Collecting Keys - Real Estate Investing Podcast

How to SCALE an REI Business that Serves Your Lifestyle with Cole Ruud-Johnson

Episode 249 · · 44 min

Hosted by Mike DeHaan, Dan Austin, Dylan Koch · Guest: Cole Ruud-Johnson

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In this episode

Cole Ruud-Johnson joins Mike and Dan to explain how he moved from high-volume wholesaling to running call centers and consulting businesses that fund intentional real estate purchases. He walks through his hiring order, how he manages overseas talent, and the specific roles (executive assistant, chief of staff, house manager) that bought back his time. The conversation also covers why fixed overhead on variable revenue makes flipping and wholesaling fragile, and why he buys appreciation-focused assets in San Diego instead of chasing small cash flow.

Key takeaways

  • Cole treats his businesses as the cash generator and real estate as the place to protect that cash — he buys San Diego properties for appreciation and tax write-offs, and is fine if they only break even as long as they don't lose money.
  • Flipping and wholesaling companies carry fixed overhead (salespeople, office, debt) against fully variable, market-dependent revenue and no recurring income — a structural risk most small operators underestimate.
  • Start with a two-week time audit logged in 30-minute increments. Most people claiming ten-hour days are only moving the needle an hour or two.
  • His first hire is always admin, then fulfillment, marketing, sales, and finally leadership. A $5–7/hour global hire can remove roughly 70% of non-client-facing work.
  • Managing offshore talent matters more than finding elite talent: a Loom video, written step-by-step, a trigger, a definition of done, one live training, then weekly KPI check-ins instead of micromanaging screen time.
  • Solve communication first. His EA owns the inbox, calendar, bills, payroll, and travel; Cole only sees flagged items and uses privacy.com cards with spending limits to control financial access.

Show notes

How to SCALE an REI Business that serves your lifestyle with Cole Ruud-Johnson

Episode 249

Collecting Keys Podcast is starting the year strong by speaking to a true entrepreneur and real estate investor: Cole Ruud-Johnson. Through strategic investing, he has scaled multiple businesses and built an impressive portfolio at the age of 25.

In this episode, he shares his journey as a young entrepreneur and the profit and purpose ideology that informs his current business strategy. This leads into a discussion on the role systems and the value of leverage, from hiring employees to effective time management.

Cole also dives into issues with hustle culture, chasing cash flow, employee management and leadership. He then offers up actionable advice for scaling your real estate business while maintaining work-life balance and avoiding burnout — a common pitfall among entrepreneurs.

Tune in to this conversation with Cole to gain a ton of insights that will help you SCALE with intention!

Topics discussed in this episode:

Cole’s real estate background and business strategyBuilding systems and managing time to scale quicklyThe value of leverage for business growthAligning your personal goals with business strategyHiring and managing a global team of employeesCole’s goals for the futureConnect with Cole Ruud-Johnson:

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Frequently asked questions

What should be your first hire when scaling a real estate business?

Cole says an admin-level overseas hire at roughly $3–7 an hour, starting with your email inbox and calendar. He argues most people can offload about 70% of their non-client-facing work that way.

How do you manage an overseas VA so they actually perform?

Build a documented process for each task — a Loom video, written steps, a trigger for when to do it, and a definition of done — train them live once, then set clear measurables and review KPIs on a weekly call. Cole says micromanaging hours is what makes the relationship fail.

Why does Cole Ruud-Johnson avoid chasing cash flow?

He points out that a property making $500 a month can be in the red for the year after one repair. He prefers buying solid assets in supply-constrained markets like San Diego for appreciation, tax benefits, and later 1031 exchanges.

Scaling a Real Estate BusinessRentals & Cash FlowWholesaling

Transcript

Read the full transcript

Cole Ruud-Johnson: [0:00] That's why people end up burning out and hating what they do and are online complaining about entrepreneurship is because they they scale. They're doing $10,000,000 a year, but they have no idea why. Mhmm. And they have no time on their hands to do anything. Welcome

Speaker 2: [0:13] to collecting keys podcast. The show where you'll learn how to use real estate to create massive income, not just passive income. Real estate doesn't have to be a get rich slow game. Listen to the country's top real estate operators, and you'll have all the tools you need to replace your w two income and go beyond in under twelve months. Ready to take things to the next level? Let's jump in with our hosts, Mike DeHaan and Dan Austin for today's episode of the collecting keys podcast.

Mike DeHaan: [0:49] What is going on, guys? Today on the collecting keys real estate investing podcast, we have Colra Johnson, who is another very big operator in The United States and super, super show to have him on the show today. You know, we do all these interviews and very rarely do we get people that I think are like, I don't know, high level real estate operators. Right? You see, you get a ton of people that have like their niche businesses in their markets, which is cool. But for us as people that are also trying to grow like a larger business, getting the opportunity to meet with guys like Cole is honestly kind of why we started this podcast. You know, to be able to sit down and have a conversation with him for like an hour and talking about everything from, you know, real estate itself to business systems to kind of the mindset around business and everything else is super, super valuable. He covered a ton of great stuff in this episode.

Dan Austin: [1:41] Yeah. He's already 25 and I think we've had guys who are 65 or people at least double his age that haven't dropped as much wisdom. So he's done a lot and he's a true operator and selfishly, like you said, these are the kind of people we like being around because we get to ask them the questions we're curious about. He talks a lot about how to use leverage, which is not a dirty word, and then how to leverage people and how to leverage time so you can actually scale a real business and not have to sit there and be a hustler your whole real estate career.

Mike DeHaan: [2:08] Yeah. I mean, is such a huge part that so many people struggle with when they start getting into real estate investing business, is you have these cash flow problems. You know, you have like the variability in revenue, but your costs kind of stay the same. We kind of dive into all that sort of stuff, how to address it, how to view it, how to mentally deal with it. And overall, she was just a really, really valuable conversation around being an entrepreneur, not only in the real estate space, but just like in any sort of business that you decide to get into. So definitely give him a follow on all of his socials, guys. He's a very, very good person to follow. His podcast is also awesome, especially if you were trying to be a serious real estate investor. So go and subscribe to him over there too. And, you know, don't be afraid to reach out to him. People come on these shows because they want exposure. They want you to engage with them. So, you know, shoot him a DM, check out his show, send him an email. His assistant will probably let it gets back to you, but that's okay. That's how it has it set up. So Basically him. Yeah. Basically him. As far as he was saying at the end of this one. So anyways, guys, we appreciate you all.

