WSO Podcast | E238: Career Gaps - Getting to Director - Cold Emails | Weekly Wrapup
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10:30 Getting To Director/MD
17:00 DO BETTER WITH YOUR COLD EMAILS
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WSO Podcast Episode 238 Transcript:
Patrick (CEO of WSO): [00:00:04] Welcome to the WSO weekly wrap up where I talk with my team about the five most trending discussions in the Wall Street Oasis community. Enjoy. All right. Welcome to another episode of The weekly wrap up. It is March 2nd. We are struggling today. We got some sick people, Nabil is out where we're going to try to have it done with just the two of us today. We'll see how we do. I can talk a lot, so I think we'll be okay. All right, Matt, go ahead and kick it off. Let's see what the three top topics are this week.
Matthew: [00:00:38] Cool. Yeah, definitely shortened roster, But I think we got this here, Pat. So first question, I know I've definitely given this some thought, earlier on in my career. So we'd love to kind of get your insights on this, but someone dropped this in the forums. How much of a career gap is too much and how can you justify that to recruiters? Any thoughts on that specifically? I know there's a common trend specifically with people coming into the industry. A lot of people I know want to take, you know, a couple weeks off Travel Europe before kind of jumping into IB or into the space. My worry was always, you know, if you're taking too much time off the bat coming off of school does raise some red flags. But what are your thoughts on that? Overall in terms of taking a gap before or jumping in?
Patrick (CEO of WSO): [00:01:23] I think you should try to take a gap. I think a couple of weeks is nothing. I think even a couple months isn't a big deal. Where you start getting into it gets a little bit more like could potentially raise eyebrows is like over three months, 3 to 6 months. You get past six months, it starts really, you better have been doing something and then you start talking over a year. Then it's even harder. But what I'll say is, There's ways to, like, prevent that. So let's say you get fired like I got fired early in my career. Usually, the person or the company firing you wants to keep things friendly. Like they don't want to fire you and have you pissed off and whatever. So usually sometimes they'll let you say you still work there while you start to search for sometimes for like a month or two.
Matthew: [00:02:11] Are they’re still paying you? I doubt they're still paying you.
Patrick (CEO of WSO): [00:02:14] No, Well, no, sometimes they'll still pay you. That can be like part of your severance and they'll keep you off for a couple months. But the point is, like ideally you're finding another job to go to prior to like having a true gap on your resume. So the gap maybe six months, but it may only look like two months on your CV and on LinkedIn if that makes sense. So like that's a big deal is like make sure when you're if you're exiting, see if you can actually negotiate that as part of like, you know, the severance where you're, you know, signing, getting a either a severance or whatever to say, hey, can I say I'm working here through, you know, let's say what is it march right now and let's say you got fired today. You could say, hey, could I say that I'm working here, you know, though, you know, through May or into May and even if you work till May 1st, for two months, May 2nd, then you can have May as like the date, is that covers you for three full months. So theoretically, if you have like a five-month gap, it only looks like a two-month gap. It's not a big deal as big a deal.
Matthew: [00:03:16] And out of curiosity, some of these numbers might change. I know you mentioned, you know, six month is okay. You know, once you start pushing them to a year, it's obviously a little bit more worrisome.
Patrick (CEO of WSO): [00:03:26] Six Month is already you're kind of, it can raise some they're gonna ask if you have six months.
Matthew: [00:03:30] They're gonna ask. But what I want to get at is because this is a nice kind of segue into just the whole macro, right? There's a lot of people that are getting laid off right now. Firms aren't as active recruiting and bringing on new talent. Do you think firms kind of understand that as well? So maybe if it is, you know, eight months, nine months, ten months, even a year, you have been proactively looking for jobs. We just haven't had any luck because of the macro situation. The firms take that into consideration. Or do you think it's more…
Patrick (CEO of WSO): [00:03:57] Yeah, they do but it doesn't reflect great on you. Like if it's layoffs, like deep-cut layoffs, there's more like understanding. Definitely not a big deal. But like, who are the who are the kids that are going to be getting picked up fastest? Like it's going to be really talented people that were cut just because there were deep cuts. So if you're still sitting there kind of 4 or 5 months later, six, eight months later, I'm a year later with nothing, it kind of is like, what's going on? What are we not seeing that's going to be going through the head? And that's why it's so hard to get another job when you don't have a job. I always say like, get your next job while you still have a job.
