The Hot, Smart, Rich Glow-Up Guide for Entrepreneurs

0:00Women in the U.S. hold 85 % of consumer spend, yet we only get 2 % of venture dollars. but we're great consumers. So to be a good investor, to be a good founder, you have to understand consumerism. Hey, welcome to Shopify Masters. I'm Shuang Esther Shan. You probably got big goals this year, both in business and life. And our guest today is here to help you accomplish it all. Maggie Sellers is an angel investor, startup advisor, and content creator. She has more than 100 ,000 followers on TikTok, and she shares her advice on taking big bets on yourself and getting more business savvy. Maggie is the co-founder of Hot Smart Rich Media and HSR Ventures.

0:44She invests in consumer brands and technology companies like Dassois, Doe, Alara, and MixLab. Thank you so much for joining us today, Maggie. Thank you so much for having me. I'm excited. Yes. So you are, I think, the definition of a multifaceted person with multiple jobs, any one of them would be someone's dream job. I would love for you to tell us about that pivotal moment in your career where you decided to bet on yourself, turn down a full-time job, and really take this turn in your career path. So I think I always knew that I loved building things. So whether it was as a full-time startup operator or just a side hustle, whatever it was, I love to build things.

1:29And when I was at the last startup that I worked at before I went over into entertainment as my full-time job, I had the president leave that I had grown a relationship with. And he was starting a new startup. He had been a successful founder in the past and had a great track record, loved the idea of the business. He wanted me to come in as a full-time employee and leave the startup that I was at where I met him. And although it was an amazing opportunity, I knew that I was looking for something both from a personal perspective to like, tie my identity less to one thing. And also from a professional perspective to really expand and have a portfolio of things that I was doing.

2:09I knew my end goal was to be in VC to be able to invest capital, my own capital and other people's capital. And this just felt like the best opportunity to try to negotiate being an advisor to his startup versus going in as a full-time employee. And that's exactly what I did. I was able to kind of wiggle my way into turning down a full-time role so that I could end up being an advisor in his company. And that's kind of what spearheaded where I'm at today. I can't even imagine having those tough conversations, but you're really advocating for what you want and building out the career that you would like to have.

2:47So you start angel investing, you want to be in venture. How do you then also decide that you want to be in content creation as well? It's like, especially with this being in the new year, it's about having a vision and then working backwards. I knew that I wanted to really be at the forefront of storytelling. I think I'm a storyteller by heart. And that's what a good marketer is. Somebody that's good at brand marketing, they can tell a story. And I think, you know, I was never really tapped on my shoulder to just get something handed to me like, oh, you want to be in VC or here's a job. And I think content creation was something that I thought I could do differently.

3:27And at the time, nobody was talking about business in the way that I have. And really, I would say I'm one of the few people that have pioneered, especially angel investing and democratizing that on TikTok. And I had started posting videos just like wanting to share everything that I had done in my career, there, maybe a little bit of a chip on my shoulder, not having been tapped and felt like there was a lot of value that I could provide people. And I always had that vision of like, where could this go? And I think when you're starting something new, whether you're an entrepreneur, you're a content creator, you have to think you're going to be the biggest thing in the world.

3:59And that's how I honestly thought it was going to go from the get go. And it's not been that way. It's actually been a very slow growth. And I just hit 100 ,000 followers. But in my head, it was like, don't sacrifice things to just skip steps. Do things for a mission. Do things for the right reason. I never wanted to be a content creator that was pushing product 24-7, getting people to buy things. I really wanted to create content that was something I found I was talking about organically. So I remember if you go back to some of my first videos, I made a promise to myself, which you can still see publicly, that I was going to act as if you were at dinner with me.

4:39So we don't just talk about business at dinner. We talk about fashion. We talk about travel. We talk about relationships. And then, yes, I do like to surround myself with people who spend the majority of their time talking about ideas and businesses. But I never wanted to just niche down sacrifice. I knew I wanted my content to resonate with people in a healthy, positive way and hopefully didn't make people feel less than and that they had to buy things just to keep up with me. but they could be a part of not only me building my dream life, but hopefully inspire them to do their own. And it's so cool hearing you giving that behind the scenes thought process, because it does feel like we're just at a dinner party with you where you're talking about the thing that's most interesting to you in the moment.

