Ep465: Judy Weber – Get Back to Dreaming Big

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Quick take

BIO: Judy Weber is a women’s business strategist and scaling expert, helping six-figure female CEOs take their business to the next level with strategy, systems, and simplicity.

STORY: Judy always played small and allowed fear to hold her back from being who she truly wanted to be.

LEARNING: Don’t let fear stop you from pursuing your dreams.


“Courage is not the absence of fear; it is taking a step forward even in the midst of your fear.”

Judy Weber


Guest profile

Judy Weber is a women’s business strategist and scaling expert, helping six-figure female CEOs take their business to the next level with strategy, systems, and simplicity. Her global client base is outstanding professionals, experts, coaches, consultants, and creatives.

A former trial lawyer and c-suite executive turned serial entrepreneur, Judy overcame a lot to get where she is today. A small-town girl from humble means, she did what others thought was impossible as she pursued her dreams without apology. Featured on Fox, ABC, NBC, and CBS, women seek Judy out to learn how to think like a CEO and scale to seven figures!

Worst investment ever

Judy’s worst investment was playing small. She lacked faith and didn’t believe in herself. Even though she was super driven and always wanted to be a lawyer, her lack of self-belief saw her study to be a music teacher instead of a lawyer. It took Judy five years after graduating from college to actually start law school because she was thinking small and didn’t believe she could be a lawyer.

Lessons learned

  • Don’t let fear stop you from pursuing your dreams. Take action in spite of the fear.
  • You’re perfectly imperfect, and you’re enough right now.
  • It doesn’t matter your age, go for it and see what you can accomplish.

Andrew’s takeaways

  • The possibility of what you can do is beyond your imagination. If you do the next best thing for yourself each day, you’ll be amazed by what you can accomplish.

Actionable advice

Open up your mind to possibilities, and just take “no” out of the equation. If there’s something that you have always had a burning desire to do or to pursue, don’t let anything stop you.

No. 1 goal for the next 12 months

Judy’s number one goal for the next 12 months is to get her two books written and published.

Parting words


“Pursue the impossible.”

Judy Weber


Read full transcript

Andrew Stotz 00:02
Hello fellow risk takers and welcome to my worst investment ever stories of loss to keep you winning in our community we know that to win in investing you must take risks but to win big you've got to reduce it. Join our community to claim your podcast listener discount on my valuation masterclass Boot Camp, where students learn how to value companies like a pro and advance their career. Go to my worst investment ever.com to join our community for free fellow risk takers. This is your worst podcast hosts Andrew Stotz, from a Stotz Academy, and I'm here with featured guest, Judy Weber. Judy, are you ready to rock?

Judy Weber 00:45
Andrew? I am, I am so excited to be here. Thank you so much.

Andrew Stotz 00:48
Yes, it's my pleasure to have you and you know, you have a lot of energy and I love your energy. And I love what you're doing. And I've been listening to your podcast a bit and trying to understand more about you and what you're doing. And I want to introduce you to the audience. So Judy Webber is a women's business strategist, and scaling expert, helping six figure female CEOs take their business to the next level with strategy systems and simplicity. Her global client base consists of outstanding professionals, experts, coaches, consultants, and creatives. A formal trial lawyer, and C suite executive turn serial entrepreneur, Judy overcame a lot to get to where she is today. A small town girl from humble means she did what others thought was impossible, as she pursued her dreams without apology featured on Fox, ABC, NBC, and CBS. Women seek Judy out to learn how to think like a CEO and scale to seven figures. My goodness, Judy, would you take a minute in Philly for their tidbits about your life?

Judy Weber 02:10
Oh, my goodness. Well, how much time do we have? No, I do want to just mention about some of the things I overcame, you know, this is going to lead into the worst investment ever. But the idea that where I come from people like me, didn't go to law school. People like me didn't even go to college. And people like me, his poor folk. were, you know, six kids in a house with one bathroom. And, you know, just the basics of life. But I didn't know I was poor, until I grew up. So that's just a little bit about a little bit of a story about some of the things I had to overcome.

