Dragon's Gold: The Magic of Mindset

Time Freedom Isn’t What You Think: Ryan Twomey on Discipline and Decisive Action

• Justin Mills • Season 1 • Episode 20

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Episode Summary:

What if the real flex isn’t freedom from work—but freedom over your time?

In this episode of Dragon’s Gold: The Magic of Mindset, Ryan Twomey shares how house hacking during COVID sparked a journey toward time freedom, personal growth, and disciplined entrepreneurship.

Key Themes:

  • How “time freedom” isn’t about doing nothing—it’s about having control
  • Why investing in mentorship was the decision that 10X’d his growth
  • The mindset shift from retirement accounts to cash flow and optionality
  • Why imperfect action beats perfect planning
  • How he and his partner scaled to 574+ units in under four years

What You’ll Learn:

  • How to structure your day when no one tells you what to do anymore
  • Why discipline bleeds into every area of your life
  • How Ryan reframed tenant headaches as growth lessons
  • The power of environment, network, and personal clarity
  • Why your first deal doesn’t have to be perfect—it just has to happen


Tools & Weapons:

  • Atomic Habits by James Clear – The power of habit stacking and micro-wins
  • Rich Dad Poor Dad – The foundational mindset shift toward cash flow
  • Passive Income & Wealth Calculators – Ryan’s custom tools for clarity and action
  • “How You Do Anything Is How You Do Everything” – A daily operating principle that keeps him aligned
  • Clarity First – Before you move fast, get clear on why

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About Gold Dragon Investments:
At Gold Dragon Investments, our mission is to bring joy to others by helping them win the game of investing — helping every client become the hero of their financial journey. We believe that wealth is a tool, but joy is the ultimate outcome.
Through meaningful partnerships, we strive to empower our investors to create freedom, and build lasting legacies of purpose, fulfillment, and wealth.

Join Us on the Adventure:

Ladies and gentlemen, welcome once again to another episode of Dragon's Gold, the magic of mindset. Today we have the pleasure of having co-founder of TR Capital Group, Ryan Twomey Ryan, welcome to the show. Thanks for having me on, I appreciate it. Yeah, absolutely brother. Well, as I love to let's just dive right in. Let's go to the origin story. Where did it all begin for Ryan? Yeah, so I co-founded TR Capital Partners. I started my career in financial services, doing wealth planning for all different types of investors before I transitioned to an analyst role with the parent company of the New York Stock Exchange, doing the boring stuff behind the scenes. And the jobs paid well, but took up pretty much all of my time. So the goal of working for myself and having complete control of my schedule, I began investing in real estate with my partner and scaling to have the income pay for my monthly expenses. So that's essentially time freedom. So that allowed me to eventually quit my corporate job and start TR Capital Partners where we've built a community of like-minded investors, primarily sales executives and business owners, and have now acquired ownership in 574 units that pay us every month with a larger goal of adding a thousand to that portfolio over the next three to five years. Awesome, great job, Ryan. Great job in achieving that and making that leap, Jumping from something secure, stable, and monetarily sufficient to make a bet on yourself. So in that, when did you know that you were, we call this the leap of faith. When did you know you wanted something more? So was actually probably during COVID. So Lucas, my partner and I, we were both living at home at the time. We both worked from home because all the offices got shut down. And I think it was a time for reflection for the both of us. So we were looking at where we would be in 10 years, know, doing the jobs we're doing now. Both of us were immediately dissatisfied with our lifestyle we thought we would be. We didn't see a lot of growth in it. We kind of felt like was going to stagnate our growth in the future. So what we did was we met every month, every week, and we were trying to learn something new, and it just happened to be real estate. And that was our vehicle of choice to essentially plan our escape from the W-2s at the time. And after doing that for about six to eight months, we took that leap of faith, started looking at properties. Our first one was a Triplex, and we got outbid on maybe our first four or five offers, but stuck to it and just took that imperfect action. Ended up closing on that property, rented out the units, lived in one unit. as roommates for free with a couple extra hundred bucks for utilities on the top of that. Still have that property today that cash flows for us. And right there, the light bulb went off and we were like, this is this is the avenue to really scale up. So from there, we haven't looked back. That's awesome, buddy. Being able to take that action, keep pushing forward, The offers don't get accepted. Like, man, right? Nope, nope, nope, doors shutting in your face. And then to finally get that one, right? To move in together, right? You learn about people, things that you thought you knew everything, like you learn a lot more about somebody living with them, right? But to take all of those steps to not quit, push forward. And here you are, fast forward, you stole on the property, now it's cashflow and you can rent out the other units, right? So just the growth that comes from that is incredible and kudos to you for pushing through in that. So obviously along the way, there's the gauntlet, the trials and tribulations, the things that we go through, the hardships we experience. What are some of the moments that you would share that you had to grow through? I'd it was probably from that property. So at first it was great. We were living in the unit, so the tenants, guess, for lack of a way to put it, were behaving. They were paying rent on time. They were not being loud and obnoxious, not smoking in the house, which was nice, but we were right in the first floor, so it was easy to maintain that. When we moved out and started scaling and buying more duplexes and triplexes, that's when the issue started. And we had some tenants that just stopped paying rent. And we tried to work with them. Nothing really worked out. Looking back in hindsight, That lesson there was we should have paid attention to detail a little better when screening these people. There was our very first tenant that we had the biggest issue with. We went through the evictions. It costs a lot of money for us, took a long time to get them out of the unit. But in hindsight, it allowed us to become better managers of our assets and screen tenants better, figure out the financial side of things, and create an ideal profile tenant that we've applied to our larger stuff as well and alongside the other properties that we bought. Looking back, that was the biggest gauntlet. We dove in head first, like I said, with Imperfect Action. We didn't really have a tight game plan when we started, but we knew this was an avenue for us. And I think along the way you learn the best, the most lessons by on the job training per se. And you know, can read all the books, you can do all the podcasts, but you're never going to really know what you're doing in depth until you put yourself in the situation. So that was a big wake up call for us. Thankfully I had Lucas beside me the whole time so we could push through those and figure out and game plan together. If it was myself, I don't know where I would be. So I think having a partner in that respect that has a similar mindset goes a long way. think that what you've said there is so incredibly valuable on multiple levels. And one of which being that you didn't have the game plan completely fleshed out when you started. You had an idea, an aspiration, a goal. You didn't entirely know how it was going to work, but you did it. And you took the action anyway. You didn't wait till it was perfect. You didn't wait till you had all the standard operating procedures in place. You just took that leap and you move forward. And you course correct along the way, right? You learn through the school of hard knocks. The other thing that I think that was so valuable, what you said is having Lucas there with you, having a partner, having someone who was like-minded, you each as your own individuals have your own