5:26The other thing I love is you've also brought this business perspective to content, seeing a gap in the market, because to your point, It almost sounds counterintuitive where media makes you feel like you could only be smart or rich, but you can't be hot. You can also be this multifaceted person. So I love that so much. Yeah. It's funny because I think what differentiates me as a content creator is I'm a business person and I invest in companies. So it's like, I'm trying to nail down. Why is this founder sacrificing everything, sacrificing a paycheck to build this? And it does go back to their why, to their mission.

6:04And I think the exact same thing as me is with content. Why am I doing this? Why did I call my company Hot, Smart, Rich? So polarizing. And I would say like, yes, there have been times when it's been totally taken out of context. And a lot of people look at me, I'm sure, and think you are hot, smart, and rich. And it's like everybody is if they claim that energy. And it's not about gatekeeping that we've traditionally seen, especially as it relates to angel investing. and so I think for me being able to really own who you are and I go back to this girl that wanted to express her femininity wanted to express who she was and I think women are taught especially like you won't be respected you can't build a business you won't be able to raise money if you show any sign of femininity or what we would call hot and that I think is so antiquated And I think, you know, something that I've posted that's really resonated with people is women in the U.S.

7:04hold 85 % of consumer spend, yet we only get 2 % of venture dollars. And that's been a trend for, I don't know, at least over a decade. But we're great consumers. So to be a good investor, to be a good founder, you have to understand consumerism. You have to understand the consumer. So why are we trying to change women from being that to trying to fit into this masculine and stereotype that doesn't have to be that way. And I think if I'm a catalyst to helping more women really embrace all sides of themselves, be multifaceted, be themselves, sure, there will be people that won't understand it. There will be people that pass on me because of my company's name.

7:46And in my head, I'm like, your loss, not mine. I love that so much. Of course, now you're an investor, an advisor, content creator, so many roles, but it actually began in an approachable way. You were tapping into your local startup scene. You're from Toronto, Canada. Share some of the tips for reaching out, cold calls, and the early days of building out a network. So two things I want to touch on with that, because now that I'm the person that gets a thousand emails a day and DMs and whatever, it's impossible to return everything. And it breaks my heart because like I was once that person that cold called like literally every single founder I wanted to work for.

8:28So I think my number one tip just in general on networking and especially going after what you want is it's a numbers game. It's like anything in life, like you aren't going to get a response from every single person. And you have to be able to provide people value. Like just asking people for a coffee chat, you have to think about the time that it takes them to get there to sit down with you to do that. What are you going to be able to provide for that person? It's more important that you communicate that than asking for their time. So that's number one. As it relates to community in Toronto, I am such a proud Canadian.

9:06I'm so proud to be from Toronto. I'm so proud of the ecosystem that's been built there. And when I was moving from Salesforce to really my first startup called Freshie, there was only so many startups that I wanted to work for. And I just think the explosion of innovation, creativity, brands that are in the Toronto market, specifically, I always say because of Shopify, they've bred such an amazing network of alumni. It's such an amazing opportunity for people to really take advantage of that now and to see like who is building something that's taking their expertise. That's what I've always done is like follow people that have either a really clear mission.

9:46They might not have done something amazing yet, but they are on the path to do that. Or they have a really amazing background and track record. Where are they an alumni of? Where have they worked? What are they passionate about? Do your research because to me, that shows that you actually want to work with me. So I think it's just around being really curious, going to events, cold calling, like not just asking for coffee chats, but like being really intentional with making sure that you're either cultivating moments that make sense for people to take time away from the countless other opportunities that they have and just being super thoughtful in your approach and always doing it because again, there's a mission to it.