Andrew Stotz 02:53
Well, that's, uh, you know, that's inspiring. And I know, for all the listeners out there, you know, we're all faced with our challenges. I think one of the lessons I learned in my life at a young age was that the challenges we face are relative. Everybody has a challenge. And I look at some people and I think, My God, how did they not break under that pressure? And then I look at someone else, I say, how did they break under that pressure?

Judy Weber 03:24
Right, I know exactly what you mean. Absolutely.

Andrew Stotz 03:27
And so I think the point that I would just make to the listeners out there is that you are struggling with your own challenges. And you know, what, what I get from what Judy's just told us is that you can overcome. And I think one of the lessons that I learned and I am I want to just tell a quick story. And that is when my sister passed away in 1998. It was very painful for myself and my family. And she had three daughters. And it's part of what spurred me to think about what could I do as an uncle to help them to start investing and you know, really, I felt like I could help in that one area. But I came back to Thailand, and I was very depressed. And I was kind of sitting in my sorrows, despite the fact that I had a good education. I had business in Thailand, the economy had collapsed. We were going to a crisis in 1987. But I was pretty down and I decided to volunteer my time at a shelter called Child Protection foundation here in Thailand. And the husband and wife basically would go out and they would rescue these kids that were being that were in awful situations with their families, physical abuse, sexual abuse, all of this. They would collect the cases of these kids, because the police were involved in many of these things. There was just awful situations. And they would show me like this kid's gone through this or that. But I remember I was playing with this one kid he was part About eight or nine. And they had told me the horrific things that he went through. And that little boy was kind of in the corner. And he was throwing this ball to me. And we were throwing this ball back and forth in this very, very simple act. And he, I can't, I can't tell the story without tearing up, because it's such a powerful message for me. But for me, to watch him just enjoy that moment of playing with me and just throwing that ball and laughing and laughing and smiling. And I thought to myself, this kid has every right to be crying every moment, and he's not look at the positive power that a young kid has look at the positive power that's in us, and encourage that, and that little kid never saw him again. You know, me, I don't never, I could never pick him out. But that little kid touched my line. And so I just wow, think about that.

Judy Weber 05:56
That is so beautiful. And that, that addresses wealth, right? This podcast is about wealth and wealth is so much more than money. Wealth is the support of another human being, you know, great relationships, they add so much to your life, because let's face it, some people have money, wealth, but they're in their own prison in so many ways. So yeah, I love that the more we give a The Bible says, right, giving is better than receiving. And that's just so true. I love that story. Thank you so much for sharing that.

Andrew Stotz 06:33
Yeah. Well, now speaking of stories, now, it's time to share your worst investment ever. And since no one goes into their worst investment thinking it will be. Tell us a bit about the circumstances leading up to then tell us your story.

