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About David Hrobon

David Hrobon is a principal with more than 35 years’ experience in mortgage banking. One of the most recognized and respected veterans of the industry, David’s specialties include strategic management, mergers and acquisitions, organizational redesign, loan operations and process and performance management.  He has held sales, sales management, ops management, corporate support positions and senior and executive leadership roles over the course of his career.  


David began his mortgage career in 1985 and worked for a combination of independent and bank-owned lenders of varied sizes, most recently serving as Chairman and CEO of Wintrust Mortgage. Under David’s leadership, Wintrust Mortgage grew from a mid-sized independent lender in 2004 to the 8th largest bank-owned retail lender nationwide in 2020. 


Throughout his 17-year tenure at Wintrust, David was an active buyer of independent mortgage companies and leveraged six separate retail acquisitions to help address internal strategic objectives, giving him experience and insights into related due-diligence, contract negotiation, buyer and seller motivations and fears, evaluation of origination platform models and cultural alignment, as well as effective methods to transition and onboard acquired employees. 


A graduate of Ohio Wesleyan University, David earned a bachelor’s degree in economics. He also attended postgraduate classes at the University of Chicago, The Ohio State University, and the University of Dayton.



In this episode Steve and David discuss:

  • How negativity impacts creativity 
  • Mastering the basics 
  • The need for a “why”
  • Tackling difficult tasks 


Key Takeaways: 

  • A mind that is focused on negative things or filled with stress hormones is not conducive to generating creative ideas or solutions. 
  • Be humble enough to start over and always remember the basics and fundamentals. The things that you’ve learned will get you to where you want to be. 
  • You need vision in order to continue moving forward. Be clear about what you want and reflect on why you want it. Anyone who has a “why'' can bear almost any “how”. 
  • Create a realistic and measurable plan and write it down. Share it with somebody to encourage accountability. In tackling difficult things, you need to be surrounded by positive reinforcement. Surround yourself with people and things that encourage you. Eliminate or slow down drifts of negativity. 


“Any road will get you there, but you need to know which road you’re on. You need to know exactly what it is you want to change, you want to improve, or you want to accomplish and why.” - David Hrobon



Connect with David Hrobon:



Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking 



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


Understanding The Importance Of Why With David Hrobon

I am welcoming you to our series that we have titled The What If We Series. You will and have read some of these already. I have a guest. David Hrobon is with me and I am excited. A quick description of this as many of you are acutely aware, it's a little bit of a challenging time in the industry. Jason and I are over here at Rewire, we were recognizing the fact that when we get into seasons like this, people of all kinds have a tendency to accentuate, point out, talk about, think about, read about and focus on all the stuff that's gone wrong with the world.

We're going to do something a little bit different and we're not going to talk about that. We're going to specifically focus on the stuff that's going well, that's going right, the hope that we have and the things that we can specifically do in this season because we want to be a different voice out there.

Before you think, “Steve, some of those things like margin compression and rates go the other way and all these things about the economy and inflation.” I sometimes wonder, David, if people are going, “Steve and his guests know that that stuff is real.” We are aware of it. The intent of The What If We Series is not to ignore that, be pollyannaish and be whimsically hopeful and ignore reality. In our work, we never ignore reality. Instead, the focus is to look forward and say, “Notwithstanding what is real, there's still so much good happening and good things that we can do.”

The guests that are in The What If We Series are people whom we believe are experts at that, both the reality piece and the what if we piece. What If We is our attempt to do a little bit of brainstorming. That's probably more intro, David, than I normally do because I love bringing in the guests right away.

I guess the last thing I'll say is we're calling this The What If We Series because what if we represent a level of thinking that we are in need of doing some pretty cool problem-solving? In our work, one of the things that we study in neuroscience is you get into neurochemistry and there are all kinds of positive neurochemicals that we know of. Dopamine, serotonin, oxytocin, endorphins and these positive chemicals. There's one chemical that we've studied a lot and it's cortisol, which is also known as the stress hormone. I don't want to focus too much on that but there's a lot of cortisol out there, David.