10:25It's not just to like be self-serving and it be a one-sided dynamic. Be thoughtful, be curious, and also tapping into the local startup scene who might be building a new store or new business on Shopify. Such great advice because you can kind of apply that to any city. For our listeners who are aspiring founders, I'm sure a lot of them start off building things on the side, which is something that you've done in the past too, juggling many different side hustles. How does one balance everything when they got business goals and personal goals for the new year to make sure that they're not only staying afloat, but they're also thriving in the things that they put their energy towards.

11:10I think that's something that is even still a struggle for me because I am such a visionary. I would say like I have so many ideas that it is around prioritization. Like I forget where I heard this, but I really implemented this and it's made me incredibly productive is you can really only do three essential things a week. Like if you have a to-do list of massive projects and you have so many things to cross off your list, you're going to get into analysis paralysis. And it's hard to even know where to start because it just seems so overwhelming. Whereas when you only have a certain amount of things that you're trying to accomplish and you can actually cross something off of that list, it just makes you feel like you're moving steps forward and you're not stuck in that decision of like, I don't feel like I'm going anywhere when in reality, you're actually going a lot further if you shorten down the amount of things that you're trying to do.

12:01So I think it's like really being clear on what are your top priorities. What is like a stretch goal, but what is realistic for you? I'm a huge believer in habit stocking. So for example, for me, I like to get my hair blown out once a week. I don't like to waste time like having to do my hair. What do I do? I bring out like five different pitch decks on my tablet. I'm in the chair for an hour, an hour and a half. I'm reading pitch decks. that to me is like such a good use of time, both from a personal and a professional perspective, where I'm actually getting two birds, one stone done. And then I just like totally live by my calendar.

12:37If it is not in my calendar, it's not happening down to like, honestly, when I'm calling my family, like all of that is just it has to get mechanical at some point. I block my calendar as an example for creative thinking that people could say is so mechanical, but really, there's no agenda to me going and having a creative thinking moment. It might be going to a coffee shop and seeing what comes out on paper and pen. It might be going and reading a magazine and understanding what's in the zeitgeist right now and being able to either find a company that's doing that or build content around it. So it's not as mechanical as I'm making it sound, but it's just being so diligent with your time.

13:15And also the other thing, and I would hope, especially women, because I know we are so not experts at asking for what we want, being direct. A great example is I've been asked to fly to a few different cities for the top of the year and speak on panels. And I've quite frankly, in the pre-production calls, like just asked the organizer, these are my objectives for the first quarter of the year. This is what I'm trying to do. Can you honestly tell me if this is a really good fit for the event that you're organizing, or if it would be better for me to help you maybe find somebody else and then revisit me coming at a time when I'm not as in crunch mode.

13:52And I would never have done that five years ago. But truthfully, I think that directness is not only going to save me the stress and the headache, but it's actually going to help everybody achieve their goals without coming across as like, I'm so busy, I'm unavailable. Let me help you find somebody. But this is what I need to stay laser focused on and then we can totally revisit if this makes sense in a later part of the year. Not mechanical at all. It's tactical and it's practical and it's these kind of advice that our listeners can take away and try to implement. So our calendars, our to-do list is just one side of the things that you talk about planning out.

14:32You actually have a great tip for budgeting. You talk about how we should actually view it as the 50-20-20-10 rule where 50 % is going to your necessities and your needs, 20 % for your desires, maybe splurges, 20 % for savings, and 10 % for investing in your goals and yourself. Tell us more about this concept. So I think the 50-30-20 rule is incredible. I think it just developed discipline. But I do think it needs an upgrade. And I think this is why I am so excited about what I'm doing, because I really am democratizing knowledge of the rich. And the secret is that people invest in themselves, especially when you are trying to build something from the ground up.

15:17So having this mechanicalness of like, you can only put money towards savings in the traditional stock market. Then you have like your splurge that people are spending on that Sephora purchase every single week or travel. and then you have what you're putting towards like your needs. So your housing, your food, your transportation, daycare. I felt like there was this missing piece to invest in yourself. And every single piece of advice that we hear from entrepreneurs is bet on yourself, invest in yourself, risk everything that you have. Okay, don't risk everything that you have. But if there are things that you can do over a period of time that are going to be investing in yourself, whether that is angel investing, because it's going to broaden your network.

