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Using Both Sides Of Your Brain In REI – The Art And Science Of Off-Market Acquisition With Jeff Stephens – Real Estate For Women

REW 55 Jeff Stephens | Off-Market Acquisition


If you’re following an extremely conventional path of looking only at listed properties, you only get to grow at the rate the market says you can grow. There’s freedom in off-market acquisition that allows you to focus more on connecting with your clients. Moneeka Sawyer’s guest for today is Jeff Stephens, the founder of The Thoughtful Real Estate EntrepreneurMoneeka and Jeff discuss using both sides of your brain when interacting with your clients. Real estate tends to be very left-brain. Jeff explains you work best when you use both. You need to be analytic but also empathetic. Tune in to learn more! 

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Using Both Sides Of Your Brain In REI – The Art And Science Of Off-Market Acquisition With Jeff Stephens – Real Estate For Women

Real Estate Investing For Women

I am excited to welcome Jeff Stephens to the show. He is the Founder of The Thoughtful Real Estate Entrepreneur and host of the show, Racking Up Rentals. Jeff is a full-time real estate entrepreneur by day and a real estate investing mentor, coach and podcaster. His focus both as a real estate entrepreneur and coaching others is on growing a rental real estate portfolio that builds long-term wealth through the timeless fundamentals of relationship and negotiation directly with the seller to buy off-market properties with seller financing. You can visit him at ThoughtfulRE.com for more information and we’ll talk a little bit more about that. Thank you, Jeff, for coming to the show. It’s nice to see you again 

It’s nice to see you too. Thank you for letting me be a guest on your awesome show. 

It’s my pleasure. Ladies, when I was on Racking Up Rentals, that was probably one of the nicest, most blissful conversations I’ve had on someone else’s show. You need to go check it out. It was good. I love this whole idea of thoughtful real estate. It’s very aligned with my idea of bliss. Jeff, could you tell us about your story and what brought you to where you are now? 

The right approach to real estate investing is the approach that feels most authentic and aligned. Click To Tweet

I first fell in love with real estate probably in the way a lot of peope did, which is we picked up a book that has a lot of purples and the word Rich Dad in the name. This is going on many years ago. I got excited and I’m a high-action taker. We bought a property. It was a very conventional deal and that went fine. It was not the most exciting transaction but it was okay. I got more excited. I got started, then learning some of the more entrepreneurial ways to do real estate. I went down the rabbit hole of all that education, but I’ve hit two walls that led me to where I am. 

The first wall was when I was attempting to do some wholesaling. Deep down, it didn’t feel super authentic to me, but I was taking action. I thought that’s what you were supposed to do. I had this traumatic experience one day, where somebody showed up on the doorstep of my own home. I had gotten myself into a transaction and I was trying to wholesale it. He was standing on my doorstep, angry, pointing at me and saying, “I see what you’re trying to do here. This is sleazy. We don’t do that kind of stuff around here.” 

Maybe that doesn’t sound that traumatic but for me, my whole life up to this point was like, “Jeff is a good boy. Jeff follows the rules. Jeff does the right thing, and this was my early twentiesThat rattled me to my core. It practically knocked me out of the game for about seven years. I continued to dabble, but I would do very benign types of things in real estate. Eventually, I thought, “I have to do more because I want to learn this.” I got back on the horse and I started learning again. I found that the more I connected with people, the more success I had in the sense that they liked me. We could come to an agreement, but I couldn’t always figure out how to structure the deals. 

The second wall I hit was when I saw that I had some peers who I respected who were getting deals done that I could not figure out how to do. When they would explain it to me, it sounded like they were speaking a completely different language. At that point, I hit that second wall. I did what I needed to do to learn more creative deal structuring. The two things clicked for me, an approach that felt authentic to who I was and secondly, the technical toolbox I needed to be able to get deals done. Those two things together then catapulted my progress from there. 

It’s interesting the way that you talked about that because one of the taglines of this show is, “Goals without action are just dreams. Get out there and take action.” First of all, when I say that, it’s because taking action is one of those barriers. A lot of people won’t act. They want to learn and learn. We get stuck in analysis paralysis. We get stuck in, “I need to take one more course. I don’t know enough.” However, just taking action is also not the solution. We want to take action, but we want to take intentional action. 

What I love most about what you talked about is this thing about feeling inauthentic or sleazy. It doesn’t matter one way or the other what anybody else thinks. What matters is what you think of yourself. A friend of mine, Leeza Gibbons, will often say, “You need to earn the right to your own respect.” Earning the right to your own respect is feeling good about who you are, how you’re showing up in the world, and what you’re doing. There are a million ways to make $1 million in real estate. Choose whatever makes you feel good. Learn about that and then take action. 

It’s the self-image of how you see yourself. I can’t think of anything much more important than either be an enabler or absolute restraints to where you’re trying to go. The right approach to real estate investing is the approach that feels most authentic and aligned. A word I think about a lot is alignment. Until you get that alignment, you’re just trying a lot of different things, but once you get it, for some reason, things seem to take off. 

They’re simpler. You’re more successful. You’re able to stick with it when challenges happen because we both know challenges always happen, then you’re able to get through them. It becomes more of a growth experience rather than a taking you off the horse experience like you had. 

It becomes a North Star. You get to a point. You find that challenge and say, “I know that my guiding light is in this direction because that is authentically who I am.” It does help navigate difficult decisions or situations. 

Let’s talk about what you do. You focus on owner financing, which means your acquisition process is going to be a little bit different. Let’s talk about that acquisition. You do more off-market rather than listed properties. 

My heart is in long-term holds. I love the fun, excitement and entrepreneurial opportunities of things like flips and whatnot, but I primarily look for long-term holds. In that process that I described there when I was stumbling around in the dark, trying to find alignment. I realized that I like to connect with people. I feel I’m an introvert, but I like to connect with people. They seem to like to connect with me. I thought, “There’s clearly a correlation between the success I’m having and my contact directly with the person on the other side of the table.” I started to think, “Do I need people or agents standing between me and a seller?” I started to realize, “No, I feel like it’s almost like I’m a tailor. If I can measure the seller in a lot of different ways, I can propose something that’s going to fit them well.” 

