Barry Jenkins – Too Nice for Sales

Barry Jenkins runs one of the most successful real estate teams in America in Virginia Beach, VA. He is also the author of the Amazon Bestselling book “Too Nice for Sales”. He spends his day with a dual focus on his team and as the Head Realtor in Residence at the innovative digital marketing firm Ylopo. Click here to learn more about Barry.

Show Notes

Welcome to the Agents Who Crush It In Real Estate podcast where you’ll hear the good, the bad and the ugly of how real estate agents overcame challenges and grew their business. Check out the Episode Notes at Here’s your host, Lindsay Favazza.

Lindsay Favazza: Hello and welcome to another exciting episode of the Agents Who Crush It in Real Estate podcast. I am your host, Lindsay Favazza. Today we have a very special guest who exemplifies what it means to truly crush it in real estate. Joining us is none other than Barry Jenkins, a seasoned real estate professional, a dynamic team leader, an inspiring coach, and an innovative trainer.

Barry’s journey in real estate began at the age of 18 and has spanned almost two decades, marking him as a veteran in the industry. He’s not just any realtor, he’s a visionary who has led his team at Better Homes and Gardens in Virginia Beach to incredible heights. Barry’s impact extends beyond just sales. He’s a best-selling author of Too Nice for Sales, a book that has revolutionized how nice people can excel in sales. As the head realtor-in-residence at the digital marketing firm, Ylopo, Barry has also been instrumental in training and product development, sharing his wealth of knowledge with others in the field.

Today we’re going to dive deep into Barry’s journey, his strategies, and his insights, which have made him a standout figure in real estate. Say hello, Barry, and welcome to the podcast.

Barry Jenkins: I am super excited to be here and honored to be in an environment of people that crush it. That’s such a fantastic topic for a podcast. Excited to be here.

Lindsay: You definitely do that, so we had to have you on. I know I was talking to Dave, who is our VP of sales who I know is close with you, and he was like, “You have to have Barry on.” I’m like, “Oh my God, of course we have to have Barry on.” I’m so glad it all worked out and so quickly too, so thank you for that.

Barry: Absolutely.

Lindsay: Take us back to two decades ago when you signed up to be a real estate agent at 18. Why is that? Why were you so motivated at such a young age to get into this field? Do you have any regrets about starting so early?

Barry: No, no regrets. I was managing a shoe store at night and busing tables for lunch. I had someone that had access to a lot of cash that said, “Look, you’re hustling. I see you putting a lot of effort at 18. Have you ever thought about investing in real estate?” I said, “No.” They said, “Well, look, if you find a property, we’ll do a $100,000 line of credit with a balloon payment at the end of 12 months. You can buy it, flip it, and sell it.” I did not know what I didn’t know, and I just did it like a typical 18-year-old kid.

Lindsay: It sounded really good.

Barry: It did, but I didn’t know what could go wrong. Nothing did go wrong, but I just wasn’t aware of the gravity, I just did it. I took the opportunity, I made $26,000 in six months, and I never looked back. For the next six months, I bought a property for myself, I moved into it. That’s when I got my real estate license. I was in college. I never stopped going to college, but it really took the wonder out of college because I’m learning marketing and management courses, and I just knew that wasn’t going to be the track that I was going. I finished it, but I wasn’t all about it.

I got my real estate license. I did fine just because from 2001 through 2007, it was so easy. You stick a sign in the yard, you’d get eight or nine leads. Digital marketing wasn’t as popular as it is now, so it was really easy. 2008 completely crushed me, though. It wrecked me financially because the market changed, and I thought just by being diligent and consistent and doing the same things that I always did, that there was wisdom there. I guess in some ways there was, but I never changed, and so I only made $1,000 that year.

That journey from 2008 through 2010, that really is what made the book. 2011 is when I made my first million dollars as a result of the suffering of 2008 to 2010. It really was that two-and-a-half-year period that changed my life forever.

Lindsay: You said that in the beginning, you didn’t know what you didn’t know, and you were getting into real estate blindly in a way not knowing what the risks were. It sounds like when those risks came, you were that much more blindsided by the whole thing, which I’m sure a lot of realtors at that time were. You said it was easy. It reminds me of the last few years where it’s like you put a sign on the ground and it’s just going to sell magically.

