Katalina Dawson (00:11)
Hello and welcome back to another episode of Career Path. I am your host, Katalina. Today we are discussing the topic of taking the first step in your career. And here to discuss this topic with me, I have Michael Cassidy, who is the Chief Operating Officer for Velocity Investments, a national debt buyer. And he is also a director on RMAI's Board of Directors. So Michael, thank you so much for coming on with me today. I am super excited to have you.

Michael Cassidy (00:35)
No, thanks. Thanks for having me. I'm excited.

Katalina Dawson (00:37)
Awesome, well I'm gonna start with the same question I start everybody off with and that is tell us a little bit about yourself and how you got to where you are today.

Michael Cassidy (00:45)
Yeah, I'm based here in New Jersey, also where our company Velocity is My wife and I returned back here in 2017 after a 12-year escape for me, eight year for my wife. Came back to be closer to family and start our own family. We now have two kids. Kind of my career, I think mine started like many or probably most in this industry with zero intent to end up here, ⁓ for better or worse. I answered a newspaper ad, which ultimately led me to a New Jersey creditor rights law firm right after college to my father's disappointment. But I mean that

Katalina Dawson (01:19)
Yes, accurate.

Michael Cassidy (01:33)
that two years I spent there really helped kickstart this, kind of an accidental into the industry. After about two years with the law firm, in lieu of taking a promotion, I kind of had that first bit of anxiety, if you will, of I don't know if I want to do this. I don't know if can stay here. Nothing against the company, but you get that. Maybe it's young in the career. You get kind of the jitters of what am I doing? I used that for better or worse, it ended up being better, to jump out and take my first move. So instead of taking a promotion, I made the leap about two hours south to Delaware, not a huge move, but it ended up being a really great career move to jump over to the Carter Shore side where I spent really the next eight plus years. And I was fortunate, mean, that move allowed me through really great leaders making very poor decisions to take on a whole bunch of opportunities that I probably wasn't initially equipped for. In 2006, I took an opportunity to open our first call center outside of the Delaware area. At the time, I didn't know if it was gonna be in Albuquerque or Colorado Springs. I hadn't been to either and I was like, cool, I don't know much going on, I'll do it. I out to Colorado where I lived for a couple of years before jumping back to Delaware, getting on the agency management side, which helped me expand a network, which I think we'll touch on a little bit later, but allowed me to expand beyond just the company I was working with, working for, and start to meet other companies in the broader industry, if you will. That eventually, again, more great people doing questionable things. I got opportunities to do some work out with sister companies, one out in Stockholm, Sweden, and another one in Germany to consult, if you will, or try to help the parent company. That I learned my first, I guess, two really good experiences. One was my first rejection, which was professional rejection, which was awesome. And I really loved the Stockholm opportunity applied for a permanent role. Learned a bit of humility that I was not prepared for it. I was not the best candidate for it, did not get that role. And then I got a taste of the other side, which was, the Germany opportunity was a bit more of an extended stay. And I was given the opportunity. They asked if I would, you know, I would stay, if I would, you know, take a role and permanently move out. And on the other side, it just wasn't the right role for me. And, you know, just at that time, I didn't feel it was right and decided not to take it.

That led to a year later, I decided to go back on the agency side instead of the law firm. I two and a half years running US operations for a collection agency. Another great opportunity, understanding more about P&L, more about doing collections as a profit versus doing it for protecting your losses on the issuer side. And that one I love because it's, try to fast forward, it's kind how I got here.

That one, just through networking, maintaining a network of individuals, I had a former mentee of mine that the bank had a program running, reach out to me randomly saying she wanted to get out to the Bay Area. Did I know any companies? And I did. I reached out to a former colleague of mine who was at a FinTech in the Bay Area and said, hey, I know this person, good person. If you want to hire, great. If you don't, I'll never mention your name to her and we'll just move on. And just that random outreach, not only got her hired, her relocated Bay Area where she wanted to go, but I accidentally got me a role to build out collections recovery and relocate my wife and I to the Bay Area to join Prosper pretty early in the FinTech days. And that accidental, which I guess there's a sad definition of a lot of what I've done that accidental success was pretty incredible. Prosper is where I met a lot of awesome folks, a brand, not a new industry, but an emerging market, if you will. This FinTech market, which is now basically blown up. It's where, 2014, when I first met Jim Mastroianni and the Velocity folks, they were one of my earliest entities we sold debt to.

