Rachel O’Donnell on Company Culture, Leadership & Trust

Welcome back to Mortgage Daddies. Today, we have our special guest, Rachel O’Donnell, our COO. Very special guest, Miss Rachel. Rachel has, uh, never wanted to come on this before and we pretty much had to force her today, so, uh, here she is. Thanks for joining us. Yeah. Thanks so much for having me. I’m Vernon. I run the top mortgage brokerage in Massachusetts with over 20 years of experience. I’m Craig. I’ve done $100 million consistently since my second full year in the business and I’m Massachusetts’ top mortgage broker. We’re the Mortgage Daddies with real advice, real stories and real results. Let’s get going. Rachel, your journey here at Milestone has been, uh, a little chaotic, up and down, right? You come into my office at least once a week and tell me that, uh, we change things up too much or not enough orUm, one of the big things that I’d like to get out there and share with everybody is how you started your journey at Milestone, like we, Craig was talking about earlier. Um, you know, tell us a little bit about graduating college and having your whole life ahead of you and all these big plans and then the mortgage business just sucked you in. Yeah. Um, so I graduated in June of 2019 and my plan was to work for a non-profit and go help the world. I graduated with a sociology and psychology background. Um, and I couldn’t find a job for the first couple of weeks and my mom was like, “Go work for this guy named Vern and, uh, help him out and see where it goes. “So I was like, “Yeah, this guy named Vern, I’m gonna work there for, like, 2 weeks. “And then I started picking up coffees and lunch and, you know, in between all that I learned a lot of the ins and outs of the loan process and I actually ended up loving it, so you know, almost 7 years later, I’m still here. That 2 weeks lasted a lot longer than I expected. I think in that 2 weeks that you started, you know, giving us a try, I think the one thing that separated you is that you always started looking to make everybody around you better, right? You tried to better the process. And even as starting off as a receptionist, or whatever that position is that somebody might be watching this and they’re starting off their careers, is you went out of your way to try to learn what everybody else was doing, make the systems better. I mean, I remember, uh, now I have a mu- much higher standard for everybody who’s watching of making sure I never run out of bottles of water in my office, right? And that kind of goes back to, like, when you started, it wasn’t so much water, but it was kinda chaotic those first couple of years in the mortgage business. You know, starting at Milestone and it was like Craig, it was like the dads, uh, dads. It was the Mortgage Daddies, but there was a bunch of men in the office. And I don’t know how many times they would just be like, “Somebody has to go to the store. We’re out of paper towels. We’re out of toilet paper. “Rachel got there,Everything’s auto-delivered. We’re like, “You can auto-deliver toilet paper? This is amazing. “looking back on it, it’s like she was changing the world at that point, our, our little world. But like, everybody probably just does that outside of it. Yeah. I think when she joined, we just didn’t really have a whole lot set up. We were just focused on loans, loans only, and just tried to close them. But you came in and tried to create a process for everything. first it was the operations of the buil- the building and how we did everything. And then you got more into, like, the loan side of things and fixing, you know, the flow, the operations. Yeah. And, you know, what made you kind of, like, want to take on that lead? Uh, well, I think it started with having to do the manual labor of it all. When I first got here, we were printing every single borrower document and disclosure and file folding and doing all sorts of crazy manual tasks where I was like, “I don’t want to have to do this. “So I created an automation for it and figured out a way to make it faster and better and more communicative across, you know, all platforms that we had back then and make it easier for everybody to get the process through. And make it easier for the borrower. It just blows my mind how much smoother things run with yourself and a couple other people that we have attached ourselves to that we couldn’t run Mortgage Daddies without having Wendy in the background or a lot of other things without Wendy and yourself and a lot of the other, you know, operations staff here at Milestone. But you’re really the one at the top now coaching and making sure that it’s a well-oiled machine. There’s so many times that I just walk in. I was, I’ve been gone for a week and I just walk in, it’s like I never left. Right? Like, business went on, everybody went on, everybody strived and thrived and, uh, you know, that’s kudos to you guys that are, that are here that built this whole thing out. first I think it’s, uh, kudos for you too, though. Like, you