The First Guy to Lose to Salesforce (And What He Did Next) with Kris Lawson

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Now let's get on with the show. Hey everyone, welcome back to Make It Happen Mondays where we talk about sales, business, entrepreneurship, personal growth, mental health and everything in between with guests who I truly respect and I think make a positive impact on the world around us. Now full disclosure on this one, Chris Lawson is the founder and CEO of Ruby at HeyRuby.ai and I sit on their board of advisors. So Chris and I do work together. That said, this conversation went way beyond Ruby. Chris was one of the first of four employees at Salesforce Canada, where he helped scale that office from four to over 800 people. He was the first hire at Snowflake Canada and took it from zero to 35 million in ARR and was there for the IPO.

And he's got a co-funded investor syndicate called Snow Angels backing data and AI startups. And he's the father of four, including spontaneous, identical triplets, which we absolutely got into in this conversation. So as always, we start with the origin story and he talks about how he was selling newspaper subscriptions at 12 years old, raking in about 500 bucks in tips. And that's really where he got the real hook for sales. And then landing actually landed a $250,000 national contract for sign letters at Cineplex Odeon at 17 years old. So I can't imagine what the commission check on that one would have been, but at 17, are you kidding me? Now, he was also the first person at Oracle to ever lose a deal to Salesforce.

And it was absolute shock because who is this company? What's going on? So he got asked to do a competitive Intel presentation for 150 field reps. And then he got cold called by Salesforce headhunter two weeks later and joined Salesforce Canada. And then we got into spontaneous, identical triplets. Like, are you kidding me? He had this, he went to the doctor and, you know, they had one kid and they were expecting another. They thought they just wanted two. And the doctor was like, uh, you got three in there and they're identical. And he got out, obviously in shock. There was like this tears for fears moment in the car that really just solidified where they were at this point. But, you know, obviously changed his life forever in all the right ways, moved the family out so they could have a little bit more room and around his parents and stuff.

So that was a real life changer, but all the blessings all the way. And then he talked about, you know, then we got back into business and talked about this builder buy fallacy right now that's going on with AI. Cause every idiot now can like me, uh, can develop apps. And they think it's a lot easier than it actually is. So, you know, he's what he's building with Ruby is this ecosystem for sales professionals to have access to every piece of information they need to sell more effectively. So this is kind of one of those questions that I have a lot, which is, Hey man, I could probably build the vast majority of this just in Claude, but why would I now, you know, go purchase it? And I think that's a huge objection that most reps are, I don't think, I know that's a huge objection.

Most reps are faced with right now. And the one question that came up towards the end, which I was really curious about, and I wasn't planning on asking was what AI does to all these sales methodologies, you know, Sandler Miller, Miller Hyman, medic, you know, challenger, all these ones. And I've, I've never been a methodology guy. I've always tried to take the best of all worlds. And I think AI now is, is the best of it because it can pull the best of all worlds and you can create your own sales methodology. So we got into all this stuff and a lot more. I hope you enjoy the conversation as much as I did. Let's make it happen. Chris Lawson, welcome to the make it happen Monday podcast. My friend, how are you today?

I'm great, John. Thanks for, thanks for having me. I've been looking forward to this for a long time and listening for a long time. You're a, you're a legend, man. I'm, I'm glad to spend some time with you. Thank you. I think I've just been around the block for a little while and people getting familiarity, I think is a good thing. So I don't know about legend, but I appreciate it, man. I'm looking forward to this because we are going to talk, you know, a lot about what you're, you know, what's going on right now, specifically from the buyer perspective. And it touches on something that I've been screaming about, right? All these AI tools and everybody's scared about automating sales reps. And that's not what I'm worried about.

I'm worried about when the client wakes up and realizes that they don't need us. So we're going to get into that. But as always, with all these shows that I start, I always love starting with the kind of the origin story, my friend, like what made Chris, Chris and, and, you know, parents influence all that fun stuff. I know you were selling pretty much since you came out. So, you know, where'd that bug come from and how did it evolve? And then we'll get into kind of the decisions you made for school and everything else along the way. So, uh, well, first of all, I'm a nice, friendly Canadian. So born in London, Ontario, Canada. Um, and I grew up in a pretty middle-class family where we had enough to be comfortable, but not enough to go beyond, uh, you know, more than like a trip a year.

And I didn't really, I didn't go on my first airplane until I was 12. And I didn't again until I was, um, 19 and paying for it myself. So I always wanted to, to, to kind of get out there and kind of do more with, with, uh, my life and, um, had a really early inkling of, of, of selling and like being, having kind of a, a, a natural, um, interest in, in working with people. Um, but also, you know, natural interest in, in getting people to agree with me, kind of follow on this path. Right. And I realized early, even in selling, um, like newspaper subscriptions, which was my right first sales job that if I was personable and I had great, great, uh, conversation skills and so on, I would get this $20 tip at Christmas.

And, you know, when you're 12 years old and this is, you know, a long time ago and you're 12 years old and you're raking in, uh, $500 in Christmas tips, uh, selling newspapers. You're like, Oh, this, this whole thing is, yeah, you're rich. You're loaded. Dude, this whole sales thing's really interesting. So over time I started to do, uh, more selling, uh, sold door hinges. So I, I, I basically worked at the desk, uh, selling door hinges and, uh, sliders and things like that to contractors, uh, at a company for, for a year. Um, I was a, I was a field rep. Get this, I was a field rep at 17 because someone I knew in my network thought that I could sell sign letters. He's like, I'm going to give you a cell phone.

Nobody had a cell phone back in 1997. Like I got a cell phone before any of my friends. And he said, I'm going to give you a cell phone. I screen print sign letters. I want you to go and sell sign letters all over Ontario. And so I basically in the summer just drove around in my 1986 Toyota Supra with the, the Targo roof off. Right. And I would drive around, I would go to these sign sign companies. And I realized, I'm like, who buys the most sign letters? And it's like movie chains, a movie chain. Right. Do they have at the time? Like they have these obviously signs putting up new sign letters about movies that are happening. And I'm like, I'm going to go to Cineplex Odeon, uh, which is the largest movie chain in Canada.

And I want to go get their sign sign letter business. And so I got a meeting, um, at, uh, at 17, got into there, brought my, brought my boss, the owner of the company when we won the contract for sign letters for the national theater chain of, of, uh, of theaters in Canada. It was crazy. It was like, uh, it was like a $250,000 contract and I was seven. Holy smokes. Yeah. So that's, that's where I'm like, okay, sales good to go. You know, did some other stuff like Gatorade and Snapple and merchandising. But when I got, by the time I got to university, I was like, okay, I think, I think this is what I want to do for sure. Love that. And you, you got a, so you got a BA in economics. It was a, no, where'd you go?

Sorry. Laurier. Yeah. There's a great, yeah, great business school in Canada, Wilfrid Laurier University. Yes. Hey, taking a quick break here to remind you to check out some of my sales training programs at jaybarrows.com and use discount code podcast for 20% off the individual packages. If you're not interested in training or you don't think you need it, then you can still support me by leaving a five-star review on your favorite podcast platform or G2. If you've already gone through my training before, you can also sign up for my newsletter on jaybarrows.com where every single week I put out a newsletter that breaks down what I'm learning out there. Some of the new tips and tools and tech and resources that I'm coming across and some stories from the streets of train wrecks that I go through and stuff not to do.

