Rentals and Real Estate Investing in Retirement Basics and Beyond with Whitney Elkins-Hutten

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Rentals and Real Estate Investing in Retirement Basics and Beyond with Whitney Elkins-Hutten

“I believe that everybody should have a real estate portfolio. And even if you're very heavy already into real estate, you should have a mixture of controlled real estate, real estate that you tangibly have your name on the deed or your company's name on the deed. And then also maybe pepper in some passive investments. I know some retirees have deep portfolio of passive investments, but I always encourage people to have their own controlled real estate.

- Whitney Elkins-Hutten, Director of Investor Education at passiveinvesting.com

My guest today is Whitney Elkins-Hutten and she’s the Director of Investor Education at PassiveInvesting.com and a real estate professional.

This edition of The Matt Feret Show will give you an insider’s guide to cashflow real estate investing before or during retirement. We talk about the basics of house-hacking, using single family homes as rentals, being a landlord vs. using a property manager, real estate syndication deals, commercial real estate, apartment buildings, carwashes, and a whole lot more!

Rentals and Real Estate Investing in Retirement Basics and Beyond with Whitney Elkins-Hutten

Listen to the episode on Apple PodcastsSpotify, Deezer, Podcast Addict, Stitcher, Google Podcasts, Amazon Music, Alexa Flash Briefing, iHeart, Acast or on your favorite podcast platform. You can watch the interview on YouTube here.

Brought to you by Prepare for Medicare – The Insider’s Guide  book series. Sign up for the Prepare for Medicare Newsletter, an exclusive subscription-only newsletter that delivers the inside scoop to help you stay up-to-date with your Medicare insurance coverage, highlight Medicare news you can use, and reminders for important dates throughout the year. When you sign up, you’ll immediately gain access to seven FREE Medicare checklists.


“Be very strategic in how you are going to leave your assets to the next generation. I do talks on multi-generational wealth all the time. And the number one thing that I saw in my own family, but also that I see with other people, is that they start gifting things, they start giving things away, and it's creating tax impacts for the people that they're giving to.”

“They're not being as effective with how they could pass on their assets. And so really just sit down with a good retirement strategist and really think through how can you hold onto these assets to create the most cash flow and appreciation for me now in tax benefits, and then how can we organize it and make sure that when it goes onto my heirs, that the (tax) basis get stepped-up for them and we can create win-wins for everybody.”

- Whitney Elkins-Hutten, Director of Investor Education at passiveinvesting.com

“I would really encourage anybody listening, ask that question, what do you want? Why do you want it? And who do you need to become? Those are three questions to ask. And that will really help inform you, do I really want to be a hands-on investor, or do I want to place it with property management? I will tell you, when I added in property management, that allowed me to scale faster, and that property manager was able to work with the tenant far better than I could. They could do so many things far better than I could. I also encourage people, don't get into the real estate game with the idea that you're only going to have one rental property.”

- Whitney Elkins-Hutten, Director of Investor Education at passiveinvesting.com


Rentals and Real Estate Investing in Retirement Basics and Beyond with Whitney Elkins-Hutten

Selected Link from the Episode:

Show Notes:

00:00:00 Intro

00:02:34 Whitney’s Background and real estate qualifications

00:03:26 The Five Freedoms of Life

00:04:38 Single Family Home rentals in retirement

00:05:42 Real estate investment diversification thoughts

00:07:4 How to get into real estate investing

00:08:40 House hacking

00:10:54 Buying a duplex and renting one out

00:11:27 Online rental property tools

00:15:21 How do you know if you’ll make a good real estate investor?

00:18:00 Life goals and real estate

00:19:10 Passive real estate isn’t always passive!

00:22:05 Thoughts on REITS

00:23:17 What are real estate syndication investments?

00:26:02 Apartment investing qualifications

00:29:00 Real estate and “Accredited Investors”

00:31:34 Real estate coaching options

00:34:10 Financial planning, financial planners and real estate investing

00:37:15 Lawyers and due diligence

00:39:14 Goals, risk tolerance and investing horizon

00:21:29 Medigare.gov and online shopping for Medicare Supplement plans

00:23:27 Medigap, Medicare Advantage DIY frustrations

00:44:49 Provisional income and real estate

00:46:45 Inflation, home price appreciation and real estate investing

00:48:41 Cost segregation and real estate

00:51:48 Car washes and self-storage as alternatives to residential real estate

00:59:34 Final thoughts on investing in real estate in your 40s, 50s and 60s

01:02:53 Show wrap

Full Show Transcript:

00:00:00 / 01:02:53


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Matt Feret (00:00:02):

Hello everyone. This is Matt Feret, author of he Prepare for Medicare book series, and welcome to another episode of The Matt Feret Show, where I interview insiders and experts to help light a path to a successful retirement. Say hello at www.themattferetshow.com, for YouTube videos, show links, notes, websites referenced, quotable quotes, and the complete show transcript. Make sure to check out the 2022/2023 second edition of my bestselling book, Prepare for Medicare: The Insider's Guide to Buying Medicare Insurance. You can buy it on Amazon or ask your local librarian to order it for you. Are you in your 40s, 50s, or 60s thinking of downsizing or moving? Have you thought about renting out your primary home or buying a duplex and renting out the second unit?


It seems like there are a million shows on HGTV that make rehabbing, renting and flipping look super easy. Is it? Trying to figure out how to retire early and use rental property cash flow to supplement or even replace your income, even if you have a few rentals already, how do you level up? Group investing, syndication deals? When do you deploy cost segregation strategies? Only have a vague idea of what those last three things are. This is the episode for you. My guest today is Whitney Elkins-Hutten, and she's Director of Investor Education at passiveinvesting.com and a real estate pro. This edition of The Matt Feret Show will give you an insider's guide to real estate investing and it's neatly organized into thirds.


The first third is all about the basics, how to decide whether or not you want to be a landlord, property management approaches, house hacking and single-family homes. We explore how to turn your primary home into your first rental and manage it remotely. The middle part of the show hops into the second level of real estate investing, multiple single-family homes, real estate syndication deals, commercial real estate, apartment buildings, and how to think about all of that as a business. The last third of the show gets into things like cost segregation, real estate professional designations, real estate tax strategy, and other types of cash flowing assets outside of traditional residential or apartment rentals like hotels, car washes, and self-storage units. Enjoy. Whitney, welcome to the show.

