00:00.66
David
Welcome to the superstru show the podcast for founders who depend on devs to get things done I'm your host David Guppman today I'm joined by Rob Mcgray rob welcome to the show.

00:11.34
Rob M
Thank you David happy to be here on the superstruct show I'm not sure if you're going to if you're recording these in order. but I but I am definitely excited to to be in this first season.

00:24.32
David
Yeah, awesome. So for folks who are just meeting you for the first time could you share a little bit about who you are and what you do.

00:33.99
Rob M
Absolutely um I'm located in Los Angeles California I have a hard time calling myself this but but I guess I am an entrepreneur. Yeah yeah, I so sounds so weird. Um I've been a part of.

00:42.15
David
You are definitely an entrepreneur.

00:50.22
Rob M
A handful of startups. Um and kind of had the full gambit of of you know, Success failure success failure failure failure um like everybody else who's who's yeah, who's in the game. Um, you know I've been around for for probably.

01:00.29
David
Sounds like an entrepreneur.

01:08.17
Rob M
But 25 years I've been doing this and picked up some some lessons or some some wisdom possibly along the way and always happy to share my experiences and you know, kind of my playbook.

01:23.43
David
Awesome! So ah, getting into it What kinds of things have you needed to build for your many companies like what's an example of ah of something that you needed a team of people to build.

01:33.58
Rob M
Yeah I mean I tend to tell to tell that that part of the story begins probably with a company called revver back in around 209006 it was an ah early video sharing company kind of launched when Youtube and Vimeo and. Blip Tv and all these others kind of hit the scene and you know it was ah it was an interesting endeavor. It was a video sharing platform with a revenue model of you know wow and we we had we had to yeah yeah, yeah, but we had to build a video sharing platform. Um.

02:03.15
David
I Took a while for that to to catch on.

02:12.50
Rob M
And and at that time it wasn't necessarily ah you you didn't go to adws for it. It didn't exist. Um, you know we now we had to build in the the logic um for the ad serving technology so that we could We could make money.

02:17.79
David
Yeah, there wasn't really like an off the shef here by your video platform.

02:31.35
Rob M
Ah, and and we also decided that we would um, essentially put out an api so that others who wanted to have video sites could basically use our platform as a backend to serve those videos. And make money off any any views that they were getting on their own sites.

02:50.10
David
Well yeah, pretty pretty ahead at the times. Um, so how did you? How did you approach building This did you you put together a team. Ah for this where did you find them.

02:59.43
Rob M
This is this is one of these weird situations where you know I come in a little bit late. Um I do some advising for the company they launch they end up on. You know the the front page of what was it at the time.

03:11.53
David
Dig.

03:14.61
Rob M
It wasn't it was one of those right? There's dig. There's news dot com um, you know? yeah they they they end up on on the front page of one of them and the site just falls to its kneeeze and and then you get the phone call. You know like.

03:16.81
David
Slash dot.

03:29.82
David
Um, you say you got the hug of death.

03:31.48
Rob M
Yeah, hey can you come in and and help us with this and you know you go in and the first thing you realize is that you know it's sitting on um, a server somewhere a friend of mine had a hosting company. It was sitting there it you know it had been configured with essentially just a bunch of disks. There's no redundancy. There's like a lynxys. Um, you know switch that maybe even hub that you could buy at best buy sitting in front of this thing and and then you're wondering why why it all fell down. Um, you know the the same machine that's running you know serving it up is also got you know some kind of postgres database on it and it's just.

03:52.58
David
Easy.

04:10.30
Rob M
It's It's just kind of you know, not ready for yeah, it wasn't yeah it was it was it was having a hard time and you know the company I think basically had made a platform choice out of.

04:12.21
David
Wasn't meant to handle like everybody all at once? yeah.

04:25.91
Rob M
You know the fact that the developer they found knew the platform and they had found this guy. He was located in Poland and he was a real you know advocate for twisted python and he had built the whole thing and twisted himself like 1 guy.

04:33.75
David
Um, me.

04:39.70
David
So was he he was he the like the first developer like someone found him or knew him or something like that.

04:45.19
Rob M
Some some I think somebody found him on you know, like a forum somewhere and and he was the first one there and and he had done Essentially what I would call like the prototype which was now the thing that was out there in the public.

05:01.70
David
E.

05:03.74
Rob M
And we had to quickly staff up with developers who had some of these um skills this original developer was quick to kind of drop off the face of the planet. The minute that this thing got some traffic he became harder and harder to locate. And there there were it was just one of those situations. Um, where you were being held hostage by by somebody. Um and by a platform that you might not have chosen to begin with? Yeah, yeah, and it was it was um, it was very.

