From Single Mother to Billion Dollar Founder with Dr Ann Kaplan Mulholland

0:00I never talked about being a single mom with two kids. They did not know. No one knew how much I was struggling. I just appeared successful, but I never said I was successful. I just appeared successful. Dr. Anne Kaplan Mulholland, an award-winning entrepreneur, investor, author, TV personality, and real estate mogul. When it comes to the business side of it, when I started to be an entrepreneur and started a business, it was figuring out how to raise funds at the same time you're figuring how to do your operations. So I pitched, I guess, 30, 35 investment banks. The door slammed on all of them.

0:36When you're an entrepreneur, when you are successful, even if you start a business, you need to differentiate yourself. Nowadays, if you ignore the media channels, TikTok, Instagram, Facebook, if you ignore that, you are not building a business. You are irrelevant if you are not on social media. You actually don't exist. Welcome to Screw It, Just Do It, the show for those who decided to screw it and just did it. This is the podcast that brings you face-to-face with the entrepreneurs and business rebels who threw caution to the wind and built something extraordinary. Let's start with something that might come on their radar really soon, which is a TV series.

1:12So let's start with the castle. Can you tell me what made you take the leap to buy and rebuild a 1 ,000-year-old fortress? And how does it compare to everything that you've built previously? So it's interesting that you ask that because it was not something that was planned, but I've always been extremely hardworking and very focused and I've built many businesses. And it's about removing that can't do and then can't to the can do. So there has to be a reason why you're building a business, why you want to take something from scratch and do it. And I find that often people look at something and they say, I've got this really, really good idea.

1:53And then they go for it. But if you reverse engineer your distribution channels, and you say, how am I going to distribute my idea? And then you go back to your idea, you will change your idea and you will be better at business. So you can be an entrepreneur, but being a good business person and entrepreneur, being successful and being very successful are different things. So when I have been building businesses, I look at the how am I distributing? How am I getting people to my business and the purpose of it? And then I go backwards. So in historically building a finance company is how am I going to distribute it?

2:33So obviously it was through, we did medical procedures, dental, veterinary, home improvement, et cetera. how did I distribute my finance products? And that was loans. So I looked at, I'm just going to loan money. So the idea was I'm going to loan money, but how do I get people to borrow from me? So what we did to simplify it is went out to doctor's offices and said, instead of your patient coming in and saying, I need veneers or my pet has emergency surgery, I don't have 5 ,000 pounds or dollars, or you go into the plastic surgeon and say, for one of the biggest ones was, I need breast implants.

3:15And then they say, well, that's going to be 7 ,000 pounds or$7 ,000. We went out to the doctors and said, why don't you offer your patients our finance product? And then instead of saying it's 7 ,000 pounds or dollars or 7 ,000 pounds or dollars for your dog to boat emergency or 4 ,000 pounds of dollars for whatever home improvement you want to put in a new toilets and you don't have the money. These were unsecured loans. But so the patients would go into the doctor's offices. We didn't market to the patients. We marketed to the doctors. So in the end, I ended up signing up 16 ,000 doctors and they, all of them offered our financing to their patients.

3:55And then we did a platform where patients could ask questions. So you might be saying, I'm thinking of getting a hair transplant. So not you, but someone might be saying something like that. And then they say, so often men will have what they call just a little bit of receding hairline, but not full on loss. They might be saying, should I get an incision where you can just pull the hair together or should I get plugs? So then they would ask that question on our website. So we had a separate website and then we signed up the same doctors on a separate website, not the finance one, who could answer questions.

4:35And those doctors would get more patients because they'd start answering the questions for the patients and the patient would be plugging in by their postal code. So the doctors would get more business. So you have to think not about the idea, it's how do you distribute it? And how do you satisfy the channel that distributes your product through? It could be any product. And you don't have to come up with the idea initially. But if you come up with the idea, you figure out your distribution, then how do I hold on to it? How do we get better than the competitors that come out there? And you're building their businesses at the same time for them as well.

5:15So it's win, win, win. And you start out and you know you're going to have competition, but you just keep improving and getting better and better and better. And if you ignore nowadays, if you ignore the media channels, TikTok, Instagram, Facebook, YouTube, if you ignore that, you are not building a business. You are irrelevant if you are not on social media. You actually don't exist. you are it's like you're having a conversation all of a sudden you say something and then it's like more there's nothing because you don't matter if you're not on social media yeah people can't find you absolutely and if they can't find you or your business then that's not you don't have a business so in historically when i was building businesses i thought uh well what happens because I'm an entrepreneur.