Mike DeHaan: [3:07] Please leave us a five star review and share this with anyone who might find this show helpful. And enjoy this episode with Cole, guys. It's a great one. See y'all. Alright. Cole, I'm super excited to have you on the show, man. You are someone that I've been really excited to have on for a while because you were, I would say, like, the young guy that was getting after it when I first started getting into real estate. Uh-huh. And now you're still the young guy, and you're still getting after it. But you have grown such an incredible amount, so I'm super excited to dive into this conversation with you today. And I'm excited too because we're gonna have some good business talk in this conversation, which is, know, what it's all about at the end of the day once you've sort of reached that general real estate knowledge. So Cole, for people who don't know you, maybe give like a brief little introduction, who you are, what you do. I know there's a ton of long form content from you out there, so you can just give us like the short version.

Cole Ruud-Johnson: [3:58] Yeah yeah yeah, absolutely. Well first off, thanks for having me on guys. Hey man. Happy to be here, looking forward to it. I thought you were about to segue into me being old now. Having my first farm, now he's the old guy. Yeah. I played pickleball last night, woke up to some swollen knees and stuff, I'm like, man, 25, 26 does not feel like 20. But yeah, my background, I come in from a real estate family, of realtors, not investors. My great grandma was a realtor, my grandma was a realtor, my mom was a realtor, my brother's a realtor. And so I grew up, you know, when I wanted to make some extra change, I was helping my mom stage homes on the weekend, or taking the U Wall with my dad to pick up stores, you know, equipment for staging houses, things of that nature. And so the older I got into high school, every day I'd sit in class and go, I just wanna figure out a way to make my own money. That made me literally sick to my stomach for whatever reason, I don't know if I was born that way or something happened, but I made me sick to my stomach to think of working for someone else. And I've, so I've never had a job. When I first needed to make money coming out of kind of end of high school, I would coach basketball, or I'd do my own trainings and invite a bunch of kids and charge their parents $50 in a lesson or whatever.

Cole Ruud-Johnson: [5:08] And so fast forward into college, there was one Tuesday I drove home and like, screw it, I'm headed home. So I dropped out my sophomore year and I had done running start. So I had a couple years already done. I was like, I can go back if I need to take a couple years here and dive into this. And that led into me being a real estate agent. My whole family was realtors, and I said, man, I wanna make money. Right? I wanna I want the BMW, I wanna be able to go have coffees three times a day, and I wanna be that's the realtor life. Right? So I had my license from the summer before, and I started doing open houses and showings, and quickly realized that you don't get rich all of sudden from being just because you have your real estate license, especially when you're 19 and you live in Seattle. And so then finally, I'm kinda I'm going through this quickly because this I wanna get to the important part. I hung my license at a brokerage called Caliber who did a lot of auction stuff. They So were all doing the they were going to the auction, they were having Thursday night investor meetings at their office, collecting checks, going to the auction the next day for their clients, and bidding on auction properties, and making assignment fees. And I'm like, man, that's an interesting business. And I think I've always been you know, predispositioned towards business more than real estate.

Cole Ruud-Johnson: [6:08] So was a good kind of combo. And that led me down the path of wholesaling, which is what my primary thing I did for a couple years. And obviously, that's led to a bunch of different companies, which I'm excited to talk about those with you guys well today. But that's my background. It was it was a pretty simple I had to make money. I was probably the worst realtor of all time. I just didn't like it. So I I went the whole selling off market route and found found that game and and that has led in door after door after door after door for the past, you know, six, seven years.

Mike DeHaan: [6:38] Yeah. You know, it's such a simple sort of origin story, right? But I think that that's mostly where a lot of people come from, people just like to add an extra drama to me. No. That that's cool though, man. So now I guess fast forward, you know, you have done a ton of stuff the past couple years. You had a very successful wholesale operation. That's where I first got interested introduced to you years ago. Think maybe when you're on bigger pockets or or one of those. What are all your businesses look like now? Because I know we talked right before the show, business is now your main focus.

Cole Ruud-Johnson: [7:06] Yeah. So my real estate business in of itself, for years and years and years, we do a couple million dollars a year in revenue, but there was no like true. The more I realized, and I grow in business, you have to have like a clear what and why. I didn't really have that. I was just doing it to pay the bills, to make money, to make ten, twenty, thirty, forty grand a month, and to live the life I wanted to live, which is awesome. But as I've gotten into it more intensely, I've started thinking about how do I use the real estate business as more of a very tactical place to to build something meaningful. So business of my other companies, like I I own a couple big call centers, and we also do some consulting. And those are, for the most part, to me, more scalable companies. And so what they do is they feed my real estate side now. Right. And so I don't just wholesale to wholesale, I don't just do deals to do deals. It's very intentional now. This helipad's still running, but it's very intentional. If we're gonna do a deal, there's a purpose to it. It's not just to make a check. Yeah. Because in all my other businesses are surrounding real estate, it's just the real estate company itself, and that's what I teach a lot is, you have to have an intention to it, otherwise you're just gonna always be on a hamster wheel, which is dangerous, because I've seen that happen to so many people, they flip houses their whole life, they get to 50, 60 years old, and they realize, crap, I made a ton of money, but I have no idea where that money is. Mhmm, yep. Because there's no intention behind their business. And I think to a lot of people, they just scale to scale.