05:28.19
David
Wolf is just gives me a knot in my stomach just hearing that that phrase.

05:39.92
Rob M
Was a very precarious situation and it was not one that that I felt comfortable in and I don't recommend and the first thing we did was we found as many developers who knew the technology as we could yeah.

05:50.59
David
So there so you were really just trying to eliminate that single point of failure risk with that one developer.

05:58.10
Rob M
Exactly like that's the first thing that's the only thing we could do to begin was okay, let's get some other people involved who can first of all, let's validate like did this guy is this even good like why is it having so many problems besides just pure infrastructure negligence.

06:02.16
David
E e.

06:08.70
David
E he. Yeah I mean I Yeah I think I think that is just I hope people understand that that's super important but you just you should never fly in a plane with just one engine.

06:16.15
Rob M
And.

06:25.90
Rob M
No no and and you know the the infrastructure was easy to to quickly. Um fix and then you realize oh that wasn't that wasn't the only problem here like this thing has has been arced.

06:36.14
David
E.

06:40.49
Rob M
The the architecture of this application is is not good and you know this was built for like 2 people not not 2000000 and there's no way there's there's no way.

06:42.40
David
Easy.

06:50.14
David
Ah, so yeah, so so you called it a prototype and not like an Mvp. So I guess this was not actually viable at this stage.

06:56.22
Rob M
Um, um, I'm sure to you know just to be to be very Frank I'm sure to some investor who saw it you know under 0 stress. It was at an Mvp you know here's like ah you know Mvp's to me are like.

07:01.64
David
E.

07:06.93
David
Easy easy.

07:14.83
Rob M
Proving that you can build something crappy. Um, yeah, it's like hey yeah we can build something crappy and and hey we'll even put it out to the public so they can experience something crappy and maybe that will make you convinced that we can create something amazing and and the logic I don't follow the logic.

07:15.21
David
Okay.

07:28.69
David
E is he.

07:33.54
Rob M
I just don't it's like you know it it just because I can like draw a stick figure doesn't mean that I can you know paint the Mona Lisa and yeah yeah, yeah, yeah, because it looks like a person see that's a head um and and so it's it's really.

07:39.80
David
I mean but it's on the way like I can I can extrapolate right.

07:51.68
Rob M
You know the the company found itself in one of these situations which a lot of companies do and I'm not faulting anybody it happens. Um where you know you essentially have $5 and you build something for $5 and you get something that is worth $5 you know

08:07.87
David
And and and your mind was there a different way of doing it like the if if it wasn't built that way and it took longer to get something more stable.

08:11.36
Rob M
I mean I mean it's it's.

08:25.80
David
It would have been worth waiting before getting it out in front of whatever hug of death site that brought all the traffic like would it. It had been better to wait and make a better first impression or was this just.

08:41.45
Rob M
I think I think I think that at that time and and possibly still today in some ways that there's this you know formula that has presented itself which is you know you you come up with a.

08:43.36
David
I Guess looking back fine.

09:00.90
Rob M
An idea or a dac and then you you build? Ah ah some version of this I'll call it a prototype and you get some user feedback and the type of user feedback that you know 1 might think is the best type is. The general public aka the world and you know I mean essentially yeah, you got some press and and and I think that that's that's probably what the company was most appreciative of was hey we can send this.

09:21.65
David
E.

09:37.10
Rob M
You know Tech crunch or whatever it is link to our investors or our desired investors and look. We're making Headway like we're we're making stuff. Yeah, yeah, look like we're doing it and you know and and and hope that the fact that it falls down when that investor clicks on the link um can be forgiven.

09:42.24
David
Progress.

09:56.88
Rob M
You know you know I think it would be a much probably a better idea to you know, create something closed if it was a prototype and it was and say hey why don't you guys come and we need everybody all of our friends and our network and potential investors and angels come on in and upload some video and. You know, let's let's kind of see what happens before we launch it out to everybody. Yeah, like like give it ah give it a test I mean I mean you got to remember like ah and this story goes back like almost twenty years and you know how was.

10:17.68
David
Like ramp up a little bit more slowly so that the problems happen one at a time or not all at once or something.

10:35.25
Rob M
At Scale How is a company going to moderate the video that was being uploaded if it were if they were paying for um, ads being served doesn't the company have to prove that the that the person who uploaded it owns it like there are a lot of unanswered questions to just go blazing out into the world with an idea.

10:46.33
David
Easy.

10:52.83
David
In here.