We just went through that again, and maybe now is the time for a lot of realtors who started then that are now getting that wake-up call. It’s very interesting that you say that you were this green, didn’t know what you should be afraid of in a way, and then all of a sudden it just hit you. Tell me about those years, those two years. What got you through? Why did you stick with it?

Barry: 2008 to 2009, we lived off of credit cards, basically. I racked up, I think, maybe $60,000 in just groceries and gas. I had my equity lines cut off because the housing market shifted so quickly. It was just really hard. I talk a little bit about this in one or two of the chapters in the book, but I got a couple of sales jobs to support my real estate habit. One was selling steel buildings over the phone, which taught me my phone skills, and then another was life insurance. Convincing people that they’re going to die and they should buy this piece of paper to protect their family is just a tough gig. Anybody who’s good at it, God bless them.

Basically, I did real estate part-time and paid my bills through those other sales jobs. It was those years that taught me all about sales. It taught me what was wrong with sales. I didn’t feel good about myself at the end of the day. Creating false urgency, tricking people into closing, specifically with the steel building industry, that was a really popular thing. That really is where I got my chops. Once 2011 came, I realized that I had a new opportunity, and that was REOs. That provided me with a chance to do what I loved again.

I gave it all that I had, and the result of that period is I now pivot quickly because there’s been many. From 2011 to 2023, there’s been many micro shifts. None as dramatic as 2008, but the reason why my business has continued to grow and thrive through all of these shifts and ups and downs is because I’m paying attention, and I pivot quickly when I see there’s a shift. Now it’s more like a game than anything else.

Lindsay: You feel like a little cat and mouse.

Barry: Yes. You just have to recognize. I remember when COVID, everything shut down for three months. We were still considered an essential service, but everybody in my market just hunkered down. We just didn’t know what to do. I remember the sales meeting was Zoom. Zoom wasn’t a verb at that point. It wasn’t as popular. I told my agents, I said, “Look, I hope this all ends in a week,” I said, “but this feels 2008. As a result, everybody download Facebook Messenger on their app. When you meet a lead that wants to go look at a home, I want you to friend request them. I want you to do video-showing tours through Facebook Messenger.”

We crushed it that year. Obliterated our goals, made tons of money, and it was because we were paying attention and we adapted quickly. That’s the name of the game in any business, not just real estate. I do think real estate tends to be a little bit more challenging as far as watching the trends and knowing how to pivot and all that stuff.

Lindsay: When did the transition to having a team start? Was that before 2008 or did you do that after 2008?

Barry: That was as a result of 2011 because I had struggled through 2009 and 2010 with these other gigs, doing part-time. 2011, I had a shot. I had a real chance to do something different. I think I sold maybe 50 REOs. As a result of the REOs, I produced an additional 75 transactions. In 2011, I did 125 transactions by myself. No staff, no assistant, no transaction coordinator. I was excited and miserable. 70-80-hour work weeks are really hard to maintain when you’re trying to be a devoted father. I remember the moment. I was the number one agent in my market, and I was so excited at the Realtor Awards. They had the screen and there was that five seconds where it finally showed number one agent. For five seconds, I was elated. Sorry, we’re going to have to edit this. I just turned my AI on with my hand gestures.

Lindsay: Oh, no. That’s okay.

Barry: I was elated during those five seconds, but then it ended. Nobody’s really paying attention. As a result of that, I said, “That’s not worth it.” Being number one didn’t satisfy me, I’m going to have to figure out how to pour into others. Serendipitously, right around the same time, I had three old friends from high school reach out and say, “Hey, I see you’re crushing it. I’m in the food service industry.” “Hey, I’m an appraiser.” “Hey, I’m a contractor. Would you teach me what you’re doing? I would love to learn the business.”

Those three agents are what started the team.

That journey of building a team, mentoring agents has been a very hard one. My next book, I’m about halfway through with it, it’s called Too Nice for Leadership. The subtitle is a compendium of all my screw-ups because basically, I’ve got two decades of screwing up as a leader, and that’s what’s made me the leader I am today. Running the team has definitely been a learning experience. We’re up to about 80 agents now.

Lindsay: What do you think is the most fruitful and the most rewarding thing about having a team? I can assume I know what the answer is to that, but then what has been the biggest challenge or the biggest mistake, I guess, that you made?