Matthew: [00:04:37] I think that probably comes off the back of networking, right? The idea of consistently networking never stop networking. You know, I guess you should always be networking, especially in and just naturally because you can also just be sourcing for future deals. So it's always good to kind of be making those relationships and maybe one day you do get laid off and then that or…
Patrick (CEO of WSO): [00:04:59] The fun goes south Like what happened at the fun that, like the fun had a couple big blowout bankruptcies and then like they went from 20 investment professionals down to four, like, there's no way you're avoiding that. You're cut like you're done.
Matthew: [00:05:10] So even then, another question before we segue off. This is what should you be doing if you do get laid off. Right. So obviously, there's going to be the initial shock. And, you know, I've never personally gone through it, but I can only imagine. The initial shock, you know, there's going to be a little bit of self-reflection there, kind of figuring out what went wrong, why did it go wrong. But how, you know, what should you be doing to ultimately if you didn't, If you weren't networking to find your next job while you're in your current job, What should you be doing to help increase your odds of landing a new gig in a fairly short amount of time?
Patrick (CEO of WSO): [00:05:41] Yeah. Firstly, I think a little bit of reflection, a little bit of downtime is totally normal. I think take at least, you know, first, a day or two just to reflect on like, Hey, what went wrong? Was it actually performance related? To be honest with yourself? Or was it, you know, something where it was just unavoidable and it could be either or a combination of the two? We try to really look back and think, is there something you could have done differently just to see if you can get some learnings out of that, number one? Number two, I'd say like after a week of just like, you know, watching Netflix and chilling and, you know, just feeling sorry for yourself, it's time to kind of get going and, you know, polish up that resume and make sure it's looking really good and start really, Yeah. Getting on calls, talking with people, trying to figure out your next step. And you're really trying to map kind of your next few steps. So I always say like, try to figure out where you want to end up to figure out kind of what your steps in between need to be. So it's not just like this impossible dream or possible.
Matthew: [00:06:39] It's like working backwards almost.
Patrick (CEO of WSO): [00:06:41] Exactly, You should work backwards. It's just so much easier if you're like, Hey, I want to be like this person or I want to be in that seat. You know what? If you can get on the phone, a phone call, and even have a good mentor that'll like walk you through the steps of what they think you need to do and then follow up and actually execute on that. I think it just shows, yeah, I think you're going to be in good shape. But you just you don't want to be sitting around and feeling sorry for yourself for several months that should be time spent, like building out the connections, making sure you're getting into interviews, getting sharp on your interview skills again, because that may be rusty because maybe you haven't interviewed for a couple of years. So…
Matthew: [00:07:17] Taking WSO’s prep courses.
Patrick (CEO of WSO): Yeah, of course.
Matthew: Financial modeling skills. And even yourself.
Patrick (CEO of WSO): [00:07:25] Financial modeling skills. Yes, but like even more so just the interview prep, like making sure your stories are tight. And then more very importantly, like, what if it is performance-related or culture related, like the firing or the being let go, kind of being very polished around that specific answer? So if you're let go, you don't have to get like into super deep details, but you can say, you know, my previous seat was here. I think things went really well. I moved to this firm thinking that I was going to be doing X, Y, and Z. It was a little bit more of this, which I don't think was a great fit for my skill set. And culturally, I don't think we meshed well and I think it was a mistake on my side for not doing the diligence beforehand. So if you can be a little bit like forthcoming, like not just blame the company, I think that comes across well, and being humble, like, you know, I really think but I do really think this role or this firm is a much better fit for me because of X, Y and Z. You know, it's more similar to my previous role where I really excelled and blah, blah, blah, blah, blah, something like that, where you're able to kind of tell a believable story of why it didn't work out. I think it's good you don't want to harp on it and be like, Oh, I really messed up and da da da and, you know, or talk trash about the previous. That looks bad. So you kind of, you need to kind of thread the needle a little bit and make it seem like you're mature and humble.
Matthew: [00:08:42] And so you definitely, at the end of the day, have to prepare for the conversation, I think is…
Patrick (CEO of WSO): [00:08:46] Yeah, You don't want to. Yeah, you're going to be asked.
