Scaling Without a CTO: Tips and Tricks for Startup Growth | The Pair Program Ep22

Tim Winkler: 00:00:05

Welcome to the Pair program from hatchpad, the podcast that gives you a front row seat to candid conversations with tech leaders from the startup world. I'm your host, Tim Winkler, the creator of Hatchpad,

Mike Gruen: 00:00:15

and I'm your other host, Mike

Tim Winkler: 00:00:16

Gruin. Join us each episode as we bring together two guests to dissect topics at the intersection of technology, startups, and career growth. Cool. Let's jump in, guys. So we are back for another episode of the Pair Program. I'm your host, Tim Winkler. Uh, my co-host Mike Groin. Mike, what's going on? How you been? I've been all

Mike Gruen: 00:00:40

right. It's been a, been a rough week. Uh, we'll probably get into it when we get into my faring, so, uh, there.

Tim Winkler: 00:00:46

Okay, Let's save, save that therapy session. Um, yeah, let's, let's give the listeners a quick heads up on today's episode. Uh, so today we are gonna be discussing the scenario in which a tech startup scales, uh, without having maybe a C T O or a, a technical founder or a co-founder in place. Uh, so we've got a couple of of excellent guests here to provide their insight on the topic. Um, Dane Baker, a founder and CEO who's been scaling his startup eco. Um, and we have Jason Cole, a, a consulting fractional cto, helped a number of startups scale out in exact scenario. I'm confident that both of you all will bring some, some helpful perspectives to our discussion. So Dan, Jason, thank you for spending time with us on the PAIR program. Happy to be here. Thank you for having us. Thanks. Good stuff. All right. Well, we, um, we like to start, uh, every episode with the fun segment that we call Pair Me Up. Pair, where we go around the room. We'll shout out a complimentary pairing. Mike, you start us off, buddy. Yep.

Mike Gruen: 00:01:42

Uh, so, uh, we're gonna go with, uh, PagerDuty and Coffee. Uh, so, uh, this week I was on call, uh, and. There was a couple, couple pages that made it all the way up to me. So, uh, coffee was definitely key in getting, getting back into functional space. Also for my birthday, my parents got me a new pour over coffee set, so it was quite well timed. So coffee's

Tim Winkler: 00:02:04

been top mind. Yeah. Yeah. I'm, uh, big into French press right now. My, my god,

Mike Gruen: 00:02:10

I can send you a link. My mom found this like guy who says how to do French press properly, and, uh, then yeah, he's very opinionated. Uh, but he's right. Felt really good.

Tim Winkler: 00:02:21

You said paper duty or page pager? Duty.

Mike Gruen: 00:02:24

Pager duty. So I was on call. Yeah, yeah,

Jason Cole: 00:02:26

yeah. I like to just tuck a little bit right between the cheek and the gum on those long nights. That's really the best way to go. That's right on my own French press.

Tim Winkler: 00:02:36

whatever gets you through Good stuff. All right, I'll, I'll keep it rolling. Uh, so my parent today is gonna be the World Cup and, uh, empathy. So as of this recording, you know, we are in the midst of the World Cup. Then super exciting to watch and follow and, you know, every time it comes around, every four years, it's the time for me. I kind of reflect and think back, like, where was I watching it at that time in my life? I've had some exciting experiences watching the World Cup overseas, and I think back to like in 2010 watching u s A, when we lost to Ghana in the round of 16, um, I was at a bar in Laos and there's just people from all, you know, different countries, all walks of life, kinda all cheering along together. And as much as there's that competitive nature, Um, you know, I also feel like there's this level of empathy that presents itself. So, you know, folks share the feelings of, of, of a team loss, even if it wasn't like their own team. I feel like they can still kind of relate to it at some point, cuz their team probably experienced a winner loss, uh, at one point as well. So, um, I felt it again today actually getting a haircut. And my barber, you know, she's South Korean. And South Korea is playing on the tv, and I could just kind of pick up on her emotion and motivation for her country to win. So, uh, you know, had some, had some empathy for, uh, winter loss. I, I, I felt like I could relate to her, so I ended up wa watching The end of that too, by the way, was an incredible finish in the 90th minute. Um, but, uh, the World Cup and Empathy, that's, that's my pairing. Nice. I'm gonna pass it over to Dane. Uh, maybe just give us a quick intro and tell us your pairing.

