Speaker 1You can't hire sales to come in and solve a product market fit issue. There's plenty of CEOs that are like, we want to grow, you know, 150 or 200% next year. And they think that hiring more salespeople or more AEs is going to solve the issue. And it really is a demand issue. And demand is still the oxygen for growth.
Speaker 2Just wrapped up a great episode with Brendan Cassidy. He runs Cassidy Ventures. In the conversation, we talk about some of the most common mistakes he's still hearing these AI natives make. If you don't have tailwinds and product market fit,
Speaker 1I don't know that AI has figured out a way to be like, you don't have product market fit. Nobody f***ing cares. If nobody wants to buy your products, it's hard to solve that problem. We also talk about best practices around interviewing salespeople. Salespeople are pathological liars, generally speaking. And so when you're like, I'm optimizing for all these traits, right? And you're like, well, okay, they're probably lying about most of it. I don't care what your LinkedIn profile says in a lot of ways. And this concept around game tape being king. What's your game tape today? I want to see what's your pitch. Who do you think is good is less relevant to me. And what I care about is just like.
Speaker 2Welcome to the crew podcast, where we have conversations with the top go-to-market leaders at AI natives and SaaS startups. I'm Chris Belestris, co-founder of crew, a go-to-market recruiting, media, and investing firm helping seed through series D AI natives grow. Now on to the episode. Shout out to a sponsor of the crew podcast, MetaView. MetaView. Hiring is the highest leverage thing any leader does. As they say, the team you build is the company you build. That's why over 7,000 companies from startups to the fortune 500 hire on MetaView. MetaView gives hiring teams, AI agents that do the recruiting work for them. Finding candidates, reviewing every application, capturing every interview, all in one shared workspace. So teams make faster, better hiring decisions. Don't let your competitors out hire you. MetaView customers close roles 30% faster. Check them out today at MetaView.ai. Big thanks to our sponsor attention. Sellers were hired to sell, not to fill in the CRM. Attention records and understands every sales call, then automatically updates your CRM, sends follow-ups and scores reps against frameworks like medic, bant, or your own custom methodology. Next best actions are proactively generated from there. You get a clean pipeline coaching on every call and forecasting. You can actually trust without asking reps for more admin, turn your call recordings into a GTM. Operating. You can get a free training layer with attention. Try them today at attention.com. Brandon, thanks for coming on the crew podcast. I know you don't do many of these. I've been a fan of yours for a while. I was religiously would watch Harry's pod and grit and 20 sales are the two that like a lot of people compare our podcast to sure. Quite the claim to fame 13th employee at LinkedIn. That's pretty wild 13th to 20th to 25th there's actually, nobody will round down. Nobody knows the actual scorecard, but yeah, it's somewhere in there. Yeah. Well, we'll talk about recruiting in this and just interviewing salespeople, but we'll talk about that a little bit later. We're going to talk a little bit more about what you've done in the past and what you've done in the past and what you've done in the future. Yeah. Yeah. I mean, I've done a lot of things in the past. I've done a lot of things in the past where I've been recruiting as the market turned when you were there, you said, you know what, I want something with in your Bay area native. So getting a tech sales and you had some great runs at 13 to 20, the employee at LinkedIn, you then with Jason Lemkin ran sales at Echo sign and then talk desk and now running Cassidy ventures, which is operating, advising, investing in some of these companies. A lot of people, I feel like should know who you are. You're kind of a big wig in like the sales space. You'll do a better job of explaining your background in an elevator pitch.
Speaker 1So just, uh, just a lucky guy. That's just stringing flukes together. That's how I feel. I actually don't feel like I'm that big a deal or that I'm that successful. And I think, you know, I think staying in the startup world, it's pretty good not to get a big head about you because, you know, sort of every client I go into, I'm always like, this could be the one where I just can't help. Right. And they're like, oh, we thought you were going to come in here and help, you know, move the needle or, or change whatever. And I'm always. Like, you know, this could be the one I could be exposed here, but, uh, yeah, I've, uh, worked with probably, I don't know, a hundred, 150 companies through the years in operating roles at like, you know, LinkedIn, echo sign, talk desks, a part of gong really from the, actually had the same idea for gong before gong, believe it or not. Uh, exactly. Almost the same with a guy, this guy, Ron Ohlone, who's been at gong really from, you know, he and I were involved from, from the inception. He stayed. And I think he's like, he runs. Like global ecosystem or partnerships or something, but we were at Adobe after they bought echo sign and we had the same idea for gong and we kicked it around, you know, it was really, I'll be honest. It was my idea, like, or Ron and I were thinking about we'll leave Adobe and go do this. And then we didn't do it. And then like a year later, Iran's like, I met these two Israeli guys, right. And they're doing exactly our idea. And I, we were like, and we want to get involved. Um, and so we got involved and, uh, obviously, you know, nobody could have foreseen sort of what is. Become and obviously what it will be is still, you know, to be determined, right. It's still like a private company, but that was a great experience. Um, and then, yeah, I've worked with a lot of other companies through every possible space, solving every type of problem, uh, from SAS and to AI into the AI era, including, you know, like more, more recently Higgs field AI, which is like, you know, it's just super high flyer. And it's fun to be involved with companies like that.
Speaker 2Right. Cause life's easier. Right. Significantly. I was always the kind of, I was. I was always at somewhat loser sales orgs from an attainment perspective. So when you're on Harry's and you're like, I don't know one good VP of sales, that wouldn't take something that has more of a heavy outbound motion. It's cause yeah, they don't need to, right. It's like you want the tailwind. So you said a number in that Cassidy ventures, which is like you're investing and then operating into some of these startups. What are you commonly hearing from founders in the last year? That's the biggest thing that keep from a go-to market perspective. That's a problem that they're looking for you to help solve.
