Episode Transcript
[00:00:06] Speaker A: Hello.
[00:00:06] Speaker B: Welcome back to Rogue startups. I'm your host, Craig Hewitt. Today we're talking about sales. Everyone's favorite thing to talk about, if it's not already by the end of this episode, is going to be serious. It's awesome. I'm chatting with Peter on, and Peter and I have known each other for a while. Sales guy at heart, really technical, works with technical founders all the time to help them improve their sales game.
And in this episode, it's really a bridge for me to talk about LinkedIn. We talk about LinkedIn. This is the last episode of our LinkedIn series and we talk a lot about it. And Peter dropped some amazing knowledge towards the end of the episode. So please stick around to the end because the end of the episode is really where the meat is. But to understand the lens through which you're seeing that, you gotta understand where Peter comes from in his experience at some of the finest kind of organizations in the world. Right. Dropbox Slack. Right. These big companies that are amazing at selling to the enterprise. And so I think as the only person in this series who really speaks to selling to enterprise with LinkedIn, Peter is very uniquely qualified. And so I hope you enjoy this conversation with Peter. Please stick around to the end. He dropped some amazing knowledge about specifically how you can bridge the gap from just creating content and kind of fussing around with LinkedIn to driving actual leads and engaging with them, moving them on to the next step in the sales process. He does it really, really, like, genuinely and authentically. And I'm about to go steal it, so I hope you do too.
I want to start by asking what might be like a really obvious question, but, like, why do you think so many technical founders are scared of sales?
[00:01:56] Speaker A: Great question. I think it comes down to the fact that they just haven't done it before. I think sales, you need a lot of repetition. It's a confidence game. I think to have the right mentality is the most important thing in sales. And I think technical founders, typically when they're starting companies, they pour a lot of resources and time into reading literature on the web, but they haven't actually executed on the sale.
So I think that's part of the reason why folks are very timid and it's really hard. The other thing too is kind of what I just mentioned. There's so much out there on sales that is misleading and there's a lot of stereotypes.
[00:02:38] Speaker B: Outdated, you can say that.
[00:02:39] Speaker A: Exactly. Outdated. A lot of stereotypes about sales itself and the sales people themselves. That's a lot about like boiler room type situations or, you know, specific folks. You know, like, how do I say this in a very PC way?
[00:02:54] Speaker B: It's been very Wall street kind of guy.
[00:02:57] Speaker A: Yeah, exactly. Exactly. Wall street type image is seared into people's brainstor. And I think a lot of technical founders haven't grown up in that environment and don't want to become that stereotype. So I think there's a lot of nerves around. How do you actually absorb the profession without changing your personality or your values?
[00:03:17] Speaker B: Cool, cool. So I don't know if I'll have given this background in the intro, but you and I know each other because you were a client of mine and you did a podcast about just called decoding sales. I still remember because the title is so amazing. It's like, perfectly describes the people that you're talking to. But you help typically, like, technical founders of startups do better in sales.
[00:03:39] Speaker A: Right, exactly. Yup. So whether, you know, there are usually a lot of engineering backgrounds, product backgrounds, sometimes even folks who are in operations or partnerships, but haven't done the sales role specifically.
[00:03:51] Speaker B: Yeah, yeah. Cool, cool. I mean, that's kind of my jam and my background. I help some folks do better in sales and go to market, too. And what I find, and I'd love to hear your experience with this, is that at some point there's this switch that flips and something happens and they're like, holy shit. This sales stuff is, like, legit, and it really is a great way to grow a business, as opposed to, like, the other camp, which I think is like, build an amazing product and viral loops and blah, blah, blah, blah, blah, blah, which, like, I'll say as a form of procrastination, which is the very kind way to put it, actually.
[00:04:32] Speaker A: Yeah. You're avoiding the inevitable, which is you have to product, right? Yeah.
[00:04:37] Speaker B: Or the optimal, maybe, like, you're avoiding. You're avoiding the inevitable or optimal because it's uncomfortable, like you said at the very beginning. Yeah. What do you think is that switch triggers that switch to flip in people to see kind of the light, as it were.
[00:04:52] Speaker A: That's such a great question.
I think it comes when you.
Okay, let me answer this in this way, because you mentioned we met through castos, and I almost forgot that, but I remember that experience as being very authentic because I didn't feel like I was being sold. And in fact, I reached out to you because I felt like you were a thought leader in what you did. I actually wasn't sure if I was gonna buy anything from you, but I was looking to pump you for information, so I don't know if you remember the conversation. This is probably like, wow. Like, probably like three, four, five, maybe like four years ago even. I don't know.
[00:05:33] Speaker B: Yeah.
[00:05:34] Speaker A: But I was even asking you, like, hey, what do you think about the concept of the show? It wasn't even like, how do I grow the show? It was more like I was so green in podcasting itself, I was just wanting to learn from somebody who knew their craft. And so, to answer your question, I think the power comes when you realize you have knowledge that folks don't consider to be when you have knowledge that folks consider to be novel, but you consider to be unconscious. I think that's when the power and sales starts coming into play.