Whitney Elkins-Hutten (00:02:26):

Thank you so much for having me on. This is amazing.

Matt Feret (00:02:29):

Tell everybody what you do, how long you've been doing it, and how you help people.

Whitney Elkins-Hutten (00:02:34):

Well, where I'm at currently, I am the Director of Investor Education at passiveinvesting.com. I've been in the private equity space for about six years full time, give or take, a little bit, but that's not how I got started in real estate. But before I move on from what I do now, we specialize in multifamily, hotel, car wash and self-storage, passive deals. We also have a real estate fund. How I got started in real estate was actually as a single-family investor completely by accident back in 2002. I've been in real estate for over 20 years.

Matt Feret (00:03:13):

So you specifically concentrate on, you said passive investing, but it sounds like a lot of different real estate, commercial, residential, single family home. Is that right?

Whitney Elkins-Hutten (00:03:26):

Well, professionally I'm in the private equity space. So what I do is I connect retail investors, private investors, into larger commercial assets. They can not only partner with us and reap the benefits of cash flow, equity, diversification, tax benefits, but also so they can have the five freedoms in life. They can have their time back, they can have freedom of location independence, freedom of choice, of course maybe even have financial freedom, especially that's really important for retirees. That's what we've been working towards. Right? And then also freedom of impact. I know for me as I go through my accumulation phase, I really want to understand, have that space to be like, well, what kind of impact do I want to have in the world? What kind of mark do I want to leave?


Now, I also have my personal investments and so personally I'm very heavy into the passive investing, but I also have single family rentals. I have short term rentals, I have my own self storage. We can go down any one of those rabbit holes if you want that.

Matt Feret (00:04:38):

Well, let's go down that one first. Let's talk about single family home. When people think about, do I get a rental as part of my investment portfolio? Or instead of if I'm thinking about downsizing instead of selling, should I keep it and just rent it out? Let's talk about single family homes first. That's usually kind of the gateway drug of real estate investing. Talk a little bit about if you are in your 50s, 60s, 70s, how should I think about if I'm not in single family or I'm not in any type of real estate actively, as in physical real estate, we're not talking REITs here. But I'm thinking about renting out my home or buying a rental property. How do I begin to think about this as the impact to my life? Is it really passive? Is it passive active? How do I start to think about this from your standpoint, in my 50s, 60s, okay, let's just say 40s too?

Whitney Elkins-Hutten (00:05:36):

Well, okay, so that was like 15 questions.

Matt Feret (00:05:39):

I know. I do that. I'm really sorry. Do you want me to re-ask it?

Whitney Elkins-Hutten (00:05:42):

No, no, no, no. I'm keeping it light here. Right? Let me start unpacking this. I wholly believe that everybody should have a real estate portfolio. And even if you're very heavy already into real estate, you should have a mixture of controlled real estate, real estate that you tangibly have your name on the deed or your company's name on the deed. And then also maybe pepper in some passive investments. I know some retirees have deep portfolio of passive investments, but I always encourage people to have their own controlled real estate. Now, back to that question, should I actually add real estate to my portfolio? I think that answers that. That's a resounding yes. And why is that? Because real estate is the number one asset class that has made billionaires and billionaires over time. It's because it pays you in multiple ways.


Okay. If you think about it, gold is just an inflation hedge. Right now if spent $20 and got ounce of gold in the 1920s, all you did is maintain your purchasing power. The same thing in the 1920s, with that $20 of gold, if you're a man you could get a nice suit, tie, shirt, maybe some shoes, maybe a belt. Today that same ounce of gold, maybe around $1,300 is still going to get you the same thing. It's still going to get you a shirt, completely clothed as a man. It helps maintain your purchasing power. But it's not cash flowing, it doesn't provide equity, it doesn't provide any tax benefits. Real estate does all that. So you get capital preservation. This isn't all real estate you have to buy right. You can get capital preservation, you can get cash flow from it, you can get equity appreciation if you're buying in the right markets. You can get tax benefits, especially if you are moving into the rental real estate.


Next question is, I'm thinking about getting into real estate, what's some glide pass into real estate? Well, starting with your home, if you're thinking about either moving or downsizing, if you are in a great location to where you can cash flow the property, okay, very important. It needs to be able to pay for itself minimally and maybe bring in a couple hundred dollars a month. If you can cash flow it and it's in a good area where it's going to stay in the path of progress and give you a reasonable chance of appreciation, go ahead, turn it into a rental and then go buy your next property. That is one of the easiest ways. And one of the key things is that you actually have probably already locked in a 30 year fixed rate loan. And that is an amazing tool at building wealth, especially for people that are just trying to get into real estate.


They may be hearing all the people that have a hundred rentals and now they're using private lending and commercial lending. You can get an investment property and use the 30 year fixed rate loan. That is unique to the United States. Other countries do not have that. That's why we have a lot of foreign investors coming into the United States to do this. Now, you mentioned in here house hacking. Should I house hack? Well, I personally, that's how I started out in real estate back in 2002, completely by accident. I bought a house with a significant other, relationship fell apart about a month later and everything was under my name and I panicked. And I'm like, oh my gosh, what am I going to do?


I stuffed it full of roommates, people who didn't mind living in a construction zone, maybe I traded a little bit of pizza and beer to get certain things done on the house, painting, flooring, stuff like that. It was a great community. When I put roommates into the property, I was house hacking. It wasn't until I sold the property that I realized I actually made money on appreciation of the house, about $52,000, back in 2002, which I'm wondering. That was amazing for me. I felt like I had won the lottery. But also these roommates had been paying for all the expenses on the property and I was putting about 250, 300 into my pocket every month. And I was like, wow, how many more times can I do this?

Matt Feret (00:10:15):

How many more times can you do that? Exactly. The light bulb goes off, right?