I met the two individuals who in 2019, I would eventually leave Prosper and start a consulting firm with, just kind of building off that network and ended up, know, 2024 joining here at Velocity. So it's been a lot of accidental success, I'm going to call it.

Katalina Dawson (06:05)
Yeah, a lot of twists and turns and even some international opportunities, which is incredible. But I completely understand not wanting to change your, uproot your entire life and move overseas. So I'm curious a little bit more because a lot of what you said really dives into this kind of taking the first step. You would just reach out. But to dive into a little bit more of it specifically on the networking side. So how has taking the first step in networking specifically influenced your professional community today.

Michael Cassidy (06:34)
Yeah, I think it's done almost everything to it. I call it this bit of an accidental success, it's not obviously it's not accidental. Most of mine came through establishing a network. I am naturally an anxious person who doesn't naturally like networking. I love communicating. I love talking to people. But the concept that I always thought networking of this, you know, out, introduce your elevator pitch and doing this like that was never natural to me. ⁓ And I think as I gained experience and gain comfort, a lot learning from others, you learn to kind of find your your version of networking.

Katalina Dawson (07:04)
Yeah.

Michael Cassidy (07:15)
Mine was just developing relationships. I loved talking to people. And my version of networking became this, you know, establishing this network of people that I knew and that I like, that hopefully they, like me, or at least were willing to talk to me. And, and that led to most of my early success was, you know, building this network of people, not just a network of like contacts. And that's kind of how I got most of the opportunities.

Katalina Dawson (07:36)
Yeah, it goes back to the, like, people do business with people that they like philosophy. So you really embody that and that's amazing. I know things are so different now, especially with remote work versus how everybody used to be in office. Do you see a big change in that? And do you think it's harder to kind of take the first step when it is this kind of remote setting?

Michael Cassidy (07:59)
I think it's more challenging, again, for a personality like mine, or I find it more challenging, right? my version of networking, again, was developing a relationship. And I think that's really, nothing is easy to do, but I when you're in person, you're working with your colleagues in an office, it becomes very natural. You just develop like you were in school. You just develop.

You develop relationships, working relationships, friendships, that naturally, I think more naturally comes about. And then as your career grows, people move to other companies, even within a company, move to other departments, learn other things, and then move externally. And you see this network grow out from that. So I think when you're in office, you can get this natural expansion of a network. When you're remote, that gets a little bit more challenging even within a company, think it's, you have to be more proactive, I feel, to have a discussion that's not just, hey, we're doing a meeting, we're doing this topic, and you're on Zoom, or you're on something else. It's very transactional, and being able to find opportunities to communicate outside of that becomes, it's more on you to do it. So I do think it's more challenging. think...

Michael Cassidy (09:17)
Like anything, it can be overcome. You just have to tweak it. You have to make sure you have time to develop a personal dialogue or conversation. Conferences, I think, are wonderful opportunities if you gain comfort navigating them. think it's certain conferences, you can get overwhelmed or kind of swept up in it. But yeah, I do think it's more challenging. think it's got to be more conscious now than it was maybe when I was when I was building my career.

Katalina Dawson (09:47)
Have there been any programs along the way that kind of helped you take those first steps in initiating?

Michael Cassidy (09:52)
When I was doing it, mine was really... I'll speak to a program that came afterwards, but mine really was very much this personal development. And I think that large, I can't call it a program, I think you leveraged your leaders, finding your mentor, if you will, and watching and emulating. Emulating in some cases...

Katalina Dawson (10:10)
Yeah.

Michael Cassidy (10:15)
trying to do completely the opposite in others, but you find ways to learn from folks. How do they ask questions? How do they start a conversation that doesn't feel like that elevator pitch, if you will, where you're just immediately going into the product you're selling? How do you make it sound natural? I think you can do that by watching others always, whether you're remote, you're in office, you're at a conference, I think if you find the right folks and really pay attention. Yeah, although I think you can learn, you can learn from anyone, you know.

Katalina Dawson (10:43)
Yeah, 100% you can always learn what not to do as well as what to do.

Michael Cassidy (10:55)
Yeah, making sure it fits your personality. My approach is probably very awkward for some people. I like to make everything about some personal conversation or a sarcasm or like that's not one, will not naturally work for everyone and it won't be received well by everyone if you're not careful in how you use it. I think you try to whether officially or unofficially from those around you.

Katalina Dawson (11:13)
Yeah.

