House Flipping: Rhett Wiseman of Wiseman Advising On the 5 Things You Need To Know To Create A Successful Career Buying, Rehabbing, and Selling Properties

An Interview With Jason Hartman

Jason Hartman
Authority Magazine
17 min readSep 25, 2023


Knowing when to sell. This is incredibly important — if you don’t know when to self, you will not capitalize fully on your investment. People forget that these properties are investments, and you cannot get emotionally attached. These are numbers. Sometimes, people get offered an exorbitant amount of money for a property purchased a few years earlier, and they don’t sell because they’re emotionally attached. It’s been a good asset for them, and they don’t want to get rid of it. Well, the reality is there is a price that makes sense for every piece of real estate that you own. You have to try and remove the emotional part and look at this based on numbers. If you sell for the right price, it can allow you to get into bigger investments that cash flow better or appreciate better, so you have to understand when to release these properties and sell them if the time’s right.

Shows like Flip or Flop and Fixer Upper with Chip and Joanna Gaines have really glamorized the creativity and enjoyment that comes with buying a rundown home, fixing it, and then selling it for a profit. Some amateurs have ventured into this industry and have made a lucrative career out of it. But others, particularly when a market is stagnant, have lost their shirts. As a part of my series about the ‘5 Things You Need To Know To Create A Successful Career Buying, Rehabbing, and Selling Properties’, I had the pleasure of interviewing Rhett Wiseman.

Rhett Wiseman has been building real estate portfolios across the country for the past decade. Beginning with fix-and-flips, on a large scale, Rhett quickly found the value of high-yield returns available through investing in Section 8 rental properties. While simultaneously onboarding units of single-family rentals, small and large multifamily units, and apartment complexes, Rhett was also playing professional baseball in the Washington Nationals organization with a career spanning seven seasons. Faced with the challenge of managing his portfolios while being on the road, playing in multiple different states for seven-nine months out of the year, Rhett learned first-hand the trials and tribulations of the industry. Taking note of his wins and failures just the same, Rhett is able to leverage his experiences and advise his clients correctly, as someone who’s seen and done it all himself. Rhett is considered one of the nation’s leaders on Section 8 real estate investing and has one of the most successful coaching programs in the country for the industry. A native of Mansfield, Massachusetts, Rhett graduated from Vanderbilt University in 2018. Rhett currently resides in Nashville, TN.

Thank you so much for doing this with us! Can you tell us the “backstory” about what brought you to the Real Estate industry?

I started investing in real estate 12 years ago, and the first things I started doing in real estate were fix-and-flips. After graduating from fix-and-flips, I wanted to get into something long-term (long-term holds), so I started investing in Section 8 real estate, where I was creating units in the private sector for people who were in really tough conditions and people who had some saddening backgrounds, and starting putting people into homes where they could take pride in their homes and hopefully get them into a better situation.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

Over the last 10+ years, I have been a part of nearly 2,500 property acquisitions, between my own, personally, and those for clients. We would need a lot more space on this page and time to get into some of the most amusing and interesting property acquisitions that I’ve been a part of [laughs]!

Do you have a favorite “life lesson quote”? Can you share a story or example of how that was relevant to you in your life?

My favorite life lesson quote is: Do what you say you’re going to do. I take that with me in my personal life and professional business life. I think that if I tell someone I’m going to do something, and I do that, that’s more than 90 percent of what a lot of people do. So, if I can live by that, I think I will do very well personally and in business, and so far in my life, that has happened for me.

Are you working on any exciting new projects now? How do you think that will help people?

Yes! Every day in my business, we usually put between 20–30 low-income families into housing through the private sector. Every family we put in a unit gives me a great feeling, knowing that we took people out of really tough situations, whether it be bad, unsafe living situations or have taken families off the street. We do between 20–30 a month, which is pretty amazing, and something that I’m extremely proud to say that I’m a part of. Outside of projects like that, I’m currently in the process of building well over 300 units in Nashville, TN, which will be Airbnb units, workforce housing units, and some luxury units. I’m particularly excited about the workforce housing, as it will be a great way to create new construction for people working in the middle class. I’m also excited that in that area for the middle class, there are not many affordable workforce housing options. Rather, a lot of new construction is very expensive, so many people within that class cannot live in new construction developments inside city limits. So, for this project, 35 townhomes inside of city limits that are going to be focused on workforce housing are really special and unique and are going to allow a lot of everyday workers, hard workers who live in Nashville, to live where they work, and won’t require them to travel too far to where they work.

