The Ryan Hanley Show - From Single Mom to Queen of the Castle: Ann Kaplan Mulholland

Episode Date: January 16, 2026

Spartan philosophy, built in the black-ops lab of business: https://www.findingpeak.comFinding Peak podcast: https://linktr.ee/ryan_hanleyWhat if every excuse you have is a self-imposed prison?Ann Kap...lan Mulholland's story is a masterclass in shattering those walls. She went from a single mom working night shifts to a multi-millionaire entrepreneur, TV star, and the literal Queen of a castle in England.She did it by refusing to make excuses.In this episode, Ann unpacks the unfiltered, unreasonable, and often hilarious journey of building a business empire from the ground up. Forget the highlight reel—this is a raw look at the grit required to turn chaos into a dynasty.We get into the weeds on:The "Widget Philosophy": Ann's simple, scalable model for creating wealth.The Tiara & Hard Hat Strategy: How to be unapologetically yourself while taking your goals dead seriously.The Art of the Ask: How to get what you want from anyone by being brutally honest.Why Your Website Isn't Your Business: The most common mistake entrepreneurs make (and how to fix it).Building a Brand That Lasts: From writing 7 books to doing stand-up comedy, Ann reveals her secrets to becoming unforgettable.This isn't just an interview. It's a battle plan for anyone who has been told they're "too much," "not enough," or "unrealistic."If you're ready to stop making excuses and start building your own empire, this episode is required listening.Connect with Ann Kaplan Mulholland:•Instagram: https://www.instagram.com/annkaplan_ownit/•Website: https://www.annkaplan.com/•Lympne Castle: https://www.lympnecastle.com/--This show is part of the Unplugged Studios Network — the infrastructure layer for serious creators. 👉 Learn more at https://unpluggedstudios.fm.Advertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

Transcript
Discussion (0)
Starting point is 00:00:00 She was cast on the Real Housewives, owns a castle in England, and sold a company that did business with over 16,000 doctors. But still says she doesn't feel glamorous. This is Dr. Anne Kaplan Mulholland, a single mom who worked night shifts, built a finance empire from her kitchen table, and now owns 14 luxury properties across the globe. She's about to explain why the most successful entrepreneurs never buy into their own hype,
Starting point is 00:00:27 and how she used a TV show, about her castle. Yes, her castle to build a global brand. If you're grinding away but still feel like you're faking it, you're about to find out why that might be your greatest advantage. This is the way. You have such a dynamic and interesting background. I'm excited to spend some time together. It's great to be here. It's really fun. It's fun to talk about being an entrepreneur. And it's also, I think, secretly, we like to talk about our own journeys. So we like to talk about ourselves, which is probably one of those little things you know at a dinner table is to get people to talk about themselves. And then they go, at the end, they've talked about themselves a whole dinner.
Starting point is 00:01:18 And then they say, oh, you're really interesting. It is amazing, the power of being a good listener and how important it is. I had a guest on probably about a year ago. and he was talk we were talking about negotiation negotiation uh oh my gosh his first name's quami i'm gonna forget his last name i'm sorry sorry man i'll go back i'll have it linked up for everybody but he's he's a master negotiator and he brought up something and just to your point your anecdote there about being a good listener how uh we reflexively when someone like if if i ask you you know hey how was your day and you give me a couple tidbits i reflexively then why
Starting point is 00:01:59 want to barf my day onto you, even though you didn't ask as a way of kind of forming a bridge. And what he was, what his point was, and I found this to be like really interesting, was that actually diminishes your ability to influence or connect with that person, even though we think that we're like finding common ground, that that common ground that we think we're building, it's rarely taken as common ground by the other person. They feel like you just kind of waited your turn to barf your story on them. And his whole point was like, when we ask a question, it's way more powerful to ask a follow-up question or really be that active listener and fight that urge to like, well, I've
Starting point is 00:02:46 done a similar thing, Ann, or I, you know, I have this story that kind of matches your story where we think we're building. And he's like, that's like the worst thing that you can do when you're trying to build connection with someone. And I found that to be really interesting because I think I do that. I'm probably doing it right now. You actually just did do that. It's very interesting. But we're not negotiating, so that's okay. Yeah. Well, I would love for you to share with the audience, your story, or at least as much of your stories you think is relevant, because you have this just wild and dynamic background and all
Starting point is 00:03:19 these different things that you've done. And I think it just provides wonderful context for the rest of our conversation. Well, I think I'll probably put it in a context because I did write a book, and I'm not here promoting my book, but it's called How to Be Successful in Spite of Him. And then I crossed out him when I was going through it and said, how to be successful in spite of yourself. And the reason I wrote that was I started to get invited and I joined the Speakers Group organization and giving lectures. And I was always asking to give a lecture to people that were young entrepreneurs and young female entrepreneurs. And the questions always came up at the end.
