The Rise of Fractional Tech Leadership: Perspectives from Industry Experts | The Pair Program Ep46

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, and I'm your other host, Mike Gruen. Join us each episode as we bring together two guests to dissect topics at the intersection of technology, startups, and career growth. Welcome everyone to The Pair Program. I am Tim Winkler here with Mike Gruen. Mike, we talked about a little bit earlier, but, uh, we are. Uh, entering playoff hockey, which is a great time of year. Uh, the drama is about to unfold between, you know, both our squads matching up in the first series. Are you feeling, feeling confident? Are you feeling like you guys, maybe you're sleeping

Mike Gruen: 00:00:55

on us a little bit? I don't think we're sleeping on you. Uh, no, I'm feeling pretty good. Uh, I mean, President's trophy. I know there's a lot of people who think that's like a curse, but like, if you actually run the numbers, it's not feeling pretty good. Um, I mean, whatever, it's, it's the playoffs, it's like everything that's about you too.

Tim Winkler: 00:01:13

I'd be feeling good if I was, you know, you never know what's going to happen, but you know, for, for the listeners, I'm, I'm a big caps fan. Mike's a big Rangers fan. And by the time everybody listens to this, uh, the series will probably be over. So it doesn't even matter what you're saying. But, uh, the reality is, uh, it's always cool. Cause like, I remember back to our first episode, You know, uh, you're wearing your Rangers jersey and wearing a cap jersey, so we'll have to, we'll have to do a, another episode here after the, the victor is crowned, do some public shaming. But, uh, I'm, I'm pumped. We'll, we'll see if we can maybe get together for, for a game. That'd be great. Yeah. See something in person. But, um, cool. Uh, so I'm excited for, for today's episode. It's actually, you know, something that we've, we've talked about, uh, on our previous episode, uh, uh, about fractional, you know, a fractional CTO, but we're going to dive a little deeper into this concept of fractional tech leadership. Uh, you know, it's an area that, you know, uh, we at Hatch has, has seen really kind of take off and popularity in the startup world over the last couple of years here. Um, and so we want to expand on it, uh, and build a little bit of awareness for, you know, those listeners that are maybe considering going down that path, or maybe we're already down that path and, you know, want to, you know, maybe learn a little something extra. Uh, we've got a couple of, uh, excellent guests joining us, um, today. So we've got a couple of folks that have been navigating the, these waters for, for some time. And, uh, again, what we love about our, our kind of format is we get to bring on two, um, two guests. To catch it from a couple of different perspectives. So, uh, one, one of our guests is, uh, you know, going to be taking the fractional CTO side. Uh, we've got Matt Walnock, uh, joining us on that front and then taking it from the product perspective. Uh, we have Dan Macaron, uh, guys, thanks both for joining us on The Pair Program.

Dan Maccarone: 00:03:12

And by the way, I'm ready to walk off the podcast because I'm a Bruins fan and

Tim Winkler: 00:03:15

uh, so all right, let's, let's just air horn, air horn this man out here.

Dan Maccarone: 00:03:22

Sucks to be you. Hey man, we can, we can beat the Leafs I think.

Tim Winkler: 00:03:32

I'll fill you in on how the, how the playoffs are going on our side and we'll compare notes. Um, so before we dive in, we, we, we go through, uh, you know, our traditional, uh, first segment pair me up where we rattle off a couple of compliments, complimentary pairings, Mike, you usually TS off. Uh, what do you, what do you got for today?

Mike Gruen: 00:03:50

So yeah, today I'm going with a tea and cribbage. Um, so cribbage is a great card game. I learned it in college, um, to playing it, play with my wife all the time. We drink tea. Uh, they just sort of go together. It's a nice, relaxing way to, to spend an evening. Um, and, uh, yeah, so that's my, that's my parent. I didn't know you

Tim Winkler: 00:04:11

were an 85 year old woman. This is great. Have we

Mike Gruen: 00:04:17

just met? I

Tim Winkler: 00:04:19

think

Mike Gruen: 00:04:19

you

Tim Winkler: 00:04:20

do. I was going to

Mike Gruen: 00:04:21

say maybe knitting. Yeah. I mean, you remember when I came to the hockey game and we, I sat there knitting the entire time.

Tim Winkler: 00:04:29

Tea and cribbage. Yeah. Wow. That's epic. Um, I don't even know if I've ever played cribbage before. Have you guys played cribbage before? I have, I have when I was 10. Is it like a two person, just two people could play or is it multiplayer? You can play two, three or four. Okay. I don't have too many more follow up questions to ask you. What kind of tea are we drinking, Earl Grey? No,

Mike Gruen: 00:04:55

I just go, I'm simple. Irish breakfast or something along those lines. English breakfast. I was gonna say like

Tim Winkler: 00:05:02

with whiskey and tea. Cool. All right. I'll, I'll hop in. So I'm gonna, I'm gonna go with a, uh, a food pairing, um, with McDonald's and Krispy Kreme doughnuts. So this was, you know, just recently announced this kind of this partnership between these two fast food goats, in my opinion. I think it's a genius move. Um, but McDonald's will is. For those that don't know, McDonald's will soon begin offering Krispy Kreme donuts on their menu. I think it rolls out later, later this year. Is that because the ice cream is always broken? Is that just coming out like soup? But, uh, you know, I grew up, it's a

Dan Maccarone: 00:05:43

glaze now. It just puts on a donut. It's nice.

Tim Winkler: 00:05:45

That's right. That's right. I mean, I grew up on Krispy Kreme donuts. I think it's, I think they're, they're fantastic. And then, you know, I don't eat McDonald's that often, but if I do, there's no doubt I'm going to. You know, be adding on a Krispy Kreme donut. So I think it's smart, uh, little pivot on their side. Uh, and now that that's out, I've been seeing, you know, every other fast food chain kind of offering something else similar. So like Wendy's popped up and they're offering like Cinnabons as, as their thing. So. So anyways, that's, that's my parent. I'm have, have you guys, Krispy Kreme? Is that, how's that rank? If you're, are you a Boston guy? So are you a Duncan through and

Dan Maccarone: 00:06:22

through? I am a Boston. I don't need sweets. So donuts don't really mean much to me, but I do like Duncan, uh, quite a bit. I like my coffee. My wife thinks it tastes like swirl and we, um, don't go to the same coffee places now.

Tim Winkler: 00:06:35

I've been enjoying the, the, the Dunking, uh, commercials. I think they're pretty creative. They're really fun. I agree. Um, cool. All right. Passing it along. Uh, Matt, how about a quick, uh, a quick intro and then, uh, you're pairing.

Matt Walnock: 00:06:49

Yeah, very good. Um, so Matt Walnut, um, uh, with longitude 77, we've been, uh, working for the last nine years in a fractional capacity. I've got a partner that works in a fractional capacity as with the CEOs. I work with, with the CTOs. Um, Pairing, I mean, the weather's getting warm and things are getting green. I love being outside. So it's hiking and cold beer and there's, there's a lot of breweries. I live in Northern Virginia, just west of here. There's a, you know, throw a rock, hit a brewery every, every 20 yards. Um, so there's plenty of options. Um, but. Yeah, it tastes better after you've sort of climbed a hill.

Tim Winkler: 00:07:23

That's solid. I can totally agree on that. Have you, this is bear chase. Have you, uh, been out to bear chase?

Matt Walnock: 00:07:29

I was just there last weekend. Yeah.

Tim Winkler: 00:07:30

Were you? Yeah. Did you do Raven's rock?

Matt Walnock: 00:07:32

No, we did Raven's rock two weekends ago. We were, we were, um, uh, Sam more shelter last weekend. It was cool. We did about a little section of the roller coaster.