And it's how I started my coaching business, too. I had a ton of organic coffee chats or chats over beer. And I think the power came when I realized, okay, my advice actually is unique. It's unique to the folks that I'm selling to or potentially could sell to. It might not be unique to me, it might seem so basic to me, but me just talking over a beer is giving folks a lot of business impact. And so I started to realize the power of that when my clientele started telling me what my advice was actually impacting so organically. They'd be like, hey, you know that coffee chat we had in San Francisco, that actually helped me close my first six figure deal. And then you start to realize, okay, maybe I'm undercharging because I should get more than a free latte.
[00:06:53] Speaker B: Yeah, you know, I love vodka sodas.
[00:06:57] Speaker A: But, like, you know, even getting three free vodka sodas doesn't seem enough if people are telling me, wow, I'm actually now confident in closing six figure deals. And so I think that's where the switch was. It was kind of, I think over a period of time, it wasn't like this one. Aha. Momentous. It was a series of clients telling me, this is what you actually helped me do. And I say I talk about the metrics around deals, but oftentimes it's also just about mentality. People just tell me, you actually make me feel better about myself on a sales call. Emotionally, you actually have taught me how to communicate and have high eq, and I think that's really where the power came. So I guess I'm going to turn the question on YouTube, because I don't know if you felt that interaction we methemenae was authentic as it actually came across as, or if you were like constantly thinking while I was asking you a question. Okay. Like, I gotta actually sell this guy because he's. He's asking me for a lot of things that, you know, if we just end this call and he doesn't sign up to cast those, then I'll be regretful, you know, like, I'm curious, like what your mindset was on that call. And I know you have thousands of these, so it might be hard to remember me specifically, but. Yeah.
[00:08:06] Speaker B: So I don't remember our call specifically. Good.
[00:08:09] Speaker A: I'm glad you're honest. But you remember podcast name, which is. I'll take that.
[00:08:14] Speaker B: Yeah, yeah.
But I'll just share how I approach selling our castos production services because I think it's probably a lot like how a lot of people, just in general, our audience and yours approach selling is we have a widget. Sorry, you have a hacky sack that's like my fidget spinner. So we have a widget that's this hacky sack. Right?
And it's the same hacky sack as you sell. And as Bob and Susie done, the street sell, like, largely the shit that we all do is the same.
And you can say, oh, well, I have a widget that's shinier, better, or faster, or whatever. That's fine. But the reality is nobody's buying that shiny button or that slightly faster web page. They're buying. Like, I got to decide on a vendor for this thing or I'm going to get fired.
Right? And my CEO said, we got to start a podcast and it's got to be good.
I'm going to go with the person who gives me the best chance of not getting my ass in the wringer over this stuff. And so the way I approach sales is just me. Like, I'm selling me way more than anything else, especially for a professional service, because that's all that matters, right? Is that they like me and they trust me. And I say, hey, if you like and trust me, you believe that what I said is true about us creating a good podcast for you.
[00:09:40] Speaker A: Yeah. Yeah.
[00:09:41] Speaker B: That's my sales strategy. And I think you can translate that into your CRM or your new AI tool or whatever, especially as it gets to, like, fundraising or whatever. Because, like, in those instances, like, you got your metrics. Sure. And we've done this and our tam is that and blah, blah, blah, blah. But like, yeah, every single investor out there is betting on you, not your business.
[00:10:05] Speaker A: Totally.
[00:10:06] Speaker B: Especially early on.
[00:10:07] Speaker A: Yeah, yeah, yeah. I think the other component of that too is I talked about in the beginning of the show, a little bit about confidence and mentality training. I think it's also, how does the other person, the seller, make you feel as a buyer in today's modern day and age? And I think that's something you did really well. You made me feel like I could do this podcast and that it could become big. You gave me that confidence. Yeah, I already talked to you, and it felt like podcasting was just, like, this insurmountable mountain because there's so many podcasters out there that I probably never would have gotten started. Right. Yeah, I think that's what I do as a sales coach, too. It's like, hey, you can actually do this. I don't care if you've never sold a six figure deal.
I think you have superpowers that you don't know about as a founder. And you have a very unique story, being a technical founder, where a lot of buyers will give you their money just because you have a unique brain and perspective, and it's now incorporated into this game changing, generational product. And then, you know, like, what happens there is. People are like, wow, I've talked to so many go to market coaches who make me feel like the other. But here's Peter, who makes me feel like I can actually do this with him and eventually without him. Right. So.
[00:11:23] Speaker B: Yeah, yeah, no, yeah, totally. So I saw a thing the other day.
Someone saying, like, the biggest leverage you can have in your business is just showing up tomorrow. Right. Like, and I think that's a big part of it. It's like, it's fucking hard. Like, all this stuff's really hard. And if you can have the mentality in the internal and external environment to just show up and get, like, a little bit better every day, yeah, you're gonna crush it. Like, and that's so much. And that's sales, and that's being a founder, and that's fucking LinkedIn and YouTube and. And team and all that kind of stuff. Like, it's so. It's so that longevity is so underrated, I think.
[00:12:00] Speaker A: Yeah, there's no overnight success story, right?
[00:12:03] Speaker B: Yeah.
[00:12:04] Speaker A: Yeah, agree.
[00:12:06] Speaker B: Cool. Okay, so I want to. I want to have a little therapy session about. About coaching because.