Dane Baker: 00:04:13

Yeah. So happy to. So, uh, and yeah, thanks guys for having, for having me. Um, excited to be here. So I'm Dan Cool. Co-founder and c e o of Eco Cartt. Um, happy to to dive into Eco Cartt now, if that's, if that's the right time. Um, so yeah, eco Cartt is, uh, we built a technology to calculate in an. The carbon footprint of a consumer purchase and, um, we apply this to the vertical of, of e-commerce, um, is kind of our, our, our, our first vertical. As we sell this technology to retailers, and we have over, we launched about two years ago, we have over 2000 brands now that, that use our solution, um, to give their customers an option at checkout to offset their order. Um, we've built a whole suite of tools to help a merchant, you know, show their customers that they're a champion of sustainability, um, and are, and are undergoing this initiative. And so that's the, that's what we built. Um, and you know, we've been growing the. Pretty quickly since, since we launched two years ago, um, we're now, we just crossed about 40. So we're really excited about, uh, the growth so far and, and about the, the future in front of us. I mean, I think, you know, at a really high level, you know, we fundamentally believe that, you know, what we're building is becoming standard in the e-commerce landscape. And, you know, if you're, if you're a consumer, you know, going through a checkout flow in the next three to five years, you know, you're, you're not gonna not have an option to make your order carbon. And or at least have that done for you. And so, you know, we're really excited about this, this, uh, powering this movement, uh, that, that we are. And so, yeah, that's the, that's the quick background myself. Uh, pairing as I'm staring out the window at some rain, uh, is gonna be, uh, a rain and a productive weekend is what I'm looking forward to.

Tim Winkler: 00:05:55

Good stuff. Maybe you can help Mike out with some of his, uh, some of his laundry Good stuff. Yeah, I'm the same way, man. I, I get motivated when it's just like I'm not missing anything by being indoors here in front of the computer. Gets pack some workout. You got it. Good stuff. Well, awesome mission to it. Eco card. Love, love what you guys are building. Um, Jason, let's pass along to you. Uh, your, your intro and, uh, and.

Jason Cole: 00:06:24

Yeah. Jason Cole. I'm the c e o and founder of d Primus Consulting, and I've been working in technology startups and building products teams and companies for about 30 years now. And over the last five years have been, uh, fractional CTO O for about 15 different companies. And my team at the Prima, uh, now have four of us who are all fractional CTOs. And right now we're serving about, uh, six companies, uh, concurrently as fractional CTOs, as well as advising and leading development teams for a few more. So, uh, Have a ton of experience in this space of how to build without having a technical co-founder. That's usually how the conversation starts. Um, and uh, I started the Premus five years ago to test a theory that you could build a company based on generosity and based on helping people build their companies, uh, whether that was for charge or for free, uh, and that you could still actually build a successful business around. and so far so good. Uh, my pairing is, uh, a mountain bike ride and a hard day. I find nothing clears the cobwebs out after a particularly stressful day, like getting out on a rocky trail and just banging my my way around for a couple of hours, you can't continue to worry about how the day went. When you're riding, you have to be a hundred percent present, or your face is gonna meet the trail within the next 30. So I find for me, when I have those really rough days, the best thing to do is just to get out there and push and, uh, force myself to kind of reconnect with my body and with the space around me. And by the time I get back, I'm too tired to be stressed anymore.

Tim Winkler: 00:08:16

I'll even need like go-to trails. I got a couple of runs out, out that way. So I'm always curious, uh, if there's one that you re.

Jason Cole: 00:08:24

Marshall Mesa is right outside my door practically. So that's my, that's my go-to ride from home. Uh, and then Potass Preserve, which is just up the canyon from Boulder, is probably one of my favorite rides cuz it's really, it's not too hard. It's nice and swoopy and has some nice technical sections. But I'm at the age now where like I'm not riding down cliff faces. So, uh, I like something that is gonna challenge me, but also I'm still gonna remember that I had fun by the time I get to the. Right.

Tim Winkler: 00:08:54

Won't be permanently forget what happened. Yes,

Jason Cole: 00:09:00

I've had a few of those rides too. Those are usually up higher in the mountains, but, uh, we try to, try to make sure at this point that you're coming back in one piece. Good

Tim Winkler: 00:09:08

stuff. All right. Well, I'm, I'm excited to jump into the conversation, guys. Thanks for the intros. Um, let's, let's get into it. So, uh, like I mentioned, we're gonna be talking about startups that scale up without having a technical co-founder or founder, c t o in place. Uh, and again, we strategically chose our guests, uh, given their diverse experience on the topic. So I'm gonna jump in on this and start with you First, Dane. Uh, if you can just shed some light for our listeners on how EcoCAR started in those early stages. You know, what was kind of your strategy going into the build of the product, knowing that you and your co-founders weren't. You know, engineers by trade.