Tim Winkler: 00:07:42

Nice. My wife and I got married at, uh, at bear chase at the house. That's connected to the, Oh, very nice. Yeah, it is. It's a really, really cool, cool brewery. But, um, I agree. It's something about, uh, a beer just tastes so much more satisfying after, you know, taking on a hike of some sort, but yeah, Good pairing. Good pairing. All right. Uh, Dan, we're, we're, we're testing you here. You, uh, you're prepared. I got

Dan Maccarone: 00:08:07

it. I'm prepared. I got

Tim Winkler: 00:08:08

this.

Dan Maccarone: 00:08:08

Yeah. I agree. I love to carry a bunch of years in my backpack to reach the end of a, uh, like, um, what's called a, When you get the, the, the hike and you had to hike back, you can sit by the lake, have a beer and then watch that. Oh, it's the best. It's the best. Not my pairing, but I'm, I'm with you. Um, so, uh, yeah, so, uh, Dan Macaron, I, uh, I run a company called charming robot that is been kind of consulting in product for about the past 14 years, but I've been doing the fractional. Chief product officer role for about four, four and a half years. Um, and, and kind of still do a lot of agency work on the side. But what I've found with the CPO is that it can mean different things to new people, which I'm sure we'll dive into. Um, but my, my expertise has really been about helping people launch their products and grow them for the first 18 to 24 months as a CPO, and then kind of finding my replacement as, uh, as I built the team, but, um, yeah, that's My pairing is, uh, champagne and formula one racing. Uh, and the reason they go together for me are my wife and I, and. A couple, another couple of friends of ours, we watch all the races together. Um, not in person, we, we zoom them or FaceTime them. And that when the race kicks off, we pop a bottle of champagne on both sides. And every single race doesn't matter where it is or what time of day or night it is. And generally it's. Not a time you want to be awake. Uh, but we drink the bottle of champagne over the course of the hour of the race until they pop the champagne at the, uh, at the, uh, at the end of the race. So it's a pairing. That's like been a big, a big part of, uh, that, that tradition for a while now. And I, uh, feel like it. It fits into this, this, uh, really you guys have created.

Tim Winkler: 00:09:53

Nice. Yeah, that's solid. Yeah. Most formula one, or is it a lot of international races?

Dan Maccarone: 00:10:00

Yeah. You get a few in North America, like in Austin or Vegas, uh, Montreal, but you, you know, like the one this weekend is 3am it's in China, uh, which, you know, it doesn't, it doesn't, it doesn't work well on the East coast, but, you know, it's, you know, it's, it's, you know, it's, it's, it's, it's, it's, it's. It can be fun sometimes you have a 3 a. m. total darkness and you're popping a bottle of champagne, you know, it's great.

Tim Winkler: 00:10:22

Is the, the iconic race I always associate with like kind of like a bougie ness, is that Monaco?

Dan Maccarone: 00:10:27

Yeah, Monaco is, is I think the last race of the year and it's, it's uh, it's a, it's a cool one. It's in the city, it's not a track, it's like you're racing around Monaco, it's really awesome. I've never been like, I'm not, I was going to say,

Tim Winkler: 00:10:40

it's like the a list of celebrities all make it to Monaco,

Dan Maccarone: 00:10:44

like 20, 000 a ticket. Like I'm, I'm okay. I can watch it on ESPN. It's totally fine.

Tim Winkler: 00:10:51

Yeah. I like it. Champagne and formula. One. I didn't see that coming. You, you, uh,

Dan Maccarone: 00:10:59

I feel like a

Tim Winkler: 00:11:02

peasant with McDonald's now. I

Mike Gruen: 00:11:04

just feel like I'm a. I mean, it is nice to see that they're, yeah, they're not trying to do, uh, health food, like, you know, right, right.

Tim Winkler: 00:11:14

Uh, cool. All right. Well, let's, uh, let's transition, uh, into the heart of the discussion. So again, you know, we're going to be peeling back the curtain on fractional tech leadership. Uh, some of these areas that, that we're going to be discussing are, you know, kind of defining what it means, uh, to be a fractional CTO or, or CPO. Uh, specifically how, how each role is maybe aligning, uh, engineer and product with key, key business objectives, um, breaking down, uh, like the key stakeholders that, that you all are interacting with and, and also how you integrate with the existing teams. Um, I'd love to understand a little bit more about, you know, what metrics define success. Um, I know Mike's got a slew of other things here, but, um, and then I'd like to also close with just a little bit of like, you know, let's, let's talk about, you know, what we think the fractional market looks like in 2024 and beyond. Um, so the easiest way to kind of kick this off, I think is just. Uh, you know, starting with both, you know, each of you is we'll start with you, Matt, uh, and just from like the fractional CTO point of view, you know, giving us an example or some reasons when and why a founder, you know, loops you, you and you or, or your, your, your counterpart.

Matt Walnock: 00:12:31

Yeah, happy to, um, It's a, there's a range of situations, um, but largely it's to answer the question of why isn't my product what I thought it was going to be. It's, it's a miss in the, you know, the expectation. I work with largely, um, early stage companies. Some of them have just received their funding and they want to be pointing in the right direction. Others are through it and not. Sort of necessarily seeing the results they expected so that they can identify that maybe something's wrong, but the what is actually going on and what is wrong. Um, that's where somebody like myself, having seen a number of teams doing this for the, the last nine years, um, as well as prior experience, can kind of step in and say, all right, let's, let's step back from the whole situation. Let's look at the team and the process and how everything's being decided. And more often than not, it's, it's a, it's a, it's gaps in, in, in that process, either, you know, at the beginning where it's so critical to get requirements well refined and, um, on point, especially when you're in a situation often where the founder is the, uh, the sort of the anchor and the engineering team may be offshore. You know, that translating the founder vision to that engineering team via those requirements is always critical. So that's, that's usually a gap and then kind of the other end, the quality of the operation, and usually it's, it's situations where they've made decisions or had leadership that hadn't had the experience or got caught off guard by some things, or they've had success in a lot of cases, they've had to grow in certain areas and had to leave other others behind for. For the limited resources they've run, but for me, it's, it's largely being able to step in and go, okay, what, what's missing? What, what, what isn't being fully fulfilled here from a software delivery perspective?

Tim Winkler: 00:14:09

Sure. And, and we'll, uh, dissect that more, uh, before I kick over to Dan, though, I do have a quick question on, uh, the bulk of the, um, uh, companies are the founders that you're collaborating with all the bulk of them coming from, you know, more of like a go to market background versus a technical background.

Matt Walnock: 00:14:29

Most of the folks that I work with, yes, um, they're, they're, they're in need of that good technical partner at the beginning. And if there can't be that for themselves, they're, they're often leaning on maybe somebody that can author the code maybe has run a team, but isn't sort of at that level of business acumen to kind of translate what the business needs into the actions the engineering team needs to take. Sure.

Tim Winkler: 00:14:50

Perfect. Uh, and Dan, let's kick it over to you real quick. So, you know, talk, talk to us a little bit more about when and why, you know, you're being brought in, uh, to, uh, uh, to an organization.