Judy Weber 06:50
All right, well, ah, the worst investment was playing small. And I have to say, I just turned 55. And now I'm understanding my mom, when she said, when she got older, I speak my mind. Because I don't know how much time I have, I've got to make the impact that I can right now. Right? So for me, the worst investment is playing small, which really comes down to a lack of faith, I don't really believe in myself, I don't really believe that God's gonna provide or those kinds of things, right. So when we play small Andrew, we underestimate our reach. We underestimate our impact, and really our value. So I want to take all the ladies listening, go back to your five year old self. And I can almost guarantee that you had what I call little girl dreams. And it could be I wanted to be a ballerina, or I wanted to be a famous singer or actress, or a teacher or a lawyer, or maybe even the president. A lot of us thought that right? But over the years, those dreams that were once so vivid and crystal clear, become faint. And the vision that was once so vivid becomes cloudy. And the what ifs takeover. Right? What if I fail? What if I mess up? What if I'm not as smart as I think I am? What if I'm not as capable? As some say that I am right? And what if so and so thinks less of me or judges me when I do this or that? Or even worse than the what ifs? Then we say, Oh, I shouldn't? I shouldn't. And it's like the should and shouldn't like, where do we get that from? Or I can't. Because I'm not worthy. You know, when I graduated from college, I was the first one of my family to go to college. I was so blessed. And my graduation from high school president was the opportunity to go to college. And I always wanted to be two things. When I was a little girl. I wanted to be a teacher. And I wanted to be a lawyer. But I went to college to be a teacher, a music teacher actually couldn't get a job when I came out even though I graduated second in the class, but anywho I wanted to be a teacher and a lawyer. And there was a part of me that always felt like I was destined for big things. Like I even said, I'm going to be a millionaire one day, Mommy. And of course she laughed at me. Okay, yes, honey, you know, my parents always said I could do anything, but that seemed just impossible. But I didn't think that people like me, could be a lawyer. Even though I was super smart. And even though I was super driven. So I had five years after graduating from college before I actually started law school because I was thinking small. I can't do that. Why? Just because nobody else did it. Who cares? Right. So when we play small and I'm thinking that as the ladies are listening, what I'd like you to do right now is Think about that little girl dream, and has it come to life? And when you're alone with yourself at night, right, when we're laying there in bed trying to fall asleep, sometimes you might have that thought and think, wow, why didn't I go for it? Why didn't I try that? So what if I fall on my face, right? But when we play small, we don't write that book. We don't jump on that stage. We don't submit that article to Forbes, or, you know, Business Insider, or whatever that publication is we don't reach out even to local TV, because we think why would they choose me, I'm not pretty enough. I'm not young enough. I'm not whatever enough, right. And sometimes when we have this small thinking, we don't even stand up to be heard, we just sit there in silence when we could help. But we just stay quiet out of fear. And I would be remiss if I didn't even mention all that's going on in the world today. With the craziness here in the States, and really throughout the world. There's a part of me that's like, well, what can I do? What can any one person do, but there's power in one. And I do want to land here for just a second Andrew, think about the power of one friend, your very best friend. And everyone listening, think about this one person. And when you were down, it's the one person you know, you can call, or it's the one person that's just always always there for you. Gosh, that power of one person is ginormous, talk about one spouse, if you're blessed to have a good spouse, the power of one child and the impact that that child has made for you. Those of you that are entrepreneurs, you know that one program, that one service that you do think about the people that you impact. And for me, I am a Christian, I'm a I'm a I'm a lover of the Lord Jesus Christ, first and foremost. And secondly, I'm a women's advocate, I mean, the power of one God, I mean, we can't underestimate the power of one, really. And so when we think about playing small, and being fearful of speaking out, when we should win, we can write, and then you think, I'm afraid, fear of what? Fear of failure, a successful life, and business is happily riddled with failure. You know, failure marks the road to success, period. We think about Thomas Edison. That's the standard, right? How many times did he try to invent that light bulb? Thank God, he didn't stop at try 999? Are we be sitting here in the dark? Or with candles, right? So just to wrap this up, really? I mean, we must choose faith. Right? And hold on to those little girl dreams or for the men listening? What did you want to be when you were that little boy, right? And we've got to bring those dreams to fruition. Faith is really a belief in what's possible. But actually, I go beyond that. I pursue the impossible. I've done it all my life. When I first told my mom that I was going to law school, and she knew I was smart, but still, there was this reality, quote, unquote, and what's really likely or possible, and she said, and this is 1991, or 92. I started law school in 92. And mom said, Judy, it's a man's world. Do you really want to do that? I was 25. At the time, she said, You really should be looking for a husband. That's what you should be spending your time doing. Because why do you want to get in debt, you'll be six figures in debt. You'll be working in a man's world, and it's going to be an impossible thing. And to my credit, my mom was a wonderful mom. I mean, she made me who I am. She said, Judy, you are a leader. Keep going, keep going. But yet, when I wanted to really stress myself and be a lawyer, that's what she said to me. But in that very moment, Andrew, I still remember it. My dad was kind of on the other side of my mom, and he waved his finger, like, come here, and we went out into the kitchen, and he goes, You go for duty. Because if you don't, you're always gonna regret it. So I'm behind you. Mom loves you. You know, she knows you can do it. She's just afraid for you. Just go for it. And I'm just so appreciative of my dad pushing me like that pursue the impossible. I've done it all my life.

