Built Without Permission
Built Without Permission is the podcast for entrepreneurs who never waited for someone to hand them the blueprint.
Hosted by Matthew Mak, a former architect turned tow truck operator, landscaper, and equipment rental company owner, this show offers a raw, unfiltered look at what it actually takes to build multiple businesses from the ground up without a roadmap, a safety net, or anyone's approval.
Every episode dives into the real decisions, hard pivots, expensive lessons, and unconventional strategies that separate the people who talk about building something from the ones who actually do it. No theory. No fluff. No permission needed.
Whether you are a tradesperson with an entrepreneurial itch, a business owner navigating your next reinvention, or someone who has been told your path does not make sense, Built Without Permission is proof that the best businesses are rarely built by the book.
This is the show for the ones who break ground before they feel ready.
Built Without Permission
Hands Off, Hands Down the Best Scott Dinan on Managing -1M+ Luxury Vacation Assets Across Manatee, Sarasota & Pinellas
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
In episode 18 of Built Without Permission, Matthew Mak interviews Scott Dinan, founder of Trust First Management, as he shares how this leadership shift helped create a culture where team members began taking initiative—including one employee who recently built an entire work-order app without being asked.
Tune in for an inspiring conversation about building your future, leading with purpose, and taking action one step at a time.
TIMESTAMPS
[00:00:06] Introducing Built Without Permission and Scott Dinan.
[00:01:19] The moment Scott realized he was ready to start his own business.
[00:02:20] Why making $200,000 revealed the limits of a W-2 career.
[00:02:52] Starting a business while becoming a first-time parent.
[00:04:12] The importance of having a supportive spouse.
[00:05:08] Surviving two back-to-back hurricanes in Florida.
[00:06:06] What kept Scott from quitting when the business was losing money.
[00:07:12] Building Trust First Management and managing 50 properties.
[00:08:05] Vacation rentals, real estate, and serving Canadian clients.
[00:09:13] What real success looks like behind the scenes.
[00:10:12] Building a team around shared vision and individual dreams.
[00:11:06] How better leadership created greater team initiative.
[00:12:26] Using AI and technology to transform business operations.
[00:13:16] Starting a business while maintaining financial security.
[00:14:12] Taking action and getting 1% better every day.
[00:15:13] Overthinking, mindset, and creating your own reality.
[00:15:50] Why Scott identifies with Batman.
[00:17:41] What “Built Without Permission” means to Scott.
[00:18:12] Why don't you need permission to create something meaningful?
[00:19:17] The danger of waiting until it's too late.
[00:20:53] Parenting, programming, and breaking self-imposed boundaries.
[00:21:30] Where to find Scott Dinan and Trust First Management.
[00:22:15] Consistency, social media, and embracing the haters.
[00:22:40] Final thoughts and building without permission.
QUOTES
- "At the end of the day, why do you need permission?" – Scott Dinan
- "If you have an idea, create it." – Scott Dinan
- "If you're waiting for permission, you're already behind." – Matthew Mak
SOCIAL MEDIA LINKS
Matthew Mak
Instagram: https://www.instagram.com/mattmak.builds/
Facebook: https://www.facebook.com/matt.ozoriomak
LinkedIn: https://www.linkedin.com/in/matthew-mak-715bb825/
J and J Equipment Rental
Instagram: https://www.instagram.com/jandjequipmentrental/
Facebook: https://www.facebook.com/people/JJ-Equipment-Rental/
LinkedIn: https://ca.linkedin.com/company/j-j-equipment-rental
Scott Dinan
Instagram: https://www.instagram.com/scott.dinan/
LinkedIn: https://www.linkedin.com/in/scott-dinan-545b1991/
Facebook: https://www.facebook.com/smdinan/
You ever notice the people doing the most aren't asking for advice? This is built without permission. I'm Matthew Mak. Before I ever drew a blueprint or signed a business deal, I was folding suits, hauling snow, and washing glasses until 2 a.m. They came architecture, tow trucks, and a built business from the ground up with my partner. No blueprint, no safety net, no approval. Just real stories, hard pivots, and what it actually takes to build something from nothing. Let's get to work. So we got Scott here joining me on Built Without Permission. Glad to have you here. Scott, yes, sir. Tell us. How are you doing?
Scott DinanI'm alive, man. So I'm doing wonderful. And it's an honor to be here. So I appreciate you having me on.
Matthew MakLikewise, man. And I'm always appreciative of the time that people share with me as well. So uh all right, let's uh let's get to it. Um, so tell us, uh what's the one moment that made you realize you know what you're doing, or sorry, that you were done waiting for permission to start what you're doing, and what it is it that you do?