6:05What happens as I get older and I'm not working anymore? I can't pensions. I don't get any kind of anything because I'm self-employed. And so I thought, okay, what do I do? And I started to, I had five offices across the country or national and international business. The bank said to me that, you know, if you buy an office space, then you can put your office in there and we'll finance it because I would be owner operated for, um, for my business. And so I went out and looked at an office space and it was at the time, I think$5 million. And, and then I found another office space and I went back to them and said, you know, there's a building that's$5 million.

6:52And I found two and they said, well, you have, you have enough revenue. You can actually buy both. So I started buying buildings, commercial buildings being owner occupied and putting tenants in there. And I would buy the buildings, put just enough down that the leases that came in covered the debt, the mortgages. So it wasn't residential real estate, it was commercial, but I was buying it. So just say 5 % down and then just say 95 % would be covered by the tenants in the building. And so I started to buy buildings and then I started to buy residential property, renting that out through agencies.

7:30And then I thought, if I'm going to buy something, I want to like it because I did multiple degrees and my first degree was interior design and I love really nice things. So I went to, I started to buy buildings that I loved and properties that I loved that were pieces of art. And one was very Japanese like, and so I did it all Japanese decor through it. And one had First Nations, which is Native Indian, and it had all these totem poles and First Nations paraphernalia from the last company that owned the building and throughout the building. And then just after we had closed, they came to me and asked if I wanted to buy any of the art.

8:12And I said, I'll buy it all. So I bought a whole collection of art, which were big kayaks and totem poles. And then I've done the building and kept it around the First Nations theme. And is that all in Toronto? No, that's in Vancouver. Okay. And then I started to buy properties in the US and like Hawaii and then theme it. So when it came to, we moved to England and became residents. Now, these are all income earning where the cost is meeting what the revenue is meeting. The cost and the revenue are equal. And so you always want to have debt on, I don't have debt on all the buildings, but you'd like to have debt on the buildings because then you're not paying interest on the mortgages.

8:58So you have to weigh that out. But then eventually after 25 years, I paid off all the buildings and all I have is revenue. And that was the idea. When it came to the castle, we had moved to England as residents and my husband and I respectfully left our businesses. Our youngest of six kids moved out and went to university in the States. We dropped them off and said bye we're moving and we had no more business and we were still young and their kids had all moved out and my husband and I said there's we've the world is our oyster let's go live life and with flights and things we can visit our kids they're scattered all over all of them university or finished all of them very very um uh very good people they're they're not concerning individuals.

9:46They're people of value, I would say, meaning that they're just nice kids. And so I was never worried about any of them. And we decided since my mother's English and my husband's Irish, we'd move to England. And I did my doctorate and my master's of science at Hanley Business School. So I'm very used to coming to England. So part of the requirement was that you had to lease or buy your home. So when you're non-resident, you move as a non-domsile resident, we came in on an ancestry visa, the algorithm or the checkbox, you need to lease or rent, you can't stay in a hotel or something. So I said to my husband, having done a lot of real estate, that I felt, this is three years ago, I felt the interest rates were going to go up.

10:32I felt we were in an inflationary market and that it would make no sense to buy real estate in England. It's just going to, even if it goes down by 10%, you've had a 10 % loss. And what we looked at a few apartments and the entry level in London was 8.5 million pounds for an apartment and 45 ,000 or 48 ,000 a year for the fee that you pay when you live in an apartment building, like a flat for the front desk and the concierge and that. So we were looking in Belgravia and Knightsbridge and Mayfair. So I said to my husband, let's just go rent a place and then forget buying everything. 8.5 million pounds, no way.

11:21I'm not spending that on an apartment that could depreciate. And then I, so we just rented. We didn't buy. And then I thought, everything's so expensive in London. Like this is insane compared to the rest of the world. So I thought, I wonder what a house costs. So I started Googling and I thought, wow, a house on the outskirts of London is cheaper than an apartment. And then I Googled more and there was this castle. And I thought, this castle is cheaper than the flat in London. That's crazy, isn't it? Yeah. London. So I just out of curiosity, had no idea, no intention of buying a castle. I texted the broke her and he didn't respond.