Yeah, so currently, cas dose is, like, you know, 75% of my time. About 2020, 5% of my time is spent either. I'm an advisor to tiny seed, the accelerator program that we were part of. So, like, I help a whole bunch of. There's, like, 200 companies in there, so I help a whole bunch of them, and I have a handful of clients on the side that I coach one on one.
You have a much larger but similar kind of program and coaching setup where you help founders get better at sales, right?
[00:12:40] Speaker A: Yeah.
[00:12:41] Speaker B: How did you come to, aside from you were helping your friends and they bought you coffees and stuff, how did you come to say, like, I'm going all in, this is a big deal. Like, this is my whole bit for now. Like, what did that evolution look like?
[00:13:00] Speaker A: Yeah, I think evolution is the right term because I first went into coaching, like in 2016, actually. So this was about eight years ago.
And back then I knew my passion was an early stage, but I had never taken a company from zero to something. My background is, I was at Google when there were 40,000 employees. I sold a television commercial product that was an experimental startup within a large company, but it was still with the resources of Google Dropbox. There was about 90 people when I joined, and they didn't have an enterprise product, but they still had over 50 million users. Right. And millions of dollars of revenue coming from their consumer brand. So enterprise was still an experiment that had some tailwinds and slack. Similar story, right? There were 300 people when I joined and I closed their first enterprise deals, but they still had this product led growth motion where they did have a good, healthy base that I could work off of. So just to kind of get to the point of your question, like, in 2016, I still had a lot of these large brands, but I couldn't go to a founder and say, I know what you're doing. You know, like kind of like weekend. You have that credibility because you've actually been a founder going from zero. So the flip for me was I joined Twin Gate, which was a cybersecurity company that had no customers when I first started advising them. And I decided, let me actually fully dive in to see if I can build the sales. Customer success and partnerships function not as a CEO, but at least as the person who's responsible for $0 in revenue and trying to get to millions. And because I had success in doing that, I was like, okay, now I can actually go to a founder and say, I know how you feel. I've been in not your shoes, but I've been in the shoes of where your company is right now.
[00:14:49] Speaker B: Yep.
[00:14:49] Speaker A: And that gave me a ton of confidence to say, let's make a business out of this because I already know I have the organic interest in terms of advice. Now I have, like, the hard experience of being able to build from scratch and the marriage of the two, I think, really allowed me to say, okay, I could do this for the long term without feeling any sort of imposter syndrome. Gaps on my side, man.
[00:15:11] Speaker B: That last part is. The last part is everything, right? Like, yeah, I have so much imposter syndrome. I have so within castos and on the coaching side, and I shouldn't either way. I mean, cas dose were a yemenite, you know, kind of millions of dollars a year in revenue. I've been doing this for almost ten years now. I've kind of done and seen it all. And every single time I go into a coaching call, I'm like, man, I could screw this up. I don't know what to say.
[00:15:41] Speaker A: Yeah, totally.
[00:15:42] Speaker B: I'm a fraud. I'm a failure.
[00:15:43] Speaker A: It makes you good, right? I feel the same way. I get nervous before coaching calls too, because I want to maintain the reputation. People came to me with a, and with AI, right? Like, Dropbox feels like such a, like ancient company now, unfortunately, because it was founded in like 2007, right. And so I think for coaches, it's really important to stay on top of the modern trends as well and to, you know, make sure you convey, hey, like, it's not one size fits all. My data points are stories from the past, and my superpower is not telling you exactly what to do, but it's to think through how you might approach situations and give you the confidence that you can use my stories to accelerate learning. But I'm never going to give you like, the full answer every single day. Right?
[00:16:34] Speaker B: Yeah, yeah, yeah. I think the recency of your experience is really important.
It's something I say a lot is like, hey, yeah, I'm a founder and so I literally have been in your shoes.
And I know, like, I've been. I can help you, you know, and whether you're a founder, you're, you know, employee number one or whatever, like, it's kind of all the same. But I also did it in the last few years, not fucking 25 years ago. Like, some of these, I would say gray hairs, but I got, I got, I got a fair bit. But I do think that's important. And that's actually one of, it's one of the things I'm most apprehensive of.
There'll be a time when this is what I do is coaching, and when I lose that context of, I'm in my CRM every day and I'm in marketing automation software for my real business.
At what point will someone say something to me and I go, what? I've never heard of that thing or, or whatever. I don't know. Does that, does that concern you that that time will come? Or are there things that you do where you're like, yo, I'm good. I got this covered?
[00:17:51] Speaker A: No, that concerns me every day, actually, you know, because I never want to be the dinosaur in the room, right. And it is also like how I sell myself to, if you notice my LinkedIn banner, I clearly lay out like new school sales thoughts, right? But then if I'm in the industry for 2030 years, I'm not new school anymore, right? So it is something that creeps into my mind, like am I gonna have to change my marketing message and then start to say I'm like, you know, the old school guy who still can make things work? I don't know. But to answer your question, like, how do I, how do I address it? Right? Because it's not just something I'm anxious about. I do intentionally work through specific scenarios with my customers. So I'll give you an example. I love getting super tactical with customers.