Whitney Elkins-Hutten (00:10:21):

Exactly. Now, if you've been living by yourself for years, with your significant other or spouse or maybe just individually on your own, maybe you've gotten the kids out of the house, do you really want to take on other roommates? Okay. Now it doesn't mean that you need to buy another

Matt Feret (00:10:38):

That's my answer by the way. If the kids are out and it's just me and the wife are just me, no.

Whitney Elkins-Hutten (00:10:45):

I know people who go get a puppy. We just got a puppy this summer and I'm like, that is, no, we're not doing that again. Once everybody's gone, they're gone.

Matt Feret (00:10:54):


Whitney Elkins-Hutten (00:10:54):

But you could go buy a duplex or a quad and maybe live in one unit at the property and you can still access that 30 year financing. That might be appealing for people. That is an opportunity. You could still house hack, you could move into a single-family property and bring in roommates, or you could go buy a multi-unit property and live on the property and bring in other, you're sharing a wall with them, but you get to create your own community there. Those are a few different ways to get involved.

Matt Feret (00:11:27):

Sorry, I didn't mean to step on your mic there. Thank you for answering my multipart question, I have a bad tendency to do that. I'll try to not do that anymore. But if what I'm hearing, it sounds a lot like if you are an empty nester or you're thinking about downsizing, think a little longer. Look at your house as what it is, it's an asset and may still have a mortgage attached to it. It may be 100% paid off and see what you can get for it on the market right now, rents are hot, rents are high. How would you advise someone to go about do that? Just look at their network of people and see who a real estate agent is? Is there a special type of real estate agent? Do I go right to some sort of home inspector or assessor? Let's say I'm trying this for the first time, I'm interested in renting my house out and I'm moving to Florida, or something along those lines. What do I do first?

Whitney Elkins-Hutten (00:12:19):

Really there's a few simple tools on the internet and it's amazing. Over my real estate career there's so many online tools that have come online. It really puts the power in the owner's hands. You can simply go to zillow.com and look at their rent estimator. There's another website called Rent-o-meter. You can just go on there and drop in your address and maybe the bed and bath and what you think you might get and it'll give you a temperature reading, you're too high or you're too low or you're in the sweet spot for what's rent in your area. Now rent cycle. It's really important if you're considering this, look at what rents are in the summer, fall and then winter they tend to dip a little bit lower. What I'm trying to say is if you're initially considering this in December, nobody likes moving during the holidays.


Not a lot of things are renting. You might be a little disappointed to see that rents are pretty low during that holiday season. But look at again during the spring, April, May, June and see if things better align. But that's a good idea, easy way for you to get an idea of what your rents are. Now, you can also go work with a property management company or a realtor that does property management. And they can also, much like when you're buying a house, you get a comparative market analysis of what the value of your house is. They can also do a similar type of analysis for what the rents are based on the amenities that you have on the property, the condition of the property and just the area that it's in.


Now that gives you a little bit of clue, but really the definitive rent that you're going to get is going to come into two additional points of contact. One, when you actually go to rent the property, you're now a competitor in the marketplace place. The renter is going to tell you what they're willing to pay for the property. So if you listed too high and you're not getting anybody, you need to probably start dropping your rents or adding in additional perks or concessions. Alternatively say you're refinancing out, you've owned it all cash and you're trying to refinance out the property and move it to an investment type of property, you're going to get a different type of appraisal.


And the appraisal is going to be the value of the property, that appraiser will do a rent analysis and that appraiser will tell you what they think the market rent is for the property. Now, I have found it that the property manager usually has the better data, but unfortunately the appraiser, unless you have a lease in hand, the bank is going to take that appraised value for rents as the next point of data as you get lending on the property.

Matt Feret (00:15:21):

Makes sense. Thank you. Because I want to move into the whole now, how do I add rentals? And we'll do single family homes and maybe go from there. But before I move to that topic, if I think about personalities or being a handyman or a handy woman, is there a certain type of personality or certain type of investor that does better than others in single family homes? I think I've read a lot and heard stories around certain point if they don't hire a property manager, nobody wants to fix a toilet at midnight, nobody wants to get 15 calls a day if something's wrong. And so, is there a certain personality or any advice that you've got for someone who is thinking about renting their home out or buying their first rental property in terms of what types of personalities and what do you have to think about before really jumping into this?

Whitney Elkins-Hutten (00:16:16):

I'd back it up a little bit, because really it's determined based on your goals. One of that conversation you have to have with yourself is beyond do you need cash flow, equity, diversification, tax benefits, is how do you envision yourself, say five years from now, 10 years from now? How do you want to spend your day, your time? Now the reason why I really encourage people to think about this is that'll give you, if you have that thought in your head, now you can actually start building the business like you want to. You may have to initially start managing properties on your own, but maybe you put systems in place and build out your own management company or you hire a property manager. There are very few personalities that I come across that are like, I love real estate and I love managing it myself.


The property manager is quite frankly I feel one of the most thankless jobs because they have two customers, they have the tenant and they have the investor. I self manage. We still self manage two of our properties because we actually spend time there and we want to be pretty hands on with it. But everything else I learned very quickly that what I valued most beyond getting my goals met between the cash flow and the appreciation is that I valued my time. And whenever it started running over that value of what I wanted, which was my time back, that's when I was like, okay, who do I have to become in order to hit this goal? I need to learn how to build in systems, I need to learn how to build a team, I need to learn how to interview a property manager.


And so maybe not the answer that you were expecting, but I would really encourage anybody listening, ask that question, what do you want? Why do you want it? And who do you need to become? Those are three questions to ask. And that will really help inform you, do I really want to be a hands on investor or do I want to place it with property management? I will tell you, when I added in property management, that allowed me to scale faster, and actually that property manager was able to work with the tenant far better than I could. They could do so many things far better than I could. I also encourage people, don't get into the real estate game with the idea that you're only going to have one rental property.

Matt Feret (00:18:47):

I was going to mention that right before we moved into the multiple piece, because if you're just getting one, maybe you make two, three, four, five, maybe even $1,000 a month, is that worth the hassle or do you really have to have an eye towards expansion?

