Jared Cook - A Rebel Story of a CS Leader Scaling a Side Hustle with AI

Speaker A: Foreign. Rebels. We are back in the studio today yet again, and we're excited to have Jared Cook here with us. So welcome. Jared. I'm so glad that you're here to share all things entrepreneurship, you know, the power of the side hustle.

Speaker B: Thanks for having me on the show. I'm excited to be here.

Speaker A: Yeah. You know, when we first started talking to people, it's been three seasons ago now. Professionals like you that are, you know, doing all the things. One of the things that I think is important is to really sit back and think about the human element of this. And I was curious if you would share with us, you know, what. What brought you to where you are. I mean, you led a massive customer experience team. You've done adjunct professorship, which I did too, by the way. I taught a little bit of college, so I'm just really curious. And then you spent some time living, like, actually living in South America, right?

Speaker B: Yeah, yeah, no, I, uh. Excited to share a little bit about the story that kind of brought me here. I've spent the better part of 25 years in SaaS, mostly at large organizations. Adobe, Domo, Docebo, all of these were either large organizations or became large organizations as they grew through ipo. And in each one of those, I spent time in different roles, from product and strategy to business development, the customer success, and education and professional services. So, uh, I've really been fortunate to spend time at different parts of the organization. And where I say that I found my home was in customer success and finding people who are really wired in the same way that I am. And so that's what's kind of led me to where I am now, launching my own practice crush, Churn Consulting. It's all about helping tech companies improve customer retention.

Speaker A: Yeah. You know, and I will say, as a human, both in the content that you share, because I love your shares on LinkedIn, by the way, but in the work that you do. And just knowing you as a human, the little I've got to know you so far. I love to hear you talk about problem solving, and I think that's so important in customer success. I mean, do you think that's the thing that draws you most to it, as opposed to the other areas of the org that you've been intimately aware of and worked within?

Speaker B: Yeah, I think to a large degree it is. You know, if there's problems, I, uh, like chaos. I'm drunk. But I don't like living in it, if that makes sense. I like to find it and then clean it up and so that's what really draws me to customer success. And I tend to bring a lot of kind of technology and my background. I've started my career as a software developer. And here's Cosmo. He's just climbing up.

Speaker A: Hey Cosmo. He's now so, uh, cool. Hey Cosmo. Best ever.

Speaker B: So, uh, it is problem solving really at the heart and, and human connection. Like I value this kind of thing, Anna. To be able to connect with people, to just be real about the life that we're living and why we do what we do. I don't know what your big why is, but for me it's about family and it's about creating freedom in life. Um, and so, you know, the, the more ways that I can do that, and that's, that's part of why I do the side hustle that I do, that's why, you know, I'm doing my own consulting practice right now, is to, to be able to um, fuel that freedom and, and the ability to have a, uh, what I call a free life.

Speaker A: Yeah. And that's, I mean it's massive because I mean in a world where we're always trying to figure out like how do we build AI, uh, driven models, vibe coding, all the fun things, predictive health models, forecasting, all the things that I'm sure that you work with your clients to be able to deploy and make work. You know, the thing is that at the end of the day there's so much to be said just about human interaction and I just think it's really valuable and to be able to have a conversation and say, oh yeah, well I traveled there or you know, that was cool, I ate there. And that's some good, you know, that's a good vibe. I like that place, you know, that kind of thing. And to be able to share that experience, even if it's at a distance, you know, I think it's, it's really important to customers that buy anything really, but especially customers in a, like a subscription kind of based model. I'm interested to see what that's going to look like as we continue to evolve too, if we're going to stick with seat based pricing or if there's going to be continued evolution toward kind, um, of more of a consumption usage base, uh, with a pricing model. So I'm very excited to see how that's going to trend.

Speaker B: Yeah, yeah, there's, there's a lot of shaking up right now in the world of SaaS, isn't there?