Scott DinanYeah, good question. So I think it actually started in 2022. Okay. This was towards the end of COVID, right? So a very unique time in history. And at the time I was working at W 2, um, I was actually in healthcare staffing. And ironically, COVID actually was a blessing. So, you know, during COVID, we got a ton of government contracts, right? Where we were basically staffing hospitals around the country. And for the first time in my staffing career, I made multiple six figures. And most money I'd ever made up until that point. But it was interesting because I had a realization that one, $200,000 isn't actually that much money. And two, I was capped, right? Like this was a once-in-a-lifetime just unique situation that allowed me to make that much money.
Matthew MakYeah.
Scott DinanAnd I realized, you know, my future really relies on the vehicle I'm in. And at that time, it was that company.
Matthew MakYes.
Scott DinanAnd essentially I was just working to make their dreams come true. And that was my ceiling. Right. So it was really a pivotal moment. We also had our first kid right around that same time. And at that time, I spoke to my wife. I was like, look, I think if there's a time to do this, you know, start a business, it's it's now. So that was the beginning of the journey.
Matthew MakYeah. And it's crazy because like the the the time too, like how you mentioned, like, you know, you're having your first child, and then this is like a big move, right? That you're deciding to do, and then for sure your wife being your biggest supporter to doing so, right? All that helps. Right. Like the wife part specifically, right? So important. So important. Yeah, because it could go totally different, and then you know, you may not have taken that leap, right? And then, like, so now where you were before, before you took that jump, uh, and realized that you wanted to do your own thing, uh, how long were you working there for? Eight years. So eight years, yeah. So I can I can totally relate to that, right? Like, even like for myself, uh, what I do is uh equipment rentals. And prior to that, I was an architecture designing residential homes for 10 years, right? And then I kid you not, at that eight-year mark was when I said there's something more to do. So that's where my ceiling was too, right? And then I just got into what I was doing, yeah. So it's you know, uh, when you're sharing your experiences with other uh others, it seems like everyone has similar, you know, that you can relate to, right? Which is which is really cool. Yeah, right. And you wouldn't know unless you talk about it.
Scott DinanYeah, and the wife thing's a big thing because I think we all have seen people that have so much potential, but of course their spouses hold them back, you know, they don't have that support system, and I'll tell you, man, I couldn't do it without my wife. She is the biggest blessing ever.
Matthew MakSo that's yeah, that's absolutely same, same here, man. Hands down. Like, I wouldn't be able to operate at home with kids and everything. Like, I got three. I'm ready to do it. You do two? Yeah, man. There you go. So when I'm coming out of Florida, we're gonna have a hangout.
Scott DinanIt'll be a big party.
Matthew MakYeah, that's all right, man. As long as the kids have fun, that's all that really matters. Us is just simple, easy beach, water, beer, we're good.
Scott DinanJust give them a pool and yeah, we're good to go.
Matthew MakSo awesome, awesome, man. Uh, all right. So now tell us, um, was there ever a moment that you almost quit like after you started and what stopped you? Yeah, there's probably been a few.
Scott DinanUm, you know, I think the most uh memorable moment would be towards the end of 2024, we actually had two back-to-back hurricanes here in Florida.
Matthew MakYeah, I remember that.
Scott DinanIt was horrible. Um, talk about PTSD, you know. Yeah, we basically were working overtime, had to work harder than ever before, but we're actually not making any money. We're actually losing money, right? Because we have to relocate guests. You know, a bunch of our rentals were flooded, we actually lost properties. It was a very stressful time, right? Owners are stressed, everyone's asking for updates. You know, you're doing all this extra work and you know you're actually losing money. It was a very interesting dynamic. So that was definitely a time that tested me. Um, but we we got through it, and um and what was the second part of that question?
Matthew MakYeah, so and what stopped you from not quitting? Yeah.
Scott DinanWhat stopped me is honestly my my family, man. You know, at that point I was so invested in the business. We had come a long way, and really it was just kind of like a mindset shift. It's like, look, I'm not the only one going through this. Every other company in this space in my market is going through the same thing. So between that and just my biggest why my family, I kept going.
Matthew MakYeah. And then like, was it that uh that was you like uh changing the dynamic of your mindset, saying, like like you said, you you got this far. I have my wife, got my kids. Like, I ain't letting go. I gotta keep going, right? There's no way, like I've gone too far, right?