Dan Maccarone: 00:15:02

Yeah, I think there are two scenarios that tend to work best for me as a CPO. One is, you know, early stage company. pre launch. Um, they really need to, you have a founder, who's probably a subject matter expert and really knows the problem they want to solve, but may not know how to translate that into an actual experience. And so for me, it's like coming on board, helping, like listening to them, and then working with them and their CTO. And they have another CRO or someone who's part of it. They're going to translate that into an actual overall, like, UX and design, uh, and work with a CTO to get it launched and help, help evolve that product after launch to see what's working, what's not probably also partnering with a marketing person, a road person, uh, with the first, you know, like, uh, 18, 24 months while growing their team. Uh, it's really important as part of the, to me as a fractional CPO to find the right people who can work full time while I'm not there full time. But the reason they want to hire me is because. I bring an expertise with the amount of companies I've helped launch over the past couple of decades to, um, to do things faster and quicker and put a process into place that's going to work for them. The other audience is some, a company doesn't even have to be a startup, but usually it's probably a smaller company that exists, but is, has either gone off the rails or is going in or is going up the rails and really needs to rethink their approach to product and approach this digital strategy. So coming in there often means a few things. And it's kind of similar to something you said, Matt, like. It's reassessing where they're at, you know, what's, what's wrong, what's the problem, what's your North star. And then it's looking at the team and saying, this is not the fun part and saying, who's right for this company? She's not, what do you guys need? What's missing? What's your process? Like, do you need a new process or a process at all? Which often it's the latter it's you have nothing going on and you need to get something in there. Um, and implementing that. And hopefully, you know, you can do that one in like six to eight months. I often find that those are the ones that move faster, but because they have a product that just needs some adjusting. But you still need someone who can come in with an outside eye who's not a consultant. I think that's a really important thing. They're not a consultant. They're part of the team. They're just part of the team that just happens to not work, you know, 40 hours a week, but is doing the work to get the change kind of implemented and get everything on the right track until a new person comes in and fill that full time role. I think

Mike Gruen: 00:17:20

that's an important point that I, that was like one of my questions. I think a lot of people have is how do you differentiate Fractional from other types of whether it's consulting or contracting type work, um, you know, I'll let both of you answer. Um, you know, Dan, if you want to take it first,

Dan Maccarone: 00:17:36

I mean, yeah, Matt, I'm really curious as you've been doing this for as much longer than I have, but the most important thing. But one of the most important things to me is having buy in from that kind of C level, um, or overall C suite, that you are part of the team. And that needs to be communicated to everyone else. If there's not buy in from the top, it does not work in my opinion. Like, like you, because people, I think, if they think you're fractional, think you're not focused. On the product, and I've actually had, I've had founders said to me, if you don't think about this like 60 hours a day, then you don't really know what it's like to be part of this company. And I'm like, well, that's not true. In fact, I think it's good that I'm not thinking about it 60 hours a day. So what I am thinking about it, everything else that's kind of contributed to my thoughts is letting me focus on this. But that, but that buy in is so critical because it is a bit of a controversial space. I mean, Matt, I don't know what you believe in.

Matt Walnock: 00:18:28

Yeah, I mean, when I, when I meet my, my clients for the first time, starting to get their know their teams, I treat it like I'm onboarding as if I were their full time CTO, I have to emote that I have to show the actions I'm taking, I have to kind of start to understand their culture because the first, I mean, the timing you described there, Dan is right on that six to eight month window, but those first 30 days of onboarding and observation, it's not about like, Immediately coming in and making changes and fixing things. It's getting up next to the team and understand how they operate and how they can be changed and what, what's safe to lean on and what's, what's not. And that's to me is the same as if I was joining them full time, I very quickly get into the mode of saying, you know, we have issues and we have challenges. And, you know, the support from the top is, I agree, completely necessary.

Tim Winkler: 00:19:12

And I, and I imagine too, that the level of transparency that the founding team is having with the rest of the team about what's happening here is pretty essential, right? I could feel like if I was an engineer and you know, you're coming in and you're, you know, you're, you're, you're asking questions and everything about, you know, processes and just doing that discovery phase. Um, if I wasn't really, truly clear that, you know, Hey, look, we're, we're bringing in this fractional, you know, resource. I want you to treat them as if, you know, like, you know, is, is our CTO, but just knowing like, this is a fractional individual, like, are you coaching them on how they communicate that to the team or, you know, because you've maybe seen it time and time again, this might be their first engagement with one. So how, how are you all, um, I guess this kind of leads into that next question about like that integration with the team and, you know, what steps are being taken to ensure more of this like seamless kind of process flow for you.

Matt Walnock: 00:20:08

Yeah, I mean, absolutely. It's, it's, it's really important to get that right. The introduction to the team is once you've got the support from the leadership, um, the next right in line is, is the team willing to work with you? So it's, you know, uh, you know, taking up a non threatening posture. I'm here to help. We're going to work together closely and here's what we can achieve together. And it's really sort of selling them as a team that it's worth their time to pay attention to things that I might have to say.

Tim Winkler: 00:20:35

How about

Dan Maccarone: 00:20:36

on

Tim Winkler: 00:20:36

the product side, Dan?

Dan Maccarone: 00:20:37

Yeah, I don't, I don't know that it has to be communicated as this person is fractional. It can be, I think it's, you know, I think it's okay to tell people that, but I also think that they, if you have the support of leadership, it should be, here's our product lead and. You know, for the most part, you're working remotely at this point anyway. So it doesn't, I mean, I don't, I don't devote hours, specific hours to clients. I'm available whenever they need them. I had my, I might be working on something else and they hang me or by working for them, but like. To me it's about, this is the person who's running this, and I'm building a team or working with a team. And so, I don't, I don't like to be thought of as someone who may not be available mentally or physically for someone. I think it's more like, I just happen to be paid fractionally. You know, that's how I look at it. I don't know, I don't know. Matt, can I ask you, like, do you, Do you think that that makes sense or do you think it's important to communicate the practical side? I don't want to hijack your show.

Matt Walnock: 00:21:36

This is what we want. I think it's well, I mean, I have to, it's more getting into the process with them and sort of showing that I'm going to be a partner to their current leadership. Um, engineering, that might be a director. It might be a architect, a team leader of some sort. Cause that's it. It's just important that there's some instant credibility so we can get to work and that that comes from just me working with that leader. And in a lot of cases, that's just what I'm there to do. It's a one on one with that engineering lead. And that's the level of engagement we're at. And then from there, it's me and the team were, you know, a full interim role. Where it's more of what Dan's describing where it's like, okay, you'll report to me now I'm taking the title. It's I would be labeled interim CTO. Not a lot more communication needed other than that. Leadership has support and we go to work. But in those cases where there's, we're looking to keep everybody in place, we're looking to grow and scale and augment this team. Then getting a good partner just at that team level team leadership level is really important. And, and for me, Dan, I I would just finally say that the sort of the boundaries for me are a little bit, I need to make them more clear 'cause I run right into like operational roles and touching production systems and things like that, that I need to be, have bright lines around when I engage.

Tim Winkler: 00:22:54

I was just gonna say, I'd imagine too that, you know, for some of these scenarios there could be, uh, nego an offer to like, hey, like yeah, if it's an interim role, if it goes well and you like this as well, like you could truly become our full-time, CTO, um. So you, you, you don't want to kind of spoil that and just kind of like, maybe just set the stages is like, yeah, you know, here's our, I've been asked

Matt Walnock: 00:23:18

more than once, but I try to go into these things with like, no, let's just think of this as the temporary condition that it's going to be. And we're here to make this a better situation for the next person. And I talk more about how the transition will occur and make sure the client understands what the vision is for this, not get used to me doing this part time for you. I think that's so

Dan Maccarone: 00:23:39

important

Matt Walnock: 00:23:40

because I,

Dan Maccarone: 00:23:40

I definitely have that same position where people have said to me, so I know you're doing the scratching right now, but when are you going to be full time person and it's like, I'm not, that's not what we agreed to. And, and it can become quite frustrating because they're, that means they're not thinking about you in the role that they should be. They're thinking about you as someone who is part time or as a consultant. And that's clearly, you know, not what Matt's doing, not what I'm doing. Um, and when, I think when you start having those questions again and again, you have, you have to ask yourself, is this the right place for me? I don't mean full time. I mean, they're asking you to be full time. I mean, it's a compliment in some ways, but it's also like, guys, you got to know people you're going to know, like, this is not, that's not the.