10:55.10
Rob M
Right? But but at that time and it wasn't just revver. It was everybody you you definitely were in a position to ask for for forgiveness later I mean Youtube their strategy was and in some ways still may be just put whatever here like just put it up. You know the more content we have the the better it is the more the more clicks we're going to get the more videos we're going to serve the more perceived value. We've created and that strategy actually worked. You know I mean.

11:23.92
David
I mean but it must have been I can't remember the timeline of Youtube but that must have been like a gigantic loss leader right? I mean that just was ludicrously expensive for them to to do that then to eventually try and turn it around.

11:31.73
Rob M
Oh yeah, yeah.

11:39.83
Rob M
No I mean at that time whether it's Youtube or anybody else like you know their their bandwidth is very expensive. Infrastructure is very expensive. You know everybody's fighting over I mean here in la it was like how close to 1 wilshire. Can you get you know and and.

11:54.11
David
Easy.

11:58.22
Rob M
That premium bandwidth that that tier one was was not cheap, right? and a lot of companies. This was you couldn't go like be like oh I want to load balance this stuff and I'm going to go like figure out a way to kind of do the cheap version of cloudflare or whatever it is like that that stuff didn't. It. It wasn't out there I think um, what is it Akamai was was the big cache like dumb cash provider right? And so cdns were kind of a thing but like just updating the cddn was was its own issue. You know like none of this stuff was.

12:20.69
David
Big Cdn. Yeah.

12:32.31
David
Easy easy.

12:37.36
Rob M
Like sophisticated the way it is now the tools didn't exist.

12:38.53
David
So at this time. Yeah, so so would you consider that that it was a much bigger ops issue at this time than a than a development issue or or no it was just both.

12:49.31
Rob M
Well I think you know historically I think a lot of developers had to have a certain level of of you know systems administration knowledge they they had to know the Os they had to know their way around.

13:03.76
David
Um, yeah, that's true. It's it's a lot more specialized these days.

13:07.87
Rob M
Um, yeah, and so and and you didn't have like big devops teams I mean I was the devops guy at at Revver for a while and you know and I was the cto and I'm I'm no I'm not a very good devops guy you know until we reached the point where we realized. We need to hire somebody who knows what they're doing and that and that guy immediately came in and said you got to move this over here. We're going to host it somewhere else. We need to buy. We need to spend a few hundred thousand dollars on servers or else. This isn't going to work.

13:38.35
David
I was going to say did you did you do it was that the good was that the plan like that workout.

13:41.87
Rob M
You know? but and that's a tough pill for a startup like wait. What? Yeah yeah, we did it. We did it. We moved everything out of um, you know this this smaller hosting company. Um, who had who were perfectly good if if what you were doing was not. Like like massive video sharing. Yeah, but if you were server up webpages over php with like a mysql backend Probably you could do that all day long. But you're serving up like you know you know I don't know how many but let's say you know hundreds and hundreds of gigabytes at that time.

14:01.36
David
Trying to be Youtube yeah.

14:09.59
David
Here he.

14:20.30
Rob M
Um, an hour like it gets expensive. You need to go out and you need to negotiate better rates on the bandwidth and you need to be able to commit. You need to have some idea of how much Bandwidth you need. It was a very different type of exercise.

14:24.10
David
He.

14:31.46
David
Yeah, was that something that you felt like you could have done or should have done sooner that that upfront investment that hiring that person or was it one of these things that it was good to do it once you felt that pain and it was timed fine.

14:49.17
Rob M
I think I think I was not you know I was um I was not in charge of the money there. But what I what I believe the situation had been was you know you hit this milestone. You get a tranche of cash and then you go and you make you make the investment.

14:53.40
David
E.

15:01.17
David
E Easy easy.

15:07.15
Rob M
In in whatever you need infrastructure developers people. Whatever and and that was the way that that company was run and that was the way a lot of companies were run and possibly still are today. You know.

15:16.65
David
And then on the on the development side like what kind of I Guess what were the goals. What were the challenges like do you was that being run well like did you were you just getting features shipped reliably or or was there any kind of like feeling of like why is this. Taking so slow. Why can't we get anything done.

15:40.20
Rob M
Um, I think there is the way that the the company was operating um, well first of all, we we we brought in more developers and that helped and they told 2 friends and they told tool friends so we had this very like network-based you know from the the twisted kind of community.

15:45.94
David
Easy easy.

15:55.93
David
E e.

15:57.94
Rob M
We had. We had a bunch of folks and and with each one each person that we were introduced to we kind of went up the totem pole of who's who in that world and we ended up with um, 2 incredibly talented developers who one like to wear white and one like to wear black. It was quite funny and and.