What do you think makes your company stand out? Can you share a story?

Not many companies out there have as many clients as I do, and every single day, what we do is create opportunities for low-income families. Every day, my clients and I are building substantial portfolios that make up the lowest of low demographics in regard to income out there. We’re doing more — taking young children, single mothers, and vulnerable populations and putting them in safe homes. Not only safe homes but places where they can really have a good shot of ending the cycle of poverty that they’ve been in. So, I think that definitely makes us stand out. A lot of people go after the highest returns or the most luxurious things possible, but we don’t. We’re very focused on the actual person we’re putting in the unit, and we take pride in what we do. We know that when we give people a nice place to live, they’ll, in part, take pride in that unit and then trampoline them into a new phase of their life that’s better than the previous.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Of course — but it’s not a person; instead, it’s two people — my parents. I certainly would not be where I am today without them from an ethical, moral, and business standpoint. They’ve been able to help me get to where I am, and they’ve helped pass on some serious principles and standards that I live by every day. They’ve helped pass those on through me to my clients, allowing them to invest in a certain way and treat people in a certain way in business, that everybody should be treated. The returns are always very important, but when dealing with real estate, you also directly affect other people’s lives. Specifically, in our case, we’re directly impacting the lives of other people who aren’t always as fortunate as we are because of the asset classes that we invest in predominantly. So, having very high standards, morally and ethically, is extremely important in what I do, and that has been drilled into me by my parents, who have both very, very high moral and ethical compasses.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Number one: Leadership.

Number two: Resilience.

Number three: Creative thinking.

I have derived many character traits through seven years of being a professional athlete and a collegiate athlete for three years before that. Playing sports at such a high level and being a leader in the locker room can very easily translate to being a leader in business. Personally, I learned how to be a leader on the sports field, and then I learned how to be a leader in the classroom, which has all transpired into me being a business leader. When you’re playing sports, and you’re on championship-caliber teams, you’re learning how to lead other people. You’re learning how to find accountability in yourself and take responsibility in the things that you do. You’re constantly learning different things regarding resilience and perseverance. You have to fight through tons of adversity in sports, and it’s no different in business. It’s the same with creative thinking. In sports, we’re always game-planning against the adversary, and it’s not terribly different in business. You’re constantly competing with other people, trying to do the same thing as you are, and you have to outsmart them, outthink them, and create a game plan for how you want to succeed. All of these things that I’ve learned through sports, I’ve brought into the picture in business as well.

Ok. Thank you for all that. Let’s now jump to the main core of our interview. Can you share 3 things that most excite you about the Real Estate industry? If you can please share a story or example.

Number one: Attention. So much attention has been put into real estate over the last four years, mainly because of social media.

Number two: Popularity. It’s becoming increasingly popular for people to invest in real estate. You go back ten years ago, and that just wasn’t the case. That relates back to social media platforms and the internet, where a lot of people are sharing their experiences in real estate and finding ways to get into real estate cheaper and more effectively.

Number three (the thing that excites me the MOST about real estate and how it stands right now): The influx of people taking the leap and getting into real estate at a young age. There’s no ability to replace time. Time is, without question, our most valuable asset in any investing. People getting into real estate investing early and young are doing themself an amazing service. They’re able to capture a lot of appreciation and cash flow over a long period of time. There’s no substitute for getting into this thing early, so seeing a lot of young people take the leap is really, really nice to see.

Can you share 3 things that most concern you about the industry? If you had the ability to implement 3 ways to reform or improve the industry, what would you suggest? Please share stories or examples if possible.

The things that concern me most are some of the things that excite me the most. The ability for people to get into real estate more easily is a blessing and a curse. The ability to easily invest out of state, and the ease at which people can get involved and find information so readily accessible because of social media . . . yes, it has created a fantastic influx in popularity and an influx of young people to real estate, but that’s a huge double-edged sword. What I mean by that, and what concerns me the most, is that for every piece of good information on the internet and social media, there are ten pieces of bad information. As a result, you have a lot of young people who want to make money but are very susceptible and naïve, who are shown all these fancy shiny things and are following the wrong people. Not only are they following the wrong people, but there are many people online who aren’t who they say they are or give off the idea that they are very successful, and in reality, they’re not. I think that that’s a huge problem because what’s happening is you end up having a lot of vulnerable people who are investing in property and real estate and don’t understand the true risk. I see people all the time who are taking on way too much leverage because they don’t understand how leverage works. They are investing in areas and places they’ve never been, and they don’t have successful teams on the ground waiting for them to help them on-board properties effectively and efficiently. I see this as a huge issue. I wish there were a way that a lot of these people who are pushing information online could be vetted. Then, there could be ways that people could see what information is real and what information is not before they fall into some of these traps and scams where they’re getting taken advantage of.