Speaker 1I don't know that the problems are that different than they were five years ago, right. In a lot of ways. Right. So demand is still, you know, for as much as you go on LinkedIn and you know, we talked about LinkedIn is this magical universe of peer success is, is, you know, d demand generation is still a painful thing for a lot of people, which I think is exemplified by how much money is invested, right. And some of the technology companies that are, are AI companies that are trying to help solve those problems or hiring BDRs, right. And then, you know, training them and coaching them and all that kind of stuff. So demand is still painful, very painful. There's still a lot of startups that are still looking for PMF product market fit, true product market fit, which is like certainly having been having the experience of being a founder, the amount of respect I have for founders that start with an idea or a concept or a problem statement and they're wrong and they have to, you know, go on this like journey to product market fit. I have so much respect for those people, right. Because that is hard, right. Right. It's hard, right. And like sales can't, you can't. You can't hire sales to come in and solve a product market fit issue, obviously like hiring, um, and then into the, you know, sort of more principles around like, what is our sales operating system? What is our framework? Um, how do we manage pipeline? How do we manage deals? How do we hit the number? So all the way from demand gen issues, all the way through every step of execution, most people still have an issue with some area of that. The hardest issue of all this, we don't have
Speaker 2product market fit and we don't have demand, right? Yeah. It feels like it happens more often than not with my friends. People that we work with on the recruiting side, that they're getting hired into a demand poor environment. Why do founders let this happen? What is the thing that happens in those convos that I've never been in that they say we're going to hire sales versus work on demand before we hire AEs? I mean, usually they don't do that
Speaker 1if I'm advising them, right. But certainly, yeah, like, you know, the let's hire bodies or let's hire VP of sales or let's hire an AE ahead of demand, which I think has been stated numerous times. Yeah. On this podcast is a fallacy, right? And, and still there's plenty of CEOs that are like, even companies that are doing relatively well, or we want to grow, you know, 150 or 200% next year or whatever it is. I don't even know what the acceptable growth number is. Right. It's very much a moving, moving target. And it really is a, a demand gen issue. And I'd rather have fewer salespeople, fewer, but good and qualified salespeople sort of managing those deals, which is, that's sort of a Jason Lemkin philosophy from. You know, even 15 years ago that I think is held true, which is like, you know, however much demand you have, the one thing you have to be sure of is that you have super capable, qualified salespeople managing those deals. Otherwise you end up with, you know, X amount of demand that's finite, more salespeople diluting. And so you end up with a bunch of salespeople probably missing their number, a couple of people over maybe hitting the number or overachieving. I'd rather have two or three people than eight people diluting the amount of demand that we have, because it is, it is the opposite. oxygen. Demand is still the oxygen for growth.
Speaker 2That is, that has not changed. What do you see the best companies doing for demand gen? So it's like, okay, why did Higgsfield take off? Why did Gong take off? I'll give you an example too of a shout out to like, we worked heavily with like the Pylon team and Marty Causes just was like posting on LinkedIn a lot and it caused a lot of email. Like what are the things that you're seeing the best companies do in order to actually create demand gen? I mean, obviously the
Speaker 1companies that have like a PLG motion, right? Is like, you know, like Higgsfield has that like replit and a lot of these high flyers have it right where you have sort of a product led growth motion, which generates a lot of demand. And then obviously you can sort of sell on top of that or navigate through it to find out where you want to spend your time. So, and then obviously some founders that have, you know, big sort of platforms or voices that extend that helps. I don't think there is any one people ask, you know, how should we solve our demand gen issues? And I say everything generally, right? Yeah. Some founders create like sort of advisory boards, right? Where that are like proximal to their ICP because one of the things about sort of demand gen is expensive, right, historically, right? So like a lot of founders that when you talk about like, hey, we need to build a demand gen motion, they don't understand what the cost is going to be, right? That like one SDR is going to cost you, what, 10K a month, something like that, right? And then you have tooling and then you have to coach them up and lead them and you're probably, as a founder, don't know how to sort of coach up or manage an SDR. So it's expensive, right? And so a lot of people don't understand that. So I talked to a lot of founders like, what are like, what's low-hanging fruit or what are some like logical steps we can take to solve some early demand gen issues?
Speaker 2Not necessarily scale it, but yeah. Now your last venture, sounds like you were incubating this alongside doing Cassidy Ventures was High Five. I think the advisory board piece got me thinking too. What you're saying here is that warm intros are key with a lot of this stuff. Give like five or 10 people on this advisory board a little bit of equity and in return, they'll help you with some of those warm intros. Is that the purpose of the advisory board as well as maybe product feedback? Yeah, I think that's, I mean,
Speaker 1it's just a smart decision, right? Because, you know, most founders, like I said, right? If it's like, hey, to spin up an outbound motion, it's going to cost us like 25, 30K a month. Yeah. To get us one or two SDRs, right? Which I think, I don't think that's an unreasonable statement to make. They don't want to pay for that most of the time, right? Because I mean, there's, I've heard like D&E and others talk about like, you know, referrals can be a force multiplier early, right? As you're like establishing product market, and you're finding people that are, you know, maybe sort of friendly, slightly friendly in network, right? But obviously getting those early landmark customers are critical, right? To then, you know, sort of drive or use this like a reference for more customers. I think that's a smart decision and most founders don't do that, by the way, right? Yeah. So it's fairly low effort, low cost. It's not going to solve all your problems. I think that's one of the things with like Hi5, you're not going to solve all your problems trying to optimize for like referrals or relationship capital. Certainly a lot of companies, it's a pretty steep hill to climb. And it's just not going to solve all your problems. So you do have to do all of it. And it's going to cost money. And I think that's one thing a lot of founders don't understand how much money they're going to have to invest to really truly try to scale demand within their company.
Speaker 2So just for a little bit of background, from all your experience as a sales leader, you felt compelled to start Hi5 because you kept saying, well, when we're getting a business up and running, let's say you don't have the VCs, or on top of the VCs that you already have, warm intros are kind of getting those first 10 to 15 customers. To me, it's like, if you just put a technology around something like that, it's gold. What were the learnings from that? And maybe hard things about that business that people don't think of. There's people involved.
