
Discover the power of clear mission statements and strategic real estate growth as we delve into an insightful conversation with Jimmy Vreeland, a former army member turned real estate maven. Jimmy shares his journey from building a rental portfolio to strategically pivoting into turnkey properties, wholesaling, and leveraging technology for business excellence. Don’t miss this episode for valuable insights on achieving growth through clear vision and effective strategies.
About Jimmy Vreeland

Jimmy Vreeland is a 2003 graduate from the United States Military Academy at West Point and Army Black Knight football alumni. After receiving his commission, he joined the force as an Army Field Artillery Officer where he would serve a deployment to Iraq in 2005 with the 3 rd Infantry Division. Subsequently becoming a US Army Ranger, he would deploy again to Iraq with the 2 nd Ranger Battalion as a Fire Support Officer in 2006 followed up by a tour to Afghanistan in 2007. Exiting the Army at the rank of Captain in 2008, Jimmy set out to make an impact in the private sector through sales. Obtaining his first post-military employment with Stryker Orthopedics, in less than 2 years he had become the highest grossing rep for the entire St. Louis branch and would hold that title for the next 6 years. In 2014, in an attempt to escape the corporate world, Jimmy formed Vreeland Capital, LLC. Eyeing a unique opportunity within the single family real estate market, Jimmy began purchasing distressed properties in the St. Louis area. Using a tried and tested formula, ensuring day 1 equity and foresight to focus on cash-flowing properties, Jimmy has secured over 100 properties for himself and another 700+houses for his turn key buyers. These houses have turned into a steady stream of income for investors and a safe and comfortable house for tenant-buyers. Vreeland Capital offers a one stop shop for investors because it runs subsidiary organizations that find, fix, flip, and then manage cash flowing rental properties. In 2018 in an effort to better educate his buyers and to document all the lessons learned from the military and escaping the rat race, Jimmy teamed up with Ryan Lee and Brad Gibb to form CashFLow Tactics. This education company empowers real estate investors to grow their wealth, learn the actual tactics of passive real estate investing, and stay up to date with the latest trends and lessons learned in the turn key real estate niche. Since then Vreeland Capital has expanded into a one stop shop for anyone looking to invest in St Louis. Jimmy’s team is able to acquire off market houses for investors, provide construction management, property management, and leasing services for any remote investor. Jimmy continues to reside in the St. Louis area with his wife and 4 kids as he pursues the expansion of Vreeland Capital and Cash Flow Tactics while helping others find a safe place to utilize their long term capital and create steady streams of passive income.
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Keep to the Mission – with Jimmy Vreeland
Hey, everybody’s Jordan Samuel Fleming here with another episode of That Real Estate Tech Guy and I am delighted that my co-pilot for today’s episode is Jimmy Vreeland from Vreeland Capital. Jimmy, thanks for joining us on the podcast. How would you give a little introduction to yourself and your business?
So Jordan, I run a turnkey wholesaling company out of St. Louis, Missouri. We’re about 50-50 wholesale and 50-50 turnkey. We manage over 600 units. And we have a real estate education platform called Cashflow Tactics, which helps us generate and educate our turnkey buyers.
Can you give us just a little history of how your real estate business has developed over the years?
I used to be in the army, and when I was in Iraq, I read “Rich Dad, Poor Dad,” and I’ve been buying rentals since 2005. I bought about two a year for 10 years, until 2015. In 2015, I learned how to raise private money. And so I got 60. So at that point, I had like 80 units, no team, no process, no system. A weekend side hustle turned into a low-paying part-time job in real estate. In 2017, luckily, I met my business partner, Cashflow Tactics, and they told me about turnkey and that investors were looking for fully occupied rentals. So in 2017, we kind of pivoted into turnkey. Then, in 2018, we sold over 100 turnkeys. 2019, we ran low on inventory. So we had to figure out how to do wholesaling and acquire for ourselves. Then, thank God, in 2020, 21, 2022, we have not added any business lines. We just keep trying to perfect our systems. In fact, our process but as far as the technology growth, we took a major step at the beginning of this year by converting the smrtPhone and converting to Salesforce for our wholesaling business.
So you guys jump to a system like Salesforce to manage the wholesaling business. That’s a phenomenal jump in terms of visibility and how you can track everything. Before Salesforce, you said you started out and really kind of grew just yourself. But before Salesforce, what were you using to manage things?
We use Rent Manager to do the property management business. We use Builder Trend for the construction part. And then we use Salesforce for wholesaling. And we still use Podio to kind of get construction and property management to talk to each other.