16:03We know most startups fail, but if you just allocate as an accredited investor a small piece of your income on a monthly basis towards angel investing, you would be surprised how far your network will grow. Maybe you're not an accredited investor and you've been debating joining a membership club in New York. Business is around knowing the right people. It's around creating opportunities for yourself. This is what rich people do. They invest in themselves, whether it's being at the right membership or golf club, it's meeting the right people to get to be investors in their company, or it's investing in businesses that are going to go public one day.

16:41I don't look at a membership club or an angel investment as a splurge. That to me is actually an investment in myself, whether it's in my network, it's in actually something tangible, but it's really an investment into your growth and development. And I think that's really critical for people that are looking to accumulate wealth and really try to take themselves out of how hard it is for this generation to actually get ahead because it is a lot harder. It's kind of shocking to me that that hasn't been democratized further, but obviously exciting for me because now we've really been able to own that.

17:17And it's something we have a lot more stuff coming out about. So such a practical way to think about how to budget for yourself personally. And we're definitely going to talk a lot more about starting a business. By the way, if you're enjoying this conversation, subscribe to Shopify Masters for weekly business inspiration from founders and experts. Also, leave us a review or comments for the show. It helps others to discover the podcast as well. Thank you so much. So one of the areas we talked about that I love the fact that you mentioned the stat where 85 % of consumers are women and yet only 2 % of VC money goes towards female founders.

18:02If a founder is actually that lucky to go into that route and maybe start out with angel investors or go into VC, what should they be looking for in terms of a good partner in addition to being a good investor? That's obviously a dream state scenario. So I would just say shout out to all the founders that are trying to raise capital right now, because the market has turned, it's really hard. And I think, you know, you are going to want to just take whatever comes along in terms of money. But I would say, like, try to get creative before you take any money, because you really do want to make sure that you're in business with the right people and the right investors.

18:40And some of the biggest questions that I would be asking is just like, what is the vision that they have for the company, really trying to understand that their vision and your vision are totally aligned. Being on the same page about like expectations, even down to the involvement, how often are you going to be expecting decks and models to be made? There is nothing worse than getting an investor that you think is going to just want an investor update once a quarter. And then they're pestering you every single week to be like giving them access almost to your Shopify in a way, like just by how many models they want.

19:15And then I also think, especially if you get into more of like the fun side is really understanding like how big their checks are. That's something you should definitely ask on every single call. Don't be embarrassed to ask that. I also think if it's a fund is, do you have allocation for follow on investment so that you can kind of get an understanding? It is a tough position when you take on, let's say a lead investor, they maybe even have a board seat or a board observer, but they don't have any money left in their fund to allocate for follow on. So you know that like you are absolutely going to have to find another lead investor down the line, which I would recommend if you have the opportunity to just to have more eggs in one basket.

19:55But you also kind of do want to know that if there was ever a situation that you needed a bailout or you needed somebody to put in more money, There's an option for that. So I think it's just about like being able to feel comfortable even to ask them questions like that. Like if you feel you can't ask direct questions to a potential investor, that is not a good sign. So I would not be ashamed to ask check size. If they have allocations to follow on, how easily they'll be able to reach. And then what's their value add? How are they going to help you add value? What are tangible ways that they've done that in the past?

20:33And everybody's value add will be different. And I'll give you a great example. The last deal that I just did, I really had tried to advocate for a fund that I work really well with to also invest in the deal. It was a highly oversubscribed company. And my value add is completely different from the fund that I knew I really wanted to get in. They are more like amazing at board updates and helping with putting memos together and board decks and models. And that is not something that I am an expert in. And, you know, the founder after her first board meeting texted me and was like, thank you so much for advocating that they get in because the board deck went so well.

21:10The meeting went amazing. And it's just having your investors even work together. Those are all things that I think, especially as you're starting out, you don't understand how this all fits together, but it really is a puzzle. And you're trying to put pieces together that are going to make sense. And some people will be really good at this and others at this. and you don't want everybody to be the same. So you want to make sure you put in your corner an unfair advantage. So think of it like a sports team. You don't just want people that can shoot the basketball. You want different players that are going to add value.