gave us the strength and the power to be able to run with it and, you know, you trust our decisions, which is huge, right? Like, if your team can’t run without you while you’re gone and you’re really, you know, the best leader that you can be, that makes you the best leader- Yeah. because you know that we can run this place with you being gone and you come back with these crazy ideas and we work on implementing them, figuring them out and making them the best we can. Just for all our viewers out there, I have been gone for 7 days and all the crazy ideas that are still in my head she hasn’t seen because-I’ve only been here for 4 hours. Every time he goes away, he comes back with crazy ideas. I haven’t given him the reaps yet. It’s so weird. I’m actually taking PTO, so best of luck. Lot of crazy ideas coming down the pike, but, um, you know, what’s been like one of your biggest struggles in your first 5 or 6 years in your professional life here at Milestone just as overall for anybody? Like what are the one thing, 2 things that you’re like, “You know what? I really struggled with that piece. “You were able to get through it, I hope. This is where she tells us she’s leaving. Honestly, I think it’s imposter syndrome. Like, not feeling like you’re supposed to be where you are at such a young age. I mean, I’m a chief operating officer at 28 years old. Like, that’s pretty crazy. And some days you look back and you’re like, “Ooh,” like, “am I supposed to be where I’m at right now or is there someone that better could do this? “And you gotta look back and think, like, there is a reason you’re in this seat right now. You gotta own that and, you know, do the best you can ’cause, you know, you got here for a reason and make it the best you possibly can. That’s a really good answer. Yeah. I feel like I stole that one too. Like, that’s gonna be my answer if somebody asks me that. No, I definitely, like-feel where she’s coming from- Feel that way. ’cause I feel the same at times. Like, you know, I got into this and started doing loans and never really thought of doing anything else. And then you get put more in a leadership role, and now you’re talking to people that have been in this business for 20 years more than me, and I’m telling them what to do or, you know, they’re looking at me for advice. And it’s like, “Uh, I just know how I do things. “And like- Yeah. I can tell you how I do it, you know, take it or leave it. But it isI, I totally get where you’re coming from. I thought you were gonna say something totally different. What’d you think I was gonna say? Giving up control- Oh. would’ve been my thing, which I- Trying to fix that. struggle with as well. So, you know, I get that side of it because it’s hard. Like, I think for nobody listening, uh, for anybody listening now, like when we started, it was just a handful of people, so everybody had to do everything. Everything. And we had to learn how to do things and learn how to do certain things, or we had to learn how to build the system. Like we didn’t, you know, trial and error too. We all v- gone through multiple systems. We’ve gone through different CRMs, different LOS, uh, you know, uh, from start to finish- We’ve tried it all. we’ve changed things multiple times to try to figure out what works best. when you do it that way, you really, like, learn how to use every piece of it and how to operate and how to effectively use the systems that we put in place, versus just like, I would say, going somewhere and just already having, this is what you use, and not having to, like, be in the ground floor. So that’s been a huge benefit, you know, on my end and I’m sure- Mm-hmm. on your end is- Right. how we trial them, how we build them out. And then now it’s a lot ea- if we make a change now, it’s a lot easier to make a change now. But the giving up the control side of things I think is tough for anybody. You know, as a company grows, we started with a couple of people, so you did a hell of a lot more roles than you do now. You know, you did a lot more roles than you do now. You don’t have a problem giving up the control side of it, but hey, here you go. Figure it out, you know, run with it. I’ll be gone-in 7 more months. Bye, guys. But it’s hard for you, and I see that- Don’t need you. and I watch you do it because it’s like, you’re afraid of being replaced. And it’s notI think, like, as you’re growing a company, it’s important to be able to do that because you have to give up control of certain pieces, otherwise you’re never gonna grow. Yeah. You know, and we’ve talked to pe- I’ve talked to people about how to do it on my end. You’ve talked to people. Like, KB’s a great person to talk to about it because she brings up great points. Like, you can’t have somebody in that type of a position that’s unwilling to give up control, otherwise you’re always gonna, you’re gonna hit a limit. Hmm. You know, you’re not gonna be able to move past it because you can’t do A, B, C, and D every day if we double our production or we- Yeah. double