So if you could do one of those things, either sign up for the membership, give me a five-star review or follow me on the newsletter. It would mean the world to me. Thanks for your support. Now let's get back to the show. What did they teach you there? Because I'm struggling with college these days and I've never been kind of an undergrad fan because I think it's a social education, not an actual education. But were there things that you pulled from your experience at that college that still stick with you today? Or was it kind of your typical? Because I have a similar upbringing as you, like kind of middle class, those type of things. Love sales. Got into it. Kind of got through college just because, right?

And I don't know if I, probably things that I look back on college and say, okay, foundationally, maybe some of those things made a difference. Learning how to learn that type. But I think it was a lot more of the EQ stuff of me going out, meeting friends, engaging fraternity stuff. So what was your kind of, what was the value of college for you? So I think there's two parts to this. So one is like the typical learning, right? The, I did a business degree, which is a pretty, pretty generalist type role. So you've got, you learn marketing, you learn organizational behavior, you learn finance, all those types of things. No sales course as, as in post-secondary, right? We've talked about this before, I think in a few conversations we've had, it's like, there's no, there's no formal sales training that you get in university.

I knew I wanted to be in sales, so I kind of picked other courses that would round me out from a, from a sales perspective. So psychology. So I minored in psychology, understanding cognitive psychology and how to deliver messages that actually stick with people so that you're appealing to the human brain and how they learn. And then of course, like social psychology and persuasive psychology, Cialdini, I think is his name, the guy, probably Cialdini. I've recommended Robert Cialdini probably 50 times in my career. Oh, you got it? Yeah. Yeah. Exactly. Yeah. Talk about door in the face, face in the door. Love that, love that book. I think it's a, it's foundational to what we do in the sport that we were in.

So that learning was big, but the reason why I picked Laurier and I wanted to go to this school was because of the co-op program. So they actually had a co-op program, um, where you would get placed into businesses and work within those businesses. And I think if this, I look at that with my kids, I have, I have, uh, four teenagers that are going to be going to school down the road and I'm looking at co-ops and saying, how can these people, how can my, these people, how can my kids get on the ground training? It was crazy though, John, I got to say, cause I, I experienced one of the most interesting, uh, co-op terms, I think of, of, of anyone. Um, I was, uh, I, I became, I was in a sales, they created a sales position.

So I interviewed with this company called Pixstream. They, they created a sales position and said, I think we should put this kid in sales. Uh, and we're going to just make this position, have him work there for the summer. And this was, we were selling, um, telecom equipment that allowed you to compress video feeds and put video feeds over twisted pair, like telephone lines so that a telephone company could become a cable provider. Right. That was like, that was the, the, the, the confluence at the time of, of those services. And at the end of the co-op term, they got bought by Cisco. For $300 million or something like that? $300 million and $300 million in, in, uh, in 2000 was obviously like a significant amount of money.

And I saw these, these, these three guys, um, uh, Brad, Mark and, and, and, uh, they, they had started this company three years earlier and they just pocketed $30 million. So I was like, Oh man, tech is the place to be. Tech is the place to be. But then the other part of that story, which is funny is though, so I go back to school for four months and then I go back to Cisco, right? I go back to Cisco because now I'm working for Cisco. My previous company had been acquired by them. And at the end of that term, uh, on the last day of my work term, they fired everybody. They brought 250 people into a room and they said, I'm sorry, the internet bubble has crashed. You are in more of an exploratory, uh, technology.

We want to focus on routers. And I saw 250 people get fired. And so I saw in, in, in, in university before my third year, I saw the highs and the lows of the tech industry, like great visceral in front of me. And I think those are like, you know, from a college perspective, like you can't get experience like that, um, without, without finding co-op positions that take over that. And it's just, it was a bizarre situation, but I took so much from it. That's, I mean, that's an educational in and of itself, right? That's worth the price of admission for college to get that experience and be on that ride up and down. Poof. Yeah. Cause I, I remember, you know, I had something similar when Xerox, I, I, I think the one wake up call for me was when I worked at Xerox and I got, and it was right in, it was like 2000, you know, uh, 99 and the boom, you know, whatever.

And then all of a sudden I got in and like Xerox's stock was like 120,000 or $120. Right. And then, then all of a sudden the market started to crash and they went down to 60 and people like, Oh my God, it's never been this low. You should buy, you should buy it. I'm like, I don't know about that. Uh, you know, 30. And then, and I watched people who are lifetime Xerox people who had had all of their money, their 401k, all of it in this. And it, I watched like people who are about to retire, look at everything evaporate. Cause it went from one 20 to 60 to 30 to 15. And it, and then, you know, obviously it rebounded after that, but I was like, these people were decimated. And so that to me was like a corporate wake up call, like, wait, okay.

I can't put all my eggs in one basket and, and, you know, whatever. But that was kind of the, the early learning lesson for me, but nothing like rocket ships sailed, you know, fired 200 people. So that's fantastic, man. Cause then after that you went to Oracle Salesforce micro, I mean, your, your resume here is pretty impressive with all the different, uh, logos here, but Oracle was the first one, right? Is that, was that the first job out of college? Yeah. The guy, the guy at, uh, pick stream who I, I admired the most. He's a sales leader named Bill Jakes. Bill's amazing. He was my, he was my coach there. Um, and I said, I'm, I'm going into sales. What should I do? And he's like, just follow the margin, right?

The more margin a company makes, the more likely they're going to pay you higher commissions because they're making more profit. And he's like, the most, the best margin is in software and make sure it's direct. Don't sell for, for a reseller. And so, um, I found this opportunity at, I was like, okay, well, Oracle, like that checks all the boxes. And I was hired at Oracle for, uh, what they call the BDCs outbound BDR cold calling there. That was the first job that I had. And fun fact, like they were actually looking, it was the first BDR organization they ever built for business applications. So this was ERP and CRMO bound, not database. Yep. And they were like, we need to hire MBAs. We need to hire people that have a deep business understanding and can talk to CFOs because we want to sell Oracle financials and they hired me like 22 at a school.

And again, this comes back to like, I I'm so adamant about the co-op experience and like finding schools that have that co-op experience because I, I was, I came out fully baked with, uh, experience that they were like, oh, cool. We could, we could put this kid on the team. And I was, um, you know, 22 working with like 30, 35 year olds and, and just hitting the phones and getting that amazing sales Academy that is, uh, Oracle. Yeah. And getting that, that's why I always tell kids coming out of college. I'm like, if you don't know what you want to do, just get a, get a logo, you know, go work for a logo. Um, and the reason for two reasons, usually they have a training, you know, and you go through the process, but also when you go look for your next job, like you're not explaining what that company was like, oh, Oracle, great check box.

