Transcript
From Single Mom to 2 Billion how Class and Courage Win - Dr. Ann Kaplan Mulholland
From The Proven Podcast · Episode page · Watch on YouTube
· 1 h 13 min · 14,266 words · 138 timestamped sections
This is the full, timestamped transcript of "From Single Mom to 2 Billion how Class and Courage Win - Dr. Ann Kaplan Mulholland", an episode of The Proven Podcast published January 14, 2026 (1 h 13 min, about 14,266 words). It mentions 24 people, works and ideas, including Single Mom, Jeffrey 71st – Miller, Charles, Women Entrepreneurs, Commercial Real Estate, Small Ticket Loans.
What this episode is about
Dr. Ann Kaplan Mulholland shares her inspiring journey from being a single mother to building a $2 billion empire, highlighting how resilience, class, and authenticity are key to overcoming challenges and dismissing societal doubts about success. Her story emphasizes the balance between motherhood and entrepreneurship, showcasing the importance of embracing one's intelligence and capabilities.
Key takeaways
- Success isn't just wealth; it's knowing how to balance motherhood and ambition while thriving in both.
- From single mom to $2 billion empire builder: sometimes setbacks fuel the greatest comebacks.
- People define you by your bank balance, but real success starts with who you are at your core.
- In a world that sees wallets, be the person behind it – values over visibility.
- Real happiness lies in relationships, not revenue; money may fade, but connections define legacy.
Who speaks in this episode?
- Dr. Ann Kaplan Mulholland (Guest) · 58 min speaking
- Charles (Host) · 15 min speaking
What is discussed, and when
- – 10:00: Single Mom, Jeffrey 71st – Miller, Charles, Real Estate Portfolio, Small Ticket Loans
- – 20:00: Single Mom, Jeffrey 71st – Miller, Charles, Small Ticket Loans, Brexit
- – 30:00: Harvard, Women Entrepreneurs, AI, Women in Business
- – 40:00: Queen of the Castle, MIPCOM, Jeffrey 71st – Miller, Charles, Women Entrepreneurs
- – 1:00:00: Commercial Real Estate, Jeffrey 71st – Miller, Charles, Small Ticket Loans
Notable quotes from "From Single Mom to 2 Billion how Class and Courage Win - Dr. Ann Kaplan Mulholland"
Can prove. On this episode, we talk to a queen and walks us through what it took to go from being a single mom to building an empire that's worth over $2 billion.
about Single Mom · atI'm a mom but there was to me from building that and then investing in real estate portfolio and then I continue to do that. On the other hand, I have more of a brain that is more mathematical but also a creative brain.
about Real Estate Portfolio · atStart to cuz I'm friendly also. So think they mistake friendliness as being naive and unfortunately Charles they mistake being female as being naive and that like it's always…
about Women in Business · atIt and I did my research before I would approach the banks to invest with me and because in money lending you need banks behind you and I had this air of doing it but I didn't…
about Small Ticket Loans · atAnd so Charles, I would not do any kind of vodcast or podcast or YouTube channel if I didn't trust the person that I'm doing it with. And that's a compliment to you because I live forever.
about Jeffrey 71st – Miller, Charles · atHave to think all the people you don't know that is going to buy into your idea and think even bigger. And then right now, you've got AI. If you're not thinking of…
about AI · atTalking about the kids and things like that, but not about business. And so, you to realize that a big thinking woman is going to be a threat to men. So, you have to be aware…
about Women Entrepreneurs · atThis current market. I would wait if you don't have the free cash to do that. But real estate commercially is also on a decline because people are working out of their home. A…
about Commercial Real Estate · at
Who and what is mentioned in this episode?
People
- Jeffrey 71st – Miller, Charles — Person · Host (named in-episode) · 4 mentions · first at
The guest addresses the host as 'Charles' repeatedly; he guides the interview and frames questions on women, branding, and scaling.
Books & papers
- AI diploma course — Book · Referenced education program · 1 mention · first at
The guest uses her enrollment as an example of 'get educated' and staying competitive as AI reshapes business.Missing the boat because that is really big right now. So, so I signed up to take a course, a diploma course at Harvard in AI. And so I'm going, I don't know enough about AI. I get it.
- Corporate Governance — Book · Referenced credential · 1 mention · first at
The guest lists a corporate governance designation among her education, supporting her credibility in business leadership and oversight.School got an MBA and a masterers of science and a doctorate in writing algorithms and a corporate governance designation and I also did an interior design degree. So there was a balance there.
Companies & orgs
- Harvard — Company · Referenced organization (education/upskilling) · 3 mentions · first at
Harvard is cited as the institution offering the AI diploma course the guest enrolled in; the host also references being in the same course.I think one of the things you said there was like not thinking big enough. And I think you and I are both in the same Harvard course right now. But this isn't, you go in and you do it. And we're constantly working on it.
Products & tech
- AI — Product · Core topic · 1 mention · first at
AI is framed as a major business shift; the guest urges entrepreneurs to incorporate AI and upskill via formal education. - Tiaras — Product · Branding prop (example) · 1 mention · first at
Tiaras are used as a memorable marketing tactic at MIPCOM to make the guest and her show stand out.TV show conference in Khan, and my TV show is called Queen of the Castle. I brought a whole bag full of tiaras and we handed out tiaras to people and I literally brought drag queens with me because I was the queen and dressed.
Concepts & topics
- Single Mom — Concept · Core biographical theme · 5 mentions · first at
The guest’s origin story centers on building businesses and raising children as a single mother, shaping her discipline, delegation, and risk management. - Women Entrepreneurs — Concept · Core topic · 2 mentions · first at
A large portion of the episode gives tactical advice to women on confidence, preparation, networking, and handling bias/harassment in business settings. - Commercial Real Estate — Concept · Core topic · 5 mentions · first at
The guest comments on commercial real estate decline due to remote work and suggests alternatives like warehousing and office-to-residential conversion. - Small Ticket Loans — Concept · Core biographical/business topic · 3 mentions · first at
The guest’s first major company was built around small-ticket unsecured lending, which she scaled to $2B and later sold. - Women in Business — Concept · Core topic · 2 mentions · first at
The episode repeatedly addresses gender dynamics in business—credibility, being underestimated, and navigating inappropriate behavior. - Real Estate Portfolio — Concept · Core topic (wealth strategy) · 1 mention · first at
The guest describes building an income-producing portfolio (14+ properties worldwide) as an annuity-like safety net. - Hospitality — Concept · Referenced business domain · 2 mentions
Hospitality appears through the castle business model (tourists, weddings) and operational systems (booking platforms).Tourists... want to visit a castle and a bride and groom.
- Motivational Speaking — Concept · Referenced career component · 1 mention · first at
The guest describes speaking via a bureau and how that public-facing work led to TV hosting opportunities.But I also ended up speaking at different platforms and speak with the National Speakers Bureau and do motivational talks. And in that I was asked if I wanted to do my own TV show.
- Motivational Talks — Concept · Referenced activity · 1 mention · first at
Motivational talks are part of the guest’s speaking career and contributed to her visibility and media opportunities.But I also ended up speaking at different platforms and speak with the National Speakers Bureau and do motivational talks. And in that I was asked if I wanted to do my own TV show.
- Financial Statements — Concept · Referenced business artifact · 1 mention · first at
Financial statements are mentioned as a hurdle early on when proving credibility to banks while building the lending business.Overnight. I started the company. I always had an air of success like I could do it but you know when somebody is looking at your financial statements you haven't met there yet…
Places & events
- MIPCOM — Event · Referenced industry event · 2 mentions · first at
MIPCOM is used as an example of high-stakes networking/visibility tactics; the guest describes handing out tiaras to stand out.Searching to sell or buy something. And so I make sure that I make myself noticeable. And so for example, when I went to MIPCOM, which is the reality TV show conference in…
- Brexit — Event · Referenced macro event · 1 mention · first at
Brexit is referenced as a cause of skilled trades leaving the UK, affecting renovation labor availability and costs.Difficult. And I don't want to get into anything political, but if I look at anything about me living in the UK when they had Brexit, a lot of the talent and we're renovating a castle in England, a lot of the talent has left with Brexit.