Starting point is 00:03:59 How do I do this? This happened to me in my life. And I've got a boyfriend and he doesn't want me to be in the girls in their 20s. And he doesn't want me to really pursue that way. He wants me to spend more time with him or we might get married. We might have kids. And I think we get in our own way from our entrepreneurial drive. and not everyone has to label themselves as an entrepreneur,
Starting point is 00:04:25 but when you want to have it all, we want to build a business and do something big, and that's your vision. You don't necessarily have to say, hey, I'm an entrepreneur. That's a lot of pressure. How am I going to build that? I was invited to give lectures,
Starting point is 00:04:41 and mostly they would, I guess they categorized me to give lectures to young entrepreneurs, and they would end up to be female entrepreneurs. And I would get questions, after my lecture, the girls would come up and they'd say, I don't know if I should do this. It's my have a boyfriend. He wants me to spend more time with him. And maybe we'll get married. We might have kids. And there would be something or someone would say, well, I didn't come from the background you did. They didn't know what background it came from. They just assumed I maybe had a
Starting point is 00:05:09 silver spoon in my mouth when I was born or something like that. And there would always be something that happened with them in their lives that they would put in their own way. And so that is why I wrote a book about how to be successful in spite of him and cross out him and he said, by to yourself. Because, and I'm not plugging a book, but it made me think about how we get in our own way. We take our history, our current situation, and we get in our own way from doing the things that we want to do. So being an entrepreneur, I think you have to get out of your own way. and away from all of your own excuses. So I was a single mom with two kids,
Starting point is 00:05:52 and I could say, okay, and I got to look after the kids. Well, yeah, I do have to look after the kids, but I have to figure out a way to do it. And so I had this thought, and I had said to my mother, I never ever want to work with my hands. I never want to work for $10 or $15 an hour or whatever, $100 an hour as a surgeon, or something that was capping what I,
Starting point is 00:06:16 would make. I wanted to do something with widgets. And widgets can be anything. But if I had widgets and I could make one widget, then it would cost me whatever the cost that widget is. But if I could make a million widgets, then for the same cost as a setup cost, and then your variable, and I did think like this as a young person, that I could make a million times one dollar a widget. And if I could keep on doing that, then while that was the end of that would be successful as an entrepreneur. And so that was my idea, but I didn't know what my widget was going to be. And I did end up to be a single mom, which was not my dream. And my ex-husband's name is gone with the wind. And I'm sure a lot of people have ex-husband's name gone with the wind, probably the same name. And so I had no support
Starting point is 00:07:06 and two kids. So I could get in my own way, but I didn't. And I think that, was what was really important. I had to figure out a way to do it. And that meant I lived within my means. I had to have a job because I had to pay for the kids, but I worked night shifts. And you have to figure out a way to do it, and it is hard. It's hard, hard work. So I worked night shifts. I had rented out a room in a rented apartment, and the person that rented the room got free rent, but they had to be in the apartment when I put the kids to bed and I worked for my night shifts. And I started a company, and this came from an idea about not having medical care in the future. I started a company that provided financing for medical care.
Starting point is 00:07:55 So say in the future that you were, at some point, you needed to get financing for a hip replacement, or in the case that became very common, people wanted financing for hair transplants. or for plastic surgery or something like that that is necessary, usually out of pocket. And that company started with probably a million dollars in the first year, and I had to figure out how to raise money. And my thought as a young entrepreneur, I was a single mom, two kids. I didn't go in saying, well, I'm a single mom, two kids. I'm tired.
