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About Richard Strayer:

A college physics drop out who found his way to a temporary and entry level position at Countrywide Home Loans in the default space, finishing up a degree in the evenings, before spending a 3-year tour with KPMG and becoming a CPA.

Ultimately returning home to the Mortgage Business, he spent his formative years in the loan boarding, acquisition, and subservicing space.  During the Great Recession he moved into the non-default operations where he has been for the last 15 years.


In this episode Jason and Richard discuss:

  • Leadership starts with connection 
  • Connecting in a hybrid workspace 
  • The layers of “why” 
  • You are the CEO of You, Inc. 


Key Takeaways: 

  • Leadership starts with connecting to each person in a personal way so that you can hear their story and understand them on a deeper level. Make yourself available and be sincere. 
  • There is no replacement for face-to-face interaction. Even if you work in a completely remote environment, you’ve got to try to meet sometimes in person in order to create a connection. 
  • If you want to truly be able to connect and understand a person’s idea, you’ve got to be open, be curious, and keep asking questions. 
  • You are the CEO of You, Inc. Do everything for your own life what you would have done for your business. Have accountability, create systems, be organized, and continuously plan your own growth, always looking ahead to the next level.


“Connect with each person in a very personal way, so that you can understand them and they can understand you. Make yourself available.” - Richard Strayer

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Connect with Steve and Jason:



Show notes by Podcastologist: Justine Talla


Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.




Listen to the podcast here


Putting People First: Connecting And Having Productive Conversations With Richard Strayer

I've got a special guest, Richard Strayer. Richard, welcome to the show.

I'm glad to be here.

We're excited about you. When I got your booking information, I went, did all my research, and saw PennyMac, Cal State, CPA, and all kinds of things. We talked about a few things. One of the things that you mentioned is you had tuned in to our show. You know the first question that I'm going to ask you is not going to be about your background, your career, or the amazing insights that you have for our audience. What are you grateful for?

It's funny you should ask because I forgot that you asked that every single time. What I'm grateful for is living in this great country we have. It's not a perfect country. We're noisy and boisterous. Democracy is entertaining at times but it's the best country for me and many people. I love living here. I'm happy about it.

Thanks for that answer. Sometimes when we read the headlines and all the stuff that's going on, our heads are about that but I appreciate you bringing that to the forefront because me, too. That's what I would say to that. We live in an amazing time in history and what I believe to be one of the most amazing places in the world. Thanks for bringing that up.

I would like to get to your background though. As I was reading the notes, there are things that I highlighted about changing courses mid-college and maybe even some things there. Would you mind telling us the story of your career so our audience knows? I do this when I listen to podcasts. Almost metaphorically, my arms are crossed. I'm like, "Who is this person? Why am I even listening to them?" Who are you? Why are you on the show?

I'm born and bred in California. I started as a Physics major in college. I dropped out of school and figured out what's the best degree out there. I went the accounting route to get a business background. It has a good launching point. I worked at KPMG for a few years and then ended up at Countrywide for a few years. Countrywide was bought by Bank of America.

Eventually, I ended up at PennyMac years ago. It feels like yesterday but we have gone through a lot of things in that time. We had a lot of ups and downs. It feels like I've only been in the industry for a few years but then you start adding up the numbers and putting them out there. It has been a few years. We have gone through a number of cycles mostly in the servicing space. I'm happy that I've gone through it. I'm looking to see which way I turn next and what's the next challenge for each and every one of us.

There are some iterations there. When you say, "I've been here eight years," in some arenas, that sounds like a long time but it's longer than eight years ago when the mortgage meltdown and everything happened. In my brain sometimes, I'm like, "That's when a lot of people's careers and paths took a different path," but you've taken a different path even since then. That's a long time. You serve in a leadership role.

I'm in the servicing space at PennyMac in the non-default space, overseeing much of the work that's not the default work, foreclosure, and bankruptcy and managing the routine even though it's far from a routine most of the time. In the last few years, the digitization of the process and the automation of it has been key while looking to get those efficiencies because our revenue stream doesn't change dramatically. It's a job of continuing to figure out and employ different strategies to get better efficiencies organizationally.