- Ontario Economic Summit — Event · Referenced networking forum · 1 mention · first at
Cited as a committee/organization the guest joined to expand her global network and credibility.Thing that I do, and I try to tell this to my kids, is join organizations. So, I enjoyed the Ontario Economic Summit for years. I was a delegate and the G20 Y on the banking…
- Toronto — Place · Referenced location · 1 mention · first at
Toronto is referenced as the setting of the Real Housewives series the guest joined.Shows and then oddly picked up by The Real Housewives and became one of the Real Housewives of Toronto.
Media & podcasts
- Queen of the Castle — Media · Referenced TV show (guest’s project) · 2 mentions · first at
The guest’s reality/TV project is used to explain branding, distribution, and how she markets herself at industry events like MIPCOM.And I was ended up being starring in a TV show that's going into its third season and aired in seven countries. So, there's a balance of how do you describe yourself? I'd say if at the end of the.
- Proven Podcast — Media · Podcast (episode platform) · 1 mention · first at
This is the show hosting the conversation; the guest later instructs listeners to reference the podcast when messaging her.Welcome to the Proven Podcast, where we don't care what you think, only what you can prove. On this episode, we talk to a queen and walks us through what it took to go from being a single mom to.
- The Real Housewives of Toronto — Media · Referenced TV appearance · 1 mention · first at
The guest cites being cast as a Real Housewife as part of her media trajectory and public profile.So, I ended up hosting three television shows and then oddly picked up by The Real Housewives and became one of the Real Housewives of Toronto.
- Real Housewives — Media · Referenced franchise · 1 mention · first at
The franchise is referenced as the platform that picked up the guest and expanded her public profile.So, I ended up hosting three television shows and then oddly picked up by The Real Housewives and became one of the Real Housewives of Toronto.
Full transcript with timestamps
Welcome to the Proven Podcast, where we don't care what you think, only what you can prove. On this episode, we talk to a queen and walks us through what it took to go from being a single mom to building an empire that's worth over $2 billion. She was told that she wouldn't amount to anything and she could never do it on her own. She didn't take that as a war cry. She took that as a challenge. one that she met with class, integrity, and a level of authenticity we rarely see. The episode starts now. All right, everybody. Welcome back. I'm crazy excited to have you on the show again.
Thank you so much for being on the show. Thank you. So, it's rare that we run into people who balance not only work and life, but also energy and success. And you're one of the people that when you came across this, I was like, I absolutely want you on the show to share some of this. But there may be four or five people on the planet who don't know who you are. So let's talk about who you are and get the audience up to date.
Well, I mean, how do you say who you are? If I describe myself, I'd say I'm a mom because really most of my life I've raised six, eight, 10 children literally. And it's been that's who I am as a mom. But there is no be a business person as well. So I was a single mom to start out with and I formed a company that um was in financing. So small ticket loans, unsecured loans and built that up to $2 billion and um sold the company at the m in the meantime I invested in real estate. Now I had to balance that with kids. So I still say I'm a mom
but there was to me from building that and then investing in real estate portfolio and then I continue to do that. On the other hand, um I have more of a brain that is more mathematical but also a creative brain which I think when we analyze ourselves we shouldn't be ashamed to say like I'm smart and I mean as human beings we don't want to say I'm intelligent but I am
and so if I don't think we should be ashamed to say our attributes and the at the same time I I went to school got an MBA and a masterers of science and a doctorate in writing algorithms and a corporate governance designation and I also did an interior design degree. So there was a balance there.
Mhm. But I also ended up speaking at different um platforms and um speak with the National Speakers Bureau and do motivational talks. And in that I was asked if I wanted to do my own TV show. So, I ended up hosting three television shows and then oddly picked up by The Real Housewives and became one of the Real Housewives of Toronto.
Mhm. And I was um ended up being starring in a TV show that's going into its third season and aired in seven countries. So, there's a balance of how do you describe yourself? I'd say if at the end of the day, if I was a good mother,
I would proud and a good daughter and a good friend, I would be proud. So, I'm a mom, but there's and to as to all of us, there's so many more aspects of who we are.
I I think it's really interesting as I see successful entrepreneurs, there's a difference between those who describe their success by their finances and those that describe their success by who they are in life. And I spent about eight years in a hospice watching people die. And then people that were the happiest, they always started with, well, I'm a mom or I'm a husband or I'm a wife or I'm a sister or I'm a friend. They always start with that. Oh, I happen to have made all this money, but what really matters at the end of the day is
who you are and what fills your heart. And I think, you know, before we started recording, we were talking about balance and how important that is. And I think the way you describe yourself hits that on a high level, but I don't think people really understand because they look at someone like you that's had all of this success and they don't know the the other side of it. And regrettably, you know, there are people online who are unfriendly and they don't see the other side. So for me, when you talk about
that's interesting cuz people look at me when I meet them and I realize that they don't see me, they see a wallet. So, I'm like this this dollar sign to them and I'm talking to somebody and I think, oh, I mean, they want to sit next to me and they're chatting and they they think I'm nice and I like to be entertaining and then I realize there's an ask that is going to come and it's a rude awakening that I have to be aware of but not let it consume me. That maybe that in between all that I might meet a few good people that aren't on the ask. And so when you describe yourself, I I don't describe myself with money because if that money goes, then I still want to be living on my values and I don't want me as having money even though I have money. But that's so irrelevant to the person that somebody is.
It really is. And I I think it's important that people learn how to do this balance, how to how to find the difference and find out what matters to them. And you went through some trying tribulations before with when you had some stuff that happened. You're like, "Okay, well, I'm going to go do this anyway, even though I'm a single mom and I'm rocking and rolling at the time."
Could we talk about a little bit of that, what balance looks like and how you do survive some of these times where people regrettably see you as a wallet versus a human being? It it's now with opening different businesses I have to explain to the management that when somebody is giving a quote it is important that they present themselves as the managers if I'm attached to that. So I try not to market myself in conjunction with my businesses. So I have a commercial building. I have managers and I have to explain to them do not associate me with the building because then people will start to cuz I'm friendly also. So think they mistake friendliness as being naive and and unfortunately Charles they mistake being female as being naive and and that like it's always she she rather than the owners
and they will emphasize the she and they will get to me. So, I have to explain to the managers realize that they are looking at my wallet and they're looking at getting a deal because there's a female behind it and because they show money. Now, that aside, there's nothing I can do when I meet people and they do that. I just have to be aware and almost almost put up a careful barrier
and make it very apparent that I'm not going to be investing in somebody's new idea or something like that to so because that often follows with by the way I have a I want to make pies in my home and would you invest in and so I always have to be very careful to say um I invest in what I manage. I think there is this perception that if you're a female, you're nice, but also that you may be weak. And I have found that the the blessings that I've had of working with entrepreneurs who are female, most of them have leaned into that as an advantage. Like, oh, you're going to underestimate me. Oh, this is going to make my life so much easier now because I have this competitive advantage now because I get to come in and I get to surprise you. Instead of saying, oh, well, I am this perception.
because you're we're not what other people think of us. But to reach the levels of success that you've had and raising as many kids and going through those trials and tribulations, how do you find those balances? Like what's the practical you suck? We talked about you're always up early and I was like, I I'm not. How do you how do you do that?
Well, I have to get up early and I was trained when the kids were little. I'd have to get up and do whatever I needed to do before I drove them to school. I would have a shower. I'd get up. I'd do what I needed to do. And if I was studying, it would be studying. I would get the kids ready. I had to organize the kids so that they could get their own breakfast and they made their lunch the night before. They made their lunch the night before. When you have a number of kids, you have no choice but to train them
and then get in the car. I'd have a shower, my hair would be wet, drive them to school, and then I would go hairdresser to do my hair in the morning while I worked and then went to the office. So I'd be at the office by 8:30, 9:00 in the morning. So it sometimes 9:30 depending on the day. And so then I'd have my full workday, not take a lunch because I needed to put that 8 hours in. In finance, you really need to be at a desk and put that time in. And having a lunch was I'd rather go home an hour earlier than uh and eat somewhere. And so I'd bring my carefully pack my lunch or I'd allocate whatever $5 if I'm gonna buy something. So I budgeted on my lunch.