Starting point is 00:08:33 I had to get up early. I worked a night shift. I went into everywhere that I begged for money, but the begging came on a very well-presented, this is my business idea. And I didn't talk about being a mom. I didn't talk about being a single mom. And I went to secondhand stores. I bought a black suit and a white shirts. I looked business-like, even though the last person that looks business-like in a meeting. And I learned to present to my audience. I studied my audience. I studied the bankers and I didn't give up a dime. So I didn't go into the banks and say, you're going to get a piece of my business. I would go in and say,
Starting point is 00:09:14 this is how I'm going to operate my business. And I'm going to borrow from you. I'm not going to borrow for any operating costs. And this is what, I didn't ask them what they pay. When we talk about negotiations, I didn't say this is what you're going to, what's going to cost me. But I would present until I had a bank that bit. And that was 30 doors that were closed in my face, saying you didn't have your competition documents. You didn't know your competition. You didn't know this. You have to get money from somewhere. But I finally got smart in each one. And the next time I went into a meeting, I knew my competition. I had a little booklet that said, this is my competition. And then the next time they'd say, well, you don't have a performer. You don't have any idea what you're going to do. The cost,
Starting point is 00:09:59 The next meeting, I had a pro forma. So I became prepared learning from all the times that the doors slammed in my face. And so that's how I started a business. So finally I had a bank behind me and built that business over 20 years, always. Starting out with a company called Metacard into PetCard and Dental Card and I finance and home improvement and payday loans. And I just kept expanding, but it was the same product. It was one little widget. I loaned an average $5,000 loan, and I named different names, and I sold that through 16,000 doctors.
Starting point is 00:10:37 I sold financing to their patients. I didn't market to the patients, so I knew my distribution was the doctors. I just had to convince the doctors to offer my finance to their patients. And then started an insurance company at the same time that did creditors' life and disability insurance, which I still own and operate that company. And that is insurance for the loans. So I only had one widget. That widget had mass distribution, and I had to figure out how to implement that.
Starting point is 00:11:07 And then put the insurance product on. I could own the insurance, too. And then I started to have websites that were to help people searching for questions about if I'm going to get a hair transplant, should I get this kind of that, and it would link to the financing for those doctors. So I started to help the doctors. And then I started giving lectures to doctors on how to market the practices. And then I started to write books on my lectures on how to market your medical practice during turbulent times.
Starting point is 00:11:35 That was around 2008, 2009, when you had the economic downturn. How to get on the internet for doctors. Like, how do you market on the internet? So I started to learn that my lectures were valuable, but I was writing the lectures from the books from my lectures. The lectures and the books were not my money-making. machines. That was my marketing machine. So when someone writes a book, whether they read the books or not, and they did, the books cemented me as a knowledgeable person, and that sounds really silly, but when you write a book, somehow you're the person that wrote the book. It can be blank pages.
Starting point is 00:12:18 It's the only thing in it could see I wrote a book, but I did write books, and that cemented me as a speaker. So you see where I'm going, Ryan. I was not that person. I became that person and then I worked off of that person to expand my brand or to, I guess, validate my brand. So my brand was a knowledgeable person in the field that I was lending money into. And I expanded outside of that field into home improvement and payday loans. But I was knowledgeable in the medical field, which was my bread and butter. And then I cemented myself as a speaker and then books on the areas pertaining to where I was speaking at. So not necessarily all of them were for the medical industry. It could be the consumer industry. But I ended up writing seven books toward
Starting point is 00:13:10 building my brand. That was my brand development. And that gave me what people would consider a credible voice. Now, you had to get good at speaking. So I didn't just assume I was good at speaking because I probably wasn't as good as I could have been. But I learned that if you did stand-up comedy, you could be a better speaker. So I went online and I did with, I think it was Second City. I think the name of it is. So I went online. I found a place that you could do stand-up comedy and I started taking in-person stand-up comedy.
Starting point is 00:13:46 And that helped me with my speaking skills because if you can keep an audience when you're doing stand-up comedy and you have to keep them the whole time, then you can be a better speaker. So during COVID, I was home with my 3,000 children and my husband. Actually, our family was more than the 10 people you were allowed in a house. And so we got rid of the kid we didn't like. But no, not really.