16:16.39
David
Ah, westworld.

16:17.60
Rob M
Yeah, and and and the the man in white lived in Australia and the men in black lived in Finland and they both ended up coming to Los Angeles either you know for extended stays or eventually permanently. Um, and and these 2 guys you know were we're kind of those like could do. Easily do the work of like 10 people right? They they were very very complimentary and they could they were I know I don't know if they weren't exactly the same in their methodology but they could definitely keep an eye on each other right and that that.

16:37.57
David
A.

16:51.17
David
Is he.

16:55.93
Rob M
Change things because now they they were like well we're going to divide and conquer. So the man in white goes and focuses on building like the best Api he can build so that the salespeople can start to do deals with um website owners who want to serve who want to add video right? and so that.

17:11.38
David
E e.

17:14.72
Rob M
That idea of we need to have an Api creates a whole new line of business for us. You know, which is you know which led to ultimately a white label package in the form of an Sdk that was as easy as unzipping a file and changing a config file.

17:17.91
David
E E e.

17:28.30
David
E.

17:31.83
Rob M
And you if you had like a lamp server. You're good to go your certain video. You know it was. It was so it was made so incredibly easy. We brought in somebody who specifically liked to write like Dev Docs and we had really good documentation for how this is going to run. Um we we. You know we had ah a person on staff who was a decent python developer who also was ah a serious like postgres guy and redid all the way. The database was was being handled like we we started to specialize.

18:05.43
David
Got it and how did you? How did you incentivize bring these people over was it just that they were really happy to work with their friends or was ah you had good compensation. Were they expensive or was it. Something else.

18:21.90
Rob M
Um I think it was ah honestly I think that that companies at that time or in that stage or that have that feeling like they're a part of something that like you know that this is going to be a thing. And there's a possibility that you could be a part of the the thing that that that is it. Um, it feels a little cult like it has a cult like status and I think some of these folks enjoyed the camaraderie. Um, it was a very small tight group.

18:43.79
David
E.

18:56.46
Rob M
and and I consider myself a part of that group like we were. We were spent a lot of time online together and you know as people started to come out and visit Los Angeles I think they could see themselves being here. Um, you know it's nice weather, etc and you know and some of them took.

18:59.83
David
E.

19:14.75
Rob M
Took the plunge and um, you know? Yeah, yeah, yeah, yeah, yeah.

19:15.44
David
But you were but you were working with them quite a bit when they were remote in other countries which it's amazing I mean now that's commonplace but that was not at all then at all.

19:31.35
Rob M
There is There was a ah tension between the executive team on allowing that to continue some of the folks really felt that they wanted to see.

19:37.83
David
He.

19:45.81
Rob M
These people in the office.

19:45.94
David
Was that colored by the the polish guy disappearing or was it just something else.

19:51.84
Rob M
Um, I think I think that didn't help right? but but the way I Always like you know this is going to be a little bit crass but you know the the boss likes to see the minions. To remind to remind them that they're the boss. Yeah, if you if you don't have any if you've got. Yeah if you know yeah, can't be a really you know what super villain doesn't have henchmen right? It's like yeah and I think I think part of that.

20:07.95
David
Ah, yeah I was going to say can you be a boss if you don't have ah you know Surfs toiling the the fields that you can see. Yeah, you got to have minions.

20:24.61
Rob M
Was just a very natural um desire to be like well I want my people here if I if I want to talk to so-and-so I want to just walk down the hallway and talk to them and especially for the Bd people and the salespeople they wanted access to engineers.

20:30.36
David
E.

20:44.30
Rob M
Um, not only because they're probably tired talking to me and have me say yeah well you know I'll add that to the list that we're never going to get it to but they would It was a way you know business people like to go. Yeah, they like business people like to go around the process and try to like tempt the engineers.

20:54.17
David
Ah, they wanted to cut the line. Yeah.

21:03.90
Rob M
Um, to to kind of build something that they want or they need or they think they can sell and that was definitely I Think an honest ambition and and that was driving like this. You got to you should come here and not everybody did.

21:07.55
David
Yeah.

21:18.49
David
Okay, and so and so they did and so they did come sounds like they some did.

21:23.29
Rob M
Some did some did yeah not everybody some did and it wasn't mandatory. Um, and I hope nobody felt that it was but you know but there was definitely pressure you know and.

21:32.63
David
And do you think? do you think that that that actually was good in the end like was there any value to maybe circumventing some of the process or getting that in office energy or. It just really.