Dane Baker: 00:09:44

Yeah. So it's a, it's a great question. Um, let's see. So I'll, I'll give a little bit of the, kind of the backstory. So, um, my, my co-founder and I started Eco Kart, uh, really because we lived, uh, the problem in our last company and, um, you know, all of the companies that I've started in the past of all, um, you. Had a similar thread of trying to make the world a better place in some way, shape or form. And, um, and so, you know, the last company that we started was an online peer-to-peer rental marketplace business that we figured was, was better for the environment than, than consumption. So renting, being better than consumption, and, you know, um, the sharing economy being good for the environment as a, as a net hole and. That was the thesis as we scaled, became very complicated and very expensive to accomplish that and to sort of delivery that, deliver that same sustainable shopping experience that we had set out to create. Uh, so we tried a lot of things. We tried to buy offsets, higher consultants. It was really complicated and expensive. So realized there was a problem and one that we really wanted to solve. So we sold that company and started Eco Cartt based off of this idea. Um, and so, you know, that takes us. About four years ago at the time, um, you know, we, my, my co-founder and I are not technical, uh, as, as you have, um, described. And so we wanted to do a few things. We wanted to first test the hypothesis behind what we were building and make sure there was customer demand. before we invested time in, in, in building, because we knew that, um, you know, we, him and I together make for a really good team and we didn't immediately have a CTO slash COFA technical co-founder to, um, to, to call upon, frankly. So we didn't have that, um, that, that engineering network, honestly. And so, um, you know, we, we figured we would go at this, our. Um, and, uh, alone. And we figured that we were, you know, we wanted to probably, um, outsource the development of the first iteration of our product and then bring things in house once we maybe raised a little bit of capital or, or had some revenue in the door. So that was kind of the general plan. Um, and that's exactly what we did. we, um, you know, wanted to first test the hypothesis that this would work. And so, uh, I flew to, to CES in Vegas and I just went booth to booth and asking merchants there if they would be interested in a solution, actually selling it as if it was already built. Um, and, you know, trying to get that customer demand, um, had a business card and everything and, and they Uh, and, and uh, that was how I got the first, you know, dozen or so merchants. Once I, you know, Really validated that that demand, we came back and, and started to build it with that outsourced firm really quickly. And, uh, and so that was the first iteration of our product and how we, and, and, you know, kind of got over that hurdle of, of building, uh, without, without a technical co-founder. And,

Tim Winkler: 00:12:41

uh, that's awesome. So I, I am curious on one, uh, the outsources firm, you know, was that something that your. Investors recommended to you? Or you just knew somebody through word of mouth? How did you come across that firm? Yeah, just,

Dane Baker: 00:12:54

uh, word of mouth referrals from, uh, you know, our network is kind of how it came about.

Tim Winkler: 00:12:59

And then when did you, I guess, first hire up, uh, a technical resource? Internal. And what was the role, or, or I guess even title, I guess, of that

Dane Baker: 00:13:08

person? Yeah, yeah. So we then decided to, again, build that in, uh, you know, shift that, that build in house. And so, Went through the 500 Startups accelerator program. That's how we got our first pree, uh, round of capital. So we had some, some, some capital and resources to be able to. Hire folks. And so that's exactly what we did. We, uh, went out and, and, and found, uh, a head of engineering to, uh, join the team and, uh, and, um, you know, started to again, shift that in-house slowly but surely. And so that's, that's what we did. And, um, you know, ultimately that shift was a tough one, honestly, right? Like it was, uh, it was one that we had to, um, you know, dedicate a lot of time and energy and, and resources into, into, um, into that shift. But it, it ended up working out for us. I'm curious on

Mike Gruen: 00:13:56

the, on the shift. Was it, what was it that made it difficult? Were you guys trying to actually move what was built by that outsource company in-house and take ownership of it? Or were you trying to, like, knowing what we know now, we're gonna build the next version of this, uh, while that outsource company maintains it, something in between?

Dane Baker: 00:14:12

Yeah, so it was, it was kind of a, um, something in between. It was, it was something that, I mean, really the challenges came because. You know, the individual that we hired on to lead our engineering efforts did not, you know, wasn't the same person that built the thing, right? And so, right. Mm-hmm. that's, you know, that's an inherent challenge a a bit. And so we, um, you know, had some sort of slow going in terms of getting things developed and, um, you know, the outsource firm that we initially, you know, hired to build the solution. Um, you know, there was, uh, it was, it. They spoke a different language. And so there are a lot of like comments in the actual code base that explained how things worked. Mm-hmm. Or in a completely different language. Mm-hmm. And so, uh, it was, it was a challenge in that, in that regard. Um, and also we, we, we, we didn't, uh, we kind of went cold Turkey with them. We didn't really, we didn't think we needed to have them on retainer to like, to continue the handover process. And so that was. Also an inherent challenge cause we kind of had to figure everything out ourselves. And so, um, that's, that was a little bit of our experience. Hmm. Yeah,

Tim Winkler: 00:15:21

that's interesting. I, I've got a couple other questions I wanna tap into that, but I'll, I'll quickly jump over to, to Jason and then we'll, we'll, we'll come back to that Dane. Um, so Jason, just for context, for our listeners, maybe you can expand on what the role of, like a fractional CTO might consist of, like maybe a couple of different scenarios that you've come across where your service comes into play for, for these early stage.

Jason Cole: 00:15:43

Yeah, so a fractional CTO is, uh, usually someone who's fairly experienced. So someone who's got 10, 20 or more years, um, leading technology teams and they're serving a company and doing it usually one to two days a week. And that can either be a dedicated couple of days, like you get Mondays and Wednesdays, or it can be kinda spread across, but. It is basically a way to get somebody who's got a ton of experience and to be able to afford that experience where a full-time, uh, person at that level would just be completely outta reach for most companies, kind of pre-series A, um, or pre-series B maybe. So the kind of, the way that it works, you know, from my perspective is I'm usually working with two or three clients at. I'm shifting between them and, um, I own the product development, uh, or technology development for them. I'm understanding the business strategy, figuring out how technology either delivers it. If this is a tech forward software product company, or the technology strategy enables it and accelerates it if it's more of a tech enabled company and then I'm putting together. The team that's going to deliver it or leading the team if they're already in place, um, putting together a plan that says, here's how we get from here to there, and then going and executing. And the goal is put together a plan, get it in action. Build a team that's going to continue to carry this plan forward, and then replace yourself. and ideally the company's growing. And so as they grow, they do get to the point where they need full-time technology leadership and can afford it. And that's usually the time where, uh, a fractional CTO will actually, hopefully, uh, help hire their replacement and then sort of hand off the keys and, and move on to the next.