Starting point is 00:14:12 But we were home with our family. I wasn't sad, but I was home. And so I started to do stand-up comedy on online courses. and this was helping with my speaking because I loved doing lectures. And with the lectures and with the speaking and with my profile increasing with my business, I was starting to be asked to be on news programs and TV morning breakfast shows. And I stopped leaning into the black suit, white shirt thing too. I don't know why.
Starting point is 00:14:47 At some point I felt I was confident enough to not try. try dress like a businessman or a banker. And I never dressed in something that was sexy or come hither young man type of look. So I tried to just dress in something that was more me, but wasn't trying to be too feminine. So not that we shouldn't be, but that to me was important that I didn't distract more than you can when you're a woman that doesn't look like a banker when you're in finance and things like that. But I started to be asked to be on morning shows. And one of the morning shows, the producer came up and said, would you like your own TV show? And so like, yeah, okay, sure. I didn't take that lightly,
Starting point is 00:15:31 because that's that elevator moment. When somebody says, would you like this? Never turn it down. Never say tomorrow. When someone offers you something, grab it, recognize it. And today in the Vodcast and Podcasts world, I actually look up the people. And if they are, if I'm asked to be on a podcast or podcast or my PR person reaches out to somebody and they say, yeah, I'd like you on. I look at where I'm landing because it lives forever and you want to be on somewhere that, not anywhere, but credible. You never say no. Say yes right away. If somebody asked you to be with their podcast or podcast, look up the person first and say yes right away because those moments don't come around again. And that's your brand building on the internet right now.
Starting point is 00:16:16 is because people, before you go into that next thing that you want to go into, they're going to look you up on the Vodcast or Podcasts. They're going to look you up, not on the news streams anymore, unless you stream your own old news programs, because those don't live forever. Vodcast and podcasts do. But when I was back to doing the morning show or the breakfast show, whatever it was, I was asked to do my own TV show,
Starting point is 00:16:40 and I ended up doing three TV shows. And they were makeovers on people. So I'd take someone that maybe had warts on their face or something they didn't like about themselves. And I would either get surgery done on them on camera or we would get dermatologic things done. Or at the beginning, that was at the beginning of Botoxin Fillers after 2002. That was about 17% market awareness then. We would do Botox and fillers and it would be there. Look at that.
Starting point is 00:17:11 Look at her lips are bigger. It was interesting. more interesting back then, but now it would be more shaping or sculpting or something. I did three different makeover shows, three different times. And then out of the blue, I was asked to do a show on being an entrepreneur. And the producer called me and said, Anne, they're casting for another show. Why don't you go do it? And I didn't know what the show was, but I went down.
Starting point is 00:17:37 He said, you've got to do this. And it was a real housewives. And I didn't know when I was auditioning. was a real housewife. I am so not a real housewife. And I mean, I don't, I mean, I'm always this calm. So it wasn't the one to, you know, bitch slap and do all this. But I think they like the mix-up of a reasonable person, if you want to call me reasonable. But I was also funny. And so they, they cast me for the real housewives. We did one season, and then they ran out of money in Canada. But from that in that period of time I sold my company not the insurance company and continued to be on the
Starting point is 00:18:22 National Speakers Bureau continue to write books and just during the time when I was running the finance company I also did my doctorate and my MBA my MSC I wanted to keep my brain going and that to me was important that I'm always learning always learning so what I say in a room isn't as important as how much I understand what's going on. And I like to know, even now I'm going to start in January at Harvard doing AI. And I want to understand what is going on. And so for me, I don't just say, okay, I got there. I got my doctorate. I got my master's of science. It's like, I've got to keep learning. And that to me was really, really important to to be able to have knowledge.
Starting point is 00:19:16 So I'm not going to stop there. And the next step I did while I was doing my finance company was taking what I could and starting to buy real estate. So I started companies, different ones, that invested in commercial real estate. And that, to me, was my bread and butter in the future. The income I would have from that real estate, after I did it had rental income,
Starting point is 00:19:39 was going to be like an annuity. So once those were paid off by the current renters after 25 years, I would have an annuity. And that would mean that the income would be coming in from the rental properties, and I could live any life I wanted to. So if the finance company never came to fruition, or I never sold or anything, at least I have real estate. So we have about 14 properties worldwide that are real estate investments that have income earning properties.