Even now I budget and I could buy the restaurant and that's not a like I would buy a press just to have the broccoli every day like delivered but I do watch every every single dime to this day. Gota. So, it sounds like you started delegation, not even at work, but also at home. You're like, "Okay, listen. I've got to empower the people underneath me, even if they're my kids, that I can only accomplish ABC. I only have so much energy and so much time in the day. I need to view my time as a resource as much as I view my my finances as a resource, and I need to delegate downstream." People have a hard time doing that in business. That's very challenging, especially now. and they're all like, "Oh, well, millennials this or Gen Z this or whatever it is." You did it with children. So, it kind of negates that whole argument that it can't be done. How do you delegate properly when you are having this level of success and
you're raising kids and you're getting married and you're a single mom and you're getting your doctorate and you're doing all this, how what are some tactical ways for the people who are listening that are, you know, running companies, how do you delegate crop? So I assume that people have a certain limitation to their talent and I try to look for the talent that each individual has that I hire and I don't try to fit a square peg in a round hole. If somebody is really really good at sales, do the sales, but don't take someone who's very good at the front desk and greeting people and put them in sales. Make them the best greeter and then depend on that for for them. I believe strongly in also a spiritual culture. So you pay people fairness and fairly and then you invest in the culture of your organization whichever your organization is. So it's a happy workplace. I would let go of anyone who talk negatively about
somebody and I hire for skills. I no I look for the skills and then I hire for values. So it's important and then I get rid of them really quickly like within 3 months if they are rude if they hit on somebody at work if they if there's anything that they do and I would fire anybody who stole from the company and so that mean anything that they steal uh points from they think that they should get the points on hotel rooms that they book from me or something like that even as little as that I would get rid of someone. So there's a culture of trust and intolerance for stealing and for disrespect, but there is a strong culture of happiness smiles and that somebody doesn't have to worry about their back. I think it's important to hire and be around the people that you want to work with and not to put them in positions that they can't handle and then delegate and trust. So you put and you trust the management. So once they
are trained and that's in working and communicating with you, you need to trust that management or get rid of them. Don't have in the back of your mind weak. Just get rid of them if they're weak.
So how do you how do you hire for that? Because that's a challenge, right? We have a we have a hard time. They're getting, you know, right now we're in layoff season. People are hundreds of thousands of jobs are being lost at the moment.
How do you weed through that and hire the people that you know right from the beginning, okay, this is a good human being? you don't know. Um I do have an HR person that interviews does a criminal record checks does all that for me. So people are screened but in the end when it's senior management I do meet the people and you have to have a a gut feel for the person and the questions that they ask you and you ask them it's a gut feel. I have management that works for me now that are in senior management that I can see where they're really good people, really talented, but I don't put them into doing their full job scope. I say hire someone to do this part of your job and even if they're better than you, they will not surpass you. So, I'm very faithful to my management so that they hire people better than them and they don't feel like they in jeopardy. And the market in the US is interesting because it is so the work
ethic to me is not there. I think that in general and I think that some people make more money not working than they do working.
Yes. And that the the talent in certain kind of trades is missing. So that's difficult. And I don't want to get into anything political, but if I look at anything about me living in the UK when they had Brexit, a lot of the talent and we're renovating a castle in England, a lot of the talent has left with Brexit. Many of the people bullish, many of the people, the carpenters, many of the trades were and with Brexit, all of that ended. I see that happening in the US, probably globally, that there aren't engineers, there aren't electricians, there aren't plumbers, there's not the trades that we used to get. There are people that seem making others, not themselves, making more money on just social media.
Yes. But there needs to be a balance. And where is happiness in your work life balance? You need to have work where you feel fulfilled. not just where you're making money too.
Yeah, I think there is a big change and and regrettably co changed the ball game across the board. People realize that you didn't need to physically touch your employees anymore. They don't need to physically be in your office. There is the ability for certain tasks you could actually outsource a wall of it. But there's other tasks you're like, "Nope, I I still need to we need to sit in and have meetings and and execute together." But being able to say that your entire workforce can now be moved remote one way or the other has changed the ball game as far as the work ethic and again I stay away from politics as much as I possibly can. Uh I agree with you wholeheartedly. There's there's a sense of entitlement for source places and you'll find that there's people outside of that place that work harder and want it more and are more hungry and they go from there and you just you have to honor that. When you're talking about
fulfillment and balance with your work, there's a lot of people who never find that and they're stuck like how do I find that purpose? It's like you know they look at you and they're like okay this is an individual who on every financial look is very successful and they look at their personal your personal life like okay wow also very successful how has she done this is she just this unicorn that showed up or how does this individual have that is there selfwork that you've done is there meditation that you've done how do you find that fulfillment and financial and personal success
I don't know that I overtly meditate Um, but I do have this sort of like inner peace like a very strong inner peace. Like what you see is always what you get. There isn't another ant.
It's always this inner peace. And I live from the core of values. And I think that's important to have your own values and have a selfch check. If I hurt somebody, I would be devastated. If I said something disrespectful, I would be devastated. So I just live like that. And that's important. And starting out in in business many many many years ago when you say Deseta Unicorn, I didn't want for anything more. I envisioned that I could build a a big company. I wanted to have something that was widgets and I didn't say I couldn't do it, but I actually had no money. And so it wasn't um that this just happened overnight. I started the company. I always had an air of success like I could do it but you know when somebody is looking at your financial statements you haven't met there yet but I would show people that I was capable of doing it and I did my research before I would approach the banks to invest with me and
because in money lending you need banks behind you and I had this air of doing it but I didn't have any portfolio or any business I had to really set up a business plan show that I could fulfill it and had 30 doors are slammed in my face saying no, you know, maybe next year, maybe when you've reached this point before one of them bit. So, you don't give up on it. And it did not happen overnight. But as I started to build the business, I thought, "Oh my goodness, what if it falls apart? I've got to put food on the table." And I was working another job while I was building my business. So, it it was tiring renting out a room in my my home so I could work a night shift and then somebody would be home with the kids after I put them to bed. Remember at that time I was a single mom. So this didn't happen overnight. And then as I was building my business I started to think what happens if all that falls
apart and what happens if I don't become super successful. So in 25 years I've got to still support myself not to depend on another guy or another husband that's going to leave me a you know without anything. So I started to real estate and rent out the real estate and have the income for the mortgages to cover the mortgages. So I would lease out just say my income was $1,000 a month or 10,000 or 20 or 50 depending on the property. My income would need to cover the mortgage and I would have a mortgage as high not lower than the income coming in so that my tenants paid it off and built an annuity. So now I have I many more than 14 properties income earning ones worldwide and that to me would be an annuity but it turned out to be a business as well. So, and a lot of work. So, there things don't just evolve. But when you want for nothing, like money wasn't important to me.
Making money, what? But showing it off. Didn't drive the Ferrari. I dressed in secondhand clothes. I still buy secondhand clothes. I still look in shops. Still do that. I will buy a t-shirt and then cut it up to make it look like it's a fashion statement. And I mean, unfortunately or fortunately, all this ripped clothing is in right now. So, it's um I' I'd look at it as look successful, put yourself be put yourself together, don't talk gibberish when you're trying to do business. You you wouldn't go and audition for something and then talk about fixing your car. So focus on the moment and focus on that sales point where you're trying to sell yourself and that everything that you put online in life.
And so Charles, I would not do any any kind of vodcast or podcast or YouTube channel if I didn't trust the person that I'm doing it with. And that's a compliment to you because I live forever on the internet. And so start acting kooky on your Instagram, on your Facebook, on anything. That is really just that's one of your that's your resume.