Matthew: [00:08:47] Make it short, concise, but have that ownership own up to it and then, you know, show how you've kind of changed your process of, you know, looking after or looking over a next potential career opportunity and why you think this is a better fit. One question I did want to ask before we move off to the next topic. Yeah. What are your thoughts on, on a on a LinkedIn post? I've seen some pretty cringe ones when people get laid off. Should we be doing that? What are your thoughts on that? It seems sometimes like a little bit of a pity party. What do you think should be posted on LinkedIn along thread…
Patrick (CEO of WSO): [00:09:21] If it's like if you've been at like Google like for ten years and you want to make a post about it, I don't think it's a big deal. I think it's fine. I think if anything, being forthcoming that might actually help you in terms of getting opportunities thrown your way, especially if you're coming from like a top brand. It's just kind of announcing the world as like, I'm on the market. You know what I mean? And then suddenly you may not have to do as much networking. It may come a little bit to you if you have some followers and stuff like that. But yeah, if you've only been at a place for like a year or two, it's kind of silly and I'd prefer to do it privately so that you don't have that record kind of there. Let's say you want to go back and be like, let's say six months later you don't have anything. You're like, Shoot. Like, can I stretch that?
Matthew: [00:10:04] I have seen that happen. Sometimes, though too. People leave and then, you know, a year or two later they do come back. So I think at the end of the day, definitely don't want to burn your bridges. I think I agree with you on that. Yeah. If you've been at a business for only, you know, a few years, probably doesn't warrant this long-word essay on, on why you got fired. I think it's just, at the end of the day, pretty common. Everyone gets fired. Not everyone, but it's definitely a common situation so I wouldn't hang your head too low but great convo there. Let's move on to the next topic here before we run out of time. This is what I said to my team, but we both like to talk here so we could go on forever. I think this one's right up our alleyway here, specifically around spending time in investment banking, you know, And you know, the common theme here is spend two, three years in investment banking and, you know, you find your exit off, whether it's into the hedge fund space, private equity or become an entrepreneur. But shockingly, there's a few people that actually enjoy the work and want to stay and kind of move up the ranks there into, you know, director and becoming an MD. And one of the questions was, you know, how does that process take place, making the jump from VP to director, You know, what does it really entail? I think we all understand, you know, how to move up from analyst to associate even to VP. I think that's pretty common just naturally because of a lot of people do make that jump, but then there's less people making the jump to becoming an MD. So there's a lot less visibility in what that actually takes. So we had some members discussing that. Pat, what are your thoughts on how to make that, you know, a reality?
Patrick (CEO of WSO): [00:11:35] Yeah, I think the job is super different from like even from analyst to VP. It becomes from like, you know, grunt processing docs and PowerPoints and models to kind of managing the grunts at the associate level to. You're still doing some of that, that associate-level work where you're having to kind of manage processes. But at VP level you're kind of expected to start sourcing and becoming more of a sales role, which is a really tough transition. If you think about it, it's like completely opposite skill set of what you've been doing. Like it's an internal like yes, you're meeting clients and whatnot and shaking hands, but you're not actually driving the business into the firm. So. Yeah. So I think it's a very hard transition. I think a lot of people struggle from that jump from associate to VP and then at the VP level, they're kind of all the MDs and the directors are all looking at you like, okay, you know, are you sourcing or how are you sourcing here? Build your business. And I think the skill set here is all about, you know, reaching out to building relationships with actual executives, CFOs, CEOs of, you know, ideally within a specific niche so that they come to know you as a trusted advisor. And they're you when they hey, when they want to make an acquisition or they want to sell a specific division or whatnot, they're going to come to you first. So that's kind of the. That's the bridge you need to make. Instead of like, it just being solely focused on process work and putting together a great deck and going and just shaking hands, it's like actually going out and meeting new people and like somebody said, you know, sourcing deals outside the company network. So you're bringing additional value and additional revenue into the firm. So…
Matthew: [00:13:15] I was going to say, I think actually the harder part. I know you mentioned obviously is taking away from the mindset of process driven and going into more relationship building. But I think what I would envision being pretty hard is, you know, as you kind of move into that relationship building sales oriented mindset is you're now speaking or trying to get business from the true industry professionals, right? If you don't have that background, say, for instance, where you're, you know, you want to become an MD on a mining team that I'd be mining, the people you're going to be speaking with, there are like geologists, people like they know mining from top to bottom, whereas, you know, you maybe just studied finance in college or university, did your time as an analyst associate. But at the end of the day, it's making sure that, you know, you're as well versed on that industry as the actual professionals, professionals are that have built a thriving business and have maybe spent upwards of 40 years in it. So I find maybe. Do you is there any suggestions on maybe, you know, some personal development, whether it's, you know, getting some additional schooling or…
Patrick (CEO of WSO): Yeah, it's interesting. I mean.
