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 that return? This is what people need. this is the only thing people need to understand about investing. Private invest and public investing is what is the barbell or what is the teeter-totter of risk reward?
36:58Because 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. I go, 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.
37:31In fact, during Tim Cook's tenure, Apple has like 10x. So you got like a venture style return for very little risk, risk that it goes to zero, maybe it doesn't appreciate. So a lot of times when 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's a chance to be 100X, not a high chance, but a chance. And both the things, the thing you showed me and 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.
38:07Investing is all about asymmetric risk reward and trying to find And timing is a big part of that to bring it all full circle. So I feel like if anyone's going to get one thing from this conversation, if they're thinking about investing, 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. Chomps? Not chomps, but clothes.
38:41How many chomps did you have yesterday? Five. Okay. That's an everyday product. We love daily habits. We love daily habits. Wearables are heading to Wall Street. According to the rumors, Aura 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. Yeah. Does that seem fair? I don't know why they raised quite so much in IPO, 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.
39:17So anyways, if they can raise$3 billion, it probably means they have big, big plans. What do you think about that? 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 Oura 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 the same thing.
39:54They just have different entry points. And whether you're Equinox Gym or Aura or one of our companies like Lifeforce, eventually you're all still 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. If I feel good, I don't need a ring to verify what my sleep score is.
40:28And 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? 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.
41:00That'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. Like those are not the to your question about first principles. That is not the first principle. It'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 to go out dinner with our friends talking about was the women's health story to this. because Aura has recently found a huge part of their ICP, their customer base, with women that are either layering hormone tracking, pregnancy tracking, perimenopause, taking their temperatures, fertility.
41:39Like 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 Aura's IPO is the focus and hopefully trickle down effect that this will have on women's health companies. 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.
42:19And I'm hopeful that whether it's or 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, Aura 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 the road, it will be. And I don't know what the things have come out of Aura specifically for men are, but you didn't name any.
42:53I 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. Your hormones change more in several hours around me than in my whole life. No, our hormones change more in a day than yours do in a month. For sure. And I see that. But 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?
43:36Like, are they diligencing 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, 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 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.
44:09And 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, 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 assume 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 Yuka, where you scan the bar and it tells you if something's healthy. It has its limitations, but it's about trying to do your best to triangulate that.
44:42You know, I was invested in a company called Supco that was doing the same thing for supplements. And I think 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 that's the part people need to like be there. It's also like what what is good for me 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.
45:12But 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. Like 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, oh, look, she missed that.
45:47And so for me, when I look back, even I showed you my MixLab in deal memo, you're like, why 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.
46:25And 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. I thought that you were. Also, even like governmental stuff that didn't used to matter, depending on your view of RFK and Maha and all that. Some people might think they can trust things they're recommending. Some people might not. I'll let people opine on that. But it's all that, right?
46:57It's so hard to know and there's not a single source of truth. And peptides are going crazy. If somebody watching this has 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. 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 GLP-1s at least has a lot more research.
47:35It'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 GLP-1s 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. 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 Steven 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.
48:14They are going to, whether it's prioritize their newsletters, prioritize in real life events, 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. How would you reach that person? Because that is what it is going to start to become, where it's not about the best social campaign anymore. It's like, how can you be in someone's mailbox? How can you surprise and delight people? If you're at a grocery store and you're a product, Yeah. People look at their phones while they walk down the aisle, but I argue you're not really doing either well.
48:46So it's like, theoretically, you should 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 AI mode of Gemini or ChatGBT 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. This product on the shelf. Whoa, I never noticed that.
49:16What 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. We're not done. No, but I just love you. I love you too. 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. 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?
49:57Well, 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. But I think, you know, you're a 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 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 how I am. Not everything that, you know, not everything that you can measure matters.
50:33And 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 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 to you all my financial situation in one sitting, I think there's like managing directors of Goldman Sachs who wouldn't follow it. I know there aren't because I've been with private wealth managers who I've talked to about my own and they can't follow.
51:09So 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 that come into play that are part of our prenup. 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 or what will happen and all that. 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 shared all at once. Or 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.
51:46And 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 sorry 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 had like i think that i was maybe worried about being embarrassed or being like oh is he gonna think that i'm less than or that i 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-getter 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 which would you yeah 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 that.
52:50I'm protecting myself. Whereas with you, I think the 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.
53:27I was like, I believe in my potential. 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's 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 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.
54:09And 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. Might not be the most important one. You definitely don't get to take it with you when you die. So I think that's a big thing to think about, right?
54:42And 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've had on Hot Smart Rich 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, especially being a female entrepreneur.
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56:12I 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 without replacing the human judgment that actually makes the work really good and unique?
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57:26Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required. Compatibility and availability varies 18+. Propel Fitness Water with Gatorade electrolytes, zero sugar, and vitamins. Propel hydrates better than water to help you get the most out of your workout and get back to your best self. What propels you? Propel with Gatorade electrolytes. This one's very interesting. My friends are all starting to make more money than me and I feel like Like I can't keep up with their lifestyle. How do I have that conversation with my friends?
58:03Do you want to hear the first instance that came to me when I was reading 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. 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.
58:34Like, 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. 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.
59:11You 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 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 that you want to keep, it's like find activities that are free or don't cost a lot of money.
59:41I'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 just 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 it 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 honestly, 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.
1:00:17I don't know. Maybe there are friends that 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 friend. 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 friend.
1:00:49When 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 pick 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?
1:01:25And just hard to be all things to all people. 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 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 or someone has to prod them a little because it's like as I've always said it's it's you know it's thing about being an entrepreneur a 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 oh if I could just get past this one little as your business partner, Stephen, calls it, paper wall.
1:02:31All 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 it better than 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 hundred rabid people who are loving my thing.