There's a lot of stress and anxiety. Our hope for our time, you and I, is that when people read this, not only can they get some ideas from us about where we're going, what we're doing, what the hope is and what positive things we can do because that's where I'm going to go with you but as we do that and the readers read, when we're thinking like that, we are in the midst of reducing and releasing some cortisol. Here's the deal. When cortisol is present, our prefrontal cortex, that part of our brain that uses logic, language, reason and creativity is hindered.

We want to bring that back because this is what we need in this season to navigate us through stuff. We need a relaxed, poised, calm, thoughtful brain so that we can come and go, “What if we did this and that?” Hence, The What If We Series hit there. That's a much longer preamble than I do normally with our guests. Sorry for that. I hope that's, at least, enlightening for our What If We Series.

I certainly thought it was terrific and it’s very helpful for me. You gave me about eight seconds of that in the invite. My brain has been flying here since you started talking with all sorts of thoughts so thank you for that.

I don't usually list out the desired result for our call but one of them is people are going to know that you and I have a deep friendship and we go back in business for quite a ways. Beyond that, my hope is that people who read this not only know your what if we’s as we talk about them but they walk away and go, “How am I doing that what if we? How am I doing that with my team?”

If all we're doing is sitting around pointing out the obvious and festering and focusing on what's bad and negative, it's simply not generative. It lacks creativity. I don't want to go into this too much but I want you to think about this for a second. I don't want to say impossible because that might be hyperbole but how difficult it is to hold the concept of creativity and being generative and stress and anxiety at the same. If I'm super stressed out and someone says, “Go get creative,” good luck.

Let me tell people about David Hrobon. I love any name that starts with HR. That's good in my book because that's the coolest thing of all time. I always want to ask, how bad has that been butchered in your life? We can have a whole episode on that probably. My friend David Hrobon is a leader in the mortgage industry and has been in that industry for many years.

The list of companies that he has led and been a part of is extensive all the way back to Sears Mortgage. He started in the mid-'80s. In 2004, he joined Wintrust Mortgage in Chicago and ended up being the CEO of that company. I met David and I won't date us but it was in the early 2000s. You were part of a leadership group. What I would love to tell our audience is that in that leadership group, 15 to 20 CEOs were sitting around tables for a couple of days. I remember Hrobon being the EF Hutton of that group. A lot of people shared a lot of things and there were a lot of intelligent people in that group.

I always found you to be a super thoughtful person so much so even in that group. When you began to give statistics and thoughtfulness to what you were doing and what you were saying, I watched people sit up in their chairs and stuff. It is a true honor to have you on the show. David, in a different chapter of his life, joined the Stratmor Group, which is the premier statistical thoughtfulness for the mortgage industry with regard to all the ways that you want to dissect and pick apart how the industry is doing.

A few years back, they also got involved in mergers and acquisitions. David is a leader there at the Stratmor Group. We are in the presence of somebody I believe who can speak eloquently, not just to the mortgage business but business in general. I've heard him speak many times. I'm excited to have you on the show, David.

What a humbling intro, Steve. It's funny when you were talking about me being so thoughtful and insightful. It's ironic that as I was listening to your intro, I was thinking to myself about a book that I had read back in the '80s by a guy named Robert Fulghum. The book that he wrote, as you may recall, was All I Really Need To Know I Learned In Kindergarten. It's a terrific book but one that has incredible application to life. While you might trump me up as being somebody that has many years of experience, so much of what I bring to the table is some fundamentals. I'm anxious to share some of those with you but a fun topic. I'm looking forward to it.

TII David Hrobon | Importance Of Why

We're going to dive right in. There is a quote out there and by putting this out in our interview, I begged somebody to help me find this quote. I have been researching it and trying to find it. You would think with Google, you can find any quote. Stephanie, my assistant and I have been trying to find this quote and we simply can't locate it. If I can't locate it for another year, I'm going to take credit for it.