the amount of people that we have here. You have to give up, you know, C and D and figure out just, you know, what’s the most effective things that you can do and who can do those other roles? And it’s hard, it was hard for me with growing a team and letting people do things that I usually do. It’s hard for you with the operations end, is having somebody else take on that responsibility. And, uh, you know, it’s a hard thing, especially when you’re young because everybody sitting in here is competitive- Yeah. at the end of the day. Maybe not so much on the sports side of things with you. I don’t know what you’re talking about. I’m pretty athletic. No, ’cause you’re athletic. But it’s still, like, it’s a competitive drive at work every day- Yeah. ’cause you wanna be the best and you wanna be the highest, you know, the per- the person that everybody looks up to or comes- Hmm. to ask questions. But it’s impossible to continue to grow if you’re the person having to answer every single question at every single level- Yeah. of the process. No, and I justI, I look at it now that I, I get to get out and go travel to some of our investors. We just had, you know, some people, KB, uh, down visiting. Surrounding yourself with people that have already done it and built it out and understand it, and being able to lean on them for advice, has been what’s been able to change my mindset, like, overnight. Like, now I look at it and like, all right, I think we’re at a company now with 75 employees. And like, in my head I’m like, in 2 months, it’s gonna be 125. In 6 months, it could be 200. Is it really the best use of my time to be doing X or Y? And then, you know, my biggest job now is to make sure that you guys are super happy and you guys are taking stuff off your plate. You guys are thriving and we’re all going the, kinda in the same direction. And honestly, both of you guys make my life a lot easier because you guys just come to work every single day to be the best. It makes my, likeI don’t even know what I, I don’t ev- f- sometimes I think it’s not imposter syndrome, I just, you guys don’t need me here anymore. Like-at some point I’m just gonna walk in and Craig’s gonna be like, “Dude, really rather if you just leave. “But then, you know, it’s nice. I’m, I’m, I’m away last week and I get a text from Craig, he’s like, “Hey man, really miss you in the office. It’s just not the same without you. “And I’m like, “All right,” so he does still- Did you really send that? he still liked me a little bit. . Yeah. I was like, “Maybe he’s just saying this because I’m in a hotel by myself. “It’s a lot quieter, and like- Yeah, it is. But the chaos is fun. Yeah. You know what I mean? It’s like, I think- He brings the energy. That’s what makes it fun. we all bring different pieces to the table that, I mean, one thing that you talk about all the time that’s so important to you and you always are pushing is the culture. Having a good culture. And it’s important to you, and I think it is important to everybody, because we have so many people here that come in every day and I feel like they look forward to coming to work, because it’s not- Yeah. boring, it’s not the same thing every day, you know, it’s not punch a clock, punch a clock out, see you later, not talk. It’s like everybody here is friends, and- Yeah. family, and you’ve grown up, a lot of us have grown up together, and that, the friendships that we’ve started with have become, you know, even closer, and you, as we add people, people come into that mix. But it’s, the culture here is super good, in my opinion. Like it’s better than anywhere I could’ve e- I never wanted to work an office job. Like I was terrified of doing it when I got outta high school. I was like, “What c-” Now we can’t get you out of the office. Yeah. “What can I do to, like, never sit behind a desk all day long? “So that’s why I went to become a firefighter. But when I started here, it never had that vibe or that feeling- Yeah. that was like, “This sucks. Like I’m sitting here watching the clock till 5:00 when I leave. “Most of the time it’s like, “Shit, it’s 7:00, we should probably get outta here- Yeah. so we don’t get killed when we get home. “Yeah, wife and kids don’t like it when you’re coming home at 7:00, 8:00 at night. I feel like our team is very in it to win it, and everyone is, you know, willing to put in whatever work they need to do to get it done. And, you know, that helps make it a lot, you know, more enjoyable on a day-to-day basis. And the other thing is that it’s just rewarding, being able to do what we do. Whether it’s on the operations side or the sales side, we’re like, we’re able to help thousands of families each year to get a home and, you know, better their financial future, and that’s huge, right? Like that’s a really, really great feeling when you think back to it. So down at the foundation of where we are, like that’s why people come to work d- every day, ’cause they wanna help people. They wanna help people get pre-approved, they wanna