Matt Walnock: 00:24:23

I mean, I've, I've worked with clients where we had to have that conversation. And it's like, we're, we've, we've done the part where we fix the things and now it's time to move on and get somebody in here and, and we need to wind it down.

Tim Winkler: 00:24:35

Matt, you kind of touched on this briefly, uh, when you're answering the previous question, but you know, what, what does the, uh, snapshot of the engineering team look like when you're stepping into some of these engagements? You mentioned there might be a head of engineering or like a lead engineer or an architect. Uh, what's the What's the common thread that you see in terms of, you know, what that next hierarchy of a, of a tech individual internal looks like.

Matt Walnock: 00:25:03

Um, generally like small team and most recently it's, it's almost always a mix of onshore and outsourced engineers. Um, and the state they're in is usually there's enough process there that it got the attention, it got the funding. And now it's, it's a moment of decision on how to scale it. Is it, you know, bring on more of the outsource team higher locally restructure is the architecture going to support a lot of questions, um, in the air. And when I can start to offer as a sounding board to that, that leader and say, there's here's options, let's talk through options and give them a space where they're not doing that in front of their team or in front of their boss. And we're hashing it out. In the background, building their confidence, and then we help package that up for delivery with the team that gets us into talking about process. So there's, if you kind of aim right at what do you need to deliver? And that could be based on the product vision. It could be based on the road. It could be contracts that they've written and made customer commits. And this, this individual is being told, you know, I need to lead this group forward and grow this product. Usually it's in a moment where they've never had to grow at that rate or in that way before.

Tim Winkler: 00:26:11

Dan, how about yourself on the product side? Are you seeing a product team currently in place traditionally? Or is there no, you know, lack of any sort of a product team?

Dan Maccarone: 00:26:22

For an early

Tim Winkler: 00:26:23

stage startup,

Dan Maccarone: 00:26:23

usually there isn't one. Um, usually I try to, I think that like on the products that you generally you're building a product, you don't need a full time team on day one. I think that you do over time. And so what I try to do is use my network of design and UX resources to, you know, find the right people to start, um, get that product built over, let's say. Somewhere between 8 to 10, 8 to 12 weeks, uh, and then once you launch, you're going to spend some time learning. You can't immediately go into the next sprint because you don't know what's working. So if you had a full time designer sitting there doing nothing, it's kind of a waste of money. But I do think that as you planned out your roadmap and you're looking at things, you know, you start to see where you're going to need that full time designer or full time UX person or. Full time PM, whatever it might be, and you kind of layer them in. And I think by the end of the first year, at that point, you should have a full time person, at least in design, or at least, you know, um, if you're head of product, if you're me and you're head of product, maybe you hire a part time PM or a full time PM, because they can kind of work on the day to day, you know, details of things. Um, but by the time I leave, I, I, I kind of like to have a full suite of product team. Um, ready to go, uh, at larger companies or when I come in kind of mid midway through a company's journey, there usually is, you know, some people are some people on staff and there's probably a reason I brought in some of them are probably not going to stay and some of them are, um, and then it's about building out the right team, uh, filling in the gaps where they exist and, and, uh, and keeping the people who are may may have been like have been hampered down before and have all the talent, but just weren't able to use it. And so giving them an opportunity to. To really discover, you know, themselves and get even better at their job. So, uh, that's a great thing is when you find someone who actually has that talent and you get to bring them up a little bit and get them excited about the job again, I

Mike Gruen: 00:28:16

mean, I think that's one of the things that's really different, like at startups between say engineering and product is like in the early days, startup. Your CEO, the founders, they're the product people, right? And you're probably coming in and really helping them take what that vision and translate it into something. Whereas if you have a technical founder, they're doing the engineering and now it's, it's sort of helping them on the business side of things. Not some, you know, they sort of understand they've been through this, this before they understand like what a good process looks like, but maybe they've never been responsible for it or, or whatever else. I imagine that's a big difference. Um, like with regard to like, Matt, you're pairing, you know, you're working with the engineering leader, whereas, and maybe in talk, I'm sure to the CEO or whoever, but you're a little more focused on the team. Whereas I'm sure Dan, you're probably more working with in that gap between. The CEO and the engineering team and what they probably have a technical founder or CTO or somebody who you're working pretty closely with.

Dan Maccarone: 00:29:16

I think it depends, you know, for me, oftentimes it's helping the founder and this can be in concert with the CTO, by the way, it depends on the company. But like, oftentimes I find that. If I get to have work with a good CTO, it's the CTO and myself educating the founder more than anything else. Um, and that education isn't education around their vision. Obviously they have this idea of what problem they're solving. It's about. Focus. It's about what, like how to prioritize things and how not to try to boil the ocean and, and often how not to take right turns and keep on the path that you've set forward before you even get launched. So that's the biggest thing I always find is you have wonderful founders with great ideas who. You know, hear about something that can make the product even better and immediately want to add that to the roadmap. And you have to be like, look, that impact product that impact engineering and probably impact marketing. Like, yes, let's do that in six months, you know, and so those conversations that no one wants to have, but you got to have are a big part of the job. Um, and it allows, you know, the team designers, I'm sure that's true on the engineering side too, to get their work done and not get distracted by things that are kind of shiny objects, you know, yeah.

Matt Walnock: 00:30:24

Very much so. Yeah. I mean, I often find there's folks that it's an absence of folks like Dan in the role and you're asking the engineering lead to stretch themselves all the way to that CEO's vision and bring back something tangible for those engineers to work on and. I've been asked more often than not. What does a product manager do, Matt? I try to answer that question. I try to demonstrate a few things, but there's very much a gap, especially when the founder is a product center wants to be connected to the customer and the application. It feels like they really want to own that. It's difficult sometimes to say, Hey, you need a partner to just help you refine that before we can even Start building the other. So the other

Dan Maccarone: 00:31:07

thing that's like, I don't know if you see this, but like, I've noticed this more and more and maybe it's just, as I get older or let's say I get more experienced, is that a way of putting it is, uh, that, uh, um, a lot of people are afraid to say no to a CEO. And this is true of big companies as well as companies. And I was just working on a project recently where I was a functional practical CPO, and I was talking to the, one of the marketing people. The CEO had asked for something and she was like, yeah, I got to do that. I'm like, wait, why did, why are we doing this? That makes no sense. And she's like, well, he asked for it. And I was like, it's okay to, it's okay to, you know, uh, question it. Like, just because it's an idea doesn't mean it has to happen. And she's like, well, I don't feel comfortable doing that because, you know, I have many of that long, whatever. And I was like, wow, it really, and I've heard this before and I've seen this before and I'm like, wow, there really, it really does need to be someone there to kind of help the people who can't say no. Maybe we don't feel comfortable or don't feel like it's appropriate or whatever, but you've got to be able to have that conversation and say, listen, Like this needs to be tabled or this isn't right, or let's have a conversation about this. I'm being negative. I don't mean to be negative, but like, I mean, I think

Mike Gruen: 00:32:19

I found when I was, so I was interim VP of product. I've been, you know, whatever. I found my job was more often than not like, yes, but like, and it's back to what I think you were saying before, which is, yeah, that's a great idea. Let's do it in six months or like, here, let me pull off the roadmap and okay, let's work together and figure out where, like, where does this actually line up? Um, and then the CEO is always like, I hate when you do this. I'm like, yeah, Cause you know, we have to prioritize, like, welcome, welcome to the world.

Matt Walnock: 00:32:46

And a lot of times they've been spending those resources in the engineering group without even really how much realizing how much any of it was really costing. So part of this is surfacing, just the velocity, the capacity, the dollars going into that saying, do you really want to spend those dollars this way, or should we focus on the contracts and customers? I mean, opportunity

Mike Gruen: 00:33:04

cost is a huge one that. You have to bring up a lot like, okay, cool, we can do that. But you do realize that that means we're not doing this, this, this, and this. And that means this, you know, all the things that come from that.

