• Kevin Hart accumulated a lot of debt after opening his own insurance branch.
• He got out of the red by flipping homes and now does real estate full-time.
• Hart recommends new investors get started with a flip, but cautions against costly mistakes.

Kevin Hart found himself in the red when, after working as a sales rep for State Farm for a few years, he opened his own branch in 2017.

"I was dead broke and at a failing insurance business," the Louisville native told Business Insider. "I had a $50,000 business loan I had to pay back at some point. I had a bunch of credit card debt from trying to get that business going."

Hart wasn't in a financial hole for long. In 2019, he flipped his first home. He said it profited about $30,000, which he split with his business partner at the time. Before the end of that summer, he purchased two more flips and left insurance to work in real estate full time.

He said that his success flipping, and later wholesaling, helped him pay off his debt in two years: "There's not much else out there where you can make lump sum checks to help you pay off that debt."

Hart now works alongside a different business partner, Mike Gorius. They formed an official business partnership in 2024 under the Joe Homebuyer franchise and, in their first full year working together, did 50 transactions between wholesales, wholetails, and flips. They also own more than 20 rental properties, including short-, mid-, and long-term, in the Lousiville area. BI verified their property ownership and deal history by looking at settlement statements and closing documents.

They agree that rookie investors should consider starting with a flip for a "quick capital boost to help you get going," said Hart, whose two-pronged real estate strategy involves flipping and wholesaling to bring in cash, and then buying and holding rentals.

Of course, when it comes to flipping homes, there's always risk involved. To minimize risk and avoid losing money on your first flip, Hart and Gorius highlighted three costly mistakes.

1. Hiring the first contractor you find. Unless you're planning on doing all of the renovation work yourself, you're going to need to work with a general contractor — and finding the right person for the job is key to a successful flip. This is the person you'll be relying on to transform a fixer-upper into a marketable home.

Avoid selecting "some random contractor you find online," said Hart. "You definitely don't want to hire the cheapest one you find. They're probably cheap and available for a reason."

Instead, interview multiple contractors, call references, and look at their previous work. The more due diligence, the better off you'll be.

Keep in mind that there are residential contractors and contractors who work with investors. You want to work with the latter because "they understand what flippers are looking for," said Hart.

2. Biting off more than you can chew. "Don't take on a project that's way bigger than you can handle," said Hart, acknowledging that it's easier said than done, especially if you draw inspiration from HGTV shows that tend to feature full gut renovations. "That's not what you want on your first flip."

If he was starting from scratch in Louisville, he said he'd target a 3-bedroom, 1-bath ranch-style house that could use cosmetic upgrades: "Floors, paint, kitchen cabinets, update the bathroom and a few minor things like light fixtures and call it a day. You don't want to start a huge construction project when you have no experience doing construction."

Stick to the basics, added Gorius: "Don't pretend that you're the one moving into this house and start putting finishes on there that are overpriced or don't make sense. Stick with what works, talk to contractors, and walk other people's flips to see what finishes and paint colors and materials they're using, because they're doing that for a reason."

Their goal with a flip is to create a home that appeals to the most amount of people possible, which means neutral colors and flooring.

"In reality, if you're doing a lot of flips, flipping is a pretty boring business," said Hart. "You're using the same paint colors, you're using similar flooring. Whatever's in style that year, we're like, 'Okay, for the next five houses, this is what we're doing.'"

3. Running your numbers too optimistically. Assume the project will cost more money and take more time than you think.

"Get really good at running your numbers, and be realistic about it," said Hart, who built his own flipping calculator in Excel. That means, if you're running comps and see that one home in your market sold for $250,000 but the rest are selling for $220,000, "you can't get too excited and think, 'my house is going to be worth 250.' More likely, it'll be 220 or 230. Don't try to force the numbers to work."

Allow yourself a financial cushion because, especially as a new flipper, "something inevitably is going to go wrong or you're going to miss something in the rehab," he said. "It always happens. You can't go out there and project a flip is going to make $10,000 off the bat, and all of a sudden, you buy it and miss this $10,000 foundation issue and now you're in the hole. So you just have to make sure you're buying correctly and getting your rehab cost as accurate as possible."

• Phoebe Grier, now 18, flipped a home during her high school summer break.
• She used a hard-money loan and got financial help from her father as well as a private investor.
• Grier made a profit of $39,500 — she saved some, donated some, and bought a car.

This as-told-to essay is based on a conversation with Phoebe Grier, 18, who flipped a home in the Twin Oaks neighborhood of Lexington, Kentucky when she was 16. She used her father's credit to secure a hard-money loan through Backflip, a platform that helps residential real-estate investors find, analyze, and finance projects. The conversation was edited for length and clarity.

The summer I flipped the house, I still babysat and housesat, but that was my job.

When I wasn't playing golf, I was running errands for the house — going to buy things, making sure the things that the contractor said were supposed to be happening were happening and that people and places were where they were supposed to be.