help people get through the process. And that makes it easy, you know, to, to wanna work here, to wanna be here every singleI feel like when we, the 3 of us basically started Milestone all at the same time, right? You and I started March 5th, you started July? June. June, July, same year. We’ve really been able to go from, and you, you talk about this on, uh, maybe I, I started on the New Bedford Guy podcast, is when you first started off, no one knew who Craig Snow was. On top of it, no one knew who Milestone was. So you’re coming to work for a company no one’s ever heard of. I got a little bit lucky because people knew who I was but they’re like, “This guy’s starting his own mortgage company. Like this is, this is probably not gonna work out. “And now, we’re like recently over the last couple of years definitely, like just in the last couple of weeks, “Oh, if that’s a Milestone preapproval, yeah, we’ll, we’re, we’re, we’re good. “And then it’s like now we’re kind of like that leader in our area, uh, and I think that’s what, that’s, that’s super rewarding. Um- Yeah, that’s awesome. Just- I mean, it’s, it, ’cause that just goes back to show like the care that we have, ’cause if you just, if you work somewhere that doesn’t care or you have people that don’t do a good job, it’s gonna hurt your reputation if you work- Yeah. for that company. Realtors talk to each other. Yep. So if you, you know, a transaction, deals go bad, nobody can protect every deal from not going bad, but if you work at a company where, you know, the way that they handle when it goes bad isn’t great, you know, the responses, the attitude, the shortness, the lack of responses, that trickles down. And now if everybody acts that way or multiple people at the company act that way, that’s gonna get out to the realtors. Well, what’s gonna happen? It’s gonna hurt you as a loan officer because now your client’s offer is not gonna get accepted because, you know, Susie that works at XYZ Realtor had a bad experience, she told this other person and now they don’t wanna accept an offer because theyAnd I think we hold everybody here to a very high standard with, I mean, uh, we brought in a l- like we didn’t know, right, trying to set up trainings and teach people and everything, we’re like, you know, trying to build this out and we don’t know how much, how little you need. But I feel like, I feel like we don’t do enough but at the same time we bring people in who have worked at numerous companies that are like, “You’re, you guys do so much training. Like this is awesome. “. I’m like, “What did the other companies do? “Like- Yeah. I don’t think they do anything. . We, we, uh, Rachael and I have never worked anywhere else, like- Yeah. on this side of the business before, so we don’t know. But, you know, we try, I think we’ve brought so many people from nothing, meaning no experience, not from nothing, from no experience in this business to being really good loan officers so we know how to take, you know, we all do, we know how to take people from knowing nothing in this business to being very successful- Yeah. and to having a good career, and showing what those value pieces are that are, in my opinion, non-negotiables of, you know, how you talk to clients, how you pre-approves somebody, how the loan process goes so that we don’t have a bad reputation out there. And, you know, as a loan officer, working at a company that has a bad reputation would be detrimental. You know? In my opinion. I think it, you know, just to bring it back to the whole letting control go, you know, as I, as we’ve grown, we’ve brought on a lot of great people and one of them is our head of marketing, Sarah, right? Like we didn’t have a brand before Sarah got here. We had a logo, we had a, you know, a slogan, but we didn’t really have a whole brand. And then Sarah came on and, you know, we were able to actually implement all of Milestone, who we really are and put that out on the streets. And like, people really see behind, you know, the screen who Milestone is, and I think that’s a huge aspect of it all too, is really, people know who Milestone 0 is not only in the New Bedford area now, but we’re growing across the country rapidly. And having those people in those places to be able to help us grow and bring on the right people is huge. I think, you know, letting go of control is important because you can see what other people can do better than you. And you know, we all have skills and strengths, and maybe some of the things that you were doing or I was doing weren’t really our strengths. Yeah. And bring on those people to help us. You’reYeah. AndYou did marketing. Yeah, well, IRachael did marketing, guys. I survived. It was more of like, yeah, who, who can kinda operate a Canva account? Yeah. And now it’s a lot, you know, people come in and they have everything they need. Like, we, we would make things as they were asked for. Or like, not like preset things in there. And you know, those are little things that you don’tyou and I never would’ve