Okay, so you were on a Podio system. And you’ve got a bit of stuff there still, but now you’re inside Salesforce, and I presume that’s Left Main REI. Just in terms of how many people are on the real estate team right now?
Between everybody and VAs, 25 people?
When you start to scale a business with any amount of people, it’s pretty easy to do things when it’s just you and maybe another person. You can do things loose and see how it goes with that many people. Visibility, transparency, and tracking things are critical. So what has been the biggest sort of change as you’ve developed your system and you’ve grown as a staff, In terms of you as the owner? What have been your biggest takeaways?
Understanding the importance of coordinating action. I’m a student of a guy named Larry Yash. I used to be an Army Ranger. He was a Navy SEAL, but he has a full business coaching planning called SEAL Team Leaders. And he impressed me. Like everybody thinks, going, deploying, and being in a special forces team is like complete misery. But the phenomenon, which is my area of expertise, is that everybody on the team is having the time of their lives. And Larry pointed out to me that the reason I enjoyed the Ranger Regiment was because we were doing very difficult things in very bad environments. But we are coordinating our actions very well together. And that is fun. And so in the civilian world, in the small business world, if you’re not coordinating action together, I’ve had days like these businesses just feel like Groundhog Day. It’s like, you wake up, you put out fires, and you go to bed exhausted, you do it over. And then you hire employees, thinking you’re relieved. And it’s just harder because you’re not coordinating actions correctly. You’re adding complexity. The way it’s been described to me by Larry is that information inside your business is like blood. So instead of hiring a COO, which a lot of people do, or an integrator, if you’re familiar with CAOs, I hired a Coordination of Action Officer. And so that person’s job is to make sure the software systems are functioning correctly, that different parts of the business are communicating with each other, and that no one’s just working in a silo. Technology combined with someone dedicated to coordinating action is game-changing.
Over the course of the last 15, 20, and 30 years that I’ve been working with different companies. I’ve actually had the opportunity to work with a number of veteran-owned businesses. One of the things that I discovered is that, for the most part, people who have been on the ground, and working inside a military organization’s structure have a really great ability to deal with it. And their ability to not deal with structure is not so good. And so what you end up getting, if it goes well, is a group of people who say, Hey, we want to make this change. Everyone understood that. As long as everybody understood it, it was the easiest change you’d ever make. Because if they understand it, they just fly with it.
You’ve got to always have a mission statement. You’ve got to always have I went on—call it 200 missions, but by the time I was deployed, on every mission I went on, I had a mission statement, and I had the commander’s intent. And the theory is that freeborn Americans operating, knowing a mission and knowing the commander’s intent, if everybody on the mission were to die, that lone survivor can still operate because we’re gonna go get a little political here. If you have an army of dictators who can’t make decisions, they’re not free individuals. They can’t make decisions. So what I’ve had to bring into business is articulate a clear mission statement, and then we clear the desired end state, so that, let’s say everybody slept past their alarm, and the lowest person on our team is still working, they know what to do.
25 is a lot of people. So presumably for the wholesaling side, you’ve got dedicated teams for acquisitions, transaction coordination, dispo, etc. In terms of your operation, especially the guy who is in charge of making it all work, what were some of the key visibility points that the systems brought to them that they wouldn’t be able to do without them?
Dashboards, scoreboards, and dashboards. That was the main reason we switched to Salesforce is the ability to create dashboards and scoreboards. My team has three, or I’ve got 25. I think five are veterans, and many, if not most, of my team are also former athletes. So we don’t play games where we don’t keep score. And so keeping score and Google Sheets is tough. So I would say automation is very important, but reporting is where I find the most value.
As you’re scaling up, you start adding people. You add departments, you add processes, and you add systems. It all becomes a much more complex engine. If you found that the transition to Salesforce has also allowed you to do a more transparent and better kind of integration across your teams, is that something that’s been a focus as well?
I’d say the immediate effect has been felt in our follow-up process. My guys wake up, they open up their computer, and they know, we’ve done a good job of putting a very good follow-up process together. So they open up their computer, and they know who they have to follow up with that day, and it’s just automated. And then I was in corporate sales for eight years. If you keep your CRM of your hot customers and your follow-ups in your head, you will fail. And you can’t hold anybody accountable. What if you don’t have it in the CRM?
You said you had VA. There’s a lot of VA action at the start of the funnel from a lead acquisition, whether it’s cold calling or dealing with the unqualified. You said you use Salesforce and you use smrtPhone. One of the key benefits of having an integrated phone and CRM is that the recordings and everything else get logged in your CRM. Do you have a process internally for quality assurance, like making sure that the VAs are following the right methods in terms of how they’re speaking on the phone or how they’re talking?