I can't because I was not good at those quotes. The quote is, “Success in life and business consists not only in the pursuit of excellence but also in the humble willingness to start over.” This idea that we start over brings me back to your comment about kindergarten. Some of the wisest people that I know often feel like, “Let's return to those fundamentals.”

I thought the quote was to Dale Carnegie but whoever said that humility to start over, be young again and be thoughtful again. That takes a little bit of humility because how many people sit around and go, “I’ve been there, done that. Do we get to do that again? Do we got to recreate our business?” If that becomes our posture, then we're missing this idea of finding success in the little ways that we can start over. What do you think about that?

I used the quote from the book by Robert Fulghum and I was thinking, “If I were to write a book, I would say all I needed to know, I learned or confirmed by running.” There has been an incredible parallel to the things that I have seen, witnessed, learn and experienced in life that goes back to every fundamental that I have learned through my journey of being a long-distance runner for 40 to 50 years. It's amazing. It takes you back to some of the basic fundamentals.

I can't run a race if I don't put my uniform and my number on. I can't run a race if I don't train and prepare for it. I can't eat a pizza right before I go out on a race and expect to finish without leaving that pizza on the side of the road. There are so many things that talk about starting from a fundamental aspect to getting from here to there.

This isn't what our topic is about. Thank you for that. That's great. You and I have been on a couple of runs together. I wanted to say that whenever I’m running with a guy like you, if you didn't notice, I asked you a lot of questions, not because I was trying to be a great coach. That's not why. It's because when I'm running with you, I can't speak. It's a little trick to ask you deep questions and let you go.

Little did you know, I'm trying to breathe to keep up with you. It's a little tricky. I know that you know that. Before you hit a hill, ask some person about their life and times in childhood. Let's dive in. I want to get right into it. I asked you to think about 2 or 3 specific things. This is an interesting season in the business. I'm going to say interesting because we're going to try to keep it all positive here.

There are some challenging things associated with that but there are also good things. I want to find these 2 or 3 nuggets that I asked you to think about. I don't know what they are, which makes it fun for me. Talk to the group. With your experience and everything you've got, let's start. What are things that you would say in this season that people can do to navigate and have hope through this season to do some things that cannot just help them get through but thrive through the season to do good? What do you got for us?

This show is not going to be Pollyanna, ignoring the realities of the world that exists and in the mortgage space in particular. It is tough. A comment that I have used thousands of times is the mortgage industry is not easy. It's certainly not for the faint of heart. The reality is that when your pipeline is chock full of loans, you've got people that are having an expectation, they wanted information and answers yesterday and you can't get that through the pipeline to the closing table.

You've got a reputation, challenges and referrals coming from customers and clients that are potentially in jeopardy. There's a lot of stress and even a productive market like we saw in 2020 and the first half of 2021. That's incredibly stressful, just as stressful as it is in 2022. The only difference is the dollars of commissions, earnings and profits are dramatically different. Maybe that adds a higher level but as far as managing the business, I would offer you they're both difficult.

That's what attracts people to this industry. This industry is caffeinated. The people that are in it are type A adrenaline junkies and that's what people are attracted to. It's the thrill of the kill and hunt. It's the thrill of being able to accomplish and achieve something that is not easy. It's difficult. It is the time for quick and thoughtful decisions but executing and making some of those tough decisions.

TII David Hrobon | Importance Of Why

Importance Of Why: The mortgage industry is caffeinated. It is full of Type-A adrenaline junkies that attract other people to the thrill of the hunt.


Whether you're the leader of the company or anyone else within that organization, you all have decisions to make about how to either survive or thrive. When I think about turning points or inflection points in the business when it goes from either being slow to busy or busy to slow, it's about sitting back for a moment and asking a couple of important questions. Any road will get you there but you need to know which road you're on. It's being thoughtful about what you want to accomplish.