Starting point is 00:20:12 And then I just thought, when I'm buying properties, I'm going to like the properties. So I started to buy more beautiful properties and started to create this thing where I worked with people and had dinners at the properties and invited corporations in to have the dinner. So 150 people for dinner at one of our properties. And they would get to, CEOs would get to meet CEOs.
Starting point is 00:20:45 And like-minded people could meet. And the corporations we'd bring in sponsors and they'd have a private dinner. And then I'd take it up a notch and it would make it a wild party. Not wild as in drugs or things like that. But in our Vegas property, which is 17,000 square foot penthouse, we would have show girls serving the food. We would have geisha girls at the fish tank serving sushi. We'd have the chefs and the flare bartenders,
Starting point is 00:21:14 and we'd have people walking around with poker tables, and you could put your drinks on the people's skirts. And we'd make the parties really fun, and we would only invite CEOs of companies and do them during conferences. So you would bring in during the shopping conference. You'd have the CEOs of big companies. And then Jeffrey Katzenberg does his parties at my place,
Starting point is 00:21:35 and he invites his people in. And they're all private parties. So I started to think, there's something here, and I would always work with an organization that would organize the people. But I'm expanding my network. And then we have our different properties and different locations in Toronto.
Starting point is 00:21:52 And then we bought a castle in England. So I have opened restaurants in the castle, and we can invite people there. And so I'm doing that. So the same people that go to the parties know that I know how to run a party, But in England, we don't have the showgirls. Instead, we have axe throwing and things that people would do at a castle.
Starting point is 00:22:13 And the servers are dressed up in knights costumes and things like that. So you get morphed into a different experience, so call it experience retreat. So I turn the properties, Hawaii, Vegas, British Virgin Islands, England, and Vancouver into different experience locations. And so that was sort of an entrepreneurial mind where I'm utilizing what I've learned and how can I make that even bigger? And then buying a castle was sort of a whim.
Starting point is 00:22:52 How can I make that bigger? So I started to buy the properties next to the castle and I got cast for a TV show called Queen of the Castle going into its third episode. Now you might think that's odd, but the Queen of the Castle is really a marketing tool for my castle. And so this Queen of the Castle airs in seven countries. But what better way to show what the castle is?
Starting point is 00:23:19 And then we opened up so far three restaurants in the castle, and we're creating experiences. And in our third season, we're doing all these wild things that people do at castles. Like we're doing a bike race. around Castle. And we're doing, and we're actually registering that in the UK. And so we start six months ahead and do a bike race. And we just did a Christmas special.
Starting point is 00:23:46 And it's interesting to work with different networks and different producers and distributors in different countries because they want me to lean into normal. And I keep asking them, to not have me lean into normal. When you're too normal, you don't differentiate yourself. So when you try to be status quo or something you're not, you're not differentiating yourself. And it takes a lot for me to tell the networks to let me be myself, because it's more interesting than me trying to be who they envision I should be, how I fit in front of the camera, what the lighting is, let me be myself.
Starting point is 00:24:34 And they'll say things like, your hair is a mess. And I said, but my hair's always a mess. Let me be myself. And the very first time that we started filming, I put on a helmet when we started on the construction of the castle. And I put a tiara, and I glued it. I did it myself. I glued it onto the helmet and showed up for the scene. and they're like the construction hard hat.
Starting point is 00:24:58 The construction hard hat with a tiara attached to it in a gown. And they're like, and I'm like, just trust me. It's more funny if people see me doing construction. And then they just started leaning into it. And so I got to drive the backhoe and work the crane and always in a gown and always with the tiara. And then I'd match my hard hat. I found this place in Australia. You can Google it.
Starting point is 00:25:25 You can buy it and you can design your own hard hat. And then I'd bling it up. I'd go on Amazon. I'd get the bling and bling it up. And I put like a whole blinged up hard hat on. And before you know it, it became a signature. And the producers and the distributors are fifth season out of L.A. That distribute the TV show.