What advice would you give to other real estate leaders to help their teams to thrive and to create a really fantastic work culture?

Number one: Communication.

Number two: Make sure everyone moves in the same direction with a shared goal. If everyone has a shared goal, you’re all pushing in the same direction.

Number three (which may be a little surprising): Confrontation. When there are issues within a work culture, they need to be confronted head-on in a non-passive-aggressive manner to put everything out in the open. A team needs to have a level of accountability and responsibility, and to keep those standards high, you need team members to confront each other when there are problems. As long as the confrontation is healthy, I think it is a really, really strong attribute of any team.

As long as everyone has a high standard that they’re working towards and shared goals that they’re all moving forward with collectively, you’ll find that your team starts to work much better than it may be currently.

Ok, wonderful. Here is the main question of our interview. Can you please share with our readers your “5 Things You Need To Know To Create A Successful Career Buying, Rehabbing, and Selling Properties”?

In order to have a successful buying career, you need five things that will 100 percent determine your success if you plan on building a portfolio or buying a lot of properties over your investing career.

Number one: You need successful teams in your corner. It doesn’t matter if you are planning to do fix-and-flips, if you’re planning on buying Airbnb‘s, or if you’re planning on purchasing long-term holds, etcetera, you need a team. On that team, you must ensure you have reliable realtors, contractors, property management companies, lenders, insurance companies — people you can trust. At the head of that team, you need somebody you can go to for answers to questions. You’ll have many questions that pop up, and you need people to rely on. You need someone in your corner, a mentor, or someone with experience doing exactly what you plan on doing.

Number two: To create a successful buying, rehabbing, and selling career, you must know how to analyze property. You need to know how to analyze areas, markets, demographics, tenants, and buyers and understand what goes into the area you’re buying in. If you can’t analyze the right way and you can’t understand what your profits, costs, and expenses are going to be, and everything that goes into the actual numbers behind the property, as well as the intrinsic parts of the property, you are not going to be successful. If your numbers are off, if you don’t have the right financial models to use, and if you don’t have somebody by your side who can help you do that, failure is a likely outcome.

Number three: Knowing how to buy. You have to know how to find the right markets and focus on the right streets in the right markets. When it comes to buying, we’re talking about finding the right properties that are going to appreciate the greatest on a given street, in a given area, in a given market. There are thousands of homes in every market, and you need to buy the right ones in the right places. If you don’t, you’re going to lose money. Regardless of if your goal is for long-term appreciation or short-term, high-yield cash flow, you need to focus on buying suitable properties in the right places.

Number four: Knowing when to sell. This is incredibly important — if you don’t know when to self, you will not capitalize fully on your investment. People forget that these properties are investments, and you cannot get emotionally attached. These are numbers. Sometimes, people get offered an exorbitant amount of money for a property purchased a few years earlier, and they don’t sell because they’re emotionally attached. It’s been a good asset for them, and they don’t want to get rid of it. Well, the reality is there is a price that makes sense for every piece of real estate that you own. You have to try and remove the emotional part and look at this based on numbers. If you sell for the right price, it can allow you to get into bigger investments that cash flow better or appreciate better, so you have to understand when to release these properties and sell them if the time’s right.

Number five (similar to number four, except the exact opposite): Knowing what to hold. Every day, I speak to investors worldwide, and I don’t speak to any investors who tell me, “You know what, I wish I sold this.” Usually, it’s always, “I wish I held this.” We have to know which properties to hold that will appreciate the longest over a long period of time. Getting rid of property and selling it too early can be detrimental, but so is holding it too long. So, just like you need to know when to sell, you need to know when to hold. The only way you can lose money in real estate is by incorrectly timing a sell or a hold. There is a time for both, and you need to understand the right time to do both.

What are the most common mistakes you have seen other people make when they try their own hand at house flipping? Can you share any stories?