Speaker 1It's so like anything that has like a network element to it, right? Well, first off, the bar for like, not every intro is the same, right? So an introduction for like hiring or recruiting, right? I'm doing a VP of sales search for like, I know a great guy and you introduce him to me, right? But generally it's like a win-win, right? Scenario and even like a win-win-win scenario. Maybe it's not for you, by the way. You're introducing me. It's a win for me. It's a win for my client. But like when you talk about referrals and intros for sales, right? It's like if I want an intro to CRO at NVIDIA, right? It's a win for me, right? Totally. You make the intro, not you're using your capital. It's a big ask. But is it really a win for him, right? Yeah. To the CRO at NVIDIA? Maybe not in all cases, right? So it has to be like organic win-win. It can't be over, you know, you can't over-utilize it, right? And I think that's, I think one of the learnings out of that, right? Not everybody's comfortable doing it, right? It's another part of it, right?
Speaker 2Yeah. So I've been doing this a year. I'm interviewing and on texting basis with a lot of the CROs and VPs of sales, the AI natives. Yeah. You know, I'll send them memes and fun.
Speaker 1Guess what? Those guys were VPs and CROs for non-AI natives. Yeah, yeah, yeah, right.
Speaker 2You're right. You're right. It's like all these guys now are on this pedestal. Oh, I'm an AI native. I'm an AI native. Yeah, but 18 months ago you were not AI. Okay, got it. Now you're AI native. But they'll see this and I'll like, I started to become friends with them. You know, we'll send each other tweets and then I'll shout them out on LinkedIn and people are like, hey, can you intro me? It's such a big ask for me to burn that political capital. Where, you know, where my brain goes is like, that's not worth it for me. Like, you know, I'm like, I'm trying to be a nice guy and intro the right people.
Speaker 1Do you like an intro to a candidate kind of thing?
Speaker 2No, that I would do. That's a lot lower lift. It's like, can you intro me to see if they're a good fit for our company? I'm like, dude, yeah. If all these sales was this easy and it's like, you bring me on board, the advisory board thing would compel me, right? Imagine being like, hey, you want me to do this.
Speaker 1And it's like, it's a very delicate thing, right? Like an advisory board, you should do it. It's just smart, right? Like, cause it can help. It's not just, can I get an introduction? It's like, could I maybe get influence? Yeah. I actually think that's where relationship capital is even more effective. And it also is like less of a heavy lift, right? Yeah. Which is like, hey, like Kalen at, you know, Dropbox. Right. We're in this deal and somebody on our advisory board knows the buyer and they can be like, hey, I know you're talking to Kalen, just a heads up. He's a good guy. I really like what they're doing. Right. That kind of thing. Right. Where you can just sort of offer some reinforcement. It works, by the way. Yeah. I've like seen it many, many times, like help influence the outcome of a deal. That's actually where it's more powerful, right?
Speaker 2Yeah. That I get asked for and that I will do. If it's somebody that I do like and I interview and I'm on texting basis, that's what I mean. There's like levels of the lifts. Yeah. There's levels of lifts.
Speaker 1And the ultimate lift is, hey, I want you to introduce me as like a solicitation. To an executive buyer. I want to go sell him something. Can you please make that, burn your capital to help me? A hundred percent. Not a win for him, though, by the way. Yeah, yeah, yeah. And I think that's the issue with it. And so it can work. It just has to be sort of like organic. And I think when you're trying to like say, hey, like if you make an introduction, I'll pay you a thousand bucks. I feel like that's, you know, like it's not, people aren't necessarily super comfortable with it, right? And so like, you know, a lot of things that we thought, of course people are going to want to do that, right? But it's, I think referrals for like recruiting, there's a lot, I think there's, there are interesting things there that I don't think have necessarily been conquered.
Speaker 2You were in the recruiting space. We run a recruiting firm now. I actually think that like one thing that you seem to be a good resource on is interviewing salespeople and recruiting salespeople. You're quote on, oh, game tape is king. You've said on a couple of podcasts here.
Speaker 1There's game film as far as like analyzing coaching reps. And then you think you mean game film from like a hiring standpoint?
Speaker 2Yeah, from a hiring perspective versus a coaching perspective. What have been some learnings of interviewing salespeople that like, what's a take you used to have and then you learned from it? Like, tell us like, how should people think about hiring salespeople? I mean, I can talk about my personal philosophy around it,
Speaker 1which is, I think evolved. I mean, obviously I was, early employed LinkedIn, right? And so your, you know, your LinkedIn profile became like your resume and the resume was the truth about who you are and what you've done. Most, it's actually not necessarily, right? There's a lot of context to it. Like, you know, there's even people that have incredible resumes, right? Some of them have just been lucky, like including me, by the way. So like, I'll turn it on myself. So, you know, LinkedIn where, you know, that's obviously was like a successful thing for me in my career. A lot of people attribute to me. That was not the hardest. Yeah. Yeah. Most of the heavy lifting on LinkedIn was around like the creating the category, right? Yeah. And like defining the category and then selling to an audience that had never bought that kind of product before. But like the actual execution of it, right? You had this network, which at that point, I think LinkedIn was just a few million users, but you still had these large pockets of like recruiters using the product, right? So it was like very much like a PLG motion, right? That obviously exists today for others. And so that was an advantage for us in the sales cycle, right? Because we could lean into those, you know, I remember like in early deals, like WebEx, right? WebEx had like a 25 person recruiting team. I don't, you probably don't remember who WebEx was that they got. They were like, Yeah, they were like the old Yeah, they were like Zoom before Zoom or Google Meet or whatever, right? And they got acquired by, I think Cisco, I think they acquired it. That sounds fun, yeah. Yeah. And so, and like we had like 25 people actively using the free product, right? And so we were using that to drive, you know, sort of demand and friction up to like the VP of recruiting or the VP of technology. Or the VP of HR, that's a huge advantage, right? And so, yeah, like some people are lucky. You know, I always say like people that are in a startup, I said, if you went and asked 10 people that were there, would they say the outcome would have been different had you not been there, right? That kind of thing. I mean, that's obviously a pretty high standard to call to. Yeah, if you've ever been somebody that people said, hey, this company was a success. Had Chris not been there, I think the outcome would have been different. Right. That's, by the way, that's an impossible standard to meet, right? Yeah. LinkedIn 2011. Right, post-scale. I don't know that what they faced or what they were selling and who they were, you know, and their sales motion and all that is like necessarily a great fit for like a 50-person startup that has a limited amount of demand and maybe not everybody agrees in the problem that you're trying to solve, so.