Cole Ruud-Johnson: [8:26] And to me, scale means profit and purpose. Like, scale means how can I make more money, and what am I gonna do with that money? So I can build a machine. And my whole thing, the whole other thing I teach is how do we build machines that run themselves, and machines that build machines. And especially if you're listening to this, how do you build a machine that buys real estate, or wholesales real estate, flips real estate, rather than you being the person wearing all seven, eight hats, doing all the work. So I have a call center, we service real estate investors also, a bunch of different people in different industries, it's grown big time. Our headquarters in Belize now, which is a couple hour flight from LA, couple hour flight from New York, Central Time Zone, English first country. And then we have a couple consulting businesses, and then the real estate stuff, so yeah. I like what you're

Dan Austin: [9:09] saying there, so you have these other businesses that are real estate adjacent, but that's what's feeding your investment strategy, is that kinda what I'm hearing? Yeah. So you're creating the income, that you, which is your purpose to invest that money and let that machine keep growing over there as well.

Cole Ruud-Johnson: [9:23] Yeah, every person I met that's extremely wealthy, has figured out how to play that big game of business and growing actual businesses, even if it's a real estate business, and then protecting that wealth, and compounding that wealth in in real estate. Mhmm. So that's my what, what, and why now. It's generate as much cash as possible through my companies, and then strategically invest that into real estate, and do deals that have long term purpose, not just to make $10.20, $30, which is awesome. You can make a lot of money wholesaling, a lot of money flipping. I think it's an incredible business. But for me, I'm just trying to be more strategic now with the purpose behind each deal that I do. Yeah. I mean, you know, I

Mike DeHaan: [10:01] think that's something that so many new people in entrepreneurship, more like I'd say like, most people they start with a financial freedom movement, and then entrepreneurship kinda comes around after that. Yep. But they don't realize that in order to make passive money, you have to be making, like, real money. You have to have the vertical income as well. So I love kind of that transition that you went through. And, you know, a lot of people, they tend to find that through real estate, through wholesaling, through flipping houses, whatever that is, and you're completely right. People don't have like a sort of strategy. So when you're saying you're doing it with intention now, are you still wholesaling businesses with your your helipad company, or are you literally just doing that as like a private marketing machine for your own deals now, and you're using these other companies to buy those investments?

Cole Ruud-Johnson: [10:45] Yeah, we do deals when they come our way. So we're still doing deals. I guess my point is we're just not like, I have no intention of doing deals just to do deals. So we still do deals, but it's not my main my main focus is just running up wholesale deals. So yes, it's much more of a tactical machine to build what I wanna build. And I think the best combination, especially in the tax strategy, is to make a bunch of money, whether that's flipping, wholesaling, doing other businesses, and then protecting that in real estate. Like, that's how a lot of the wealthiest people in our country operate. So I think that's more of my angle now. It's less about like, hey, let's go do 200 assignment deals in the next year. It's more about, okay, yeah, we'll do the deals that come to us that make sense. Because obviously, like, I'm I'm for profit. If a deal comes to our across our plate, $50,000 wholesale deal, we're gonna do it. How do we focus our team on the real estate side on some stuff that actually moves the needle for myself? Because a lot of people, I think that they forget they're building you're either building a life around your business, or you're either building your life to serve your business, or your business to serve your life. And I asked myself that question a year ago, I'm like, I was more self building my life to serve my business.

Cole Ruud-Johnson: [11:53] And I think that's why people end up burning out and hating what they do, and are online complaining about entrepreneurship, is because they scale, they're doing $10,000,000 a year, but they have no idea why, and they have no time on

Dan Austin: [12:03] their hands to do anything. I resonate with that a ton. Like Mike and I have like really been beating this drum recently, because like the idea Mike mentioned earlier is like making massive income, but the idea is is making massive income, and then investing that in real estate and the whole idea of building a real estate business and just collecting cash flow, like that is a freaking struggle. Yep. So learn how to make real money and then like you're saying, I love the way you're phrasing that, it's like protect it with real estate. It's awesome.

Mike DeHaan: [12:30] Yeah. Yeah. I was at a meetup with Aaron Imuch Steggy about a month ago in Austin and he opened the meetup with the line that real estate is not the thing. Real estate is the thing that gets you to the thing. Mhmm. And that really resonated with me as just like a that's like the grown up view Right. About what real estate investing can do for you. Right? So when you say you're strategically looking for your own assets now, what does that look like, I guess, mentality wise since you have these cash flowing machines with your other businesses? Are you still investing for cash flow? Are you looking for, like, equity spreads? Is it purely for tax benefits? Is that are you looking like residential or, you know, commercial stuff? Like, what's all that look like?

Cole Ruud-Johnson: [13:09] Yeah. So I'm a guy like and I kinda told you guys pretty sure, like I I like business a lot more than I like real estate. So a lot of what I do is purely like protection. So a lot of what my hello pad does now, we're looking at just like really solid assets in markets like San Diego where I live now. That, you know, you're not gonna get a crazy return. You're not gonna get an insane amount of cash flow. You're not gonna get I mean, you're not we're not flipping it for a $100,000. What can we buy that we know San Diego is an appreciation monster. What can we buy that we at least make a little bit of money on that's an appreciation monster that gets us tax write offs and is in is in a safe, secure market? Because San Diego is one of those markets you can't go north because you have the military base. You can't really go east because you have mountains and a bunch of desert. You can't go south because you're Mexico. So you're really kinda cornered, and you get just a massive appreciation. That's my thing is is how do we buy assets that are have equity built in, have a little bit of a value add component if we want to sell them or whatever, and play that game on the real estate side. On a business side, make as much cash there to do that.

Cole Ruud-Johnson: [14:12] That's more my thing now. Like, I'm not really a big cash flow guy. Like, I've owned portfolio of duplexes around the country. I've I've tried the in your backyard model. I've tried the around the country model. Yeah. And I know it works for people, but it's always anytime you see someone online saying, oh, we're making $500 a month in this house, I go, yeah, but one thing breaks Mhmm. And you're in the red for the year. Right? Like, it's not as attractive of business. And I think the real estate business, especially scaling a flipping company, development company, people don't realize you have fixed overhead and variable revenue, right? You don't have any recurring revenue. It's everything's variable on the revenue side. And so you're locking in salespeople, and you're locking in an office, and you're locking in debt. You're locking in a bunch of stuff that's fixed expenses on variable revenue, and revenue that's very dependent on the market. And I'm not like a negative anti realist, like I love real estate, it's what made me who I am. It's more of just cautioning people as they're building their company, why they're building it, and what they're building. Because I think you can wholesale and flip houses your way to an amazing income. But eventually, if you don't start focusing on building a business and an organization, it won't last long. Either you'll burn out or you'll get a golden optics syndrome, you'll chase the next best best thing to put online.