And so what you do in life because at some point you're going to want to do something else. And if you've acted goofy
or threatened, then it'll come back to bite you. So you don't want to be doing things in life that you have to fix later,
right? And clean up. I would say to your viewers, clean up your act if you really really want to be something and be that brand at all times. You can't be part-time somebody who just, you know, sleeps with a bottle of beer in their hand. I don't I don't think I've ever slept with a bottle of beer. Maybe wine.
Depends on the wine. Depends on the wine. That on a on a consistent I like the the the cheap California
Chardonnese. You can't. Yeah, this is interesting because I live mostly abroad. I'm in the US sometimes, which me landing the US, I think I can get California Chardonnay. You cannot get it in Canada. You cannot get it in now with all the tariff threats.
You You can't get Chardonnay California Chardonnay in Canada. I can't get it in the UK unless it's not popular. it it's just and I love love their Chardonnese. Anyway, back on topic.
I'll see I'll see what I can do about that. Uh before we hang up, I I'll see what I can do about that to get that fixed for you. Um
one of the things you talked about and this is specifically hard for females when they're walking into it and they're finding this balance and they're showing up authentically and I agree with you 100%. Your online presence is your brand. And thank God I'm old enough that the goofy things I did when I was a teenager, there were there was no YouTube and internet all. Thank gosh because that would have been embarrassing. I I was on a swim team, so I was in a speedo. Thank goodness there's no pictures of that anywhere because no one wants to see that. Nobody wants to see that. But as we go forward, we're doing this. And when we're talking to the female audience specifically because I want to help them out as much as I possibly can.
What are the tactical things outside of clean up your brand? Like I get it. You may or may not look good in a bikini. You may or may not don't post that stuff. Your online stuff is your brand. Clean that up immediately. You know, I tell people all the time, um, keep it private until it's permanent. And then once it permanent, keep it even more private. No one needs to know your business. Just just there's a reason I don't follow anyone on Instagram. Uh, I s I follow one person. It's a city in Switzerland. That's the only thing I follow. I do not I do not follow because it's just it's there's been some bad stuff that's back then. But as you're going through and you have this tackle redesign of your online presence, what are the things that female business owners can sit down and say, "Okay, this is the world you're going into. You know that this is going to happen no matter what. This is what you're running into.
Here's how you prepare for that." So, I think I think for female business owners is to own who they are. I I mean, don't be um ashamed or concerned about who you are. You don't have to fit into some profile. gone are the black suits and the white shirts and having to dress like men. Be who you are and and that person should be a confident person of the person you are. So own it I would say is the first thing I would say to a female entrepreneur and also to work that much harder because when you walk in that room you have less likely than if it's a man walking into the room. So when you walk in that room, own that room. And owning that room means that know the business to hand. Do all of your research. Be smarter than more knowledgeable than anybody else in the room. Because I can guarantee female or male.
Do as much research as you is if you overtly and carefully research what the topic is. Find solutions for what any question could be asked and even have it ready there in paper in writing. A lot of calls are on Zoom but be very knowledgeable in your subjects as well. So the third one I would say and the biggest one is think really really big because there is no reason that you cannot be everything. So you always look at the business to hand. Make sure that it is um there's widgets that it is there's distribution and that there's uh you can grow that business. So, it's flexible to grow into a large business.
If you're thinking about the business and the entrepreneurship is around, and I used this example before, I'm going to make pies in my kitchen. It's not going to sell to your friends. If you start thinking, my friends bought it, there's someone at the school, a parent at the school, that is not going to work. You have to think all the people you don't know that is going to buy into your idea and think even bigger. And then right now, you've got AI. If you're not thinking of incorporating some type of AI in your business or doing a business that's affiliated with AI, you're missing the boat because that is really big right now. So, um, so I signed up to take a course, a diploma course at Harvard in AI. And so I'm going, I don't know enough about AI. Like, I get it.
It's it's a buzz word. And I get built on algorithms and regression models and I get it that it's built on smart learning, but I need to know more. So get educated if you don't know it. Don't say I don't know. Get yourself educated. And then now you're probably listening and going this is exhausting. This is exhausting. It's too much work. It is a lot of work. But there's no reason you can't balance that work and that life if you really really want to be successful. No one became successful as an entrepreneur without putting the work in. You've got to roll your sleeves up.
You've got to be smarter than the new competition that's going to come in and try and grab your ideas, grab what you're doing, and you've got to stay one step on top of them and be adaptable to change. And females are more adaptable to change than men. So be adaptable to change. And don't be ashamed that you're a female, but don't fall into the female, oh, I'm so exhausted. I got up and I, you know, I had to get my hair done and do all this. I don't mention that
in I mention the things to do with the business and I don't get cocky. Nobody wants a cocky person in business. So, you have to listen and and as a female, we do listen and we communicate well. So listen and communicate well what you're naturally capable and able to do and don't get defensive because it's well I don't think he listened and all that. Don't over analyze. Be prepared because you don't want analyze your words. So yeah, I'm talking about the females I talked to that are very successful but then they find they find um blocks in trying to get to the next level. And and if they talk to me about it, obviously they want advice.
And they say things like, "Well, I get people saying I'm not approachable." And said, "Well, maybe you're not approachable." And so, you need to be approachable, but for the right reasons,
right? And you need to do the work. And I think one of the things you said there was like not thinking big enough. And I I think you and I are both in the same Harvard course right now. But this isn't, you know, you go in and you do it. And we're constantly working on it. And I used to tell to people all the time, they're like, "Why do you spend the extra money for organic food? It's it's so much more expensive." And I say, "Well, it's cheaper than chemo."
So when people talk about when I talk about, I I don't want to do the work. This is so much work and this is going to be so much stress to to invest and research and take the Harvard courses and why are you doing that? I'm like, because the opposite is worse. and understanding that ballgame of yeah I could have taken courses at no offense FAU which is where I got my undergraduate from or I could sit down I could dig in I could do the stuff from Harvard because it's a different ball game and I get to do it online and it's just I want to get the best of the best because this is where we're going. I would love it if we were going to a world that said hey you know what we're only giving money and health and wealth to people who are on this podcast. Sure that would be but that's not going to happen. I'm going to run into a world where things are changing and either I adapt or I die. One of the things that
really stands out regrettably, we don't teach women that they're enough. And we we're constantly telling them, "You need more makeup. Your hair needs to look this way. You need to be dressed a certain way or doing all of this." Your perspective is the complete opposite. It's like, "Okay, you more than enough, but I need you to think bigger." That is a gear shift that most well most men and women but specifically women don't have because by default it's harder because most men think we're one push-up away from looking from the Men's Health magazine. It's just that we were coded with that cuz
we're men and but as we go into this ball game, how do you teach and how do you empower women to think bigger of not only about what they're going to do but about themselves? Well, I think there's one thing that when you go back into the way women think, if if you show up and you're wearing a nice dress and someone will say, "Oh, that's a nice dress." And in their mind, they're going, "How come I don't have a dress as nice as that?" And then women compare themselves to each other. And I think you have to get out of that mode of comparing yourselves cuz that's something that you naturally do.
But women also don't think of themselves as being big thinkers. And I think often it's a threat when a woman is a big thinker. I mean I I was a threat I believe to my husband, my current husband many years, but he didn't I was so entrepreneurial and so aggressive. So I didn't talk about it. And sometimes you just have to play the game. So, our relationship is better because I don't talk about business and I'm doing everything else, talking about the kids and things like that, but not about business. And so, you to realize that a big thinking woman is going to be a threat to men. So, you have to be aware of that. But think really, really big. There's no reason you cannot run the show, be the top of your game, and get the emotion out of it cuz men are very, very good at getting the emotion out of it. So if you can be a woman, be a compassionate person and be a smart thinker and a good researcher
and not emotional about it, then you're stronger. And never ever think that you're really smart and what you can be intelligent, but don't think you know more than other people cuz you never will know what's going on in everyone's head. And you want to be you never want to be the smartest person in the room. You want to be in a room full of people that are not yes people. You want to be in a room full of people that you want to work with. Another thing in business I always do, always do and still do, and I do it now, used to do it on business cards, I do it now in my contact list.
