The Science of Flipping
Lost $100K on His First Flip—Now He Closes 30 Deals a Month and Owns a $20M Portfolio | Tommy Harr
Fri, 11 Apr 2025
In this episode, I sat down with Tommy Harr—a friend, powerhouse investor, and someone I respect deeply in the real estate game. Tommy shares how he went from losing $100K on his very first flip to owning over $20 million in real estate and consistently closing 30+ deals a month. We talked about the gritty lessons that built his empire—cold calling, TV ads, building a sales team, and mastering construction. He also opens up about the sacrifices he made early on, like living in his own living room, and how social media became a powerful tool for raising millions in private capital. If you're trying to go from stuck to scaling, this one’s a real blueprint. -- About Tommy Harr: Tommy Harr is a real estate investor based in Columbus, Ohio, who transitioned from a home inspector to a real estate entrepreneur. By the age of 27, he achieved financial freedom through real estate investing. Tommy has completed over 200 wholesale deals, renovated more than 150 properties, and manages a portfolio of 70 rental units valued at $15 million, along with 25 in-house managed short-term rentals. He is the founder of the Real Side Real Estate Community, where he mentors aspiring investors nationwide. Connect with Tommy Harr Website: Real Side Real Estate Instagram: @tommyharr05 TikTok: @tommyharr05 LinkedIn: Thomas Harr Linktree: linktr.ee/tommyharr05 -- Thank you to Mando for supporting today's podcast! Stay Fresh, Stay Confident with Mando! Tired of body odor? Mando Whole Body Deodorant keeps you fresh for up to 72 hours—pits, feet, and everywhere in between. Grab the Starter Pack and get $5 off (over 40% off!) with code [COLBY] at ShopMando.com. Smell fresher, stay drier, and boost your confidence. Get yours today! -- About Justin: After investing in real estate for over 17 years and almost 3000 deals done, Justin has created a business that generates 7 figures in active income through wholesaling and fix and flipping as well as accumulating millions of dollars of rental properties including 5 apartment buildings, 50+ single family homes, and 1 storage facility Justins longevity in real estate is due to his ability to look around the corners, adapt to changing markets, perfecting Raising private capital, and focusing on lead generation which allows him to not just wholesale and fix & flip, but also accumulate wealth through long term holds. His success in real estate led him to start The Entrepreneur DNA podcast and The Science Of Flipping podcast and education company, and REI LIVE where he’s actively doing deals with members. He has coached and mentored thousands of aspiring and active investors over the last decade. Connect with Justin: Instagram: @thejustincolby YouTube: Justin Colby TikTok: @justincolbytsof LinkedIn: Justin Colby
Chapter 1: How did Tommy Harr start his real estate journey?
if i could go back seven years ago and start telling people about my first house hack i lived in my damn living room and rented all my bedrooms out if if people knew that more and like just document your journey and understand that this stuff doesn't happen overnight it's a you you stumble around if you're like me and you didn't get help in the beginning you stumble around for a year two years three years and then you figure it out find somebody in your market or around the country that does what they say they do vet them out give them your energy and they will take you to the next level so
So it's not as hard as you do it by yourself, but it's still going to be hard. Fail, fail often, fail fast and get to the next level.
What is up the science flipping family? Welcome back to another incredible episode. I have a really good friend of mine. He is an absolute stud in the real estate space. If you are under 30 years old, you're going to want to listen to this. And by the way, if you are over 30 years old and aren't quite where you want to be, you're going to want to listen to this. This man was able to
Starting the business at 23 years old, he was a property appraiser and now has built a multiple seven-figure-a-year transactional real estate business and owns over $20 million in assets. Tommy Haar is here. What is up, dude?
What's up, brother? It's been an honor to get to know you and been in the mastermind with you for a while, but I usually connected a few months ago and it's been a great time.
You quickly became one of my favorite people. And so I was very excited to do this. And part of it is just, you know, I'm firmly believing in your network, you know, the saying of network and net worth. But like, really, I make more money by creating real true friendships, by real connections, right? Not by spending money on ads.
And so immediately, we connected in Orlando, we just basically hung out the whole time we were in a, you know, suite, the basketball game, just talking about real estate. And I was just so impressed. I'm 43. So I have a lot of years on you. But to be able to be where you're at at 30. Um, was so impressive that we just talked about this episode and we said, we got to have you on and teach.
By the way, this is absolutely for people over 30. Uh, but I would also say if you are under 30, I want this to inspire you to know what is real. And then if you're over 30, I want this to be like one of those. Okay, if this guy can do this, you know, it's about time to kick my ass in gear. So you quit your job, you went all in, you did your first fix and flip and lost six figures.