My whole approach now is finding the people with who I can connect and sit down face-to-face to see if we can work something out together. Oftentimes, that does lead to seller financing. I have a belief that as real estate entrepreneurs, we should get to have the right to grow our portfolios at the rate that we want to. I feel like if you’re following an extremely conventional path of looking only at listed properties and going only to banks and credit unions for loans, you get to grow at the rate that the market and lender say that you can grow. I like the freedom of these off-market deals and the seller financing that can come with them. 

REW 55 Jeff Stephens | Off-Market Acquisition

Off-Market Acquisition: Find people you can connect with and sit down face-to-face to see if you can work something out together.


Talk to me about this phrase that you use, “Solve the person, and then you can solve the deal.” I know you’ve already alluded to that, which is why I wanted to continue that conversation. 

I have a framework called the Y.E.S.S.E.S Framework. The two Ss in the middle are solve the person and then solve the deal, but solving the person comes first. What this means is real estate is dirt, sticks, bricks, but real estate doesn’t sell itself. People sell real estate. To me, even though the words it’s a people business might sound a little trite, I can’t believe how true it is. I believe that you have to solve the person before you can solve the deal. If you don’t understand the person on the other side of the transaction, what they’re trying to accomplish, what matters to them, what they think about their own property, what they think about the economic climate, the market or a million things. If you don’t have the empathy to be able to understand the other person, whatever proposal or offer you put in front of them is going to be a version of a shot in the dark. 

I know that so much of the time, when people are teaching real estate, there’s an adversarial attitude like, “I need to get the best deal.” They give a lot of lip service to, “I’m going to help that person.” I’m like, “You’re getting a property at $0.60 on the dollar is helping them get out of a problem.” To me, that feels inauthentic, not because it’s not true. In many cases, it is true but it’s the approach about it. It doesn’t feel like you’re on the same team. It feels like you’re on opposing teams. I love how you talked about when you’re solving the person, you end up being on the same team to make everybody happy. You’ve got something that will make you happy, and they’ve got something that will make them happy. 

One of the most powerful questions I’ve ever asked a seller is, “Paint a picture for me here to understand how you’d like to see this thing come together.” In “normal” real estate, nobody asks that question because it’s more about protecting your own interests. I believe that Jeff is going to get more of what Jeff wants if Jeff helps somebody else get what they want. Not to talk about myself in the third person or quote Zig Ziglar too much, but I do honestly believe that. There’s this coexistence simultaneously of self-interest and helping somebody else. I believe it’s best for me if I do what’s best for them. That’s been my experience. 

Talk to me about this belief that you have that you need both sides of the brain to be successful in real estate. 

Real estate tends to be a very left-brain. They’re very analytical. 

There’s one that’s analytical. 

There’s one that’s relational, intuitive and creative. I think that we are at our best when we have both of them firing simultaneously. A great example is when I’m sitting in a seller’s living room. That’s my venue. That’s my arena. That’s where I go to step onto the stage. I am talking to that person and trying to solve the person, which is very right brain. It’s relational. I’m trying to ask good questions, listen and read between the lines. Meanwhile, there’s this computer apparently in the back left corner of my brain that is calculating like, “Here’s the possibility with this. We could buy it for this. The rents would be that.” 

Both things are happening simultaneously. What we do ilike a dance with the seller. Like any dance, you got your arms around somebody. There’s a leading and following that happen at the same time. I feel like that’s the left brain, right brain thing here a little bit too. There’s so much value in thinking through the possibility and then asking a thoughtful question to that seller that may tests out that opportunity. It’s a dynamic balance of the two thought processes. Most real estate people grab a clipboard, and they’ve got a worksheet of questions. They’re like, “How many bedrooms are there? When was the furnace replaced?” They’re just making entries into a database and a computer. They’re going to hit the submit button and come out with an offer. That’s not how I do it at all. 

In real estate and in any kind of investing, the numbers have to work. We don’t make money unless the numbers work, but I agree with you that it is a people game. We talk about selling real estate and people think of it as hardcore, but it’s also buying. We are buying so that then we can sell too. Both sides of those are all about the relationships that we build, whether we’re building with a seller or buyer. There are a lot of other relationships we’re building. We’re building maybe with agents, vendors or a bunch of different people. I love what you’re talking about here that it is a relationship business because once the numbers work, the rest of it is all how we show up and build those relationships. 

I couldn’t even say it any better than that. It’s true. We’re not going to get the level of collaboration, cooperation and flexibility that we need if we don’t have sharp people skills to deal with the most important ingredient in the whole recipe, which is the humans. 

Could you tell me the five myths of seller financing? 

Yes. I love talking about seller financing for reasons we’ve already discussed. When I observe people talking about seller financing, there are a few things that they make as assumptions. These myths are assumptions. These are the five that stand out to me, and then the quick way I can refute each one. Number one, people think that seller financing is what a seller does when they can’t sell their property in the other way. We’re looking at something that’s been sitting on the market forever, funky or not financeable. While those things might be levers that would lead to seller financing, there are plenty of sellers who want to do seller financing. 

With a little light bulb that you could help come on in their brain, they would realize that it is in their very best interest to do so. To put it very simply, those are the people who might have capital gains concerns. A well-structured seller financing deal would help significantly with that. Those are the people who want to sell a property but they don’t want to give up the income stream that they have. I’ve had sellers call me and in the very first contact, they said, “By the way, I want to sell this on a contract.” It doesn’t get any better than that for me, but there are people who want to do that. That’s the first one. 

The second one is the inverse of that. That is seller financing is only offered because the buyer can’t find any other way to pay. That’s not the case either. A lot of people like me could finance a deal in lots of different ways. At the end of the day, I believe a well-negotiated seller financing deal is framed around what the seller wants to accomplish. It isn’t that the buyer can’t do it in any other way. Maybe there are some scenarios like that, but that’s not always true by any stretch. 

Number three is that people tend to think seller financing loans have above-market interest rates. This ties into the first two, which the seller doesn’t want to do this but if they’re going to, they’re going to demand something super high-interest rate. While there are scenarios where I’m sure that that does happen, if you can find a seller who has the proper configuration of motivation, maybe you can unpack that conversation with them in a way that helps them understand the benefits. They will be more than motivated to simply provide very reasonable terms. It very well might not be much different interest-rate-wise than what you could get with a financial institution. 

The fourth one is that people tend to think seller financing loans are for short-terms. That also sprouts off this idea of, “The sellers don’t want to do this anyway. I better be fast if I’m going to have to carry this note.” There were a lot of people who want to sell their property and continue to get an income stream for selling it for a long time. They want to take their capital gains and punt it as far into the future as they possibly can. Short-terms is not another issue for me or for most of the people that I work with at all. 