Whitney Elkins-Hutten (00:19:10):

I would. That's if you're going to be active. Rental real estate, the income is considered passive by the IRS. However, it's anything but passive in regards to your time. It's probably an easy glide path for people to get into real estate. It's one of the most easily accessed ways to get into real estate, because if you've bought your own personal property, you're like, well, I can just either vacate this one and go get another primary, you know how to do that. Or buying a rental property is very similar to buying a primary and there's just a couple little extra nuances to it. Now, I would always add more. Why? For scale, at minimum get 10, because it's not 100% occupied and 100% vacant, you're either making money or you're losing money if you only have one. Okay?


Think about it, maybe you get $1,000 a month when they're paying rent, but if for whatever reason the property's vacant or the tenant can't pay rent that month, you still have bills. Even if you have it 100% paid in cash, I've had this conversation multiple times, you're still paying insurance, you're still paying taxes, you still have expenses, you still have to maintain that property. So definitely I would say if you are getting into rental real estate, think about getting to 10. Now that said, if there is somebody listening to this and they're just like I have no desire to have 10 rental properties, am I out? No, because that's where passive real estate comes in, where you can actually partner with an operator and they actually acquire the property, do the due diligence.


They run the day-to-day operations of the asset, they have property management in place. And you just have to do the due diligence on the operator, vet the market and vet the deal. There's multiple ways you can get started in real estate.

Matt Feret (00:21:13):

Thank you for that, and that's a great segue to this part of it. So aside from renting your own home out or house hacking or getting into, I guess that would be dipping your toe into the rental game and the need for scale there for really diversification purposes, as you mentioned, right? You have one, the rent is either being paid or it's not. But if you have five, 10, you got a nice mix. There are different levels just like everything. So next level would be, what you mean this would be REITs, right? Real estate investment trust that you could just invest in almost like a stock portfolio. Then you've got multifamily/apartments, you've got commercial and then you've got syndication deals or something alike. Can you walk us through those different levels?

Whitney Elkins-Hutten (00:22:05):

Actually REITs are their own kind of different beast because you actually don't get, they knock out a lot of the tax benefits for an investor. I don't even put them in the mix at all. They are a way to get exposure to the real estate market, but as far as creating wealth, you would probably have to get really versed in private REITs to maybe even achieve your goals. I kind of set them aside, they're like a whole different road. It can be a gliding path but there's nothing to say that you need to go from a single family home and then you have to buy a duplex or a five-plex or a ten-plex before you can invest in a syndication.

Matt Feret (00:22:54):

I think a lot of people think that though, because you've got real estate books out there and they're like, well, you can't buy. There's almost like a big boy and big girl club. You can't be an apartment investor unless you've taken your training wheels off. It's almost like this club. Explain why private real estate investing or syndication deals is different.

Whitney Elkins-Hutten (00:23:17):

Let's actually unpack that. What is a syndication investment? It just means a group of investors come together to take down a property. In the space we're playing in, we're taking down say like a multifamily property, it's going to be 60 million or 80 million. I don't have that cash in my bank.

Matt Feret (00:23:36):

Wait, let me check. No, me either.

Whitney Elkins-Hutten (00:23:42):

Okay. We get to leverage the ability of the group to come together, that's performing different functions. We're stronger as a group than we are individually. And so the group is divided then in the limited partners and the general partners. Now, the limited partners are generally the investor, myself included, that are bringing capital to the assets for part of the down payment, down payment on a single family property. Essentially I'm going Matt, hey listen, I'll be the general partner, will you be the limited partner? You bring the money and I'm going to bring the time, knowledge, expertise, the ability to get credit and lending. And by the way, I've got a few other a hundred friends that want to go in on this deal. You game? I'll do all the work, we'll split the profits, how do you like that?

Matt Feret (00:24:34):

Sounds pretty good.

Whitney Elkins-Hutten (00:24:37):

Not all deals are the same, right? That's where you get into syndication real estate 101, you have to learn how to vet the operator, because you're investing in a business now, you're handing over the day-to-day control to an operator. So the operator is the deal. I know so many people that either move from stocks, bonds, and mutual funds. You're trained to look at yield, we're all trained to look at yield there. Or they're moving from their own single family property or small multi and they were the operator. And so you're now handing all that responsibility over to the operations team. This is where the fallacy happens, they start looking at the returns of the deal.


You need to understand who you're investing with, the team, who are they? Do you know, love and trust them? What is their track record? How conservative are they in their underwriting? What markets are they in? What is their investment philosophy? What is their risk philosophy? How are they mitigating that risk? You need to be able to ask those questions. Then you can get into analyzing the market and the deal. But that is really, you don't have to have a single family property or even invest in a duplex to jump right into group investing like this.

Matt Feret (00:26:02):

Really? Okay. So what are the qualifications?

Whitney Elkins-Hutten (00:26:06):

There's no grade book. Nobody's saying pass, fail. Okay. I bless you Matt. Now you can invest in your first multifamily apartment dealing.

Matt Feret (00:26:13):

I'm not wrong though, that does happen. I can go get a loan on a single family property. It's like my own primary house, it's pretty easy like you said. But if I run across, I don't know, an eight apartment complex and I feel like I want to invest in it, all of a sudden all the banks are like, wait a minute. And they start [inaudible 00:26:31].

Whitney Elkins-Hutten (00:26:31):

Oh yeah. Because you're the operator, they're grading the operator. That's why when you do group investing, that's one of the strengths the operator is bringing to the table, because they have the knowledge and expertise, they have the track record, they have the team in place. They're the ones getting graded in order to get the loan. You don't have to do that. You don't even have the loan in your name, so you've eliminated that risk as well.

Matt Feret (00:27:00):

So I'm just a limited partner of a business that's set up to be a real estate acquisition rehab renter, sell property manager, all in one, right?

Whitney Elkins-Hutten (00:27:10):

Yeah. And that's the thing, each operator's going to bring their different type of investment strategy. For us, we like core and core plus assets, so we're looking for A class assets where there's not a whole lot of CapEx or deferred maintenance. We like value add strategies, those type of things that are pretty easy to pull the lever on where we can increase the income, decrease the expenses or add additional streams of income to a property. Now, there's other types of operators out there as well that take more of a development type strategy, deep value add, where they're buying a lot of properties that are pretty distressed or in distressed areas and they're putting layering on a business plan. And depending on the operator they may or may not have a large amount of risk in that business plan as well to achieve their return. That's where the education comes in.