21:43You want a coach and you just want it to be all-rounded. That's such a good perspective because reviewing investors and looking at what skill set they could bring in to make sure that it's complementary to the team that you already have. So very often, I think investors talk about they're not investing in just the idea. They're also investing in the founder. A lot of this has to do with the X factor or the soft skills. What would you say to aspiring founders on how to actually cultivate some of those skills? Amazing question. And this is something that, you know, one of the hardest things about being an investor is the feedback loop when you're starting out, right?

22:22Like we think it's like seven to 10 years to even see like, is what you're doing actually going to work out for you? But one of the things that I can say confidently after, I guess, like four years of doing this now is the only through line is the founder and the market. Like the idea can change. The company can pivot. The business model can change. The founder is, and it's hard because it's so unquantifiable to say like, oh, this is the type of founder. It is such a gut feeling. And I didn't have the right gut instinct, actually, when I started out. It's like why they say 10 ,000 hours is what you need to be an expert at something.

22:59And I truly believe that now. I think what I look for more than anything during diligence is an openness to feedback without being defensive, but having a really strong point of view and holding it not loosely, but openly. They are open to feedback in a way that they are not going to sway their decisions so easily because you want a founder that's going to lead a team in a very specific way. Somebody that has a great point of view that is charismatic, wants to lead the organization, doesn't go up and down in their emotional responses. They have a very clear way of steering their ship that feels like it's not going to rock people off the boat.

23:45ultimately is a really good salesperson. Like I think founders at a certain point of scaling become a salesperson. They're selling to investors, they're selling to employees, they're selling to customers and they're selling to the market. So if you have somebody that you believe in, but nobody else will, unfortunately they won't get funding down the road and that's when companies die. So I think there's a number of things I could go off on, but to cultivate that, I would say studying history of leaders that have done that really well. Like Winston Churchill is somebody I look up very, very, very often.

24:18I read a lot of books about Winston Churchill. And I think really trying to emulate characteristics of successful leaders, not necessarily who's hot right now in the market, going back way into history is going to put you at an advantage when you're trying to cultivate a real leadership perspective as a founder. Wow. I couldn't agree more. And it's also great to hear your perspective because I think it links back to comments about people saying, you know, you have to be an advocate for what you believe in, but you can't take the feedback so personally. Of course, we're looking at companies and seeing how they could be different and what kind of competitive advantage they have as an investor.

25:00And I think DeSois is such a great example. It's a non-alcoholic beverage company that's co-founded by Katy Perry. What is it about Dessois that was so interesting to you as an investor? I love talking about the example of Dessois because it shows how long the life cycle of investing really is. I actually am pretty non-alcoholic friendly. I have been for a while. I have a rule I don't drink like Monday to Thursday. And I had been looking into the market for quite a long time and had met with a number of founders that were building companies, building businesses. At the beginning, I just didn't like the taste of for some of theirs.

25:39And I think for me, I always have to really like the product as well, especially if it's a consumer brand. But I had looked into it and I felt like the timing was off. So let's take this back four years. Like this was still such a new category. And I think you're looking for just that right timing of like, you're not too early, but you're not too late. So I had been looking into it and I felt like all of the products out there were very niche. so I couldn't ever see them really going to mass market retail. And that's truly where the money is in consumer brands. Like you want to make sure that you can visualize this product like at Walmart one day, at Target, at Kroger's, at Publix, like these bigger retail establishments.

26:24And I just didn't feel like the branding, the community, the world that they were building around their brands were doing that for me. And then I think when I saw DeSois, there was a few things. One, I've worked with a lot of celebrities in my day. I've built celebrity brands. I've launched a corporate venture. I'm at a record label. I know the celebrity world pretty well, but I know what an advantage it can bring if done correctly. Do I think every celebrity brand is successful? Absolutely not. I pass on celebrity brands every single week. But I think what I saw in Katie and just the way the deal was even structured, how involved she really was, the fact that she's sending FaceTime videos to the major buyers at these larger national retailers.