But if you work for some small ass startup that nobody knows, you spend half the interview telling, you know, explaining what the company did and what the, you know, whereas like, oh, like I got, I got lucky. I was DeWalt and, you know, in Xerox. And so everybody knows what both of those, and I had Xerox being like, oh my God, the eight week sales training program. Right. So, but then you, you, I think you noticed, uh, that you were starting to like, there was this little company Salesforce that was starting to eat your lunch here. And, uh, this little SAS thing was, was starting to fly. And I, and there was something in here that I was reading that you, let's see, uh, what you competitive Intel presentation you put together because it seemed like you were, did you put together a competitive Intel for, did you say like, all right, you know what?

Oracle's kind of like, I got to go with like my risk profile. I got to go with the Salesforce cause I'm seeing them all over the place. Walk me through that transition. Cause in, in how you did your kind of business plan, if you will, a competitive analysis. Yeah. So I'm, uh, so I did the BDC role, right. Uh, the outbound BDR and then they moved me to inside sales. So I was actually running my own, my own deals. Um, and I'm the first guy. I was the first guy at Oracle to lose to Salesforce.com first guy ever. No way. Oh shit. That's a, that's an interesting distinction. I like that. I was, I was the first, I was the first guy and, um, my bosses were like, who is this company? Like, well, what, what is this company?

How did they possibly steal CRM business from us? And they said, you got to go investigate them, go, go find out everything about them. And then we're going to actually ask you to do a presentation for 150 field reps, uh, in Boston, like, you know, two weeks from now. And so I just obviously, uh, young guy, I'm, it's a, it's a huge career opportunity for me to tell this story, deep dive into S1, deep dive into all the stuff. They just recently gone public and I'm like, Whoa, this company is like solving all the problems that our customers, um, throw at us, right? Like every, every barrier to saying, yes, these, these, these guys have, have, have solved it. And so I did the presentation and so on.

And, and then, um, ironically, like two weeks after I do this presentation, I get a cold call from a headhunter and they're like, Hey, uh, you ever heard of this company Salesforce? We're opening up our first, uh, remote office. We're going to put it in Toronto. Um, is this something you'd be interested in? And I had to be real, I still had to be talked into it, right? I still, uh, Michael Bash, who hired me at Salesforce, amazing leader. Um, Michael, Michael and I, he, he, he and I had probably three, four conversations and I thank you, Michael for continuing to, to, to chase me when I was probably a naive, uh, youngster, but, uh, he got, he, he said, Hey, you've got to, you got to get over here.

And I, I agreed, moved over. And, um, and then I just started to see the cloud happen. Right. So I think that's, that is a bit of a lesson learned in terms of career development is like you should take the call, right? People, people get headhunted. You should take the call. You should do your due diligence. Um, and you should have an open mind when these, these opportunities come by because they could be special companies like that. Um, not all companies are special, but you gotta, you gotta talk to them and see which at-bats, uh, you're willing to take. Well, and that's interesting. So, cause you seem to have a, a, a lens for like, Ooh, good opportunity. And, and I've always said for me, you know, I'm a, I'm definitely an opportunist, right?

I don't, I don't overthink things. I, I usually would two or three pieces of data. I can be like, you know what? That makes sense. Fuck it. Let's go. Right. I had a similar thing with Salesforce where I worked for Basho, right? We were training and you know, 2000, it was, it was 2007, right? When things were, and Salesforce was Salesforce, but they weren't Salesforce. Right. And we had, we had been training Oracle, uh, you know, SAP Gartner, Forrester, like the logo list of Basho was off the charts, but I, you know, and then it went belly up and the, and the, you know, fired everybody. And, and it was me and two other trainers. And I vividly remember sitting in the boardroom with the founder.

Cause I went to the founder and said, what are you going to do all the training? Like, cause he fired everybody and he was just going all in on software. And he's like, I don't know what do you think I should do it? I was like, shit. Uh, uh, what if I started a company and delivered on all that stuff? And then Pedro was like, yes, dude, make it happen. So I was like, holy shit, who's coming with me. Right. And, and I had like, there's two other of the trainers. It was the three of us. And we put all the logos up on the whiteboard and we debated on who was getting what. Right. And they were fighting over SAP and this type of thing. And I pretended like I gave a shit about any of those companies.

I'm like, oh, I've trained SAP. I should, but I only cared about Salesforce because I knew that they were a rocket ship. And even in this economy that was getting murdered at the time, I'm like, there's something, there's something about this company. And I knew if I got them as my key marquee client and over-service them, then the rest of the SaaS industry would be like shooting fish in a barrel. And I just had that at, you know, whatever, 25 years old, that, that lens of that makes sense. What are, what do you think your lens is that helps you make, pick these winners, if you will, um, from, you know, pretty stable, right? Cause there's a risk profile of a lot of people. It's like, why the fuck would you leave Oracle, man?

You only lost a deal or two, like a huge company, big commissions, if you score big, but shit Salesforce. And then you kept picking winners as you went. So is there, do you have a, a specific lens that you look through when you look at opportunities? Yeah. So there's a few things that, that I look at. Um, one is just the, the, the market to opportunity itself. So TAM, right? So if you go into a company that has a large, uh, TAM, lots of selling, um, kind of, um, state, uh, uh, what I would say selling, selling area, right? There's a lot of selling area that you can go after when there's a large TAM. Um, if the company has the ability to expand the TAM as well, so they're getting into more potential selling areas, uh, that that's interesting.

And of course, if, if that TAM is growing, so like chasing the market is, is ultimately the first part of like, where's this market going? Um, like when I joined, uh, Snowflake, the market was moving all of their data into the cloud and that space was, was moving very, very quickly. And, and Snowflake was grabbing onto different parts of the TAM, same thing with Salesforce at the time, right? They were going into service cloud. They were going into marketing cloud and they were growing. So looking at the TAM, I think is really, really important. Um, the next thing you look at is, is really like nice, nice to have versus must have technology. And it's gotta be really, really, really, really nice to have, to make it a must have technology.

But if you really want to find like safety, um, then, then it is finding the must have technology. So like, you can't run a business without a database, somebody's going to buy something. Right. Even when we were at, uh, Salesforce back in the day, CRM still wasn't, wasn't a must have technology, but now it is right. And, and it kind of developed over time. Um, so I think leaning into, to must have technology or at least nice to have technology that has irrefutable ROI is, is a great place to be. Um, another thing I look at too, especially when you look at smaller opportunities, like, uh, like startup opportunities is, do you have a partner ecosystem around you? Do you have a partner, partner, um, army that you can build?

Because there's so many interesting startups. There's so many interesting startups that are building amazing technology, but they're all by themselves and they're telling their story by themselves. They might be going after big market, but I've always found that if you can find companies where you can create ecosystem environments and have a lot of people sing their praises, that's another really good indication. And then after that, it's, it's, it's people, right? I think it's, it's obviously it's people, it's great leaders, it's people that have done this before. And if you see all of this happening, then you check your ego and you take whatever seats available because you're like, I think something's going to happen with this type of company when they have all, all these, uh, kind of green lights and you take, uh, demotions, right?

You take a step, step down in a role just to get yourself in there. I think that's, uh, that's always the right, right play. And then you probably know within 18 to 24 months, if it's worth your time. And if you kind of need to know if it's going to be worth, you need to make a good call and not, uh, you know, have that sunk cost fallacy of making that decision. And if it feels like it's going to be a frog and not a prince, you just, you, you look for the next prince. Yeah. So Ruby was your next prince. I want to get to that. Well, not next, but you had a long journey to get there. But, uh, when, uh, on this arc of your career in the chaos of tech, sass, boom, uh, when did you get married? And then we got to talk about the triplets, man.