Barry: Selfishly, I really value freedom. When people say, “Do you enjoy money?” Yes, because I enjoy freedom. For me, running a team and empowering others to be successful is gratifying because I’m watching their lives change. If I’m being transparent with you, I do it because it provides me with a better quality of life. I have a teacher’s heart. I really enjoy enlightening and empowering others. It doesn’t matter the subject.

I’m not married to real estate. Real estate has allowed me to produce a tremendous career, and now I’ve got agents that need me. They still have a direct access to my calendar where they can book one-on-ones with me and I’m empowering them. The most challenging part, I am not good at hiring people because I see the possibilities. I see what they could become, I don’t see who they are. I think the most challenging thing for me is leading them to water, so to speak, and watching them not drink. I call that out a lot.

I tell them in group settings that, “Look, some of you are going to lie to yourself and say, this isn’t for me. I tried real estate and it didn’t work. I want you to know it’s because you didn’t do the work. Don’t just die on the vine quietly over three to four months, just be emotionally aware and honest with yourself that you’re not giving this your all. If you decide to leave, you didn’t leave because it’s real estate, you left because you didn’t want to do the work.” I have found that 60% end up doing the work and 40% don’t. That’s normally the numbers. We grow off of those 60%.

Lindsay: That’s the thing, you give them that little word of wisdom, which seems probably like, “Okay. Yes, I get it, Barry.” I’m sure you get that every once in a while. They’re like, “All right, I’ll put in the work,” but then, it’s so true because if they do put in the work, you know that something’s going to come of it. Once something comes of it, that’s when they become addicted to that feeling, and they know it works and now they’re going to take off.

We see it all the time with agents within our training system and then also agents within the company. It’s like you know what they’re capable of, it literally– Tell me if I’m wrong, but in the eight to nine years that I’ve been in this business now, I look at it and I see someone come into our trainings or a new agent in the company, and I look at them and I think, “Wow, they’re going to be really good,” and then they end up not.

Or there’s someone that I’m like, “There’s no chance they’re making it in this business,” and then all of a sudden, they’re the number one agent in their office. It’s so crazy. There’s not a certain type of person. You can literally be anybody, but the bottom line is putting in that work and believing in yourself and not giving up.

Barry: I would say the persona of agent that thrives on my team is the agent that typically gets left off in a room of superstars. I need people that will just listen and execute. It might not be pretty candidly. They might not sound great, they might not have the look of your typical rock star, they might not have the car, but they do the work the way that I teach them. I’m looking for people that are hungry enough to do the work and experienced enough to see the opportunity I’m providing them.

The last year of my life, I’ve really gotten into therapy and learning about feelings. Feelings suck. It’s much easier as a man to disassociate from them completely, but there’s moments in your life where you realize, and so I’m trying to impart that to my agents, and I’m thinking– I can hear one of my agents in one of the calling rooms next to me right now. He’s brand new, he’s 18. Before he made his dials a week ago, I texted him and said, “Look, before you make your calls, I want you to call me.”

He said, “I’m getting ready to make my calls.” I had a two-minute conversation with him. I said, “You’re going to call 100 people today and 80 of them aren’t going to answer. 20 of them that do, 18 of those 20 are likely going to tell you to leave you alone. You’re only going to find two. I want you to know that if you find two out of those 100 attempts, you are going to have a thriving and successful business as a real estate agent.” He called me later that day and said, “Barry, I got hung up on more times in my entire life, but I found three people that want me to send them information.” That made my heart sing because it reframed what could have been a really discouraging experience, and I love that for him.

Lindsay: That’s awesome. Let’s shift gears for a second. You’re talking about having a team and writing now two books soon. You’re talking about being a dad. I know you just have so many different hats that you wear. From an agent’s perspective, which is mainly the audience here, how do you stretch yourself so thin, but then be so great at all of these different things? Then from a team leader perspective, how do you make sure that the team feels like they’re getting the most from you without spending all your time babying them in a way?

Barry: It’s a great question. I would tell you that it’s been an evolution over the last eight years. Let me speak to those single agents that think that this isn’t relevant for them. You’re probably doing everything, you’ve gotten to the degree of success that you have because you’re different, you care more than other agents, and that’s what makes it hard to find help. Let’s be honest, no assistant is going to ever care as much as you do about your business and because of that, you’re holding on to all the details.

I want to tell you emphatically that you have to let go to grow. It doesn’t mean you don’t care, it doesn’t mean that you’ve let go of your business. It means you understand that your greatest value is doing the things that only you can do. I have learned over the last eight years that the slower and the more intentional and more methodical that I am with my time, the more money I make, the more success I enjoy, and the more peace that I’m able to have in my home and my life.