The fifth one is that seller financing is only possible when a property is owned free and clear. It’s probably simpler, and there might be more options when it’s owned free and clear. Seller financing is a broad umbrella of things that could fall underneath it. Mostly what I do and teach people is about what I call note and trustee investing, “I am becoming the owner. The seller is now becoming the bank and I make payments to them.” There are other things that would be creative deal structures like lease options, land sale contracts or lots of other different things that could be considered seller financing. I think of it as a bunch of tools in a toolbox and based on what the seller’s situation is. One of those elements of their situation is outstanding debt, then you pick the right tool out of the toolbox and get to work. 

I’ve had a few other people on the show talked about they create the notes themselves so they become the bank. They’ll buy a place and put their 20% down. They might get a loan at 4% or 3%. Someone else who might not qualify for a loan but is looking to buy, they’ll then sell it to them and carry it back at 5.5% or 6%. They’re making the delta. They’ve got some cashflow and also helped someone get into a home who wouldn’t normally be able to get into a home. Other people can also be doing this. I know that there are a lot of people, especially here in my area, where their houses have appreciated dramatically, but they’re no longer working. They’re looking for ways to create cashflow. They know in real estate investment, they’re not going to be able to make more than a couple of percents. You’re able to offer them something attractive that helps them supplement their Social Security or whatever it is they’re planning to retire on. 

Solve the person, and then you can solve the deal. Click To Tweet

There are a few simple clues that you can listen for that a seller might say. For instance, they might say something like, “I’d love to sell this property, but I don’t want to deal with the capital gain. I feel compelled to do a 1031 exchange, but the truth is I don’t want to trade one responsibility for another.” They might say, “I want to sell this property, but I don’t know what I would do with all the money anyway. I want to sell this property, but I don’t like the stock market. It makes me feel uncomfortable. I like tangible assets.” All of those things are clues. It can be a very great solution for you to propose to them that is also excellent for you as the buyer. It scratches their itches perfectly. They might not be aware of that yet, but if you unpack that conversation with them in a thoughtful and sensitive way, they’ll get the picture for sure. 

Could you share with me how do you structure it to avoid capital gains? I know you’re not a lawyer or CPA. Could you give us a high level of what that looks like? People have said it all the time and nobody will explain that. 

I will explain it to you like I would when a seller asks me that question. Thank you for the disclaimer. I always make that disclaimer to you. I’m not a CPA. Here’s the big picture as I’ve understood it in a non-technical way. When you sell your property, you will find yourself receiving a capital gains tax bill in a way that’s correlated with when you receive the gain. If you bought a property for $200,000, now it’s worth $700,000, factoring all your things like depreciation and all that complicated stuff. The main idea is you have this big gain of $500,000 or so. As you receive that gain back, that’s when you will be expected to pay the tax. 

The concept with a 1031 exchange is, what if I don’t receive that gain back at all, it goes straight into a third-party intermediary and then I’m not getting the bill? The same idea applies here to our seller financing structures that say, “Let’s make sure that you are receiving your gain on a schedule that correlates with when you want to pay this tax.” As the buyer, if I come along and say, “I’d like to give you a down payment and then make monthly payments to you over time,” the basic idea is if that down payment is going to be part of the gain that they receive, they might have a little tax bill from the down payment. 

If the payments are interest-only, they’re not receiving a principal or gain back during each of those payments. They’re avoiding that capital gain at that time until there’s maybe a balloon payment at the end. You have to reckon with the gain one way or the other. It’s about asking the seller, “When and how do you want to do that? Let’s work backward to structure the timing of your receipt of that gain in a way that works for your financial strategy.” 

I am in the process of creating notes. I’m buying small houses and creating notes. One of my ladies is doing the same thing with me. She was talking about you can structure it so that you pay the capital gain. Let’s say we structure a note for seven years. You can either pay the capital gain at the end of the seven years, or you can pay it annually so that you don’t have this big capital gain that you’re paying at the end. Is that true? 

Part of that is a little above my pay grade as a non-CPA. If the loan was amortizing heavily over seven years, then I can see how that would trigger an equally amortized capital gains bill. Perhaps there are other provisions that allow you to make installment payments on future capital gains. I don’t know how that part works. Most of the people I work with are thinking, “I’ve got this gain. I’ll figure it out later. I know I don’t want to deal with it now. Give me a small down payment, so I know you’ve got some skin in the game, but not too much because there’s going to be a tax bill associated with that.” We’re going to set a ten-year term and I’ll deal with it then. 

I can see why some would be like, “I know I’m going to sell this. I don’t want to have this big bill at the end.” Although if you get the big bill at the end, there are other ways to deal with it too. I hadn’t heard of anybody talking about that. I wasn’t sure if you had heard about it. 

An important point off of that is to do this as the buyer, you don’t have to be CPA-level informed on every nuance of that area of the tax code of the installment sale. There certainly comes a time when, as a thoughtful person who’s dealing empathetically with the seller, you’re going to want to say, “Seller, I want to make sure that you have got all your questions answered and you feel good about this. Do you want to call your CPA and ask some questions? You don’t have a CPA? Do you want to call my CPA and ask some questions? I want to make sure you know what you’re doing.” That’s part of the nature of being a good direct-to-seller type of buyer. You give them the opportunities to check with the outside resources to feel good about what they’re doing, especially on a complicated potential topic like that. 

I love your verbiage around a lot of this stuff. It’s a great demonstration of what talking to somebody to help solve their problems looks like. I’m looking forward to our conversation in EXTRA because we’re going to be talking about this Y.E.S.S.E.S Framework. Could you tell us a little bit more about what that deep dive is going to look like? 

I’m going to talk about how the Y.E.S.S.E.S Framework applies to intentionally source deals that you can buy with seller financing to hold for the long term. There are a few key strategies I’ll share in there about how we’re not shopping for a property. We’re shopping for a person. That’s one thing we’ll talk about. The idea of seller financing is that you buy your financing when you buy the property. That is a very different mentality by itself. We’re not going to talk about that. Overall, we’ll talk about if you want to buy properties with seller financing. It’s critical to start with the end in mind and reverse-engineer the whole marketing process so that from the very first step, it’s all about finding those people for whom seller financing would be an excellent solution. Their Y.E.S.S.E.S Framework will be our step-by-step process for discussing those strategies. 