Uh, cause that like, I got to figure out where that fits in this arc here of your story. Cause that to me is a curve ball that of all curve balls. Yeah. So I met, I, uh, I met my wife, Alicia in 2004. So we've been on this journey together. We're almost going to cross over into spending more of our life together than, than not. Right. So we're past passing that moment. Um, yeah, so we met in 2004 and, uh, we had our first child in 2009. Um, so still at the boiler room of, of Salesforce at the time. Yeah. And we were going for our second, uh, second child. We're going to have one more. We're going to have one more. And we went to the ultrasound and they were like, uh, yeah, you're, you're, I see one, I see two.

And then a few, a few minutes later, they're like, sorry, we see three. And they said, baby, a baby, B, baby C. And, um, you know, everybody asks, like, is this planned? Like, obviously you don't plan it, but usually what people are trying to say is like, was it IVF? It was not, it was just spontaneous out of nowhere, John. And you don't have triplets in your family. She doesn't have triplets in her family. No, no, no, not at all. No, no multiples, no multiples there. Um, and it's funny. You'll probably like this because, because I know you like music, but, uh, we, you come out of the ultrasound, you're stunned. Obviously you're like, yeah. You're like, everything changes in that second. You're like, every plan you had is just blown up.

Yep. Like our house changes, our car changes. My job probably changes. Like all of this stuff changes. Um, and, um, and we got into the car and we turn on the radio and the first song that's on is tears for fears. Everybody rule. Everybody wants to rule the world. Um, and the first lines in that is welcome to your life. There's no turning back. And we're like, well, that's appropriate. Cause this is like, that's a sign. Yeah. So tears for fears holds a very special moment, uh, in our, in our life. And I tell my triplets this all the time. I'm like, this is when we kind of like, yeah, I know dad. I know, I know. They always hear that song and they know what dad's going to say. So yeah, that was, that was wild.

Like that was, um, that was a huge change. Like it was, it was a dramatic change. It was the most, it was the most challenging thing that I think we've, we've ever dealt with. Our, our, our oldest was only two years older, um, than, uh, than our, than our young, but then the triplets, um, they arrived, it was day nanny, night nanny, weekend nanny. Uh, the funds we were spent spending just to survive, uh, it was survival tactics, right? It was survival tactics. You had, you had to do this and you had to survive also because you have this two-year-old whose life is completely blown apart as well. So it was a ridiculous amount of like resources. And, uh, we ended up, uh, leaving the city and moving out to the suburbs, just have more space, be around our family.

I ended up leaving, uh, Salesforce at the time too, because I found that Salesforce still in 2013 was like a ridiculous boiler room. Um, and it was still like new logo hunting. And I had done it for at that point, close to nine years. And I was like, I need, I need to find a little bit more balance. And so I went to, uh, Microsoft and I ran dynamics for, for Canada. Um, because we had, they just, I mean, they didn't even have an in-office culture. I'm like, this is amazing. I can have a little more flexibility, right? Like it was, it was, uh, it was a move we made at the time. And so, yeah. Yeah. I mean, triplets are like, uh, fight club. It's like a volume for the vault, you know, after fight club, the volume's turned down.

Yeah. That's, that was triplets. And, and also it's like, it's, we, we talk about networking and stuff. Oh my gosh, John, like best net, best networking, uh, drop, mic drop ever. Like you can, you can, you can bond and rapport with everybody when, when you happen to have spontaneous triplets and they are identical to that also blows people's mind. Jesus. Yeah. So, I mean, kudos to you and your partner because, you know, through having that thrown at you, it's just on a personal level though, obviously you guys are stunned. I think I always say that the most important decision you'll ever make in your entire life is, is your significant other, just period. Like it dwarfs in comparison to job, to career, to any of that.

And, and so how did, did you kind of sit down and have a, like, um, come to Jesus meeting and saying, you know, like, Hey, look, okay, this is what we need to do. Like, were you in lockstep with, I'm going to leave sale. I'm going to get more stable. We're going to do this stuff. Or was it just like, Hey, we're, we're trying to survive here. And we're both kind of doing what we're doing. Cause I'm always, I'm always fascinated about the partner side of, you know, of the equation. Cause I know for myself, if I didn't have my wife doing what she was doing, when we had our daughter and taking the sacrifices that she took, there's no way I could have been doing what I was doing. There's no way I'd be where I am right now.

And we did weren't as, as, as deliberate as mapping on a plan. And, and, but we were in line from a value standpoint, from an approach standpoint, and I think we got fortunate. And I just, for those people who are on this journey, I think it's an important piece of the equation to identify of like how you choose your partner, but also how you communicate with your partner as you're going through this chaos. Yeah. Community communication is key. I think I have a very fairly simple, uh, relationship, uh, uh, kind of mantra or, or, or, uh, philosophy. And that's that every relationship can be broken down into common interests and core personality. Right. And I think a lot, I think when you, when you're looking for a partner, that's going to be on the journey with you, it's finding a finding alignment and core personality.

And so I think a lot of people get stuck with common interests, uh, like the same music, movies, sports, right. Like, um, those types of things I think are, are, are very common and be like, Oh, we love hanging out. We love going to nice restaurants. But if, if you have fundamentally different core personalities around say, um, extroversions one, right. So you can be extroverted, but if you're worth a partner that's deeply introverted, you're going to have conflict. You're going to have the, it, it, you can, you can make it work, but it's just going to be a challenge. You, I think a core personality is liking to travel, liking to stay at home, right? Like those are really fundamental things that are going to create a ton of tension in a relationship.

If you can't see eye to eye on that stuff. Um, and then also ambition, right? Like some people, I think, I think, um, what, uh, how my, my wife and I fell in love with each other is we both had a similar upbringing. We both had ambition to chart a new course and accomplish new things that we hadn't been able to experience until getting together. And so, yeah, I think that those things are all super, super important. And then, um, if you're going to be in a relationship with somebody in sales, you're, you're going to have to understand like the, the economic up and downs, the psychological ups and downs. Um, yeah. Like sometimes I think the sky's falling and other times I'm like, everything's great.

And then it'll, the sky will fall again. So your partner has to kind of understand that, that journey. And, and my wife's been great at that. It's been, it's been amazing. Like she's just a, an incredible person and she's a mother of dragons, right? So I can imagine. Yeah. So she's, she's, she's amazing. Yeah. I think that's the one thing that my wife still hasn't really, uh, you know, from a budget standpoint, like when things are good, things are good and we can buy whatever we want. When things are bad, I'm like super cheap. And you know, like that's, that's 50 bucks. We're not going to do that. And she's like, what the hell did they, you know? So I'm like, yeah, I'm looking at my forecast every day.

