Fear of Failure in Real Estate Investing: Scale to $1M

In this informal, interview‑style conversation, Toby and Hugh Hilton (joined by Angie) discuss a range of personal and professional topics. They start by detailing Toby’s upcoming 12‑day trip to Ireland, where he will stay in five castles, play golf at Waterville, and explore historic sites—a trip that reflects his lifelong fascination with chivalry and castles. The dialogue then shifts to a weather‑related anecdote about relentless rain in Dallas that has ruined a hay‑baling operation, illustrating the everyday challenges Toby faces. Toby shares how his business has exploded over the past year: from acquiring 300 apartment units to speaking on stages worldwide (including an upcoming engagement in Nairobi, Kenya) and rolling out coaching programs through the JT Group. Central to the conversation is the theme of “fear of failure” in real‑estate investing; Toby explains that many prospective investors hesitate because they lack knowledge and mentorship. He promotes his own book, especially the expanded “Battlefield Mind” chapter, which outlines a mindset framework (the “unshakable self” and “battlefield mind”) for overcoming fear and achieving success. The participants also discuss their friendship, using playful metaphors of sandboxes and castles, and they comment on the personality of JT—his drive, impatience, and the impact of his mentorship. Throughout, the tone remains conversational, enthusiastic, and promotional, with a mix of personal anecdotes, business insights, and mentorship advice.
Chapters
Hey Hugh, how are you, buddy?
Great, great to see you.
How is life in Los Angeles?
Uh, a little, a little crazy with the, uh, how should I say, the, uh, demonstrations and things like that. But, uh, fortunately hasn't gotten down where I live and it's starting to quiet down now, I think.
So that's awesome.
That's awesome.
Yeah, how are you doing, man? We're great. We are, uh, don't think I shared with you in the last couple conversations, but we are jumping on a plane tonight headed to Ireland for 12 days.
Oh, good for you.
So pretty stoked about that, pretty excited. Um, but, uh, doing good. As you know, we're running and gunning with the books and the training and the coaching and You know, focusing on transforming lives.
Good. And what are you going to do in Ireland?
Try to relax. Okay. Try, try.
Whereabouts in Ireland are you going?
Don't get me lying to you. So, and my wife was supposed to be up here, but she's not. But I do know that we're there for 12 days and we're staying in 5 different castles. Um, so this is one of the things that my whole life has been all about— chivalry, castles, all that stuff, you know, King Arthur— and just love that era, love that mindset, loved all that. And so when my daughter graduated from college, we gave her a, you know, a choice of a trip Yeah, I wanted to go to Scotland or Ireland. She wanted to go to Italy, so we ended up going to Italy. But that was the whole deal, is I wanted to go and see the castles and do all that. So not only are we seeing the castles, but we're sleeping in them. We're, we're looking at them. So he wanted to know exactly what, uh, where exactly in Ireland we're staying. Hi.
Oh, well, we're in Waterford. We're in There's like 7 different places we're staying.
The kind of mostly in South, southwestern Ireland then? Are you on northern?
So we don't know where we're jumping on a plane. It's taking us, we're just touring the deal, buddy.
Good, good for you. That'll be fun. We have, uh, you know, Brian and Tony built a golf course in Ireland in Waterville called Hogstun. And it's just delightful. You know, I've been over there 5 or 6 times. I'm a member of the golf course and it's just delightful. And I've played golf courses in Ireland. So great people. You're going to have a great time.
Yes, we're excited. And of course, I don't know if you've kept up with all the weather here in Dallas. It has rained every day, 45 days straight. Wow.
And so you'll be happy to get out of that.
I'm so— my hay, we were supposed to bale my hay. And I know we're talking about business, but that's okay. I got Hugh Hilton. We're going to talk the way you and I always talk. Exactly. But I've got, I've got my, my hay pastures was supposed to be baled about 30 days ago, and there was, there was this rain, and then there, and, and he couldn't get in. And there was one week that they were calling for rain, so he didn't, but it didn't rain. And then it's rained every day. So now the, the hay pastures are full of weeds. They're— it's just terrible. It's going to be a bad crop of hay. So I just want to get away, and hopefully when I come back, it's all done in the summer. Yeah, we'll be into summer.
Yeah, good, good, good. That's great.
So do you want to know where we're going?
Well, if you ask, I just want to—
okay, so day 1, we're in Dublin.
Okay.
Day 2, we're in Waterford.
Okay, which is where the golf course is, right?
It's in Waterville.
Yeah, Waterville. Waterville. Okay.
Day 3, we're in Cork.
Okay.
Day 4, we're in Kerry.
Okay. Yeah.
Day 5, we're in Kerry. Day 6, we're in Galway. And then we go back to Dublin.
Awesome. Yeah, been several of those places. You're gonna have a great time.
We are playing golf. Uh, where, where were we thinking about playing golf at?
I think Waterford is where they said.
Waterford.
I mean, you got to play golf when you're in Ireland, right?