Cole Ruud-Johnson: [15:22] And so I know it's a bit of a tangent, but for me, my strategy is is buy buy assets you know are not gonna go anywhere, you know are gonna appreciate, you know are gonna give you some tax write offs, and let that be that. And if they don't make money, that's fine, as long as they don't lose money. And for me, that's my for right now, and that constantly changes, but for me right now, that's how I think about it.

Dan Austin: [15:41] Yeah. That's a great realistic view. Like, I don't think it's a bad view at all, think it's just facing reality. And you're saying you're not doing deals just to do deals, which is what we get caught up into this rat race, like you're saying, if you're a flipper, like, you're just flipping to flip at some point, because you have an arbitrary goal, or you have to pay your fixed overhead, your cruise, and all that sort of stuff. And Mike and I are trying to be like this too in real estate, just be more opportunistic with the opportunities in front of you, and use what you have, your massive income, or your income for your business, to take advantage of longer term plays in real estate. It seems to be, like Mike said earlier, the mature way to look at it, and I think what you're saying, it's a really realistic point of view.

Cole Ruud-Johnson: [16:18] Yeah, mean, look at San Diego, the median home price, just for a single family, is about a million bucks. So I go, hey, if I buy five homes in the next five years, in good areas that are million ish bucks, okay, they they may just break even. In ten years in San Diego, those are probably going to double in value. So that's in the next ten years, I'm gonna have $5,000,000 in appreciation. And a lot of times it'll a lot quicker. And that's the game. It's it's to buy solid assets, let them appreciate, and then ten thirty one into, to whoever wanted ten thirty one into duplexes, four plexes, and go bigger and play bigger vein. That's awesome. And I can use my machine, my mark, the machine I know how to do, which is source deals to go find those assets. Mhmm. I look at some of the most wealthy guys I know. A lot of people don't do this either, but really taking advantage too of the two year, if you're married, right, every two years, you trade your primary residence, you get a $500,000 tax free in San Diego. You get a little bit of value add, you're doing that every single two years, and, you know, you do that for ten years, and you have a, you know, you have a couple million dollars just tax free income that way, not income, but tax free equity that way. So that's the thing I think about. It's a lot more simple than people think.

Cole Ruud-Johnson: [17:22] Like, they don't have to do a million deals to live the life they wanna live, and that's why I think it screws people over, is because then they get on a hamster wheel and they start building their expenses and building their overhead. Most of the time, they don't need to to hit their goals. Mhmm.

Mike DeHaan: [17:35] Yeah. Yeah. So that, you know, what you mentioned there about the the fixed expenses with the variable income is such a misunderstood thing by, I would say, like, smaller investment companies. And, you know, with our coaching program, people ask us all the time. Fact, someone asked us this on our coaching call yesterday. It's like, how do you guys manage the cash flow situation with this? Because, you know, if you like to have a lot of money coming out, closings get delayed, deals aren't as big as you expect, all of sudden, you're in a cash crunch, and that's pretty much unavoidable. Right? Because you can determine what your average cost per deal is gonna be, but you don't know if that deal is gonna be, you know, a $10,000 fee or a $100,000 fee. Like, it can literally vary that much with the same cost. So let's transition over to, like, the system side and the business side of what you're talking about. And for someone that's kind of stuck in that hamster wheel, right, or trying to like figure out how to solve that, what are like some of the main systems that they could put in place to overcome that do you think?

Cole Ruud-Johnson: [18:30] Systems wise, if you're like you're on a hamster wheel, really the first thing you need to understand is what you're doing with your time. That's that's where I start. And so there's an exercise that I anyone I work with or anyone I talk to or people on my team, like our like our mid management team, our leaders in our companies, it's the same strategy I have them do, which is the time audit. So they spend two weeks and they document their day in thirty minute increments for two weeks. That's And a good place to start. Because then you really gotta see like, where is my time going? And for most people, even if they say they're working ten hours a day, they're probably only really working and moving the needle forward an hour, hour and a half, two hours a day. And I see that time and time again. And so first, understanding the first thing of leverage, which is time, where your time is going. And then the next thing that I always focus on is based on that, is how we can start buying back our time. Like, don't think people need to go in and grab a super fancy CRM or anything like that. I think the first systems, like, baseline foundational thing you can do after understanding your time is hiring global talent. Because people, even if you're making $50.60, $70,000 a year, you can afford to start hiring someone for $3.04, $5 an hour that can come in and take all the admin work off your plate. Because most people aren't really struggling. Yeah.

Cole Ruud-Johnson: [19:35] They have a lack of systems. You can also automate a lot of things, but a lot of people are struggling with burnout and exhaustion, and they feel like they don't have time because they're they're spending so much time doing admin things they just don't need to be doing. Like you guys said pre show, right, after a show, you have a team that cuts up your show. I'm Yeah. Guessing distributed across social media, and that's a that's a process. But really what that is, it's it's a it's a hire. Most people can get rid of 70% of what they do right now, especially as non non client, non human facing with $1.05, $67 an hour higher. That's the first place I like having people start. That really opens their brain to the business and delegation. And systems are easy to put in. Right? You buy CRM, you do a couple little tweaks, but that's really where I like to start. Because then you build that muscle, and then you start solving problems and ask yourself who, not how can I do it myself? That's the biggest differentiator between a hustler and an operator is it goes from you solving every problem to you asking who can solve this problem for me. Because most problems, you go on upwork.com, whatever you're facing, if you have an issue with your website, you can spend eight hours trying to learn WordPress, or you can hire someone for a $100 contract to step in and fix that whole issue.

Cole Ruud-Johnson: [20:43] And I think that's the biggest thing people have to have that mental switch to, because you can't really hustle yourself. Most people can't hustle their way to the business they wanna build. You have to learn how to get more leverage, and

Dan Austin: [20:54] that usually starts with people. Yes, it does.