Michael Cassidy (11:22)
I did take part in a I enjoyed for, I think, three years. And this was in the COVID, post-COVID time of the university I attended. Did it pretty cool, which I'll bet is more common now, but for the first year business students, they had this virtual networking session where alumni volunteered and you would have a panel of, I don't recall how many, of folks that they would, You played the role of just having the conversation. They would introduce themselves. You would ask questions. And it was less about the pitch, although I think they all had to come with something. But it was more the conversation. It's someone you don't know at all. And trying to form this conversation and gaining comfort in doing this. I thought it was just an interesting way to try to navigate the newer days of this remote environment.

Michael Cassidy (12:13)
But yeah, think whether it's a true program or something that you do more naturally on your own, you have to gain comfort in it. If you just go into a conference and like, I'm to go to a conference and network, it's probably not going to work as well as you think it will.

Katalina Dawson (12:27)
Yeah. 100%. Now outside of networking, how would you define that taking the first step in your career and how do you embody it?

Michael Cassidy (12:40)
I mean, even just the concept of hearing, taking the first step gives me anxiety. No, I think you, you know, I think you start with, there's no blind first step, you know, it's finding a direction or something that you want to work towards. ⁓ An opportunity. Yeah, it's a great one, right? Find the right opportunity. Then you're internalizing.

Katalina Dawson (12:50)
Like an opportunity?

Michael Cassidy (13:03)
All right, is it something I want to do? You know, yes or no. I think that first part is really critical. It's whether the opportunity found you, which in my case, a lot of them did. I didn't seek them out. was, you know, kind of the right place at the right time. But whether you seek it out or it kind of finds you, I think the first step is internalizing it, spending a little bit of time to figure out what does it mean? What does it mean to me? Do I want to do it? Verses that initial...

Katalina Dawson (13:05)
Yeah.

Michael Cassidy (13:29)
I think we're often people pleasers. You're like, yes, it's an opportunity. should take it. You should probably think about it a little bit more.

Katalina Dawson (13:36)
Yeah, so it's not just about saying yes to everything, but saying yes to the right thing and vetting something to make sure it's the right opportunity for you.

Michael Cassidy (13:44)
Yes, I think entirely. I see this a lot again. My version of networking is maintaining relationships. When I was consulting for the five years, didn't have a sales engine. was leveraging our network of people we knew and just having a conversation and hopefully something came up. like, I forgot Mike existed. Maybe there's this thing we could do together.

But I think getting that comfort of, all right, let me think through what I want to do. You learn how to probe. You learn how to just ask questions. I find it with a lot of my network now, they'll reach out or I'll talk to them and say, hey, I have this really great opportunity. I think I'm going to take it. And then you're like, oh, cool. And you sit back and say, right, what is it? the company? What's the role? What's the industry it's in? You try to help people as best as I can, if they even want it. You try to help them sometimes think through, does it follow a logical narrative for your career? And it's not me to decide for someone. I love helping people get towards that, which is, are you pursuing something that's logical, that's building upon something you've already done and keeping you.

Michael Cassidy (15:04)
And I think you find in a lot of folks, it's just the excitement of something new or a title or compensation. mean, things, compensation certainly matters. Title, I never want to celebrate a title. It's just not my thing. But I think folks can get swept up in what they think is a great opportunity and not go the levels deeper to say, is it logical? What happens if? What if you don't like it?

Katalina Dawson (15:33)
Yeah.

Michael Cassidy (15:34)
Do you just know one person there that you were like, Katalina is great. I really want to work with her again and go to this company. What if she left? Do you love the company? Do you love the product you're in? So I think yes is so easy to do, to say. But saying yes and really meaning it and being fully invested in it, it takes more time.

Katalina Dawson (15:44)
That's a great point. So there's a huge power in actually saying no and discovering when it is the right time to say no, even when it is kind of taking your first step by saying no. Even hearing no, I would assume that on the flip side how to take a no as a first step as well.

Michael Cassidy (16:13)
Yeah, no's are, you I mentioned the one, no's are like, no's can be pain. You fear, I think folks say yes so quick, because you're like, you just fear that rejection and that no, whether it's, and maybe it's because something, you you were rejected in the past. first example I had where it was like a hard no. And, you you had like, you're like, no, I can convince them yes. And it's like,

Katalina Dawson (16:23)
You fear the no.

Michael Cassidy (16:37)
No, the no was right. In hindsight, the no was good. In that case, they were telling me no, you have to be able to internalize it, understand it, and build upon that. But gaining your own comfort and saying no means hopefully you've thought through, you've gone through that process to say, is this what I want? If it's a new career opportunity or similar, do I?