Let's start there because I think most people are terrified to even get going. I don't think I know most people are terrified to even get going in this space. for the exact example that you're about to give. You got into the business. You said, hey, uncle, let's go flip a home together. Let's do this. It'll be our first. We're going to win, get rich. And you lost six figures, right?
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Chapter 2: What lessons did Tommy learn from his first flip?
was because the contractor I hired, I should have fired him within a couple of weeks. The scope of work was super gray and vague. So there were change orders everywhere. We didn't even like say who did labor, who did material. So it was just like the classic, the blind leading the blind. And now I know that you just, you hire fast or you hire slow, you fire fast.
You got to really learn to set expectations properly, not just for contractors, but anybody you go into business with, even new like business relationships and friendships, and then stick by it. Like if it says to fire the person, fire them. You have to stick to the things you lay out. So learned a lot of really good lessons during that first flip for sure.
Contractors forever will be the name of my existence. It doesn't matter how many years I do this. There's always something that pops up. You're like, I cannot believe this is happening. Right. Yeah. And that's why I really encourage people. I'm not like a wholesaling coach. That's not who I am per se, but I do believe to minimize your risk. wholesaling is the best way to get some money flowing.
Would you agree? You know, listen, I'm, I've done thousands and thousands of transactions. I've done thousands of wholesales, fix and flips, and I've done a lot of buy and holds, you know, given the place that you're at right now, what is most of your business made up of? And then why? Cause I know like me again, dude, I'm so impressed with you.
This is why you're one of my favorite people so fast is because you are essentially me 13 years ago, but you've done it at 30 instead of being 43. Right. You're wholesaling a fix and flipping or buying and holding. Talk about that. Talk about what you're currently doing. Like, what does it look like right now? And then why? Why do you wholesale? Why do you fix and flip? Why do you buy and hold?
Why do you make those decisions?
Yeah, we were primarily, I would say like 75, actually it's probably 50-50, 50-50 wholesale to flip. And then maybe like a 5% if you can go to 105 holding rentals, mostly for tax purposes, just because the market I'm in Columbus, Ohio, the cashflow just isn't there in the market rate environment when we're shooting this. High sixes, mid sevens, even into the eights sometimes on a DSCR standpoint.
So we just decided that we were going to go continuing to go all in on wholesaling and and just being really good at finding really good deals. So we're doing anywhere from 10 to 15, sometimes 12 deals a month on the wholesaling side, direct to seller. And then we're doing another 15 to 20, 25 flips at any given time. So we've split it in half.
We kind of divided the businesses and we run them like that because before We would wholesale and then we would buy our own wholesale deals from the company. We wouldn't pay a wholesale fee, but I've got sales guys over there. So we were starving that business of cash over and over again. And we realized we were making less on flips than we projected that we were going to make.
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Chapter 3: What strategies does Tommy use for lead generation?
We've had, I think like 10 deals in the last two or three months directly just from those live transfers from our cold callers. We're paying those cold callers $300 a week. So $300 a week, if they close a deal, they get a bonus, but it's more about the being in the office. They're younger guys usually, and they want to just feel and see what it's like to run a real estate company.
So you can even do it for free if you've got, but you have to build a brand to do that. People are reaching out now. Hey, how can I work for you? And that's one of the ways that we're doing it is putting interns into every single one of our businesses. And we're about to do that on the, on the dispo side, the junior disposition and kind of do that same model.
Yeah. So what would you tell the solopreneur? Like if you said right now, here, dude, here is your game plan every day. You do this. You pull this list. You make these calls. You drive these neighborhoods. What are what would you suggest for the solopreneur? Even if they've done a handful of deals, but they haven't been able to get consistent, like what would you tell that person?
Someone who's never done a deal and or they've done a couple, but they don't really have consistency on it.
Yeah, never done a deal. I mean, pull a list from let's call it PropStream, get a $99 a month account, pull a high equity list, free and clear list or a absentee and get on a four line dialer. So you just got to learn how to just get the nose. You got to learn how to just get over your fear of being on the phones.
Really, that's all it is, is training yourself mentally and then continue to work through that. But if you're a solopreneur and you're actually making money, you've actually done deals, you shouldn't be spending your time cold calling. You should hire that cold calling out. You should be using some sort of virtual assistant to drive that lead flow on the front side.