Speaker A: Yes, absolutely. Uh, kind of apropro that you would bring that in, Bring that in right there with the noise. Jared. So you mentioned side Hustle and I think that that's so important because whether you have a job, right, because so many people obviously are living and working inside of tech or if you're looking for one, you can probably say, at least to some extent, with AI kind of looming, we all want to embrace it, we're all learning and evolving with it. But um, at the same time we all want to figure out how to adapt to live that free life the best that we can. And so making ourselves from a portfolio perspective, uh, as rich, so to speak, as possible. Um, to be able to do that and to be able to experiment a little bit as needed, adapt and flex, have value above and beyond our day job. It's important. You know, I first started following your content because of your thought leadership around cs and I just thought that some of the things that you did inside of your client base from a consultative perspective was um, you know, really helpful and things that I thought I could apply and utilize. So, um, and then I started seeing these cool shares that you were doing on your side Hustle, which I'm not going to steal the thunder, I want you to tell us about that. But I mean we all need something to kind of fall back on or to supplement. So tell us kind of how you ended up doing what you're doing from a side perspective and a little bit about it.

Speaker B: Yeah, yeah. I think it's probably important to just start by saying, you know, just like in investments, you want to diversify. Look at my income streams is the same way I want to have income streams that are diversified, they come from multiple places. So if one turns off, there's still others that are flowing. So that, that's kind of the why behind what I'm doing. And then the second thing, and I'll tell you a little bit about the TURO business that I've started. It it's really. I'm not interested in getting another job. My goal is time, freedom and m. So you know, uh, really as I started to look at side hustles, I was thinking what are, what are things that I could do that might take an initial investment in time and resource and, but eventually can be much more self sufficient, much more passive. I don't believe in a hundred percent passive anything including uh, income. But I do believe there's a way to build a system and a machine that can generate income with little input. And that's what, that's what I was interested in doing. And so I kind of stumbled on Turo. To be honest, if you're not familiar with Turo, it's Airbnb for car rentals. You've got a car that's sitting around, there's people that want to rent it. Cool. And that's. That was the situation we ran last year. I had a car that was sitting in the garage, very underutilized. I work at home, you know, and so I said, great, let's just throw it out there and see what it'll do. And, uh, and it made me a thousand bucks in the first month. And I was like, oh, that's kind of interesting. That was kind of low work. I had to wash the car and take it up to the airport. So the second month I got. I bought a second car and I put it out there and it did the same thing. And I thought, wow, that's pretty interesting. Then I, uh, then I started going into spreadsheets and thinking about, what if I had five cars? What if I had 10 cars? What if I had. This is crazy. What if I had a hundred cars? Like, what would that look like? And I started to think, wow, uh, that, that could be a pretty interesting flow of, of income. But I was starting to notice, like, it was not sustainable. When I got to two cars and then three cars. I got up to five cars by October. And I was thinking, all I'm doing is washing cars and driving cars to the airport. And like, this is not sustainable. And so then it started this problem solving got.

Speaker A: Yeah, that. The back to the customer success and the problem solving, right? Yeah, yeah, yeah.

Speaker B: And so I thought, how could I build this in a way that doesn't require me? And so I started looking at AI and I stumbled on a tool called Base44. If you haven't used it, it helps you build custom apps, uh, using AI. And I went to work and I built out an app that does a lot of the things that I was doing manually. Now, I can't drive your car and it can't drop it off, but what it can do is coordinate other people's schedules. It can coordinate notifications, you know, it can track expenses, it can connect to QuickBooks, all these kinds of things. And so I was like, huh, okay. So I built out this automation app and then I went and hired three drivers, all of them as 1099 contractors. I only pay them for the time that they. They're actually working for me. And now they're doing all the pickups, the drop offs, the cleaning, the maintenance and, uh, and I'm managing it right from here from my desk. And so I've gone from one car to ten cars. Uh, we got ten cars running on the platform now. My goal is to get to 15, um, in the next 45 days. And, uh, you know, it's, it's, it's scaling, it's working.