My friends were thinking about going out to eat or buying makeup and clothes. One was working at a golf shop, one was working at an ice cream shop, and one was working as an intern. They didn't really realize what I was doing. They didn't even know what to think.

A lot of people were supportive of the fact that I was a young person who wanted to flip a house. Some people were impressed. Other people were like, "OK, you're a 16-year-old girl. Why am I listening to you?"

If I want to do something, I want to do it. I make it happen. It also definitely helped to get empowerment and encouragement from my parents.

My dad and an investor helped me buy the house and fund the renovation

Since I was little, I've had a passion for design and houses. My mom and I love HGTV — we really bonded over the design shows.

When I was in third grade, I collected a bunch of cardboard boxes and I built a house within my house. Even then, I loved anything related to building houses or design.

I first saw people flipping houses on TV. Then my dad, who was a pastor for most of my life, started working in commercial construction and started flipping houses.

My parents were in a real-estate "mastermind" class, and I went to a session and heard about a girl who flipped a house. I was like, "That is something that I think I could do also — and that I would love and be good at."

With my dad's help, I created an LLC called Phoebe Flips. Because I wasn't 18, my dad and I owned it 50/50. With his credit, through Backflip, I was able to get a hard-money loan to pay for the house.

I had to find all the money for the 20% down payment and the renovation on my own. Through talking with family members and friends, I found a private investor to cover the down payment and the renovation costs.

I bought the house for $234,500, including the 20% down payment, and $80,000 went into the rehab.

I had hoped my budget for the renovation would be around $45,000. I didn't know exactly how much every inch of the house needed to be touched. As the project progressed, no room was left untouched — the floors were refinished, walls were taken down and put up. We painted.

The house was in worse shape than I expected, but it ended up selling in 24 hours

I knew I was going to get a return because of the area that the house was in — Twin Oaks — but it really did need to be gutted.

I got the house from a wholesaler, which can sometimes be a little bit more tricky than buying it via a traditional real-estate agent.

The house hadn't actually been on the market. The day I bought the house, its resident hadn't gotten all of his things out. I showed up with the key, and he was actually there with his sister, still moving some of it.

There were still piles and piles and piles of junk, and it smelled. It was like, "Oh, gosh." With the help of my sister and my mom, we filled up, like, 12 bags of trash just within the first two hours we were there.

We didn't have enough time to get all the junk out ourselves, so I hired Junk Luggers to take it out of the house for $3,000. That was an extra expense that I wasn't planning for.

The renovation was my favorite part, and it was also the most challenging part. I love being able to pick out the fixtures and the different flooring and pick colors — just how it all goes together.

In the kitchen, I originally wanted light blue tiles, but they'd sold out, so I ended up going with dark emerald green tiles.

It doesn't just look like any old house; it doesn't have your average subway tiles and gray walls and boring floors. It appealed to all sorts of buyers, but still had some unique flair.

It took 91 days from starting the renovation to closing the sale.

In the moment, that felt really long, but looking back, I'm like, "Wow, three months."

Within 12 hours of listing, I received an offer over asking price, and in less than 24 hours, I had accepted it. I really did not experience any sort of agony with selling the house. We sold the house for $390,000, so the net profit was $39,500.

I didn't think it would be that fast. I wasn't expecting it to be on the market forever, but my expectation was not for it to be sold within a day. It was kind of shocking. I was really lucky.

I spent the money on a car, but I also donated and saved

With the money from the house, I bought a car. At the time, that was what I was working toward.

I also used the money to save for the school year so that I wouldn't have to have a job while in school.

I tithed and gave to my local church and also gave to two small group leaders who had been mentors in my life.

Some of the money is still in my savings account, but it's not enough to pay for college or anything. I'm going to college at Taylor University in the fall, and I'm going to play golf there. I'm going to study business and hope to minor in either entrepreneurship or Spanish.

I'm very grateful for the opportunity to flip a house. Looking back, 8-year-old me would have never thought she could do this.

• Business partners Kevin Hart and Mike Gorius have built a robust and diverse real estate portfolio.
• Their strategy involves flipping and wholesaling for cash and holding rentals for long-term gains.
• Their advice to new investors is to start with a flip to bring in cash and then expand to rentals.

Kevin Hart started thinking about real estate as a viable business in college when he was renting a duplex with his fraternity brothers.

"We had both sides, there were 10 guys, and we were all paying 500 bucks a month to this landlord," the University of Kentucky grad told Business Insider. It seemed like a relatively simple way to bring in thousands of dollars a month, "so I always had that in the back of my head."

He graduated, started a career in accounting, and found his mind wandering as he sat in his cubicle all day "mindlessly sending spreadsheets," he said. "I was daydreaming about real estate or other businesses, thinking, 'How do I get out of here?'"

His curiosity led him to websites like BiggerPockets. He learned about various investing strategies, "but I put real estate on the back burner because I just thought it was too hard to get started. I didn't have any money and didn't think I could do it."