Andrew Stotz 14:18
So how would you describe, you know, the lessons that you've learned from going through all this?

Judy Weber 14:24
Wow. I mean, I could talk another hour about all the things I've overcome, okay. Eating disorders, anxiety, panic, agoraphobia. To think that I used to drive into from the suburbs into the city of Philadelphia for court and deal with the craziness that happens in court. It's only by God's grace that I was able to, you know, recover from those things, to be able to do what I needed to do. And so, I am a living example of Don't let your fear stop you. You take action in spite of the fear. And you know, it's funny, a lot of times we talk in terms of fearless, I am fearless. I like to say I'm courageous, because courage is not the absence of fear, it is taking a step forward, you know, even in the midst of your fear. So that's a huge overarching lesson that I would love to impart to all of our listeners, and you just do it, and you don't let anything stop you.

Andrew Stotz 15:30
Well, that's an inspiring, you know, story. And I, I've written down a bunch of notes and things, you know, first of all, I love the power of one. And it really reminds, it reminds me and that's really what I was describing about the interaction I had with that kid, it was just that one on one interaction. It wasn't even about, you know, someone that I could really rely on, it was just that power of one. So that's a great thing. You know, another thing I wrote down was, you know, why do we have big dreams when we're young? You know, forget about why we don't pursue big dreams. That's another question. But why do we have big dreams?

Judy Weber 16:07
I love that. I love that I. I'm sorry, Andrew.

Andrew Stotz 16:12
And I'm just thinking like, Why do I want to be an astronaut? I want to be a president, I want to be, you know, why do we have big dreams? I would guess, because we see a limitless potential. You know, we see something that is crushed out of us, you know, over time, and I don't want to talk about how and why it's crushed out of it. I just want to say, wow, it's spectacular, that we have these big dreams.

Judy Weber 16:41
It is isn't it. And I me personally, as a Christian, I believe that God equips us exactly as we need to be. I like to I tell all my clients who are perfectly imperfect. So you know, we don't necessarily, we're not going to be the person today that we are going to be in a year from now. But yet, you're enough right now. So God promised to equip us for what we're called to do. So I firmly believe that as a little girl coming from a poor family, who had next to nothing, be it I had these big dreams, I think it's because God kind of chose and said, you're going to do this. So I've got to put this in your heart, this desire, this dream of more so that you can really see what's possible, even though the world will tell you it's not. So that would be that would be my estimation as to why we have these big dreams.