The first thing that I would offer is you need to know exactly what it is that you want to change, improve or accomplish and why? I take that back to my analogy of running. If I say that I want to run a 26.2-mile marathon, what I want to do is pretty clear but why do I want to do it? When I look at people who either don't finish, don't get through the training or don't sign up and don't start, it's frequently because it wasn't that important to them. That's about understanding why you want to do it and why it's important to you.

I don't have the luxury of being able to go back into the thing. People that are reading can reread. What do you want to change, improve or accomplish? This idea of why, which so many people have heard whether it's Simon Sinek or whoever, there's a lot of work out there. Jim Collins wrote about that idea of the why. What if some people are going, “Not that again? I did the why. I did it back in 2019.” What do you say to that?

As they say in marketing, there are no new ideas leveraging and utilizing some good ones from the past. I don't want to suggest that I have nuggets that are unique to me or wisdom. It is rather providing clarity around why it's important in this industry. I look at people that decide that they want to lose weight or want to address a medical issue. I went to a doctor and had a physical number of years ago and he said, “David, your blood sugar is high.” For a guy that runs and eats pretty healthy, that was a concerning thing.

He used the term pre-diabetic with me and he said, “Would you like me to give you some medication?” I said, “No. I would like to address it with diet first.” One of the things I found was I was drinking a lot of Gatorade, which is loaded with sugar but I went on a very strict diet. I lost 16 pounds that I didn't have to lose.

My level of commitment and focus around my diet was nothing I'd ever seen in my life before, even in training for marathons. My point is that when I had a purpose, a mission, a passion and a fear that was bigger than anything that I ever saw in my life, my level of commitment to addressing my diet was none other.

Having your why seems a little glitchy but it's also understanding it at a deeper level, the passion behind it and understanding why it's important to you. If it's just kind of important to you, you might drop your blood sugar a little bit and then go and get on medication or whatever it is that you're trying to accomplish or challenge.

Having your why in life may seem a little glitchy, but it allows you to understand it at a deeper level and the passion behind it.

If you relate that to the mortgage business, is it about recruiting? Is it about retention? Is it about profitability? Is it about deciding that you want to enter a new channel of business or exit a channel? Making some strategic directional decisions about your company or your business and understanding that it won't be easy? To me, understanding why you need to do it makes it a little less stressful because you're a lot more focused and you get from here to there faster and easier.

There's always a part of me that when I hear something like that, I want to go, “Thank you, folks. Goodbye. Go think about that.” I know you got more and I want to hear it. This idea that maybe we've done that, it is glitchy or maybe it's a too big picture. If you lose your why, especially in a season like this, it's going to be tough. To hold onto it, review it, rejuvenate it and think about it, your words are great.

Let me give two other comments as it relates to understanding your why. The idea that almost anyone can run a marathon but not all of them will is the same thing. You might say, “I want to originate $40 million in production this year.” There will be people that will do that. Not everyone will but almost everyone can. I use that analogy with running. My brother has run 21 marathons, including the Boston Marathon and you think, “That's great. I know people have run 100 marathons.”

The difference is he was born with a handicap. His right arm and right leg were underdeveloped. He ran a race in 3 hours and 19 minutes to qualify for Boston in 2002. You look at Tatyana McFadden and if you don't know her name, I encourage the audience to research her. Tatyana McFadden was born without legs and only her arms. She came from Russia and was adopted.

She's won the Boston Marathon, the London Marathon and the New York Marathon in the same year in the wheelchair for 6 years in a row, all 3 of them. Understanding your why and passion illustrates that almost anybody can do tough things if they understand why it's important to them. I'll leave it at that.

We got to have you back on the show. We'll dig into that hole even deeper. What else have you got for us?