Starting point is 00:25:47 They're going, bring it on. And so it's really fun because you take something, which is a show about construction. and add the humor. So we have knights in shining armor all through our castle. And I set them out to where, almost like a car dealership and had them painted pink and green and orange. And it's interesting because the castle also gets let for real weddings, not on TV. And some people don't like all the nights.
Starting point is 00:26:15 So at least we can move the knights out of the way because they get offended. I don't know why anyone get offended by a pink knight, but they don't like it. and but that's a good thing because the stuff that's that's nailed down you we'm not offending anyone but all the other stuff we can offend people and so that's a little bit about brand building because if you are going to do something you should be realizing that you've got a very big audience out there and who your audience is and to me the audience is and to me the audience is is the people that are watching your show, Ryan, that's an audience. There's somebody that would say, you know, she's interesting.
Starting point is 00:27:00 You know, maybe I'll look up her castle or maybe I'll look up her show. But if you're not interesting enough, they won't do it. And then the bankers, when I go into the banking to fund my company, I had to realize that they are a big audience for me. Like, I have to know my stakeholders. And everything you do, you know your stakeholders. You can be an entrepreneur, but if you don't have the money to set up whatever you're doing, and then you don't understand that when you go out there and you're trying to sell whatever you're
Starting point is 00:27:29 selling who your audience is and your voice is a lot of media your voice is online because they're going to say who you are there's there's a guy that comes to some of our dinner parties in Vegas and he started a company called liquid death have you ever heard of that right so and i'm i'm that's a liquid death thing. I actually called him up one time, and this is sort of a thing that I think is important. He is brilliant. And I called him up and said, I want to talk to you, and I want half an hour of your time. I want to know how to do it. I didn't lie to him. I want to know how do I do this. I don't do, like I'm not very good Instagram and TikToks. I can't stand doing Instagram and TikTok, to be honest, I don't like it. But you know when you're building a brand, you have to do it. So I ask for a half
Starting point is 00:28:22 hour of his time, but I researched him and I thought this liquid death thing. And then it's just water. And it's not even special water. It's not like from Avion or something like that. It's water. Do you know what liquid death is? It's marketing. They know how to market. They have these brilliant ads and I'm not promoting liquid death. I'm really, I'm not promoting it. I'm drinking there. I'm drinking San Pellegrino. I'm not promoting liquid death. Which is also good. But the liquid death is a marketing genius. They have a bus driver driving a bus, drinking liquid death out of a can, and the kids are getting on the bus. Which means that you're drinking water and it's good and it's pure or something like that.
Starting point is 00:29:08 It's so brilliant. Anyway, I asked one of the founders to, for half an hour of his time, when you find someone interesting, ask them for, half an hour of their time and tell them the truth. Don't ask them for half an hour of the time because you're interested in the liquid death water or how they market it. And then ask them for money. Be truthful. Ask them what you want. Tell them the truth of what you want. Do never, never meet someone and say, I want you to invest in my company or something like that. You'll lose them right away. You've just lost trust. Anyway, I asked to meet with him and said, what do I do? I'm like, I want to reach a larger audience, and I'm not good at it.
Starting point is 00:29:52 I can't stand doing Instagram and TikTok. So I do funny videos, which don't always come off as funny, but I don't actually do videos of really who I am. So who I am would probably be a hippie in a bathing suit on the beach in Hawaii with my children. But the way I come across on Instagram is somebody who likes to do skits and dressing a gown. and wear a helmet with tiara or something like that. And so I like to have fun on Instagram. And he said, keep doing that.
Starting point is 00:30:27 Make it short and succinct, but do TikTok. And he said, TikTok's where it's at. I don't like TikTok. It's kind of a mean audience and it's not, they're not very forgiving. Instagram is more forgiving. But at the time, I mean, I've been bashed so much online that it's very difficult for me to go online because you want to retreat, but he did tell me, do TikTok and be succinct and grasp your audience in the first few seconds. So that was probably the best advice that anyone had ever given me
Starting point is 00:31:00 about going online, and it doesn't have to be long. And you can look at all these videos, but that was probably the best thing that I ever learned. So I looked at him. I didn't look at him and say, how do I make water or how do I market water? How do you market? And that was very good for me. I noticed my Instagram, my TikTok went farther immediately. So I started measuring how I was doing. I did retreat when I started getting bashed because people don't know my humor. They take me seriously. But what I did and I've learned to do is lean into it. So if you know you're being good and respectful and somebody is wrong about you, lean into it. Make fun of yourself.