Mike DeHaan: [20:56] Yeah. It's funny. That's always such a challenging thing for people to understand. I don't know if it's like limiting beliefs, if it's like fear of commitment to this other person, like what that is, I

Cole Ruud-Johnson: [21:06] don't know. I think that piece is is mostly where we live in a culture where everything's promoted, grind, hard work, ten hour days, and you can get to a good income that way, but you can get wealthy that way. Like, you can't beat your head against the wall to a $5,000,000 a year business. You have to eventually learn leverage. Learning how to hire, learning how to systemize, learning how to delegate, and learning how to actually lead and own an organization. And that's why people because they start doing that, they go, man, well, don't have a million things to work on today. And that's the biggest thing I see people fail with, is they can afford to hire, they can afford to do all these things, they just don't because they're addicted to that dopamine of completing that next task, to doing the same work they've done every single day for ten years. And I think that's the biggest thing. It's not that they're doing anything wrong, they just haven't flexed that muscle at all and built that muscle because it is a muscle you have to build. And so they're forever caught in this game of how can I do as many tasks as humanly possible? Because that's how they get their self worth is how much they did, and they don't have any leverage.

Dan Austin: [22:08] Yeah, man. That's tough too to overcome. Like I'm one of those people that I've historically been like super task oriented, right? Like, can I'm gonna just keep piling shit on and keep doing more and more. Yeah. That doesn't give you a lot of time to do the real stuff, like the strategy thinking and really giving your brain the break, so that all the creativity shit can pop in your head. That's why they say like when you're taking a shower or you're doing something where you can't do anything else but that, is when your most creative ideas come, because you're finally giving your brain that time to like, oh, okay, I like thinking about that.

Cole Ruud-Johnson: [22:38] Yep, 100%. It's true for me. Like I have a business coach, he was a Nighthawk pilot for the Navy SEALs. And he tells me every single week, he has to remind me, he's like, honestly, your highest and best use of your time is when you're on the golf course, you're in the hot tub, and your brain's turned off of, like, intense focus, and it's thinking through issues. Right. Because when you truly own a business, that's your ultimate job. Like Bezos says too, it's right. His executive team, the leaders in his company, their job is to make a couple good decisions per day. That's the rule. And I think I've struggled with that for a long time. People really struggle with that of our identities are so tied to how many hours you sit behind a computer, you stop forgetting that like, yeah, I mean, if you're on a walk, you might have one idea or one thing that if you implement will 10x your business, that you're not gonna get if you're responding to emails all day. But I think we just have a because of the school system, because of I have a lot of thoughts about that. Because of how we're raised, so task oriented, it twists around leverage. Then most people never learn leverage, or they feel bad about using leverage. Mhmm.

Cole Ruud-Johnson: [23:40] And it's a vicious cycle.

Mike DeHaan: [23:42] Yeah. I think the feeling bad about using leverage is a big one, especially because so many people, they dislike their w twos, their current life situation, that they feel like a sense of guilt trying to like have someone come in to what they view as the same situation.

Dan Austin: [23:55] I've had people tell me that the word leverage is not a nice word. It's like, are you kidding me? Like, that's an amazing word, like the idea of leveraging time, leveraging other people, like, that is awesome.

Cole Ruud-Johnson: [24:05] Yeah, get, whenever I post on my call center, I get so much hate, oh, you're paying people $5 an hour, I'm like, yeah, but you go to these countries, and I've been to Belize, I've been to our centers down there, and people are thrilled to have because that's the top of the pyramid employment in their country. Jobs are not a bad thing, and I feel like most people should have jobs because everything we're talking about is awesome, but most human beings are not capable of containing the amount of stress and things that go wrong to own a business. Because business on paper is simple. Writing down our plan to buy assets is simple. It's the day in, day out, and like, it's between the ears part, That's the difficult part. If you don't truly love it, if you're not truly wired internally to, and a part of you like that, you probably should have a job. That's the train I'm I'm on more and more. I think when the market was hot, everyone became a sexy real estate investor. And the reality is, like, there's nothing wrong with having a job Mhmm. Because a lot of people have great experiences with that, and build a lot of wealth while having a job.

Mike DeHaan: [25:00] Yeah. Truly underrated comment right there, honestly. And and there's this I think that's also part of the hustle culture is people are driven towards wanting to make something of themselves. And most people don't even know that they aren't cut out for it. Yeah. Honestly, where you see it a ton is when people, you know, have like marriages and there's one person that has an entrepreneurial drive and wants to, you know, pursue that, and then they have a spouse that is not fully aligned. And, you know, we all know guys and girls who have these entrepreneurial spirits and they always have this same question like, how do I get my spouse on Like they're not willing to take the risk off, not willing to commit to these things. Like, they're not the same mindset and they're not gonna be able to convince them. Like they just don't have the natural bug. Right?

Cole Ruud-Johnson: [25:42] Yeah. A lot of it's just built in, I feel like, in reality. So yeah, I mean, I think and a lot people have spouses too that do support them, but this is another game I think people get caught up in. And something I've been preaching about a lot is like the working ten hour a day, like, the difference to most people if they end up being worth 15,000,000, 20,000,000 is not that significant. And I have a business coach of mine who had an engagement when he was in his twenties, and he came home one day, and and after he just sold his company for tens of millions, and his fiance put the ring on the counter, was like, I'm done. And she told him, she's like, it's awesome what you're doing, but I never asked for any of it. And so I think too, like people that are building companies, the reason they burn out when they're in the office twelve hours a day, put all this pressure on themselves to make an extra $100 a year, to make an extra $10,000,000. I get that end the day, that's a hustle culture thing. A lot of people, you know what asked you to do that? And I think really finding and being okay with what your tolerance for stress because I'm really passionate about this now because I had a buddy recently who decided it was too much.

Cole Ruud-Johnson: [26:44] He had so much pressure on himself, so much stress on himself. He decided like, I'm better off not being here. And a lot of people get dig themselves in a hole with personally guaranteed debt and with stress and payroll, without even understanding why they're doing that, or if they wanna be doing that, just because that's what society deems, it's cool.