Speaker 2Yeah. When should somebody think about doing the live role play or the scenario in the process? Yeah, because the thing about like, and I'll give you some context as to why I asked is because we've had scenarios where good and bad salespeople, you could still interview really well up in the behavioral or just grabbing a coffee. And then what happens is companies will go four or five rounds only to realize, wow, this person, when I punch them in the mouth on a mock discovery, actually isn't great. And they then move it up. But then you don't want too much friction early on. What's the sweet spot of when you should introduce this in an interview? I mean, I'd love to introduce it as the first step.
Speaker 1Just like a weed out. Yeah. No, I don't do it and nobody's necessarily comfortable doing that. Yeah, I've done the same thing. You have five rounds with someone and you, you probably have a bunch of people involved in the process, right? That shouldn't be involved, by the way. And then you get to the end and they do their, whatever their live role play or their mock demo. And you're like, oh yeah. yeah, that's not interesting at all. And then you're like, what a waste of time that was, right? But I am a believer that that is a critical part of the hiring, you know, especially today where it's a new paradigm. But like what you were five years ago isn't necessarily what you were today, right? For all of us, right? I'm not the same guy I was five years ago, neither are you. And we all evolve in different ways. And so in the AI era, it is different. Like, I want to see, you know, what's your pitch? Is it interesting? Is it compelling? And that's, to me, increasingly more important than any other factor.
Speaker 2For the pitch piece, would you recommend somebody to say, hey, pitch our product, pitch their product? Sounds like you've evolved in how you thought through that. What would you recommend there?
Speaker 1Yeah, I would say pitch their product. I mean, I see the logic either way, but if you're pitching your product or my product, I'd rather see what they do. You know, what do you do? What do you sell every day for however many years you've been at that company? Because if that's not interesting, it's probably not going to be interesting for us, right? Versus coming in and doing like an ad, talk, pitch of our product that they're not an expert on, right? I think that's a pretty high bar to clear. And you're probably missing some people in that process. But yeah, I think salespeople are pathological liars, generally speaking. And you're like, well, okay, they're probably lying about most of it, right? Are they hard workers?
Speaker 2Yeah, how do you improve that? Can we talk about the lying thing? So like, you're saying that. Would you agree? So I think that really bad salespeople probably have to lie in order. Even have a shot. But I think what ends up happening is people that are good to great to make their story better, they tell half-truths. They leave out the bad and they tell. That's lying. Okay, so, but I. So yes, yes. That I would agree with. Yeah, plausible deniabilities.
Speaker 1Yeah, which by the way, I'm.
Speaker 2You know what's an example of this, Brendan? Is like, I would say 90% of people that we work with have nuked something off their resume. Yeah. And there's going to be people out there that say that is so low integrity. But I've seen it so many times when somebody gets sold the wrong bill of goods. These are good salespeople. Oh, there's. And they don't want to have to speak through because you'll never be able to get the benefit of the doubt on that. So technically, is that lying? Yes. But I think there's like degrees of the story. Everybody's probably nuked one thing. Yeah, like, I think it's like 90% of.
Speaker 1Yeah, and like, you know, the people you look at their resume and it's like, they're like, I spent, you know, one month at attentive or something.
Speaker 2And you're like, hey, maybe just take that off. Yeah, like. See, that's what I mean, though.
Speaker 1I'm questioning, how's that helping you, right? Anyways, I worked. Before I was on LinkedIn, this was a long time ago. Most people that would see this would never have heard of them as a company called Spoke Software. And Spoke was this. Basically, it was like this product that was like just grabbing signature blocks and email, right? So if somebody had the Spoke client on their laptop, right, or their computer, and they emailed somebody, it would grab your signature block, your signature file. So it would say, this is your name, this is your company, this is your title, right? And it would pull it into this database, right, essentially. Right. And then we could like sort of aggregate this profile based off all the times that Chris has emailed somebody through the years. It would basically grab all these different companies that you would work for, right? So we would go in there sometimes and we'd see it and we'd be like, oh my God, I didn't know that, you know? That's so funny. I didn't know that this guy worked there for, you know, however many days it was, but that you noticed, you know, everybody's made a mistake and a lot of people, even some very accomplished people.
Speaker 2So that's happening now with podcast guests. I won't name names here, but like. Like I'll do the deep research props and it'll come up with two companies that we didn't even talk about around or like, did I'm like, oh, you're nuking. So it just, it's funny to see. How do you, how do you grab, how are you getting this? So I don't know how the sauce gets made on the, in the LLM deep research, you know, prompting, but for some reason it's grabbing it. It could be from an announcement from LinkedIn that like I didn't go all the way back and see and somebody didn't take that off, right? So I know people that have made
Speaker 1mistakes, nuked it, and then somehow went back and had that shit scrubbed, right? So they bought, maybe it was like Reputation. I don't know how you do it actually. Maybe like reputation.com. Yeah. So there's no proof. Yeah. Even though there was lots of, there were press releases and all that type of stuff, you can't find any of it.
Speaker 2I think like the pivot here is like, how would you advise someone to choose the right company? And does this differ from VP of sales to AE? What are the things that need to be true for it to be the good bet, a good bet directionally?