You have to be a little bit savvy and learning how to figure out what that operator's business plan is and does it match your goals and your risk tolerance. And that's where I see most limited partners, investors that are wanting to get into the space stumble a little bit, is that they get so starry-eyed by the returns that they forget to ask the right questions. They end up with an operator that they probably should never given their money to or they end up in a deal where they're just biting their nails because they're just like, I did not know it had this much risk. I thought it was going to get cash flow and I don't get cash flow for three years. What's going on? That's where I see most people stumble when they get into the space.

Matt Feret (00:28:47):

In the space in general, where do I start? A, do I have to be an accredited investor? Let's take a question one by one this time instead of three at the same time. Do I have to be an accredited investor for this type of thing?

Whitney Elkins-Hutten (00:29:00):

You don't actually. Back in 2012 the laws changed and these type of private equity investments could open up to sophisticated investors. It doesn't mean you have to have some sort of knowledge about real estate. Now, again, there's no checklist, there's no test, the Securities and Exchange Commission aren't putting out a spreadsheet going, okay, when you have a conversation with an investor, here's all the boxes you have to check to be qualified as a sophisticated investor. You are just having a conversation with that operator and they need to feel like you understand what the investment is, in that you have a good understanding of how it works, what the risks are, what the timeline of investment is and just how that partnership relationship's working.


Now, there are a lot of deals out there that are open for accredited investors and I'm going to turn the table on its heads, because remember that sophisticated investor has to have a conversation and prove that they know something in a way. An accredited investor, they do have a test, it's based on income or net worth. And as long as they can check those two boxes, there's other ways you can qualify as an accredited investor. They can go in a on deal and never have a conversation with the operator and never actually have knowledge about real estate. And that's really where we try to have conversations with every single one of our investors, because we want to understand that they fully understand what the partnership structure is like.


We want to know them, their goals, what are they trying to achieve and really match them with the investment that's going to help them achieve those goals. Do you have to be accredited to get in the space? No. It's helpful because it actually opens you up to more deals to look at.

Matt Feret (00:30:50):

So let's say I'm in my 40s, 50s, 60s, single family home is pretty, if I want to do it, I feel like I know I how to get into it. Where do I start in something like this? This is attractive. I don't want to necessarily have to deal with a property manager in a single family home or rent my own home out or half of it or house hack. But this sounds really interesting. It's a very different environment though. Where do I start? Do I read a book? Do I go to a website? Where do I start with this in terms of getting used to or getting familiar with this concept and who's out there? And you mentioned a lot of, basically I have to do my own due diligence. How do I start doing that?

Whitney Elkins-Hutten (00:31:34):

And a lot of times people just want to fire Home Depot and Lowe's, especially if they've been managing their own assets. I know that's kind of like where I hit the wall. I was like, I'm done. No more calls to Home Depot. I'll offer a resource if I may to people. I do a Tuesday masterclass, it's called Passive Investing Made Simple. And really the whole point in that masterclass is to be a mentor in this space. People can start gathering that information. It's connected to passiveinvesting.com, but certainly I'm bringing in the knowledge, the expertise and also connecting with people to legal experts, tax experts, insurance experts, so they can really just build up their knowledge in this space and feel confident in going to their first or next deal.


So if I may, you can find that resource at passiveinvestingwithwhitney.com and you can get on that list. That's a great place to start. I wish that was available when I was learning how to get into this space. I unfortunately had a few trials by fire and I'm like, don't do that. I should add that question to my checklist. And so I'm happy to help people shortcut that path and not make some of the mistakes that I've made. Now, there's another great book by Brian Burke, The Hands‑Off Investor. You can find that on Bigger Pockets, I think even maybe Amazon now, that's another great recap. And then as far as finding operators, you can find them, my favorite way of finding great quality operators is going to conferences, real estate conferences.


And I'm not talking about the ones that are like $99, I'm talking about the ones that are high end conferences, best ever conference. We have our own conference, the Multifamily Investor Nation conference. Now it seems like it would only be geared to multifamily, it's not, we open it up to car washes and hotels and self storage as well. That's just how we got started with it. That's where you're going to be able to look the operators in the lights of the eyes and shake their hand and really get to know them as a person. Other ways, you can do a Google search if you want, but I also like attending webinars that operators are doing. I like going to sometimes those online conferences where operators are, but my favorite way is really going to those in-person conferences.

Matt Feret (00:34:10):

Thank you. Tell me about this type of investment and financial planning or wealth managers. My background is in Medicare and one of the points I make multiple times on this show and in my book, is that everybody's got their little niche. And a lot of times financial planners don't know Medicare. And a lot of times financial planners don't really know the best way or when to file social security. May or may not, you may find that you may not, you got to go to the expert. You are the expert, your group of operators are the experts. Is there a gap in the knowledge around this type of investment vehicle for midlife and later life and cash flow in the financial and wealth management space? Or is everybody pretty in tune with it? And if I take something like this to my financial planner, am I going to get a thumbs up or a thumbs down or an inquisitive look?

Whitney Elkins-Hutten (00:35:04):

It depends. I know that's the classic real estate answer. I will say largely on a whole, financial advisors don't know anything at all about, I don't want to say anything at all about real estate, but the private equity space. They're just not savvy in this area. Partly because they don't get paid to connect people to these assets. If it's a product they can sell, they're going to study up on it, they're going to be able to be more knowledgeable about it. Now, I don't know if there's a case where a financial advisor is a broker dealer in private equities. I could see that relationship working, that they might have it, but then they're only going to get paid by the private equity groups that are going to pay the broker dealer fees. You're still not going to get open access to everything, or at least not through the financial advisor.


Now, conversely you can do your own research and take the information to your financial advisor and see how it might fit into your plan. If there's somebody that's savvy, they should realize, they might help you ask some questions and connect, they should connect you to legal and tax help. But really that space, we're actually trying to do some great educational work in that space and really break down these barriers, because it's really, they get paid very differently and money talks unfortunately in that area. It's a topic that I have to, I don't want to say walk on eggshells with, but there's just a lot of disconnect in that space.