Tim Winkler: 00:17:48

And when you backfill yourself, when you replace yourself, um, is this the type of thing where you're still in the seat and you're kind of doing the interviews with the, with the, with the folks that are coming through the door and trying to figure out if they're gonna be a good fit for the, for this founder? Uh, for the, for the leadership,

Jason Cole: 00:18:04

yeah. Often. I mean, you're really, most of the time you're working with a company that doesn't have a technical co-founder, so they don't have anybody in that kind of C level leadership seat or. Maybe anybody on the leadership team who really has the technology experience and expertise to be able to even know what a good hire looks like. Mm-hmm. So, uh, yeah. And in those cases, I have been interviewing prospective replacements, um, have been even working through my network to try and find somebody who I think could be a good fit and is looking for a full-time role. And the goal, I mean, with every one of these companies, I'm treating this company in product and budget as though they were my own. So I really want to make sure that it's going to be successful and that the next person is going to just kind of pick the ball up and keep running with it. And we don't go through any sort of three to six month transition period where they're going, I don't know who this other guy was, but he was a complete moron. We have to change everything. How

Mike Gruen: 00:19:03

do you, so since it's important for the companies to be successful after you. what's your vetting look like for actually which customers you take on and, and are there, are there any like that you're just like, yeah, this isn't right for me? Or like, how do you, you, I'm curious how that part of it works.

Jason Cole: 00:19:21

Yeah. You wanna make sure. I think in it's, in many ways it's, it's the same kind of thing you would go through if you were considering becoming a technical co-founder, although it is a little bit lighter. I don't have to worry too much about whether I think the company absolutely can succeed or not. I'm looking at it from the perspective of, uh, are these people that I feel like I I can work with? Um, are we ethically, morally, and sort of personality wise aligned? And I've had a few where I've said, yeah, that's good for you if you can get people to pay for that, but you frighten me a little bit Um, and, uh, I'm looking for, do I feel. I can actually find the way that technology can make this successful. So a lot of times it's, do I understand the product? Do I think we can actually go build it? Um, but for those companies where it's not building a software product, it's more looking at it and saying, how, how does technology actually make this happen? Mm-hmm. And do I feel like I can bring the right skills to bear? Often find the right technology and, and select and buy versus build, and do I feel like I can actually get them where they need to go? Um, and then it is some, some level of it is do it, does it feel like this thing even has legs at all? Uh, but I've also, part of what I've been kind of trying to do these last five years is help people achieve their dream of starting a company. So I don't have to say, oh, this is gonna be a. If I believe, yeah, this can actually make, it can survive. That there's something there that they can go and take to market. Uh, I just want to help them try and get there. And, you know, the other thing that's interesting is I don't have to be the expert in their business, right? Mm-hmm. what's, what's interesting, and Dan kind of talked about it, the founders are passionate about what they wanna do. They know this space, they know what the customers need. Hopefully, uh, they just don't know how to deliver the. so I know how to deliver tech. I can absorb the business domain. And, uh, the, the fun part about a lot of these projects is we all end up learning from each other a ton. So I'll come out of there an expert in that industry, but I don't need to be one to get started. Mm-hmm.

Tim Winkler: 00:21:38

Dan, uh, you have a co, a co-founder, just one co-founder. That's right. Um, and what is Juan, your background? Is it her

Dane Baker: 00:21:48

background? Yeah. Yeah. So we, um, we both come from, um, a founder background, so we started a couple of companies together. Um, and then each of us have gone on and, and invested a bit within the like, VC world. And so yeah, we, we've come from a pretty similar background in that we. um, founded companies together, albeit with a different skillset than than each other. And, and it really works well in terms of kind of, you know, complimenting, complimenting each other. Um, but we both as well have, um, have this, this, the shared passion for the mission and the work that we're doing.

Tim Winkler: 00:22:32

Have you worked with engineers and, and like product teams in, in. Background prior to founding Eco Kart? So, a little

Dane Baker: 00:22:39

bit. Yeah, a little bit. Um, you know, I think that, uh, you know, the, the last company that we both started was more, we, the actual technology was more out of the box than, than, than anything. And so we largely paid for like a platform as a service than, than like building an internal or even, or even managing an external. edge team. And so that's kind of, that's part of where the challenge of, um, learnings early on came from. Right? It learned a ton, uh, about, about engineering just generally and managing engineering teams over the last, you know, two to three years. And, and so I wish that, uh, I would've, I would've met Jason two years ago. We would've been having a little bit of a different convo.