Speaker 1Yeah. I mean, that's all, it's a complicated question in this day and age because there have been like seven IPOs in the last seven years or something, right? And so like, what is a good bet today? Is that going to be a good bet tomorrow? But I don't, I think people worry too much about that. People worry too much about like, what's the moat and like that Anthropic's going to eat everyone's lunch, right? And that kind of stuff. Yes, that will happen in some cases and it is happening in some cases. In some cases, the end result is bending spoons, right? Of, of that evolution. But yeah, I mean, generally you're looking for a founder that, I would say, is somebody I could see myself working for for four years. And this is somebody that's going to let me run my show. There's a lot of founders that really don't want a VP of sales that is going to have a strong voice. Do they have product market fit? Is there, do they have demand and like real tailwinds, right? Those are sort of like the four things that you look for, I think. And it's tough, right? Because so many VPs of sales take a job thinking it's one thing, right? You've seen this, I'm assuming many times. They think it's one thing and then they come in and it's something very different, right? Mm-hmm. You really do have to audit that stuff, right? And you have to see real evidence and proof. The real tailwinds and demand and that there's product market fit. Should probably talk to some customers, maybe talk to people that worked there before, that kind of stuff. Mm-hmm. Um, I mean, if there are a bunch of people that have worked there and left, that's not necessarily a great sign, but like. If you have a more ability to get info from that, it's a negative signal. But yeah, I mean, yeah, you do, do your due diligence, I would say. I would also say, I, which I've said this for years, but like go reach out to some people that you, you respect peers or elders or whatever it is and get their take. Yeah. To help you sort of, you know, pressure test it. Because most people are too optimistic about the chances that any one company's gonna be successful because 95 out of 100 will not. Mm-hmm. 95 out of 100 AI companies out here are not gonna make it. 95 out of these 100 billboards that I drove through all the way. 95 out of 100 won't make it or won't have any type of super meaningful outcome. Yeah. And you know, like we were talking about, right? Like. The parallels to like the dot-com bubble, which was. Before my time. So you, you might educate me on this. Yeah. The beginning of my career, the dot-com bubble. Yeah. You know, it was a total wipe out basically of tech in Silicon Valley, right? Where like everything, almost everything died. Everyone left. I've seen this before. The commute from like Mountain View to San Francisco is like an hour and a half. It became 40 minutes. Right. Within three months. Right. That's so funny. To the point where it was like uncomfortable. So we see this boom and this bust sort of cycle here and it stays consistent. In this AI era, the high flyers. Are flying higher than anyone ever has. And I think you're gonna have some bigger outcomes than anybody ever has probably. Like the anthropics, the open AI is even, I know it. People act like I use open AI and I feel like I'm saying I use a well dial up these days.
Speaker 2Right. But it's great company. Right. Yeah. Who knows? Astra has made a big push.
Speaker 1It does, it does fluctuate back and forth. But I'm uncomfortable sharing that. People are like, oh, like you're not in cloud and doing cloud skills.
Speaker 2Well, as long as you're not using, well, they make fun of it more so for like, if you're using Gemini or something, but yeah, yeah. Yeah. There's all these tweets of like. Yeah. Yeah. Yeah. I think the high flyers will have massive outcomes, but that'll be a small number of companies. Right. I think generally. I think though, though, this is something we were chatting about. It used to be a lot more boom or bust. And if you take it over a long time horizon from start to what the actual exit window is, it's still boom or bust, but thank God for the secondary markets, right. Or companies like clay that are saying we want employees to take a little bit or get a little bit as they go up, uh, with the rise with us. I guess like. By the way, shout out Todd Bustler.
Speaker 1Yeah. Yeah. He's fantastic. He runs enterprise sales for clay. Yeah. And I think he's a great guy.
Speaker 2So Todd was our first guest. Oh, he was. Yeah. Yeah. On the crew podcast. I didn't know that. So Todd and, uh, I went to dinner with Todd two weeks ago. Uh, he was on, we, we did a round table episode with Todd at clay, Mark Eber, profound Liam Mulkey at parallel and then Jack Gash at Aboka. I know most of those. So Todd's coming on as a second guest. Yeah. Um, so he's a buddy of mine. Yeah. I'm a, I'm a fan of Todd. Yeah. So yeah. A good example of that. Like traditionally you would have to wait and wait and wait, but now you're getting tender offers. So you're able to get a little bit and you can also sell some of yours on the secondary market. Yeah. You think that's a good thing for employees or what's the downside risk of that now being in the market? As somebody that's sold secondaries before, right.
Speaker 1I'll, I'll sound like a total hypocrite. Right. But like, I think it's become a really bad thing by the way. Right. Because all the companies that should be public now, honestly, Stripe, Databricks, a lot of those guys probably should be publicly held. Right. Especially holding out longer.
Speaker 2All right. Y'all quick break. If you're getting value from this, do me a favor and hit the follow button on YouTube, Spotify and Apple. It helps way more than you think. Now back to the episode. Is this advice you would give this somebody like, have you seen friends, whether they were like, oh, I'm just going to wait for the final exit in a.com and you've just seen, and he's like, no, take, will you always advise just take chips off the table when it's in this rise period, if there are chips to take off the table, I feel like there's a ton of chips right now in the seed through D, which is like where we play and my friends, my friends are at and we're recruiting for, there seems to be a ton of buyers at the end of that. Rainbow. Yeah. Right. At least right now, but.
Speaker 1With a pot and a leprechaun and all that. Yeah. Um, yeah, you should take some, you should not let it ride all the way generally to each their own. Right. But like, there's not that many companies that have a hundred percent confidence are truly standalone, you know, iconic companies that are going to be able to cut through all the headwinds of what's out there and what's coming.
Speaker 2Yeah. you think nowadays if it's like okay we have lab risk, the anthropic is just going to do what we do. What companies do you think pose that risk and then ones that are safer from that? I'm going to, I'm going to turn that back on you. What companies do you think? Yeah. So I mean the
Speaker 1foundation players, obviously. Yeah. I am very, very structure for foundation. Yes. And now I'll turn it to you.