Matt Walnock: 00:33:15

So I find there's revelation just in kind of putting all that out on the table in front of them and going, here's value, here's cost next to resources next to the value you're intending to get. And that's what having a partner person, a product person as a partner to do that. It's just, it's night and day and the experience.

Tim Winkler: 00:33:32

What's the average, you know, length of engagement, Matt, that you find yourself in? I know it's kind of a broad question, but, um, you know, you, again, like I think we kind of alluded to this earlier, you know, you, they don't want to be on life support here, fractional life support. So what, what kind of, uh, timelines are you, when you go in and you're scoping something, you know, what are, what are you usually suggesting some examples?

Matt Walnock: 00:33:56

Usually we'll break down something like, you know, that observable observation period, getting to know them as like a 30 day kind of a window. And then we can move into planning and fixing. And that is aligned with what Dan said earlier. It's like a six to eight months before you can really have the impact and be changing, you know, what's going on. But a lot of these have just a very long tail on them. I've been with clients that I still talk to for years and we're in Slack together. And it's more. You know, touch base every quarter type of a scenario, but the, you know, full attention to sort of interim CTO roles. Those are 6 months to 2 a year. And by the time we get to that 3rd quarter, we're, we're both looking at each other going. Okay, let's start putting the process together to do the higher.

Tim Winkler: 00:34:39

From an actual amount of time that you're spending on, uh, the engagement itself, does it, is it like heavy in the front end and then it starts to wean down, uh, as you get further along in the engagement or is it just, you know, part time, like, yeah, I don't know, 20 hours a week or any sort of like, uh, Or do you not even do hourly and just make it about milestones and deliverables? I

Matt Walnock: 00:35:03

try to do just a monthly retainer. So I, similar to what Dan was describing earlier, that I can, I can chop up my day how I need to, to get to, to get to everybody. Um, so I, I do, I mean, I put in a lot of hours, but it's, it's, it's largely based on the style of that engagement. So I'll have like one large one that I'm focused on and then maybe one or two coaching or mentoring type of arrangements, and then some maintenance stuff with folks that I touched with. Touch base with much less frequently in terms of the level of effort. And over the time, it's like getting on board that observability period. That's, that's kind of nice. We're getting to know everybody, but, and then it gets busy and then you're, then you're really cranking on the problem space and you're trying to keep up with a, a fully running team. Um, um, not breaking what they're doing while helping them, you know, turn in the right direction and make some positive change.

Tim Winkler: 00:35:53

So those timelines kind of align with you, Dan, and on your side.

Dan Maccarone: 00:35:58

Yeah. And I try to do one to two kind of bigger clients at a time and then have smaller ones on the side. Uh, my, my timeline generally is, is. I would, I try to do like a 12 month engagement because I do think that once you start seeing results, like Mark was saying, you can spend a lot of time fixing more things and, and seeing, you know, what's working, what's not and hone your strategy. Um, but, you know, I think after like 18 months is my max, you know, my, I mean, my max to say, you got to replace me. Uh, I do love those clients. You stay, you're always kind of. Working with what I often find is that I'll kind of come back and work on smaller projects with them afterwards on things that are much more focused, um, or like little strategy pieces in concert with whoever's running product and marketing like I'm not a marketer, but these are working as well. But I do, and I love those relationships because they can last for years and years and years. But for that, like really heavy lifting piece of it, it's, uh, it's about 12 months digging team. And I think, you know, to Mark's point, like from Matt's point, like, you know, the. The, um, uh, the, the, the first 30 days, by the way, the first 30 days is the happiest time because everyone is like, you know, ah, we're in this together. And then, you know, you start having those harder conversations and, um, which is not a bad thing. It's like, I think it's quite fun to get into like actual strategy and getting that stuff done. But it is like. You know, it's not all lollipops and milkshakes, you know, it is something else, you know, important. Missed an opportunity for, for pairing or tea and cricket. I was going to

Mike Gruen: 00:37:32

go with McDonald's and Krispy Kreme, but it's actually a quarter pounders and Krispy Kreme.

Dan Maccarone: 00:37:38

It's not all quarter pounders and Krispy Kremes. I mean, it could have, it could have been tea and cricket also, I will say not, not you know. I don't know. I don't know.

Tim Winkler: 00:37:51

I'm curious to know, uh, when are the, when are these scenarios where you're turning away the engagement, because I think that's helpful maybe to understand, you know, this good. Personal fit here, the skillset fit. Um, I'd imagine financials have a big part to play into that, but, uh, generally curious, like what are some of the, the immediates that can maybe pop up and you're like, this, this isn't going to be a good, this isn't good for a fractional CTO or fractional product lead.

Dan Maccarone: 00:38:24

Um, I mean, red flags for sure. There's a lot of red flags that come up and it's around, you know, it's our own expectations. It's, I always try to get a good sense of. What is the vision of this person? Not just like, what is their vision for their product, but what are their expectations for the next, you know, six months, 12 months and who else they're going to involve in this experience, right? Like, how have they thought about marketing? How have they thought about technology? You know, um, how did that all revenue? That's a big part of what they're doing because. If they want to, I go back to saying, if they want to blow the ocean and they can't be convinced otherwise, then that's not something I want to be a part of. If they, if they, um, if they think they know more about technology than they do, then I don't want to be involved with them because they're not going to listen. And it's how much they, they actually trust, you know, my experience. And I certainly am not saying that I'm right all the time, because I'm not. Bye. To me, like, I, I believe that the philosophy of trust your generals or lieutenants, like, if ever I figure it's like I come to Matt and say, Matt, let's talk about this and we end up on the same page that we go to a CEO and that CEO has no interest in listening to us because it doesn't align with that person's needs. Like North star, even though like we've done all the research and if that happens once, fair enough, but if it happens like six times and that you can tell this in an early conversation with someone, I don't, there's no point in working with that person. Cause you're never going to be affected whether you're a program or not. But like, to me, I'm working with four or five clients. I'd rather work with four or five clients. We're going to listen to what, not just me, but like the team I bring to the table, you know, has to offer. And they're generally pretty experienced. Um, and it's willing to have that conversation. Not again, to say that we're going to dictate what the right answer is, but at least to be like, Listen to what we're saying, that's my biggest point of playing what they don't want to listen, then I, I know that it's not like,

Mike Gruen: 00:40:14

I think the way I, I phrased that just like, is the idea of like strong opinion, strongly held versus strong opinions, loosely held. I'm fine with somebody who's got strong opinions, loosely held, right? Like, I can change your mind. If you've got strong opinions, strongly held, there's just no point in having this conversation. Right?

Dan Maccarone: 00:40:29

Right. And I think, you know, oftentimes that happens. I like to do a small project with someone first to just the appearance alignment. Right. And sometimes that's a lot of research. And if I come back with research, the data that says something that either agrees with what they're saying, or it's slightly off, or maybe totally is like, yeah, he's actually over here and there, and there is no listening to that. That's a big, big red flag. It's like, you're not going to listen to the data. If you don't listen to data, then what are we here?

Tim Winkler: 00:40:58

Matt, how about yourself? And maybe also another thing to really add on there is like, you know, the, the stage of the products and, um, you know, when, when is it too soon for you?