So you're actually talking to warm leads instead of And they kind of backtrack a little bit. You should be doing 500 to 900 ish dials a day on the solo side. And that should drive one to two leads a day if you get good. So are you do you want to spend three, four hours on a dialer and get told no all the time or get hang ups?
Or do you want to be on the side where you're actually picking up warm leads? The difference between those two is going to be money. Do you have the money to spend on that marketing?
That's right. And most people knew they don't. And maybe they have some money, but I'm not a big advocate of telling them to go spend it. Right. I would rather share the sweat equity and make the dials, get the four line dialer. You're using smartphone, right? Yep. OK. And there's other dialers out there. There's Mojo cells and there's call tools and whatever.
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Chapter 4: How does Tommy manage his sales team?
Like give us some of the KPIs of what you run your team meetings. Like, Hey guys, You know, we have this many leads coming in. We're expecting this much conversion. We're expecting this dollar cost. We're expecting, what are you, what are you looking at when you're running those meetings?
Yeah. So I will caveat and say my business partner, Andy, he runs most of the sales stuff, but I do know the numbers. So we're about 30 leads to contract right now. And then 27 leads to closed on the, on the cold calling side. There were one to eight or 10 on the TV lead side. So those are quicker. They're ready to close faster, but they're more expensive.
I think we're about $4,000 cost to close on the TV and we're about $1,200 for the cold call. But the sales cycle, like you said, is way longer. So we're touching these people 20, 30 times, maybe more. And it's about four to six months on, on those to get them closed.
Yeah. So it's been way quicker. That is that is the challenge that most people don't understand is the reason why people like myself or you like I do TV, direct mail, PPL. I stopped doing the PPC because partly I'm slowing down the whole national thing. I'm choosing the markets I want to be in. But people always want the fast button. That fast button a lot of times means cutting a check, right?
I mean, do you know the number you're spending every month? What do you spend every month on?
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Chapter 5: What marketing strategies drive Tommy's business success?
We're spending $15,000 alone on TV, plus probably the $2,500 agency. So in between 15 and 20 grand. And then we're spending another $10,000 to $12,000 on cold calling, CRM, skip tracing, all that stuff. So we're super lean. We're really good with our data. We're not pulling a lot of lists all the time because we've been in one market for a long time. So nothing's really that new.
It's just recirculating the data.
Well, you're spending 30 grand a month, roughly, right? 25, 30 grand a month. Yeah. That is the fast button. That's what I tell people. Oh, you want it right now? Then just pay your way there like that. So it's the same equivalent of like Disney World, right? I go to Disney World a ton because I have my kids. I buy the fast pass every time. It is ridiculously expensive. It is $200 a day.
Plus you have your normal ticket, which is like $200. So essentially it's $400 for the day, right? Just the tickets. That's not the foods. It's not everything else. Crazy. Then there's another level in Disney World where you can have an actual escort, like a VIP escort that takes you behind the scenes. You're not in the crowds. So last time we went, I paid six grand for that person, right?
Because I'm like, dude, I don't, I want convenience. I want speed. I want now, right? I bring up the analogy to say the same thing you're saying is people need to understand if you want that level of speed of getting your first deal and or getting consistent deal flow, you have to be ready to cut the check.
Agreed. Agreed. And that also doesn't include commissions too. So, I mean, we're stroking huge checks on the commission side. I mean, our guys are making at least $10,000 to $15,000 a month. Yeah. You got to be ready to spend the money. But also if you're listening to this and you're like, I'm not to that point yet. Don't spend the money unless you're ready. You got to get good on the phones.
You have to make every single lead count, especially if you're doing out or inbound. So those are just truly expensive. You can quote unquote waste cold call leads because they're really cheap. We're like 35 to 45 a lead right now dollars wise. So like if you say the wrong things on the phone, you're not throwing away a $5,000 PPC lead. That's really important.
That's right. And so that's the challenge that I find most people is they start spending some money. Like I have one of my coaching students that he's made a couple bucks. So he's like, all right, Justin, what do I start spending money on? I'm like, bro, you just got to be ready to spend money. over like a six month run.
Like do not get scared on month two or month three that you haven't made money back because you need a sales cycle. You need to bring in the leads, nurture the leads and then convert. And so I tell people all the time that like, if you aren't there to run for six months, don't do it. Put in the sweat equity, right?
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Chapter 6: What advice does Tommy have for aspiring real estate investors?
But know when you bring somebody on, then you're taking a couple steps back to buy your time in the future. So you're not going to be closing the deals. Some of those deals might not close that you are going to be on the phones with. So you got to just be okay with taking a couple steps back, knowing that in the future, it's going to be worth it.