Scott DinanYeah, I burned the bridges at that point, you know. I just quit my my W-2 um about a year prior to that, and I told myself I'm never going back to a W-2, you know. Yeah, I'm gonna work out my dream and not gonna work for someone else's dream.
Matthew MakSo yeah, and then what you're doing now is still related to what you were doing then.
Scott DinanExactly. Yeah, so yeah, I'm the founder of Trust First Management. We're a full service vacation rental management company in Florida. So, you know, we've managed about 50 properties, you know, 1500 plus five-star reviews. And um, yeah, man, we just manage real estate for people and uh an interesting business, you know, hospitality, but real estate at the same time. So yeah, it's uh it's fun.
Matthew MakYeah. So then, like, um, just uh uh understand for myself, so like let's say you know someone invests into a property too, they could even reach out to you and you can help uh manage the whole thing, right?
Scott DinanExactly. Remember service, we do everything from you know guest communication, maintenance, uh, you know, cleaning turnovers, taxes. We even remit taxes. Cool. So completely passive, yeah, for our clients.
Matthew MakSo have you had a lot of uh Canadian clients?
Scott DinanActually, yeah. Actually, I'm on boarding a Canadian right now from Toronto, and he's uh yeah, an amazing gentleman to work with. So I like you Canadian, you guys are nice people. So I I always enjoy working with you guys.
Matthew MakYeah, well, you're Americans are also nice too, man. So it just depends where you're on the states, right? Yeah, exactly. But I I I know from like because I'm also from Toronto, and I know that um the they call the Toronto people that go down there to pretty much retire is like the snowbirds, right?
Scott DinanA lot of those. That's where we make the most money is January to mid-April.
Matthew MakThat's when all you Canadians come down and T minus sometime, I'll be one of those. But not retirement, I mean like sooner, definitely way sooner. I need to keep my full energy like right now and come down there right now and enjoy every second of it. 100%. Awesome, awesome. Uh so now uh tell me um what does success actually look like in the trenches versus posting online or what people see outside of what you do? Yeah, um I would say really connecting at a deep level with my team. Yeah and you know, just to unpack that, right?
Scott DinanIt's like yes, we all start a business to make money and and find freedom and whatnot, but it's like once you actually start building a team, you realize there's so much more to it, right? Like you're responsible for these people at the end of the day. They get paychecks from you, they're feeding their family, right? Based on the decisions you make. So I think at a deep level, like when you're in the trenches, man, like being able to show up for your team and be in sync. We talk about this all the time in our on our team. You know, we all have to be links in a chain. And if there's one link that is not synced up, the entire thing falls apart.
Matthew MakOf course.
Scott DinanSo we really pride ourselves on just connecting, like we're very direct with each other. We have a lot of one-on-ones, team meetings, but we also know what drives everyone. And I've learned a lot of this from Dan Martell, which brought us together. You know, just understanding like how can I fit your dream inside of my dream? And correct for me, I think that's just a different level of success uh versus a lot of the stuff you see on social media.
Matthew MakYeah. And now um from learning that, and I totally agree with you, which is definitely for myself too and my team, um, speaking with them to seeing what their visions are versus how I can align with what mine are, right? So, like, yeah, it's definitely in a way a huge game changer. So now you've applied that. Have you seen now like um have you seen good stuff coming out of it? Like, I know it's everything stepping stones, right?
Scott DinanBut yeah, no, and it's been a night and day difference because I wasn't always that way, trust me. Um I like many, you have to learn the hard way. Yes, my style at first as a leader was not the best. It was very reactive, right? Um, it wasn't big picture, but ever since I made that switch, you know, I guess the best example is just to give you an actual example. You know, yesterday or actually two days ago, someone on my team just created an entire work order app using Cloud Code that's gonna transform our entire business. I didn't even really ask him to do it, he just came to me. He just did it, right? Yeah, because now he sees the vision, he sees that he could fit his dreams inside of mine. Yep, and that's just one example of many. So we're starting to see that stuff lab for sure.
Matthew MakCool. No, and that's great because it's like he took that initiative without you even asking, and that that shows you like how he's all he's full on board, right? It's the dream, which is which is awesome. Yeah, right now I'm kind of like the guy stuck doing all the AI stuff and learning, like I build whole software for my for my business and just trying to get everyone on board of it. Me is now trying to get it like you guys, come on, come on, yeah, take over, you know. There's always so much I could do.
Scott DinanYeah, I know. It's so easy to nerd out on that stuff and just oh yeah, do it yourself. But this is recent for me. Like the team just really like really, probably the past two weeks has just started like really getting into that, yeah.
