From Single Mom to Queen of the Castle: Ann Kaplan Mulholland
episodePreviously titled “From Single Mom to Queen of the Castle: Ann Kaplan Mulholland on Building an Empire with Zero Excuses” — renamed by the publisher on Aug 4, 2026
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How did Ann Kaplan Mulholland transition from a single mom to a successful entrepreneur?
She was cast on The Real Housewives, owns a castle in England, and sold a company that did business with over 16,000 doctors, but still says she doesn't feel glamorous. This is Dr. Anne Kaplan Mulholland, a single mom who worked night shifts, built a finance empire from her kitchen table. and now owns 14 luxury properties across the globe. She's about to explain why the most successful entrepreneurs never buy into their own hype and how she used a TV show about her castle, yes, her castle, to build a global brand. If you're grinding away but still feel like you're faking it, you're about to find out why that might be your greatest advantage. This is the way.
You have such a dynamic and interesting background. I'm excited to spend some time together. It's great to be here. It's really fun. It's fun to talk about being an entrepreneur. And it's also, I think, secretly, we like to talk about our own journeys. So we like to talk about ourselves, which is probably one of those little things you know at a dinner table is to get people to talk about themselves. And then they go, at the end, they've talked about themselves the whole dinner. And then they say, oh, you're really interesting. It is amazing the power of being a good listener. and how important it is. Uh, I had a guest on probably about a year ago and he was talking, we were talking about, uh, negotiation, um, negotiation.
Uh, Oh my gosh, his first name is Kwame. I'm going to forget his last name. I saw, sorry, man, I'll go back.
What is the 'Widget Philosophy' and how does it relate to wealth creation?
I'll have it linked up for everybody, but he was, he's a master negotiator and he brought up something. And just to your point, your anecdote there, uh, about being a good listener, how, uh, We reflexively, when someone, like if I ask you, you know, hey, how was your day? And you give me a couple tidbits. I reflexively then want to barf my day onto you, even though you didn't ask, as a way of kind of forming a bridge. And what he was, what his point was, and I found this to be like really interesting, was... that actually diminishes your ability to influence or connect with that person, even though we think that we're like finding common ground, that common ground that we think we're building It's rarely taken as common ground by the other person.
They feel like you just kind of waited your turn to barf your story on them. And his whole point was like when we ask a question, it's way more powerful to ask a follow-up question or really be that active listener and fight that urge to like, well, I've – You know, done a similar thing and or I, you know, I have this story that kind of matches your story where we think we're built. And he's like, that's like the worst thing that you can do when you're trying to build connection with someone. And I found that to be really interesting because I think I do that. I'm probably doing it right now. You actually just did do that, isn't it? Very interesting, but we're not negotiating, so that's okay. Yeah, well, I would love for you to share with the audience your story, or at least as much of your story as you think is relevant, because you have this just wild and dynamic background and all these different things that you've done, and I think it just provides wonderful context for the rest of our conversation.
Well, I think I'll probably put it in a context, because I did write a book, and I'm not here promoting my book, but it's called How to Be Successful in Spite of Him. And then I crossed out him when I was going through it and said, how to be successful in spite of yourself. And the reason I wrote that was I started to get invited and I joined the speakers group organization and giving lectures. And I was always asked to give a lecture to people that were young entrepreneurs and young female entrepreneurs.
What is the Tiara & Hard Hat Strategy and how can it help entrepreneurs?
And the questions always came up at the end. How do I do this? This happened to me in my life. And I've got a boyfriend and he doesn't want me to be in the girls in their 20s. And he doesn't want me to really pursue that way. He wants me to spend more time with him or we might get married.
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Chapters
8 chapters
1
How did Ann Kaplan Mulholland transition from a single mom to a successful entrepreneur?
0:00–1:40
2
What is the 'Widget Philosophy' and how does it relate to wealth creation?
1:40–3:57
3
What is the Tiara & Hard Hat Strategy and how can it help entrepreneurs?
3:57–4:34
4
How can honesty improve your ability to ask for what you want?
4:34–6:57
5
Why isn't your website your business and how can you fix this common mistake?
6:57–8:35
6
What strategies can help build a memorable brand?
8:35–14:23
7
How does humor play a role in Ann's entrepreneurial journey?
14:23–19:02
8
What lessons can be learned from Ann's experiences in the TV industry?
19:02–43:32
Speakers
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Why Pressure Kills Deals and What Elite Performers Do Instead | Guffy Wright
George Bryant on Being Seen, Survival, and the Cost of Hiding
Award-Winning Keynote Speaker: Why Human Connection Beats AI
AI Isn't the Moat in 2026: How Marketers Win with Skills + Context