Matt Feret (00:36:49):

It seems like it sounds similar to Medicare and social security. It's related but not really in their wheelhouse. And so that's why sometimes I ask that question, if I'm going to start with my accountant or my lawyer or my financial planner, if I have any of those, what reaction am I going to get? I think you spelled it out, what I suspected, which just might be a little head turn. Little what?

Whitney Elkins-Hutten (00:37:15):

Well, your lawyer is going to want to see the private placement memorandum, they're going want to see all the legal documentation and read through it, right? They have very different roles in your team, and I highly suggest you need to consult with your team before you make any sort of investment, point blank, anything, you should consult with your team. But they're all looking at different things. The lawyer is looking at, how can I mitigate risk? That's it. That's their number one thing. They're not going to look at this and go, hey, these are all easy, you can make money. That's not what they're going to do. They're very cynical people. I'm sorry, my uncle's a lawyer. We got one in the family.

Matt Feret (00:37:56):

I think every lawyer would probably buy that. They take that.

Whitney Elkins-Hutten (00:38:01):

Thank goodness that they are who they are. Okay? My accountant looks at it and is like, okay, how are you earning income? How are you being taxed? What are the losses and how you can use them? Again, they're not looking at how you can make money, they're looking at how you can take advantage of all the things that are coming off the tax form, the K-1 tax form. Now a good tax strategist might be able to help you and they should be able to help and inform you on the type of income you have coming in and how you can use the losses and how that might help build your wealth. CPAs aren't tax strategists. Not all CPAs are tax strategists. Just let that one sit a little bit. So you actually have to go find a tax strategist.


Financial advisors have a very different role. They are looking at the income, the returns and the growth over time. It's just that they have a very narrow band of things that they actually recommend. There's a whole wealth of investment opportunity. There's just a very narrow band that financial advising space actually advises and recommends on. I'm sure there's somebody out there for sure.

Matt Feret (00:39:14):

You mentioned the different types of deals out there, yield, cash flow, appreciation and some balance of those, plus tax. If you're in your, I don't know, let's call it 40s and 50s versus 60s and 70s, and the goals here could be different. Have you seen people do different strategies by age or by band? And if so, what do they look like?

Whitney Elkins-Hutten (00:39:42):

It goes back to the goals and the risk tolerance and where you are in your investing horizon. Somebody who's still more in the needs to accumulate more in their portfolio, I would say they need to look at deals that are providing cash flow and appreciation for certain. Now, some people may disagree with me on that. They are like, if I'm in my accumulation phase and I have a good job, I don't need anything with cash flow, I have this conversation regularly with people and I 100% disagree with that. For two reasons. If my goal is to sometime flip that switch and start living off that cash flow, if it isn't coming in already, I now have to wait until I get into assets when it can flip on.


Two, if the asset doesn't cash flow at all, it tells me that it's not stabilized right now. For me, that's not a risk I want to take. I'm a very conservative person. I want it stabilized now. Now I'm okay maybe earning 3% in year one and then getting to seven, nine, 10% by year two, three and four. I'm okay with that, but it's stabilized now. So that tells me that it works in today's environment without the business plan. Okay. Stick a pin in that a little bit. As I get older, maybe I want to flip that switch and go into assets that I now maybe in my 60s I have the cumulation that I want to achieve. Now I just need that money to make a ton of cash flow. Now I'm going to look for deals or tranches in deals that yield higher cash flow and I maybe set aside that equity piece.


Now I did miss, I don't think you can make this cut, but I did miss one thing on the previous scenario with somebody who's still in that accumulation phase that says they don't need the cash flow. Get into assets that do cash flow now, just don't spend the cash flow, allow it to accrue so you can get into your next investment, set it aside, add to it with savings, compound that and add more investments to your portfolio. But as you go through life, really take a look at what your goals, your risk tolerance are and then see if that's what you want to do, shift into assets that provide higher cash flow. I see that quite often, investors that are in their 30s or 40s that have good high paying jobs, they're willing to take on more risks now.


It doesn't mean you have to, I actually say, guard against it. Why? The first rule of investing is don't lose money. Rule number two, see rule number one, and that's not me, that's Warren Buffet. He knows the thing or two about investing. And then as you move into later years of life, really question, do you have the wealth accumulated that you want? And if you're not interested in continuing to pass that down, continuing to accumulate wealth to pass it down, if you can check that box, then maybe shift it to cash flow.

Matt Feret (00:42:59):

If I'm trying to pick right now, let's just say I have zero rental properties, but I've always wanted to get into it and really love the idea of cash flow as part of my retirement strategy. I'm going to put off electing social security benefits until the last minute possible. I can't touch my investments until 59 and a half and I really don't want to given what the market's done. I'm thinking about getting into cash flow, but I have zero. What do you see most often, someone jumping into single family and building that, or would your advice be to skip that and look at these syndication or these bigger deals and being a part of a group? Again, I know it's going to get down to your goals, but if I have zero right now and I want to do this, where would you start, if you could start over?

Whitney Elkins-Hutten (00:43:46):

Great question. If I could start over, well first of all, I had to get started where I did. I didn't have half a million or a million sitting in the bank to start creating a nice cash flowing portfolio with. I had to get into single family properties. I had to learn how to scale there, create value through rehabs and refinances and tenants in order to grow the portfolio that I needed, in order to be able to transition into passive investing. It'd be meaningful. Right? Cash flow is hard, right? If you're just taking money and you're investing in a property and you're not providing any sort of value on it, you might make a leveraged property, you might make two, three, $400 a month if you're buying on cash. If you can buy five properties, $100,000 properties, all cash, come talk to me.


We can get you out of being that day-to-day landlord and probably grow your portfolio faster in passive investments. But it depends on what you have to do in order to get started. I do want to bring up something here, I know a lot of people here are 50 plus. You have to take care and talk to your CPA, talk to your tax strategist about this. If you are going to reach retirement age with more than $500,000 in your IRAs, you got another problem. And it's called provisional income. And so now you have the ability, now what happens here? I am not an accountant, I don't play one on TV, is that you now actually have double taxation potentially going on, because that IRA is going to get taxed some way, somehow.