Well, absolutely.
I mean, why would you not go to Ireland and not play golf? That just— that's just not right. You're just not right in the head.
Look at you, you're too much. You're too much. Yeah, no, you're gonna both have a great time.
So, so we're going—
so happy if I get him away from work long enough.
Yeah, we've got so much going on, Hugh, it's unbelievable. We've got so much going on. And the timing, you know, we planned this trip a year ago. And, you know, it's amazing how much has transformed in the last 12 months because 12 months ago we were buying apartments. Life was good. We had taken down about 300 units and the construction was going. Life was good. I had the baby, you know, my granddaughter. So that was basically consumed most of my day. And now 12 months later, I start about 3:30, 4 o'clock in the morning and I shut down about 10, 10:30 at night and I don't even know where the day goes. We've got the books, we've got the coaching, we've got all this stuff with the JT Group that we're rolling out. We've got— I'm on stage, I'm going to— so we get back from Ireland, I'm headed to Kenya to speak in Kenya, on stage in Kenya. Yeah. Wow. In Nairobi. And then we've got 5 more. So it's just Boom! Wow, I met you and life took off. And I mean, it was just that instantaneous. So I didn't even meet you 10 years ago, buddy.
There you go, baby. Just got to do some mindset shift and off you go.
That's right, that's right. The unshakable self and the battlefield mind, those are the things that just skyrocket success to the stratospheres and beyond.
Yeah. Absolutely. Love it, love it, love it, love it, Toby. So, so good to see both of you.
Yeah, it was, you know, um, they kept, you know, we got through JT, we bought a bunch of his books and we dispersed them, gave them out. And so they said because of that you get the 15 minutes with you. And I'm like, I get all the time I want with you, but I'm going to take advantage of this. Exactly. I'm going to take advantage of this because I, you know, I could, I could talk to you every day And likewise, and never get too much of it. There's just so much synergy and so much fun with you. It's, it's unbelievable.
Likewise, my friend. So great, great, great. And I'm enjoying your book. I think it's very well written, your first book. So thank you. Quite through it yet, but because I've been busy on a lot of deals, but very well written. I enjoy it. I love the combination of business and spirituality that you put in the book. So it's just great.
Well, then you really love— so my shipment should be here today, but you're really, really going to love Battlefield Mind, which is chapter 2 of this book expanded. So I took, I took chapter 2 and really broke it down because this, for somebody to take and say, okay, I got to work on my mind, my spirit, and my body, maybe too much to absorb, like trying to eat an elephant. I'm trying to eat the whole hindquarter instead of one bite at a time. So I took chapter 2, which is where I think everything has to start, is in the mind, and built— I wrote out Battlefield Mind, which really digs deep into how you see things, how you live, how you perceive, how you adapt and overcome. So you'll really love it. You really— you'll be my second biggest fan because, of course, the wife has to be— have a contract that says she has to be my biggest fan. And then you'll be my second biggest fan.
No, I will. I will. I'm excited because you're absolutely right. That's what I'm all about.
Yes, sir. And, you know, and when we were there talking and you and I were sharing our parallel life stories. Yeah. That really shared with me that, you know, there's a lot of us out there and I don't know that we all know that everybody's out there, that we've all been through different struggle strategies. And yes, there's 1,000 books out there. But when you can find that alignment and you can find that synergy within a group, then you've got your own built-in support factor of bouncing stuff off. Hey, Hugh, you know, you went through this with the restaurant and I'm going through this. So now that you've been there, done that, because here's the biggest problem with society and business is we don't know how the book ends.
Right.
But you do. You went through it with the CDC and you went through all that. So you know how that book and that chapter ended. So now I'm facing this over here, Hugh. How would you perceive it knowing what you know? Because I'm scared to death because I don't know what's going to happen. So those are things that are so awesome to be able to correlate with.
Yeah, no, no, no, I agree. And as we talked about, I think a lot of it just has to do with, with focusing in on your curiosity and creativity. And a lot of people get scared because they're not spending any time on trying to come up with a creative solution. They're just scared of failing, right? Focused on the failing instead of focusing on the success through a creative idea. So you're absolutely right.
You know, I was doing a podcast yesterday down in Dallas, and the guy asked me, said, so why do you think is the biggest reason why people don't get into real estate? And I said, fear of failure. Yeah, it's fear of failure. They're afraid that if they've got $20,000, $30,000, $40,000, $50,000, $200,000 set aside and that they put it into a real estate deal and they lose it, now they're at zero. And so they just try to hold on to it. And so one of the deals that we're doing with Uncle Shake, Unshakeable Self, and the coaching that we're doing in real estate now is getting them past that. Because the reason why you're scared is because you don't know what you don't know. But if you bring in a coach, you bring in a mentor, like, you can guide through that. Now that relieves or, or, or lessens that fear. Yes. And therefore you have a higher probability of success. Now you take the $200 and turn into $250, which turns into $400, which turns into a million, and so on and so forth. But now if we can release that fear, we can guide you through success. And that's so important.