Speaker 2Yeah, of course. I would say I'm a former consultant and I have friends that are in finance and my wife's a lawyer. So anything professional services I actually think is safe from the labs. A lot of people are saying, give me an example of a company that's like AI
Speaker 1professional services kind of play, right?
Speaker 2Yeah. So Harvey and Legora for law, you have Rogo for investment banking, you have basis for accounting those. And I don't know if anyone's junior with their London base, they're doing it for consulting, but no one's really cracked that right now. All of those, I think are going to continue to rip. And I don't think that they have lab risk because all of those partners and all those people at those firms are going to ask, I only want to buy from the people who have solved the hundred questions in the last mile versus. We use Claude for our legal needs. And then we use a lawyer at the very end of the process just to like, we get a lot further with it. So like there's risk in the SMB market, but in the real big professional. So I'm very bullish on those because I think eventually once they crack the technology, meaning the, the TAM for legal software is limited. It'll be the eating the work. I think eventually the Harvey's and Legora's require companies like Crosby, like an AI native legal firm, and then they'll start to be services and they'll be, you know, they'll be, you know, they'll be the software. So I'm very bullish on those. Um, the infrastructure layer, of course, I don't know enough about like, okay, why inference and all that. I just can regurgitate what I hear on other podcasts, but yeah, that's like what I think is AI for professional services. I think for a lot of those reasons, it's like, I'm very bullish on.
Speaker 1Yeah. I don't worry about it that much, to be honest, right? Like it's certainly certain spaces are in proximity to things where, you know, you're, you're either going to eat or be eaten right. Kind of scenario, right? Like the go-to market space, right? Which is, which is tough. It's like get to the big boys, you know, the big kids table or die. Right. But is there really, is a real appetite for point solutions who gets to be at the big boys table in that particular space or big boys and girls table? Sorry, but like Gong might be there where they want to just own the entire stack. Yeah. Right. From conversational intelligence to contract execution. Right. I think that's where it'll go.
Speaker 2Yeah. Yeah. On that note, what are the tools you, you brought something up when we were talking earlier of like ideas that need to exist, but don't yet in the go-to markets. Are we missing any tools like that? You were obviously early with almost building Gong and then they built Gong, but then you were like early investor and advisor. Yeah. Sounds like you're like, no, where the puck's heading with a lot of this stuff.
Speaker 1There's things that I never would have thought were possible three years ago. Right. Or whatever it is. Right. So like CPQ and contracting, right. That kind of stuff was just like a graveyard of, I called it graveyard of non-empires. Right. In like 30 years out of date. Right. But like in this sort of AI era and like, usage and consumption based pricing has, you know, sort of broken the contract, like the pricing and contracting and you could call it CPQ, you could call it whatever else. Right. But it's creating issues for a lot of these guys. Right. So as more and more companies move to like usage and consumption based pricing, the variables of what can happen right in the contracting and negotiation process, none of the products that have been built to date are built to support that. And so I've seen that as like a pretty common theme. Somebody said CPQ is hot the other day. I've never heard that. Yeah. It's like the least sexy. Have you heard that? No, it's like, and I used to sell it at Salesforce.
Speaker 2There's our, we, I sold a couple of CPQ deals. And everyone knows how bad that product is, by the way. Yeah. Well, that, just the implementation was, nobody was ever pumped to bring that in.
Speaker 1But now you can implement stuff a lot faster. Right. Where AI, you know, like a lot of like the contracting and negotiation and fallbacks, AI can, you don't even need to go to deal desk kind of thing. Right. Which is a bane in the existence for a lot of sales teams. Right. And so there's stuff there. I think that's interesting. Like, I never thought like, And by the way, this is, I'm not saying this is like the most innovative space ever, but like the AI BDR space. Right. Like I'm seeing like real, like upmarket enterprise traction. Right. For companies that have, you know, and I think.
Speaker 2Yeah. What needs to be true for that? Because we keep hearing this, that in this SMB market, like Jason Lemkin talks about this all the time with his business. He says we have an AI BDR, but it takes his existing CRM data for his sponsorships for SASTR. I understand how that use case can like be automated. You go upmarket to general AI native and SASTR companies. No one's using it. So one of the things about AI is like,
Speaker 1it's better when there's a brand, there's brand, there's tailwinds, there's demand, there's right. There's some sort of successful operating system that where AI can really, you know, sort of just cover automate and cover a lot of surface area. Right. I think a pretty true statement about AI, right. AI will help you do all these things much faster, much more automated that people had to do before. Right. I just care about you. about what you what you can do in the field and i don't think we have a great way to do that now and so i feel like there's an opportunity with ai i might do it at some point or somebody that's listening to this might do it if you do do it i would implore you to come to me to get me involved because because i gave you the idea but like that's what i want because i don't care what your LinkedIn profile says in a lot of ways and a lot of us have aged out networks in some right in some cases where like everybody that we knew went on to do whatever right but you have to keep building your network right which i do but like yeah we're just increasingly like hey who do you think is good is less uh relevant to me um and what i care about is just like how you played on the field yeah what do you put out there on the field and i think it could become a standard where everybody has to cross that bar even like vps of sales right we're like hey you have to show that you can still pitch and sell at a high level and then that game film that should be your resume right from a sales standpoint and LinkedIn you know so like to me that's a better recruiting sales that's a better product than LinkedIn anything
Speaker 2that LinkedIn can sell reminds me the scene from Moneyball when uh when they're like we're not gonna bring this guy on he doesn't have a good looking old girlfriend he's got no confidence yeah they're making assumptions on things they're just vibe based yeah and then Brad Pitt comes in and he's like but they get on base and that's kind of what you're like you're saying is like how are they as a baseball player how are they as a seller and like that's really when now one thing about your idea and i i'll put this on the screen um the post i made about four months ago i was tagging my friends at juicebox and metaview and a lot of these recruiting tech platforms i would love that as an interviewer back in the day and the reason why i say this is because i was notorious for wanting to get this dream job and then going to the last round and not getting it and a lot of times i knew that it probably was something i could have done better in my game tape that nobody was telling me because no one gives you feedback when you don't get a job yeah that is a brilliant idea i know it's a little bit different than what you said but there's that's probably a bigger tam you can sell it not only to the companies but you can also sell it to the candidates because candidates are very hungry for that sort of feedback are they going to pay for it definitely i think i think that i'm not 100 sure they would pay for it right i think if the online if it was
Speaker 1free i think they'd they'd
Speaker 2probably take why don't you think that people would pay for it like think about somebody who keeps getting the final round and getting dinged and then not getting any feedback as to why i think that those people smart enough to get into the interview process smarter to get far they might have the eq to be like Who's providing the feedback to them? Well, that's what, in part of your example here, I think you've got a couple of the VPs of sales, CROs who have hired before to make the, that's part of the product team. It's like, hey, these are the best practices on interviewing. Yeah. So that's part of it. That's interesting. I think, I mean, I would love it. I like mine more, but just kidding. Yeah, well, I'm saying as a spin-off, it's product number two for you guys. Yeah, yeah, yeah. Well, there's no you guys. Yeah, yeah, yeah. It's just, yeah. You're incubating. Ideas are free, obviously. I'm actually very curious of this. This question we ask a lot of guests on the pod is, what are the sales mafias that you respect, that you didn't work, you've never worked out before? That in the SaaS era and then now in the AI era, that you're like, these teams were elite and like the reasons why you respect them.