Now, what doesn't count against provisional income? Life insurance, if you're taking income from life insurance policies and Roth IRAs. And I think there's one more out there. Because why? Because you already paid the tax before it went into the Roth IRA, the tax bill's been taken care of. That is such an amazing gift from the IRS. But if you have a traditional IRA with more than $500,000 in it, you need to talk to your tax strategist to figure out how can I lessen the impact of that. And one of the ways that you can do that is with balancing it out with real estate. And now you might have to take a look with how much real estate do I need to acquire to balance out that tax impact? Do you even want to do that with single families or do you want to have somebody else do the work for you?


But essentially provisional income or that tax impact means that not only does your IRA get taxed, but also all your social security benefits gets taxed. I'm talking it's like 85%.

Matt Feret (00:46:45):

With inflation in the headlines and with home price appreciation going through the roof over the last 24 months, is now the best time to start investing, the worst time or really no different than any other time? What's your take on that?

Whitney Elkins-Hutten (00:47:01):

It really goes back to principle. How do the wealthy people make their money? Is that they learn to invest in any market. So while cash flow might be a little pinched right now in a lot of assets, especially in real estate, I'm still getting capital preservation, I'm still getting equity, I'm still getting tax benefits, I'm still getting an inflation hedge because I can pass through those cost increases to the tenant. Now, for me, with my single family properties and all my multifamily assets, we have over 6,300 units, multifamily or residential units, we're very conscious about how we do that. Because the tenant, they're our customer, I got to treat them right.


But anyways, that's why real estate works, is because even one pillar kind of goes soft, the other pillars support you. Whereas if I'm in the stock market, I'm either making money or losing money, I might get a 2% yield maybe. If I'm in the municipal bond I might get a little bit of tax benefits. I actually have to tax less harvest in order to get a larger tax benefit. And what is that, 3000 a year? I'm taking on, I think I did a cost segregation analysis and we can go into what that is on two properties and I'm going to have a $96,000 loss I can use this year. I'm excited about that because it's a paper loss. That's good.

Matt Feret (00:48:35):

Paper loss and not a real one.

Whitney Elkins-Hutten (00:48:37):

Not a real one. No. I did not lose $96,000.

Matt Feret (00:48:41):

Well, you touched on it, let's hit it, cost segregation and then as a tax strategy. And again, all the disclaimers out there and at the end of the show, I'm not a CPA. You said you weren't either. This is all trust and verify, right?

Whitney Elkins-Hutten (00:48:54):


Matt Feret (00:48:55):

So what is cost segregation in real estate?

Whitney Elkins-Hutten (00:48:57):

You're going do this in single family properties. I'm actually, this cost segregation that I'm talking about, I'm doing it on three units. I have a two unit that are both single friendly rented. One is midterm, one is long term, and then I have a short term rental. That's what I'm doing this on. Now, the power is in scale. We've already talked about that transition into multifamily or commercial real estate. I've got more apples I can pick for the tree for cash flow. The value of the asset is based on net operating income, not based on what the market tells me it's worth. I can also get scale and the tax benefits. And how that happens is that I can hire an engineer, specific type of engineer and they go into the property and essentially there's an IRS schedule that tells you when everything breaks down. Okay?


Because they want you to keep your properties in good repair, right? Because they don't want to get into the housing business, that's not their thing. When does the light fixture break down? When do the window coverings break down, the flooring, all that? Well, when I hire this cost segregation analysis, they're going to break out everything that depreciates in 20 years or less, and they're going to accelerate it to the first five years of the hold of the asset. Instead of me waiting 27 and a half years to hit all these losses for residential real estate or 39 years on self storage type real estate, I can actually get that all in the first five years and I get those losses.


Now, why am I so happy? If you guys were joining us on video. Is because now I can use that to keep, shelter my income on the asset that I'm bringing in monthly or quarterly or annually. I can also use it to shelter income on other passive assets that I own. And depending on if I can check that real estate professional box on my tax return, I might be able to use it to offset other active income. Now, again, not a CPA, definitely work with a tax strategist or a CPA that is very versed in real estate, because they will model these type of losses and the impact it has on your tax situation before you do it. Because cost segregation analyses aren't exactly cheap, but fortunately they've come down in price very recently.


It's a legal way to reduce your tax bill, and it's because you're solving a problem that the government doesn't want to have any part of solving. Maybe that's a little harsh.

Matt Feret (00:51:45):


Whitney Elkins-Hutten (00:51:45):

The investor can solve it better.

Matt Feret (00:51:48):

That's a good explanation of it. All right, again, I want to be respectful of your time, but I did want to, you said this a couple times and it's really personally intriguing, so I thought I'd ask it if it's interesting, maybe it is to somebody else. Car washes, self storage. Self storage you're not dealing with tenants. I guess you are, but not in the same way. And then car washes, I see them popping up everywhere. Talk to me about those asset classes, that's real estate, but that's different than single family or multifamily or any type of rental property out there, the traditional sense. What's going on those markets and how do I get involved in that?

Whitney Elkins-Hutten (00:52:30):

Definitely. So to answer the question in reverse. How do you get involved? Especially if you want to get involved passively, reach out to me at the passiveinvestingwithwhitney.com. I would love to talk to you about that. As far as self-storage, okay, kind of a glide path. I think it's easy for people to jump from multifamily as self-storage, right? Multifamily, you're somebody like living in a unit, we all get that, right? Instead of having one single family houses, you now have maybe a hundred or 200 stacked all on top of each other. Now, these people probably there's not as much room for them to store all their belonging, so they might actually have to get a self-storage unit. And that self-storage unit, think of it, is the garage. Instead of just having one garage now you've got 100 garages or 500 garages.