So right now we're good. Other times we're not. So like that understanding of the mentality of those, uh, she gets it, but we, every once in a while it rears up like, uh, you just, you know, two months ago, you just dropped X on Y and, uh, now we can't go out to dinner and I'm like, yeah, I don't know why you do that to yourself. Um, I, so make a joke in our house. I'm responsible for, for, for debits and she's responsible for credits. And I, I literally, John, I just don't look at, I don't look at the bills. I don't, I, I, my wife, I, I economically trust her. Um, and I find that it's, it just, it's unnecessary noise for me because even if you harp on, um, day to day bills, it's a, it's probably a rounding error at the end of the day, you're really not going to make the biggest difference in the world.

And, and, um, your lifestyle will generally stay where, where it's at. And so if you get into these, the, you just end up inserting like domestic strife over something that really in the long run, isn't going to make a big difference. And so I don't even look at the, I don't even look at the bills. People might think I'm crazy. My friends think I'm crazy, but I trust my wife and, um, I, I know it's almost like it's not worth it. So I just focus on making sure there's enough money to do, you know, the credit side of the equation. So that's why I've always, I've always had the mentality of like, you know, saving money, you know, to your point, like saving a few bucks here or there, I'd rather figure out how to make money so that we can afford whatever it is, as opposed to cut expenses to figure out a way to live the way we want to live.

So, uh, but every once in a while, it kind of rears its ugly head, depending on, you know, again, the business forecast is really for me, what I'm the solo provider. You know what I mean? I'm not the provider. I'm the solo entrepreneur. You know, my, my bank account is the company's bank account. You know what I mean? So I'm looking at like, I'm like, all right, we're doing good. Oh shit. I just lost that contract. So, uh, we got to be a little bit more thoughtful here. So you went, so you've had some great exits, some great companies, you know, started zero, brought it to millions, uh, 2024, you, you started doing some advisory work. So, you know, you kind of had your arc of, of kind of the, especially the tech world.

It's like, all right, cool. You get in grind, you do your thing, get a couple of exits, but an advisor, and that kind of ends up being like, all right, cool. Now I'm an advisor. I get to play around with it. What in the world made you want to jump back into the world of startups now, like with Ruby, right? So you, in the world of AI with as much chaos as there is right now with, with products and solutions, uh, uh, starting executing and dying in months based on what Anthropic or open AI releases, what, what was that lens that you took, right? Cause if you, if you look at stability, if you look at TAM, if you look at all these things that you just mentioned before, that is almost damn near impossible to judge at this point because of how fast things are moving.

So what did you see, first of all, that made you say, I need to do this. And, and what was the kind of lens that you used to then do it? Right. Yeah. So, so I think the, the, the first thing was I, I spent a lot of time with entrepreneurs and, uh, working with, uh, companies that are moving from founder led sales to, to, to building their first sales organizations. And that was one kind of experience of kind of seeing where that, that, that market was at. Um, the other thing too, is, um, uh, business partner of mine, who's also a co-founder of Ruby. We started snow angels, which is a snowflake, uh, investor syndicate. So we, we, we, we, we, and a pool of, um, snowflake alumni, we invest in data and AI startups, uh, primarily obviously AI startups.

And so seeing what these companies are building and what they're doing and all the opportunities that exist, it's fascinating. And I, and I do believe we're still very much in the early innings of this whole journey. Yep. Um, so started to think about, uh, potential AI use cases and, uh, the combination of, of kind of working with these AI entrepreneurs, but then also working with, um, the SMBs and kind of mid-market companies I was advising, I was starting to realize that, that AI was too hard for the sales reps. It was too hard. And, and, and what I mean by that is, uh, there was very little way and there still is very little way for, um, the average sales person in a small company and a large company and so on to have AI help them through the entire sales cycle, right?

AI just, it doesn't have the context. It doesn't have the memory. You have to generate all the action yourself. You have to know how to prompt it. You have to organize all your thoughts in, in chat and try to figure it out. And, and it just reminds me of, you know, back in, in the Salesforce days where CRM was unusable for a sales rep. It was unusable, right? Siebel, uh, Goldmine Act. It was unusable. It was like crappy information, uh, no good insights, no good outputs. Um, from a sales leader perspective, it was a black box. And so, so Salesforce made this, made this decision to make a highly usable application that then became widely adopted. And I think that most of the AI applications today in sales, just, they don't have that usability.

They don't have that complete, uh, works like a sales rep, uh, kind of, kind of world. And they also require a lot of, uh, you know, and set up and so on to, to use it. So I just felt like there was an easier way to take the power of AI and, and, and put it in the hands of, of salespeople. Um, but I gotta say, like, before talking about all of Ruby, we have to talk about like the imperative of AI, right? The imperative of AI for, for sales. Yeah. For salespeople today. Like what I think a lot of people don't fully appreciate is, is that your competitor is often your buyer's AI. Yeah. Right. Think about that for a second. So you are competing to win the hearts and minds of your buyer's AI, because what, what's happening is, and again, like I, I'm, I'm, I'm certain people don't fully appreciate this, but imagine a scenario where, where your buyer, uh, even before you, they, they decide to take a call from you, they're checking in with quad.

I'm like, oh, quad. Should I, should I talk to John? I don't know. Quad is going and searching the internet for every little piece of, of information on John. And it also knows everything that you need to know, right? So it, or about your business. So it already has an appreciation for what the buyer's doing and it's making the decision on behalf of the buyer. And there's, there's, there's cognitive offload. You can call it cognitive offloading, cognitive surrender. The, the buyer is, is deferring to the, the AI, um, on the, on these decisions. And we have a customer at, at Ruby, amazing, amazing tech company, um, doing some pretty, pretty incredible things in, uh, in, in billing and configuration.

And they've sold to, uh, both open AI and Anthropic. And in both cases, both companies said, just send me all your documentation, right? Just send it to me, send me all your documentation. Tell me what you think you can do for us. And we're going to feed our LLMs and we're going to let them have their opinion. So this is what's happening today. And I think there's, there's two problems with that. One is, um, you have to make sure what you're putting to the customer is, is impactful and highly personalized. And then the other problem with this is, is you have to earn the right to stay in the room and be in the conversation. Because if, if, if the buyer's AI is answering a lot of their questions on behalf of you, then why would they talk to you?

Right? That I can't wrap my head around that. And that's like, you and I are on the same page with this, this, the five alarm fire that I think we're looking at right now, because everybody's looking at these AI tools that are replacing sales reps and they're automating the sales, you know, parts of the sales process. And no, we're not going to need BDRs. I don't give a fuck about any of that stuff, man. I care about when the client wakes up and realizes exactly what you just said, that I don't need you because most sales reps. And I, and I say this because I see it and I think that we have turned, I did a presentation at Pavilion a few, a few months back called anything but predictable. And it was basically how the predictable, I feel like the predictable revenue model.

And by the way, I'm the biggest offender here. Like I've made a ton of money on the, on the predictable revenue model. I've trained the entire model, but I, I fundamentally think it broke sales because the segmentation of roles turned it into a, an assembly line. And we taught these kids way more on process, way more on tech, and we didn't teach them how to sell. We didn't teach them hand-to-hand combat, going out, knocking on doors, those types of things, that skill, at least in SaaS and tech is gone. And, and so we turned them into these robots and now they're getting replaced by robots on the sales side of the house. But when the client wakes up, man, and because all I look at is sales rep is friction.