A career pivot to insurance in 2017 ended up putting Hart in the red. He started working as an independent contractor for State Farm and took out a business loan to help with marketing expenses.

The one major silver lining was that it introduced him to home flippers in his area in Louisville.

"They were clients of mine on the insurance side and motivated me to flip a house and see if it's really for me," said Hart. "I started working with some local wholesalers, found a good deal, and bought this first house with $8,000 down using a hard money lender. My wife was super freaked out about what I was doing because I'd never done it before. Luckily, it went really well."

He said he and his first business partner bought the property for about $70,000 in March 2019, put roughly $40,000 of work into it, and sold it for around $160,000.

"Together we split probably $30,000 of profit," said Hart. He was hooked, bought two more flips before the end of the summer, and quit his job later that same year. "I had these paychecks coming in that were triple what I was paying myself at State Farm as a self-employed insurance agent. That was super exciting."

Hart's current business partner, Mike Gorius, took a different approach at the beginning of his real estate career, which began as a side project to help alleviate credit card debt and car loans. He started by purchasing a duplex in Louisville, despite living in Phoenix at the time, and turned it into a long-term rental.

"I spent about $35,000 on the down payment of my own money. When I got my first rental check, the profit was like $400," said Gorius, who worked in sales and recruiting throughout his corporate career. "I remember thinking, 'Oh man, it's going to take a lot of $35,000 down payments for me to retire off this."

Gorius and Hart, who initially connected when Gorius was looking to buy in the Louisville market, have been doing deals together since 2022. They formed an official business partnership in 2024 under the Joe Homebuyer franchise and, in their first full year working together, did 50 transactions between wholesales, wholetails, and flips. They also own more than 20 rental properties, including short-, mid-, and long-term, in the Lousiville area. BI verified their property ownership and deal history by looking at settlement statements and closing documents.

Thanks to real estate, Hart says he's completely rid of bad debt, and Gorius, who quit his corporate job in 2023 to work in real estate full-time, expects to have paid off his in 2025.

"There's not much else out there where you can make lump sum checks to help you pay off that debt," said Hart. "It's a good business to help you build your savings account."

Their next major milestone is financial freedom and the option to never have to work for income again, though they're not the types to be on the golf course five days a week. They said the flexibility is more intriguing.

A two-pronged wealth-building strategy: Flip to bring in cash, then buy and hold rentals

Hart and Gorius have narrowed in on a real estate strategy that works for them — and they encourage new investors to use a similar approach: Start with a flip for a cash infusion and then use that money to buy and hold rentals.

"If you have 10 grand you can typically go find a deal, put the down payment down, and hopefully you're making $15,000 to $30,000. That's a quick capital boost to help you get going," said Hart. "If you start flipping a few houses a year, whether you've got a W2 or not, that's definitely going to put you in the right direction to be able to do other things like buying rentals."

It's easier said than done.

A common and costly mistake in the flipping world is going with the first contractor you find, rather than interviewing a few.

"Try to get referrals from other flippers. That way, hopefully, you're not getting burned on a bad contractor," said Hart. "You definitely don't want to hire the cheapest one you find. They're probably cheap and available for a reason."

Another rookie mistake is taking on too big of a project. You don't want to be gutting the house or moving walls on your first flip. Instead, start with more of a cosmetic flip where you're updating the flooring, paint, cabinets, and light fixtures.

"In reality, if you're doing a lot of flips, flipping is a pretty boring business. You're using the same paint colors, you're using similar flooring. Whatever's in style that year, we're like, 'Okay, for the next five houses, this is what we're doing,'" said Hart. "We're doing neutral colors, neutral floors, and just making everything fresh and clean so that it appeals to the most amount of people possible."

The money coming in from their flips and wholesales funds their lifestyle and savings.

"Flipping and the wholesaling, that's what I love to do. That's my day job, so I've turned that into my 'salary,'" said Gorius — and it can be lucrative.

He cited their most recent deal: "We got a property under contract 16 days ago, closed on it today, and wholesaled it for $24,000. Because it's a wholesale, that's pretty much gross profit. That's an extreme case. That's a fantastic deal. I will say there are other deals and flips that have been in our pipeline for two, three months now, so they're not all like that. But that is the power of this business."

A successful flip or wholesale can help you build enough savings to start adding rental properties to your portfolio. The problem with starting with a long-term rental is that it likely won't generate much cash flow, if any. In their market, for example, they can profit about $100 to $200 a month per unit.

"If you don't have any money in the bank and a tenant calls you because the water heater went out, there goes a whole year of your cash flow," said Hart. "You really have to be prepared to be able to make these repairs."

They look at their long-term rentals as their retirement funds.

"They probably won't make a ton, if any, money in the short term, but if you hold it for that 20, 30 years, then that's your retirement plan," said Gorius.

As Hart put it: "Buying rental properties is like a slow burn to retirement. No one is getting super wealth immediately, especially not in Louisville." But over time, "The tenants pay the mortgage, we build equity every single month, and eventually, we can sell off and have a nice retirement plan with it."