Katalina Dawson (17:01)
That thinking through is like a way to really gauge whether the stepping outside of your comfort zone or staying in your comfort zone is worth it either way. Cause you're vetting it outside of that. You're not just going, it feels mainly comfortable to say yes. So I'm going to say yes. Or you're going, I should step out of my comfort zone. So I should say yes. It's taking a step back and like really looking at the path in front of you to decide which step is the right one for you.

Michael Cassidy (17:04)
Yeah. Yeah. You can come across some easy nos, but there are some that are very challenging. And I think it's using a network, going back to networking, know, speak to someone, ⁓ ask about the company, ask about the people, ask just for their feedback. Sometimes I love when folks reach out to me.

Katalina Dawson (17:39)
Yeah.

Michael Cassidy (17:47)
You know, and I would say if I had a person on my team or just someone I worked with, I mean, I these conversations a lot. I love when people reach out. I love that challenge of trying to figure it out, like a puzzle of like, where do think it's gonna work? You don't know the answer. I mean, there isn't like some line of question that's gonna give you this.

Michael Cassidy (18:10)
perfect answer that makes you feel wonderful at the end of it. That's less likely that happens. So you're still going to have to make a decision that could be uncomfortable and maybe you look back on it and you think, well, what if? But I think if you go through the work to get to the answer and take the time, whether that's speaking to people or doing a process, you more often come to an answer that is right at least for the time it's right. And I think internalizing and that dialogue is whether you're getting towards the yes or the no is so challenging, but it's worth so much more than the shiny object that you got with the yes. It's like, great.

Katalina Dawson (18:36)
Yeah. And leaning on the network, like you were saying, to bounce those ideas of that internal dialogue off of them. Because people in your network, whether they're their peers, their mentors who have been in the industry longer than you, they've all most likely had different paths than you have. And they might know things that you have no idea about, or maybe they've had a similar path and can help guide you. So there's so much that you tap into by using that network that you built, which is incredible. And I also want to jump back to something that you said a little while back here, but I clocked it and I was like, that is so profound what you said. At the thought of taking the first step, you said that idea in and of itself gives me a little bit of anxiety. And how wonderful though, because you're the embodiment of even though it gives you anxiety and it makes you scared, you can still do it scared. You can still take those steps. You can still vet those opportunities, say yes or say no, even if you're not comfortable, even if it's outside of your comfort zone. And I think that is so key and so profound and important to highlight that that is a key part of taking the first step is knowing that you can do it scared.

Michael Cassidy (20:02)
There's a lot of incredible people I've met in the career that on surface, they could do things like this. They could do webinars. They could do all these things. It looks so natural. You're just like, gosh, that is so... Some just are crazy natural. Let's put them aside. The rest of them are working through a process to get them...

Katalina Dawson (20:19)
You Yeah.

Michael Cassidy (20:26)
to a point that like quasi looks natural. And you're like, yeah, it takes a lot of time, but I do think, mean, everyone, there's value in everyone asking questions. I I reach out to my network. I mean, if I would not hold up my text right here, but if you looked at like the text message I have, I mean, so much of it is folks in the industry that either I'm asking completely surface level random questions or they're asking. I mean, it could be anything. It could be something major, talking, know, career development otherwise. But it could be like a new asset. You know, we're a debt buyer, a new asset we're looking to purchase. I don't know them all. There may not be folks in my company that have worked all of it, but I'll bet I can ask enough questions to find out. you know,

Katalina Dawson (21:16)
Yeah.

Michael Cassidy (21:17)
So you're keeping this rapport and this network, I think, is more developing relationships to where you can ask questions. You can learn from people. You can get very tactical things like, hey, what's this loan product like? What's this regulation change? What do you think it means? What do I think? Or you can get to this more amorphous thing of like, hey, I think I want to try something different. What do you think about this career?

Michael Cassidy (21:42)
And I think if you're developing and networking, in my view, if you're successful in that networking, you've built enough relationships that you can have those conversations. Whether it's 2 people, 12 people or whatever, think you got to find at least a couple that you feel really good. I think the better as you get further along because, you your questions get a harder to answer here. So, but all of it is around maintaining this network to help you get, know, and again, a lot of this stuff happens without anyone knowing. They're like, Mike knew the answer to that question. Well, I probably asked three people, ⁓ you know, and we're talking about like legal changes. There's like Rebecca on our team. I've asked her something. I've asked two people in her, at the law firms in her network, then I've come back and I'm like, here's an answer. You know, I tried to pretty it up. None of it was mine. I just, you know, kind of.