So if I'm talking to someone and they say something interesting about themselves personally, I make a note in the notes under that person's. So Charles, I would make a note if you mentioned you were a speedo and you used to be a I guess a competitive swimmer.
Oh that oh I will make a note because if you and I didn't talk for a year and a half later
and you called me up and said hey Ann and I'd say yeah how you doing and did you ever post about that speedo again? You want to be able to know people, but this is a very fastmoving world. And the more that you grow, the faster it moves and the more people you meet. Another thing that I do, and I try to tell this to my kids, is join organizations. So, I enjoyed the Ontario Economic Summit for years. I was a delegate and the um G20 Y on the banking and finance committee. I met people from around the world. I'd attend this in different Paris or different places that we would have our meetings and I would meet people from around the world and they became part of my rolodex. So and uh this can be done a lot easier now also with podcasts and vodcasts and YouTube channels. You can do that, but join committees and organizations in a large scale and you will meet more people that become part of your contact list. And that is really
important because you want to open yourself up beyond your small or your small is relative um people you've met in the current business that you're in now or in school or in the past. So I opened my world up to a very very big for me rolodex of contact people. And so even now in television I go to the television conferences and I know that I'm not noticeable and I know that I'm not that I'm really nothing amongst all the people that are there that are all searching to sell or buy something. And so I make sure that I make myself noticeable. And so for example, when I went to MIPCOM, which is the um reality TV show conference in Khan,
uh and my TV show is called Queen of the Castle. I brought a whole bag full of tiaras and we handed out tiaras to people
and I literally brought drag queens with me because I was the queen and dressed as the queen
and we were noticed and I had to fight that with the the um producers of the show when they asked me to go to MIPCOM and meet people. I said realize no one will know who I am. I mean, you're you're amongst all of these. You've got Warner Brothers, you've got Disney, you've got I don't know what they're called now in this day and age, but you've got all the TV channels that are there and everybody's there. Make yourself noticeable in a good way.
And so, I think every moment is your elevator pitch. Take those elevator pitches and have that little sound bite available. And something I learned in PR when I would do the news or I would do something, I would practice. I would practice the worst questions somebody could ask
and I that sound bite that I wanted to say written down on a sheet of paper in front of me and if somebody asked me something, we used to do anti-aging shows. So I had where we did anti-aging shows and I was money lending into the cosmetic medical market and veterinary and dental etc. And I know that I and I was money lending into home improvement as well. But because we did money lending into cosmetic enhancement, always one of the first things that media would ask me is what have you had done and irrelevant to money lending
and conventions that we would do. But I would have written down on a sheet of paper. Well, if I was thinking to have something done, I would certainly go to our conference on anti-aging and it wouldn't matter what they said, but have that sound bite that you can slip in and divert from the question. And I hate to say it, but a lot of politicians just put the sound bite in and it has nothing to do with the learn from that cuz it's not bad idea,
right? But do it. But do it. We do it all the time. Don't answer the question that was asked. Answer the question you want to answer. So they could say, "Hey, what is your favorite food?" It's like it's really interesting question. My favorite color is so you're actually answering the question you want to answer, not what was asked. And I think the other thing is when people show up to networking events, they get very scared because like well I'm not the queen of the castle. I'm not oo la I haven't done regrettably the research, which I agree with you wholeheartedly do the research. I remember before social media really blew up, people went on Facebook and they posted everything, their wedding anniversaries, what what their kids, their hobbies, and I would research all of that. So when I got to the meeting, I had more of those like things to connect with. But what I've done at these events is, and I would
love to hear more of your ideas of how you connect because obviously you connect on a huge level, is I will walk up and say, "Hi, what is your biggest problem right now?" So like I I need a plumber. Like awesome. I'll be right back. And I would go around the rest of the party and I would find a plumber. I'm like, "Hi, you're a plumber." I'm like, "You need to come with me." And then I would take plumber to the person needed a plumber. I'm like, "Hi, here you guys connect. You needed a plumber. Have a nice day." when the plumber's really happy because new client and the person's really happy because I found a plumber and that inherited and that I get all that trust and I get all that connection and I will just spend the whole time. So for those of you who are listening, one of the proven tactics that work really well is be in service to others. Say listen, I I might not feel that I'm good enough at this
moment. Great. You can always connect people. There are times where I feel I'm good and not good enough. There's times where I feel like I'm amazing. When when in doubt, connect people. What are what are the ways that you have connected? What are the ways that you know as a female as you're coming into it where they will marginalize you where they will think bad about you? Because anytime I've been on a carpet, no one's ever asked me what I'm wearing ever. And I've had PR sit down and say, "Okay, this is what you're wearing." I'm like, "I don't know what any of those words that came out of your mouth are." I go, I I don't know cuz I don't You walk in, you have your underwear on, and they dress you with everything else. I' I've had to do that. They'll give you a list.
I've never been asked who I'm wearing because my default response will be Target. I I don't know. I just I don't pay attention. It's either Banana Republic or Target. That's just I don't know. But when I'm on stage or I'm being dressed up, it's Armani and all these other things.
I've never been asked. That's a very different world than you live in. So, how do you what are some practical things when you do do research and you are walking into these things and you are setting up that you can give to and again to everybody. It doesn't matter if it's internal plumbing or external plumbing, but specifically for women to be prepared in that environment. So I make sure that I do make those notes that night or that moment. I will take the moment to make a note about a conversation that I have with somebody.
So I don't get into personal life. Never get into my personal life. I get into what that conversation that somebody is having with me. So just say it's at a party or at a dinner or an event. And I do throw the events in the parties and I'll get into that in a second. But when I meet somebody, I will make that note and I will make sure I get their what's up connect on the up and I will follow up and it's like hey it was nice to meet you. I will make that note and I will follow up with them to do with the conversation and so I do not follow up with them and ask for something. I follow up with them. I don't ask like hey you know this is what I do want to invest with me we I'm trying to make a connection for someone to fill a void
or it might plumber is hey it was good to meet you um I hope the plumber works out let me know if you don't find one and I can see I you know I live in the area and I can see if I can get somebody else that could help you follow up with a relevant conversation but do not ever ask for something and never reach out to somebody with an ask and if you have an agenda tell them your agenda So, agenda is I'd like to ask you if you're interested in investing in this firm, but don't follow up and say, "Hey, great to meet you. I really liked your Armani suit and you know, let's connect sometime." Be very, very honest because no one has time to No, no one's that silly or stupid anymore. I don't like using those. They can read between the lines. So be very authentic and be very for you're doing and then follow up and make sure that when you're at a party and you're there to network that you actually do network
and so you actually are promoting yourself as a business person whatever that is that you are at that moment and trying to promote yourself as and then make sure that you're making that connection and the right connections and something that I do now when you talk about networking and is we do and I work with throwing parties where I invite like-minded people in and anyone can do this themselves and one of the things that you can do is invite like-minded people in the same ilk. So in mine it would be CEOs of companies and invite those people to a dinner. They don't pay, but the idea is that they get to network. They get an over-the-top experience, and they their whole guest list, emails, and contacts are shared with everyone. And so, they come there knowing they're going to meet like-minded people. And I don't invite people that don't fit into that group.
So, it's really, really an interesting way to network and meet a large group of people that you can bring together. And if you don't know a lot of people, make it a dinner and then say, "Let's talk about AI and the impact on our businesses and invite like-minded people for that dinner that can network with each other." So, be the networking instigator as well. So, networking enough, create it. Get creative on how you can meet more people in your circle. So, join committees, organizations, and get creative on networking. And if you don't have that group, create the group.
And do not invite your close girlfriends that have nothing to do with it. And so and do not invite your husband and do not let your kids sit at the table. You are working group that shows that you're focused on the moment.