And, and I look at myself, you know, people are like, oh, well, no, John. People are always going to want to, yeah. If there's value, right. If there's value in that conversation, but they're like, oh, the best sales reps ask questions that the client, that, that the client hasn't even thought of. Oh, really? Hey, Claude, could you act as the best fucking sales rep and ask me the questions that I'm not even thinking of right now? So, so with that, how does a rep outside of the legacy buyers who aren't there yet in that scenario, the fuck does a sales rep do? Yeah. So you, you, you have to arm yourself with AI first, right? You, it's a, it's an arms race. So you've got to have the same kind of, uh, uh, advantage and intelligence advantage that your buyer has.

And so you need to know as much about their business as they know about yours, right? You have to find gems. You have to find insights that they, that they may not know about their own business. And you have to do it all the time, all the time. I'm not talking about like, Hey, up front, we figured out these things and we go for it. It's like, you have to do it all the time. You have to be, uh, at every meeting, having hyper-personalized discussions about their business, hyper-personalized, um, at every, in every interaction, every, uh, uh, email you send focused on you, focused on you. Right. You should be able to be prolific with personalized ROIs, personalized proposals, personalized POCs that are based in the reality of your customer.

And you should, you need to be prolific with that all the time. Right. Like it, it, it, I struggle to understand, uh, a world or see a world where a customer is going to want to look at a data sheet unless it's about them. Right. So we have the technology now to consistently issue a data sheet to a customer that's about them, not just about us. And, and again, you go back to the situation where these customers are going to go and they're going to put it into a, uh, an AI and the AI is going to make the decision. And so what an AI does, and again, this is something that, that the industry is still learning and appreciating is the, the AI has its own cognitive surrender. So what I mean by that is an AI actually loves to be given the answer.

Right. And so this is why AIs will go and recommend things that are, somebody has written up on like that the top 10 ways to do this or the top 10, uh, solutions that do this, or I've compared this solution to this solution. This one wins. The AI is like, cool. I agree with that. And so what, what people need to do is they actually need to give AI the answer. So what, what a buyer is doing is saying, Hey, is this good for my business? And if you give them the evidence, give the AI the evidence that this is conclusively what we understand about your business, why it's good for it, that AI is going to recommend you. And so if you're, if you're a vendor and you're up against a competitor and that competitor is giving generic information to the buyer AI, and you're giving specific hyper-personalized information, that AI is going to be like, cool, you figured it out for me.

I agree with you. Let's go with you. Right. That's, that's, that's the thing that people don't fully appreciate. So we're going AIs to AIs here. Right. And that's why I'd like, that's one of the things I'm seeing, even with me, quite frankly, like, you know, I'm giving these kids, you know, I train in Salesforce and I'm like giving them a prompt to do some prospecting. And I tell them like, use it to get close and then do your thing. And then they send it over to me and I put it into my AI bot. And I say, review this and give them feedback on it. And I give it back to them, you know, and that's a basic, you know, I, that's fine. Right. With some context there. Okay. But help me understand how Ruby or any tool out there gives great Intel.

Okay. You and I, I forget, I don't know how I'm 50, right? We have the scars, we have the context, we have the business acumen to be able to call bullshit on a AI when we see it, to use the information and articulate that the right way in a conversation. How does the 25 year old kid who didn't go to a co-op, who is really just trying to figure out business and make their cold calls these days, how do they use it to build their business acumen, not just have it, have the answer for them that they then poured over to somebody else's. You know what I mean? Like that's, that's where I'm, I'm nervous. It's, it's not for the guys like you and I, I think the guys like you and I, who've got 20, 30 years in our, in our back pocket, and we know when to call bullshit and we know how to have conversations without scripts.

We know how to engage with people and ask like thoughtful questions, get people to think. I'm not worried. I think it's a superpower for us, super fucking power, but it's like these, these kids, like because they've all been kind of shortcutted, like, Hey, here's the answer. Here's the answer. And it's like, Oh, great. There's the answer. Good. Go. Where do they, how do they use AI for the business acumen so they can even have the conversation at that level with all this insane information that AI can present to them? Yeah. It's a, it's, it's, it's a, there's a, there's a lot there that you have to work through. I think, I think the, the first thing that I would recommend anybody does is that they're going to get an AI output, right?

They'll get an AI output. It'll be their, it'll be their research. It'll be the recommendations of the AI. And then at that point, you're going to want to do something, right? Take those insights into some sort of action. You're going to want to, uh, plan a meeting. You'll want to create a meeting deck. Uh, you'll want to create an ROI, et cetera. And so the best way that you can actually use AI then at that point is to tell the AI what you're going to do and what you want to do. Right. And so there's this aspect, there's this thing called, uh, like, like transfer memory. So you can learn more. You learn yourself more when you explain something to somebody else. Yes. Right. And there was this thing, uh, uh, I read about recently.

It was like the, the, the rubber duck, uh, the rubber duck, uh, coding or something, a rubber duck exercise where coders, what coders would do is they would explain their code to a rubber duck, like literally, literally John, a rubber duck sitting on their desk. They'd be like, this is why, this is how I did my code. I did this. I did this. I did this. This is what I was thinking. And just the art of explaining what they want to do to something, uh, really, really dug it in and really gave them a lot more insights about what they're going to do. And I think the best way you can use AI in that scenario is to say, Hey, you know what? I did all this information. Here's the meeting I'm going to run.

I'm thinking about doing this. I'm thinking about doing this. I want to ask these questions. I'll do this. Um, what do you think? Do you have any feedback for me? Um, anything I'm missing. Right. And so now you're, you're learning it. You're giving it to somebody that who's, who's listening to it. And then they're coaching you. And that's, that's the piece that I think that, that we have this amazing ability to do is like you, you need to have an interaction with, with your, with your AI and try to figure out a way to have it start to coach you and give you that, that thinking partner that's going to make you really, really successful. If it's, um, you know, uh, uh, kind of like one-sided thing where I'm just going to take from the AI and then I'm going to spit it out without actually interacting with it.

It's, it's, it's pretty challenging. Now I'll say there are some amazing technologies happening around like role play and coaching, um, out there today. They're still pretty generic, right? They, they, they actually aren't coaching you on that meeting or coaching you on that deal. They're coaching you on like philosophically how to compete with Databricks if you're at Snowflake, right? And so I think those, those tools, as those develop, then that, that forced curiosity, that, that interactive learning, um, the, the thinking partner, right? I think that stuff will become more, more regimented for sure. So let's get into Ruby now for context. Let's, let's understand what Ruby does. Uh, so, and then I got some questions about the, the challenge I see right now a lot, which is the, the, Hey, uh, I can build it in Claude.

Why the fuck would I buy this? You know what I mean? Cause there's the idiots like me who are using like replet and lovable to build these fucking apps when I can vibe code it. And it looks pretty bad-ass. I don't know anything in the backend of security or any of that shit, but man, I built, I just built this kick-ass app. So, uh, that looks fine. Why can't I just go? So first of all, give us some context of what Ruby is. Uh, and then talk to me about how you're dealing with that specific objection to people right now. Cause I think everybody is going to be dealing with that objection. And I know everybody is right now, which is why can't I just build that, which is back in my day when I was selling it services at the infrastructure level, I faced something similar.