Can you tell everybody how they can reach you? 

If you look up The Thoughtful Real Estate, that’s who we are, ThoughtfulRE.com. We have a Facebook group called Rental Portfolio Wealth Builders. We’d love to have anybody join us there to talk about this specific way of doing acquisition for investment real estate. 

I know that you’ve got a gift for my ladies. Let’s talk about that. 

I am putting together a download that is called the Three Ways Women Can Have a Real Competitive Advantage in Real Estate Investing as Thoughtful Real Estate Entrepreneurs. These are my thoughts, reflections, and experiences. When you take a look at what it means to be a thoughtful real estate entrepreneur, women are well-suited naturally to be great with those skills. I hope that’s very encouraging to your audience. I wish that I saw more women in my own communities trying to do these things. They’ve got so much potential. If someone wants to get that, they can go to ThoughtfulRE.com/bliss. It will be very easy to download that special guide. 

Ladies, Jeff and I were having this conversation. He’s putting together a gift, especially for you and this show. One of the things I’d like to talk about in this download is empathy. It’s funny because I have never thought of myself as an empathetic person and yet he was like, “Really?” You noticed that as human beings, we take for granted our gifts. We don’t notice them. It’s nice to have someone to shine a light on what your strengths are and what you should be highlighting in a way that maybe you can’t see. Maybe you’re blind to it. I love getting this different perspective. 

Women all have ideas of what we’re good at. It’s fun to hear from the other side like, “What do men do? What do they look at?” Then say, Women are good at that thing. I wish I was better at that. I need to learn that. That’s a skill that they know and take for granted. I need to develop that.” I know that Jeff, Based on the conversation that we’ve had, I know that Jeff is going to give us some good ideas about what our strengths are and what we can amplify, utilize and value in ourselves. 

It’s such an important point. We can’t help but undervalue the things that come naturally to us. We don’t even necessarily realize they’re gifts. I’m going to try to point some of those things out and see how they can be aimed at being a great real estate entrepreneur. 

Thank you for that. Jeff, are you ready for our three Rapid-fire questions? 

I’m ready. 

Tell us one super tip on getting started investing in real estate. 

Here’s what I would recommend. Maybe this is not common advice. Instead of thinking about, “I want to buy a property. What is available for sale?” I would say, “Everything is available for sale.” I don’t mean, “Everything is for sale at the right price.” I mean, “Everything is available when there’s a relationship. Here’s what I would like you to do. I would like you to go into your town and identify ten properties that you would like to own, “It sure would be awesome to be the next owner of that property. Maybe I see potential or think it’s beautiful. You love it, that’s all that matters. Grab a pen and a stack of paper. Sit down and write a simple, nice handwritten letter and send it to the owner of that property. 

Don’t say, “I’ll make you an offer of thisI’ve got the cash. I can close quickly.” It’s none of that stuff. Say, “Hi, this is my name. I see your property all the time. Frankly, I love it. If you would ever consider selling it, would you please let me be somebody who could talk to you about that? Hold onto my letter for whenever the time is right. I hope to hear from you.” Send that handwritten letter ten times. Chances are your phone will ring whether it’s immediately or not too much time. That is a great practice. It’s emblematic of overall what we need to be doing more and more as real estate entrepreneurs. 

I have to ask a question. If someone doesn’t respond, do you write it again and again to the same person? 

Yes. I’d say send it 3 or 4 times a year. Every 3 or 4 months, write another letter to the person. Make it seasonal if you want to. Don’t photocopy and send exactly the same thing. What I used to do is I would go sit in my car in the neighborhoods where these properties were. I would write the letters by hand so that I was soaking up the environment of where these properties were. You could do that. If you ever get to go to a coffee shop again, you go sit down in the coffee shop and do it. 

What is one strategy for being successful in real estate investing? 

It is very much what we have talked about in the broad sense, which is to take a people-oriented approach to real estate. It’s people who sell properties. It’s not properties that sell themselves. I saw in a Facebook group that somebody said, “I’ve identified 3 or 4 properties on the market that would be good for seller financing.” I had to comment, “I appreciate your enthusiasm but properties aren’t candidates for seller financing. People are candidates for seller financing.” Take a people-oriented approach. Don’t be afraid to talk directly with people who own properties. Don’t be afraid of saying the wrong thing, screwing it up, or overcommitting yourself. Get comfortable with the idea of talking. Practice talking directly to people who own properties. Good things will come of that one way or the other. 

What would you say is one daily practice that contributes to your personal success? 

I’ve been trying to think of a catchy way for this to be articulated, but you know how they say, “An apple a day keeps the doctor away.” This is a work in progress, “A handwritten thank you card a day keeps the poverty away?” I’m still working on the last part. One of the best things you could do would be to go online or go to your local office supply store, buy a giant box of thank you cards, get a bunch of stamps and have that pen sitting there. Every time I meet with a seller in person, maybe a potential lender or a regular person, I always send a handwritten thank you card. Sometimes people comment about that, but even if they don’t comment about it, just the fact that you did it says so much about you and shapes the way they perceive you in a very positive way. It’s very difficult to send too many handwritten thank you cards. If you send one a day, that’s a great rhythm that you can get into and it’s not a difficult habit. 

It’s also like your own personal gratitude practice in a way. Jeff, this has been amazing. I loved this portion of the show. Thank you so much for all that you’ve shared. 

REW 55 Jeff Stephens | Off-Market Acquisition

Off-Market Acquisition: If you don’t have the empathy to be able to understand the other person, whatever proposal or offer you put in front of them is going to be a version of a shot in the dark.


Thank you. I appreciate the opportunity to share this perspective. I know I’m the oddball in the world of real estate investing. This is not how most people do it, but I’m cautiously optimistic that the more people who hear this message will go, “That would be authentic for me too.” I hope some of your readers can have that light-bulb moment. 

Ladies, thank you so much for joining Jeff and me for this portion of the show. We have more in EXTRA. We’re going to be talking about his Y.E.S.S.E.S Framework. I always say, “Say yes because it’s so much more fun than no. He’s got a six-step process that he’s going to be talking about. We’re going to be doing that in EXTRA. If you’re not subscribed but would like to be, go to RealEstateInvestingForWomenEXTRA.com, and you get the first seven days for free. You can check it out. I appreciate you. I look forward to seeing you next time. Until then, remember, goals without action are just dreams, so get out there, take action, and create the life your heart deeply desires. I’ll see you soon. Bye. 