So um I love that one of the things that happens at networking events at groups that I would love for you guys you to speak to is I I have a client and recently she lives in DC. be connected with an individual who was clearly not wanting to talk business with her. It's the cleanest way I can say that without getting in trouble. He was interested in her for far beyond her brain. This was an individual of immense power and trying to take prey on my client. And we walked through a very specific thing of how to how to hold space for that, but also how to exit out of it in a polite way.
My hallucination is you run into that quite a bit. How do you handle that where the other side of the table is regrettably being inappropriate and crossing the lines of getting across on the personal side and being maybe a tad bit too aggressive? How do you handle that without blowing up your network, without creating a reputation where I'm not this, but I'm also not that? How do you deal with that type of environment? So I'm in in no way am I making any kind of assumption about the person you just spoke to spoke of but I am really an approachable person in that way and I if I say hi to a man um in a certain environment that they think I want to sleep with them and if it's and I said this to my daughters is when they were leaving to go off to school um if a man asked you for coffee, he wants to sleep with you. If a man says that you look nice, he wants to sleep with you. If a man wants to look
at your computer, he wants to sleep with you. Do not ever think that you're you look so interesting that they have anything else on their mind. And so anyway, unfortunately, that's it. But in business, when I was building business, I didn't have a lot of confrontation. But the times that I did, I there was one time when there was a banker and we had left a dinner and I was walking to my hotel and he was walking to his car. We walked together and then I said, "Okay, goodbye." And he leaned over to kiss me and I stepped back. Well, you know, just mortified cuz that wasn't the intention. But I took it upon myself to realize I went away from my my own advice that actually somebody doesn't want to just walk in the same direction as me. And so, but then because he was so senior, I addressed it and said, "I know you didn't intend that. No, no harm done.
Nobody will ever know." And just addressed it that way and then kept it professional. And so I got it the book but not to address that he was under any kind of threat. I also traveled for conferences like these are securitization conference, banking and finance conferences, anything. I don't go unfortunately to the brandy and cigars. It's just a girl in a bar. It doesn't work. I don't need to do that. And I have been where I'm traveling on my own and some guy's knocked on my door at my hotel and it's like like guess he saw me go in there and or in the elevator when you're going up the elevator and somebody from the conference decides to hit on you and because it's the last resort like you hit on a 100. It's always a numbers game. Don't think that you're that special. It's a numbers game when somebody is going to hit on you. So you need to address it. You need to address it head on. You first of all, you need
to not be approachable. So, eye contact, that stuff doesn't work. Any kind of joking or insinuation, you're going to regret it later. And but when something does happen, address it and be very professional. And don't say anything to do with anything that means that you're leaving that door slightly open. And the answer of um well, I'm married, it doesn't matter anymore. Don't no one cares if you're married or not. It's probably easier.
Just like keep it professional. Make sure they know that you are profession serious of what you're doing because I can guarantee if you open that door, they're going to think that you're opening that door for other people anyway. So
no one's going to think they're the only one. You're just part of the game. And your reputation will get out there. And if you have made an error, don't beat yourself up. Just don't do it going forward. just don't become what your past was because we all have made mistakes. All of us have and let my mistakes weigh on me. I'm just not going to continue to make them.
There was a there was a movie called Dumb and Dumber within Terry and there's a scene where the lady's like he's like so what are my chances? She's like not in a million years. She's like so you're telling me there's a chance and it's like oh my god. And it just really encapsulates the the male mind. He's like, "Wait, so maybe it's like if you were the last guy on Earth." No. Okay. So, there's a chance. That's not what I was saying. And also, yeah. So, having that kind of No, that's not how it works. Now, when we go into this,
I can say, if I can add this, I can say being in business and I deal with some people that are very high level in business,
they really safe because they know I'm not out to hit on them. I'm not trying to sleep to get ahead. And that's almost a joke, but they I'm not trying to do anything in in a sexual way with them and that I am focused and that makes me a safe person.
Yes. And the easy approach because it's not part of the equation. It's not evened part of the equation. It's not it's not we're never going to go there, but I don't have to say I am approachable because that's not part of it. And aside from that, there's a whole world of people out there. If I wanted to do that, it shouldn't be with business people I do business with.
Absolutely. So, when we start doing business and we start scaling, you've scaled empires and you've scaled, you know, everything from finances to everything else and even your own home. There's everyone talks about processes, they talk about systems and regrettably systems right now is a very much a buzzword. What are some of the tactical systems that you've implemented in your businesses as Zcale? Because you can only do so much, right? We we've learned this from the SEAL community outside of a six to eight man team. Life gets real challenging. So, how do you put in the systems and how do you monitor scaling on that level?
It's it's really hard. Um, it is really hard. You're right. So what I'm doing, if I can use the example with a castle and we're um building a brand with the castle. So I've only had the castle I think 2 and 1/2 years, not a long time and then renovating that. I look at it as okay, what's your ultimate look at your ultimate distribution and then I I go backward from there and I start at the very beginning. So ultimately I want to distribute worldwide to tourists and people that come to England and want to visit a castle and a bride and groom that wants to get married at a castle.
There's where my market is. How do I get to them? Well, social media and uh landing pages like your website and also I look at doing the television. You can do your own YouTube channel too, but I do a TV show around the cast. So, there's my distribution. So, then you go back and you want to scale the business. That's how I'm going to scale it up. Then you have to go back to the beginning. How do I start the business? And so that part is the hard part is how do you get the management in place and then step away from it. So you've got to invest a lot of time in any business you have before you grow it. But you have to know your website platform to start with even before you've started the business.
So you've got to look at your distribution is social media website media is your distribute your distribution channel and go back and start a business. And I do that with my real estate. I do that with my um with my finance business when I had it and my insurance company all those kind of things I have to look at how do I distribute and the channel might not be public it might be it's B2B as well. So when you were talking about distribution there seem to be a little bit for me like I have a goal and then I back into distribution like I know exactly where I'm going to want this to go. It's kind of like firing an arrow. I don't fire an arrow and then decide I wonder where I want the arrow to go. No, I'm very clear where I want the arrow to go like it's going there. Now, how I get it there
that changes the ball game. Is there a difference in your mind between goal and distribution? And then if there is, what are the distribution factors that you have found that have the best ROI?
So, if if I were to make it more clarity that the the goal would be for example in the castle that I want to meet tourists to come to the castle and brides to come to the castle. That's my distribution not my distribution channel, but that's who I'm that's my audience.
My target. Yeah. Yeah. my target audience, but my goal would be for them to come to the castle, spend money, have a great experience. So to spend money, they need a great experience. For them to come back again, it needs to be a great experience. And how do I let people know this is a great experience? So that's my distribution channel. In the insurance company, my distribution channel is B2B. So it would be to businesses that are selling small ticket loans. We do creditors and life and disability insurance. So offer that to your clients and this is the experience you're going to get. And so that's not a public one. That's not social media. That's I have to understand my audience is another business and they want an easy easy platform click on and then they want good reporting. So you have to think of everything and it's not easy. So building your platforms, building your accounting systems, having them work
with, in our case, the castle has a hotel, so it has to work with the booking.com and those platforms. And you know, all of that is not easy. But it's not be what you're capable of. It's just a lot of work,
right? And then understanding that, you know, there's that when I'm getting on a plane, I dress a certain way. When I'm swimming, we're not going to talk about speedos anymore, but when I'm swimming, I swim a different way. There's different distributions in different times at different places. But when it comes to the scaling because you're doing a lot and primarily your your main goal is like I'm a mom first. At the end of the day, I'm a mom. That's my first priority. That's who I am. I happen to do all this other stuff which means you have to build a squad. You have to build a team of people that you trust.
How do you empower, track them down, bonus them up in a very competitive marketplace? Because regrettably, there's a lot of people who are looking for work. the people who have the jobs and the ones that are elite are very they they will find more. There's a very small amount of elite talented individuals out there. How do you build a team of those, empower them, and then scale with them? Because there's a lot of there's a lot of psychology behind it, but I'm curious how you do it and scale to these next levels. So the the way I do it when there's an actual business that I'm running is there's uh if they're with the company for one year then we bonus on the past 6 months of um the success of the organization.
