What Does Taking the First Step in Your Career Really Mean? | Ep. 27

What does taking the first step in your career really look like when the path isn’t clear?

In this episode, Katalina Dawson sits down with Michael Cassidy of Velocity Investments, LLC to break down how to evaluate a career opportunity, build authentic relationships, and grow through career networking in receivables.

From stepping outside your comfort zone to building trust-based professional relationships, this conversation is packed with practical insights you can actually use.

If you're ready to make smarter career moves, this one’s for you: hit play and let’s get started.

Podcast Website:
https://careerpathpodcast.com/taking-first-step-career-cassidy/

Guest Website:
https://velocityrecoveries.com/

Guest LinkedIn:
https://www.linkedin.com/in/mjcassidy/

taking the first step in your career,
career networking in receivables,
how to evaluate a career opportunity,
building relationships for career growth,
career growth through industry relationships,
authentic networking for career opportunity

#takingthefirststepinyourcareer #michaelcassidy #careernetworking

Transcript

SPEAKER_01 0:10

Hello and welcome back to another episode of Career Path. I am your host, Catalina. 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.

SPEAKER_00 0:35

No, thanks. Thanks for having me. I'm excited.

SPEAKER_01 0:37

Awesome. Well, I'm going to 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.

SPEAKER_00 0:45

Yeah. I'm uh I'm based here in New Jersey, also where our company, Velocity, is headquartered. Um, my wife and I returned back here in 2017 uh after a 12-year escape for me, uh, eight-year for my wife. Uh came back to be closer to family uh and start our own family. We now have two kids. Uh kind of my career, um, I think mine started like many or probably most in this industry with zero intent to to end up here. Yes. For for better or worse. Um, you know, I answered a newspaper ad, which ultimately led me to a New Jersey uh creditor rights law firm right after college, to my father's disappointment. But I mean, that that two years I spent there really helped kickstart this, you know, kind of an accidental into the industry. You know, after about two years in uh with the law firm, in lieu of taking a promotion, I kind of had that that first bit of anxiety, if you will, of I don't know if I want to do this, I don't know if I can stay here. Nothing against a 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 for better or worse, it ended up being better to jump out and take my first move. So instead of taking the promotion, I made the leap about two hours south to Delaware, not a huge move, but I ended up being a really great career move to jump over to the card issuer side where I spent really the next eight plus years. And I was fortunate. I mean, that that move allowed me uh through really great leaders making very poor decisions to take on a whole bunch of opportunities that I probably wasn't, you know, initially equipped for. You know, 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 going to 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. Um went 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 and network, which we'll touch on a little bit later, but allowed me to expand beyond just the company I was working with and working for, and start to meet other companies and it 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 uh sister companies, one out in in Stockholm, Sweden, uh, and another one in Germany to consult, if you will, or try to help uh 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. Uh, you know, I really loved the Stockholm opportunity, applied for a permanent role, learned uh a bit of humility that I was not prepared for it. Uh, 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, you know, 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. You know, that led to a year later, I decided to go back on uh the agency side instead of the law firm. Uh two, two and a half years running US operations for a uh collection agency. Another great opportunity, understanding more about PL, more about you know, profitable doing collections as a profit versus doing it uh for for protecting your losses on the issuer side. And that one I love because it it's you know, you try to fast-forward it to kind of how I got here. That one, just through networking, you know, maintaining a network of individuals. I had a former mentee of mine that the bank had a program running, you know, reach out to me randomly saying she wanted to get out to the Bay Area. Did I know any companies? And I and I 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 her, great. If you don't, I'll never mention it, uh, your name to her, and we'll just you know move on. And just that random outreach not only got her hired, her relocated Bay Area where she wanted to go, but I, you know, accidentally got me uh a role to build out collections recovery and relocate my wife and I to the Bay Area to join Prosper, you know, pretty early uh in the fintech uh days. And that accidental, which I guess is a sad definition of a lot of what I've done, that that accidental success was 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 you know now basically blown up. That's where, you know, 10 2014, when I first met Jim Mastriani and the Velocity folks, uh, they were one of my earliest uh entities we sold debt to. I met the two individuals who in 2019 I would eventually leave, prosper, and start a consulting firm with, uh just kind of building off that network and ended up, you know, 2024 joining here at Velocity. So that's been a lot of uh accidental success, I'm gonna I'm gonna call it.