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About Jeff Stephens

REW 55 Jeff Stephens | Off-Market AcquisitionJeff loves delivering presentations to great organizations!  In his first entrepreneurial career, he was a paid speaker at banking and credit union conferences all over the US and Canada, and even spoke at a marketing conference in Latvia, Lithuania and Estonia.

Today, Jeff speaks to groups of entrepreneurs and real estate professionals.




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Social Tightening While Social Distancing With Thom Singer

REW 3 | Social Tightening


We think of social distancing as a necessary health protocol now that we are facing a pandemic, but the term can be misleading when it comes to human relationships. As we are all forced to physically distance from each other, the need for social connection – for “social tightening”– becomes all the more acute. Author, podcast host, content creator and growth leadership speaker, Thom Singer coined this term to remind people that we need to have to connect with the people in our lives, now more than ever. In this conversation with Moneeka Sawyer, Thom explains the epidemic of loneliness that has been going on ever since before the pandemic, how physical distancing has been exacerbating it, and how we can take action and make the effort to have real interactions beyond social media likes and blanket emails.

Listen to the podcast here


Social Tightening While Social Distancing With Thom Singer

I am excited to welcome to the show my friend, Thom Singer. He is an advisor to executives, a speaker, and a content creator. After a successful career in sales and marketing, he became a growth leadership speaker in 2009. A decade later, he has brought his high energy presentations and action-oriented content to over 950 audiences. He is the author of twelve books and is the host of two podcasts, The Cool Things Entrepreneurs Do, which I have been on and the Digital Enterprise Society Podcast. On these shows, he has interviewed over 550 business leaders and others with a focus on discovering how the most successful people get farther across the gap between potential and results. He and his wife make their home in Austin, Texas, and are the parents of two highly spirited daughters. Thom, how are you?

I am great because I’m here on your show.

We had so much fun on your show. I can’t wait to see what happens here. Ladies, one of the things I wanted to tell you about Thom is he is a very compassionate person. He’s very business-focused, but he brings compassion in his heart to the business. He’s got this blog that he writes and it’s on ThomSinger.com. He writes these amazing articles about how to stay connected, how to bring your heart to business as well as a lot of different topics. One of the articles that he wrote one day, and I loved it, was about a term he’s coined called Social Tightening. With what everybody is going through with the Coronavirus, I wanted to talk specifically about that and how we can help our relationships to thrive and fill our hearts back up if we’re feeling lonely. Thom, talked to me a little bit about social tightening. Let’s start by defining it.

This term, social distancing started coming up on all the newscasts and all the articles that you read because this was going to be the way that we were going to flatten the curve and be able to stop this virus. Some people were stepping up going, “Social distancing doesn’t right. It’s physical distancing. People need to keep socially connected.” I started calling it social tightening as you social distance or as you physically distance. Long before this started, going back many years, there’s been an epidemic of loneliness that has been under the radar in our society.

A gentleman by the name of Dr. Vivek Murthy, who was the nineteenth surgeon general under President Barack Obama, when he was doing research and going out and talking to people about this big opioid crisis that we face in the country, an underlying thing he discovered was this whole epidemic of loneliness. He wrote an article for the Harvard Business Review. It spoke to me because I go out and teach people how to connect, but there are always people at conferences who don’t feel connected to that conference, to their coworkers, etc. Long before we had to stay at home, there were already 20% of our population felt lonely. I got concerned that this is going to get worse however long we have to do this.

We were at the airport down in San Diego after the New Media Summit. When you’re at a conference, one of the things that you talk about is this whole idea of social media versus networking. Could you tell me a little bit about what you told me then? That is so impacted me.

I think that we have forgotten over the last decade that a link, a share, or follow does not equal a human relationship. Just because you’re connected to someone on Twitter, doesn’t mean they ever log on and look at anything you say, it used to be. I talked to a person who worked in technology years ago and he said, “Email is a best-effort communication tool. Just because I send you an email, I don’t know if it got there. I don’t know if you ever read it. Even if you open it, I don’t know if you read it.” As much as we rely on email, it’s always stuck on me that it’s only a best-effort communication tool. Social media then came in, and everybody’s broadcasting everything. Everything is on Twitter. They’re going live to all their friends and they’re putting up fancy pictures of them making Kardashian faces or whatever.

The problem is that once I put something on Facebook or whatever medium, I assume that everyone who knows me has seen it, but there are two problems. That person may have paid no attention or the algorithm of LinkedIn, Facebook, Twitter decides who sees what we post. It’s only 10% of the people who follow you. A couple of years ago, before the algorithms had even taken over, I was talking to a friend of mine from high school and I said to her, “How’s Lisa,” who is her best friend from high school. She went, “Thanks for asking. She goes into this whole thing.” I was like, “What are you talking about?” “Lisa’s dead. She had been killed in a hiking accident three weeks earlier.” I was like, “I had no idea.” She went, “It was all over social media.”

I had been on a European vacation and didn’t check Facebook for two weeks. When I had logged on, it had all died down amongst all of our friends. I never knew. Nobody ever thought to call, to email, or text because it was put on Facebook. That was years ago. I learned right away that that is worse than a best-effort communication. That’s a crap communication. We think that social media is networking, but we have no idea if it’s landing with anybody as opposed to if you’re face-to-face and we have a conversation in the bar. I’m pretty sure you heard me if we’re standing there. We can’t treat them as the same thing. We have to get back to this whole idea of personal interaction with people, whether it’s digital or live. My motto through this whole Corona crisis has been, “More personal/less broadcast.”

Let’s talk specifically about social tightening. What that means and what are some strategies we can use to get closer?

While we’re living in this era, it’s going to be with us for a while. Now, we’re all on lockdown, but soon it might be partial lockdown. We’re working from home. Let’s look at coworkers. There’s office culture. There are things that happen. Billy always takes the big coffee mug. They aren’t happening, but that also means that we’re not having real interactions. We need to make an effort. We have to be intentional of where we are putting our intention and attention when it comes to the people in our lives. With coworkers, there’s probably a team meeting where everybody’s on Zoom and they might be a Slack channel or a group email, but that doesn’t mean that Mary Lou and I are having a conversation. We need to take a little bit of time to reach out one-to-one to our coworkers.