Matthew MakYeah, the momentum.
Scott DinanYeah, yeah.
Matthew MakThere's there's a saying I I I've heard a lot in the past more recent years is that when you have that momentum, don't let it stop. Just you gotta keep going. Don't let the momentum stop. Yes. Right? You just keep running. Of course, man. Yeah, that's it. Now, uh what advice could you give most people in terms of uh if they wanted to start a business from scratch, but you know, it's holding them back. Yeah. Um there's many ways to start a business.
Scott DinanUh the way I started it, I I started it as a side hustle. And I think it comes down to your risk tolerance. Um like many, right? I was very, I guess, risk intolerant. Um, like you know, I'd worked my W-2 income into a very comfortable place. My wife, she also was, you know, bringing in some good income. So for me to have that confidence to really, you know, take the risk, like I decided, you know what, I'm just gonna put in the extra hours, whether that's before work, after work, maybe sometimes during work, right? Yeah, to build what eventually no one's hearing it right now.
Matthew MakYou're good, you're in your space. You don't look left, you don't look right, you know. That's the past.
Scott DinanAnd that's the beautiful thing, right?
Matthew MakYeah, sorry, continue.
Scott DinanJust yeah, no, you're good. So just taking that risk um with a little security cushion really helped me, you know, just take action. So I think if anyone's stuck, like, look, I I know so many personalities, and I think I'm guilty of this as well. Like it's so easy to overthink everything, right? Yeah, like before you even get started. So my piece of advice, don't be scared to have you know some security, whether that's Deb2 income or some other income. Um, but just take action, man. Like literally just do one thing at a time. Try to get 1% better every day.
Matthew MakYeah.
Scott DinanYeah, that'll compound uh a lot over a 12-month period.
Matthew MakYeah, of course. Yeah, no, and that's great, that's great advice, right? Like it, it's it, you're you're absolutely right about the it's the mindset, it's how you're thinking. We overcomplicate things in our subconscious, we let it overtake us, creating things that aren't real until we actually make it real.
Scott DinanYeah, and that's most of our reality. It's just like sitting in these thoughts that aren't even reality.
Matthew MakRight? Yeah, it's and then it's just like so many emotional factors come into play with that too. It's it's crazy. Yeah, I think technically human beings, we we are superheroes, but we just aren't even tapped into like even a fraction of what we're capable of doing, right?
Scott DinanI agree 100%. May have heard the recent podcast on Joe Rogan, Zach Bush. Okay, very interesting. You should read it or watch it, I should say. Yeah, but um, he talks about that. Um, I won't go into detail, but I agree 100%.
Matthew MakYeah. So who's your favorite superhero? Don't tell me Hulk.
Scott DinanNo, not Hulk. I'm a Batman guy. Yeah.
Matthew MakBatman guy? Oh, yeah. You like the DC.
Scott DinanYeah, I grew up, you know, I'm a 90s kid, so from from the jump, I had my Batman bike, my cape. I used to jump down the stairs thinking I could fly.
Matthew MakYeah.
Scott DinanYeah. Bruce Wayne for sure.
Matthew MakAwesome. Yeah. And you know, it's it's funny uh when you say about uh specifically Batman, right? Like I kind of felt like um in the same in the same way how you were working your you know your previous job, and then you were transitioning into what you're doing now, right? I was in the same same boat, right? Where um I was working in architecture and then started off with a couple machines with my business partner, and then like off to the side doing a few phone calls here and there. At the same time, I did tow trucking. I never told a lot of people this. Okay, but I was like working in office during the day. I was a tow trucker at night, and I felt like I was like that that uh not the billionaire guy, but like the idea of like at night I'm like someone else, and then during the day I'm someone else, you know, two different identities.
Scott DinanThat's a tough one.
Matthew MakAnd then three after.
Scott DinanYeah, tow trust. So you had people, I'm sure, confronting you, trying to fight you, or or most of the time they were just away from their vehicle.
Matthew MakYeah, I know, yeah. I it's not like nothing like the states, nothing like repo 911 or anything like that. So I I was it's a little bit more controlled uh up here, yeah, and nothing like that. No, yeah. I was good, but I'm not doing it anymore because yeah, I got family risk, I don't want to get hit by a car. You know, police aren't even safe either, right? Because even with the sirens, you never know. One guy just looks over on his phone or whatever, and boom, it's done. Takes a second, man. Yeah, that's the that's behind. So, Scott, tell us uh build without permission. What does it mean to you personally? To build without permission. Yeah. Well, um I think it's to have the freedom to be completely in charge of your future, right?