I make sure that's part of my sales coaching. I never like to give frameworks and have the CEO's go off on their own and execute it on their own. We actually have sessions where we're looking at an email for 15 minutes and dissecting it and going through the back and forth of the email and then as much as possible in real time. If I help a CEO craft an authentic email, I want to know what the response is and I want to be able to react to that response together with them. So I think that's a good way to kind of be like a copilot to your clients and make them feel the power of not only your strategy, but the tactical, tangible nature of how your strategy turns into results.
So that's like a very specific example. I do that with tools as well. If I hear about a new CRM, I hear a lot of people talk about Adio ATT IO. You know, I grew up on like Salesforce and maybe some HubSpot and, you know, airtable a little bit, you know, if you're like very, very early stage but never used audio or heard of it. And so my response to that isn't like, you should use Salesforce because that's what I know. It's, let's actually unpack that together and I might even sign up for a trial and explore it myself because I'm curious. So I think that helps a little bit. Wherever you're actually in the weeds of leveraging the tools and the tactics so that you make sure there's tangible results at the other end of it versus just saying like, hey, I'm a storyteller, and you could take and leave whatever you want.
[00:20:10] Speaker B: Yeah.
[00:20:10] Speaker A: And then the other side, actually, sorry. Because that's one thing.
[00:20:13] Speaker B: No, no, go for it.
[00:20:13] Speaker A: The other side of it is that frameworks and kind of mentality, I think, don't change that much. If that makes sense.
[00:20:20] Speaker B: Yes.
[00:20:20] Speaker A: Right. Like, if I'm looking like 20 years out, the mentality at which I approach sales, I think I'm pretty confident it's still going to be effective because I'm all about being brutally transparent, honest, confident in your gaps to make sure you could close a big deal. And I think those are very, like, psychological human tendencies and that help close enterprise deals that are also hard to overcome, you know, because a lot of people think you have to sell something that's not there to keep engagement. But that's just like, completely not true in my experience. And so I think marrying that, like, strategic mentality and unique kind of approach to adopting a mentality that's undeniably successful, like that married with. Okay. Staying fresh with the tactical day to day, I think is a killer combination, or at least I hope it is in the way that I'm trying to execute my business.
[00:21:16] Speaker B: Yeah, no, it makes sense. Makes sense.
[00:21:20] Speaker A: Yeah. Does that jive with you? Is that how you deal with, like, how are you dealing with imposter syndrome?
[00:21:24] Speaker B: Actually, yeah. I think part of it is I'm definitely just figuring it out as I go. And that's part of the kind of pitch and disclaimer is, yo, this is not my full time deal. I only will ever have twelve clients while I'm running castos because that's kind of my deal with myself and, you know, our investors and stuff is, this is just a side thing. It's a few hours a week, and I'm in the weeds every day figuring this out. So I know, like, one of the things that I bring value in is that, like, I'm literally in sales calls and running sales, sales process.
And so, like, I kind of overcome imposter syndrome just by being busy and in it, I think I will have much more the day that this becomes kind of like my only thing.
So I'm deferring it, I guess, for now is part of it.
But I think what I was thinking about as you were wrapping that up is I think there's an aspect to kind of like staying hungry and like wearing the skinny jeans and all this kind of like. Right. Like, I gotta keep myself moving. Yes. No matter what. Like, whether I'm kind of doing this as a side deal or full time or castos or whatever, like, I got it. And maybe it's more applicable in my time at Kastos, where I've been podcasting for ten years. You know, this will be episode 321 or something.
[00:22:54] Speaker A: That's impressive.
[00:22:55] Speaker B: And, like, when I get on the phone to talk to people about podcasting, I can go, well, fuck. Back in my day, you know, we were using Skype. Literally, we were using Skype. Right. And that makes me sound like an ogre, right?
[00:23:09] Speaker A: Yeah.
[00:23:09] Speaker B: Or I can go, the new, you know, coolness is riverside, and you want a cool light like this in the background. It gives some depth of color. And we're big on video because that's new thing.
[00:23:19] Speaker A: And, TikTok, I love your setup, by the way. I could use some consult.
[00:23:23] Speaker B: Thank you. Thank you, thank you. I honestly, the light makes a huge difference. Like, it looks really boring without the light.
[00:23:30] Speaker A: Yeah. Okay. Okay, that's good. I'm gonna have to. I'm gonna have to get from you, like, what brand and all that.
[00:23:35] Speaker B: Yeah, yeah, yeah.
Cool. So I want to segue a little, and this is going to be a magic segue, if you could, from sales and sales coaching to. You are the last member of our LinkedIn series, and I wanted to have you on to talk about sales in LinkedIn, because you're obviously, like, a sales professional.
The answer to how can I grow my business to every single one of my clients is LinkedIn, the LinkedIn and YouTube. Right. And there's this kind of magic that happens between the two.
Well, I guess, first, do you think LinkedIn is a viable channel for pretty much every business?
[00:24:17] Speaker A: Oh, great question.
I want to say yes, but I'm also probably very biased because I work with b. Two b clients. Right. So my constituents, you have to be selling into enterprise organizations who are trying to buy your product from their business budget.
[00:24:35] Speaker B: Perfect.