Cause we would go into companies that had software engineers and the engineer, the software engineers, we like, we can manage our servers and work, you know, like why the fuck, like, why would we hire you to do this? So I'm like, yeah, but that's not what you get paid for. Like it was a little bit of an easier talk track because it was a technical person that I was like, you really want to deal with a boring infrastructure shit when you're creating software that's going to make your company millions. But now you have every moron like me in a company saying, look at this, hey boss, why would you buy that? I just created a custom GPT for us to go do the, you know, extract some information. So with that as context, help us understand what Ruby is so that people have that.

And then how are you combating that objection specifically in the market right now? Yeah. Like, um, I think everybody's going to deal with that objection. Like no matter what you're selling today, the LLMs are coming for you. So it's sales AI, marketing AI, uh, uh, CRM, what have you, everyone is going to, to, to need to, uh, compete against those, those solutions. Um, but, uh, but yeah, but about Ruby, uh, the problem we're looking to solve is really ensuring it it's ensuring a sales rep can be excellent in every moment of a customer interaction. And so that, that, that's been the traditional problem in sales is like, you can't necessarily win every single customer interaction because you have too many accounts, right?

You, you, you don't have the ability, a sales rep generally does not have the ability to exceptionally manage and exceptionally run dozens of deals across dozens of accounts. They, they probably just joined the company and are learning the account. They just, if you're at Salesforce, you've just, you've just received a hundred new accounts for, for the, the annual account shift. You've got new products that have come out, um, and your customer's changing over time. And then within your customer, you got the five to seven stakeholders you have to appeal to. And so all of this information is, is available to a sales rep, but you're unable to synthesize it and execute on it consistently, right?

You just, you just can't, you'd have to have this, this unlimited brain power, unlimited, uh, storage, uh, and automation to truly be able to do that. And so this is where, uh, we feel that Ruby is, is down, going down the right path. So what we're trying to do is we're trying to create something that has full context. That is, that is essentially zero calorie effort from a sales rep. So what I mean by that is we're, we're perpetually updating information about your company. We're perpetually updating information about, uh, your customer, right? Creating organizational memory and customer memory. And a lot of the solutions out there that they don't have that today. Like, uh, if you look at some of the, the conversation intelligence solutions that are out there, they might be able to give you information about what happened at the meeting, but they really don't tie in any information about like how you sell or how that company buys or, or any of those nuances of, and rounding out the picture.

They can just say, Hey, this is the problem I heard on the call. I think that's it. But what, what a great AI would do is like, Hey, this is the problem that, that I just heard on that call. Um, this person mentioned that problem in the last call. I think that this champion might be able to help that person with that. Here's why it matters in this, this organization. Here's the customer story. You should tell them here's the ROI that you should tell them all of that context is what AI should do. And today AI doesn't operate with that degree of, of intelligence. And so I think the first thing that we do is we gather the context, right? The, the organizational context, the, the, the customer context, the meeting context, we bring that all in automated.

It's there, right? It's generating, it's sitting, it's sitting and available for use. Um, then we automate all the AI after that. And so the second problem with, with AI, if you get past building all the context and feeding the beast with context, the second thing is it's user operated. So you have to know what to ask. You know, you need to know what you should do next. You need to basically, uh, drive, drive the engine yourself. And really AI should know what you need to do next, right? AI should have some insights and be like, Hey, this happened, this happened, this happened. Now I think you should maybe do this, maybe do this. And so what we also do is we automate the actions throughout the deal cycle.

So we, we basically activate all those agents and, and all that underlying prompting on your behalf so that it's, it's there proactively assisting you as opposed to you having to go and call and respond, uh, to it. And then the last thing that we think about a lot is just those outcomes and delivering those outcomes. So delivering those ROI materials, the ABM materials, the follow-ups, all of that stuff grounded on the reality of those two prior steps, right? Grounded on the reality of full context, grounded on the reality of, of all of these agents working together to come up with McKinsey level insights that are ready all the time, that are there ready to go and, and I think, um, the, I guess that the last thing too, I would say is it's also organized the way that you work.

And so I just have this fundamental belief that the chat interface will not, uh, exploit the true benefits of AI for the average sales rep. So there's, there's, there's 700,000 salespeople in B2B technology in North America, 700,000. Okay. You cannot tell me that 700,000 sales reps are going to use replet, are going to use cloud code, going to use a chat interface and accomplish all the things that we've been discussing on this call. It's not going to happen. It's not going to happen. And so fundamentally there, there has to be something easier for sales reps. And one thing that we also focus on with, with Ruby is that you can go use it on your own. So this whole thing is designed to be low friction, right?

In a, in a life of selling, I try to build things and I've wanted to sell things that are low friction for somebody to buy. Anybody can go to the website, HeyRuby.ai, and you can basically run, run accounts out of the gate. So all of that context building, all of that is done on your behalf and a sales leader can go buy it for their sales team or a sales rep can go and use it for themselves. We have companies that have just logged onto the website and they sell environmental remediation. Great, right? We have companies that have, that have gone on the website and they, they sell event space for corporate events and they're using it, right? And that's what AI should do. AI should be able to go and figure out all this context for you, activate the insights, activate the outcomes, and just kind of guide you along the way.

And it's a novel approach. And yes, as we, as we go through and we, we, we did a round of fundraising, had to answer a lot of VC questions about, about Claude. And I think that it, it just is, has that fundamental usability gap that I am certain. And having seen this through the whole, you know, world of, of CRM and it was at Gong as an advisor in 2017. Like I've seen all these adoption challenges that are coming up and people I think they, AI just needs to be easier. And so you look at what's out there today and you look at Claude and I love what Claude's doing. And it's, I use it every day and it underpins a lot of what we're building at Ruby, but you've got to have the sales workflow layer and that experience built on top of it because it in itself is like using Claude instead of something that's purpose-built for, for sales is like saying, Hey, I could just build my CRM on Oracle.

You can, you absolutely can build your CRM on Oracle and you can build that yourself and manage that yourself in your organization and it deal with all the change management, all that stuff yourself and be locked into that database. Or you can buy something purpose-built like CRM that, that, or Salesforce that somebody else takes care of. Right. And then that's the other, that's the other thing is I think we're headed down this, this fallacy of, of, of build versus buy. Like we're suddenly going to build everything and manage it all ourselves and, and deal with all the bullshit that we've been trying to get away from, from cloud. And now we're saying, Oh, well, actually I could just build it all myself.

Well, what happens when the person builds it that leaves, right? What happens when you've built it all on Claude and you know, you deal with an odd decision federally that puts your LLM provider in jeopardy, right? Like you have to have portability at these AI solutions as well. So, or what happens when Claude, if Claude goes public and all of a sudden needs to actually have like, and raises their token rate by, you know, a hundred percent. And all of a sudden you're paying a million dollars to run whatever you just built. Like that's a real, they got to make money, right? Yeah, exactly. Exactly. And I, I believe that there's, there's a world where people lean on providers like Ruby to actually token max and actually say, Hey, like, I'm going to run, I'm going to run efficient tokens for you so that you don't blow up your budget and have everybody on, on, uh, you know, Claude max running 400 bucks a month.