So if they're with the company they have to be with the company one year and then they get a bonus based on the success of the organization. So the revenue so you might not have positive cash flow but you would have a revenue coming in. So they're bonused on that. So they they know that they're bonused on the past 6 months, but if they leave the company, they wouldn't get the bonus. So they have to be the company 6 months. So I make sure that they that they want to be there, but we also offer after they've been there a year, we pay for their education relative to what their job is or what they job they'd like to do. And we will pay for that education. They do not have to pay us back as long as they're working with the company. And then dependent on what we're paying for like an MBA or is it a chef's course or whatever it is they're doing accounting that we've done many many um offerings
and fulfilled for education and as long as they stay with the company relative to the cost and the time it took to do the education one year out or whatever. And we say we want you to leave the company with in better shape than you came to the company in. So that means you've learned from us because you want to be stimulated. Most people do. You want to be hiring people that want to be stimulated, but you want to help people grow, too. And you help people grow, you will grow. So invest back in your employees. They are the biggest asset you have are the people you employ, but invest back in them. And I do not, and it's I don't think it's a bad thing, but I do not offer shares and companies and things like that to employees. I don't make it that complex, but I do offer bonuses based on performance of the company.
Right. So, I I love that you're investing in people that you want to invest in you. Again, it goes back to the be in service, give to others first and you will get more tenfold because this is just it's a a concept that most people aren't doing. They're talking about, oh, I want to have a gym inside the the the um organization or like invest in the people. Give them what they actually what they actually want. So, when we talk about real estate, switching the gears completely, you've invested in real estate and you've done that. The market's changing. The world's changing right now. Um, again, without getting political, it is getting very interesting. When we do this, where do you see real estate going? Where do you see things? Because you sit at a higher perch than a lot of people through a lot of hard work and effort on your own, a lot of self-sacrifice. You've made it.
You have a different perspective than most people do. Where do you see things going with real estate? Where do things going for female entrepreneurs in the next 5 10 years?
So for real estate in the next 5 or 10 years, and we could talk about it worldwide, but it's the housing market, I wouldn't be investing in housing right now. I wouldn't be looking at, hey, I want to have this perfect place to live if that's what your investment is. Depends of what your agenda is. But it's not the time. I think market is going to go down even more. But if you are so inclined to want to buy, invest in something that you can rent out. So start investing the rental market rather than lifestyle market for yourself and then weigh out your what you're paying and for what you live in and even if you have to get a place that you can rent out part of it. So it supplements your cost of living depending on where you're at. So this is not buying or anything.
And don't look for your dream house in this current market. I would wait if you don't have the free cash to do that. But real estate commercially is also on a decline because people are working out of their home. A lot of real estate's into the market. In particular, you'd look at in the last years, all the big department stores are shutting down because everything is online. Now, where would be smart to look at is in warehousing close to airports. And so, I'm looking at, okay, if I'm going to buy real estate, where can I put warehousing? How can I help in the distribution market for where the channels are going and how people are actually shopping? So, look for that.
But if you start to think like that, what you're going to do is get a real estate agent, commercial real estate agent that's going to be jumping all over you if if you they think you're going to buy something from someone else. I don't sign on a realtor. For me personally, I assign different realtors to look for what I'm doing.
They don't want to bother. So, I have to get another realtor to call them and say, "Yes, she is real and she will buy." So, it's also you don't think that you just because you're looking to buy that the realtors are going to listen to you. But if they know you actually are, then you'll know this world, Charles, very well, then I can buy commercial real estate without signing on the broker. And I can buy commercial real estate and get a good deal. And I also look for bankruptcy deals. But I don't know that the um commercial commercial office building is a good place right now. I think converting
what was an office to residential would be especially if you're looking into lower income residential and you might want to look at where subsidized by the city or place that you're in. So that might be something that is better. But get to know the real estate game and do your nap back of the napkin calculation if you're just entering into the market on that. I mean back of the napkin is smart thing to do. When I first went into real estate and I had some cash, I called up two big time real estate guys and I asked for an hour of their time.
Mhm. I brought another female with me so they didn't think I was hitting on them. met them at their offices and said, "Just tell me how you play this game. How does a real estate game work? And I want to go in commercial real estate. I want to start buying commercial buildings. How does the game work?" And they gave me an hour of their time each of them. Completely different perspectives. So, it's actually good that I didn't go to one cuz I would have taken their perspective. Then don't get confused when you get different perspectives because everyone has a different way of playing the game and there's not a right. But listen to a few people and ask the professionals, not your friends. How do I invest in that?
And then real estate and the current market, you want to understand as well. And the political market to if you're investing in rental properties and Airbnbs, that can change because you might have the hotel industry step in in the jurisdiction that you're in and say, "We no longer want Airbnbs." So be prepared for the changes. Right. I I think understanding that it's what the market is currently doing. Like commercial real estate is finally figuring out that mixed use is a different ball game for them. There was a property that was done out here that was a commercial property since the 80s and now it's mixed and it's it's the biggest square footage that we have in Kentucky. And it was just someone who had the vision to say, "Okay, we're going to change the ball game. We're going to make this. We're going to make sure that it not only gives value to the community and the city that we're in,
but also value upstream." And I think the commercial players are starting to understand a mixeduse environment when it comes into bankruptcies and all that. And you were talking about how people shop. Like we've got I'm in Kentucky right now. We have a arctic uh freeze or blizzard or whatever it is that's going to come in. And I'm from Florida. So anything below 20° is very confusing to me. Seeing my car with because my car's up here and it's got my Florida license plate and there's three inches of snow sitting on top of the car. My car is very confused right now. It's like what is happening? But even me who has the ability and has the I'm still just going to go to Costco and say click click and have it delivered. So the way people buy has completely changed. So honoring things have changed. I again I grew up when you went to the stores. I know what Sears is and I know what Kmart is and
all that. Those things don't exist anymore. Understanding that the market has changed completely.
Also understanding that that lunch that you did with those two gentlemen probably saved you and made you millions of dollars to to allocate it. So finding someone and for the people who are listening, most of us who who are just even just one tier higher than you are cuz that's what makes you an expert. You know one more thing than the person that's asking you. That's now you're the expert. Um we want to tell it. We want to share this because we're excited because we've learned something and we want to give back. Most people I know will want to be in service and want to help out and and and go from there. So I I love that you did that. I love that you invested in your people as well with their education and say I'm going to invest in you. Where do you see again different vantage point where do you because everything right now is oh cryptocurrency and AI and all this.
Where do you see things going with that? Especially with a political environment that's challenging. That's as good as I can get. That's as clean as I can clean that up with. Where do you see things going um in that world as far as the crypto and the AI as well? because you have done a lot in finance.
Yes. And the crypto to me is really scary because I don't think they have that locked down right now and there is this big environment of and people have made a lot of money investing in crypto.
I I stay away from that easy money. I hope to get that easy money investment. and there was a girl, she was a a photographer and I hired her in Italy to do a photo shoot
and she had just invested in crypto and made a ton of money and I was like wow like tell me how you do it and she said I knew somebody who was investing in crypto and started a crypto business that's how I did it. She said I would stay far away from it. If you don't person that founded the company and it's almost like a lot of the stocks you get in on the early investors you've got and then they don't say that. Of course not because that would be inside information. But if you don't know the game like I don't invest in real estate I mean in in stock the stock market or crypto because I don't know the game
right I don't know about businesses and I was reading about Warren Buffett recently and he would invest in his early stages he got to know the company before he invested in it. Yes. So, if you're going to invest in anything, crypto or the or stocks, know the company that you're do your research. Are they a legitimate company? Are they a startup? What is the market like? You actually have to do that or don't invest. So, I think that's really important. But crypto, I see it shaking everything up. I don't know if it's going to take over for for currency like US or or euros or p British pounds. I don't know that it can or will do that. But I cognizant of it and I'm cognizant of cash. Cash, you don't want to hang on to a lot of cash
cuz cash nothing when it's left in the bank doing nothing. And so I make sure that I try to invest back, but right now it's mostly bonds and things that are safe because I don't know this and I have to say I can't give advice on investment because I'm not an investment person. I'm a careful per.