1:03:04That 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 elusive customer, but the ones you have found sure love it. And that's just like a matter of time and timing. And then other things are 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 it is.
1:03:38It'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 over complicate 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 thought run in there and save all the things, grab as much as 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.
1:04:14Right. 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, 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 field. The market has spoken.
1:04:48The market has spoken. Doesn't mean you're a worthless person. 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 then imagine. 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 100. So it's like, how do you know which path that you're on?
1:05:17And I think because they saw something there when it was air bed and breakfast that somehow people were liking it 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. 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.
1:05:43I 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. 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. 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.
1:06:14Like if we say, yeah, shut it down and you get that gut instinct, really, 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 this sense of like, yeah, 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.
1:06:41We know things in our bones and in our gut. 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.
1:07:19The 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 and like, how do I feel after consuming this piece of content? And if it makes you feel good, take that into consideration. If 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 that's true. And I was just going to say, you know, in this group I've been in for 17 years called YPO, which is the biggest worldwide CEO group, basically, there's a saying they have, the only vice is advice, meaning it's a peer-to-peer group, so it's different, right?
1:07:59It'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 da-da-da-da-da. 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 that sounds like the recall of your food brand. And I think it's really helpful. It's different when it's a pure situation, but I think what most people lose track of, and this is probably my final halfway decent insight for the day, is you are the CEO.
1:08:32Even 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 it's 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.
1:09:02Part of that's that AI is not foolproof yet. It may be at some point, but part of it's like, I know something either in my gut or experience should be different than 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. And I should 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 percent of your audience, but if one percent finds it useful, great. And maybe there's other things that are more relatable, but you have to decide, like, what to adopt, what to let permeate you, where your attention and energy goes.
1:09:40Love you. Okay, we have to finish with just quick rapid fire like we do every episode. Okay. Okay. Courtney Ream, what is the last thing you put on our credit card? What's the last thing I put on our credit card? The last thing you put on our credit card was our laundry. Our 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 credit card was some really nice flowers for you for our one-year wedding anniversary that I surprised you with. And I cried. I have a video, people.
1:10:13We'll post it. We'll post it online of her being surprised and crying. Her saying, I need to go in the room. I got to pee. I got to pee. And next thing you know, she's crying. What is the current book you're reading? One of my favorite authors, David Brooks, formerly of 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 eulogy 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.
1:10:47So I'm loving it. Trying to make me a kinder, gentler, more empathetic person. Courtney Ream, thank you so much for coming on Hot Smart Rich and 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 next time. I love HSR and all the angels. Just want to get invited back, so please. If you're starting a business, there are certain things that are so fun to think about.
1:11:21Y 'all know I love a mood board. So everything that relates to the creative, the name, the brand, the website, the vision board. But then there are the things that make you pause and ask, am I even doing this correctly? Or do I even want to be doing this? Like forming your business, getting the right documents, keeping your personal information private. it. This is where our sponsor at Northwest registered agent is so helpful. They're a one-stop shop for founders who want to launch and legitimize their business without turning it into a giant admin spiral. They help you form an LLC or a corporation act as your registered agent and give you tools like a business address, operating agreement, website, phone number, professional email, and free guides.
1:12:01They also have real corporate guides who know your local laws. Visit northwestregisteredagent.com slash hsrfree and start using free resources to build something amazing. Get more with Northwest Registered Agent at northwestregisteredagent.com slash hsrfree. Should she say that about the kisses? Is that weird? She doesn't care. She presses send. This is the love story of real hinge couple Daniel and Roisin, written and read by me, Rufy Thorpe. Listen to the free audiobook now.
From the publisher
Serial entrepreneur, M-13 co-founder, venture capitalist, and HSR husband, Courtney Reum, does a deep dive into the biggest business headlines, tech valuations, and financial topics that you need to know this week on Hot Smart Rich with Maggie Sellers Reum.
Together, they break down the market buzz around the BÉIS acquisition, employee backlash over Canva’s liquidity and valuation numbers, and Oura’s path to a massive IPO. They also talk about the latest trend of creators becoming investors and their private playbook on what actually makes a good investment.
Plus, Courtney and Maggie open up about celebrating their first wedding anniversary, highlights from their European summer trip, and take audience Q&A to answer your burning questions about couples' finances, talking money in friendships, and building long term wealth.
Get unselfish access to insights that will help you own the room. Sign up now https://linkly.link/2jPXJ
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Timestamps:
(00:00) Intro
(01:06) Euro Summer
(05:36) Why Should People Listen
(08:13) Staying Informed
(08:58) Shay Mitchell & BÉIS Deal
(15:10) Why Control Matters
(17:22) Canva Employees and Building Equity
(26:31) Stan Store Ad
(27:28) SoFi Ad
(28:42) Investing in Creator-Led Businesses
(30:59) Courtney's Investment Principles
(36:18) Oura Ring Goes Public
(41:12) Why Women are Better Investors
(45:33) Consumers Online vs Real Life
(47:14) Questions From the Angels
(47:36) Talking to Your Partner About Money
(52:38) Eight Sleep Ad
(54:01) Fiverr Pro Ad
(55:00) How to Talk to Friends About Money
(58:36) When Is It Time to Quit?
(01:06:48) Rapid Fire
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Sponsors:
Stan - https://ig.getstanley.ai/?ref=hotsmartrich&utm_source=podcast
SoFi: sofi.com/hsrloan
Eight Sleep - https://www.eightsleep.com/hsr and use code HSR for $350 off
Fiverr - If you are scaling a business, then you need to visit https://pro.fiverr.com
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Hot Smart Rich: Your Business & Culture Gossip
For ambitious women wanting to own the room, gain power, and build wealth.
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