Episode 575: Redefining Retirement as the Day All Your Choices Open Up with Doug Bennett
30 Sept 2026 · 27 min
In this Smart Real Estate Coach Podcast episode, host Chris Prefontaine interviews Doug Bennett, founder of DB Wealth Planning & Preservation, bestselling author, and host of the Goals Do Come True podcast. The conversation explores how to redefine retirement as a "work‑optional" date, the psychological shift required to move from saving to spending, and the importance of giving oneself permission to enjoy wealth. Doug shares his personal journey—including the loss of his parents, a near‑fatal motorcycle accident, near‑bankruptcy, and the sale of his business for over £1 million—illustrating resilience and reinvention. He outlines his goal‑setting framework, which starts with simple, time‑based goals and scales to income‑based milestones (e.g., £100 k, £250 k, £500 k), emphasizing the power of writing goals down and progressively raising them. The discussion also covers his book Think Simple, Win Big, which distills these lessons for entrepreneurs. Throughout, Doug promotes his 3 Payday System—a creative real‑estate deal structure that delivers cash flow at three stages (immediate, medium‑term, long‑term)—and invites listeners to a free discovery call, a financial‑struggle‑to‑success guide, and his podcast. The episode concludes with a sponsor spot for REI BlackBook, a software platform that integrates lead generation, deal tracking, and closing tools for real‑estate investors. Key takeaways include redefining retirement, confronting psychological barriers to wealth, using incremental goal‑setting, leveraging creative deal structures, and taking immediate action via the provided resources.
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Welcome to the Smart Real Estate Coach Podcast, your source for actionable, real-life, practical investing advice. Each week we help you make a quantum leap somewhere in your business, your finances, and/or your life. Subscribe, leave a rating and review, and learn more at smartrealestatecoachpodcast.com. All right, welcome to the Smart Real Estate Coach Podcast, where we cut through all the noise and show you exactly how to get deals done in today's market. Most importantly, everyone's asking, is today's Is the real estate market the best thing to be in? Yes, it's the best thing. I'm Chris Prefontaine, and if you're serious about creating income and wealth through real estate, you're in the right place. Today, I'm going to hang out with Mr. Doug Bennett. Doug is the founder of DB Wealth Planning and Preservation. He's a bestselling author. He's an internationally well-known speaker, and he's the host of the globally ranked Goals Do Come True podcast.
That's right.
That's right down there, guys. Goals Do Come True podcast. For over 30 years, he's helped business owners like you and I and professionals create financial freedom and understand when work becomes optional. Cool topic. That's a brain thing for you to think about right there. Doug's own journey, just to give you some context, included rebuilding after financial setbacks, very similar to mine. So, I wanted to have him on the show and chat about this openly and candidly. And on top of that, luckily, I did not have to go through this, surviving a motorcycle accident. at 95 miles an hour on the Autobahn in Germany. Didn't put him off motorcycles remarkably. And today, he shares lessons of resilience, reinvention, goal setting that have literally shaped his business and his life as you're going to hear. All right, Doug. Good to see you again and welcome to the show, my friend. After that little bit of a backdrop about you, welcome.
Well, thanks for having me aboard. On board, thanks.
Yeah, you bet. Doug, it was interesting. I was looking at some of your stuff since we met on your show, which I just told everybody to write down. But what caught me, and this is probably one of a gazillion things you talk about, but what caught me was something about goal setting and more of a definitive plan versus, now this is going to be my words, versus kind of would-be-nice goals, right? So, can you talk about goal setting a little bit as far as a definitive plan and anything else you want to kind of fill in the blanks with? And maybe before you do that, just a little kind of behind the green curtain on how Doug arrived here? Like, what do you, how'd you get to where you are now?
Well, I'm 63 now, so, you know, it's been a long, weavy path. I've been a mortgage broker and financial advisor for the vast majority of my life. Um, both my parents passed away in 2006, 2007, within 12 weeks of each other. And that was at that point, being the oldest of 4 kids and a financial advisor, I got to deal with their stuff. So at that point, I found out that actually my dad had or could have had the opportunity to retire a few years earlier and then spend time with my mum who had cancer and stuff, but he didn't know about it. So that made me a little bit sick about my position as a financial advisor. So now my raison d'être, if you like, is to talk to business owners and help them get to that work-optional position sooner rather than later so that they're spending life enjoying times, you know, enjoying spending the money that they've created rather than sort of keep going for more, keep going for more. Having, I'm gonna, you know, retire next year. I'll, you know, we'll do this next year, next, next, next. It's always pushed back, pushed back. So, you know, I've made it my goal, anybody that I deal with, it's like, right, okay, we're gonna tell you when work is optional, give you that date.