That’s very simple — people who don’t know what they’re doing flipping. They spend too much money on rehabs or buy properties at too high a price. People who are just starting out with buying and flipping most often make mistakes at what they purchase the property for and what they spend on rehab. People tend to go over on a rehab for a couple of reasons: either they hire the wrong contractors, people who are untrustworthy and don’t understand what the goal of the property is, or they think they’re on an episode of HGTV and they overspend on things that aren’t going to give them a return on their investment. So, they overspend on unnecessary items — kitchens, bathrooms, fixtures, certain kinds of flooring — that they’ll never recoup on the resale. Mistakes are also made on purchase price. Sometimes, that can get emotional. They may see a house online that they really like or go tour in person, and they overpay for it. Every penny we overpay on a house is a penny we will not get back when we go to sell. I talk to people every single day around the country who are underwater on house flips, and what we try to do is find ways to have them not be underwater. We’ll have them rent to a long-term tenant and get a good return on their money that way, and wait until the market changes and interest rates drop, and then we have them sell. Then, they can sell at a better price because it’s more affordable to the buyer. House flipping is not for people who haven’t done it before, and I suggest that people who do it for the first time have someone help them who’s done it a long time before or has a history and experience of doing it in the past.

From your experience, what can be done to avoid those errors?

It’s all about doing things with people who know what they’re doing. There are two ways in real estate not to mess up: one option is to learn by trial and error, which is very expensive. In real estate, when you make a mistake, it’s not like baking a cake; if you put the wrong ingredient in, it costs you a dollar. When you do the wrong thing when you’re rehabbing a home, it costs you five, ten, 15 thousand dollars. So, you can learn that way (and it’s going to hurt, I promise), or you can bring on a mentor and work with people who have done this before and save you all that time, aggravation, and heartache. That is without question the easiest way to do this — by doing it with someone who has done this before and who’s already made those mistakes for you and has paid for them themselves.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. :-)

I would love to team up with people in cities nationwide to aid in the homeless epidemic affecting our country. From a real estate standpoint, I have some cool ideas that could greatly help not only these people who are living in really tough situations on the street but also the people who are affected by them living on the street every day. I think there are people in positions who are incentivized not to fix the problem, as crazy as that may sound. Bringing real estate experts and real estate thought leaders into that situation would be able to help dramatically, and that is something that I would love to be a part of.

How can our readers further follow your work online?

Readers can check out my website, my YouTube channel @Section8Guy where I post weekly, or connect with me on LinkedIn!

Thank you for your time, and your excellent insights! We wish you continued success.

About The Interviewer: Jason Hartman is the Founder and CEO of Empowered Investor. Jason has been involved in several thousand real estate transactions and has owned income properties in 11 states and 17 cities. Empowered Investor helps people achieve The American Dream of financial freedom by purchasing income property in prudent markets nationwide. Jason’s Complete Solution for Real Estate Investors™ is a comprehensive system providing real estate investors with education, research, resources and technology to deal with all areas of their income property investment needs. Through Jason’s podcasts, educational events, referrals, mentoring and software to track your investments, investors can easily locate, finance and purchase properties in these exceptional markets with confidence and peace of mind.

Starting with very little, Jason, while still in college at the age of 19, embarked on a career in real estate. While brokering properties for clients, he was investing in his own portfolio along the way. Through creativity, persistence and hard work, he earned a number of prestigious industry awards and became a young multi-millionaire. Jason purchased a California real estate brokerage firm that was later acquired by Coldwell Banker. He combined his dedication and business talents to become a successful entrepreneur, public speaker, author, and media personality. Over the years he developed his Complete Solution for Real Estate Investors™ where his innovative firm educates and assists investors in acquiring prudent investments nationwide for their portfolio. Jason’s sought after educational events, speaking engagements, and his popular “Creating Wealth Podcast” inspire and empower hundreds of thousands of people in 189 countries worldwide.

While running his successful real estate and media businesses, Jason also believes that giving back to the community plays an important role in building strong personal relationships. He established The Jason Hartman Foundation in 2005 to provide financial literacy education to young adults providing the all-important real world skills not taught in school which are the key to the financial stability and success of future generations. We’re in a global monetary crisis caused by decades of misguided policies and the cycle of financial dependence has to be broken, literacy and self-reliance are a good start. Visit for free materials and resources.