thought of. No. If it was just you and I, no chance we would care. No company scoreboard. No. Nothing. Because all you’re doing is f- like ’cause people have- Constantly. Yeah, like different people have different focuses and what visions or whatever. But when you can getAnd one of the favorite things that we do now, you know, with our weekly sync calls with all the kinda heads of every department is, it’s always interesting. Like we’ll bring up a topic and everybody has a different idea of how it should be done because- And they’re all good. You’re looking at it as one view. I’m looking at it as like the LO side of things or like, you know, how is this gonna work with operations and LOs? You’re looking at it in a completely different view. Sara’s looking at it in the marketing view. You know, Denisa on the operations end. Russell more on the technology side. And it’s like, Sean more on the recruiting side. Okay, how can we bring this all together? Yeah. To make th- which is nice because now you’re getting a lot mor- not just one person thinking. Because nobody, not one person is always right. No. And I think what works out well isCan you record that again? I mean, besides me. Uh, but not one person is ever gonna have the right vi- So if it’s just one person making all the decisions, you’re, you’re just gonna be tunneled into one direction. Yeah. And here, I think we move around a lot in what we focus on because everybody has different ideas and then, “Okay, hey, let’s give this a try” or “Let’s give that a try. “And over time, you know, you figure out what works best for you and your company. Yeah, it just goes back to the culture that we’ve all been able to really put our 2 cents into and, you know, our little add-on for the culture and Rachael’s a big part of that culture. And you know, I hear it when I go home, I hear it from my, my friends that I do not work with and most of ’em all tell me that I spend all my time at Milestone and with Milestone people. you know, it’s fair to say that I spend most of my waking hours with the 2 of you and, and the rest of the crew that’s out of the New Bedford office or talking to Sean Lee in Washington or Adrian. I think that’s really what we’ve built here, is it’s almost like, I don’t like to call it a family, but like a team, right? And then we got some, some out 0 out 0 out-of-town teams that are all part of it, but you guys make everybody around you feel welcome, right? Like, we don’t really have that outcast loan officer or operations person that doesn’t feel welcome, doesn’t wanna come to the office. I walked over to the sales side today and there’s multiple loan officers that drove more than one hour to come into the office on a Monday. Unless I was being paid, I never drove anywhere as a loan officer unless I really liked going there, right? So, um, kudos to you guys. Rachael, thank you for coming on Mortgage Daddies. I know this is at the top of your list of what you wanted to do with your life today. Yeah, for sure. Thanks for having me. I mean, I will, I will say on that, that topic, like a lot of the, or how things are here and, and because we can change things, a lot of people get to put input, it makes it better, but without you being willing to take other people’s advice or listen to other people, it would never be possible. I mean, how many companies are out there and there’s one head that just is like a dictator? Yeah. And you know, “Oh no, it’s gonna be this way, my way or the highway,” and well, it’s never gonna grow. It’s gonna be stale because it’s just gonna be following that one person’s vision and then what’s gonna happen to everybody that works under them? They’re gonna get discouraged. “Well, my, my opinion doesn’t matter, my views don’t matter. “You know, and I’ve talked to the people that work and it’s like, they like to have an input or they like to see, like you’ll talk to somebody that joined us 2 months ago and if they have a good idea, you’re gonna bring it to the table and we’re gonna try to implement it if it works. Could be fresh. Yeah, it could be a great idea. Mm-hmm. You know, like we have people- I tell everybody when they’re getting onboarded here that we’re like the melting pot of mortgage companies, that if they have something that has happened in another company that we can take on and make better in our process, let us hear it, because at the end of the day, that’s kind of what we’ve become. Yeah. Is other people are coming from other different companies saying, “Hey, you know, you should implement a leader board or you should implement, you know, a branding kit or you should implement, you know, a get-up-and-grow challenge. “There are so many things that we’ve implemented from other people saying, “This is something I really liked at my other company, but I left there because of X, Y and Z. “And, you know, Milestone was able to add that and make it another benefit for the loan officer. And we have multiple people that have owned their own company- Yeah. and have come here, and they