The same thing is true with our friends, with our extended family. The same thing is true with our clients. How many newsletters have you gotten in your email inbox since the Coronavirus started? Mine has gone up unscientifically by five times. I get 100 newsletters a day, where people are telling me to check the CDC website and wash my hands. That’s great, but my local pet store didn’t need to be the one to tell me that. We’re having all of this broadcast and everybody thinks, “What’s important to people COVID, so that is the title.”

Maybe if my doctor or if the White House sent me something, but I don’t need that from my accounting firm. We need to broadcast less, especially about things we’re not experts about and have one-to-one communication, which means you’re going to have to take the time to send an individual email, an individual text, make a phone call, reach people, and leave a message. Whatever that says, “Moneeka, I was thinking about you and your show is such a delight for everybody as we’re going through these rough times. It brings bliss to people. Thanks for doing that.” That’s personal. If I send an email to every podcaster I know and go, “Keep up the good work. Podcast like crazy,” you probably won’t even open it much less understand that I was saying, “You’re an important part of this solution.”

As you said those two things, one of them made my eyes well up with tears and gratitude and the other one was, “Yes, I heard that.” It is an emotional reaction. I don’t know if you felt what that difference was like, but it’s true. My email box has ballooned from 1,000 emails a day to 3,000 emails a day.

During this crisis, we need to make an effort at having real interactions with the people in our lives. Click To Tweet

It is 3 to 5 times more is what’s happening.

I can’t keep up with it all. It is so much more as falling through the cracks. I feel like I’m working harder, feeling less satisfied. There’s this weird thing. Instead of being part of the problem, which it is now, it becomes part of the solution. Make someone’s email box, inbox their friend again. Whether you do email or not, and I’m not encouraging that, I love the idea of doing texting, personal phone calls, even to leave a message. On Facebook, you can do Messenger. You can still direct message all of them on Facebook, on Instagram, LinkedIn, whatever you’re using. You can do personal stuff. I am getting personal stuff there.

I did get a message on Instagram as to what you said, Thom. They’re like, “Thank goodness that you’ve pivoted and done a little bit more about Bliss. We need that.” It was good feedback for me and it keeps me going and it keeps juiced. What can we do for each other? You’re taking a look at the whole balance of it because you’re business-focused. In our families, with our friends and in business, how can we pivot with all of those people? You gave us all an exercise while we were at the New Media Summit. Can you tell us about that? I’ve been doing it. You told us to send five personal messages a day.

I’ve narrowed it down since then to three because five freaks people out. I’ve been telling everybody to reach out every single day to three people because there’s a thing called the Dunbar curve. Some of your readers may have learned of it. It was a series of research done many years ago and people have tried to dispute it. I don’t care if somebody thinks, “That’s been disproven.” The concept of it is awesome and that is we can only have about 150 people who were friendly with. You have your inner circle of about five. You then have maybe your friends that are about fifteen, but your community can only be about 150 people. Where if I were to say their name, you would be able to tell me who their children are and where their children went to school, etc.

The argument has been made over the last years and that’s been expanded. Social media allows it to be bigger. I had somebody say, “My extended community is 30,000.” That’s crap. If it is, then you’re the outlier. Using 150 people who can be in your circle of friends and associates, and they took this back to ancient times. Villages used to be about 150 people. When the village would get larger, it would split in half. Some people would move away because it gets too big to handle. Your personal brain is wired for about 150 people. I don’t care if you’re in sales, if you have online courses, or if you have a podcast, you might have a mailing list with 5,000 or 50,000 or more people on it, but you don’t know who those people are.

During this crisis, blanket mailing people you don’t know isn’t what those people need. I don’t care how brilliant you think you are. They don’t need another newsletter from you. However, the 150 people who know you, know your kids’ names, not because they’ve heard you say it on a show. Because they’ve had dinner at your home or your paying clients or past clients, you’re a coach, the people you used to coach who you were part of their life for a year on that monthly call. Those people probably need to hear from you. If you narrow it down to, “Who are my 150?” You could follow up with all of them every month by doing 3 to 5 a day.

In 30 days, that could be 150.

Some people might say, “My list is smaller.” Some people list is bigger, then put a little thing, who are my 150 favorite people? Those are the people who need to hear from you and to get that email saying, “I was thinking about you and I care.” Those are the people who are going to say, “Wow.” A lot of people scrape emails from the National Speakers Association and they think they’re so smart because they’ll email like, “I have this product I sell to speakers.” We all go into back-channel talk going. “Does anybody hear from this?” “I never heard from him before.” “I got the same email now.” We know when it’s a random thing trying to sound personal. You scraped my email off a website, I get it.

However, if I know you or you’re one of my college fraternity brothers and you reach out and say, “I realized that the speaking and meetings business has been hit harder. I was thinking about that. You’re my only friend as a professional speaker. My heart goes out to you. I hope your family’s okay.” Am I going to stop and feel as a human? Yes and that happened. The fraternity brother I haven’t talked to in years said I was reading something about what’s happened to the meetings industry. “You make your living speaking. I had never thought about that. You’re the only person I know who makes their living that way. I want you to know I care.” That’s what we need more of.

It’s because there is a way in the old world. When we didn’t have so much contact with each other, through social media, email, and all of that stuff, we used to write letters. We used to send each other notes. When the phone came along, we used to make phone calls. A lot of that has gone away for a lot of reasons. Part of it is we’re overwhelmed with all the things that we’re supposed to be doing and that’s expected of us socially. The other piece is we’ve also got comfortable not having to do those things. Some of the things that I’m loving it. I’m getting personal cards from people with pretty pictures that make me feel good, the phone calls, and the texts. These sorts of things, “Moneeka, I was thinking about you.”

The handwritten note is valuable. Imagine if a client’s got a handwritten note that said, “I want you to know that I’m here for you when the world returns to normal.” It is not trying to sell anything, just helping and checking in. Helping and checking in is the new selling. If you want to be remembered when the economy comes back, don’t be cramming down by my coaching program. I have been doing that, but I want to go back to something you said because it’s a perfect analogy. Let’s go back 15, 20 years before we had email and before everything was a broadcast. We used to have broadcast companies like CBS and NBC and the radio stations. Humans had to be personal because we couldn’t broadcast to everybody, but there was one-way people did use to broadcast and that was The Christmas Letter.