Tim Winkler: 00:23:27

Well, I'm always curious too, you know, cuz you made a, an interesting point when you say you hired a head of engineering and I think this is something that, you know, we've seen a lot of companies where they, they get caught up in like, well I think I need a c o, right? Because we need somebody that's just gonna lead and build the department. Um, when really that's not what they need. They need somebody who's more of this kind of hands-on, almost lead engineer. It could be a founding engineer. um, did you tap into some advice and maybe it came from 500 startups or, uh, just from, you know, your own network of what, what should I be looking to hire for right now and, and what, you know, what are my options and what should I be looking for in the, in the skillset of this person? And I wanna peel that back a little bit more because I think that first engineer hire, I think, is a really interesting talking point of what that skillset looks like. People management to just, you know, really good hands-on engineer. Uh, so how did you navigate the, you know, this is what I think we really need at this

Dane Baker: 00:24:25

stage. You know, I wish I could say there was a lot of thoughtful discernment that went into it at the time. I, I wish I could say that really it was just, we, you know, again, we were starting from a place of, Uh, there's this code that lives somewhere in the ether that I don't know how to access. I don't know how to read. I don't know anything about it. And it governs our entire revenue and our ability to, to, to garner further revenue. And so it was more of just, let's bring on someone who knows. how to code. It was really the, the who also, you know, who has, of course, who, who passes the, you know, the culture check and everything to do with what the soft skills we were looking for. Um, that was really just the, the, our first. That was at like, you know, kind of taking, taking you through into my mindset of how, uh, at the time Right, which was again, um, there's been a lot of learnings between then and out, but that was the, the initial kind of thought process.

Tim Winkler: 00:25:33

That's interesting. Jason, do you have, um, any, any insight onto that on how you advise folks? When you talk about backfilling yourself, what are the questions that you are kind of like asking with the founder and what are the things that you're recommending when you talk about like the mold and the profile of the person that they actually need at this stage and their growth?

Jason Cole: 00:25:54

Yeah, and I think, uh, Even before talking about replacing me, when I talk to people who are starting with, well, somebody told me I need a technical co-founder. Um, what do I do? I think that there's really, there's two pieces of that, and you've kind of touched on it, but one is what kind of company are you? Are you a tech forwards software product company, in which case you are going to need to have a very strong leadership presence owning and and setting the path for that technology? Or are you more of that tech enabled company? And for the tech enabled companies, it can become much more of talking about buy versus build and looking about how do we assemble the technology that we need? What do we need at a certain point in time where if you're a software company, if you don't have a product, You don't have a company. Uh, so starting with that, and then from there, figuring out, okay, how much technology investment do we need to make? Who needs to be doing this? And I think with the tech enabled companies, you can often get somebody who's sort of tech savvy but not an engineer. And in some cases that's actually smarter because an engineer's always gonna wanna build and. Any empty space must be filled with code. And so you can't get a real balanced buy versus build because it's always, they look at everything in the market and they say, well, I could do it better. Um, so that that side, you're kind of looking for more of somebody who can kind of assemble and guide the business side of the team through that decision of how do we, how do we help this accelerate on, if you're on the software side, then you're really talking about. What do we have to invest right now? What do we need? And uh, to me it's always the difference between do I need a builder, meaning I, as the non-technical founder know what I want to do. I can set the product vision, I can kind of connect the dots between business and what the software needs to do. So I just need somebody that I tell 'em what to do when they go build it. And that's more of that founding engineer or first. Or do I really need somebody who can make that translation from business to technology? And that is really more of the cto. And I think the, the biggest mistake I see companies make early on is they will not have anybody who can make that translation. They've got business savvy founders who really don't understand how to make the technology do what they want to do, but they know they. and then they try to bring in an engineer or an outsource team and just tell 'em what to build or hope that they're gonna figure out what needs to be built. And what you end up with is often an engineer who's got their hands poised over the keyboard saying, okay, tell me what to do. And you've got the business founders saying, I don't know, you tell me. And then everybody gets frustrated. Uh, if you get more of that senior. CTO person who's who's used to standing at that intersection between business and technology, they can make those translations, and then they're the ones who are really making sure that whoever the engineers are, that they're doing the right thing at the right time and focusing on the most important thing at any point in time so that you can be as efficient as. So it's like that's, that's kind of the tree that I walk people through. And then from there you say, okay, now based on what you need for the company, what can you do right now do you think, as you can't afford to bring that leader in? Then it's like, okay, well either you're not ready to start your company, which sometimes is the best answer. Rather than flailing around and burning $50,000 to find out that you were not ready to start your company, uh, or you are coming back and saying, Okay. I need to go and get a little bit of guidance or I need to learn myself a little bit more to be the leader that the company needs until we can fill some fill in that gap. Do you think

Tim Winkler: 00:29:57

there's

Mike Gruen: 00:29:57

companies that are sort of in that consulting space that where they, they can actually help do that translation? They have the engineers, but they also have like some senior product experience and they can really help that founder t. And I'm curious what your experience has been. I've worked with a couple of them. I've had mixed results. Um, some that real, if it's a niche, uh, like market where there's certain players and they definitely know these are the technologies that get plugged together, like then it goes really, really well. Um, and then other cases, the other side of the extreme. So I'm just curious what your thoughts are