I'm always interested in cutting-edge stuff. When you say new efficiencies, technologies, and things, do you have anything that you're particularly excited about in that arena?

There are so many things. I listen to a lot of podcasts. I've listened to yours a bunch of times and many others. I'm always looking at crazy ideas for the future. Many of them don't apply for a mortgage but I'm seeing how you can take that and implement it. I get lots of sales calls in the last few years about machine learning.

People like to say the word and they don't have machine learning or AI in their process but I'm figuring out how that applies to how we can better scientifically design our processes to make sure that the processes are efficient and most importantly, that they're good for the customer. I'm making sure the customer has an interface that is helpful and intuitive for them. We don't have the big budgets of Google. How do we do that on a shoestring budget to make it work for all of us?

I was listening to a pitch from somebody that's doing some neat stuff with technology to help the industry be more transparent and more consumer-friendly. I'm helping a group sell some different properties these days. I've been in this industry for almost 30 years. There's still so much that is not transparent that happens. People don't fully understand it. If technology can help bring some of that to the forefront for the consumer, I feel like everybody benefits.

We have millions of loans. Many servicers have millions or even hundreds of thousands of loans. We talk about efficiencies. We all want to design a very linear process where we do every single widget the same way. Henry Ford said, "You can get any color you want as long as it's black." Realistically, in the last few years, we're trying to figure out how we can provide the service in the media or the vertical that the customer wants. That's a challenge sometimes. How do you do it differently and stay within your regulatory compliance? How do you meet the customer where they want to be met, whether that's on their phone or by mail?

We're having this big shift away from mail. Who goes to their mailbox every day? Most of us don't but for some, all they rely on is the mail. You have to figure out how you can get to the right people. You have the cool term omnichannel, figuring out how it is but how do you communicate to people in a way that doesn't get lost in the churn? Even emails or texts, if you sign up for any one of those, people get hundreds of them. Even there, you can get lost. How do you address it? Maybe they don't have to call it all but if they do need to contact you, it's the way they want and as efficiently as possible.

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People First: Omnichannel allows you to communicate to people in different ways. But you must make sure your message doesn’t get lost in the churn.


When you say the word omnichannel, for those that might not be familiar with that, what exactly does that mean?

Omni means multi. It's a cool way to sound cool when you say multiple channels.

You did sound cool when you said it.

I brought it out of the book that I read last time about cool words to say on shows. Frequently, omnichannel is more often used as it relates to sales. How are you going to get to someone from the servicing space? You're talking about emails, phone calls, letters, different channels, and things that can get through to get to whatever source you're trying to get to.

Figuring out the way that the consumer wants to be communicated with and efficiently making that happen is what you're saying.

Honestly, we work with 20,000 tax agencies in the country. We work with I don't know how many insurance companies. You have all these different connections with them. You would love to say, "We can get one feed from all of them in the same format." That doesn't happen, so you try to figure out how you can connect both directions in a way that works for everybody.

Let's go back to leadership. How long have you been in the leadership position since you've been in the industry?

Let's say twenty-something years. I'm there pretty consistently for 22.

Within that timeframe, I'm sure you got a story or two and some lessons. There were some things that stood out to me when you were filling out some information for the show from a leadership standpoint, things that you've noticed, things that you've experienced, and things that you've learned. What tidbits stick out to you in those twenty-some-odd years from a leadership standpoint?

It's people first. It's connecting with people. As you connect with people, each person is their individual person. You hear it but you have to live it, understand it, and connect with each person in a very personal way so that you can understand them and they can understand you. It sounds like the opposite of honesty is dishonesty but there are a lot of people who shells when they talk to people. They don't necessarily connect. If you're truly sincere and open, listen and make yourself available. That opens up the doors.

As you connect with people, you get to know them in a personal way. You can understand them and they can understand you.