goals and aspirations, but to be aligned in the purpose and the intent to be able to move forward and to support one another. So we call this the fellowship, right? The people that come along this journey with us, whether it be allies or whether it be mentors, right? People that have gone through this, who would you say has been, and ally, someone in the fellowship with you. Yeah, I'd say outside of our direct partnership, which has been huge. I mean, like you just mentioned, we learned from the School of Hard Knocks along the way, especially the beginning. And we've made some pivots that have essentially opened us up to this larger world of opportunities and networks and people. And that's how we've acquired ownership in 574 units since making that pivot. Now, on top of that, which is another part of the action taking with Lucas too, was we found a mentor with Tyler Devereaux, Multifamily Mindset. We went through and hired other coaches outside of that network and we started shifting our perspective from these are expenses to this is an investment itself. So now we have coaches for things that we care about within our business and our lives and it's changed our whole perspective and I think catalyzed our growth like 10X since hiring these people because they're 20 years ahead of us, you know, so we can learn from everything they're doing and essentially pay down our ignorance debt a lot quicker. So there's a number of people that have helped us get to where we are, including our partnerships and the larger assets as well that we've syndicated. You're actually one of them. So that's very nice too. But you know, there's a lot of different people that are involved in it. think wealth building and growth at scale is a team sport. So if someone listening to this hasn't hired that coach or went and networked with that partner or found that mentor, I would say that's probably one of the biggest steps you can take to really catalyze your growth in a big way. quicker than you would ever think and get into rooms with people that are decades ahead of you that you can learn from. Absolutely. Everyone knows something you don't know, learn from them. And oftentimes when you pay for that mentorship, there's a massive value that you gain. One, because they have a vested interest, whoever it is to give you that information and earn that fee, if you will. But also you have a vested interest. You've now made an investment in yourself, right? You put in your hard earned coin to try and make yourself better. And I love how you said, pay down the ignorance debt, right? Ultimately trying to reduce that timeline that it takes for you to understand and have that knowledge. And as you cited earlier, you can read all the books, you can listen to the podcast, you can do all that, but until you get into it, until you just dive in head first and start getting that real life experience, it's all hypothetical, right? You can daydream about it, but what does it feel like? And when you're in it, you get that feeling. And that makes it real. And I feel that so much of the lessons that come from that are through that avenue. So one of the things I'd ask about, Ryan, so trials and tribulations, right? Running that gauntlet. But there's always, I feel, from what I've heard and the stories that I've listened to and people have shared, I'd love to hear, is there a moment you would call the darkest hour? A moment where you're just going to throw in the towel. All that time, effort, energy. It was just felt like you were banging your head against the wall. How'd you come through that? What mindset did you use to pull yourself out of that muck? I wouldn't say I have a specific moment where I felt that way. I think I've definitely felt that way along the journey though. I think a lot of the times we expect growth to be linear. So we think we figure this thing out and then the next step is it's B and then C and then D. It typically never works that way. It's going to be a roller coaster. So shifting my mindset to focus more on taking those failures and the lessons that you learned along the way and then applying them to that next step instead of expecting a linear growth path was a big thing for us. I think that it also helps being surrounded by the right people though. So having the mindset to be intentional with your network, push through the trials and tribulations as you go along, make pivots when new information and knowledge comes to the table. Those are all qualities of, people I've talked to that are successful, right? So learning again, learning from those people ahead of you, studying successful people, the people that are where you are, they've already been there and done that, and applying the same, not just the actions, but the mindset principle behind that as well. And I think the mentorship side on thinking bigger, know, we've all heard, know, the bigger, the bigger action, take the bigger problems you're to have. It's, kind of true. But you just learn different lessons along the way. And I think having people in your corner that have been there and done that really make you push through, especially when it's probably someone that was in your shoes at one point, you know, everyone starts from zero. There's a great quote I heard, the first draft of everything sucks. So If you don't get right the first time, don't beat yourself up. Just take the lesson and move forward. So that mindset has been a big thing for, I think, everyone that I've involved with in partnership wise. And as new information comes, we make a pivot. And usually it's for the better. That's awesome, Ryan. Yeah, think success leaves clues, right? And so when you go along and you follow in the journeys that other people have had and you learn from them and hopefully use the wisdom to learn from their mistakes, right? And that doesn't always work. Sometimes you gotta touch the fire and you get burned and then you learn very, very clearly why it's not good to shove your face into that fire, right? And the hope is that the damage is not so significant that you can't come back from it, right? And with the right mindset, you can come back from anything. So one of the things that I like to think about is the goal. And I feel you've shared a lot of it so far in this conversation, but is there something that you would classify as Dragon's Gold? Achievements, accolades, moments, or mindset shifts that you have experienced and grown through in the journeys that you've