When you say yes to something, by default, you’re saying no to something else. If you say yes to a three o’clock appointment with person A, you’re saying no to a three o’clock appointment with person B. Choose wisely. If you take what you want to make per year, like let’s say you want to make $100,000, and you divide the 40 hours in a week over 52 weeks, I think that’s like– I don’t remember. I’m going to make up the number, but let’s just say it’s $130 an hour. Let’s say that’s $130 an hour times 40. I know my math’s wrong, but just hear me out for the example.

If it’s below $130, you need to start thinking about hiring someone. My first assistant was in 2012 and I was so scared. Oh my gosh, I was so scared. She was $10 an hour, and I was sitting outside of REOs to wait for the power to come on. I hired her and I said, “If I can sell one house paying her $100 a week as a result of that time–” I sold two that month, and I never looked back. Within four months, my assistant had an assistant because I bought into the fact that I was accelerating my income by having people do things that were below my pay grade.

I never stopped doing things that way. I haven’t stopped. You guys hear me saying I’m doing all these things, I say no to a lot more. I also have a full-time job at Ylopo, that’s a full-time gig. I’ve got lots of full-times, but I somehow make it home for dinner every night.

Lindsay: That’s amazing. Congratulations because it is a hard thing to learn, but you’ve done it very well.

Barry: Thank you.

Lindsay: Another shift gear here is I want to hear the craziest, obviously, that you can tell, but what’s your craziest real estate story? What is something that’s happened that you’re like, “Oh, this is a doozy.”? What’s that story you tell at the dinner party?

Barry: I helped a first-time buyer buy a home in a neighborhood with a high crime rate. Five years after she bought it, she was relocating to Texas. She asked me to list it for her. I listed it for sale, someone from my church that I was going to contacted me about the house that I listed. Now I’m representing both sides. They understood what that meant, the implications, legal perspective. I had a Chevy Impala, and we had the home inspection. Found a couple of issues, nothing major. I had aviators on and in a high crime rate area, everybody left and my car wouldn’t start.

I’m waiting for the tow truck company to come, and I noticed a townhouse in front of me had four visitors stop, walk up to the front door, shake hands slowly, get back out, get back in their car. I was like, “Hmm. Looks like a business transaction. Not really sure.” About an hour and a half later, a woman walks out of that front of that house, walks up to my door with a 45, very large pistol, 45 caliber pistol, and she says, “Are you the police?” I don’t know what possessed me to do this, I really don’t, but I started laughing. I said, “I can’t believe you rolled up on me with a 45 caliber gun and asked me if I’m the police. No, I’m not the police. Here’s my business card. You can check my website.”

Still to this day, I don’t know, but I didn’t really have any options. My car wouldn’t start. Maybe 10 minutes later, I’m like, “Please start [unintelligible 00:22:01]” She left. She said, “Okay, I believe you.” I’m like-

Lindsay: What was she going to do if you said yes?

Barry: I don’t know. My car did start 10 minutes after.

Lindsay: Thank God.

Barry: Calls me and says, “I thought you said your car didn’t start.” I said, “It finally did,” and I was getting out of there.

Lindsay: You scared the crap out of me and I [unintelligible 00:22:23] there.

Barry: Now I’ve got a situation because I represent both sides and I just have-

Lindsay: You can’t go back to that house.

Barry: No, I did still go back, but I represent the buyer and someone walked up to me with a gun. I got with an attorney because I’m like, “What the heck do I do? Who do I tell what and when? How do I disclose this?” At the end of the day, I made proper disclosure. I referenced the event, I encouraged the buyer to check crime rates and just shared my experience without any anecdotes. I had to be really careful. They ended up buying it anyway, but a year or two later, they sent me a picture of bullet holes in the side of their house. I was really glad that I made proper disclosure, but it was a really intricate, convoluted scenario to be in.

Lindsay: Can you imagine if you got that text after not doing that? Do you know what I mean? Your heart would have sank knowing that you had known that there was something. You absolutely did the right thing.

Barry: Doing the right thing normally is hard in the moment and rarely do you regret it later on.

Lindsay: Absolutely. Wow, that is crazy. I’ve heard some doozies, but that’s up there. the Impala with the aviators, you were asking for that.