Andrew Stotz 17:39
So some other things that I wrote down. I wrote down TV repairman, basically, I, I had trouble with alcohol and drugs. In fact, you and I are very close to the same age. I'm 56. And I basically was in three different treatment centers, three different rehabs. The final one was a seven month rehab, that really got me straight. And I remember, you know, a lot was coming together for me at that time. And I was pretty excited about life, I didn't have any money. And my parents basically said, Well, when you get out, you're gonna have to live on your own. And so I kind of just didn't think I'm going to go to university or anything like that. But I, what I had was happiness and sobriety and a relationship with my higher power. But what I wanted to be was a TV repairman. That's what I wanted to be. And I saw a guy that was doing that. And he had a little house and he had this life. And I thought, that's what I want to do. And that's what I left that place doing. Now, here I am in Thailand, with a PhD in finance, having led people in the finance industry in Thailand and been a leading analysts having a business and a factory with living my mother here in a safe environment that I've created through the hard work that I've done and all that, you know, nobody would have put any of that together. It's impossible. So what I just want to take give from that story is to the listeners out there said, you know, you the possibility is be on your imagination. Absolutely, you know, you have to understand it's be on your imagination. If you do the right thing. Each day you do the next best thing for yourself. You'll be amazed before you're finished, it's a lot like on a ship you're going across, all you can see is just the horizon. You can't see what's beyond it. But if you keep going for that horizon and keep going that far right horizon, you're going to end up somewhere. There's a second thing I wrote down, and that is, I wrote down seafood. And I'm not a big seafood eater. I eat some fish. I eat some shrimp. But I don't really eat like clams or stuff like that too much. Just not not big on that. And, you know, my mother moved in with me five years ago here In Thailand, and, um, a couple of like a year ago, somebody he said, You remember when everybody got hepatitis? And I was like, Yeah, barely remember that. That was like when I was like seven years old. And we were living in Connecticut, and we had gone on a holiday. And we had eaten some clams and some crab or whatever. And everybody in the family got sick with hepatitis, except for mom and me. They all were in their rooms, and they were kind of, you know, quarantine, back when they used to quarantine sick people. Yeah, that's another. That's another topic, but we'll leave that one. But the point is, is that mom's like, Yeah, I mean, they almost died. I mean, they were like, really in bad shape, but we didn't get it. And then I just thought, that's why I don't eat shellfish. Ah, it all came together. You know, here I was 56 years old, putting the pieces together. And it made me realize when I asked this question about why, you know why we dream big? And then you have to think, Okay, why do i Why do we get diverted from our goals? Part of it is that these things that happen to us in our past, can live on the rest of our lives. And sometimes we have to go back and deconstruct those things, and obliterate them in the past, to get the present and the future that we want. And, you know, that I think those are the main things that I'm thinking about when I'm thinking about your story. Is there anything you would add to that?

Judy Weber 21:34
Well, one or two things, to your, to your see. That's so amazing. That as you think back that impacted you for the rest of your life, or at least until you've identified that. And so I know with me, I, my first husband, we had been highschool sweethearts, and I was a domestic abuse survivor. I mean, I would never have thought that he would have been horrible to me physically, emotionally, and all that. And so I have not had the best relationships with men in my life. You know, but God gave me three boys. Now they're 2022 and a sharp 25. And I just adore, they helped me to see amazingness in men, that but for them, I might not have really seen. So it's just interesting, because, you know, I'm a feminist. And so for me, all I wanted all my life was one daughter, to pass down, you know, all of this wisdom within their mama, right? But God knew that, you know, you want a daughter, but what you need is three boys, and I'm going to give them to you, and they are going to make wonderful husbands, you know, for women, you know, in the years to come. So that's kind of a neat thought that your story led me to. And one more thing on the idea of dream really big. And what is really possible. Ephesians 320 Is my life verse, which talks about how God can do more, exponentially more, what's the word in measurably more than all we can ask or even imagine? And it's amazing, because He does it through the power of Jesus in each of us. So it's so awesome that by His grace, He allows us to take action in it. I mean, he could just do whatever and say, Okay, this shall be, but instead, he says, You know what, I want you to take part in this. Just like when Jesus turned water into wine, go fill up those urns with water. Thank you, he allows us to be a part of that. But for and you know what, one less thing, Andrew, no matter what your age, you might be listening and you're in your 20s, you might be listening and you're in your 70s It's never too late to say you know what, I'm going for it. It's not too late. If I have air in my lungs, I can do this. So I would encourage you to just go for it. And you'll never even you I think you'll be amazed at what you'll accomplish.