[00:24:36] Speaker A: And that's perfect for LinkedIn. Right. I hesitate because it matters where your watering hole is. I like to use that phrase, where are people talking about their problems? And for businesses, a lot of businesses are starting to talk about their problems on LinkedIn or looking for opportunities to their problems on LinkedIn. Another, I think, channel that's worked for me at Twingate, my prior company was Reddit because there were a lot of Reddit threads where people were complaining about VPN, and we happen to have a solution where we could replace VPN. So I think that's the question that founders should ask for themselves when they're looking to invest in a platform. And where are people having conversations about problems you can solve? Right.
[00:25:20] Speaker B: Yeah.
[00:25:20] Speaker A: And then that married with, what's a platform that can bolster your personal brand in a way that marries Business like, that's also really important because, you know, on Reddit, sure, we had some opportunities to get leads, but Reddit's not really in it to make unique profiles of users. Right. Yeah, there's very limited functionality there. It's literally a forum board. But LinkedIn, I think the reason why it's special is because I've had the opportunity, and a lot of my clients have had the opportunity to really showcase their personality and values and perspectives beyond a product, which I think is key as well, to find in the platform you want to align with when, when looking at building out a digital footprint.
[00:26:05] Speaker B: So I was talking to a prospective client last week who sells quite a b two b solution, and we were talking about, hey, LinkedIn. Right? That's the nail. I'm a hammer. Let's go.
And they were like, Craig, how am I going to talk about, well, I'll just say VPN Solutions and cybersecurity on LinkedIn, it's a freaking boring. Nobody cares. I'm going to pull my hair out.
How do you. I mean, because I consider myself kind of lucky. Like, I get to talk about either sales and sales coaching, super fun and applicable to everyone, or podcasting and content creation, super fun, interesting to everybody. If you, if, you know, if you're a listener to the show and they're like, I sell municipal planning software.
[00:26:52] Speaker A: Yeah, yeah, I.
[00:26:54] Speaker B: What do you say?
[00:26:57] Speaker A: I think the key is being able to actually translate what you do in terms that a broader audience can understand, because even something like municipal software planning software, you said there's going to be multiple stakeholders that need to make a decision on that particular product. I'm guessing at that point it's not necessarily, okay, how do I sell this to people who know what it is? It's like, how do I actually translate the business value to a broader audience so that the sale becomes easier? And I think that's also like what I'm doing with sales coaching, too, and what we did with VPN replacements as well. It's like VPN replacements isn't just relevant for security and engineering teams. The everyday employee should understand why their current VPN sucks so much and why it's actually impeding on productivity.
And so I think, like these digital platforms, whether it's LinkedIn or something else is an opportunity for you to uplevel your product so it's relevant to the CFO the same way it is to your champion or executive sponsor.
[00:27:58] Speaker B: Interesting.
[00:27:59] Speaker A: So I think that muscle is really underrated for founders who are starting enterprise sales. They think, okay, well, like, I know the pain points and I know the decision makers actually, like, today, the pain points are various regardless of what product you're solving. And the decision makers are a lot broader and deeper. You know, it's not enough to sell something to one person because with the economy going up and down, like, purse strings are a lot tighter, I would say.
[00:28:29] Speaker B: Yeah.
[00:28:30] Speaker A: And so that's what I would say. It's like, you need to start building that muscle online to up level your message in a strategic way so that your budget is also strategic for your product.
[00:28:42] Speaker B: I'm gonna, I'm gonna paraphrase on a tangent, maybe a little bit here.
A big thing I like to talk with folks about in my sales coaching and just content in general is this, like, discovery and agitation phase of a sales call. Right. Because it's super important. It's a little bit of what I'm getting from what you're saying is, like, you're definitely not talking, like, features and benefits.
You're not talking, like, market news, which would be like, super high level, not even problem aware if you're thinking about the customer buyer journey, but. But kind of like they got a problem and you just want to agitate or I like, you want to pour some salt on the wound a little bit. Because what I find is the more, and this is in stark contrast to what we were saying before about being an authentic sales call, the more I can help the customer understand the shift that they're in.
[00:29:36] Speaker A: Yeah.
[00:29:36] Speaker B: The easier it is to sell something.
[00:29:38] Speaker A: Yep. Yep.
[00:29:39] Speaker B: Right?
[00:29:40] Speaker A: Yeah.
[00:29:40] Speaker B: And I do that in a very genuine way, but I give the example a lot of, like, oh, I want to. I want to start a podcast. Why do you want to start a podcast? Well, I want to grow my thought leadership. Cool. Why do you want to grow your thought leadership? Well, I'm writing, I've written a book, and I'm going to launch it next month. Okay, cool. Like, what happens if that doesn't go well?
[00:30:00] Speaker A: Yeah.
[00:30:02] Speaker B: Whoa, cool. That's a. That's a big problem. And then, like, me selling my little podcasting solution is really easy relative to that.
[00:30:10] Speaker A: Yes.
[00:30:11] Speaker B: Then I just want to, you know, be the next big thought leader.
[00:30:16] Speaker A: Yeah. Yeah, exactly. There's. Without pain and without a huge impact. There's no budget, right? So I see. I see content as surfacing that pain and getting people to think about where that pain is. Because sometimes you have buyers who are like, oh, I know I have a problem. But then you have buyers who don't know they have a problem. So how are you going to warm them up? And I think in a lot of ways, it's educating them on what happens if you don't work with somebody like me as a sales coach, let's say, yeah. So a lot of my posts are about, hey, like, I went through this deal, or if you're coming across this problem with, you feel like you're at the finish line of a deal, but your deal stalls, what do you do? Right? Then people start thinking, okay, well, I don't have that problem now, but when I do, I remember that post and I'm going to go to reference it, hopefully in that ideal scenario.