You will get a Christmas card and somebody had typed out a letter, “Dear blank,” and they would handwrite your name into it. They then would photocopy both sides, maybe with some clip art of a Santa Claus and a tree. They would go through and they would broadcast their year. “We were so fortunate. We went to the Grand Canyon. My husband won the trip to Hawaii and we got to go there. Our room had a view of the diamond bed.” Who loved getting Christmas letters? Not very many people because they weren’t personal. They never talked about your true life. It would say like, “This year, my son Johnny found a way to get free lodging.” That translated to Johnny’s in prison, but nobody ever wrote that Johnny was in prison and they flowered it up. Johnny’s got free lodging for 3 to 5.

I still do get Christmas letters. It is rare. I get three a year. What’s comical about that is, in the old days, I used to be like, “I felt like I was reading a report.” I had to read everybody’s stories so that I could keep up with everybody. It felt like an obligation.

It is a form of novelty, that handwritten note that says, “Hey.” Even if it’s a typed email that says something personal, I can tell if something is cut and paste. I was at a conference one time and while on the plane, I was sitting with a bunch of people from the conference and all of us got emails at once that said, “Dear insert name,” The mail merge didn’t work. They sent a 1,000 people a note addressed to dear insert name. In the middle of it, it said, “As you know, insert a name.” They had too many mail merges to make it sound personal and all it did was prove that it wasn’t personal at all because the mail merge failed. Let’s go back to the real thing, “Dear Moneeka, it was so much fun to be with you in San Diego, sharing the cab to the airport and having dinner together before our flights. I laughed so hard. I hope we can stay in touch.” It means so much more than some mass-produced broadcast.

REW 3 | Social Tightening

Social Tightening: Long before COVID-19 forced us to stay at home, 20% of our population was already feeling lonely.


It is like, “It is nice to meet you at the New Media Summit. You were light in the room. I look forward to keeping in touch.”

I got to paste that to everybody.

I got about 50 of them.

You were the light in the room, maybe all of those were personal. I got them too. I thought I was the light in the room.

I am jealous. I have to share the stage with you. That’s such good tips. Let’s talk a little bit about some connecting inside our homes. This is what’s happening. We’re all stuck together. We look at each other and initially, we’re like, “I get all this time with you. This is amazing.” By now, we’re like, “Could you go to another room?”

There is a woman who posted a meme that says, “This man is the love of my life. I now want to kill him.”

It doesn’t mean that we all love each other. It’s just we’re wanting to get back to our more normal rhythm, but because we’re in the same space, that does not mean we’re connecting. Let’s talk about how to connect and how to disconnect? How to create the space and then how to create the love? It’s like a dance where we have to create this wave in and out. Talk a little bit about that.

I am talking from personal experience. I have two daughters. One of them is out of college and engaged to be married and lives in Chicago. She and her fiancé were supposed to be married on May 16. That date has been changed, thanks to Coronavirus. Their wedding is temporarily postponed. In addition to spending fourteen months of their lives planning a dream wedding, they are sequestered in a 700 square foot apartment in a high-rise where there are no common areas open. You have to stay in your own apartment and a city there in Chicago on full lockdown. My future son-in-law, his job has moved home. He has an important job and he’s working 8 to 10 hours a day. My daughter has to stay out of his way because he’s got to use this brain for what he’s working on. He’s a mathematician.

She has got 100 square feet to hide and her job has been canceled. One of the things we did is every week, we’ve been having a Zoom dinner with them. We open up a Zoom room. They come in, they make dinner. We are ready at 6:30 and the five of us sit down and have dinner together. That has been a great way to keep in touch with extended family. In fact, I’m wondering why we haven’t done this forever. We get to have a meal. We, as humans, we love to break bread and we’re able to talk and laugh. My wife, my younger daughter, and my son-in-law say, “It’s just like dinner around the table because my oldest daughter and I are big talkers and they can’t get a word in edgewise.”

They said, “It’s like being in a restaurant with you. Thom and Jackie are stealing the conversation.” I’m not sure I’m proud of that, but that’s what they said. It was real is the point within our mini-society here inside the house. With our eighteen-year-old, I have a high school senior. I have commented that at least she likes her parents because we are on lockdown, but my wife and I are very different. We both still have some semblances of jobs we have to run. We both work for ourselves. We’re not sure how much money we’re making, but we’ve got things to do, but we operate differently. I go into my office. She has her office. She has taken to wearing headphones and listening to music or a book on tape when she’s not working. If she doesn’t want me to be like, “I thought that, that, that.” I’m much more of an extrovert and she is much more of an introvert.

We’ve agreed if she needs introvert time, were headphones and music, or whatever because otherwise, I’ll come in and start going, “Guess what I just read online.” We’ve set up that parameter, but being an extrovert, I can’t go forever without human contact. I’ve been hosting a happy hour in my Zoom room. I’ve been inviting people to come, get their beverage of choice, and log on with me in Zoom. I’ve been hosting anywhere from 8 to 12 people. I do a little bit of standup comedy and so in Austin, I’ve been hosting the only ongoing virtual open mic night for the local comics. I get about eighteen people for an hour and a half every Tuesday night. What’s funny is a lot of them are young and single and live alone. They stay after it’s over. They’re like, “Do we have to hang up?”

Yes, I’m a grownup who wants to go to bed now because it is 10:30, but it’s just doing that. Within my daughter and my wife, we’ve sat down and had dinner together every night. We make dinner. I guess once we had a restaurant catered in, but every night we make dinner and everybody comes and sits at the table. Even if it’s twenty minutes, we have that human connection time. I think the long answer to your question, there’s a lot of ways to do it, but you have to have some structure and you have to appreciate, “She’s an extrovert. She needs to be left alone.” “He’s an introvert. He needs some human interaction, even if it’s his friends online.” “She’s eighteen. What a nightmare to be stuck with your parents for months.”

There is compassion for what everybody is going through. I have trouble with this and I’ve had to pay attention to this is dinner time with David. We used to go out to dinner. We created that as a pattern because when we would get home, he was interested in looking at the mail and I knew that there was all this cleaning that needed to do. There was all this stuff that distracted us. We started just going out to dinner every night, which was great.

That doesn’t sound bougie at all. We hit all the restaurants in Northern California. Only Sunday through Saturday.