Now the beauty of self-storage is that the operational expenses of these assets are pretty low, right? It's four metal walls and a concrete floor. That also means the depreciation on that is pretty low, because four metal walls and concrete floor don't really depreciate in 20 years or less, it stretches out to 39 years. Self-storage is a really sticky asset class because once people normally put their belongings into self-storage, let's say they pay $100 a month for it, their monthly leases and the next month my costs went up, I can now pass through that cost. Maybe they went up 3%, now it's $103, or maybe it went up 10%. It's 110. Somebody's not going to go rent a U-Haul and get all their buddies together to move across town for 60 bucks or 30.

Matt Feret (00:54:20):

That's what you mean by sticky. Once your stuff is in there, it's in there, right? Cleaning out your own garage, how often does that happen? It's the same concept. Right?

Whitney Elkins-Hutten (00:54:29):

And they cleaned out the garage and they put it in the storage unit, it's out of sight out of mind. Okay? And again, that inflation hedge, I can adjust those rents on a monthly basis. This area is still, it's started consolidating from mom and pop owners into more private equity groups and now into larger Blackstone in the past 10 years. Now we transition into car washes. Car washes are in the same type of disruption phase that soft storages was 10 years ago, but now it's happening today. A lot of people that hold car washes might have somewhere between one to five facilities. They're mom and pop owners. They are running everything themselves. There is no third party management. And a lot of times they're realizing they're not able to actually make the money that they thought they were going to.


They don't have a marketing team, they're not large enough to be able to command huge breaks and chemical supplies or anything like that. Enter us, what we're doing is that we're actually solving this issue, disrupting by acquiring these properties that are undervalued right now and also building out the third party management company the exact same time. So now we can actually create a value add strategy by commanding these larger discounts on chemicals and stuff like that. We can also centralize the team. So instead of having multiple full-time employees over maybe one or five properties, I can now share those out over maybe 10, 15, or 20 properties. It's better for the employee because they get more hours, but it's also better for us to man manage the full-time employee cost, the labor cost.


Anybody that runs a business here, what is your number one control of expense? Your employees, your labor. And so it's win-win that we're creating here. And we're able to just better manage these properties. We're also layering on subscription models to this. I don't know if anybody is like, you used to be able to pay Netflix, you paid for the number of videos, now you just pay $10 a month, right? It doesn't matter how many videos you watch.

Matt Feret (00:57:00):

$10 and then $12 and then $19.

Whitney Elkins-Hutten (00:57:04):

I don't even know what it is now. Don't ask me.

Matt Feret (00:57:05):

You know what it is, it's enough that I canceled in the last 12 months. That's what it is. My kids hate me for it, but I don't care.

Whitney Elkins-Hutten (00:57:16):

For our subscription model, and this is just one data point, our lowest subscription is I think $25 or $30. And the average person, subscriber washes their car 1.8 times a month. You're just like, okay, what's the margin there? Well just take into account the chemicals, the water, and the energy. Okay? And this does leave out the labor costs, but just those three alone, it's about 80 cents a wash. That's a pretty hefty margin there. That is huge.

Matt Feret (00:57:50):

Pretty hefty margin.

Whitney Elkins-Hutten (00:57:51):

$23 to $27 to pay labor. Now you're cranking 100 or so cars through potentially an hour in these express tunnel car washes. And so there's a huge value to that. I don't call it commercial real estate, it's kind of a hybrid. It's a business. You're investing in a business, the operational business. But we also buy the underlying real estate with it for two reasons. One, we don't want to get five years into the business plan, and then the landlord go, hey, guess what? Your lease is up, right?

Matt Feret (00:58:25):

By the way, I see you guys are doing really well, now the rent's double.

Whitney Elkins-Hutten (00:58:32):

Exactly. Also when we go to exit, we're looking to exit either as an IPO or to a REIT. They're going to want to know that that land is owned. They don't want to get into the same issue as well. So that combined with the third party property management actually solves this consolidation problem that nobody's chosen to solve until very recently. But they are great cash flowing asset. There's some modest appreciation on the back end as well, and they give amazing tax benefits.

Matt Feret (00:59:04):

This has been really fascinating. It has been. I know you've sprinkled in your contact information throughout the show, but give it to us again. How can people find out more about everything that you've talked about on the show?

Whitney Elkins-Hutten (00:59:17):

Absolutely. If you're wanting access to all these tips and tools or even my calendar, go to passiveinvestingwithwhitney.com. You can register there. You'll get my contact information. It's one stop shop. You can just go there.

Matt Feret (00:59:34):

Awesome. And what question or questions that I should have asked, did I not?

Whitney Elkins-Hutten (00:59:46):

Really, especially when we've talked about that a lot of people that are listening here are in their 40s, 50s, maybe even 60s, is what is their exit plan with their portfolio? I'm total buy, borrow and die. I am passing everything on. I guess it's not so much a question, but maybe an early nugget I want to leave people, is be very strategic in how you are going to leave your assets to the next generation. I do talks on multi-generational wealth all the time. And the number one thing that I saw in my own family, but also that I see with other people, is that they start gifting things, they start giving things away, and it's creating tax impacts for the people that they're giving to.


And also they're not being as effective with how they could pass on their assets. And so really just sit down with a good retirement strategist and really think through how can I hold onto these assets to create the most cash flow and appreciation for me now in tax benefits, and then how can we organize it and make sure that when it goes onto my heirs, that the bases get stepped up for them and we can create win-wins for everybody.

Matt Feret (01:01:07):

That sounds wonderful. Whitney, thank you so much for spending time with me today.

Whitney Elkins-Hutten (01:01:11):

Absolutely. Thank you so much for having me. This has been amazing.

Matt Feret (01:01:14):

My thanks to Whitney Elkins-Hutten for really interesting conversation. Make sure to hit The Matt Feret Show website for all the links Whitney and I talked about, plus the full show transcript and quotes. Until next time, to your wealth, wisdom, and wellness, I'm Matt Feret and thanks for tuning in.


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Matt Feret is the host of The Matt Feret Show, which focuses on the health, wealth and wellness of retirees, people over fifty-five and caregivers helping loved ones. He’s also the author of the book series, Prepare for Medicare – The Insider’s Guide to Buying Medicare Insurance and Prepare for Social Security – The Insider’s Guide to Maximizing Your Retirement Benefits.

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