Or I'll talk about a client who didn't want to have sales coaching, but then they worked with me and something happened, you know, so you're incepting, I think, where the pain points are going to be in a future state so that it's easier for them to reference and find you when they actually do feel like they need to address the pain point that's always been there.
[00:31:26] Speaker B: Yeah.
[00:31:26] Speaker A: And the other thing, too, about, like, it's municipal planning software, you said, as an example.
[00:31:30] Speaker B: Yeah, yeah, yeah.
[00:31:31] Speaker A: Okay, so think about, like, you know, do you know Brax and Ramp, these corporate credit card companies?
[00:31:37] Speaker B: Yeah, yeah, yep.
[00:31:38] Speaker A: So, like, those founders could have taken a similar lens. They could have been like, who cares about corporate credit cards, right? Or who cares about expense reporting? All of a sudden, ramp is like, one of the hottest brands out there, and what do they do? Obviously, they're just not, they're not just a corporate credit card, but they. They made that world ubiquitous to every single person that they could sell to. Top down. Right? Brex is a cool company to the CFO, but it's also a cool company to the people who are logging into or, sorry, not Brex ramp. My wife works at ramp.
I'm unconscious or maybe consciously plugging it, but yeah, you know, like, that's the kind of thing I think about when founders are like, this might not be relevant to this channel. It's like, no, actually, you have to make it relevant by figuring out the unique advantage you have wherever you're the clear winner and the clear, like new kids on the block that are fresh and cool in your space.
[00:32:38] Speaker B: Yeah, yeah. Okay, okay.
I think one of the big questions that I have, and I think everyone has, is, okay, cool, I'm putting out content. I'm doing my thing. I'm kind of agitating the pain and to say, like, developing the problem a lot.
But, dude, Peter, like, I ain't got no leads. I ain't closed any deals. Like, what, what's up, man? Like, how do you, how do you, and how do you coach your clients to bridge that gap? So I think that's the secret with LinkedIn is like, cool, I got. And I'll just give some context of how I think about it as opposed to cold email because it's kind of similar. But the difference is you got a whole bunch of chances to make a first impression on LinkedIn.
[00:33:21] Speaker A: Yeah.
[00:33:21] Speaker B: And you got a whole much more context, your profile and your posts and your comments and all this kind of stuff. And somebody can choose to engage with you based on any of those or on a DM, which is the cold email. Yeah.
So, like, the passive stuff aside, right. Let's just assume we got your content going, and we've talked about that in the series a lot. But then, like, how do you, how do you go make business out of this?
[00:33:47] Speaker A: Yeah. So right now I'm actually doing this with my own practice, which is I've hired somebody to, and I've given this person parameters to say, hey, this is my ideal customer for me. I love folks who are CEO's founders. Less than two years in the seat. Hopefully they have some venture funding in a seed round.
They also have an engineering or product background.
And, you know, they're in the United States because I want to kind of control my schedule to the states for now.
And so this person comes with hundreds of contacts, and you start to kind of develop this list of people you should be reaching out to on LinkedIn. And then right now what I'm doing is I'm connecting with as many of those folks as possible.
And I don't even put a message in the connect request because my goal is because I have so much content, I want them to look at my profile and be like, why is this person reaching out to me?
And when, you know, a portion of those folks will accept, some will be like, why is this guy reaching out? I have no idea who he is. I'm just going to decline. But some raise their hand and there's signal number one that I generated. Okay, so a portion of folks have accepted my invite. Then what I do is I research them more deeply. I'll go to their website because now I have the signal to say, these folks might be worth my time. There's no way I'm going to be able to research 200 leads a day because it's not worth my time because I'm on coaching calls and I want to make sure my current clients are happy. So anyways, I research the subset that actually accept my invite, and then I reach out with a personalized no, not anything where it's like, hey, Craig, I see you at a bachelor of science at X University and bulldogs. Not anything like that. But oftentimes I'll have mutual connections. I'll say, hey, Craig, I noticed we were connected with Lon, who's a venture capitalist at basis set. I actually helped a lot of our portfolio companies go from zero to one, so I thought I'd reach out.
I still don't ask for a meeting, by the way, at this stage, what I say is, since I've helped a lot of companies, I've seen three common founder led sales mistakes that are made, and I created a short deck and a recording on that. Do you want to see it?
So I'm not giving anything yet, but I'm like, hey, I might have something of value, which are three mistakes I think you probably shouldn't make a if you care about sales and you're doing founder led sales.
And so portion of those folks respond and they're like, hey, Peter, actually, I'm really interested in seeing that again. The goal is for them to even, like, get more intrigued and be like, okay, this person has something. Let me go to his website, let me look at more LinkedIn posts, maybe. And so I send that artifact or that collateral, and now we're in a very genuine conversation where I'm trying to provide as much value before I say, hey, like, what did you think about that piece of content? And do you want to get on a call with me? And all throughout, I'm asking little questions where it's like, hey, like, it's all about coaching style. Have you thought about a coach before?