Building relationships, both personally and professionally, doesn't happen by accident. You have to be intentional about it. Click To Tweet

I am grateful for the life I’m allowed to live.

I was going to add in, when you don’t have to send two children to super bougie colleges, you can eat it as many restaurants as you want. I bet you and David couldn’t outspend the cost in decades of educating two children.

We are like it in what we’re able to do. We’re noticing it, and believe you and me. Where I was headed with this is that we’re at home, we have dinner time, and we are very committed to eating together. We’re both tempted to poke at the phones. We’re tempted to run over and do something in the kitchen or attempted to turn over the laundry. There are all these things. We have to force ourselves to sit down, even if we have nothing to say because we’re both exhausted from the day and be together.

It is funny because the first couple of weeks we were like, “This is so much fun. There was so much to talk about.” The next week, it was like, “Hey.” We’re starting to get back into that old world, like having a conversation over dinner when we didn’t have everything on our phone. Everything interesting was not on our phones. We found each other interesting. We are doing that again. It’s just funny how we evolve and to set expectations on how we’re going to connect. Sometimes people think, “Connections should be organic and fluid.”

If we left it to organic and fluid, then a lot of people would never find the business success that they find. Networking and building relationships that matter, both personally and professionally, doesn’t happen by accident. I speak at a lot of conferences and there’s a lot of meeting planners that say, “What are you doing to encourage great connections?” People come to conferences for two reasons. Remember when we used to go to conferences, people used to go into a ballroom, but the thing is sometimes meeting planners are like, “We’ve got a sponsor for an open bar.” Booze is not a network.

That is not a social lubricant like we think it is. In order to do this, you have to learn the number one thing I teach people is you ask other people questions and then listen when they talk. I know that sounds shocking, but it does. Within your family, we establish this years ago when the cell phone, the smartphone first came out and that was no phones at the table. Whether we’re in a restaurant or we’re in our house, no screens at the table have been a family motto. I’ll be honest, we’ve been a little bit lax because we are around each other all day. At dinner, if somebody was to pick up a phone, we probably wouldn’t go, “No screens at the table.”

No screens mean just no phones, no iPods, no laptops, no TV, nothing.

We’ve had the TV on during dinner more than usual, but it is a new rule. My 23 years old was commenting that we were letting the eighteen-year-old have a glass of wine. She’s like, “That’s different rules than when I was a high school senior.” I was like, “Coronavirus.”

The main point is to understand that it’s not just that in business that we have to pay attention to building relationships, in our personal lives, we do too. It’s more important than ever because we’re spending so much time together. We are spending time together does not mean connection. It’s not quality time necessarily. Most of the time, it’s just time. We need to figure out how to have that quality interaction within our own homes, in our environment so that we can stay connected. Otherwise, what will happen is that you’re going to be surrounded by all these people that you love and you’re going to go back to feeling lonely, separated, and isolated.

You feel lonely in a group. It happens all the time.

It is because people aren’t connecting.

The other thing we have to do is realize different people are going through different things. As a person who travels 100-plus nights a year, being home for months on end, there’s like this, “I’m going a little bit stir crazy.” Whereas my wife, who’s a pretty serious introvert. Having me gone 100-nights a year is causing her to go a little bit stir crazy because I’m right there. I don’t pick up after myself the way it wouldn’t happen if I was gone. I think you have to take into effect, how is this affecting her? Not just me. We also have a high school senior. The news is not covering this well enough. There’s a couple of little stories here and there about brides getting married on their iPad, socially distance from their fiance.

My daughter and her fiancé chose to postpone until the fall, which hopefully it will happen then, but they’re not covering these major life events like weddings, high school graduations, and college graduations. There are many major life events that are being swept under the rug. I don’t think as a society, we’re giving them enough attention. In our house, I’ve tried to ask my daughter, “How are you feeling about this? How are you about this?” She got accepted into her first-choice college. She has a Facebook group with some other students who are new.

She has this community and it’s been a little exciting. She’s making some new friends there, they’re doing some Skype, and some Zoom and stuff like that, but I’m like, “How do you feel at school doesn’t start in the fall?” Her answer was, “We’re not talking about that yet. We’re not going there.” These are things that I don’t think as a society, we’re doing a good enough job of saying, “I have to work from home. My speaking events are canceled. My income is cut to nothing.” There’s a lot of that being covered out there, but there’s not a lot about, what about these people who have nonmonetary major life events? How are we honoring these people? I don’t know that we’re doing a good job of it.

REW 3 | Social Tightening

Social Tightening: You can feel lonely in a group. It happens all the time.


I don’t know if you know this, but I have two sets of my show. There’s the free show, which is this piece and then we’ve got EXTRA. There’s another article I want to talk to you about an extra. We’re going to finish the show in a moment, but I’m going to spring this on you and let my audience know what’s coming next.

I love things that are extra.

In EXTRA, I want to talk about the article that you wrote and I’ll admit, I haven’t read it, but it is about if you’re wealthy, how to be compassionate for those who are not. I’m excited about that topic. We’ll talk about that next, but first, let everybody know how they can get in touch with you and hear more of your amazing advice.

ThomSinger.com or Thom Singer on all the social media.

Thank you, Thom. This conversation has been wonderful. It’s filled me up. Thank you so much for joining us. Ladies, thank you for joining Thom and me for this portion of the show. If you are subscribed to EXTRA stay tuned. We’ve got more. If you’re not, please do go sign up at RealEstateInvestingForWomenExtra.com. If you’re leaving us, thank you so much for joining us. I look forward to seeing you on the next show. Until then, remember, bliss is your birthright. Choose to live your bliss every single day. I’ll see you next time. Bye.


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About Thom Singer

Thom Singer is an advisor to executives, a speaker and content creator. After a successful career in sales and marketing, he became a growth leadership speaker in 2009. A decade later he has brought his high energy presentations and action-oriented content to over 950 audiences.

He is the author of 12 books and is the host of two podcasts, “Cool Things Entrepreneurs Do”  and “The Digital Enterprise Society Podcast”.  On these shows he has interviewed over 550 business leaders and others with a focus on discovering how the most successful people get farther across the gap between potential and results.

He and his wife make their home in Austin, Texas and are the parents of two highly-spirited daughters.

We talk about what Thom calls Social tightening…it’s important, no matter whether we are social distancing, networking, or building a business, to remember that we always need to stay connected.  Thom gives us some great ideas on how we can do that effectively and lovingly.


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