Dan Austin: [27:01] So yeah. That's super valuable what you're saying there too, and talking just about the alignment, and nobody asking you. We had a really good conversation yesterday for like, probably an hour and half with some GoBundance guys talking about like, your vision and getting super clear with that, but then aligning that vision to like, what is your spouse, what are your kids, like, what is your family vision? Because you could be caught up in that situation where you're like, I'm doing it for you guys. It's like, are you? Because nobody asked you to do it. Now you're just like burning the candle wick at both ends because some ego thing.

Cole Ruud-Johnson: [27:30] You're just an asshole. Yeah, It's an ego thing. Right? And I asked myself, like, what does my wife truly want? And she grew up with a with a dad who's in business, so she wants she likes that life. Right? She wants I mean, she's okay with that. But it's still like, do they really care if there's like an extra $20 left over within a month if we don't need it? No. Most like, they really don't. Obviously, there's you still wanna have financial security, and I'm very pro money, very pro capitalism. Like, I'm all about make as much money as you can and provide as many jobs as you can. But I think the game, many people are hurting so bad, especially right now with the way the market's turning. Mhmm. Because they're playing a game they don't wanna be playing just because they think other people care, or want them to be playing that game. Mhmm.

Mike DeHaan: [28:07] Absolutely. That's awesome. So going back to that overseas talent, which I think is you know, a huge piece that a lot of people need to work to their business. I'm not gonna ask like how to get started finding that because you know, anyone can go post on Upwork or onlinejobs.ph or whatever.

Cole Ruud-Johnson: [28:21] Yeah. I have YouTube videos too that are like hours long.

Mike DeHaan: [28:24] I'm like

Cole Ruud-Johnson: [28:25] by step of that.

Mike DeHaan: [28:26] Yeah. They're all over the place, right? What would you say to that for people who wanna find the best talent? And like the best overseas talent, like what what kind of people, what kind

Cole Ruud-Johnson: [28:34] of roles? I don't think people are gonna be worried about the best talent, I think you need be worried about how to manage. Right? Because that's what's not taught. You can find YouTube videos on, like, hiring, but then it's really the management side. And so I teach really, you know, a three or four step process to managing any overseas talent and making them good. Because with AI tools that are out there, you can take someone that can barely speak English in The Philippines, and they can be a really good asset to your team. So the first thing we do is we're just very clear on, like, what we want them to do. And what I mean by that is we don't just say, hey, I want you to do x y z. We build a process for them to do it. That usually consists of a Loom video, a step by step instruction on how to do that task, a trigger, and a definition of done, and training them on it one time lives. That's the second piece, actually being clear into your documentation of what that task is. How do they know when they should do it? How do they know it's done? And the next thing is how they report to you and how you measure against what you're setting for them. So a lot of people make the mistake as they micromanage. Every single day, they're worried about every single hour they're paying and doing the job. I think that's a terrible way to go about it to make your life miserable. So what I tell people is set really clearly defined measurables, and make sure you understand what success looks like, and then communicate that to them. And then have your call once a week with them, and have your KPIs so you can track what they're doing, and measure against whatever you you said success looks like.

Cole Ruud-Johnson: [29:47] Cause I see so many people, they go and hire someone from The Philippines, they treat them like garbage, they treat them like they're subhuman just because they don't live in The United States, and they expect them to perform great, and they're slocking them every twenty minutes, making sure they're doing their work, like that doesn't work. What does work is setting a very clearly defined task, setting a very clear defined idea of what success looks like, communicating that, and then measuring against that on a weekly basis. That to me is what a good starting place is for managing someone. It's not as much about finding the best hire, it's how you manage that hire. Because if you can do that piece right, you don't have to find the perfect person. So true. That's like Yeah.

Dan Austin: [30:26] The leadership one zero one, right? Like set expectations, and then the one thing that people suck at is actually follow through on those expectations. Check-in with them, help them grow, help them meet those expectations.

Mike DeHaan: [30:36] Yeah. And I don't know what that is with like, you know, the people that treat the overseas, you know, VAs like garbage. I've seen that all like all the time. You know, I I've seen that from guys that I know are super well off that are will be posting things like, hey. So my VA, I've been tracking their time, watching their screen. They're only actually working thirty hours a week. Like, how do I get out of having to pay them for forty? Or like, is there anyone that wants them to do ten hours of work

Dan Austin: [31:00] to save $20?

Mike DeHaan: [31:01] Yeah. I'm like, you think fucking Sharon, your assistant that sits at your office works for forty hours a week? No. She works for twelve, but you pay her for forty.

Cole Ruud-Johnson: [31:09] Yeah. That's completely good. This shouldn't be business hours in my opinion.

Dan Austin: [31:12] That's Exactly. They shouldn't hire people.

Cole Ruud-Johnson: [31:14] Yeah. If you're taking the responsibility of hiring someone and taking ownership over their income, you have to know how to manage, otherwise you shouldn't be doing it, and that's that's my opinion on that, because it's said so common. Yeah. And I think that's number one thing that exposes people to me of like, okay, yeah, you just shouldn't you shouldn't own a business. That's just the reality of it.

Dan Austin: [31:31] Do you have like a key hire that you've hired? I'm thinking like on an executive assistant level, or somewhere that helps you kinda manage your day to day, because that's something Mike and I have talked about. Like, that to me sounds like a really nice thing to have.

Cole Ruud-Johnson: [31:44] Yeah. I made a I made a lot of aspires. So my biggest thing, every business I grow, I follow just a step by step. So I go, I hire for admin, then I hire fulfillment, then I hire marketing, then sales, and then leadership. Yeah. That's my just like set blueprint. But what I can say is, a couple key hires I made that have changed the game for me, not just in business, but personally, I have a personal chief of staff, and she's based in Toronto. She's salary, makes a good salary, and gets commission on the on the business. And what she is, I call her like the Swiss army knife. She jumps into any fire, any fire that's going on. She's like my clone of me. So she can handle any situation just like I could. She jumps in, or if we need a project completed, if we need to hire in a certain company, so she's like a bandwidth extender for each company and everything that I do. And I have a executive assistant, that's like email, calendar, inbox, bills, payroll, travel, all that kind of stuff. That's a life changing hire for people, because like, you shouldn't check your email more than once a day. Like, my biggest thing that changed the game for me, as an EA, $67 an hour. We have an email system, he has an inbox, I have an inbox. I only look at the stuff he puts in my inbox, and we flag on our bi daily review. I don't look at my email besides that, unless he flags something for me. So I respond to attorneys, I respond to my business partners, and I respond to like requests from people that I know, or through a connection, that's it.