It doesn't mean you're going to agree on everything but that allows you that emotional bank account with those folks to make mistakes yourself or have them make mistakes and understand each other. Get out of your office, walk around, stop at people's desks, and make them a little less efficient but make sure you connect with them out there, whether it's sports, cooking, ballet, or whatever they might be interested in. You're going to have something that you have in common with pretty much everybody in your office or anyone you interact with. It's important to find that because it greases the wheel of your conversation and make sure that you have productive conversations.

When you say, "Get out of your office and walk around," it makes me think about the old management books on management by walking around. You described exactly what that is. I have to ask the question that is going to be on the readers' minds. That sounds great. There's so much remote work these days. How do you navigate that? There have to be some answers to that. How do you do that?

COVID was difficult. It still is. We're mostly back in the office but we have some hybrid. We have some folks that permanently work from home. There truly is a challenge if you never meet them face-to-face to have that connection. You can try a bunch of things. Maybe I'm too old but I don't have the perfect answer for a 100% work-from-home environment.

If you're hybrid or in the office, you're going to have that human connection out there. I don't know if 100% work from home is a viable long-term method for processes that are routine but if you go back and look at salespeople for 20 or 30 years, they wanted to get face-to-face conversations with people. They could talk with them and interact with them. They're much more fluent in working with a human than I am.

They're built to go out there and interact. They still realize that you can't replace face-to-face interactions. We have to understand that there are things that I'm sure we will learn. My daughter who's in her early twenties has grown up on a lot of streaming platforms and meeting people online. They might have the answer. They might be able to figure it out better but I still think their friends meet face-to-face. There will always be some element of it.

Graphics - Caption 2 - TII 150

People First: Salespeople of the last three decades still want to get face-to-face conversations with people. This cannot be replaced by a work-from-home setup.


I so appreciate that answer because of your transparency, "I don't know if I have all the answers," but what you do know is what you ended up there with, which is you cannot replace face-to-face interactions. You see it with humans. I don't care if it's a sales situation or a social situation. When two people meet and interact, whether that's first virtually, on the phone, or something other than face-to-face, the closer that relationship gets, at some point in time, they're going to be face-to-face if not often. That's the ultimate relationship when we are face-to-face interacting with one another with body language, tonality, and all the other things that go along with that. Thank you for that.

That all came from you saying, "People first." One of the other things that you said in your answer was this piece about learning. Before we hit record, you mentioned that word as well. You mentioned dropping out of school but then getting your CPA. You're leading people and observing as you're leading. When the word learning comes up from a leadership aspect, what exactly does that mean to you?

It means about 5, 6, 7, or 10 different meanings to it. There's learning how to interact with people. There's tech learning. You have to learn systems, technologies, and things like that. It's a mindset. It's a process. Maybe it goes back to my being a physics major at school originally. You want to understand how it all works together and the laws of the item that you're working with. If you understand the elements, you can adjust them and move them. If you don't understand it, you're putting something in a black box and seeing what comes out the other side. You have to understand.

There's a thing that I tell people at work because sometimes I come into a meeting, and someone is trying to explain something. I ask why, and they probably can answer the first question but then I have another question on that. People need to ask why once, twice, or three times at least because generally, your first answer is not fully answering the question. It leads back to a question that comes before it and another question before that. Ask a lot of questions.

Going back to learning and talking to people, I try to give people the heads up, "I'm going to probably ask you a lot of questions." If it's their first time interacting with me, it doesn't mean I don't believe them and I don't understand but I'm going to ask why because I need to understand the process so I can put it back together, put it back in my head, and then understand why and how it works.

That learning happens at work all the time. It happens on a daily basis. You end up at a store. You're waiting in line. Many of us do that. You're like, "Something is not going right at the store. Why am I problem-solving Best Buy's operational issues while I'm in here?" You do, and you don't say anything. Maybe when I get older, I'll tell them how to do their job. You do that. You try to get out and move on.