Right.
Demonstrate that you're not, you know, you can live the rest of your life without fear of running out of money. And give you permission to spend it.
I love it. So maybe that's going to, okay, that's going to combine a couple of questions I have then with what I opened up with my comment just from researching you and talking with you. And that is, is it strictly money related as a financial planner or are there other variables that go into the work optional plan?
No, it's There's a massive amount of psychological stuff that goes into it. Now, I'm not trained psychologically. I've just been through the university of life. I've got 2 divorces behind me, serious motorcycle accident, near bankruptcy. So it's like a whole history of life. So as a consequence, I can bring that experience in and go, should be doing this. And it takes a while for people to go from the saving stage into the spending stage. It's a big psychological shift. So I spend most of my time giving them permission to spend money and revisiting their situation and, you know, what is it that you want to do? And, you know, here's the money for it and get out and do it and book it now. And You know, it's all of that sort of stuff as well. I don't hang back on that. As I say, demonstrated to me my parents both dying. My dad said to my mom, look, it's gonna be great when we retire, you know, and the target date was 65. She died 63, and then that was it for him, you know, 'cause he'd failed, which is the reason I think he went so quickly after her, to be fair. So it's like you, we get one shot at life. We only get one opportunity to live on this planet and do stuff and make a difference to either people's lives or our own lives. So just do it. Just do it.
Uh, I, I couldn't agree more, Doug. I mean, I'm only 3 years behind you, right? So I, so we tend to think of things a little differently than, than say, uh, someone in their 20s or 30s. So I'm, I'm tracking with you. Okay. Talk about right behind you. So those of you listening, not watching, is your book Think Simple, Win Big. Can you talk about that a little bit just to tie some of this together?
Yeah. I mean, Think Simple, Win Big. Well, basically I'm a big goal setter, right? And I'd set my goals up and One of the goals was always income-based. You always have an income-based goal and we maybe come back to that in a minute. And I sold a big chunk of my business for just shy, well, just a smidge over £1 million. And trust me, £1 million isn't enough money for most people. It's not enough money if you, you know, if you want to live a decent life, it's not enough money. So. So I thought, right, okay, I've got, I wrote a book called Goals Do Come True, which is the name of my podcast.
Yeah.
And that was my journey to getting to the stage of selling, you know, selling the business. And it was predominantly aimed at my peers in the financial services industry. So they had a lot of reference to the Million Dollar Roundtable and and life insurance sales and all of that sort of stuff. And then I was talking to Georgia who helped me with the book and she said, there's actually a lot of good stuff in here that would help any entrepreneur.
Anyway.
One that, you know, anybody that's aspiring to be an entrepreneur or anybody that's losing the little bit of shine that they had because, you know, I call it the entrepreneurial promise. We decide that we're going to become an entrepreneur, we're going to set our business up and we're going to have more free time, we're going to have better holidays and a better car and we swap our 9 till 5 job and we end up working from 7 AM to 11 PM most days, don't have weekends and all the rest of it because all of a sudden you're now doing everything. So it was all the lessons that I learned from that period and I just put it into the steps and it's like, you know, these are the things that you should consider and it might help you get there a little bit quicker. Um, and you know, anybody wants to reach out, I'm happy to send a signed copy. Oh, that's awesome. At my expense. I mean, of course, because it's then signed, it's not worth anything. But anyway, hey.