It's one thing to understand what you want to do. If I decide that I want to train for a race and I don't write down a training plan, it's a little bit like an athlete not having a coach. I need somebody to create measurable steps. I can't just say, “I want to go out and run a marathon tomorrow.” There's a process that I have to go through. I have to do it in measurable steps. I have to go up a little bit, take a little bit back and then account for injury, illness and all those other things.

To me, creating a realistic, measurable plan and writing it down is not just about accountability. It's about being able to visualize and claim your interim pieces of success but most importantly, share it with somebody. Whether that's sharing it with a coach, a spouse, a friend or a competitor, it creates a level of not only accountability but a level of satisfaction and fun.

When creating a realistic and measurable plan, write it down. It is not just about accountability but also allows you to visualize it, claim your interim pieces of success, and share it with somebody.

It helps you in immeasurable ways. Go out and try to run 20 miles by yourself and then go and try to run 20 miles with 2 other people. It's a remarkable difference. I would offer to create a measurable plan and write it down and you can accomplish great things. The last thing that I would say is about the interruptions.

There are emotional and mental interruptions to accomplishing what you want to do. We've used the terms stink and thinking before but there's a lot of it in the environment. You said it in the intro where you get by the water cooler. We all know that person that finds it a sport to talk about how bad interest rates and the housing inventory is, how challenging the tough loans are and every possible challenge and issue in life. By the time you're done with them, they feel great because they've unloaded. You feel like you want to jump off a bridge and crawl under the covers. You have to be mindful to tackle difficult things.

You have to surround yourself with positive reinforcement, people that can encourage you, things that can encourage you and eliminate, slow down or reduce some of that drip of negativity. For me, the trigger is social media and news. I find that I can only take a small diet of it daily because it tends to bring me down when I see that.

Be mindful about tackling difficult things. Surround yourself with positive reinforcement and with people that can encourage you to reduce that drip of negativity.

That's my thing. Each person has to understand what can hijack them from being focused and accomplished and being somebody willing to tackle difficult things and get there without coming at terrible costs, being frustrated and hating the experience. It's about quieting some of that negativity.

As I listen to that, I wonder about the addiction to social media. I call it that not lightly. I understand the word addiction is not something people like to hear but that's pervasive. There might even be people that listen to that and go, “If you limit that and stuff, are you burying your head in the sand?” If you're limiting news and social media, is that a function of you burying your head in the sand? What do you say to that?

Everything I ever learned or confirmed was from running a race. The analogy again in running is if I train for a marathon and I'm doing some hard, long runs and my pace is a nine-minute pace, I'm exhausted after I'm done. The fun fact to know and tell when you run a race with 20,000 people and you don't run 20 miles, you run 26.2.

My pace wasn't nine minutes a mile. It was eight minutes a mile. You go, “How did you do that?” When you race with 20,000 people, your race pace will be about a mile per minute faster than your hard, long runs. If I surround myself with like-minded, positive can-do, struggling it, trying to get to that finish line, all have the same goal and objective, the inspiration makes me run faster than if I'm there by myself or I've got someone else honking the horn at me saying, “Don't cross the road.”

I look at it and say, “There's an analogy and a parallel there to why I'm surrounding myself by reading an article at a Runner's World Magazine versus listening to some of the negativity that comes across the internet daily enables me to perform at a faster, better, more enjoyable level.” That would be my answer. It may not be right for everyone but I can give thousands of examples of how it's made a difference for me.

I'm sitting here thinking I love your analogy of all those runners. You're certainly a more experienced runner than I am. I did run the New York Marathon four times alongside other marathons. I remember telling people, “When you run the New York Marathon, it's 20 people deep for 26 miles.” When you're running down the road and you're in Harlem, people are going, “Come on. Go.” They're sitting there for four hours yelling at people.

It's the funniest thing. You feel every one of those. You don't know those people. They're out there ringing bells. They might think it's whatever. What I wrote down is do you want to surround yourself in the social media world with all the negativity or with the people that are doing can-do? You get to choose that.