obviously have great ideas and know how to do things that- Yeah. ha- that add value, and then they like a lot of the things that we do. And I think it’s like, to me, for people that own their own company to come work here and enjoy it and stay here, that’sI mean, there’s nothing in myMost people, once they own their own company, you don’t think they’re ever gonna go back to working for somebody else. But that’s huge, you know, in my opinion. Like that’s- We’ve had 3, 4, 5 of those in the last 90 days give or take, and most of them have all contacted me directly saying how smooth the onboarding process was from the operations side. And I would say like 3 years ago,uh, probably 2 years ago, we didn’t even know what onboarding was. My idea of onboarding was here’s a laptop, you got everything you need. Go sling some deals and- Best luck. and we’ll go from there, but- It’s come a long way. What’s the next 6 years gonna look like? Hopefully a lot less work on my plate. A tire changer. Just kidding, just kidding. No, I’m not. No, I’m not. I’m gonna be sitting in the closet just doing loans, that’s all I want to go back to doing. Like half the time I’m like, “I just want to sling deals again. “Revert back to 3 people. . Yeah. Cut ’em all out. I, I always look back and I’m like, “You know what? “We’re just kidding, that’s not gonna happen. Some of the loan officers over there, that’sand, and, and God bless them, that’s all you had to do, right? Like you don’t know what you don’t have or what you have until it’s either like gone and likeIt’s hard for me, and you guys are going through this, to give up doing loans. Like because I see the, the energy that’s on that side, when they’re all pumped up. The rates go down by a quarter, it’s gonna be chaos in here, right? EverybodyAnd I’m like, “Damn, how do I get like a little taste of that? How do I have some fun with that? How do I get back into that loan game? “And then it’s, it’s hard because you want to, but then you know if I do that just a little bit, then I’m gonna start doing a little bit more and it’s gonna take us away from like really what we’re- we’re all trying to accomplish here. And obviously that’s, uh, that’s growing exponentially over the next couple years. But I think if the rates do go down, I think I’m gonna have to have some fun. I keep talking about it. Can’t, where you are. I think the way that you replace that is you go from, you know, helping borrowers to their first home to helping loan officers into their first loan. Yeah. And that’s what gives you your new dopamine rush is like being able to help our team, help the new loan officers that come on really be successful and, you know, give them the roadmap and the game plan of what made you- Yeah. the loan officer you are. I think that you can see your eyes shining when you start to really help people and you see their light bulb turn on, it’s really awesome to watch. I was lucky enough to, um, be out in Washington last week, and Sean Lee, our business development officer, set up a lunch. And it was just a Masterminds lunch, and I really did not have a high expectation for this. Full disclosure, sorry to say that, Sean, it came out. Poor Sean. I really didn’t have a high expectation. ItAnd not that he wouldn’t be able to, to pull it off, there was just a real small window of time for him to be able to do this. So we, we threw an event at an amazing restaurant in, um, Ascend in Bellevue, Washington. I walk into the room maybe 20 minutes early, try to get set up, and I don’t know what I’m gonna expect. I don’t know what I’m walking into, right? How many times have you had a broker open house, you have s- you put 10 or 12 people? Very limited group. Think there was like 10 or 11 invites. 8 of them showed up. There was over one billion dollars worth of production in that one room with 8 people. And that’sI was sitting in the back almost like pinching myself. There’s a billion dollars in this room and they’re here to find out what we have for technology and what we do for marketing and what we’re doing, and we’re competing with the big boy retail like chains out there. I’m not gonna say any of them on here, I’m not trying to get myself in trouble. But the big boys, your top 5 or 6 lenders. And every single one of them were like, “You guys have something really special going on,” right? Like for the most part, and they’re looking at like our technology, they’re looking at some of the marketing. At that point, that was like an a-ha moment. I’m like, “This thing really has like a lot of legs going. “Like in a matter ofI mean, I think it was like 10 days he was able to put this event together. And that goes back to, you know, I wish you guys were there to see that because it was like, “Holy shit,” like, “we could actually be onto something like really crazy over here. “Goes back to you guys, I’m telling you so. Good job. Good job. Onto the next one. Looking forward to the next 6 years, see what we can do. Can’t wait. Hopefully private aviation. See you guys next time.