No, that's awesome. I appreciate you doing that. As you know, we do that and there's not too many people that do that just at our own expense. So, thank you for that. So, then let's do this, Doug, while they're listening to that generous comment. How can they reach you? Anything you want to share whatsoever around that, then let's make sure they have it so they can get that book because I just want a big explanation point behind your history because I'm not too far behind you. I don't care what's in the book and what comes out of the conversation. It's a whole lot more than someone looking, say, to quote unquote get coached by someone who's not had the life experiences you have. There's a lot of value there. And I can't stress that enough. I scream about it on this podcast all the time. I want people that have been through, that's how you and I connected, been through a couple decades or 3 of worth of stuff and it's super helpful. So how can they reach you? You know, it doesn't matter if you're brand new to real estate or if you've been doing this for several years or a whole bunch of years. I learned the hard way back during the crash that doing creative deals is much better. It's a much better path in real estate in general than let's call it the old way, getting paid once, using banks, signing personally. 3 paydays, getting paid 3 times on a deal, guys, it's better. 3 ways, not 1. money now, money over time, and money long-term. And I don't care if you're in an up, down, sideways market, it doesn't matter. You can and should operate with the utmost confidence. There's literally nothing I love more than helping people create systems and simple systems and processes to become massively successful with our 3 Payday System. In doing so, in literally any market, and doing it geographically literally anywhere. So if you've been learning and learning and listening and studying and not taking action, I'm telling you after going through it myself, It's costing you tens of thousands, if not hundreds of thousands of dollars, by not taking action on the 3 paydays the way you should be getting paid. Many of the people that were brand new, just like you, that joined our community have fast-tracked their startup. Now, I mean, wouldn't that be ideal if you said, okay, should I go fast or slow? Should I take action now or later? It's costing you too much money to wait. Each one of you are at a point in your life, I'm sure, Where you want things to be easier, you want things to be better for you and your family. You probably realize that you not only want more, but you deserve more in this life. So, to be able to give your family everything they want, build a legacy for you personally too, and to have time freedom to start enjoying life, frankly, whatever else you're seeking. And for some of you, now's the time, for example, to just focus on security. Maybe it's building a big solid bank account for retirement. We take these things super, super seriously. And it's my life's biggest reward to help you achieve them. I want to give you a free discovery session with our team. It's free. It's 15 or 20 minutes. You have zero to lose and everything to gain. And to understand how you might fit into the 3 Payday System that we've done now in over 80 markets as of this filming, go to smartrealestatecoachpodcast.com/discovery for a free call with our team.
smartrealestatecoachpodcast.com/discovery.
Because it's not whether or not you can do it or whether or not you fit. You can do it. It's whether or not you'll take action and do what it takes. And we can guide you through that process. smartrealestatecoachpodcast.com/discovery. We'll see you soon.
Well, my, my website is dougbennett.co.uk. So, you know, doug@dougbennett.co.uk if you want to email me directly. And your team has very kindly come up with, so they can get a little bit, my From Financial Struggle to Financial Success. So if they go to smartrealestatecoach.com/doug, couldn't be any easier. You click that link and we'll send you my guide to financial, from financial struggle to financial success. And, you know, ordinarily you'd have a massive follow-up and, you know, get emails every 30 seconds trying to convince you to do stuff. I haven't got time for that. Okay. So you'll hear from me occasionally.
So that's great.
Don't worry about that sort of stuff.
Our styles are similar, Doug. That's why you're here. You mentioned in your— when you talk about the last journey there, you mentioned you'll come back to income-based goals Versus maybe other goals. Can you comment on that or where you're going with that?
Yeah. Well, so I started writing my goals back in 2004. Okay. So this is the little original goals book where I started. And as entrepreneurs go, you know, you do something for a period of time and then some new shiny object comes along and you get distracted by it. And, you know, the things that you do regularly disappear. And I found this goals book about 4 to 6 years, 4 or 5 years later. And amazingly, of the early goals that I'd written down, I'd completed 10 out of 11 of them. So, you know, the writing of the goals works. And, you know, learning that lesson, I then started again because, as I say, 2010, I was on the edge of bankruptcy. So I set my monetary goal and it was £100,000, all right, as a reasonable target for anybody to make a decent living, £100,000. That was pounds. And now once you start employing a couple of staff because you need to do that to, you know, make your life easier, you've got to delegate to elevate your life. It's, you know, it's very, very simple. It's a simple structure, you know, you need to be earning more. So having hit the $100K turnover, I then went for $100K net profit and then it was $100K on my tax return. So each time I was moving up the goal, but it was having a bigger effect on me, but still keeping the $100K figure. Then of course, you know, when you get to confident levels, then you just double it because that sort of makes sense, you know. So then I went to 200, then I went to 250. And the mad— so going against the doubling side of things, but the mad thing is I was getting close to the 200 figure. So I thought, oh, you know, I just pushed myself this next year. I did £250,000. And then at that time, my wife at that time, she's no longer my wife, but She was doing my accounts and she did my accounts for me and all of my little income bits and pieces, because you have multiple streams of income, they all came to £250,268 and my goal was £250,000. So it was like, holy moly, what's going on here? You know? So then I did double it. I went to half a million because it's like, right, well, if I'd taken it from £200,000 to £250,000 and I hit it, well then why not? Why not see what happens? And I had a conversation with a firm and they contacted me, they wanted to buy part of my business and they paid me $500,000 in 2019 and another $500,000 and something in 2020. It's like, holy moly, you know, or I think, yeah, I'll keep it clean. I'll keep it clean.