Starting point is 00:31:49 Lean into the person you are. Don't lean away from it. I just thought owning it, but when you come from your soul and your values, you're not really doing anything wrong. And the Instagram, they're bots, they're mean. But you do have to lean into that to market yourself.
Starting point is 00:32:10 So that's my entrepreneurial job. journey, but in all of that, I never made an excuse that in all of that I never said to you, my divorce, my first husband, gone with the wind. I was a single mom. I ended up having four more children. I ended up taking in more children because I ended up helping a girl that had a face, cleft face, and had to have surgery. So she was born without a face. and someone had reached out to me quietly. I had funded her to come up to the time, Toronto, to get surgery because they couldn't handle it in Ethiopia.
Starting point is 00:32:50 And they found surgeons in Toronto. And then her mother and her ended up living with me for years. I still look after her. And I ended up really seriously in our house. My mom had fallen and broken her neck and lived in our dining room. because she couldn't walk. So we had put the wheelchair in the dining room, the main floor. We were renting a house at the time.
Starting point is 00:33:12 We didn't own one. We had six kids, and we brought in an Ethiopian family, mother, daughter. So we had a big household. And I wasn't doing bad. I was buying real estate, but we didn't own our own home. And to me, the real estate was the investment for the future. Our rental home was really a nice home for the kids. And so our money went into the future.
Starting point is 00:33:37 and we put our kids in private school. That was our priority. We were building our future wealth, but we weren't spending our current money. We were investing forward, investing in growth and in businesses. And the money that I made in my businesses, I invested back into growth. I didn't invest in buying a Ferrari. I didn't invest in designer outfits. And when I did housewives, they started asking who my favorite shoe brand was. I didn't know what Christian Lubiton was. I didn't know what Valentino was. I had no idea. Like, why are you asking me my favorite shoe brand? It's like black.
Starting point is 00:34:17 And like, you know, like black shoes, black jacket. They wanted me to dress and gowns and I was like, why? And so it was as much as it looks glamorous, I don't feel glamorous on the inside, so it's almost humorous. in the time, which I think is important for entrepreneurs when I was in finance, I also joined organizations that I didn't feel I fit in, but they would have me. So I became a delegate with the Ontario Economic Summit, and I was invited to join the G20Y and sat on the Finance and Banking Committee,
Starting point is 00:34:57 not right away, but after a period of time. And I started to have a network of a larger REC2. of people and realized there's a bigger world out there. And I would come away from these conferences and something would click that someone would say. And I could apply it to my own business. And so that's where I got the notion of being around like-minded people, but new like-minded people, not your same circle. And you learn so much about business. And you can ask the one question like, how do you incorporate AI into your business? Or HR is always the question, how do you handle people? How do you handle people remotely? How do you handle people during COVID? How do you handle people in general?
Starting point is 00:35:45 But I expanded my network in even to this day, in my phone, in my contacts, if somebody says to me something personal about themselves, I will note it right away under their name in their contact list. in my contact list. And if they don't call me and they call me in a couple years, I'm looking like, oh, you had a baby. She must be three years old. How is little Lucy? Because I'm looking in my contact list.
Starting point is 00:36:14 And to me it's important because my brain doesn't remember everything, but it does in my contact list and back it up in the cloud too. But I have that contact list ever expanding and I do reach out to people, always with honesty of why I'm reaching out. And I do keep in touch with people. And I do follow up and say, would you, why don't I introduce you to this person? And I do follow up.