Cole Ruud-Johnson: [33:01] And that's what most people they're spending an hour, two, three hours a day on email, you should be spending ten minutes max. Same thing for Slack, same thing for your calendar, same thing for travel and bills. Like you can get half your day back, most people can, paying someone $7 an hour. So I think those two things are big. And then the third one is kind of a luxury hire, but we hired a house manager, my wife and I, It was not even expensive. It costs like a grand a month. They come she comes three hours a day. It's laundry, dishes, cars are clean, groceries are ordered, like everything's done. And that to me is the most personal, like personal life impactful hire, because you have I mean, that that buys back a ton of time and bandwidth. And if you guys are married, I'm sure you can you can imagine what that what else that buys back in terms of just peace of mind. Right? Yeah. Those are the couple that I've that have really changed the game. I have a head of content too, who's full time, who just all of our media strategy and all of our runs our editors and our graphic design team and all that kind of stuff.

Mike DeHaan: [33:52] Nice. Yeah. We just brought in the head of content, which has been huge for us. I have a question about what that looked like bringing in your your EA. Because, you know, something that I've thought about for a while, and honestly, one of the most daunting things is, like, what does that handoff look like in terms of, like, all your accounts and your email and everything else? Because, like, my stuff's already, like, you know, it's a pile of spaghetti. All of a sudden I have to like just give it to somebody else and they figure out how to untangle it and have someone else take it over. Do you have any like tips or guidance for that?

Cole Ruud-Johnson: [34:20] Yeah, I mean I think it's just being okay with it being a mess for a while, honestly. Like it's gonna take time to unwind the knot we create for ourselves, but it's pretty pretty simple. It's like just I would start with the email inbox at the first place I would start. And I would just meet with them daily for the first two weeks for fifteen minutes in the morning, and help them understand your decision making process when it comes to your inbox, and set a clear defined process. If they're a business partner that has one of these names, if they're an attorney, if they're someone that introduces me via cc and email for a podcast opportunity or something like that, something I need to respond to, put it in my inbox, let me know on our on our meeting. Anything else, if it's I'm on a vacation and someone emails saying, hey Cole, can you come to my podcast? Hey Cole, can you have blah blah blah? You can just literally and they live in my inbox. So they also have their own email, they live in they live in my inbox. It's a big thing that changed the game for me. And they'll respond, they'll jump in from their email saying, hey, I'm just jumping on this because I'm sure you want a quick response. Here's what we can do with that situation, blah blah blah. That's it on the email side. I would start with email, and then I would move on to other communication platforms, and I would solve communication first. Because you gotta think, as entrepreneurs, you guys have run a podcast, you have different companies, you have so much communication coming in, and 99% of it don't need to take up bandwidth, because we all only have so much bandwidth.

Cole Ruud-Johnson: [35:35] So if you can solve communication, and make sure everything is getting filtered, and only the one percent of super important things are impacting your bandwidth, that's life changing alone in itself. Then I moved on to just, what else do I hate doing? I hate paying bills, like I don't even log into my personal bank account anymore. I don't like it. I don't like logging in. Everyone wakes up, usually log into the bank account, they make sure their bills are paid, their credit cards are paid, their travel's booked. Like, then I move through just things I don't like to do, which is, you know, my bills, my payroll for my companies, my credit cards, my all that stuff. And I just kept adding onto that. And then eventually, you kinda get out of that spot, and one by one, or two, three months, you don't have to worry about that stuff.

Mike DeHaan: [36:13] So do they act as you on your emails, or are they like basically working as your assistant?

Cole Ruud-Johnson: [36:17] Yeah, most of the time they'll man and monitor my inbox on one screen, but then if they need to jump in, they'll jump in on a different screen and through from their own email. But sometimes they'll jump in as me, or they'll sign stuff for me. It's something, it's a document I need to sign.

Dan Austin: [36:30] Yeah. Yeah. I was gonna ask you, like, did you feel comfortable with giving over bill paying financial information? Is this a offshore VA, onshore, not that that matters, but how did you overcome that kind of concern?

Cole Ruud-Johnson: [36:42] Yeah, so when it comes to bank account access, it's my chief of staff, and that just came through time trusting here, and I also have to, I started by two factor authentication, so I had to approve any wire, any transfer, any ACH, any ZO. Sure. And I just send you them out in my end to a text, but now I got rid of that, she does it all. It's just trust. I just, and it's a, there's obviously there's a risk there, right, but it's a trust thing. And I, you know, I check my bank once a week and I go through the weekly transactions and it's and I have a bookkeeper, so it's not like it weren't we're not watching it a little bit. And then on the on the other side with my EA and stuff for booking travel and everything, they have something called privacy card. It's like privacy.com, and it's a you can set a limit on that card, and it pulls right from your bank account. So I don't I don't give them like unlimited credit cards. So that's been a good option for like travel booking and things of that nature. They'll set a thousand dollar limit on that card, and then they can use it for travel and ordering things, stuff like that. That was valuable. Nice.

Mike DeHaan: [37:31] Yeah. That's super awesome. Cool. Well, you got a lot going on, Cole. It's awesome to see how you've sort of like grown to you in such a short period of time. So, I mean, you're only 25. What's what's next for you? What do you sort of plan for the rest of your twenties going into the rest of your life, which all of us now in 2023, what do they say, most of us will probably live to be over 100 with general stuff?

Cole Ruud-Johnson: [37:55] You got

Speaker 2: [37:56] a lot

Mike DeHaan: [37:56] of time to figure out whatever you want that to look like. So what's on your plan? What's on your docket?