Matt Walnock: 00:41:07

I mean, I don't not, not to be repetitive, but the receptivity to what you're saying and how you're coming to these conclusions. I mean, it's not, you have to show your work. You have to convince and support and put the, put the data behind it. But if you don't have a receptive audience, you're not going to get very far. Um, you know, other things that, that come to the top of the list on the engineering side, I start to look at compliance. Um, I start to look at obligations. They've got outstanding and their ability to meet them with the tech they've got deployed. Yeah. Um, we start to look at how they're handling their data. It just, you start to get into some very sensitive things very quickly, depending on which vertical they're in. Um, and, and sometimes I've been, you know, revealing things to leadership. They didn't know we're there, which is an interesting situation to find yourself in. Um, But for the most part, it's all, it's all just trying to get transparency to what is being run, how it's being operated in a, in a space where you, the leadership can see it, start making decisions. Um, so it's, it's just, if you're not able to kind of surface that in a way that they can understand, that's the other thing is if you're dealing with a non technical COVID, sometimes it's really have to put this into a space where you're, you're literally at the whiteboard for a few hours, just breaking it all down and trying to show dependencies between Decisions, um, can kind of blow their hair back from time to time when, when, when you get there, but again, if you can, if you can synthesize and here's what we can do about it, which is your real value for being there, then sort of the shoulders come down the street. You can see the stress kind of come off of them and like, okay, we can do something about all of this. That's great. Let's go.

Tim Winkler: 00:42:43

What about product stage? Like, uh, I'm just generally curious, like, are you, when are you coming in? Or it's like, um, What, like when's the earliest that you've, you've kind of come into

Matt Walnock: 00:42:52

an engagement? Um, well, I mean, the absolute earliest was, you know, it was, it was a founder and a developer. That was a very good idea too. They needed some, yeah, no, but the more, the more typical is, um, yeah, they're, they're in that, you know. Early stage money, series a, maybe I've worked with a couple of companies that were, you know, 250 to 500 million in revenue, but that's few and far between. Most of them are much, much, much smaller. I, I like to just get it. And again, when I walk in there, it's not about, you know, I'm here to do a job for you. It's, it's more, I'm here to help you over a period of time in your existence and what's the right level of attention and detail and what's the process. So. I'll talk to anybody having to meet them. And a lot of times it's, it's handing them off to maybe to somebody like Dan to say, Hey, you don't need me yet. You need somebody like that to kind of get your roadmap put together, get the vision, go figure out if the market is even receptive before you start spending engineering dollars.

Mike Gruen: 00:43:56

How much time do you think you guys are spending educating your perspective client on what fractional means and what they're actually getting or by the time you're having, or they've already sought you out and maybe they know what they're, they know what fractional means. And so maybe you're not doing that education because I've talked to a lot of different people in the space and. There's varying, uh, amounts of education from their perspective.

Dan Maccarone: 00:44:18

It's a lot up front. It's a lot up front. I mean, at least for me, I mean, I still think that it goes back to people not understanding the difference between a consultant and a fractional person. Uh, and, and even if you explain it to them, I think there's often this skepticism of, but are you really a part of the team? Um, and I work with so many early stage companies that I think that it's not just explaining to them, but it's convincing them and their investors. You know, their investors are often skeptical that they can't get a good product to the market with someone who's fractional. And you know, as someone who ran, I ran agencies for 16 years where we were doing the exact same thing. We just had a team. We thought of our team as our team, the product, even the box, even getting agent, um, investors on board with hiring. An agency that could actually get the thing launched faster than trying to hire a team internally was a challenge until we had until we could prove it. We proved we have four problems and look at all these things we've launched that have actually been successful with our work. But I'm a fraction of the same challenge. It's like. You have, but in the end, like, Matt, I'm sure you've had this experience more than me. It's, you gotta, it's asking them to have faith in T'Challa. Either they're gonna trust the idea or they're not. And there's not so much education as um, understanding and faith.

Matt Walnock: 00:45:39

Yeah, I agree with that. It is. It is a lot of upfront education, but I find that once we get started, once there's action being taken, results being shown that we don't talk about it much anymore, I tend to from time to time, I mean, it does come up in like the hours that we're working. Like, I'm not going to be available afternoons in some case, but for the most part, it's, they don't really see me as fractional once we start working together. Um, and, and I have to sometimes remind them to go, yeah, I have another client that I'm doing a thing for. I'll see you in a week. And yeah, yeah. Yeah. It tends to just fade into the background.

Mike Gruen: 00:46:10

Yeah, I figured. But I mean, like at the, at the very beginning, like when you're first starting setting up that engagement, the sense I'm getting is that they really don't know what you are doing a lot upfront in terms of education on what this role looks like. It's not a well enough known. It's not like, I feel like people understand like a fractional CFO very well. And at this point, like they would seek that out and they wouldn't have in their head, they wouldn't need to be educated about what that kind of means.

Matt Walnock: 00:46:38

I just try to not keep the label on it for too long and just quickly get to thank you for introducing me to your team. I'm going to work with this named individual on these sets of things and your team will see this. And this is the bubble we call fractional CTO for you. And once they can understand what to expect, it goes a long way. And again, the label just sort of goes away. It's now Matt's working with the engineering team and we're going to do good things together. Awesome.

Tim Winkler: 00:47:04

And to counter that too, I think, you know, this leads into another, the kind of like last question, um, on the topic, but they've probably done some research to get referred to you to this point. Um, I, I, I. Mike and I were talking about this about like, you know, how, how are you, how are you sourcing, you know, new work? Right. And I've always seen that it's usually very, very much. It's just a referral network, right? You did something for this person over here. They know another founder over there that's in a similar type of, um, debacle. And they're like, Oh, I used Matt. How, how are you sourcing your, your, your opportunities? Uh, or are there other outlets out there that maybe folks aren't privy to? And, um, you know, You can keep it secret if you want to keep that resource a little golden nugget to yourself, but I'm curious.

Dan Maccarone: 00:47:58

I mean, I, my whole business, my entire career has been through word of mouth and through referrals. Uh, I don't do any marketing or advertising other than stuff like this or my own podcast. But even that is generally like about kind of a layer upon a layer. And so there's always, I would say 95 percent of the time it's, I have a contextual warm introduction or referral. Um, and I like it that way. Uh, I find it so hard to. Convince someone who's never heard of fractional or doesn't trust consultants or whatever, um, again, different things, uh, to, to persuade them, I mean, even with a portfolio that I have, which I'm very proud of, but. Um, yeah, that's, that's how I've always done business. I've never done any sort of, um, marketing. So you don't

Mike Gruen: 00:48:44

have like a big LinkedIn campaign reaching out to, no,

Dan Maccarone: 00:48:49

no, no, I would, I would, I don't, I, that makes me like want to throw up like the idea of doing people do it. I, I LinkedIn's huge. I, I, I don't even like, I don't even like putting job postings on LinkedIn for people I want to hire because you just get a, just a sea of people, like a fire hose of people so far fast. And you're like, well, I can't do these. So I tend to like use the same thing when I'm looking for someone, I do it in my network and I'm like, who's going to be great at this? And I get three or four people. And usually one of them is that diamond in the rough you're looking for.

Matt Walnock: 00:49:22

That's been my experience too. It's a lot of, a lot of warm leads and doing good work for folks and your name gets around and then you get some, you know, you're, you're walking in with credibility, having done good work for folks. And

Tim Winkler: 00:49:33

have you guys seen an uptick in, uh, inbounds, uh, in the last year and a half

Matt Walnock: 00:49:38

or two? A lot more receptivity to it. Yes. I think it's, they've been asked to talk to a lot more folks and introduced to a lot more companies in the last couple of years. Yeah, definitely.