Starting point is 00:36:46 And I don't introduce people to people that I'm doing a favor to the person and not the other person. There has to be a mutual introduction that they're going to enjoy each other because you're just handing somebody a lot of work if otherwise. So it was brand building while I was building businesses and leaning into who I am and not an excuse. In that stand-up comedy thing, I got asked by sick children's hospital in Canada
Starting point is 00:37:18 to do a stand-up comedy competition, which made me fall in love with stand-up comedy and made me join an organization in the UK, the Bill Murray studio, and started doing stand-up comedy with amateurs where they make you do it in a bar at the end. And I just fell in love with stand-up comedy because I was forced to do it. But then I thought, what do you talk about when you do stand-up comedy? And I would start to do the comedy in person,
Starting point is 00:37:48 and I would joke about, oh, I woke up and I had a bad day and I didn't feel like I looked very good and feel out of shape. And then they would say, you don't look out of shape. So why would you talk about being out of shape? If you went out and you were, you looked out of shape, then that's okay.
Starting point is 00:38:09 And then, so I started to lean in to who I was. And that was a single mom with six children. And an irritating husband and being married forever. And that, my gosh, comedy was my life. And so you realize that life is actually pretty funny. And if you lean into who you are, it's funnier. And you have conversations with the people, be who you are. It's funnier. Like, you can't copy someone else's comedy, but you can be funny just who you are. So the comedy aspect to me in my life is really important. So in my bank conversations, in my daily conversations,
Starting point is 00:38:55 and the dinners, humor is so important. And I wrote another book called, If You Don't Laugh, You'll Cry. And I think that's important. My mother always told me that I wasn't funny, that only people I paid found me funny. But I didn't. pay people to go to my stand-up comedy so that she's wrong. And my sister always told me that I was not funny, that I think I'm funny. And I said, well, people laugh at me. And she said, no, they laugh because you laugh at your own jokes. And then they think it's funny that you think you're funny, but you're actually not funny. They're laughing because you're not funny. I'm like, well, that's actually funny that you think that. So anyway, I said, have fun with life and with humor. And I've done that
Starting point is 00:39:45 the whole way along, not taking myself too seriously, but taking my actions very seriously. And then being who I am, but in the right place. So I know my stakeholders. I know the bankers don't want to listen to my woes about six, seven children at home and my mom in a wheelchair. And, you know, they don't want to hear of that stuff. They want to hear how I can make the money. a little tip with bankers in Canada. October 31st is the bank year end. So I would always call my banker and say, let me know if you want November 1st or October 31st
Starting point is 00:40:27 to negotiate our next contract. Because if they met their quota for their bonuses, they would want November 1st, so it would go into the next year. And if they hadn't met their quota, they wanted it at October 31st. I didn't say because of your bonuses. I would just say, do you want November 1st or October 31st?
Starting point is 00:40:46 And so know the stakeholder of your stakeholders, know their agenda, because it's nothing wrong with people making money off you, but just learn how they make money off you and feed that. Everybody's got to make money. So I would understand how do the bankers, how do they get compensated? With my production companies and with the distribution companies, and with the distributors, how do they make money? And I learned that the more countries that were in with the TV show,
Starting point is 00:41:18 the more money everybody makes. And so when we showed up in Nice at the film festival at MIPCOM, I called out the producers, the distributors, fifth season, and said, I'm going to bring drag queens with me. And they said, Anne, you're crazy. And I said, no, I'm queen of the castle, I'm bringing drag queens. And they said, you can't do that. It's MIPCOM.
Starting point is 00:41:40 I said, trust me, no one who's, who I am, but they'll notice me if I have two drag queens with me, and they're like, bring on the drag queens. We walked through METCOM. I was flanked in a gown with a tiara on, with two drag queens, and we handed tiaras out to everyone. By the end of the red carpet, that was five minutes on the red carpet, by the end, everyone knew who queen of the castle was. So if they didn't know, there was just a crazy lady walking with two drag queens through Khan. But it was, it was, you, you need to get attention in this very noisy world, but in a good way. And so I leaned into who I was, which was the queen of the castle. I leaned into my humor. I leaned into my entertainment. And that doesn't
Starting point is 00:42:30 mean that you have to be that person, but that's how I lean into who I am, because I don't want producers or directors to tell me to be something else because they'll say things to me like, finish your drink, your night off with a scotch and a night clap cap. And I'm like, but I don't drink scotch. And normally I drink water out of the bottle. I'm just being polite. But I'd rather drink wine out of the bottle than the glass because I'm a germaphobe and I don't like germs, so I'd rather to go to the bottle. So it's really hard to sometimes let people be yourself.

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.