Matthew: It's anything to…
Patrick (CEO of WSO): [00:14:23] I mean, for super like niche things like mining and or like fig or where, you know, I think if you've already been in banking for like 7 or 8 years covering the industry, you're probably are pretty knowledgeable. I think the key here is that you're likable and trust it and trustworthy like that. These executives want to go for you for that financial advice for that. That's more important than like them thinking, you know, every little last thing as much as them. Although you should be up to date on the industry trends, you should be able to like give them some insight, if possible, on what's going on, because sometimes their heads down in like the operations of the business, and maybe you can add some value. So you got to be likable, you got to be personable, you got to be, you know, building that trust over time.
Matthew: [00:15:05] I guess this is when you get to spend the company credit card a bit more, right? That's when you get to in the little wining and dining, taking clients out about obviously being like…
Patrick (CEO of WSO): [00:15:16] I mean, it can take years of that. And like sometimes a lot of I think a lot of bankers stall out at that VP level because they can't make that transition. Right? And it's kind of almost like an understanding, a requirement to get to that MD level of like you need to start actually bringing in business to the firm. So. I think it's hard. It's a tough business. But if you're really good at process work, sometimes the bank will keep you on at the VP level for a pretty long time, and you can still do pretty well.
Matthew: [00:15:47] Yeah. Oh, for sure…
Patrick (CEO of WSO): [00:15:50] And if even if it takes five years, seven years to really build those relationships like that's, you know if you have an MD that's kind of like older, that's kind of looking to slow down anyways, he can kind of hand those off over several years. And so they're getting to know that team of like the VP and that VP can slowly kind of move into that seat where they're, they're kind of taking the role of the MD as the MD slows down and eventually retires. Although. Sometimes MDs work till they're…
Matthew: [00:16:18] I was going to ask…
Patrick (CEO of WSO): They drop dead.
Matthew: The work-life balance. They're a little bit better on the MD side of things where…
Patrick (CEO of WSO): [00:16:25] They're a little more control like of where you work and like when you work. But there's just a lot of traffic, there's still a lot of travel, even more. Yeah. So it's still tough.
Matthew: [00:16:35] Is it still upwards of like 70, 80 hours a week, you think?
Patrick (CEO of WSO): [00:16:38] No, I mean, some people are like maniacs and do.
Matthew: [00:16:40] Just because they love it and they have no other outside passion.
Patrick (CEO of WSO): [00:16:43] And they're getting a cut like they're getting a cut of what they're bringing in. Typically they have negotiated agreements, So, yeah, they'll still sometimes go crazy. But yeah, I'd say probably more typical is like 50 to 60 at that level. Yeah.
Matthew: [00:16:56] So right on. All right. Well, let's hop on here to the last topic. I think this is nice. It kind of takes pieces from the first two discussion topics, but around ultimately, you know, networking and cold emails. I know me myself, obviously being responsible for a lot of the sales initiatives here. I understand the importance of personalized emails. So I can maybe touch on this a bit. But, you know, ultimately the question posed here is how to write cold emails that actually get responses. So do you want me to give a few words here? Then I could chime in on what I think works best.
Patrick (CEO of WSO): [00:17:28] Yeah, I have a lot to say on this stuff.
Matthew: [00:17:31] Do you want to even reference that one email you hit me up on about three weeks ago and were shocked on…
Patrick (CEO of WSO): [00:17:38] Yeah there was a I can't remember what the company was. I think it was a credit card company like ramp one of these business credit card companies and I was pretty shocked at like the level of detail that the sales associate went to. They were like, Hey, I noticed that you're a Williams alum, Purple Pub. They're like mentioning the pub like downtown, like I'm headed over there.