And then when you get on a call, they've hopefully looked at, you know, five to ten of your LinkedIn posts. Some get on a call. By the way, Craig, thanks to you for helping me get this decoding sales podcast started. Some are like, hey, I've listened to six episodes already.
And then the conversation is not really, it doesn't feel like a stodgy first sales call. It feels like, okay, we kind of know we want to work together. Let's just figure out the details and let me ask a few more questions that I wasn't able to over the LinkedIn DM series. So that, I think is like a really proactive way to get the process started while still having it not feel like the traditional cold outbound. Yeah. So I'm curious to me if that. How that sounds to you or.
[00:37:37] Speaker B: Yeah, well, first, it sounds mostly really authentic.
You are doing what LinkedIn is designed for, which is just connecting people. And it's just like you would do if you were at a networking event or a coffee shop or a conference or something like that. So, like, yeah, I really like it.
I'll tell you. And just like, transparently I follow a similar approach.
[00:38:01] Speaker A: Nice.
[00:38:02] Speaker B: But have fallen short at kind of that last step a little bit, which is I use some software to automate this, which, again, I've said it on the podcast, it's technically against LinkedIn's terms of service.
[00:38:15] Speaker A: Yeah.
[00:38:16] Speaker B: So do it or don't do it. I don't know. To me, it's like an acceptable risk. Yeah.
Either way.
[00:38:22] Speaker A: For which platform you use?
[00:38:24] Speaker B: I use dripify.
[00:38:25] Speaker A: Okay, cool. Yeah, I've heard of that for sure.
[00:38:27] Speaker B: Yep. So dripify, extendy or extenda.
[00:38:31] Speaker A: There's like, lem list. There's like.
[00:38:33] Speaker B: Yep.
[00:38:34] Speaker A: All sorts of these, right?
[00:38:35] Speaker B: Yeah, yep, yep.
Achieves the same thing you're talking about. Right. I could hire the guy who does it and reaches out to 20 people a day or just do this. I probably will do the latter when I get a little more sophisticated, because I think there's some stuff in there, right. But I pulled the list, right, from sales navigator.
And I got a list. I reach out to a whole bunch of people.
If they accept it, I wait a couple of days and, like, no note, right in the connection request, just like you're saying. I want them to view the profile.
If they accept it, I wait a few days and I send them a message. And this message is killing it. Nice.
[00:39:19] Speaker A: Yeah. What is it? I'm curious.
[00:39:21] Speaker B: It says, heya. H e y a. Because I want it to be kind of casual. Heyadhe first name.
Cool to connect.
How is growth going these days? I know it's a tough environment for a lot of folks.
[00:39:36] Speaker A: Mmm.
Yeah.
[00:39:38] Speaker B: And, dude, it's, it's.
[00:39:41] Speaker A: I might have to deal some of that, that tough environment piece. It's hard.
[00:39:45] Speaker B: Yeah, yeah. I mean, because it's like, it's universal. Right, everybody. And then the interesting thing is I get a bunch of people, like, puffing their chest out and they're like, oh, we're fucking killing it, and it's great. And I am so busy. I just need people to keep up with the man, and I'm like, awesome, dude. Like, really awesome. Yeah. I mean, what. What? Back to authentic authenticity is like, that's what I would say to you. Right? It's like, peter, dude, how's it going, man? You know? Like, yeah, what's up? And I think that. I think that's where doing this well kind of shines.
[00:40:16] Speaker A: Yeah.
I think reaching out to folks is also part of the qualification process, too, right?
[00:40:22] Speaker B: Yeah.
[00:40:23] Speaker A: Like, you don't want to be taking a meeting just because. So for those folks who come back to you who are like, it's so amazing, like, I'm doing so well, you probably will, like, have second thoughts on getting on a call with that person, right. Because it might just be all with them, just, like, showing off how well they're doing, and they probably won't be ready for your help. And so I like that message because then it self qualifies for people who are having issues. Right. Where you can actually step in and help enable some support around.
[00:40:52] Speaker B: Yeah, yeah, yeah.
So. But the last step that you're talking about is where I've just fumbled the ball. Like, I don't have a thing to do after. After that. Got it.
[00:41:04] Speaker A: Got it. Yeah.
[00:41:05] Speaker B: And so, yeah, I'm just gonna steal what you did.
[00:41:07] Speaker A: Yeah, yeah. I've read a lot around where people. It's. There's opinions around LinkedIn outreach, too, and some people are like, hey, just tell me what you want on the first message that's, like, not really, like, authentically me, because I want people to actually, like, I want to create this poll effect versus me trying to force something on their calendar. But then I think there's, like, a good middle ground, too, because you also don't want to keep giving value and not ask for a call. So I kind of. I feel like I'm in the middle where I want to provide a little bit of value, but I don't want to give free advice forever, especially if I feel like there's a fit with the folks that I'm reaching out to. And right now, I don't do any automation. I might think about doing it because I want them to also see that I'm committing time to, like, learning about them. And so I'd rather spend, you know, 15 minutes on a single, highly qualified lead than 15 minutes on, like, ten. Right. But I think eventually, hopefully, that'll be a good problem to have if I need to automate. Hopefully that means my business is at another level, but right now, I'm just kind of doing things that don't scale so I can, like, learn and make sure I'm conveying, like, the right authentic energy.