SPEAKER_01 6:04

Yeah, a lot of a lot of twists and turns and even some international opportunities, which is incredible. But I I completely understand not wanting to change your like 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?

SPEAKER_00 6:34

Yeah, I I I think it's it's done almost everything to it. You know, I call it this accidental, a bit of an accidental success, but it's not really 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've I always thought networking of this, you know, out introduce your elevator pitch and doing this, like that was never natural to me. Yeah. And I think as I gained experience and gained comfort, a lot of learning from others, you learn to kind of find your version of networking. Mine was just developing relationships. I love 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 liked 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. Um that's kind of how I got it.

SPEAKER_01 7:38

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 it 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?

SPEAKER_00 7:59

I think it's more challenging. Um again, for a personality like mine or or um I find it more challenging, right? So my version of networking again was developing a relationship. And I think that's really nothing is easy to do, but I think when you're in person, you're working with, you know, your colleagues in an office, it becomes very natural. You know, you just develop like you were in school, you know, 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, other, even within a company, move to other departments, learn other things, uh, 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, I think it's, you know, 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 like Zoom, or you're on something else. It's very like 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. I think like anything, it can be overcome. You just have to tweak it. You have to make sure you you have time to develop a personal, you know, dialogue or conversation. Conferences, I think, are wonderful opportunities if you gain comfort navigating them. I think it's certain conferences, you know, you can get overwhelmed or kind of kind of swept up in it. But yeah, I do think it's more challenging. I think it's it's gotta be more conscious now than it was maybe when I was when I was uh building my career.

SPEAKER_01 9:47

Have there been any programs along the way that kind of helped you take those first steps in initiating?

SPEAKER_00 9:52

When I was doing it, mine was really, I'll speak to a program that came afterwards, but mine really was very much this like uh this personal development. And I and I think that large occasion, I can't call it a it's not a program, but I think you you leveraged your your leaders finding your your mentor, if you will, and yeah, watching and emulating, emulating in some cases, trying to do completely the opposite in others, but but you find ways to learn from folks. How do they ask questions? How do they start a conversation that's not doesn't feel like that that that like uh elevator pitch, if you will, where where you're just immediately going into the product you're selling, or or you know, how do you make it sound natural? And I think you can do that by watching others always, whether you're you're you're remote, you're in office, you're at a conference. I think you if you find the right folks and really pay attention. Although I think you can learn, you can learn from anyone. Uh, you know, 100%.

SPEAKER_01 10:51

You can always learn what not to do as well as what to do.

SPEAKER_00 10:55

Yeah, make making sure it fits your your personality. Um, you know, my my approach is, you know, probably very awkward for for some people. I like to make everything about some, you know, personal conversation or a sarcasm or like that's not one that will not naturally work for everyone, and it won't be received well by everyone if you if you're not careful in how you use it. So I think you you learn, you try to learn whether officially or unofficially from from those around you. I did take part in a program that I I I enjoyed for I think three years. Um, and this was in the COVID post-COVID uh time of the university I attended, did a pretty cool, which I'll bet is more common now, but you know, for the first year business students, they 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 know, 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. But but yeah, I I think I 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 gonna go to a conference and network, yeah. It's probably not gonna work all as well as you think it will.

SPEAKER_01 12:31

100%. Now, outside of networking, how would you define that taking the first step in your career and how do you embody it?

SPEAKER_00 12:39

I mean, even just the concept of hearing like taking the first step gives me anxiety. No, I I I think you you know, I think you have to start with there's no blind first step, you know, it's it's finding a direction or something that you want to work towards.

SPEAKER_01 12:55

Like an opportunity?