Katalina Dawson (22:21)
Yeah.

Michael Cassidy (22:35)
formulated it.

Katalina Dawson (22:37)
Yeah. So what about, it's not just like a simple question, but have there ever been any times in your career where you're looking at something like skill expansion, where you're looking to learn a whole new set of skills, tasks, whatever it is to really kind of grow in your career more? How would you take that first step to do that? Is it again, leaning on your network or what would you do?

Michael Cassidy (22:59)
Yeah. Yes. Again, I've kind of made a career of this. When I joined here, I took this up and joined Velocity just over two years ago. There was a good amount of what the role needed that I felt great about. And I felt coming into it like, all right, this is a solid fit.

Then there was this whole other part of what we do, which is really on the legal collection side, which I hadn't really touched it in 20 years. And the only time I was in that part of the industry, I was so junior, it was my first If I reached back to what I remember from back then, it would be of zero value to me. Actually, 20 years earlier, it would have put me in a worse spot because the industry was so remarkably different over 20 years ago. So even like I could join this, more immediately impact the things I do well. And then I had to learn or relearn the rest of it, which is, you know, this legal collections and not just how do you outsource it? How do I make sure we're doing the right thing? Well, I can't tell you if we're doing the right thing if I don't know more about it. again, I was fortunate we have an individual who, you know, directly leads that for our team.

I completely leveraged her in the beginning. And it was like, I am just going to leap of faith that like, you know what you're doing and I'm going to ask you a lot of questions and they're going to be surface level pretty But we'll try to figure it out. And I think it starts there. think there's having humility, having some honesty and like, hey, I'm not going be able to direct. I can help you with a lot of things today. And there's going to be some things you're going to have to help me with. I think any time, and that's a fairly technical like it takes time to be impactful in that space. And you have to leverage someone in a positive way, not to learn. so I think there's always someone that's in your network, in your company. You have to find an expert. And I think you have to learn from them as best you can. And then realize you don't have to be the expert, right? I did not have to be the smartest person. I wasn't going to be.

Katalina Dawson (24:45)

Yeah. Yeah.

Michael Cassidy (25:04)
which is a good thing, but you don't have to be. If you have the right folks around you, you empower them, you learn from them while you're doing it, and you support them. Again, in our industry, think you can do that. There's some more technical things. You get on the IT and some of that. It's a little harder to do, but I think starting with leveraging those around you.

Katalina Dawson (25:11)
Yeah. So in total, sounds like there's primarily three pillars for taking the first step in your career. The first one being getting to know people by just being a person. So that's like, it's a networking first step, but just getting to be with other people and like other people because people like to do business with people that they like. So building that network by being a person. And then the next step of that is, is leaning. on that network and making sure that they can come to you and you can come to them when you need something. And then the next pillar would be that power of yes, but also the power of no. And knowing how to weigh your options to really know where taking the next step is the best for you, whether it's yes, whether it's no, or even not yet, or not this time. And the last one that I think you really hit on was that you can do it scared, that taking the first step does not have to be a fully confident thing, but that you can do it terrified. Weigh their options, yes or no, and lean on your network and continue to build your network. I mean, tell me if I'm wrong, but I feel like that's what you summed up and that it's pretty straightforward, amazing.

Michael Cassidy (26:40)
No, think you've captured that really, really well. And I think on that last one, the doing something scared, I think that starts with, again, admitting it to yourself, acknowledging it. you want to call it anxiety, call it scare, call it, there's a lot of words people will put around it, but that discomfort is something I think you have to sit in for a little bit of.

Like, all right, it's here, what am going to do? So there is an acknowledgement that I think is so important on that side of it. It's not just like running scared is very different than approaching something with anxiety or apprehension or other. I think if you can acknowledge it, you can probably think through it and navigate your way through.

Katalina Dawson (27:25)
Yes, running scared versus approaching it with fear. That perfect way to wrap up our episode because we are actually at time right now. So I want to thank you so much for joining me today and sharing your experience and your insights and your story. It was incredible to have you on. Thank you so much.

Michael Cassidy (27:41)
Awesome, I appreciate this. is a great format. Thank you.

Katalina Dawson (27:44)
Thank you. Well, to our listeners, if you have any questions, comments, or topics that you would like to see us discuss in the future, please leave them in the comments below and we will always do our best to get to all of them. But thank you so much for joining us today. We will see you in our next episode. Bye.

Michael Cassidy (27:58)
Thanks.