Dan Maccarone: 00:49:51

Yeah, I think that's right. I think it's, it's more that the idea that people are actually. Considering fractional people versus not, um, and I certainly think that there are rules that they're considering fractional and rules are not as well. Like, they're like, definitely, um, I see a lot more fractional CMOs and I see CBOs, for example, um, but I think that just means we're at the beginning of this kind of, for lack of a better word, movement, um, I

Tim Winkler: 00:50:19

think paired with a pretty drastic change in venture funding, uh, no doubt. And a bit in a tighter grasp on, uh, you know, budgets, uh, has certainly, you know, created a wave of things, one, uh, a downtick and hiring up larger engineering teams that maybe wants. Would have done to more folks offshoring or outsourcing development, and then three more, more engagement with consulting or fractional types of, uh, resources. I've seen that across the board. I don't know if that's been some of the themes that you all have seen, you know, as you're. Building your teams, if they're, you know, are they less has you maybe maybe it's still too soon. But have you seen a shift of folks maybe wanting to come off of outsource development or staying on the path of outsource development? Because, you know, for financial reasons or anything like that.

Matt Walnock: 00:51:17

I don't think that's changed a lot for the companies that I work with. It's always had an outsourced component. Most of them do. Um, I have seen, um, uh, interestingly enough with, um, AI, I get a lot of folks now wanting to have those conversations, um, even if their product wasn't necessarily pointed in that direction. Um, so we start talking about growing the team. Where do those skill sets come from? But it's much more specialized than it is. I need a front end developer, back end developer. Yeah.

Dan Maccarone: 00:51:48

Yeah. And the product that it's not the same thing. I mean, at least I still see where you're saying that, which is the outsourced. Dev team, but when it comes to designing UX, I don't usually as one person that is somewhere domestic, doesn't have to be in New York where I am. But, um, yeah, I don't, we haven't, we haven't really outsourced that and I don't think ever really.

Tim Winkler: 00:52:08

Yeah. I've seen downtick in, in product roles. Um, as far as like, you know, we used to see a lot more of them, uh, those product teams kind of being a little bit more trimmed down, uh, you know, Across some of the series, a series B startups. Um, but again, I think there's a lot of that's just an aftermath of overhiring, uh, from 2021 and just a different economic time as well. As far as I think it's awesome because

Mike Gruen: 00:52:36

you have trimmed down engineering teams. I mean, it's one of those things where there's a ratio of the number of people. Engineers and the number of product managers and if you're trimming down the engineering side, you probably don't need as many product people.

Dan Maccarone: 00:52:50

Yeah. I mean, you don't need, I think that the number of people to make a good product team, isn't a lot, especially for a startup, even in a series, they're like, you just don't need that many designers or UX people or PMs. Like, you know, I mean, as you get bigger, for sure, as you have different protocols, whatever, have them PM. So that makes sense. But like you can survive as a startup to a certain extent with like one designer, one UX person. Maybe not even one full time UX person for a long time. Um, and when you add that second designer, you better be hoping you have a lot of work for them. It's like, you know, I mean, the way I was hiring, I'm sure this is not like a new idea. It's like, you want that person to be personally at the seams so that when you hire that next person, there is that, that need for that. Right. Not that I want to, I never want to overwork people. I believe in work life balance. I actually hate companies that don't, it makes me angry, but I do believe that you need to like, Be smart about hiring and not waste money. And when people are sitting there doing nothing, it's, it's pretty, it's, it's a lane for everyone. Cause they get bored too. You don't want your team being bored.

Mike Gruen: 00:53:52

You know, I, uh, you can definitely survive a long time with a very thin product team. Um, you have the right senior engineers in place. They can do a lot of that translation. Um, They take on a lot of ownership. I totally agree. Like the, some of the worst places I've worked have way too many product people and not enough engineers. Um, just, we spent a lot of time talking about the work that we could be doing, or we could do the work.

Tim Winkler: 00:54:21

Well, I know that we've got a couple of minutes left, so, um, Mike, did anything else you wanted to add? Uh, yeah, I think we covered quite a bit. That was really, really informative and, uh, you know, really helpful stuff. So appreciate you guys shedding light on it. Let's, let's transition to a, to our final segment, the five second scramble. So just a quick kind of rapid fire on, uh, some Q and a some business, some personal, um, Mike, you, you lead us off, uh, with Dan and then Matt, I'll, I'll jump off, jump with you. So,

Mike Gruen: 00:54:51

yeah, so let's do this. Yeah, let's do it. You ready? All right. Here we go. All right. Uh, explain fractional leadership as if I were a five year old.

Dan Maccarone: 00:55:01

So, you know how you have a teacher that comes to your school every day and you have to spend time with that teacher? Well, imagine if that teacher had to teach multiple students at once, but it was individually. So they teach you, they teach your friend, they teach your other friend, but they're going to spend. Three hours a day with each of you, but every single day you get to spend time with that teacher and ask them anything you want and you get their full attention for that time period and the next day and the next day. That's what I do, but with companies,

Mike Gruen: 00:55:30

that's awesome. Although I don't think you get three hours cause there's 30 kids in the class, but

Dan Maccarone: 00:55:36

it's a private Montessori school. Practically cheap, man.

Mike Gruen: 00:55:45

What, what's your favorite stage company to work with?

Dan Maccarone: 00:55:48

Great. Uh, early stage. I love, I love pre product to, uh, to, to taking a idea from nothing and bringing it to something.

Mike Gruen: 00:55:55

Uh, what's the biggest challenge or what do you think is the biggest challenge facing tech exec leaders in 2024

Dan Maccarone: 00:56:03

in general tech exec leaders? Uh, I think it's, I think it's marrying the. The vision you're trying to create to an actual product that's going to resonate with users because there's so much out there right now overwhelming people with tech. And I don't care what industry it is. If you look at AI as just one example, like everyone's launching an AI company. So why does yours matter? And I think the question that someone always has to ask is why does this matter? What am I solving? And why does someone want to use this versus something else? And every leader needs to be asking that question. Otherwise they shouldn't be doing the job. Absolutely.

Mike Gruen: 00:56:40

Um, what's the best piece of advice you've ever been given?

Dan Maccarone: 00:56:44

Best piece of advice I've ever been given is, uh, it might sound silly, but it's, is this the hill you want to die on? Meaning, what fights are you, what fights do you feel are worth fighting, and what fights are not? Because we have them every single day, and it's made me smarter about how I approach conversations. And where I will fight and I will fight, um, for things and where it's like, you know what? Let's just let this, let's just go.

Mike Gruen: 00:57:11

Uh, what book should every entrepreneur read? Mine.

Dan Maccarone: 00:57:19

Go

Tim Winkler: 00:57:19

ahead and plug it. Shameless plug.

Dan Maccarone: 00:57:22

I'll give you two actually. So my book is called The Marshall MBA. It's on Audible about how Running bars and running startups are very parallel and all the mistakes I've made in bars much faster. But I actually think that, um, there are a couple of, I mean, re is it, um, reboot, uh, rework, rework as a, as a fantastic book that everyone should read. And if you're in the startup or your world, you should read venture deals to understand how venture capital works. I mean, those two, I think, and, and, uh, the last one I would say is don't make me think, which I think is a really important brand new one who brand and, um, in UX.

Mike Gruen: 00:57:53

Awesome. All right. Um, Would you rather be able to run 300 miles an hour or fly three miles per hour?

Dan Maccarone: 00:58:03

Uh, well, I guess from a carbon footprint standpoint, I'd probably rather run faster like the flash than Uh, live for the ridiculously stupid reason. I mean, this is like a superpower,

Mike Gruen: 00:58:16

just you personal superpower.

Dan Maccarone: 00:58:18

No, I get it. I still feel like I have a carbon footprint footprint.

Mike Gruen: 00:58:23

Mike doesn't care about the environment. I don't care about the environment.

Dan Maccarone: 00:58:26

Also, I'm a runner. So I really, I love running.

Mike Gruen: 00:58:30

Uh, what's the largest land animal you think you could take in a street fight? No weapons. Just you and the animal.