SPEAKER_00 12:57

An opportunity, yeah, it's it's a great one, right? Find the right opportunity. Then then you're internalizing, 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. I was, you know, kind of the right place at the right time. But whether you seek it out or it kind of finds you, it it I think that 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? Versus that initial. I think we're often people pleasers. You're like, yes, I should, it's an opportunity. I should take it. You should probably think about it a little bit more.

SPEAKER_01 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.

SPEAKER_00 13:43

Yes, I I think entirely. And I see this a lot again, you know, my my version of networking is maintaining relationships, right? When I was consulting for the five years, we didn't have like a we didn't have like a sales engine. It was like leveraging our network of people we knew and just having a conversation and hopefully something came up and they're like, oh, I forgot Mike existed. Maybe there's this thing we could do together. But I think getting that comfort of of all right, let me think through what do I want to do. Uh you learn how to probe, you learn how to like just ask questions. I find it with with a lot of my network now, though they'll reach out or I'll talk to them and say, hey, I have this really great opportunity. Um, I think I'm gonna take it. Um and then you're like, oh, cool. And and you sit back and say, All right, what is it? What's the company? What's the role? What's the industry? It's in. And you try to help people as best as I can, if if they even want to. You try to help them sometimes think through like, does it follow the logical narrative for your career? And that's not a it's not me to decide for someone. I I love helping people get towards that, which is are you are you pursuing something that's logical, that's building on upon something you've already done and keeping you and I think you find in a lot of folks it's um it it's just the excitement of something new or a title or compensation. I mean, all things compensation certainly matters, title and never want to celebrate a title, it's just not not my thing. But I I think folks can get swept up in what they think is a great opportunity and not go the the levels deeper to say, is it logical? What happens if? What if you don't like it? Uh do you do you do you just know one person there that you were like, oh Catalina's great? I really want to work with her again and go to this company. Well, what if she left? Do you love the company? Do you love the product? Like so, I think yes is so easy to do, to say, but saying yes and like really meaning it and being fully invested in it, it takes more time.

SPEAKER_01 15:56

So there's a huge power in actually saying no and discovering when it is the right time to to say no, even when it is kind of taking your first step by saying no, even hearing no, I would assume. On the flip side, how to take a no as a first step as well.

SPEAKER_00 16:13

Yeah. No's are, you know, I mentioned the one, no, no's are like those 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 uh, and maybe it's because something, you know, you you were rejected in the past. Like if that first example I had where it was like a hard no, and you know, you had like you're like, no, I I can convince them yes. And it's like, no, the no was right. You know, hindsight, the no was good. Well, in that case, they were telling me no, and you have to be able to internalize it, understand it, uh, and and build upon that. But gaining your own comfort and saying no means hopefully you've you've thought through, you've gone through that process to say, is this what I want? Is this, you know, if it's a new career opportunity or similar.

SPEAKER_01 17:00

You know, 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, because you're vetting it outside of that. You're not just going, I it feels mainly comfortable to say yes, so I'm gonna say yes, or you're going, oh, 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.

SPEAKER_00 17:29

Yeah, and it and it you can come across an easy nose, but there are some that that are very challenging. And I think it it's using a network, going back to networking, you know, speak to someone. Yeah. Ask about the company, ask about the people, ask just for their feedback. Sometimes I love when folks reach out to me, you know, and I I would say it if if I had a person on my team or just someone I had worked with. Um, I mean, I have these conversations a lot. Um, I love when people reach out. Just I love that challenge of trying to figure it out. It's like a puzzle of like, are you thinking it's gonna work? You don't know the answer. I mean, there there isn't there isn't like some line of question that's gonna give you this perfect answer that makes you feel wonderful at the end of it. That's less likely that happens. So you're still gonna have to make a decision that could be uncomfortable and and you know, maybe maybe you look back on it and and you think, well, what if? But I think if you 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 that is right, at least for the time it's right. And I think I think that internalizing and that dialogue is whether you getting towards the yes or the no is is so challenging, but it's worth so much more than this shiny object that you've got with the yes. It's like great.

SPEAKER_01 18:50

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 how wonderful though, because you 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.