11:59So I just dropped the whole idea. So we're going back less than two years ago. And then I had hosted three TV shows in Canada. And then I was on the Real Housewives of Toronto. And I'd always loved TV because my brain is more like more math, but I like the creative side so my doctorate was in writing algorithms and finance and my master's of sciences and finance my mba is in finance but i also did interior design and so that there's i need to satisfy both sides of the brain i like the creative but i'm actually anti-social and not like really really i really keep to myself very private um but i love creative so that when you'd like that and you you're asked to do a lot of tv shows i was asked to do these shows um probably because i'm weird anyway they've so they had asked me to do a show actually my own tv show on entrepreneurship in canada and i they wanted it to be entrepreneurship for women and um i said i don't think you need to be a woman and what's the difference if you're a woman or a man you're either good at what you do or you're not.

13:18And I don't care if you're, what race you are, what your preferences are, you get over all those things. Like get over the challenges. We're all different, but I didn't want to single out female entrepreneurs unless it was in a challenged country where women weren't allowed to work or they wouldn't be paid. Then that would be interesting. But I said, okay, I'll do the show because they really wanted me to focus on women. And then this simultaneously less than two years ago, I'm up and it's been greenlit for a TV show. And six weeks later, approximately, this broker calls me, texts me and says, hey, that castle was sold under sale and the deal fell through that I inquired about.

14:05I said, do you want to come go and look at it? So we're going back November 2000, I don't know what year we're in, 25, 23, 22, November 2022. And I said, yeah, I guess I'll go look at it. It had been under sale for 11 million pounds. And the assessment was close to 40 million pounds. And the replacement value on the insurance is 35 million pounds or vice versa, one of the two, 40 and 35. But it was the sale market. Of course, we're in a bad inflationary market. You cannot get a loan on a castle. It's just too expensive to run. And there's not a big market for people buying castles because the operating cost is so high.

14:49So I said, okay, I'll just come and look at it, but I'm not interested in buying it. I'm curious, what does a castle look like? So I said to my husband, let's go look at this castle tomorrow. And he said, we're not buying a castle. And so we drove down to Kent and we looked at the castle and just absolute disaster. It had not been looked after in 30 years. It had furniture piled up upstairs. It was awful. we actually videotaped all of it going in there there were dead animals in the pool area which was a pond like dead fox and it was just awful and there was all the floors were peeling up and things but the the stone structure was nice and so I looked at them and I said okay we'll we'll buy the castle without consulting my husband I was about to say his reaction was and and I said we'll buy the castle, but we're only giving you 6.5 million pounds, half of the other offer, take it or leave it.

15:52And so I thought, if I'm going to buy this, and I'm going to invest this much money in it, I might as well offer lower. And if they don't want to take it, don't take it. But I knew it was a tight market and they took it begrudgingly. So then we went under survey. And one of the things that when you're an entrepreneur, you always have to figure out how to fund all your operations. And so this is still entrepreneurial to buy a castle because I've got to fund the operations. And so why not? They had a wedding venue. They'd never been open to the public or anything, but why don't I reopen and put a wedding venue in?

16:30I didn't buy the business because that would be buying an operating business. I only bought the wedding. I bought the castle, the bones. But at that point we had a survey. So I called up. So back to doing the Entrepreneur Show for Women, I called up the production company and said, you know, I've got an offer in a castle. Wouldn't it be interesting to do a show about renovating a castle? So there's my distribution. If I got picked up to do a show about renovating a castle, then I have my distribution and my marketing is paid for. Yeah, I was about to say, so the marketing is paid for and you're building the audience who would want to yeah exactly so then i got a call in february 23 the end of february 23 it was a friday and i got a call from one of the producers and he said guess what your show got picked up in the u.s and investors and um it's a go queen of the castle the name the show has been picked out great but we hadn't closed on the castle and we got in the same day the survey report back oh what does that look like this thick plumbing the what's whatever that's called foul drainage the electrical the bats the rats the beetles the the oil tanks the water heaters the radiators everything had to be replaced and so i said to my husband there's no way we're spending 5.5 million on this castle, 6.5 million on the castle.

18:06And so I went back to the sellers and said, all right, no, I got the call that our show was picked up. But I went back to the sellers and said, the survey report, you didn't disclose this when we were making the deal, how much damage there was. I will buy the castle and give you cash tomorrow morning at 10 a.m., but I'm taking a million off, I will give you 5.5 million. It's more morning, 10 AM, take it or leave it. And they said, F you. Am I allowed to say F you on your podcast? They said, F you. So I'm sitting with my husband that night and we're at dinner and he, I said, the show got picked up.

18:40That's the good news. And I said, the other is, is that I took a million off the price because there's so much damage and it's going to cost at least that just to fix the roof tiles is a million because you have to surround the whole castle with scaffolding and et cetera. So that's a million just to fix the roof tiles. And I said, the bad news is that it took a million off the price. And he said, just phone them up and tell them you're going to give the 6.5 million. I said, no. I said, just wait, the phone will ring. And so we're sitting at dinner and he was like this, like, just give them the other million.