taken? think definitely the mindset shift. One thing I didn't take into account when I was thinking smaller per se was everything, every area of your life, the habits that you have kind of bleed into the other areas, if that makes sense. So like the more you work out, typically the more disciplined you become, but that bleeds over into your business or to your relationships or whatever it might be. So I've found myself sometimes where I'm lacking in one area and I feel that bleeding into another and that's when you kind of have to stop, like pump the brakes. and revamp everything and get back on track. Right. So I've found that quote, how you do one thing is how you do everything. It kind of has proven true. And it's something I didn't really think about prior to getting into a business, leaving a W2 and starting my own thing. Because usually when you're a W2, your day is kind of figured out for you. Right. Everything's structured. It's very robotic. least my job was. So I think that was a big thing for me as well, is I'm not only trying to stay in the right mindset for my business, but also everything else, whether that's diet, working out, relationships, networking, adding value to others, even something as simple as putting content out with my message, right? So consistency is key. then discipline is also a big factor in that as well. love that consistency, discipline, taking that action. And I completely agree in the idea that when you're in a W-2 or you're in something that has these boundaries, these bumpers, right, it's very clear. You show up, you punch in, you do what your task is, whether you do it well or not. In theory, if you're getting paid hourly, you're still making a paycheck, right? You punch out and then you go do your thing and you live your life, quote unquote. The reality is as an entrepreneur, when you're putting yourself in this position, you're the one who makes those calls and you can... put in as much or as little effort as you want. And the reality is, is that whether you see it now today or not, putting in that effort ultimately helps to create the foundation that you can grow from. And it gives you the strength, the resiliency, if you have that discipline to be able to grow from that. And I think that unfortunately that's where a lot of people fail. I think a lot of people get that freedom or they get that, that ability to take a break if they want to. And then they take too many breaks. Like they don't try hard enough or, or They find excuses. And I don't mean that to be a negative or, or, I just feel that it's a reality based on the experiences I've had, the conversations I've had and what I've learned and grown from. There's a reason that so many people try, but only so many, a much smaller percentage succeed. And I think it's because when the going gets tough, the tough get going, right? You push through and that much like the quote you said, how you do anything is how you do everything. And If you find yourself straying from that course or that path or that vision that you might have, don't beat yourself up about it. Do acknowledge it. Do understand where it is, grow from it, make the pivots you need to and get yourself back on course. Get yourself back on track, right? And push forward because no one will do it for you except you. Exactly. And I can add to that too, as far as the time, the time aspect goes, you know, I think I work, my goal is time freedom. At first, maybe I thought that was being able to wake up and do whatever the hell I wanted, right? Maybe do nothing that day for really wanted to. That's not really what time freedom is. Time freedom is just having control of your schedule. And even though I have quit my W2, I work more hours now than I did when I had my W2. The thing is I enjoy it and I do sometimes have to push myself to do the task I don't want to do, something small throughout the day. However, it's having control over your schedule, which is the ultimate goal. And a lot of that time comes back to that discipline, right? You have to wake up on time still, even though you don't have to commute to work. You still have to get up and do your thing, if it's at your home office, whatever it might be. So that part of it, I think a lot of people struggle with in the beginning. But again, going back to your daily habits and all the other aspects of your life, eventually those will bleed into the business side. And I think staying consistent with that stuff. for me, it's even just a simple setting up my day. I end the night with setting up tomorrow, right? I have my schedule lined up. I know what I have to do. And there's typically three or four daily actions that you do every day, which builds and compound over time. So I think at the beginning, figuring that out for yourself is a little harder because no one's telling you what to do anymore as with UW2. But again, going back to the whole time freedom thing, it's just part of what you need to figure out. so time blocking and discipline in that regard, even though you don't have to commute to work in the morning, is still one of the probably the biggest factors, even if you put more hours in. I think that that's such a wonderful thing to share is that you take these steps to try and get more time, yet you work more. But the thing that I love the most about what you said is, but you love what you do, right? And that when you are passionate about what you do, when you enjoy what you do, it doesn't feel as much like work, right? I mean, yeah, it's not always easy, but it's enriching, it's empowering. you're adding value to others, dependent upon what you're doing, but I know that you are. And I think that that's so wonderful, not just for yourself, but for all the lives that you touch along the way. so I'm going to ask, uh, speaking of, touching lives. So I call this passing the torch, the legacy and really the hall of heroes, the hall of heroes is if, if there was a giant statue of Ryan Twomey and You're gone from this world, but someone walks by and there's a plaque there and you want it to say a message, something that they want to know about you or that you'd want them to remember. What would that say? think for me, sums up what sums up my journey is take imperfect action as much as you can. And by that, I don't mean just jump into something random and start, you know, actually have some education behind it, but don't stop at the education piece and fall into that analysis paralysis