Darren Damme really squared away our Salesforce. They helped us get up and running in 60 days. It was awesome. But we’re in the collective genius together. And so we have verbatim copied everything Brewer puts out, and Brewer teaches a great process where we hired a scoreboard VA whose part of their job is just a spot check of calls and then a scoring system on those calls. I work trying Steve Trang is putting out something where that automates. They’ve been talking about doing it for a while, but it is not ready for prime time yet, but that is where we’ll go eventually with it. Interesting. Interesting. Yeah, it’s funny. I had a conversation today with a company that wants to integrate with smrtPhone. That’s an artificial intelligence system that can listen to calls, identify themes, and deliver. The AI. Is that it? Anyway, that’s another reason we switched to smrtPhone. So as an owner, I just sleep well at night knowing that our calls are getting listened to.
And it's critical because I always think not enough people are actually spot-checking calls. So do they spot-tick every day or every week?
I would say a couple of times a week. It's not like every call gets listened to, but it's like your spot checks every week. We check everybody, regardless of VA or not, just because we're constantly trying to get better.
You're spot-checking and seeing where there may be things you can incremental improvements across everybody, essentially. You guys are working on your different marketing sources, and assessing what's working and what's not. If people are new to the game, they start spending serious money on marketing. How do you guys measure the different marketing spends that you make and how successful they are?
Our target for any dollar we spend on marketing is a four-to-one return. So that's another great part about Salesforce. We got the ROI calculator. So, if you're new and you're just about to get ready to do a big mail drop, I empathize with you. It sucks the first time you write that check the first time you do TV. So if we're not getting a four-to-one return, something is wrong, either with inbound or sales, or it's just a trigger for us to start examining what's going on. But also just have the expectation that sometimes mail has been as good as seven to one, sometimes it's only been three to one, but it's always averaging out at four to one. Jason Lewis teaches this, but have the expectation that you're going to have two legs that you stand on for marketing. Right now, for us, it's TV and mail. It used to be just text mail. So we fully expect things to go up and down seasonally. And we're just always keeping an eye on it. As long as it's around four to one, we'll keep spending. But if it starts dropping three to one, we're going to cut our spending. It's not “fire and forget.” It's something that has to be constantly monitored.
If you're starting out and you're terrified of writing that first check, as you say, you really don't want to part with that amount of money. You do have to give it a certain period of time to actually properly judge these things. It's not one of those things that you can usually say, I'm gonna write this check. And if it doesn't pay off in a week, it hasn't been successful. You've got to give it room to breathe.
All this mail. TV was a little faster, but mail took 90 days. We didn't get anything for 90 days. We're horrible at inbound leads, and we're not good at sales. But of course, the mail guy.
90 days would be nerve-wracking, particularly if you're spending money and thinking to yourselves, Oh my God, have I just wasted all this cash? How were you able to determine that it was the inbound process that was letting you down?
It was just a process, like not hitting 41. Okay, let's check the chain. What's our response rate? Okay, our response rate was .5 - was industry standard. What was our conversion to the appointment industry standard? What was our close rate? It was like 10%. Okay, the industry standard for closing is 25. Gotta sharpen your sales skills. And then we've had other minds closing where you just follow the chain. We've had other moments where, like, hey, our close rate is 30%, but we're not doing any more deals. What's up the chain? Where are we losing stuff?
Have you seen that as you grew with your CRM from you by yourself to you and a couple of other people to 25 people? Have you become more reliant on and more trusting in the fact that you've got good data?
Yes. And then that helps you sleep at night. I'm wondering, do you ever take the Colby test? It's a personality test that if you know how you'd like to solve problems, you got factfinder, which are people who are really detail-oriented, implementers, and quickstarts. And I'm forgetting the fourth one, but I'm like a 10-quickstart. So I like to solve problems by just running with my gut. And that's great to get snowballs rolling. But when you're trying to run a sophisticated business, it's bad. Because I have the tendency to be like, Something's wrong, I just must fire everyone. No, like, let's back up and say, What's wrong with the process? So you gotta have data to see if your process is working?
It's only when you start scaling a business that you really see the need for the process, the systems, the people, and the culture to meld together.