SPEAKER_00 20:02

There's a lot of like incredible people I've met in the career that like on surface, they could do things like this, they could do webinars, they could do all these things, and it it looks so natural. And you're just like, gosh, that is so uh they're sorry, some just are crazy natural. Let's put them aside. The rest of them are working through a process to get them uh to a point that it like quasi-looks natural. And you're like, yeah, that that that it it takes it takes a lot of time. But I I I do think, I mean, everyone, there's value in everyone asking questions. I mean, I I reach out to my network. I mean, if I would not hold up my my text thread here, but if you looked at like my the the the uh the text message I have, I mean, so much of it is is uh 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, we're talking, you know, uh career development otherwise. But it could be like a new asset. I mean, 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. Yeah. So you're keeping this rapport and this net 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 this loan product like? What's this regulation change? What what do you think it means? What do I think? Or you can get to this like more amorphous thing of like, hey, um, you know, I think I want to try something different. What do you think about this career? I and I think if if you're developing and networking, in my view, if you're successful in that networking, then you've built enough relationships that you you can have those conversations, whether it's two people, 12 people, or whatever. I think you you gotta find Find at least a couple that you you feel really good. I think the better as you get further along because you know your your questions get a little harder to answer. You're so, but uh, all of it is around maintaining this this network to help you get, you know, and again, a lot of this stuff happens without anyone knowing. You're like, oh, Mike knew the answer to that question. Well, I probably asked three people.

unknown 22:21

Yeah.

SPEAKER_00 22:21

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 formulated it.

SPEAKER_01 22:36

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?

SPEAKER_00 23:01

Uh yes. Again, I've I've kind of made a career of this. When I joined, when I joined here, you know, when 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, this is 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 role. If I reached back to what I remember from back then, it would be of zero value to me. Uh actually, 20 years earlier would have been it, it would have put me in a worse spot because the industry was so remarkably different, uh, you know, over 20 years ago now. So even like I could join this, I could 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. Um 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. And again, I was fortunate. We we have an individual who, you know, directly leads that for a tune. I completely leveraged her in the beginning. And it was like, I am just gonna leap of faith that like you know what you're doing, and I'm gonna ask you a lot of questions, and they're gonna be surface level pretty dumb. But we'll try to figure it out. And I think it starts there. I think that there's having humility, having you know, some honesty, and like, hey, I'm I'm not gonna be able to direct I can help you with a lot of things today, and there's gonna be some things you're gonna have to help me with. Um I I think any any time, and that's a fairly technical, like it takes time to be impactful in that space. Um, you have to leverage someone in a positive way, not to learn. So I I think there's always someone, whether that's in your network, in your company, you have to find an expert. Uh, 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 I did not have to be the smartest person, I wasn't going to be, which is a good thing, because um, but you don't have to be. Uh if you have the right folks around you, it you know, you you empower them, you learn from them while you're doing it, um, and you support them. And I again in our industry, I think, I think you can do that. Uh, there's some more technical things. You get on the the IT and you know, some of that, it's it's a little harder to do, but uh I I think starting with leveraging those around you.

SPEAKER_01 25:29

Yeah. So in total, it 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 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. Um, 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.

SPEAKER_00 26:40

I think you're I think you've you've captured that really, really well. And I think on that last one, you know, the doing something scared. I think that starts with like again, uh admitting it to yourself, like acknowledging it is because you want it, they call it anxiety, call it scare, call, you know, there's a lot of words people put around it, but that discomfort is something you think you have to like sit in for a little bit of like, all right, it's here, what am I gonna do? So there is an acknowledgement that I think is so important on that side of it. It's not just like running, uh, you know, running scared is very different than than um you know, approaching something with with anxiety or or apprehension or other, you know. I think if if you can acknowledge it, you can probably think through it and and navigate your way through.

SPEAKER_01 27:24

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, Michael, I want to thank you so much for joining me today and sharing your experience and your insights and your story. Um, it was incredible to have you on. Thank you so much.

SPEAKER_00 27:40

Awesome. I I appreciate this. This is a great format. Thank you.

SPEAKER_01 27:44

Thank you. Um, 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.

unknown 27:58

Thanks.