19:13And I said, no, just wait. So 10 o 'clock that night, they phoned back and the broker phoned back and goes, they're taking it. They were mad. and I had to wire 10 a.m. the next morning 5.5 million pounds and we got the castle. No I was actually being honest because that it it is a lot of money to renovate a castle so now we had this show which is now we picked up in seven countries now we're on our second season just finishing it we've got the show the distribution and then you have to differentiate yourself so when you're an entrepreneur when you are successful even if you start a business you need to differentiate yourself and so the show is very quirky it's very funny and um it's you you know in all the episodes I'm wearing a tiara and a gown and I'm out working the diggers and helping the the people working at the castle and we're building our businesses we've opened restaurants, we've opened the wedding business, we've got an event space, farmer's market, all that kind of stuff.

20:22And all of it shows all of the challenges of opening a grade one list of building and expanding operations. And so I think being an entrepreneur and knowing how do you market, how do you do TikTok, Instagram, you have to understand your TikTok and Instagram to be able to market yourself. And you have to market yourself, your personal brand. When you're an entrepreneur, you will be more successful as having a personal brand and learning how to market that too. So just differentiate yourself personally. And so most people are like, no, I don't want to do that. It's just black and white. I am not going to go out there and be as flamboyant.

21:05That's for you, Anne. I don't want to do that. But the difference is when you do do that and you become a brand unto yourself and your true self, you get more attention than if you want to just fall into the wallpaper and blend in. Because you have to think about marketing your personal brand. And I don't like doing social media. It's the least favorite thing that I could ever do. But I know if I don't market social media, that people will look me up. And if I'm not on the internet, they can make assumptions. But if I don't do too much, then they find things that I don't want them to find. They might find me without makeup on and someone's taking a picture or something like that.

21:48But if I market myself in social media, wearing weird gowns and doing funny little skits, that's what they're going to find. So I don't put out, you won't find much with my children because I'm private in my personal life. I don't put things out of who my friends are because I don't want friends that want to do Instagram pictures with me. I like my friends to myself. So you don't see me with friends. You don't see my social circle unless we plan to do something. And you don't see my children unless they want to do something for a one-off with me. But what you see out there is me in a gown or me doing a funny skit and that's the end I want people to know not the end that is the real and the real and so being an entrepreneur you need to define your brand you need to be okay doing tick tock and instagram and you need to figure out how to do tick tock and instagram and you know that means in tick tock how long are the clips and so you probably 15 second clips but how do I grasp someone.

22:56On TikTok, you got to grasp them in the first second. You've got to get people and you've got to keep them engaged. And on Instagram, it's more, you got a little bit longer, you can go a minute and 20 seconds, but it better not be boring. And you've got to figure out how to engage people. And so both of them are videos should both be reels and not horizontal, vertical reels and you need to be engaging and people are don't want to look at photos anymore not much photos they want to look at um things moving and they want to be entertained and they don't have an attention span longer than 10 or 15 seconds so and what did your what was the reaction of your um of your kids like in general was it uh kind of one reaction from the six of them or varied reactions when we buy castles and things like that yeah and the tv show yeah uh they really are not interested in the castle you know they they went like oh cool and they've come out to visit but um we own i don't know 14 or 15 properties worldwide and they're all over the top and so the castle is one of those that's over the top we and it's the things that we offer the castle The way we decorated is very much like a castle with knights in shining armor.

24:17Some of them are pink and some are orange and some are green. And some of them are drinking beer and some of them are doing like a selfie shot like this and they're holding an iPhone. These are the knights. So there's really fun, quirky things. Yeah, because in those things, if someone is offended and say we do a wedding at the castle, we can move the knights out of the way. But for example, one wedding, a woman who loves orange and pink married a military Gurkha. And so we had the Gurkha shield put on one of the knights and it's in green and she's in orange. And we set that up at the castle. And it was just a nice little thing we can do for brides and grooms.