trap. The very first deal I did was a triplex. I didn't know what I was doing. We renovated the place with friends and I paid them a beer and pizza. Like we did not have a plan, right? But we learned along the way. Since then we've 100 X star portfolio from four years ago, right? Went from five units to ownership in over 500. Now each deal has different lessons along the way. I didn't exactly know exactly what I was doing on that first big deal either, but taking that imperfect action, the lessons from the smaller stuff that lead to the bigger things. And again, when new information comes in, being able to make that pivot goes a long way. So. I'm sure there'll be a lot more pivots and changes that we have in the near future and in the long term as well. But I think that imperfect action consistently not only pushes you forward, but also kind of makes you uncomfortable and putting yourself in uncomfortable situations and being able to solve whatever problem that is or just fight through it builds that muscle even more. So it becomes more of a common thing. So I think imperfect action is probably one of the best things someone can do after that initial education phase so you're not stuck in that analysis paralysis, which I think a lot of us do get stuck in. Awesome. Thank you for that, Ryan. Take imperfect action. Yeah, it's so relevant. So what's next? What's the next quest for Ryan and for TR Capital Group? Yeah, so this year, Lucas and I are looking to do about two to three deals. And in the long term, we want to acquire that thousand units over the next three to five in Massachusetts, which is where we're from. So we've built up a pretty good network here. We know you're a part of some of the deals with us here as well. We know we have a strong team behind us. Hopefully we can all work together to achieve that larger goal in the near future. And I think for the super long term, we just want to keep building on our network. and adding value to others in as many ways as possible. So a lot of that will come from networking, building relationships. We were hosting a monthly meetup with our investor club to provide extra resources to people. And that could be tax professionals, economists, just different people that can help them with their own portfolios and just continue to strive for getting better every day. through the growth mindset and excellence is kind of the key. That's awesome. So you talk about resources, I call it tools and weapons, things that you've used or that have helped you along the way. Is there anything that you'd share with the listeners that you feel might be impactful, help them? Yes, so going back to how this all started, it came from clarity. So being super clear on what we want to achieve and that was our why and our how. That's a big thing that my mentors has taught me. And in order to do that, I've created a bunch of resources for myself, which I'm happy to share. You can also find them on our website. But one of them is like passive income calculator, a wealth calculator, all these things that I want to figure out where I was at compared to where I needed to be. So it's kind hard to figure out how to fill that gap if you don't know what that is. So creating simple resources like that go a long way. I also think books have done a lot for me. Atomic Habits is a big one. If you haven't read it, I'm sure most listeners probably have. Rich Dad Poor Dad, like every real estate investor starts there. And just basic financial literacy books, psychology, all of those things will go a long way for not only mindset, but business and your day-to-day action. For me, a lot of those resources come from creating my own based off what I need to accomplish. And then also reading from others, like I said, who are essentially mentors through that literature because they've been there and done that. Thank you for that, Ryan. I appreciate you sharing that. And I think that it's funny earlier you were talking and I thought of Atomic Habits, James Clear. And so hearing you cite that book, I love it. It resonated for sure. Ryan, if any of our listeners want to reach out and connect with you, how can they do so? So you can find me personally on LinkedIn. So that's where I hang out the most, se. That's Ryan Twomey, Real Estate. I think I'm the only one, so you shouldn't have trouble finding me. And to learn more about the opportunities our company offers from TR Capital Partners, you can go to our website, trcapitalpartner.com. We have a ton of educational resources, including free e-books, webinars, articles, different podcasts we've been on. Really just learning from us and what we do as a company. Now, I will say that these deals that we're doing are not for everyone. It takes a very specific person with certain mindset and investment goals. But you can also join our investor club and schedule a call myself for my team. And we can see if it might be a good fit from there and how we can help help you out with your financial or lifestyle goals when it comes to investing and multifamily in general. Awesome, Ryan. All right, I got one last question. It is my favorite question to ask. If you could be any mythical creature, what would you be and why? So I had to do some digging for this one. I would say a hippogriff. And the reason for that is because a lot of what it stands for is decisive action and strength. And a lot of the times in the beginning, it doesn't seem like it's easy to take that new scary step. But that's something that's kind of defined my journey and the partners I've partnered alongside with Journey. So that would be the one I have to go with. I highly, again, going back to that imperfect action, I highly recommend that throw yourself under the fire. It's not as bad as you think. And if you can push through or persist through the downtimes, the uptimes will be that much better. Awesome, so valuable. Ryan, thank you so much for taking the time with us today we appreciate you and I appreciate all the insight you shared with us. Of course, look forward to talking to you again soon. My friends, thank you for joining us once again on our quest to inspire, educate, and empower you to turn your dreams into reality, one mindset shift at a time. We'll see you next time.

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Justin Mills

Host
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Aaron Iler

Producer
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Ryan Twomey

Guest