The layers of why is something that I hope our readers don't miss. You are making me think of a story. This happens to be a sales situation but it was exactly the scenario that you outlined. I read a book on sales. It asked me to go six layers deep with the why question in a sales scenario. I was a mortgage banker at the time. I had one of the top realtors that I was fortunate enough to get face-to-face with. I was like, "Here's the deal. I'm going to try this technique out." If it bombs and if it doesn't work at all, they're already not doing business with me, so it doesn't matter.

I asked, "What's important about real estate to you?" He gave a topical answer. I said, "Tell me why that's important to you." In my head, I was counting, "1, 2." I was going to get to six. We might have ended up where he was like, "This is crap. What are we doing here?" I asked why that was important. On number five, he looked me straight in the eye and said, "The only other answer that I have is love." He explained what that meant to him. We did so much business over the next five years.

It was one of those things. That was a sales example. That's not why you gave the example because it was leadership but it's the same thing with leadership. Tying it back to what you initially said about people first, I want to hear you expand on it. I didn't hear you asking why because you're trying to needle somebody or have a personal whatever. It's more like, "I want to understand." The more that you understand either the thing or the widget but more importantly, the person, now you've got some juice. I would love to hear you expand on that. That's what I'm taking from it.

It's a person's standpoint. If you understand why or where someone is coming from, you could ask the simple, "Why were you late?" It gets to one answer. If you try to understand what their true situation is, you're going to be able to help solve their problem if someone is looking for a promotion or money. The more you understand why they're driving for it. Is it because they want to get to the top? Where do they want to go? They are all the same type of questions.

If you know where someone is coming from, you can help them solve their problems, no matter if they are looking for money or a promotion.


The more you understand it, the more advice you can give them. It's honest advice, "We have a great job here for you. You should stay. Here are your opportunities over the next year. You want to get to this point. We probably don't have that opportunity here for you. It's going to take a lot longer than you would want." It's trying to drive into what's driving that individual. It's why and caring if they realize you're not just going to give them an answer to keep them and you believe in it. I've had folks that have left organizations I've been in and come back some in weeks, some in months, and some in years.

I don't fight. I don't say, "You're leaving. You're never going to come back here again." It's because of giving them honest advice. I even told someone not to come back, "You need to stick it out. This will be beneficial if you can stick it out." That helps and builds a relationship that goes much deeper than work. It's much deeper than this project or the task for this week or this year. It connects you in a way that your relationship is real. It's still a work relationship but it's a real work relationship.

That ties back to what you initially said about people first. I appreciate that. You believe deeply in taking control of your career. You gave an analogy before of the train conductor and that type of thing. I would love to hear you riff a little bit on taking control either through some stories of your experience or people that you've observed. What can you tell us about that?

Maybe I'll start with one of the pet peeves that I tell people about. What is available for me here? It's in the job. Turn that around. You're the CEO of Jason Inc. at this company. You can be one person. There might be opportunities but what would you do as Jason Inc.? It's everything you would do for a business. Do your SWOT analysis. What are my Strengths, Weaknesses, Opportunities, and Threats? You're in charge. I'm your boss. I'm not in charge of your career. I'm a leader in this organization. I'm not in charge of your career. You're in charge of your career.

People have to understand that if people are giving them feedback, "I'm one of your customers at Jason Inc. out there. If I'm telling you I don't like it, maybe I'm wrong. Maybe I'm a bad leader and I'm giving you bad advice," but you now have to take that in and say, "Am I a feedback point? All your other feedback points are awesome. You can disregard it. That's consistent with other feedback I'm getting from other people. Maybe I do need to redirect it." Ultimately, if you're Jason Inc. inside of a company, and you decide that everyone there doesn't like you and you think you have a good product, sometimes you have to take it to a different market.

There are all these different things that you can take and figure out how you can work. You can't put blame on the organization. As a leader, it might be my fault. I could be making a mistake but if you are dealing with me, you have to manage your little company inside accordingly. You have to market your company, improve your company, and know there are lots of competitors out there. You might have been the best person in the organization years ago but five more people have shown up, and they might be better. Now, you're the sixth best in class.