Speaker 1You know, Sam Vaughn, who worked for me at Echosign, right? He was the VP of sales for Zenefits, right? A lot of people from Zenefits have gone on to do really great things. I think Sam did an incredible job of hiring and recruiting there. Obviously, exercise. One of the things he learned. But like, yeah, like that. There's a lot of people that have gone to do great things. Zenefits was not a great outcome for reasons I won't get into here. But yeah, go read Parker Conrad, who some of his feuds are with about that, you know, to get a good feel for that. But yeah, a lot of great people off that Zenefits tree. A lot of great people off like AppDynamics, I think would be one. AppDynamics slash Zscaler slash, right? A lot of these guys, you know, like Mike Ernest. I wouldn't be surprised if OpenAI is trying to get him. Right, because of the. They're all going there.
Speaker 2All these guys, all the. But Mike's great.
Speaker 1Paul is great. Who's it? I think that's what, Chaingard, right?
Speaker 2Who's X off of that tree. Ben Horowitz and Brian Halligan were on a pod. And Ben Horowitz was telling him, saying, the reason why PTC was great, sales team, is because the product actually wasn't that great. I'm curious what made. Why do you say AppD and Zscaler and Zenefits? What about them is the reason why you respect the sales team there?
Speaker 1I'd probably be less qualified to say. I'd say why from like AppDynamics and those guys as much. That'd be a better question for those guys. Yeah. Like, I just, I know a lot of those guys. They're good guys and a lot of them are going to do great things. Like Zenefits, yeah, I mean, like Zenefits had a sales operating system that I believe in, right? Because obviously I was somewhat involved in sort of building that. And I think that's reflected at like, you know, Sam took that to Brex. I think that's reflected at Rippling and other places where, you know, there's just no room for bullshit in the sales motion. There's nowhere for deals to hide. And I think when you create a culture like that is manifests itself in the entire sales motion, right? And the entire sales operating philosophy all the way from like, you know, first discovery call, right? Yeah. And that is uncommon in my experience with most startups don't do those things particularly well. Yeah. So those would be three. Let me think of other.
Speaker 2Any AI native ones? I know you love that I delineate the SaaS versus AI.
Speaker 1I mean, Decagon, I'm a big believer. Yeah. Evan Cassidy, his friend. Had him on the pod, yeah. You know, he's my brother. Wait. He says, people think, people ask him if he's my cousin. He gets asked that. You actually got me there for a second. It made me think. Yeah, yeah, yeah. I really like Evan Cassidy at Decagon. Yeah. A lot of young sales leaders, Nick Sully at AirOps. Yeah. I'm a big believer. Walker Fitch, who's an artisan, I think, I'd be impressed with. Like a lot of these young guys, I think, up-and-coming guys, I think, are great. And obviously, there's a huge, you know, the gap in experience and age between, you know, the Mike Ernest and those guys and the younger guys, but it's great to see all this young talent up-and-coming in tech. I was going to say the Valley, but a lot of them don't actually live in the Valley, right?
Speaker 2What is the. You were enlightening me earlier of. Yeah, when I come down here, I just come to where we're at now. Downtown SF, Union Square SF, Financial District. Yeah. Um, you said that's a lot different than, like, Bay Area generally. I just think it's all AI startups around here, but I was very wrong about that, apparently. Uh, it's all.