Jason Cole: 00:30:32

on that. Yeah, there are some, uh, I, there definitely are some that bring a little bit more of that. In a sense, it's almost product expertise, right? Instead of tech engineering expertise. Um, I think almost all of them will say that they do which is the problem. Yes. And you do have to really be careful and ask a lot of questions of, okay, well how do you help me if I just show up and say, I've got this crazy idea. I don't know how to make it happen. What are you gonna do? And if the answer is, well, we'll start coding, um, that's a bad. But I think some of them will bring it, the, the advice that I normally give people, especially if they say, well, I'm just gonna go and hire an outsource firm. I mean, I think Dan kind of learned some of this, uh, as in his trial by fire. What I tell them is, you need to expect that at least half of your time is going to be spent guiding that team and telling them what to do. So if you're not ready to do that, get ready before you start paying. Mm-hmm. uh, and of course the horror stories. And a lot of people that I end up actually helping are often ones who tried to work with an outside firm, didn't have anybody who could help actually translate and lead and set priorities, and they end up with this flaming tire fire of a code. And then they're, you know, they want to add one more feature in the mm-hmm. the development firm says, okay, that'll be a hundred thousand dollars because we can't extend this

Dane Baker: 00:31:59

any further. Mm-hmm.

Mike Gruen: 00:32:01

and I think, and I'm, I'm curious, Dane, for your opinion and Jason, both of you, like, um, when you are looking at those firms, um, what are some of the questions beyond just what can you help me with? I have one in mind that I think of like, what's the transition plan? Like, how do you see yourselves working your way out of this contract? I, I don't wanna be married to you for the entirety of my product's existence, so are there any other questions like along those lines that you can think of that you would be sort of talking to about them? Either one of you.

Jason Cole: 00:32:32

Yeah. Dan, go ahead. You've, you just went through this, so maybe in retrospect are the questions you wish should you have asked might be the question

Dane Baker: 00:32:39

Yeah. Um. I mean, yeah. So again, like have learned a ton over the last three years, you know, I mean, we have since moved all of our engineering in-house. We have a team of about 12, going on 15 engineers, and so Wow. You know, we, we, we've kind of hard shifted, right. Um, over the course of that time, you know, have, have learned a ton about, you know, um, The, the, like, the type of persona that we need at different stages. I think, you know, early on, as Jason just kind of alluded to, you know, it was really important for us to have someone who, you know, can, can just execute, who can code incredibly well, right? As we've scaled. Um, now what's really important to us is, um, someone who, uh, can lead their team like a, a true engineering leader, someone who is focused. People management and people development and org structure, building and infrastructure and code reviews and setting up all of the efficiency and process behind developing code at, at a high velocity. And so that's, you know, now what, what, what I'm focused on in terms of, um, You know, how, how I can guide and lead the team a little bit is in that way. Um, early on, you know, for us it was, you know, we needed someone to execute and we needed someone who can, who can take over to the code and, and help us, you know, bring on our first couple hundred customers. Like, that was like, you know, the do or die for us at the moment. Cuz again, we were, we were an early stage startup. I mean, we were, they were like, they were like, it was just pretty much my co-founder and I at the time. We then, you know, brought on a, a head of engineering. It was just three of us in a room that were just like, you know, And try to, and try to, you know, secure demand for the solution and, and, and, and, and make an impact and make a difference in the world. So that was a little bit of our journey. Um, it's obviously, you know, changed a lot in, in how I think about things and I've learned a ton. But that's, um, you know, that that's kind of our, our, our journey a bit.

Tim Winkler: 00:34:39

And that head of engineering, you know, you said you brought on when it was just a couple of you, um, He or she proven to be. That's, that's that person that has evolved into a, a leader as well of people? Or was that already a trait that came along when, you know, when they joined? I'm just curious in terms of, we hear a lot of times getting layered, right? So maybe you hired a head of engineering and then your team grows to 15 engineers and now you're like, actually we might need a VP of engineering now. Um, and maybe this head of engineering isn't that person to be the. uh, how does

Dane Baker: 00:35:10

that played out for you? Yeah, I mean, it's a, it's a great question. These things certainly have crossed my mind, and again, as I have learned about, you know, like just how to build an org structure within, within, uh, a field that was completely foreign to me over time. Mm-hmm. But, um, but yeah, so, you know, we, we've had a few different, um, uh, folks that have, have led our, our engineering team, you know, over the last couple of years, right? That first head of engineering wasn't the right person to scale our. Um, to what it is today. And so we, you know, we, we, we parted ways and now we have a, a, a director of engineering who's leading our engineering team of 12 and, and, and doing a great job. And so, um, you know, that's, that is the, uh, kind of context and an evolution of what we've had to have, have had to go, but certainly have thought about, you know, again, there's different personas of people. are relevant for certain stages of, of a company. And so for us at the early stages, very different than what it is now, which will, you know, might be very different than what it is in, in two years. Mm-hmm. And so that's just, that's just the nature of, of the game.