Right.
So, so that was, you know, that was it. So I got this money and then it's like, and if you're not used to money, it disappears very, very quickly. That's another thing to bear in mind. So, you know, make sure that you get some professional help. Maybe I should have got more professional help with my own money. But, you know, they say a plumber's tap often drips. So, well, and then I got divorced, then I got divorced. So, you know, half of it's gone to my ex-wife now. So there we go. I'm still building.
Well, Doug, if we know that that's like, 'cause that's been the case of me, like when we write it down scarily in the positive sense, it comes about, right? So how much, how much of this do you think is us blocking ourselves? And if it is all of us blocking ourselves, 'cause you could have Easily wrote down a bigger amount. What have you done or what can they do? What's a nugget or 2 that they can use to break through some of the blocks? Because at the live, what we call Deal Labs, the events I run right here, the small private ones, I tell them, you're the only thing stopping you. Like literally you are the only thing in your way. And it's usually what you said, like, oh, they won't reach that high. So if they don't reach that high, they're never going to get it. So any thoughts on that? It's like, It's broad, but super powerful.
Well, so very often it's because people haven't necessarily used goals and so they don't believe that they work. So maybe you need to cut your teeth on some smaller ones to start with and some simple ones. You know, I mean, the early ones from 2004 were, I am an excellent timekeeper. You know, I was quite simple. But so you turn up 10 minutes beforehand, you know, to every appointment, you know. And then there was the, I ride a Harley-Davidson this and a Harley-Davidson that. And, you know, my, my Fat Boy, Harley-Davidson Fat Boy, which was on the list. Uh, I just bought that back from Portugal. I've done 2,300-mile round trip to Portugal and back just these last 18 days. You've got to lead by example, right? If you're going to teach people to do stuff and seize the day and get on and do it, you've got to lead by example. So, um, yeah, you just get, you know, get on with it. But maybe cut your teeth on some smaller ones to start with. Get the belief, get the faith.
Get the edge.
And then, yeah, and then start, then start ramping them up. Because everybody, you know, there's always been somebody else that's done whatever goal you've achieved.
Oh, it's—
Unless it's something completely unique. So even if you have to study them, all right, to find out how they did it, or get a mentor, and then people go, oh my goodness, it's like, you know, it's going to cost me money. It's like, well, okay, do it yourself and take 5 years to do it. Or get a mentor and take a year to do it.
Gonna be more than a year.
Then you've got 4 years of like the reward. It should be that simple. And not only that, you know, we all get ourselves in debt to go through university and then we stop learning. We've invested money to go through university. Well, you know, or college or whatever. thing is that you guys have. And it's like, and then we stop. No, carry it on. You got to carry it on.
Not only that, but we don't blink twice about, I'm gonna say, sometimes blowing $50,000, $60,000, $100,000 to do that college or university, but we'll second-guess, I don't know, use a number, $5,000 training program.
Crazy. Yeah, yeah, absolutely. And you're still paying for the debt. And yeah, and you know, It's like you've still got to learn. And, and all the stuff that you learn at university, I mean, you know, if you're in your mid-30s, that was like 15 years ago.
Hmm.
You're in the 40s, it's 20 years ago, you know. Yeah, you need to get with the beat. And, and, you know, if somebody's been there and done that already, you know, just get on their little coattails and run after them.