Barry: I was. It was a cool aviator too.

Lindsay: I know, right?

Barry: Cool Impala. It was a good car, but yes-

Lindsay: What year was this?

Barry: I want to say 2011, 2012.

Lindsay: Was it an old-school Impala too?

Barry: No, no, no. It was the new one. I don’t know how that works. I don’t know if police officers get the new ones or what, but it was a newer– It wasn’t the cool round one, it was-

Lindsay: The older one, yes. As soon as you said an Impala, I had a flash. The name Gladys came in my head because my brother had an old-school one with the loud engine and all of that. We named her Gladys. I immediately was like, “Oh, you had Gladys.”


Barry: That’s funny.

Lindsay: We only have a few minutes left. I want to make sure I give you a chance to talk about the book because I know Dave has said nothing but great things to me about it, I know it’s off to such a great start. How long ago did you release the book?

Barry: I would say almost two years. It’s almost been two years.

Lindsay: It’s been out for a little while.

Barry: It has. The first year it did okay, but I didn’t advertise it. It’s a self-help book.

Lindsay: Takes a while.

Barry: Then year two, something clicked. Guys like Dave and other broker-owners across the country, after they read it, they started buying boxes of them and giving them to their new agents. Now I think we’re over 25,000 copies sold. It stays in the top 10, top 20 on Amazon for real estate sales. Looking back, I think the feedback that I’ve got from it, that’s part of why it’s made a success. I write like I talk, so very standard. I didn’t learn what a noun was until I was in my 20s. It’s hilarious that I even wrote a book.

It’s just stories, and the stories are designed to help people recognize that as nice people, we get off these sales calls without trying to close, without going for the appointment, without trying to overcome objections, and we think, “I’m so glad I’m not pushy.” What I really try to help people understand is that they’ve actually become very selfish on those calls. They’re more worried about their need to feel approved of and accepted, which are legitimate needs, but think about burdening these strangers on the phone, trying to get these strangers to like us.

They’re leads, but they’re strangers. We’re talking about things, just trying to get them to like us. It has nothing to do with the lead, it’s all about us and our need to feel successful and approved of. When a nice person recognizes that they’ve been selfish, and they recognize that the most compassionate thing that they could do is challenge someone’s thinking when they say they’re waiting a year, to not just say, “Okay, I’ll call you in a year.” Say, “I think that’s fantastic that you’re planning ahead. How did you decide on a year?”

You hear the person on the other end of the phone struggle through that answer, and you’re able to say, “It sounds like you’re trying to figure it out. We should be meeting to go over this. This is the largest financial transaction of your life.” You recognize that you can come from this place of sincere service, compassion, and you can crush it to use your show’s phrase in this industry. You don’t have to be the hardcore closer.

There’s two ways to do this, either you’re going to be calloused and decide, I don’t care, buy or die. I’m going to, I’m going to close the sale or I’m going to get off the phone and move to the next one, that’s one door. Those guys do fine. Those guys and girls do fine, but the people that do it the way that I’m teaching, they outlast and outpace them 10:1 because the person you have to become to not care, it screws up the rest of your life, but if you can stay in this position of passionately serving people around you, you actually become a better human, that means you’re going to run a marathon instead of a sprint.

Lindsay: With referrals. A whole huge part of long-term sustainable success in this business is repeat business. It’s like that other turn and burn is not going to get you that repeat business. I love that.

Barry: Thank you.

Lindsay: We will make sure to put a link in the show notes so that people can go on Amazon and get that book. Make sure to follow Barry. We have all of his stuff. I always go to point and I never point in the right spot, but there you go. Make sure to follow him, reach out to him. He’s a wealth of knowledge and such a nice human being. It was so great to talk to you today, Barry. Thank you so much.

Barry: Yes.

Lindsay: Awesome. Thank you guys all so much for listening, and we’ll see you on the next episode of the Agents Who Crush It in Real Estate podcast. Thanks so much.

Thanks for joining us on the Agents Who Crush It In Real Estate podcast. We hope you’ve learned some valuable takeaways. Be sure to take action and grow your business. You can check out the Episode Notes and more content from the show at And if you’d like this episode, and you’d like to hear more stories, please share with others, post on social media or leave a rating or review. To catch all the latest from Anthony you can follow him on Instagram at Crush It In Real Estate on Facebook and YouTube. Thanks again and we’ll see you next time.