Like I think that there is, there is the responsibility of, of providers like Ruby to be able to help people with those types of efficiencies. Absolutely. Yeah. So, so you don't think that there is a world where, cause you know, if I leap very far into the future, not well at this point, who knows? Um, but each one of us having a personal assistant, basically, whether it's our iPhone or the chip in our head that allows us to just be like, Hey, uh, I, I got a meeting coming up with Chris here. Uh, do me a favor, go look through all this stuff, you know, and tell me what I need to know about this business and, you know, put it into a little podcast for me on notebook LM and, you know, let me listen to it before I have this conversation.

I'm ready. You don't think we're in the world where it's going to be a, basically whatever I want is a vibe code as opposed to the, the execution layer of a specific skillset. Yeah. I think you're going to have to, you're going to have to have the execution layer, especially something as, as intellectually complex as, as sales. Like there's a lot of things that need to be figured out. There's a lot of layer layers of understanding that need to be figured out. And especially your, your, the, the jobs change over time too, right? So it's like sales for healthcare, sales for med device, sales for, for, for pharma, like all of those things have their own inputs, their own data sets. They have their own, uh, workflows and language and all of those things are, are going to be specific to that.

And so could an individual vibe code it maybe could a company vibe code it maybe, but I really believe that they're going to defer a lot of that provided the economics are sound. They're going to defer a lot of that to experts in that domain to be able to execute that, right? Like domain expertise is so critical. If you say, Hey, I'm going to vibe code it. So, okay. So how do you establish domain expertise to, to vibe code it? Are you the domain expertise? I know this is your business, but are you the domain expertise? Should you be building it this way, are you going to continue to innovate quickly on this as, as things evolve over time? Like we see the pace of innovation of what's available through Claude and the LLMs.

Are you the company to distill that innovation down into these vibe coded applications as quickly as your competitor is, right? Like, I just don't see that. I don't see companies being able to, to keep up in this, this like age of acceleration. So I think that, I think that these guys all become marketplaces, right? Like I think that, you know, Salesforce went to app exchange, like snowflake has their data marketplace. I think there's going to be purpose-built applications available to be inserted into the quad experience with the open AI experience. They've already moved in that direction and people will be buying modules, app store type modules, and they're not going to be building everything themselves.

I think it's just, it's, it's, it's too difficult for a thousand different reasons. What does AI do to sales methodologies? And the context of that is, you know, a lot of people choose like a medic and, you know, Miller Hyman, because they got their approach and I've never been a methodology guy. I just, I love tactics, structure tips, you know, agility, right? But there's these quote unquote methodologies and, and one's not better than the other. It's all about how, so does AI effectively, even the playing field when it comes to quote unquote methodologies, because most of these tools, right? These platforms, whatever it is that you can put every methodology in there and then figure out, you know, the best components of all of it.

So it's, so it's your custom approach to selling versus, you know, off the shelf type of thing. So, you know, random question, I think, but what do you think AI is now going to do to sales methodologies and how they're implemented? Well, I think, I think, I think one, you just said it right, is like there's methodologies are, are, are like too broad and too vanilla in many cases. And so there could be more bespoke methodologies for particular industries. But I think what AI does and, you know, something like, like Ruby, for example, is that if it, it levels the playing field to, for any company to execute, like they have a massive sales and they have one team. Yeah. And so like, even if you, you walk into an organization, you're like, Hey, I want, I'm a, I'm a sales leader at a series A company.

I got a team of six and now I come in and I want to deploy MedPick, right? That's great. Congratulations. That's wonderful. Now you've got to figure out how to train everybody in MedPick, but then stay on every single deal to make sure that MedPick is truly executed. And it takes a lot of effort to do that, right? It takes a lot of management, it takes ongoing monitoring of things and what something like, like Ruby does and potentially other AIs is it helps you drive that kind of change as if you had a full time sales engagement person doing that on every single deal and every single account. And so I think for sales methodologies, they probably become more, more bespoke, but they become more consistently applied because AI is helping to monitor that more consistently.

That's, that's what I think. And, and yeah, I think your, your take on it is, is right, which is, it's probably going to be amalgamation of all the best stuff, right? Like personally, I like MedPick, but MedPick doesn't gather any great information without Sandler, right? MedPick is, is kind of like the lagging information and, and Sandler is the leading information that you have to get. So you do need both for sure. Yeah. And then, you know, the gap selling and then the challenger set, you know what I mean? And they're all applicable at different components and they can pull in like for, I could, I could envision like, you know, John, in this scenario, based on who you're about to meet with in this, like you have to actually pull the challenger sale on this one.

Cause that's like, that guy's a high D over there. And if you don't punch him right in the fucking mouth with your opinion of something, you there, there's no way you're going to do it. So I can see this actually being great for organizations who can finally customize their own process as opposed to trying to, you know, rely on one methodology to, to run their org, which it's funny. You say that like with, with Ruby, we, we create discovery questions and objection handling as as per Sandler, because I'm a big Sandler fan, love, love Guru Ganesh, I've seen him many, many times. I just talked to him just the other day. Yeah. I brought him into many companies. Yeah. He's amazing. I think he's a great, it's a great, it's a great point.

Yeah. Thanks. Thanks for that. There's a lot of questions. I think I've seen it all right. I think I've seen every single sales training and I've cherry picked what I think works best during different parts of the sales cycle. So yeah, it's a great, it's a great point. Thanks for very inspiring positioning for, for Ruby. There you go, man. And I think that's the best case scenario. Cause you know, that's why I've always been like, when people ask me like, well, what, you know, we're looking for a methodology. I'm like, really? Are you, do you mean like a soup to nuts, you know, top down, everything integrated from one vendor? I'm like, you're out of your fucking mind. You know what I mean? Like you should take the best of this, the best of that, the best of this, and put it all together and make it yours.

Cause no one sales training vendor has the answer to every single problem that you're going to try to face here. So yeah, completely love it. Awesome, man. Well, we got to tie this one up. So where can people find out more information about Ruby, about what you're doing and all the above? Yeah, thanks. Thanks, John. HeyRuby.ai is the website. You can go on there. You can check it out. You can try it, right? Which is, which is a nice thing. Just sign up and put one of your favorite accounts in there and let's see what kind of gems we can find. And feel free to follow me on LinkedIn. I'm happy to connect, happy to have conversations on this and then I'll be at Sastr as well. So, um, I don't know if this, we're going to, we're going to put this out there before Sastr or not, but that's something people can probably love to meet in person.

Awesome. Awesome. Thanks, my friend. It was a great conversation as usual and, uh, yeah, appreciate you coming on. Awesome. Thanks, John. Appreciate it too. Have a great day. You too, everybody. Thank you. And thanks for listening. And as I always say, uh, go out there and make somebody smile today because no matter how bad your day is going or how bad you think it went, you make somebody smile today. You know, you had a good day and the world needs a lot more of that right now. So thank you all very much. And I will see you on the other side. Hey, thanks again for listening to the show and for all your support throughout the years. This is one last reminder to check out my training programs at jbarrows.com or leave a five-star review on your favorite podcast platform or G2 if you've already gone through my training or sign up for my newsletter.

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