You build an idea of worry about and focus on the things you do control versus the things you don't control. When you focus on changing things like interest rates, inflation or recession, I individually can't affect that. I can't change it. I realize that it is a reality. It creates a factor and an influence on interest rates, which have a dramatic impact on our ability to achieve and succeed or fail and stumble.

The reality is I don't control those things. A lot of social media and/or the news includes things that are informative and interesting but things I can't control. I recognize that you need to be aware of certain things but you can't drown in them. You need to focus on the things that you can control positively. That's my message.

TII David Hrobon | Importance Of Why

Importance Of Why: You cannot control things in social media or the news. Avoid being drowned in them by focusing on the things you can control in a positive way.


The other analogy that I give is that the whole idea of creating measurable steps and a plan is because there are points there where you've succeeded and you have accomplishments. It's before the finish line. It's like, “I got to a certain point. I'm on a certain pace. I feel good.” It's the training where you get to claim your success.

I was able to run in my training 15 miles. That is something to celebrate and feel good about because it was what I put on my plan and I did it. You run it four times in New York. You didn't run it one time. The reason I would offer this is that when you finished it, you had a sense of satisfaction with what you accomplished.

You were in pain, you hurt and probably that afternoon, you didn't say, “I want to do this again.” I would offer somewhere between three days and a week later, you were like, “Let's do that again.” It’s because you know the sense of accomplishment, the adrenaline, the satisfaction that you got from achieving all of the work that you have put into it and there's nothing like it. The Rolling Stones are still traveling. There's a reason. They don't need the money.

I used to tell people, especially in New York but all those races, “Finishing is awesome. It’s the sense of accomplishment.” Usually, if you're in so much pain, you don't feel that right away anyway. Do you want to know the greatest thing about that race? It is sitting in Staten Island with 35,000 or 40,000 other people. You felt this sense of community, which speaks to what you speak about that community.

We're cutting it close here. You gave way more nuggets than three. I told you, this is going to go fast. David, we got to have you back on. The hope that you provided and where we can go, I want to repeat it. This idea that making known what you want to change, improve or accomplish and getting to know your why. I cannot say that is strong enough. Live with it, know it and review it often. Measurable, realistic steps with a plan. Forget the mortgage. Just business in general. How many people do you think have a written down plan percentage-wise?

Not enough. How many people of those share it with someone else is a smaller number.

Share it because you're bringing and that's exactly right. What we're doing is not focusing on the ones that don't. Let's look at the ones that do. I love anybody who can but we’ll be one of the ones that will. We can. That's so healthy and good. Limit interruptions, mental and emotional interruptions, focus on the things for which you have some span of control and recognize it.

Anybody that's ever been through any recovery program, oftentimes, there's a prayer that's called the Serenity Prayer that I know you've heard of. It's weird to end this with a serenity prayer. “God, grant me the serenity to accept the things I can't change. The courage to change the things I can and the wisdom to know the difference.”

As we leave here and end our What If We Series interview, may we have the courage to change the things we can, which is typically ourselves. Recognize that we need some peace around the things that we can't change. I love what you said, limit it anyway. Be informed but don't drink of it. Let's spend some time understanding those. Let's get back to the positive. I believe and I think you do too, this could be an amazing season for those that practice these things.

It will be.

Thank you. You have been awesome. I told you this goes quickly. I want to have you back on. If you want to ask David any further questions, it's pretty easy to get ahold of him at the Stratmor Group. I thank you for your time, your positivity and your friendship. Go out. Help others with their why and keep being you. Thank you

Steve, thank you so much. It's been my pleasure.

We say it every time here on the show, particularly in The What If We Series that it doesn't matter what David's what if we’s are, what if we do this and what if we do that? What are yours? That's what matters. Your comments and thoughts were great, David. Thank you very much. We'll see you next time.


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