Completely agree with you, Toby. Couldn't, couldn't have said it better myself.
So, uh, that means a lot, buddy. I mean, I have so much respect for you, it's unbelievable.
Oh, well, you know, I, I likewise, my friend. I think, as you said, we're, we're like two kids in a sandbox, you know, and we got—
and we brought the same damn toys. It's not like—
exactly, fill up the little bucket of sand and hand it to each other.
That's right, that's right. I use your shovel, you use my bucket, and we just build castles all around us, right? Exactly. Exactly.
So that's, that's what, that's what I talk about. I say, hey, you know, when you're little kids and you're playing, you're not having fun, you don't continue playing. You get up and go over and have some fun with somebody else. So I love just when you bump into someone, as you say, like you and I have bumped into each other. We, we are like playmates.
Yes.
And we, we have fun together and we have a blast.
And it's such short— and, you know, I'm stoked. I told Angie, I said, I don't care what anybody else wants me to do. When JT is going to Los Angeles to do this deal with Hugh, we are there. We're going to be there a day early, a day late. And she's like, you never do that. You're always in and out. So now you're going to go and you're going to spend an extra day there and an extra day. That's unbelievable. I said, this is Hugh. This is my boy Hugh. Yes. And we're going to figure out some time, whether it's on the course, I don't care, but we're going to be there and we're going to enjoy our time with Hugh. We don't get enough of you time.
But quintessential JT response. Oh, really?
You're going to come in and spend some extra time? Really?
You don't do that for me.
That's right. That's right. That's right. That's so funny. But she gets so mad because when we were there for your deal, you know, we were there for that afternoon and we were flying out that evening. And she's— and originally she's like, well, could we come in and, you know, stay a day? I said, no, we're going in. We're going to have our time with you, our hour with you. And then we got to get back. We got work to do. And of course, you know, but now, now, well, now you're going to go in a day early, stay a day longer. Really?
You and I are great. I just love it when we get under JT's, you know, needle him a little bit. It's just great. Yeah.
Oh, I needle him every day. He blew me up the other day. I'm telling you, he was getting ready to do— he's removed the JT89. He closed it out. But now he's doing a daily newscast, like a 7-minute newscast. And he had his green screen up and was getting ready to start it. But I had done something that really irritated him. He faced it. I can't believe you're doing this. What are you— I'm like, okay, sure, you bet. But I like it. All right. He's like— he just hangs up. I'm like, yes, I got under his skin again.
Oh, that's pretty hard to do. That's pretty hard to do, too, you know?
Yeah.
He's a great guy.
So he's— and you and I have said, you know, the guy's got a heart of gold. He's all about trying to betterment of man. He's just— he's so driven and so direct and he's so focused that I think sometimes he loses the relationship because of the 'here's where I want you to be and I can't believe you're not already there' mindset.
Right.
Right.
It's just respected.
Yeah, absolutely. Sometimes it gets a little impatient.
Yeah, patience was never, never in his desire. When the DNA was being rolled out, they saw patience and said, no, we're just leaving that out.
Right, he said, I think I'll skip that one. You don't have to add that to my DNA.
That's right. Yeah, yeah, we're gonna, we're gonna throw this guy out into the world with zero patience, zero compassion, and then watch him be a multi-millionaire, potentially a billionaire, and we're going to show the world it can be done.
Yeah, absolutely. Exactly. You can't— you can go 24/7 nonstop for eternity.
Yeah. Yeah.
He's got this one little patience. Yeah. Yeah.
He doesn't even have patience. I don't know. We get on the calls with him every now and then. He's in his backyard. He has zero patience for the geese. I don't know if you ever had that conversation with him, but the geese will come out into— because he's right there on the water and the geese will come out there and he's got a little green laser and he runs them off. And sometimes it's upstairs. And I mean, he spins out, he completely loses track of the conversation because these geese are walking across his yard getting ready to poop on it. Exactly.
No, hey, listen, that's one thing that I'm in complete alignment because I grew up on a lake. The geese used to come poop on the lake.
Poop everywhere. I know.
My job was to keep them off the grass as well. So that's pretty— but kudos to him because he actually came up using a laser. That's really—
He had a little green laser.
Doesn't have to get close to them at all. Can shoot them from laser from 200 yards away. Yeah, that's great.
Yeah, I, I probably would be getting an airsoft gun and start popping them so that they get a little bit of soreness, right?
He goes, I don't need that, use the laser from my balcony here. That's great.
That's awesome.
Love it, love it, love it, love it. So, well, I think we're about done, but you have a wonderful trip to Ireland. Can't wait to reconnect with you when you get back.
Okay, and your package should go out today if the other book comes in. And you'll get it, and then we'll, uh, we'll catch up with you soon enough, my man.
That'd be awesome. Okay, best to you, Angie. Okay.