You're gonna hear a funny story about the process. It was probably 2019, we were at the point where we were really scaling, and then I was at the collective genius. Tendency homebuyer Jeremy Fish did a presentation and showed everybody his level of process and level of detail. I'm like a sales guy. I'm like a cowboy. I just like running off adrenaline. I used to hate systems and processes. My wife was there with me. I was like, I don't know if I want to do this. I don't know if I want to get that process heavy, because it's not fun. I was a 35-year-old man at the time. I shouldn't be that immature. But then we made the commitment to become a process-oriented company. Legitimately, that's the closest we've ever gotten to getting divorced. I legitimately just followed her around and said, and then what do you do? And then what do you do? and, oh, my God, but that's how we drilled out our processes. And now it's not. We don't operate without it. Now, I can't imagine running a business without it. But that conversion was almost as bad as Afghanistan. I would say that it sucked. It's also not fair to team members to give them responsibility without a process.
In terms of implementing systems, I find the other part of this is that as you scale a business and go from two or three people up to 10 or 15, there's an image. For those who've been there, it can be constraining. I used to have the freedom to do this. And now I have to do this. And that's a process you have to manage as you scale up your team? How have you found the implementation of systems and getting it consistent? Was it easy from the start? Or did you have to find the best way of bringing these things in and getting them to live with your business?
Oh, no, it's how on earth it's fantastic. It's like, you've got kids, Jordan. The only way I can express it is by being a parent. Right now, I'm heavily involved with my 10-year-old boy's baseball. And like, I got to tell them, Bring your glove to the game, have your water, and then we're not even talking about getting on the field with a pitcher's glove down in the dirt and stepping directly at the pitcher. Keep your head on the ball. All the cool, fun baseball stuff you don't even get there. You do that 10% of the time. And so, system processes, especially when you're in the beginning, are like nine-year-old baseball. It's the first year your kids play baseball. Like, the first year of kid pitch baseball is miserable. Like, every kid walks, there's no action. And so that's what it's gonna feel like when you implement systems and processes. But it's so worth it for when your kid’s like 11 and hits his first home run. And so that's how I would adopt. It's like something you have to do if you want to be great. So you've just got to suck it up and do it. And then you see the benefits later.
And the truth of the matter is there is not a single way you're going to scale a proper business without that. There's no nope, nope. Business of any scale and capability is going to be able to function without a rigorous process and system, though it's just chaos otherwise.
If you want to your team members, and it's also not fair to your employees like I came to the conclusion on the turnkey side that I don't sell houses, I sell a process. And like, I can only guarantee you that my process will be followed and can only guarantee you that we will do these inspections. And we'll have these rehabs because that's our process, and then we'll do this and property management. And then, if you're buying our process, you're not buying a house.
Can you give us a little insight into your coaching and how people can find it so that I can put it on the website?
Sure. So it's cashflowtactics.com. We work with small business owners, two employees who are making a couple hundred grand a year, and they've always been curious and investing in real estate. We actually have holes, people who are wholesaling clients because wholesalers are essentially traders. They're not investing in long-term assets. And especially since they're real estate professionals. They have to hold on to long-term assets because you can do your advanced costs and depreciation. Pretty much every 100 grand of real estate you buy, you get $12,000 in taxes, and especially wholesalers are going to last a few years for that. We take a comprehensive approach to building wealth and cash flow tactics. So we give you a tax plan. For most small business owners, we cut their taxes in half, then we give an asset real allocation asset plan and so the goal is for people to be financially free in 10 years or less with us.
That Real Estate Fast Five
- What bit of technology product has had the biggest impact on the real estate business?
That's not a knock look like any piece of tech. Are you talking to any piece of technology anywhere? Yeah. I mean, dude, if Zillow didn't exist, we couldn't do what we do. - What is The biggest mistake you've made with technology and your business?
Thinking technology would solve the problem. Not that technology is simply a tool, and then you got to use your brain and the tool to solve the problem. - What's your best advice on how to integrate technology into your business if you're talking to someone new?
You have to really treat it like a newborn baby. The first 90 days really be into it. If you or someone on your team can't be on it every day, you'll waste money. - What is the one thing you wish you'd known about technology when you started the real estate business?
That went to just solve my problems? And I'd have to actually work with it. I wanted it to be a magic pill or a golden ticket. Yeah. - If someone was just starting out, particularly in wholesaling or holding, What are three technology products you would recommend they focus on first?
I would say some advanced CRM, like Salesforce. I would say that for inbound calls, you have to have some technology to make sure that a bomb goes off whenever you view a lead calling in. That's another great tip from Brewer. We'll be within 60 seconds if we're answering live or on demand. 60 seconds. If we get a web form coming in, it's 60 seconds. And then third, probably accounting software, because if you start doing well and making money, you want to keep what you make.
I want to thank you so much for joining us today, Jimmy. It's been a phenomenal pleasure for me to meet you and have a little chat with you.