Matthew: [00:17:55] It was to the point I think you asked me, like, do I know this person? Like a little bit concerned.
Patrick (CEO of WSO): [00:18:01] Well, it was just so detailed about like it was really like smart going into the details of like the school of my undergrad. Almost like, it brings up a nostalgia, right? So it's like a very smart little angle there. But like people can use this for career cold email. So like I think this thread was all about like it was super generic or whatever. Like what I say is you have to balance, you have to balance cold emails in terms of like personalization and efficiency. And so it depends like if you go to like, let's say University of Texas or like a large state school with a huge finance program, I think trying to write like a tailored, super tailored email or initial intro email to every single one of those people, it actually is probably a little bit of a deterrent when you already know their alums, you can say, Hey, I noticed you put out a Dada, you're an alum of this. And I went here and I noticed you're at this bank. So being a little bit more specific in that cold email to show you've at least read it, it takes like an extra ten seconds and probably would take your response rate from like 5% up to like 15, 20 percent? I think it's worth that extra few seconds versus like if you're just, you know, filtering through, let's say you have like 3000 contacts you want to hit up because it's just a more generic filter for, I don't know, investment banks and like investment bankers and um, I don't know LA or something like that.
Patrick (CEO of WSO): [00:19:26] And so like it's a bigger group and you, you can still mention LA and how you want to be there and da da da, it still seems a little personalized if you mention the company, but you don't have to be like. Hey, let me see where they went to school. Let me talk about the pub that they went to like undergrad. Like, you know, they didn't have to go to that level because I think you're going to end up not getting through that because, you know, even if you get through that whole 2000 list and your response rate is only 10%, that's 200 people getting back to you, That's probably about 20 calls that you're going to be able to get on. And I'd rather the person do that rather than, you know, not even get through that list of 2000 because they're trying to send a person like a huge personalized thing, and the cold emails, they should be super short initially. And then once they connect with you, that second email, that should be more well-researched.
Matthew: [00:20:12] Yeah, that's exactly what I was going to say jar at some points here, I would say one best practice that I learned is called three by three, three minutes for three pieces of information and you'd be shocked. It's pretty easy. Like, you know, you hear three minutes, you think that's an incredibly short amount of time. You know, it's if you're looking at the right places, it's extremely easy to find three personal things to point to. And I would suggest simply just even like LinkedIn right off the bat, a lot of the points you mentioned all the matter bank they're currently working at, even just previous work experience and sometimes even the groups that they follow there, you have visibility into that interest. Sometimes that might be something to reference there, maybe following a certain sports account or retailer of some sort that you can maybe point to. The second place I would suggest to look at is always the company news page. Like when you're on their website, you go to news, you could reference maybe a deal that was they've announced or possibly a new hiring, something of that nature, it's very easy. Three minutes, three pieces of information.
Matthew: [00:21:13] And you incorporate that into your emails to your point. First, outreach email should be short. You definitely don't want to be having, you know, two 300-word emails. It's just not going to get read. At the end of the day, people keep their time close to them. So, you know, for someone to spend even just a few minutes reading emails, you'd be surprised. People are getting emailed all the time, from various vendors or just, you know, people wanting networking calls. unless you're in that position, you won't realize that. So being on the other side, being the person trying to do the outreach, you have to understand that these people of in these high-level roles are getting, you know, upwards of 20, 30 emails already a day out, you know, cold emails. So it's how to differentiate yourself and the and the way you do that, I think is in the subject line. So it's keeping the subject line light but also unique where it's going to stand out and it's going to make them interested in opening up the email because, at the end of the day, that's step one. You know, again, with the idea of…
Patrick (CEO of WSO): [00:22:10] Copywriting 101 man, Copywriting 101
Matthew: [00:22:12] The idea that I kind of mentioned earlier of just like working backwards, it's the same thing. If you want them to hop on a call with you and you know, ultimately buyer your service or go on a coffee date for networking purposes, it all starts with them opening up your email. So how do you do that? Good subject line if you just get it that granular.
Patrick (CEO of WSO): [00:22:30] What's an example of a good subject line for like, what would you say for a networking? And we go through all this stuff in a WSO Academy, which we're going to talk about. So, but…
Matthew: [00:22:40] I think…
Patrick (CEO of WSO): [00:22:42] We have template, we have hundreds of templates that work. But yeah. What do you think?