25:01With all these colorful knights, somebody had a pink wedding. and I ran into the couple of the castle and I said hey we've got all these pink candlesticks would you like those at your wedding instead of the white ones and they're like yeah and then they said hey what I've got a pink knight upstairs do you want the pink knight and so you can put the pink knight and the knights have all been deconstructed and they're like mannequins inside that have flexibility so you can close their hands and the staff always gets puts the like does the finger with the knights so i'll be walking by and the knights like this is it we're closing the not when the not when people are in there but the knights can be holding the flowers in their hands so you can have a pink knight and a bouquet of flowers and it can match the bride's dress and so we look at fun things to differentiate my kids on the other hand are like mom you know like really and they're they they have always done things like can you act like a mother and it's like well like I do act like a mother I cook the meals and things but why can't I why can't we have children and why can't we have fun it's not like I'm hurting anybody I just love comedy and it's um I've done a lot of stand-up comedy and that stand-up comedy came with doing a lot of public speaking.

26:24And I learned that if you take standup comedy lessons, it helps you to engage an audience better. Because when you're doing standup, you've got to read your audience and you've got to every word you say counts. You set people up for a joke. And so I started to take standup comedy to help my public speaking. And then I mentioned that to Sick Kids Hospital I was doing a fundraiser and they asked me to speak to women entrepreneurs and I did. And I said, during COVID, so it was online. And I said, do something for yourself. For instance, I do stand-up comedy and I do an online course. I did in person and during COVID I did online.

27:10And then Sick Kids came to me after and asked if I would compete in stand-up comedy. And I went, uh-oh, like I've never, never at that time did it. And so I started to take lessons in London, the Bill Murray studio and did standard comedy courses and then private training and just absolutely fell in love with the challenge of standard comedy. And then I performed and competed and did all that. And it's so hard. But in that, I talked about what was true to me, and that is raising six kids and keeping my husband entertained. And my children were mortified that I would talk about raising children.

27:54And, you know, it was talking about taking the boys and giving them all a box of Kleenex and some hand lotion and just leaving them in their rooms during puberty. And they're like, Mom, how could you do that? Yeah, you've got to say that. Well, you can, because everyone would relate to it. If I said my kids were all normal and good, no one would believe me. If I said I put the box of Kleenex in the room, the hand lotion, when I have four boys, and that's what I did, they would believe me. They'd relate to it. So I think the kids don't like the truth because they didn't say, mom, that's not true.

28:33they said mom how can you say that so are we supposed to not like the funniest thing in life is the truth so comedians tell the truth and they except for maybe jimmy kimmel now but i think they get away with the truth where if you're a serious public speaker and you're not joking you you can't say what a comedian can say because you, at an entrepreneur show, you can't say what a comedian would say if you're talking about business, but a comedian can say the same thing and make a joke about it and get away with it. So put comedy in your life. And I did even when I was in finance, I still put comedy in.

29:17When I had a meeting with bankers, because I was always in raising money to loan money, I had someone in the corner going, show me the money, show me the money. And we did things that just made them laugh. And people love to laugh. You've got to be serious about your business. Don't take your business too seriously that you can't enjoy doing it. How did you start yourself then, like initially to go like, you know, way back? You've built these businesses now, but for people listening who are maybe sitting on an idea and maybe they don't come from money or the right background or privilege, what advice would you give to those people who are just, you know, sitting on that idea and not taking action?

30:02So I was a single mom with no money, no support from my ex-husband. His name was Gone with the Wind, by the way. And no support from Gone with the Wind and two babies, two little children. And I had an idea and I worked full time. And the only way that I could make it work was to do work because I had to pay the rent and start my business simultaneously. And I think often when I see entrepreneurs or speak at a conference or something like that, someone will say, you know, they can't afford to do this. They can't afford to do that. They want to have this car. They want to get married. They want to have kids.

30:49Well, if you want to be a true entrepreneur and take risks, you're going to have to focus on the business and all the other things you've got to put to the side. Now, I already had kids. I couldn't just go, okay, I'm going to return them. And so you've got to figure out how to make it work. So I was doing night shifts to after the kids went to bed, I rented out a room. So you solve for each hurdle. I rented out a room in my rented apartment to somebody that would come in after eight o 'clock when my kids were already in bed and they would be there at the apartment. So they rent out the room. They would be there at the apartment when I went to work at night.

31:26So I did night shifts and somebody was with the kids and I had them trained so they didn't wake up during the night. But if they did, they could call me. So I had to solve for that. I had to solve that I couldn't afford much. So that renting out the room did that. And then my kids wore clothes that I bought at the discount places and like t-shirts and jeans. And I mean, they weren't wearing designer clothes. I was buying secondhand clothes so I could wear a suit to work and who cares? And it was, you just have to figure out for that. Now, when it comes to the business side of it, when I started to be an entrepreneur and started a business, it was figuring out how to raise funds at the same time you're figuring out how to do your operations.