Yeah, I think I spent 4 years, almost 4 years, uh, when I got beat up by the crash around the same time you did. Um, for 10, you said 2010, for me it was 8 to 12, but not until I reached out to someone to realize that what I went through was hardly nothing in their eyes, right? It was just getting with that. It was the proximity, the association of someone else. That's all it was.
Yeah.
Do you take on people now, Doug? Um, Inside and outside the financial world as far as coaching and mentoring them, or do you not? Do you do that still?
Yeah, I still do that on occasion. It's not the main feature. I think, you know, I do make a bigger difference to people's financial lives in that regard. But yeah, you know, there's lots of lessons to be learned and I'm always happy to You know, share a few nuggets. Well, my book will have a few, and if you reach out and you're nice to me, I'll be nice back.
And, and they can get on your Goals Do Come True podcast, right? Because they get a lot of you there.
Yeah. Oh yeah, definitely.
That would make sense.
Listen to them. Listen around there.
Doug, what, um, what didn't I ask you? Or perhaps a nugget you want to share? Uh, I had a train of thought I was going in because I had got a chance to meet you before, but What didn't I ask you that you'd like to share with these guys, the smart listeners?
Well, if we're talking about everybody's aiming for retirement, right? That's the thing. And it's not retirement. It just isn't retirement. It's the day that you are comfortable and that all of the choices open for you. Yeah.
I don't like the word retirement either. I'm with you.
Yeah, I mean, you know, it's like I, I, I should be thinking about it really next 2 or 3 years, but I was gonna say I've just been away for 18 days on my motorbike. I'm, I'm doing podcasts, I'm doing my own podcast, I'm changing people's lives. You know, I can do it from wherever. I can do it back from the back of a motorhome if need be, which is probably on the Horizon.
It's a nice little plant of a goal there.
You know, why, why, why would I stop? But knowing that I could stop takes a lot of the stress away. So, you know, that I think that's your big thing. You know, if you're, if your financial advisor isn't doing that sort of planning with you, get another one.
Yeah. Love it. Love the eye-opening comments, Doug, and the candor and right straight to the point. I appreciate you being on. Guys, all the show notes will have all the links that Doug and/or I mentioned. The main one, smartrealestatecoach.com/doug, and you can get into his ecosphere. And Doug, always good to hang out with you, buddy. We'll have to recircle the wagons and do the podcast again in another 6 months or so. Good to see you.
No problem at all. Cheers.
Thanks, buddy.
Cheers, Chris. Bye.
All right, guys, that wraps up our time together today with Doug. I hope you found that valuable. Please make sure you subscribe to your favorite podcast platform so you don't miss any episodes. No fluff here, no theory, just real-world stuff and real-world strategies. If you're ready to implement what you're hearing, head over to smartrealestatecoach.com. We're going to help you build this the right way. See you next week. Hey guys, are you simply sick of juggling a dozen different software tools for your real estate business? I know I was, and I know I'm not a tech person, so it was frustrating. A subscription for this, you get a subscription for that, and they don't even work together out of the box. That's very frustrating, especially in the real estate world where your best time spent is going to be out in the field or on the phone with sellers. And now you're stuck hiring a tech guru just to make all that sync up. So let's ditch the chaos and let REI BlackBook handle everything. Automate your lead follow-up, track every deal, analyze things quickly for you, make offers all in one platform. In fact, with the Wicked Smart platform, we now have access— if you're in the Wicked Smart community, to all the other associates' properties. Can you imagine that? So you're brand new in the business perhaps, and your seller looks on your website and sees 20, 30, 40 properties, instant credibility. So you're going to get everything on REI Black Book from our custom workflows for lead generation all the way to closing. It has it covered. Try it today for just a buck. $1, guys. Visit smartrealestatecoach.com/reibb. hyphen D-D. smartrealestatecoach.com/reiboy-dog. All right. Thanks for tuning in to the Smart Real Estate Coach Podcast. If you got value from today's episode, guys, be sure to subscribe so you never miss a future episode. It literally takes one nugget to access some of the things we're doing. And when you're talking the amount of the size, rather, the paydays, it's an opportunity cost that you can't let go. So don't miss an episode. And for goodness' sake, share it with someone who needs to hear it. If you're ready to find your best path for getting started on your real estate investing journey in general, head over to smartrealestatecoach.com/getstarted. We're going to help you take the guesswork out of your next steps. See you in the next episode.
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