Matthew: [00:22:47] Yeah, Personalizing the subject line, incorporating even just their first name, somehow incorporating maybe their alma mater. You know, it could be something like, you know, way they went to. Yeah, William Sophomore looking to get in touch with, you know, or discuss XYZ, whatever. It's personalizing the subject line, keeping it short, I think is extremely important. And one little thing I like to do is including the regarding thing at the beginning so it looks like to them that they've already opened the email so they're more inclined to open it again. It's a little trick sales trick.
Patrick (CEO of WSO): [00:23:26] I think people get pissed at that sometimes.
Matthew: [00:23:30] At the end of the day, Pat, they're opening up the emails which is the end goal. I haven't in my, I would say what four years now of sales experience altogether, Five years. I haven't gotten anyone saying what the hell is going on with this regarding so I'll keep doing.
Patrick (CEO of WSO): [00:23:46] You mean the Yari colon?
Matthew: [00:23:47] Yeah, the Yari colon. It's just, it's a little mental trick again because it's to them, it's like, well, I've already opened this, right? But I think at the end of the day, main themes should be personalizing the subject line. Like we said, William sophomore, looking to grab a coffee. Dot, dot, dot. And I think, you know, that already looks a little bit more personable…
Patrick (CEO of WSO): [00:24:10] You know like, even like some of the tricks in copywriting. Around piquing curiosity, a little bit can work as well. So like William sophomore with three or with two questions or something like that. And they're like, What are these questions? You know what I mean? It doesn't sound like a lot. They're suddenly they're going to want to know what those two questions are. And it could be like, you know, one, how can it be as successful as you two? Can we have a short chat? or something like that. You know, you stroke the ego a little bit or maybe it's something like, hey, number one, you know, when is the best time for you? And number two, I don't know, something around just working around their schedule. It can be really casual, short, kind of fun. It can be a little funny, you know, obviously not goofy or like unprofessional, but…
Matthew: [00:25:00] Yeah and one of the team did want to mention is also just the idea of, you know, having a little bit of a process around it and keeping track of results, I think is important because especially if, you know, you're going to you know, you have a target list of, say, three, 3000, you know, bankers in LA, like you mentioned that situation. you don't want to just stick with one outreach for all 3000 and then realizing after, oh, you know, it didn't work. I wasn't as successful as I'd hoped. I hoped it went. I think the better way to tackle that is, you know, you start with 150 individuals, have a certain outreach email, see what the conversion on that looks like. You know, you did 150. Yeah, you got a 40% open rate of which 20 responded, of which, you know, three said, Sure, let's have a time to chat. That's great. Then you could just obviously then, you know, do that for the remaining amount of people and you can then anticipate, you know, what type of results you're going to get. It's helpful. On the flip side, if you do 150 and you get two responses and not a single person has said, Yeah, sure, let's have a chat. So that's where you want to change things, start changing things, and see then where the success.
Patrick (CEO of WSO): [00:26:04] Yeah and you can even split test, you can split test by sending 102 versions that you're not sure which one's going to do better that have been, you know, really tailored and you've taken time to really think about like, okay, if I was in this person's shoes, I'm not sure which one would do better and usually the subject line can be the differentiator is almost like, I mean, yes, every piece matters, but like the subject line sometimes can be like the difference between like a 30% open rate and like an eight, a 70 or 80% open rate. Like it's a really good subject line. So that's, that can be like A2X difference in your response rate and your bookings, your informational interviews, which is kind of the goal here to build those relationships so you can get more interviews and more offers so…
Matthew: [00:26:43] Yeah, Exactly. So I think, yeah, main themes here are just being personalized the email, Don't got to spend a bunch of time on it, you know, three minutes, three pieces of information. Keep it short and sweet, but then also do have a process around it where you're staying nimble and able to make changes on the fly to this outreach approach. Ultimately at the end of the day, just to get some good results but yeah, I think that's it from my end of things I think great combo today Pat with a short bench but I think we'll wrap it up here and we'll look forward to chatting with everyone next Thursday.
Patrick (CEO of WSO): [00:27:17] All right. Thanks, guys. And thanks to you, my listeners at Wall Street Oasis. If you have any suggestions, whatsoever, please don't hesitate to send them my way, [email protected] and till next time.
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