Speaker A: That is awesome. Yeah. So I love a lot of, kind of what I'm hearing inside of that. The thing that I love the most about it is that you saw and had to adjust very quickly from what you had sort of deduced from different, you know, really different signs and signals. Hey, this isn't working. We need to figure out how to adjust and also potentially to retool, to be able to help to solve for basically the op, basically to operationalize. And looking at that and, you know, I'm curious, what is the thing that you look for that says, hey, I need to go get another car? What. What had kind of indicator did you look for that really showed you that from evidence standpoint, or did you just kind of say, hey, I want to go see. I'm doing a beta test anyway, I want to go see. Is that really what it was?

Speaker B: That's the mindset. Uh, my mindset's always like, hey, we're going to test this thing out. Which, which puts you in a mindset of flexibility. You can dial it up, you can dial it down. Right. And so I use that often in any business situation is like, that's all we're doing anyway. We're all just testing our way to the best optimal solution. But are you ever going to arrive at it and you're going to high five and say, great, we never have to work anymore? No, it's going to be constantly adjusting and adapting. So that's the mindset. But in terms of atturo, uh, really what helps me identify am I ready for another car? Is I'm tracking all the metrics just maniacally every single day. I track every expense, I track every income, every source of. Where did we find this guest? How long did they stay? What's the dollar per. Per mile that I earn on it? You know, and so, uh, all of this built inside this custom app so I can track all my metrics. And then with those metrics, what I can see is my margin. The end of every month, I say, what was the profit margin Right now, you know, if I get a dollar in, in rental income, I'm keeping 70 to 80 cents of that. Like, that's pretty good margin. And the, the other 20 to 30 cents, they're going to my drivers, they're going to maintenance people, they're going to refueling insurance claims had a couple of those. So. But even then operating it really well. And as I see those strong margins, I say, great. The business and the system is working now. We can continue to scale.

Speaker A: Yes. So beta test model and then just basically sort of triangulating that and progressing steps sort of at a intermittent pace. Uh, you know, but in a way that is very calculated. So it seems. And do you track like. I'm guessing. So I'm all into the whole. You mentioned Airbnb. I'm actually going to London. So I had, I booked an Airbnb. It was very interesting. They sent me a customer satisfaction survey, of course, like all the surveys that we do and success. Uh, I'm curious where you sit on customer satisfaction data and surveys and that whole process, do you find it useful as an indicator or do you think it's kind of overhyped? Like, how do you feel as far as voice of the customer, some of those NPS that flavor, See?

Speaker B: Yeah. Look, anytime you can listen to your customer, it's a good thing, but make sure that you're listening to your customer and you don't have this hidden agenda to get a high number.

Speaker A: So true.

Speaker B: You know what I mean? Like so many people, you get caught in the trap of, yes, we're going to track nps. And by the way, we're only going to ask happy customers when they're very happy, if they're going to, if they're going to survey us. Okay, we kind of missed the point because now we're trying to gain the number. Why? So that I can pat myself on the back and look good? No, like, if your intent is, let's listen to customers, then let's listen to them. Let's see what they say. The good, the bad, the ugly. Great. Now that we hear it, how are we going to synthesize that into trends so that we're not firefighting every single response. But you're, you're, you're sitting back, you're observing, you're listening. Okay, I'm seeing this consistent theme, this trend. All right. I saw this at Docebo when we were there. You know, at nps, what we saw was consistently there was this theme around a part of the product in integration of data that just kept popping up. And it was like, okay, you know, this isn't a one off, so what do you do with that? Now that you can see the Data and the trend. Then you go and you take that to the product team and you say, hey, listen, this is, this is not a one off. Here's. We're quantifying it. We're this many customers, this much ARR is at risk. And now it's a, it's not a, you know, emotionally charged kind of conversation with the head of product. It's driven, it's fact driven. And then we make a decision as a business. Is this something that's worth investing in?

Speaker A: Yes.

Speaker B: So I'm a big believer in mps, I'm a big believer in csac. As long as there's no hidden agenda. As long as really listening.

Speaker A: No, I love that and I love hearing that from somebody who has so much experience from a breadth perspective across the SAS organization, because you've seen that from a lot of different lenses. So, uh, that's interesting. Obviously, we talk a lot about positive rebellion. Kind of the importance of kicking the tire, so to speak, is how Jan Young affectionately coined it when she came on the show. Uh, I believe it was all the way back in season one now, but the time flies. I'm curious, in your thought process, what is positive rebellion and do we need it and why or why not?