Scott DinanAnd especially now, right?
Matthew MakWe're living in a time of technology we've never had access to. Yeah. Right.
Scott DinanSo at the end of the day, why do you need permission? Like literally you can talk to your computer like a third grader and create anything.
Matthew MakYeah.
Scott DinanIt's literally insane. Like, I'm still trying to wrap my head around that. But to build without permission, I think really it's almost like a spiritual thing, right? Like, we are all creators within. We're we're we've been put on this earth to create.
Matthew MakYes.
Scott DinanSo at the end of the day, like permission, that is just a perception that we put into our our head. Yeah, it's not real. You don't need permission from anybody. If you have an idea, create it. And I think what gives people a lot of anxiety and depression, and you know, they just kind of live an unhappy life, is the gap between when they have that idea and when they actually implement it. And I think most people never actually take action and implement it.
Matthew MakYeah.
Scott DinanWe've met those people, those are people you meet in their 50s or 60s, and unfortunately, they're usually very bitter people.
Matthew MakRight.
Scott DinanBecause they feel their times passed and they need to be. They could have done more. Yeah, exactly. And you know, I I do think humanity as a whole, I think, is changing on that front. I think more people, you know, I think there's a um a lot of people think with the birth of AI, there's just gonna be a huge boom of people asking for less permission, right? Yes. Um, so I am optimistic, but uh yeah, that's what it means to me for sure.
Matthew MakCool. Yeah, no, for sure. And like yeah, build build without permission. Yeah, you don't need permission to do anything, right? And it it's interesting because uh we all uh growing up and how we were all raised, right? Was just like say from our parents, it's teaching us what they knew. Yeah, right. And then they were setting, let's say, boundaries from what's right and what's wrong in their eyes, which then kind of that's what triggered our brains to think that okay, you're you're putting that barrier there, right? Like that you're putting that wall that that's what's creating that I need permission to do this or I need permission to do that, and you know, until like you can realize it when you're flocking on your own, that how long does it take till you hit that point where you realize you don't need to listen to no one, right? But of obviously being respectful to everyone, but it's your life, yeah, it's no one else's. No one can tell you how to live your life, right?
Scott DinanAnd it's interesting because we're both dads, right?
Matthew MakYeah.
Scott DinanUm, and I catch myself, right? Because I mean you do it as a you see yourself programming your kids, right? Yeah, uh, because as a kid, right, you need permission to do to go outside, like, hey, can I go outside in the front yard and play? You know, you have to ask mom and dad first, right? Yes, yeah, and uh yeah, man, we're all just programmers, we're either you know programming ourselves or programming someone else.
Matthew MakYes. Oh yeah. All right, Scott. Now tell us where can we find you or where the audience can find you on IG, what platforms you have, a web page.
Scott DinanYeah.
Matthew MakTell us.
Scott DinanLook me up on Instagram. Um, it's at Scott.dynon, D-I-N-A-N. I try to keep it simple. Um, as far as you know, if anyone needs vacation rental management, um, our website is trustfirstmanagement.com. Um, I'm on LinkedIn as well, Scott Dinan, not as active there, and um working on being a more active on Instagram. So I think this will help for sure.
Matthew MakAbsolutely, dude. Just keep posting three minimum. It's gonna just get easier and easier. I'm just saying I got to the point where for myself, I start singing, dude. I don't know if you follow my personal yet, but I sing.
Scott DinanYeah, I love it. I love it, dude. And you're consistent, man.
Matthew MakThat's yeah, I try my best, you know. Yeah, that's how you do it. But I do, yeah, and then I do it honestly, like that that's my my stress reliever, but I do it to share the positivity, like for anyone else saying, like, freak, if I can do it, you can do it, and you shouldn't care what other people think, right? Because there's always gonna be haters out there, and the more haters you have, that means you're doing something right.
Scott DinanExactly. Haters gonna hate, as we said.
Matthew MakHaters gonna hate. That's it, man. Well, Scott, thanks for joining me on this. Um, but without permission, love to chat soon again. More than welcome to come on again in the future, too. I don't mind. And and let's stay connected. All right, man. Yes, so awesome. Have a great Friday, bro. Peace. See ya, brother. Ciao. If you're waiting for permission, you're already behind. The life you're building starts with the decisions you make today. So stop thinking and start moving. Subscribe, share this with someone still thinking about it, and start building something of your own. No blueprint, no approval, no excuses. I'm Matthew Mak. This is built without permission.