Dan Maccarone: 00:58:37

A land animal? I mean, the smaller ones are actually pretty scary too. Uh, I would say, um, like, like an emu, maybe, um, a llama. Like a llama, pretty good. I got, I got lemma. I'd fucking crush it.

Tim Winkler: 00:58:53

Destroy it. Oh, we can cuss on this. It doesn't matter. You'd fucking destroy a llama. I'd like to see that.

Dan Maccarone: 00:59:00

Hang the llama in my, above my mantle and be like, yeah, my hands. Just standing there eating some grass. Just cold cocked them. Got it. Yeah.

Mike Gruen: 00:59:13

All right. Uh, So, uh, what happened to your, uh, sketch comedy career?

Dan Maccarone: 00:59:20

Uh, good question. Um, we went off Broadway had an off Broadway show that, uh, led to a pilot that we shot. Um, And by the time we shot the pilot, we were, five of us, we were writing, producing, directing everything, and we really burnt out, and I actually, at the time, had just launched, uh, Hulu, and was redesigning the Wall Street Journal, and I had to make a choice in my career, am I going to go down the comedy career route, which, you know, was fun, but, uh, didn't pay me any money, or that much money, and I had launched what became a career for me. Bubble launching thing. And I was like, well, I think there'll be another way to do this. And later on, I got to work with SNL, uh, helping them rethink all their digital strategy, which led to the best meeting I've ever had in my life, where Lorne Michaels leaned across the desk to me and said, Dan, what should I do with my show? And as a sketch comedy fan and performer, to have Lorne Michaels ask you that question, like, there's no better thing that could ever happen. I think I left it exactly where I needed to be.

Mike Gruen: 01:00:23

That's awesome. Um, so what's a, uh, charity or corporate philanthropy that's near and dear to you?

Dan Maccarone: 01:00:32

Well, I, in terms of like causes that are important to me, I am a big, uh, proponent of things that encourage, uh, or are like helping the obesity and childhood obesity. Um, so anything I can ever do around that I, I tend to do, that's probably my biggest, my biggest cause.

Mike Gruen: 01:00:51

And last one, uh, if you could live in any fictional universe, which would you choose?

Dan Maccarone: 01:00:56

Oh man, that's a, that's a really tough one.

Mike Gruen: 01:00:59

I

Dan Maccarone: 01:00:59

mean, I probably, this is probably lame, but I probably would go to like Harry Potter, hands down. All right. Awesome. All the, all the bad shit aside, not like, Well, I mean, the downside is your muggle. So You didn't say that I had to Tea. Kidding. I could be a wizard. I don't wanna be a muggle in a Harry Potter world. That sounds not fun at all.

Tim Winkler: 01:01:24

play tea and cribbage all day. That's right. Exactly.

Dan Maccarone: 01:01:28

Perfect. You could be a Harry. I could be a wizarding F1 driver tell you that.

Tim Winkler: 01:01:38

All right. Well done. Good stuff. All right, Matt. You're up buddy. Ready? All right. Let's go. All right. Uh, what is your favorite stage of startup to work with?

Matt Walnock: 01:01:48

Uh, early stage. I enjoy the, the, the, the early ideation. Yeah.

Tim Winkler: 01:01:53

What's the biggest pain point facing startup founders in 2024?

Matt Walnock: 01:01:59

Um, not to parrot too much, but I mean, I would agree with Dan. It's an onslaught of decisions that need to be made now. And competition is, is claiming all sorts of capabilities. They didn't before and determining what's real and what's not and how to focus is a huge challenge.

Tim Winkler: 01:02:14

What would you say are the top two areas that you add the most value for your customers?

Matt Walnock: 01:02:22

Um, I would say, um, giving them clarity into how their, their software is being produced, showing them the cost and the utilization of the resources they've put out there and explaining the tech, um, being able to kind of translate in both directions, um, for, for that founder.

Tim Winkler: 01:02:44

Aside from AI, what's an area of tech that you are most excited to see evolve in the next five years?

Matt Walnock: 01:02:50

Ooh, um, well, it kind of goes hand in hand, but I think, you know, the, the robots are, are coming hopefully to help. Aren't you optimistic? Agriculture delivery. I know. I like to think maybe they'll grow the food instead of us being the food, but we'll see.

Tim Winkler: 01:03:12

If you were going to offshore development, what country would you target?

Matt Walnock: 01:03:21

Oh, that's it. That's a great question. Um, it, it, it depends somewhat on the culture and the operating model of the, the client and largely that's to do with time zones and how we're communicating with each other. Um, but I've, I've worked with great folks all over the globe. Um, Costa Rica, India, Germany, Romania, um, few in Israel. So it's, it's, yeah, I've kind of covered the globe,

Tim Winkler: 01:03:48

uh, yeah. What is, uh, sorry, but if what's your airport beverage of choice?

Matt Walnock: 01:03:57

Oh, um, let's see. Not caffeine. It's usually just straight water. Just trying to keep it easy.

Tim Winkler: 01:04:08

Not too

Matt Walnock: 01:04:08

dangerous to travel with.

Tim Winkler: 01:04:12

No, no, no. Like a alcoholic choice.

Matt Walnock: 01:04:15

No, no, no. I've just seen that go south for too many people too often. I don't even want to bother with it. Sounds like a story for another day. No, it's about it. Maybe a Tylenol PM. That's

Tim Winkler: 01:04:28

about it. What is a charity or corporate philanthropy that's near and dear to you?

Matt Walnock: 01:04:33

Um, I, I work with donate to food banks here locally in Prince William County and DC. I think just food security for, for people is just critical. Can't operate without it. I mean, second housing comes right after that, but I focus on food.

Tim Winkler: 01:04:51

Nice. If you could have dinner with any tech icon, past or present, who would it?

Matt Walnock: 01:04:56

Oh, wow. Um, Oh, not really. I'm going to change the question just slightly, but I would love to meet Nikola Tesla. I would have loved to just hang out with that guy for a while. I feel like he's a tech guy. I don't get up to Wycliffe and be part of that experience for the time he was there. That would have been, that would have been cool. Yeah. That's cool. Good answer. Good answer.

Tim Winkler: 01:05:21

What is the worst fashion trend that you've ever followed?

Matt Walnock: 01:05:25

Oh, oh man. Do you remember jams? You know, you're too young for any of that. I'm not oldest one here. I know what they're, I

Mike Gruen: 01:05:33

think you're giving me credit, but, uh, describe I remember them very well, unfortunately.

Matt Walnock: 01:05:36

Well, I mean, we're, we're, we're into nostalgia. We're into making eighties movies, so imagine like how we now caricature the eighties into these brightly neon colors and patterns and everything. And you're making below the knee shorts. Yeah. Um. Sort of high print cargo fashion. It was a rough childhood.

Tim Winkler: 01:05:58

That's great. Uh, all right. Last question. What was your dream job as a kid?

Matt Walnock: 01:06:05

Oh, it's, I mean, it's, it's kind of a funny story. Um, I, I was tasked in middle school with writing a, you know, what are you going to do with when, when you grow up? And I wrote a very detailed three page paper about how I was going to graduate from college and go to work for IBM and write software, and I was going to have a. And I graduated from Penn state and I went to North Carolina and I worked for IBM for not, not my entire career, but for the first handful of years. That's kind of was one of the fortunate ones that knew what I was after pretty early. I just fell in love with software development, writing code, used to copy it out of the back of the magazines. So that would take me. It hit me early.

Tim Winkler: 01:06:40

Called your shot. Nice and solid. Cool. All right. That's a wrap guys. Thank you both so much for spending time with us and sharing your knowledge in the fractional leadership space. Uh, it's been a awesome episode and thanks for joining us on the pod. Thanks for having us. Thank you

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guys.