[00:42:18] Speaker B: Yeah, yeah. No, I mean, I love it how you're kind of giving people a very authentic option to take the next step. And that's the hard thing. Right. We started the conversation talking about, like, why people suck at sales, and me included, is like, it's awkward to go from like, hey, dude, how's it going to.
You want to go on a date like that? That's kind of what we're saying is like, hey, nice to meet you.
[00:42:42] Speaker A: Yeah.
[00:42:43] Speaker B: I want to draw this line over here to you being my client.
How do you do that? In a genuine, authentic, real not pushy way. And that's just bridging that gap is challenging, I think. Kudos to you. Yeah, yeah.
[00:42:58] Speaker A: The thing that I think about is, and I think you could probably have the same mentality, because you provide so much value on that call. Like, even if I didn't sign up for castos, I feel like I would have learned a lot. And that's something I keep in mind for my own practice, too. It's like, yeah, at a certain point, if I know the company and the background of the founder, I'm like, I know even in a 30 minutes call, I can provide at least one or two nuggets that are going to help their sales. And so that's also the other thing I know I'm going to be providing value. And it's not just a sales pitch on a sales call. Right. It's a lot of advice giving, too, to continue that same feeling of, okay, I got information from this guy. It's a continuation of continuing to get more, more information.
And so I think the arc of the sales call is more like 15 minutes of giving value and then maybe like, ten minutes of you asking for the business.
[00:43:53] Speaker B: Yeah, yeah. Interesting. I'll tell you what I do these days, and it definitely doesn't scale, but I just like it. I'm like, whatever.
So have a 30 minutes, initial call, discovery call. It's all about them. It's just, hey, what are you going through? Tell me about your process, blah, blah. About five minutes before that's over, I go, cool. Like, looks like we could be a good match. Really. The next step is like, I'm going to give you a free coaching call, and it's an hour long. And so this is like, your trial, right? Instead of me just telling you what this is like, you get to experience it over here. And so, like, I have the time to where I can do this. It doesn't scale. Right.
Um, it feels really good to me because I could spend, you know, 25 minutes just understanding what's going on with someone to where then I can go into that coaching call next week with a ton of context and really help them out. Um, so I would.
[00:44:48] Speaker A: Can I push you on something?
[00:44:50] Speaker B: Yeah.
[00:44:50] Speaker A: I would experiment with the kind of, like, give maybe 15 minutes, shorten that discovery. Okay.
Give some value. Make sure you look really good on that intro call, too, which I'm sure you already do just by the way you're asking questions. And then experiment with saying the trial is a paid consulting call.
[00:45:10] Speaker B: Okay.
[00:45:12] Speaker A: I've had a lot of success with that where I do trials, too, but my trials are just paid sessions.
[00:45:17] Speaker B: Okay.
[00:45:18] Speaker A: And then what I do on the paid session is make sure I'm bringing my full energy.
I try to do that every call, but it's a different kind of environment because you're trying to get the renewal.
And then there's inevitably action items there that, you know, they need to follow up on with, like, a pack of coaching sessions after that first session.
[00:45:37] Speaker B: Yeah.
[00:45:38] Speaker A: So I would give that a shot. I was talking to my best friend who also was in this similar situation where he's just giving so many advice calls and he's unsure how do I turn that into paid. And the best way to do that is to set the expectation that after the intro call, anything that you give value after that has to have a price tag on the.
[00:45:56] Speaker B: Yeah, yeah.
That is.
[00:46:00] Speaker A: That your time is valuable, Craig. You know, you're wealth of.
[00:46:02] Speaker B: No, it is. Yeah, it is. It is. And it's that evolution of, of confidence, I think is, is what you're talking about is you're. You're kind of two steps ahead to where you're like, yo, I know. I don't do, I don't lace them up for free anymore. Right. You gotta pay to see the goods.
[00:46:17] Speaker A: Yeah. Too. Is, you know, it's the impact that you're creating. Right. So you. It seems like you have great questions around what the impact is of not having your support then a trial, you know, I don't know how much you would charge, but let's say, like, hypothetically, you're like, hey, I'm going to charge $500 for the trial session. And they're cagey about it. Then you might be like, well, dollar 500 could turn into however much revenue you said you wanted in the call, right?
[00:46:46] Speaker B: Yeah.
[00:46:46] Speaker A: So, like, if you're trying to get to a million in revenue this year, spending $500 on a strategic call, seem like an outsized request.
[00:46:55] Speaker B: Yeah, yeah. Love it. Thank you. That's great. Yeah, of course.
[00:47:00] Speaker A: Hopefully that helps. I want to hear level up. Yeah, yeah, yeah. I want to hear how it goes.
[00:47:05] Speaker B: Cool. Cool. Peter, this is amazing. I think it's a really cool place to wrap for folks who want to connect with you. LinkedIn sounds like the obvious place.
[00:47:13] Speaker A: Yep, LinkedIn would be good. Also, my website, it's Peter on.com, my full name.com dot. So either way.
[00:47:20] Speaker B: Yeah. Awesome. Cool. Peter, thanks so much for coming on. I appreciate it.
[00:47:23] Speaker A: Cool. Thanks, Craig.