Speaker 1Well, around. Define around here. I guess the whole Bay Area, I just thought it was a bunch of tech. Yeah, I think that's the, like, early-stage tech people. I think it's an interesting, you know, talking about people think the Silicon Valley and the Bay Area is just all startup people, right? Just taking. Making bets and taking chances. Yeah. And you get outside San Francisco, whether it's, you know, north, south, or east, west, you're in the ocean, so. Mm-hmm. But, like, it's mostly people that work in big technology companies, like Apple and Adobe and Microsoft and NVIDIA and all these guys. Salesforce. They're not working in startups, right? Uh, San Francisco's, it's very much kind of a bubble in that regard. So I live in Los Gatos, which is maybe 20 miles south of Palo Alto, and I'm an alien, right? Mm-hmm. I'm in the startup world, and everybody around me, all my neighbors, nobody's in the startup world, generally speaking. And so when I talk about who I, you know, sort of my history and background, they're like, oh, that's f***ing crazy, right? Like, you know, they can't even fathom it, you know, like a life spent working with those kinds of companies because it's, you know, it's risky. And so, like, a lot of these suburban bedroom towns and cities around the Bay Area, you have people that are married with kids and families, and they're not looking to necessarily make a huge bet on going to that 20-person seed-funded startup in San Francisco, right? They're looking for stability. So that's what most people in the Bay Area are doing, right? They're working on that. They're working in bigger tech companies with more stability. That's what the majority of people are doing. And I can tell you, the difference is so, like, dramatic, right? Like, I remember when Adobe bought Ecosign and we went there, like, who are all these people? In the first all-company meeting we were at Adobe, it was like 10,000 people in, like, San Jose Civic Center, I think it was. The meeting started with, like, a celebration of everyone that had just reached 30 years of tenure there, right? Oh, my God. And we were like, what? Like, why on earth would we do that? Why would you want to spend 30 years at one company, right? But, like, that's how these big companies operate, right? Tenure and political standing, you know, are more important than who's got the best idea right now, which is what I love about startups, right, is that it is a true, you know, it should be just a radical meritocracy. There's no room for politics or bureaucracy and whoever's got the best idea today and whoever performs the best today or this quarter or whatever period you're looking at are the people that should get prioritized for more opportunity. Yeah. Which is, you know, I think, if you look at the people that have worked for me and gone on, you know, to be VPs of sales and CROs, it was that operating philosophy in mind, right? Which is, it's hard. Startups are hard. So the people that actually find their way to be successful in it, I want to extend that DNA to as many people as possible. Yeah. Right? And a lot of people say, okay, like, let's go hire in somebody outside, right? I don't believe in that. And, like, a lot of people disagree with that, right? A lot of people feel like, no, no, no, you should not promote from within. That shouldn't be your strategy for hiring and growth and unflattening your sales organization. But for me, it's, you know, and not everybody, you know, wants to do that. Not everybody wants to move up and manage or lead a group or a team. But, like, those that do, I can't, I'm the first one in the pool with them to do it. I love that. And that's, like, that's what Sam Bond was and Matt Plank was and Jameson Young and all these guys that, you know, you're talking about, $50, $60 billion in market cap or whatever between those companies. Maybe not that much, but they were promoted because they were they proved yeah that they could excel i'm like why would i not want to extend their ethos and what makes them successful and obviously they the fact that they are exemplifying our values the things we care about right so like if you just have a rogue agent you know somebody that's killing it internally but they do it their own way and they you know they don't want to share their secrets or whatever it is that's not somebody that you're probably going to promote right yeah and there are people like that and that's fine and like i usually my take on them is like just let them let them keep eating you know because and a lot of people will be like oh i don't anyone that doesn't fit our culture i want them out i don't care how how well they perform my take is like just put them in a box right and just say like keep feeding them let them keep closing deals and having success but we're not going to build the company around them right but you don't you can have a lone wolf and
Speaker 2still be yeah i'm fine
Speaker 1with that right yeah yeah
Speaker 2companies are looking different nowadays what's one company that maybe in the past you wouldn't have worked with from a advising side that has surprised you and it's been like a good success story for you guys at cassidy ventures yeah there's one company
Speaker 1uh we've worked with called athena security which is like a company that's like i guess broadly speaking in sort of like the threat or weapons detection space it's like software hardware ai right for health care organizations education organizations school you know school districts counties to basically find threats that might be coming into their environment and like you know when i was first approached by him i was like i don't know anything about the space i'm not sure i can help right kind of thing which i've done before right i'll tell people i'm like i'm really not sure i can help you but if you want to pay me go ahead right kind of thing um that is like so these guys were like you know they had the best quarter q2 best quarter this company by like double and then they'll like be on par maybe a little bit above that this quarter but like 10 almost 10 million crossing over 10 million in error bootstrapped they've taken no institutional money huge tam and big deals right they're doing like multi-year four-year half a million four-year million dollar deals right with like pretty clear product market fit and minimal headwinds and so like i always find that like today it's like what what are the companies that you if i was a vcu would i put money into that's a company i'd probably put a check into is it because you think security concerns are just completely well it's a it's a motor right it's like it's you know there's literally like hardware right there's like physical things right it's not just vaporware in the cloud kind of thing right or ai reasoning or whatever else so yeah so like they have a moat and their customers commit usually for like four years right so there's like i'm sure there's some risks in that model but like that's pretty good when a customer is going to you know commit for four years and give you a million dollar check up front for it yeah and so you know creates like i think consistency like less risk volatility and churn and it's just huge the market for it it's just absolutely huge and there's a lot of these states are starting to put legal standards in place right that like certain thresholds and minimum level like threat and weapons detection has to be in place in like every hospital like california yeah by like next year and so yeah i don't know what the standards are right and like a lot of companies i think that are pretty good or doing pretty well that are having a hard time getting funded now because i think these a lot of these vcs are they're just looking to get their money into anthropic right and that's like a small number of companies right yeah generally so yeah yeah yeah it's been that's that's definitely been a surprise but yeah it's been a fun career so far
Speaker 2awesome last question actually i just thought of so who mike ernest matt plank these guys on my list who else are like two or three people that we may have not had you you mentioned evan he's been on you mentioned todd he's been on who are some people that you would say would be a good good for the crew pod i would get
Speaker 1there's a guy who runs international sales rippling but he also was the vp of sales at gong for like six years named jamison young okay who's a friend who was also off that sort of echo sign team and then zenefits i talked to him i think he's
Speaker 2great if people want to connect with you is it like hey startups that are looking for sales help is it um like who would be best to reach out to you that would be relevant for your time uh yeah
Speaker 1i think um you can reach out to me on linkedin i don't like doing a sort of marketing pitch for myself but yeah like you know how to yeah some of you have probably seen me you know whether we're connected on linkedin but yeah feel free to reach out brand thanks so much
Speaker 2man yeah excited for this thanks for having me on of course yeah yeah likewise thanks for hanging with us if you like this one follow the show on spotify apple podcast and youtube and we'll see you next week cheers
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