Tim Winkler: 00:36:14

And, and I think it's just so interesting that, you know, there doesn't have to be this negative stigma around like, that we parted ways. Well, you know, maybe that was for the best, you know, and it, and it's the type of thing we see quite a bit in product too, of like, look, I need you to get my product, uh, this stage and. We're obviously gonna be doing feature builds and then don't, I'm not sure. Like that's not your expertise and that's not, you know, the no hard feelings. Uh, but being able to part ways and do it in a sense of, you know, like a fractional C t o, it's like, it's like I'm coming in here for one for, for a certain period of time, and, and I'll know, like I'm not here to. Drag this thing out for years, you know? And so, uh, I think it's just a fascinating concept of, doesn't have to always be looked at. It's like, well, didn't work out, you know, this is, this is the

Dane Baker: 00:36:56

disaster. Totally. Very much. Agreed. Yeah. I,

Jason Cole: 00:36:59

I, I say my job is not to embed myself like a tick in every one of the companies that I work with, Um, and it's. You, uh, you, you bring an interesting point up, and I think this may be a podcast for another day, but, uh, the idea of needing different people at different stages, and not only do you need that sort of as the organization grows, we need people who know how to manage a larger organization. You need different personalities, even in those individual contributor roles. The engineer you need when you are three people in a room just trying to get the. Hundred customers is not the same engineer that you need when you've got 10,000 customers and you're starting to figure out how to scale and how to write solid, repeatable code, um, there's, there's a whole sequence of, of personalities and in fact, a healthy startup as it's growing, you see those people peel out. Um, I, there's a great model that I heard a while back of, uh, explorers, settlers, and town planner. And you need the explorers early on. They're the ones who just will hack it together In a weekend, it works. You d you now you've got a product that you just got done selling at c s and uh, you can now actually show it to people. Uh, but those guys will lose their minds when you start building process and you start having agile rituals and we start having to have a daily standup. They're like, I don't wanna talk to people. I want to code. You actually see those people roll out and that's a, that's a healthy transit. as you go, and as they are replaced by people who are actually excited, not about hacking something together in a weekend, but are excited about building something that scales and building something that now that you're solving different problems. And those are the kinds of problems that they get excited about. Mm-hmm. And I would

Mike Gruen: 00:38:46

say, I mean, I agree with you and. In general, but I do think that there are some people who make those transitions naturally, that have been in startups. They know what's necessary early on. Like there's, there's certain engineers that I've worked with multiple times where I'm like, yeah, I know he or she knows what needs to get done right now. And they also know what the next level layer or two layers look like. And they're gonna be able to, to transform into that other type of, Going from packing it together to like, okay, now we need to build something maintainable, sustainable, extensible. Yeah. That type of stuff. Um, yeah, I wanna, right. There's, it's rare. Um, but it's one of those things I think, um, if you are an engineer and you're looking at things like, recognize where your sweet spots are, what do you enjoy doing? What don't you enjoy doing? And don't make it like a confrontational thing. Like just recognize that this is the evolution of a company. It's the evolution of your career. It's the evolution of. Um, and it makes those conversations a lot easier of like, this is what we need now, this is what we're good at. Like, and, um, whether, you know, it doesn't always have to be this, uh, friction, uh, and, and negative connotations. Um,

Jason Cole: 00:39:54

but yeah. Well, yeah. I think it's the manager's job to be asking that question all the way along. Absolutely. Is, you know, here's where we are, here's where we're going. Mm-hmm. here's how, that's how, here's how your life's gonna change. Do you wanna come along? Right. Is that what not? Right. Great. Let's, let's separate on happy terms. If so, let's talk about all of the things that are gonna change in your world, right? And all of the things that I'm gonna do to help you get

Tim Winkler: 00:40:16

there. Absolutely. Yeah. We're wrapping up on, uh, on our time on the topic. I'd, I'd, I'd love to, uh, maybe do a follow up on this just because I've got, I'd love to hear some horror stories as well of what you've seen out there, Jason, cuz I've, I've got a couple too. We, we, we've seen a couple of things. We did a fractional CTO engagement with a company where the offshore dev team just owned all of the code base and their name and the GitHub repo. And, uh, so we, we were like, we need guard rails up here, clean this thing up. But, um, I'm sure we could, we could, uh, exchange war stories for a lot longer than the time that we have Halloween.

Jason Cole: 00:40:55

I, I think you should. And I can tell you about the, uh, the single developer who took an entire site hostage and then even after they got it back, continued to hack it until they finally paid a ransom

Tim Winkler: 00:41:10

Wow. That is a good one. All right, well, yeah, we'll have to save that, that, that's, uh, that's what we'll open with on our next episode. Um, I, I had one quick, quick question for you, Dan. In terms of, like you said, was it 14 engineers on your team? how many product folks do you have? Or do you have a product team? We do.

undefined: 00:41:28

We

Dane Baker: 00:41:28

do. Yeah. So we, um, we now have a, uh, we, so we broadly have sort of org orged it into e p d, so engineering, product and design. And our product and design team is five folks. Okay.