Cole Ruud-Johnson: [38:00] Yeah. I think I want to stick with what I'm doing right now and just and just grow it as big as I can. I think there's a lot more opportunity and you can dig a lot deeper than you think you can in whatever opportunity you're chasing right now. Like with the podcast, for example, podcasts, podcasts themselves are sometimes $50,100,000,000 dollar companies. Definitely. Media companies, I think everyone has a responsibility if they're a business owner, to create a media company around themselves, and really turn them themselves into a brand. I mean, that's a massive opportunity, so continuing to grow the brand and presence across social media is a big thing for me. I think there's just between hiring, and business partners, and advisors, and mentors, and opportunities, it's just like, there's nothing like that. And it's a slow compounding game, but it's a very meaningful game. A lot of the hires we have in our companies, they didn't we were probably not at the point to hire someone of their skill, but they just said, hey, Kauai, see your stuff, I wanna work for you. And that's very valuable. Besides that, continuing to grow the companies we have, I wanna sell one of our companies in the next three three, four years, and I think we're on pace for that. That's a big thing for me. And just as like a I probably won't I never feel as good as it as you think it will when you get there. Right?

Cole Ruud-Johnson: [39:08] But something I wanna check off. And then, yeah, that's how continue to grow my companies, get better and better as a leader and entrepreneur. And I travel a lot. So continuing to do all that stuff as well. I like it.

Speaker 2: [39:21] There you go.

Mike DeHaan: [39:21] Just the end of the game, man. I love it. That's the best place to be.

Cole Ruud-Johnson: [39:24] Yeah. Awesome. Very cool.

Mike DeHaan: [39:26] Alright. Well, we are getting to the end of time here. So we're gonna go into our end of show questions. We ask the same three questions for every guest that comes on the show. And the first one is always the group favorite. And that is, what is your craziest real estate investing story? And this can be a big win, a big loss, crazy tenant, crazy seller

Cole Ruud-Johnson: [39:47] Yeah.

Mike DeHaan: [39:47] You know, crazy transaction, whatever you got.

Cole Ruud-Johnson: [39:49] I think my favorite one is when I was 20 years old, we just started doing text marketing, I think that was like 2019 when texting became huge. And we sent out a text like a couple weeks into starting it. And two days later, guy texts back and goes, yeah, meet me here, I'll sell you my house for $4.50. But this has gotta be fraud, This has gotta be a scam, someone trying to mess with us, I mean this house is worth like 900 as is. And so we went there and met with him, and he walked in, he was wearing probably a $200,000 watch, probably a 60 year old dude, and it was my old business partner and myself, and we're sort of standing there. And he walks up to us, says, I love seeing young guys make money, and young guys that are hustling make money. And he, we pull the contract, he signed it for $4.50, that was a $200,000 assignment fee. Two weeks later we got paid. And I was like, we probably could have made more on it too, but it was such a big number, we just jumped on it. Yeah, that really shook me up because I was like, man, that check right there, that's five years of the average salary in The US Yep. In two weeks because I sent a text message. My tagline in my podcast I always end with is you're one deal away, Because I think the most meaningful thing for people is you're one good deal away from something in your brain switching forever, and you understanding that you can like truly control your financial future and what happens around that. So that was part of my crazy steal story. Great story.

Mike DeHaan: [41:08] Yeah. That's awesome. Did you ever do any research on that guy? Whenever stuff like that happens, I'm always trying to figure out what illegal shit they're involved in.

Cole Ruud-Johnson: [41:15] Yeah. So he he was a massive apartment builder. He builds massive apartments all over the West Coast. And so he couple $100 didn't mean anything to him. He just went through a divorce, and he was like, you guys remind me of myself, wanna help you guys succeed, it was one of those things.

Mike DeHaan: [41:32] It's cool. Mhmm. Yeah. That was probably the house that his ex wife was gonna have some stake in. So he was like, I gotta offload this thing. She has to get shit.

Dan Austin: [41:40] He's like, exactly. I don't

Cole Ruud-Johnson: [41:42] want her to get shit.

Mike DeHaan: [41:43] Alright. Second question. What is the number one tip you would give to a small time operator trying to take their business to the next level?

Cole Ruud-Johnson: [41:50] Overseas talent, man. Make try to make that first hire, $5 an hour, get get swinging at it because that can change your life a lot quicker than you think, and you enjoy your business. And even if you still wanna wear a lot of the hats in your business, can get the very, your email, if you can get little things off your plate, you'll wake up and be able to spend your time what makes you the most money. I think that's what we all want, to make as much money as possible at the end of day. So that would be my number one tip.

Mike DeHaan: [42:14] Easy enough. Cool. Alright. And then last question, where can people find you, follow you, and reach

Cole Ruud-Johnson: [42:19] out to you? I'm on every platform. If you want more educational, like long form stuff, YouTube and in in my podcast, Off Market Operator. If you want to chat in the DMs or to see more short form stuff, Twitter, Instagram. I'm most responsive on Instagram DMs. That's at Cole Roojohnson on all lowercase, no underscore anything. And yeah. I'm pretty much on every platform.

Mike DeHaan: [42:39] Cool. I love it. Easy enough. Well, Cole, I really appreciate you coming on show, man. Super good to meet you, and I I love just the deep dives in entrepreneurship and and hearing everything else there. It's rare to meet people that are, like, just like true entrepreneurs and true business owners. So I really appreciate you taking time out of your schedule to come and chat with us for a little bit.

Cole Ruud-Johnson: [42:57] Likewise, guys. A lot of fun. Appreciate it. Awesome.

Mike DeHaan: [42:58] Cool. Well, thanks so much everybody for listening. You should definitely give Cole a follow and check out his podcast as well. It's a great show. And if you like what we talk about and some of the weeds that we get into, then you'll definitely love his show because he talks about a lot of similar stuff and at sometimes even a little bit of a higher level and just a different perspective. So, you know, check them out there and also follow him on the socials. Besides that, please go and leave us a five star review on iTunes and share this with anyone else who is interested in making massive income, not just passive income through a real estate business. And we appreciate you all. Talk to you guys next week.

Speaker 2: [43:32] Thanks for listening to collecting keys. Drop us a five star review on iTunes and send us a screenshot to mike@collectingkeys.com for your chance to receive a free collecting keys t shirt.

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