This Jason Inc., Richard Inc., or whatever-your-name-is Inc., what I'm hearing from you, Richard, is self-accountability, taking control of the SWOT analysis piece, and being real with yourself. I've always observed this. There is a mentality of, "It's not up to me. It's the customer, the company, the man, or the government." Take responsibility for yourself. I'm almost empowered from listening to you. If it is to be, it's up to me.

Your ownership of your career and life is not just a work thing. You have all this stuff that goes on in life. There's the whole idea, "You're lucky." Luck plays some part but a lot of preparation gives you more luck. It gets you prepared when there's an opportunity. A lot of luck is built and developed. You will always have good luck and bad luck in your life but the more you're prepared when you're in the muck of a situation, the more you're positive going, "I know what the plan is. I have to walk that way out of here." It goes with the 7 Habits comment, "Think with the end in mind wherever you're at."

Graphics - Caption 3 - TII 150

People First: Luck plays some part in your success, but preparation gives you more luck. The more you’re prepared in the muck of a situation, the more you can walk your way out of it.


"What am I trying to get to? Where do I want to get in life?" I quote 7 Habits a lot in life. If you don't know where you're going, you don't know which way to walk. You walk into a meeting, "What am I trying to achieve in this meeting? Am I here to say what I want to say? What do I want out of the meeting?" That will help you redirect what you're trying to get in the meeting.

It's a very small utilization of the process but if you're trying to achieve an outcome and you haven't said a word, and you can already tell the outcome is going to happen, you can sit on your hands and shut up, and it will happen. I've seen lots of people coming out of a meeting. It's going to work out perfectly for them. They decide they still have to say they're better. They're not going to get value. They end up going sideways for what they say.

One of the most important lessons I still have to continue to learn is what you touched on. Sometimes the best thing is to shut up, whether that's in a meeting, in a sales situation, or with our kids or partners. There are times when it is in our best interest to shut up but it's a lot easier said than done.

I feel like I'm good at thinking and shutting up. Sometimes at home, it's a lot harder maybe because you're relaxed. You're a little bit more at the moment, "Why did I say that? There was no value. They didn't progress anything I was trying to do. Next thing I know, I have to dig out."

That may be one of the best takeaways. We have all probably heard some version of that lesson in the past. You and I converse. If that's your takeaway, "Is it best for me to be speaking?" and if you even have an inkling of the question, the answer is probably no. As we wind down our time, is there anything that I haven't asked you that you want to make sure gets said before we finish?

Maybe two things. One is on leadership. In books, all of it is common sense. I don't leave every leadership book I've ever read going, "I never knew that. I never understood it." It takes some very common sense things and puts them into a framework that you can remember. Maybe more importantly, you can talk to someone about it. If you're a big fan of organizations, it's reading and understanding a book or a topic so that it's a framework for a conversation so that in every conversation you have, you don't have to go into a long diatribe on something you already know.

We are all providing value in this world. We should treat each other as equals.


Think with the end in mind when you go into that meeting. If you're all on the same page already, it's a fairly quick way to have a conversation but it's all very common sense at the basis. The other thing about leadership, in general, is I'm a believer that we're all equal. That sounds pretty basic but I find a lot of leaders in organizations, "I'm this. I'm that. You need to do this or that."

Whether you're the guy picking up the trash in the alley, the President of the US, or anywhere in between, we're all providing value to this world. We should treat each other like we're equal. I don't always see that. It's something that I would love everyone to do. It's to sit there and go, "I'm going to treat you as I would treat my spouse or my friend and not treat you as you've only been in this organization for three days, or you're the janitor. You're all people." Treat them equally.

That's such a great lesson to end on. I appreciate that. I've taken notes the entire time we have been talking but those last two items are gold. Thank you for that. Richard Strayer from California, you did it. That was so good. I appreciate you taking the time. I appreciate you investing in the show and then also investing in others. I'm super grateful. We started with what you're grateful for. We will end with what I'm grateful for. It's this time and your insights there. Thank you so much, Richard. I hope we connect again soon.

Thanks, Jason. Have a great day.


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