Tim Winkler: 00:41:45

And then you have 14 folks on the engineering. That's pretty healthy. Yeah. Tech team in terms of, you said you're about 40? Yeah,

Dane Baker: 00:41:53

exactly. Count. Yeah, so about half, half roughly around on like within E p D. Right. And then the other half mm-hmm. across, go to market and, and support and is kind of how we, how we think about it. Nice.

Tim Winkler: 00:42:07

Well, I, I, I wanna, um, I wanna transition us to the, the five second scramble here. Um, just because, you know, we've, we've got, uh, about eight minutes left, so I. I'm gonna transition us. This is, um, this is a segment where, you know, I'm gonna ask each of you a series of questions. You gimme your best response within five seconds, and like a rapid fire q and a, um, some business, some personal, um, I'll go ahead and start with with you Jason. Um, so as a founder leader of a startup, what is the number one thing that you would say that keeps you up at night?

Jason Cole: 00:42:42

Uh, continuing to find more business to keep everybody fed.

Tim Winkler: 00:42:48

What's the number one trait that you look for in people when hiring engineers to a startup?

Jason Cole: 00:42:54

Oh gosh. Um, somebody who's excited about the challenge and is curious about the business.

Tim Winkler: 00:43:04

What's your favorite aspect of working at the premise?

Jason Cole: 00:43:08

Uh, that I get to put the question, what is the generous response at the front of every single conversation? Cool.

Tim Winkler: 00:43:18

What's the biggest challenge that startup founders will face in 2023?

Jason Cole: 00:43:24

Learning how to bootstrap.

Tim Winkler: 00:43:28

What's your favorite programming language?

Jason Cole: 00:43:31

Um, basic.

Tim Winkler: 00:43:35

What's the favorite state in the US that you've ever traveled to?

Jason Cole: 00:43:41

Uh, I think I gotta go with, uh, Massachusetts.

Tim Winkler: 00:43:47

Most delicious food item you've ever eaten.

Jason Cole: 00:43:52

Um, I had some amazing pasta in Florence, Italy last year that will probably never leave my taste buds.

Tim Winkler: 00:44:02

um, favorite superhero Batman. Right answer. Yeah. All right. Definitely. All right. Good stuff. All right. You are about to be on the clock. I'm nervous now. You ready to go?

Dane Baker: 00:44:14

I'm nervous now.

Tim Winkler: 00:44:17

Um, what problems are you solving at Eco Cartt? Uh, we

Dane Baker: 00:44:21

are solving the problem of it being really difficult and expensive to show your customers that you are a sustainable brand and help you accomplish those in a really frictionless and, um, you know, non, non-complicated way. Who are your users? Yeah, so. Our, you know, our, our customers are our merchants and, you know, of course their customers, their shoppers are, um, also really important to, to the entire model. So it's, you know, we're inherently a b2, B2C company, but we're we're building for, so, building for both. What type of engineer

Tim Winkler: 00:44:58

thrives that eco cartt,

Dane Baker: 00:45:00

I would say, um, very similar to Jason's answer, actually one that's really excited about the problems that we're solving. About our mission. Um, and one that's also curious about the business side of things and, and driven by business outcomes. What's

Tim Winkler: 00:45:19

your favorite part about working at Eco

Dane Baker: 00:45:21

Kart? Getting to wake up every day and, um, work on helping make the world a better place in some way, shape or form. And, and just the act of building is, is what drives me.

Tim Winkler: 00:45:35

What's the number one trait you look for in a co-founder?

Dane Baker: 00:45:38

Uh, complimentary skillset to my own, uh, actually, and so, and we could probably go on for, you know, about a whole podcast episode of what, what, what, where my weaknesses are.

Tim Winkler: 00:45:49

what's the favorite country you've ever traveled to? Ooh,

Dane Baker: 00:45:52

Spain. Hello, Spain. Nice. That's the right

Mike Gruen: 00:45:55

answer.

Tim Winkler: 00:45:56

Yeah, that's awesome. Um, if you have one day left to live, would you spend it with Morgan Freeman or Denzel Washington?

Dane Baker: 00:46:03

Oh, wow. That's a good one. Oh man. Morgan Freeman. I mean like you just, I feel like you just have to.

Jason Cole: 00:46:13

And then you're already gonna know what God sounds like when you meet him, right? I was gonna say, does he get to narrat my death?

Tim Winkler: 00:46:19

just read you a book on your bed, on your deathbed. Exactly. Um, you prefer your eggs fried or scrambled? Ooh,

Dane Baker: 00:46:25

fried. Favorite Disney character? Mickey Mouse, the classic. Hi.

Tim Winkler: 00:46:32

That's it. These were all right answers. You guys nailed it. Um, good stuff guys. Well, thank you so much for joining. Sharing your, your knowledge and insight, uh, with, uh, with our audience. And, um, appreciate you having, uh, coming out and being on the PAIR program. Thanks

Dane Baker: 00:46:47

for having us.

Jason Cole: 00:46:49

My pleasure All.

Dane Baker: 00:47:07

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