Andrew Stotz 24:06
That's a great lesson for the listeners out there. You know, it doesn't matter what your ages go for. I have a student in my valuation maths class bootcamp. She's 36. She didn't study finance, but she really likes it. She works in marketing. And she asked me, could I get a job in finance? And I said, Absolutely, you know, as long as you do the work that you've got to do, and she said, Yeah, but some people say, you know, you can't I said, Who? Who? Who's some people, but get that throw out some people. And I'm telling you set your plan, set your goals, and you can get there. So based on what you've learned from this story and your own experience, what one action would you recommend our listeners take to avoid suffering the same fate and living that life?

Judy Weber 24:58
You know what, that is so good. I There's a couple of books I'm writing, one of them is called the unlived life, and it's based upon my mother's life, she was raped at 10. And she never really recovered from it, she always lived a victim. But it was amazing, despite all of that, that she poured so much into me to build me up to be this leader. So, you know, what I would ask everybody to do is to really go to God, I believe in Jesus, whatever your higher power is, and ask him ask that power to reveal to you, you know, what is my purpose? What can I really do, and to open up your mind to the possibilities, and just take no out of the equation, if it's something that you have always had a burning desire to do or to pursue? Don't let anything stop you.

Andrew Stotz 25:51
And for the listeners out there, who are really relating to what you're saying, you know, I think you've got some ways that they can follow you get in touch with you, and also an offer, maybe you can talk about that. I'll have the links in all the show notes.

Judy Weber 26:06
Great. Great. Thank you so much for the opportunity. Yes, I am everywhere. LinkedIn, Instagram, Facebook, at Judy Weber, CO. At Judy Weber, CO, Judy web, er, SEO. And for your listeners, anybody who is an entrepreneur, who is has enjoyed some level of success, I start at six figures or just under six figures. And I take you to scale that towards seven figures. So I invite all of your listeners to a very special strategy session where I'll get to know you your business what your goals are. And we'll map out together how to get you from where you are to where you want to go. So I would be honored. And I would love to hear from your listeners for that opportunity for a chat.

Andrew Stotz 26:51
Great, and we'll have that link for the breakthrough strategy session in the show notes. So ladies, don't miss this opportunity. Last question. What's your number one goal for the next 12 months?

Judy Weber 27:06
Well, the number one goal is to get my books written and published. I already said one was the underlit life. The other one is my methodology for scaling. It's called joyful scaling. And you mentioned it in the intro. You know, I do this with strategy. I love to think and I love to strategize. And I know you do too. And and I think strategy is something that's too often overlooked action is huge, but you've got to have a purpose behind the action. So writing those two books and getting them in print is my goal for the next 12 months.

Andrew Stotz 27:37
Well, that's exciting. I can't wait to get the links to those books to put in the Episode Notes. Because both of them sound fantastic and particularly listening to tell about your mother's journey. It's gonna be amazing So alright, wow. That's a lot listeners in that episode, I must say and it's another story of loss and struggle to keep you winning. My number one goal for the next 12 months is to help you mind listener reduce risk, and increase return in your life. To achieve this I've created our community at my worst investment ever.com And when you join you also get that special discount to my valuation masterclass boot camp. Well, as we conclude, Judy, I want to thank you again for coming on the show. And on behalf of a Stotz Academy I hereby award you alumni status for turning your worst investment ever into your best teaching moment. Do you have any parting words for the audience?

Judy Weber 28:43
Ah, I'm just gonna continue in my mantra all along pursue the impossible.

Andrew Stotz 28:48
Beautiful. That's a wrap on another great story to help us create, grow and protect our well fellow risk takers. This is your words podcast hos Andrew Stotz Singh. I'll see you on the upside.


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About the show & host, Andrew Stotz

Welcome to My Worst Investment Ever podcast hosted by Your Worst Podcast Host, Andrew Stotz, where you will hear stories of loss to keep you winning. In our community, we know that to win in investing you must take the risk, but to win big, you’ve got to reduce it.

Your Worst Podcast Host, Andrew Stotz, Ph.D., CFA, is also the CEO of A. Stotz Investment Research and A. Stotz Academy, which helps people create, grow, measure, and protect their wealth.

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