Well, I think the advice you just gave is is important, right? If you don't understand something, and I learned this from Melvin Simon at the time. He was 64th richest person in the world. I'd never met anyone like that. He said, "If you don't understand it, you're not investing, you're gambling, and that's up to you. you want to gamble, gamble. But if you're investing something and you don't fully understand it, be willing to lose the cash. And if not, it is what it is. So having that perspective change for me from for the person who had been there change like I'm I'm not a crypto guy. Do I think the the blockchain technology can be used inside currencies in the future? Sure.
But I I don't know anything about it. So my goal is to kind of stay away with what I feel is safe and what I think, okay, I've got a little bit of knowledge in this. This makes sense to me. and if not, I'm not going to risk certain certain things.
So, yes, you've you've also so you've done well in business, you've done well in your personal life, you've also broken into the online world as far as, you know, you have a TV show and you've and you've had to deal with the trials and tribulations of fame. If someone wants to go into that world and they want to step in and break through, what are what is the advice that you would give them as far as is this a path you would recommend? what are the things they should avoid when it comes to becoming a personality and online or in on TV.
So I think if you are building a brand I would say build yourself up on social media be that brand and there's nothing wrong with I mean I don't do things to be famous and I'm not all over famous all over the world but in certain markets I am known and especially Canada
but the I mean but doing a TV show you do get recognized going different places in different markets but I say, build your brand. Build your brand up on social media. Be that personality because that brand helps market you. Your personal brand will open doors for you. And the more you're recognized and social media is the best place to do it. The more you're the more that door will open. When you contact somebody, they're looking on your Instagram page. They're looking you on social media. Who is this person that's contacting me? So at the top you have your what your description is. So I have that description on my social media and that brand is who I want them to know. You will not see my kids on my social media. That's not the brand I want people to see me as in business. That's my personal pay out of my personal life. I Yes, I am a mom, but I let my kids have their own identity. I shouldn't say I let them. I want them to
have their own identity. So be that brand. that the person I admire the most is Richard Branson and it's so sad now that's so heartbreaking um losing his wife but
is um but Richard Branson markets himself first and foremost he is a brand who's not ashamed of who he is he owns who he is he's an out there adventurous person that's also a business person he's approachable he's nice he is that let's just have a party and let's have it happen, but let's get to business tomorrow. He's philanthropic. He brings people together. He's engaging and I that that I admire. So look at somebody you admire and I admire him and I think I'm not going to be market my brand. So that brand opens doors. So when I want to for example go to banks for money, if I want to purchase something, they actually know my brand. And so that open don't have to say who is she. They can look me up on social media. They go, "Oh yeah, yeah, yeah, that's who she is."
And then also on my LinkedIn page, it has the businesses I've had. That's my my link in the page would be my resume.
Mhm. My Instagram would be my sort of pictures and you know what I want to be presented as. And my Twitter would be the news that I'm interested in. I look at that for news feeds. I look at Twitter as a different place. Facebook. Do not have a Facebook page that shows your yourself in your bikini if you don't want to do that or your speedo or your kids and doing a barbecue. Have a separate one that is not public with your family.
The one that everybody can see. Your Facebook page should be your the same as your business page. And and then I also have a my own uh website which is a brand I want people to see when they find me. That's very I know it is but you need to be. But I am myself.
I am myself in all of them but very careful that I'm not putting out something that I don't want the world to see because it is a world in a very cruel world unfortunately
and it will come back at you even if you don't want it to and don't succumb to it either. But I think it's important.
I think when you talk about platforms, understanding that again, you don't dress for at at a tuxedo, at a black tie event in can't believe it's saying again, but in a speedo, you don't go to the beach in a suit. There is a time and a place. and understanding that Instagram, Facebook, Twitter, Tik Tok, whatever it is, there are rules in that environment and they show up in a very specific way. And obeying those rules and being able to control your image because regrettably, we live in a society that if I drank some water, one group will say, "Oh my gosh, he took water away from children and he's the most horrible person in the world." And then the other people like, "Oh my god, he touched the water, now it's holy water." I'm like, "Oh my goodness." So, I can't control what's outside of me, but I can control at least what I'm putting out there and the brand I'm trying to represent. So, if people do
look me up, um they're like, "Oh, this is this is what they're trying to say." Maybe that was just someone who's a troll and someone who just needs to get out of their house and get some vitamin D every once in a while. So, just again, I I can't control those people. One of the things you talked about being very intentional with and something that's really important is you know how to find you and how to connect with you and that this is how you show up here. this is how you show up there. Especially for my audience who are females because I get questions all the time and they're, hey, this is great. We love it for this, but we would love a female perspective.
Again, sorry guys, for for the guys out there, yes, by all means, please contact Ann. I've had I've had conversations with she's a lovely, amazing human being. But also, if people want to track you down and they want to connect with you and they want to be empowered and say, "Hey, this is someone who seems to have done it on." And it wasn't an easy road, right? If you if you look up your story and you read your book, it was not an easy road that got you here. You didn't wake up with a silver spoon and then have the perfect relationships and then have you went through trials and tribulations and you decided, okay, I'm still going to double down and invest in me and I'm going to pick myself up and do it. If people wanted to get a hold of you, if people wanted to connect with you and they want to learn more about you and operate in a level of integrity that you show up with, how do they do
that? What's the best way to get a hold of you? I think they would go on my Instagram and message me and Kaplan like an n k a p l an n own it
and message me but but reference your podcast your podcast your YouTube channel reference your name
and just say this and that will get more attention because behind the scenes I have someone else who manages my messages but they will bring it to my so somebody actually wanted to message me on that but ref and just say that they saw that and I will absolutely reach back and so it's it's important that they reference that because I do get a lot of messages
and I get a lot of trolls and yeah it's it's yeah for those who are playing at home I don't read my own messages on social media either I have someone else who does I don't if if you see that I'm online probably sooner to you an It's not I it is someone on my team and they're filtering all of this because just bandwidth and just regrettably trolls and I don't let that energy in. But um thank you for coming on and sharing and being so humble and honest to connect with the audience. There's as soon as you came on because we get pitched all the time for people to come on as guests. As soon as you I'm like absolutely 100% I move everything around. I want to bring Ann on I want to talk to her. Thank you so much for coming on and sharing so much of you with us.
Thank you. That's a wrap on another episode. Where identity beats income and your reputation writes your future. Clean up your brand. Own who you are. Show up like the person you're becoming. Because in a world that never forgets, how you live online is how you get paid offline. And remember, if you don't control your image, someone else
Questions about this episode
Who speaks in "From Single Mom to 2 Billion how Class and Courage Win - Dr. Ann Kaplan Mulholland"?
Dr. Ann Kaplan Mulholland (Guest), Charles (Host).
What is "From Single Mom to 2 Billion how Class and Courage Win - Dr. Ann Kaplan Mulholland" about?
Dr. Ann Kaplan Mulholland shares her inspiring journey from being a single mother to building a $2 billion empire, highlighting how resilience, class, and authenticity are key to overcoming challenges and dismissing societal doubts about success. Her story emphasizes the balance between motherhood and entrepreneurship, showcasing the importance of embracing one's intelligence and capabilities.
What is mentioned in this The Proven Podcast episode?
24 people, works and ideas are mentioned, including Single Mom, Jeffrey 71st – Miller, Charles, Women Entrepreneurs, Commercial Real Estate, Small Ticket Loans, Women in Business. Each one on this page links to its own page with every episode that mentions it.
How long is "From Single Mom to 2 Billion how Class and Courage Win - Dr. Ann Kaplan Mulholland"?
The episode runs 1 h 13 min; the transcript is about 14,266 words in 138 timestamped sections.
More from The Proven Podcast
About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated January 24, 2026.