And then also as you're right now doing it by yourself, building SOPs for everything. So as you're on the computer in the morning, Loom, L-O-M, your screen, and just talk into it like a third grader.
And those are going to be the way you train your employees because most people, once again, they bring on a VA or a team member and they get so busy doing other things that the VA ends up sucking, quote unquote, this isn't going to be on camera, but They suck, but it's really because you don't have enough time to train them and you're not giving them the time to nurture.
And we've learned that just so many times. We've helped people hire VAs and it's more into you have to you have to be ready for those people. So build those SOPs, build those training docs and do it slowly. Everybody wants to scale and scale fast, but it's it's all about people and processes and it takes time.
Yeah. You know, listen, I've done this business for almost two decades, this business. Right. Yeah. And I think there's a lot of people that don't give enough. I don't want to say respect to it, but like credence is a word that comes like you can't measure the stick to me. Sure. Right. I've done it for two decades. That's a long time.
And so like even you who've done this now for eight years, nine years. Right. I have a decade on you. Yeah. I've built it. So I don't have to even be in my meetings. Right. Like now I enjoy what I do, but like, imagine what you've done in eight years and imagine put another eight on it. Oh yeah. It's going to be great. You're going to be right.
But people don't look at it that the way they look at it, like, Oh, what happened this month or last month? Or how have I done so far this year? We're on April. Like, Guys, stop. Like what I would hope to encourage people listening and watching this right now is like, give yourself the runway to actually win, to be the next Tommy Hart, to be the next Justin Cole.
Because if you start to follow Tommy Hart, and by the way, go follow Tommy right now. Like literally one of my favorite humans. Go to his Instagram. Probably is the easiest place. What? Tommy Hart five or zero five. Yeah. Tommy Hart zero five. Go to his Instagram. He will help you in all ways possible. But you have to understand he's eight years into it.
So if you're less than eight years and you're in eight days, eight minutes, eight months, give yourself the eight year runway to measure Tommy. Don't give yourself eight days, eight weeks, eight months. Give the runway he gave himself. Right. Like we talked about when we started his first deal, he lost six figures on, but he didn't give up on that. He didn't get knocked out. He got knocked down.
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Chapter 7: How can you scale your real estate business effectively?
Yep. And that's what I've seen after almost, you know, 12 years of coaching individuals, the construction component. Yep. That's where a lot of people drop the ball. And I mean, listen, even today, 18 years in, I get contractors that like,
do some nasty shit to me and totally lie and you know whatever so some of it out of your control to some extent but understanding construction really can make or break a deal i did a training last night to i don't know a couple hundred investors and basically i said there's three ways to actually get more deals And one of the three is understanding how to underwrite the construction component.
Absolutely. Because for someone who's going to be doing a rental, that construction component might be way less than someone who's going to be doing a fix and flip or even a burr, right? Yep. So if they're going to be doing a burr, you're going to probably want to put in a good amount of money.
It's going to be the same thing as kind of a fix and flip because you got to force the appreciation so the bank can take you out. Absolutely. But if they're just buying a rental, like a normal rental, not necessarily burring it, then your construction budget might be like 10 grand that they're just going to put in to paint some stuff, rip out some carpet, replace the carpet.
Like you won't have a big construction budget. It's not a burr. But if you underwrite the construction, right, you'll convert more deals because even as a wholesaler, there are so many landlord type buyers out there. That's why I love Columbus. That's why I love price points.
You know, Cleveland right now, we've done a lot of deals in Cleveland, not my favorite city, but the price points are just good flips and good rentals. Yes, they are. Right. And so I would tell people understanding construction is really valuable. I will tell you now my what I call Bubba math.
If you are going to be doing what I call like a repair remodel, paint and carpet, simple, nothing like you're not moving wall like repair. Thirty dollars per foot. You can bank on that's pretty close to where you're going to end up. If you're doing a rehab, new kitchen, new bathrooms, right? New paint, $50 square foot.
If you're doing what I call a redo, this is where you probably got to redo the electrical, probably got to replace the windows, probably got to move some walls, probably got to do like just you're fucking redoing the home, right? That's $70 square foot in most markets. That is not going to be true in San Francisco or Miami. It's going to be more expensive.
But if you're in Columbus, if you're in Charlotte, if you're in Oklahoma City, these are the markets that 30, 50, 70 is a good baseline understanding of where you're going to underwrite that to. And then depending upon... Cleveland's a great rental market. You're probably not doing a lot of 70s. You're probably really a lot closer to 30s, depending upon the condition.
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