Speaker B: I mean, when I hear about positive rebellion, I think about challenging the status quo. Yeah, right. It's. It's about not being okay, which is doing things the way that they've always been done. I think that's a very healthy thing for any team in an organization. I think leaders should be challenging the status quo and not waiting for their team members to challenge them in their status quo. So if a leader can lead out and make it a safe place to challenge, now, that can create a lot of chaos. Because now if you have 50 people all challenging the status quo, all running in different directions, that's also not healthy. So I'm not proposing that, you know, you do everything that you challenge, still be deliberate and strategic about what it is you do and why. Yeah, challenge everything. Challenge everything, but then decide and move forward.

Speaker A: Okay. You know, and I'll tell you that there's been a lot of answers to that question. I think I've. And nothing against any of the great, you know, practitioners and leaders that have answered that question on the show before you. But that answer I love best. The reason why I like the one that you just gave best is because there's this clear element of, hey, we need to sit back and strategically discern does this make sense or not? Before we just run after it. Because, I mean, I think challenge sometimes can also lead to stakeholder tension. And it's already really easy. Much like you said, um, to as a customer success, we're right in the middle of all of it. You know, uh, I've been this thing 14 years and we've, we've always called it, you know, we're in the flywheel of all of it, you know, is what everybody says. But the truth of the matter is, and you've seen this leading these in these major organizations, it's this thing where we have to cooperate with one another in a non emotive way that as you articulated just a few minutes ago, is just quantitatively sharing story so that we can come to a business decision.

Speaker B: That's right. I'll never forget, I think, where I learned this lesson. I was at Adobe, I was on the product team, young in my career, excited about everything, and I just wanted to build every single feature that a customer asked me to build. I was right there, I was writing up the PRDs and we were going to go and execute on it like today. That was kind of the energy that I was bringing. And I remember sitting down with the VP of product, uh, at the time and showing him my roadmap and he looked at it and he said, Jared, this is like total chaos. I'm like, no, this is what customers are asking us to do. And he said, jared, just because you can doesn't mean you should. And it was very simple, very direct. Right. But it kind of stopped me and I thought, okay, yeah, there's truth there that just because you can do something, just because you challenge the status quo doesn't mean you should do that. You've got to now step back and look at it strategically, say, okay, what is the right thing to do for the business? And then go and execute on a finite number of things. That's the challenge is we, we are, you know, we operate in a world where you can't do everything, so you gotta pick. And that means you're gonna pick some things to not do. But the, if you chase fires, then you just do the thing that's hottest. And if you step back and you're, you're more strategic about it, then you deliberately create a direction. And I find that to be a lot more successful and better for the people that you lead so that they, they have confidence in what you're doing.

Speaker A: Yeah. And then it also, you know, it shows great direction and builds confidence from your peers kind of across the table. And then, you know, ultimately that all gets presented back to you know, the board, whatever that looks like from a turn, you know, from a, uh, funding standpoint. So I think all of that is huge. Absolutely. So I don't know how, but it looks like we're coming close to the end of our episode already, but I'd love to. We've had a great time chatting and learning more about you as a person, and then, you know, about the business and your side hustle and all the fun things, and tell us where we find more of you and about all these things.

Speaker B: Yeah, thanks. I think if, you know, if you're looking for help in improving customer retention, find me on Crush Churn.com or on LinkedIn. And look, if you got a car that's sitting around and you want to make a little bit of passive income, you just got to get it to me here in Utah. Salt Lake, it's not far, but if you got it here, we can make you 500 to 1,000 bucks a month. So that's. That's my offer. That's. That's what I'm, uh, doing is co hosting vehicles here in Utah. Happy to help in either way.

Speaker A: That's awesome. Well, thank you for sharing your expertise, your business advice, and, uh, just for coming onto the show and spending some time with us today, Jared.

Speaker B: Okay. Thanks so much. Appreciate you.

Speaker A: Absolutely. All right, rebels, until next time, do it big and do it different. Bye for now.