21:53.40
Rob M
There There's um, there's a danger I've discovered that there's a a very strong danger when you are the person with the Checkbook or perceived to be the person with the checkbook and it's. Easy for you to become confused with the intentions of the people who are relying on you to write them a check and you know my experience might might be that hey I've got this great team of developers and I really like working with them. And wouldn't it be great if we all hung out and you guys moved here to where I live and we got to work more together and go out and have drink drinks and blah blah blah Blah blah and to me that sounds really kind of fun right? because I'm under the impression that that these are my buddies and I forget.

22:31.42
David
Easy Easy easy. Is it.

22:43.85
Rob M
That you know there's a good chance that we are buddies because I'm give I'm paying them or I'm controlling their their income and when you forget that and you just think you're friends you.

22:50.40
David
E.

23:02.53
Rob M
You kind of tend to create situations that are not ideal for the people relying on on on your the euphra income and I think what may have happened and I feel really bad about it. In fact, is that some of these folks moved and resentment built up. Because as it became clear that the company wasn't going to be the unicorn that everybody thought it was and they find themselves away from everything they know they've they've moved up. They've packed up their whole lives. And and I totally understand how you would start to be resentful of that. Yeah and it's got to.. It's got a name and it's got a face and that's you or in this case, it was me and and I own it now. But but at that time.

23:38.25
David
On that resentment's got to got to go somewhere I mean in your mind is that is that something that yeah.

23:55.71
Rob M
To discover that people were resentful of of having to move for a job or whatever, whatever like like I I didn't understand what I had done wrong I was very ignorant to the situation you know and I wasn't even I mean I wasn't like.

24:03.51
David
E.

24:13.83
Rob M
Fifteen years old I was young but and I should have known better but I I didn't know.

24:17.16
David
I Mean so what? what would you have done differently or what would you I Guess Advise a ah founder in that in that vein.

24:25.64
Rob M
I Think that you need to really figure out like who specifically in terms of vision ownership who needs to be in the office now. The problem is is that a lot of founders who are not technical right? I mean there's a lot of.. There's a lot of issues and I don't need to get into all of them when you have people who start a company because they like the idea that they think that they should make an app or a website or you know a Vr experience or whatever but they actually can't do that.

24:58.63
David
E.

25:01.30
Rob M
Right? And it's almost strange because you know I don't know where where this got into culture but it was like you know. Okay, you know what would be really cool having a restaurant have you ever had a restaurant. No. Do you know how to cook. No do you like talking to people. No do you like working a little. Do you like hanging out at restaurants. Yes, right? So so but the but the the logic is I should have a restaurant and I think that somewhere along the line. Yeah, people were like I like those things I should build 1.

25:27.10
David
Yeah, people have used a lot of websites or a lot of apps. Yeah.

25:36.77
Rob M
Even though I've never I don't have the foggiest idea how to do that. But maybe I'm really good at convincing people that I can do that you know I can make things pretty I'm a good talk or I'm a hustler right? And and yeah everything everything I read.

25:38.37
David
E.

25:48.82
David
Idea guy.

25:54.33
Rob M
You know Mark Andresian says the you know the 3 greatest qualities and startup founders is hustling and not going to bed. Well hey man I like hustling and I have I've you know I have insomnia sign me up and and.

26:03.19
David
Ah, and off by 1 errors.

26:11.61
Rob M
You know and and they hey I can go on like fiverr or whatever and I can find some debs because you know that's not a big deal. It's like hiring somebody to it's like going to home depot and grabbing some of those guys and they'll come and pay offens right? Um, now the thing is that painting a Fs you could probably figure out.

26:23.28
David
Yeah, right.

26:31.45
Rob M
Right? And you know if it's done well. But if you hire somebody to build like a complicated piece of technology for you. How how do you know that it's actually built right? like you? Yeah so you kind of you end up in these situations.

26:40.36
David
Yeah, if you can't tell the difference when a real rolex and a fake rolex you probably shouldn't be selling watches.

26:51.20
Rob M
And you know I I tend to believe that the that you're going to need some people close by close to the founders if not the founders who can actually validate things. And I don't I'm not saying they have to do the building but they have to know if it's done right? and they have to be able to communicate what needs to get built. You know for you know I guess we can disclose this um you know working with a company like superstruct which I have you know I I know going in.

27:16.28
David
E.

27:29.51
Rob M
That I need strong product presence you know with me that that's not what that's not why you hire like a dev shop Typically if you're hiring somebody to build something for you builders you need to provide some blueprints.

27:40.20
David
E.

27:48.37
Rob M
You need to provide the plans you need to know what you want to build and I think what may happen often with companies that want to outsource their development is that they get confused as to what the company is going to provide and you know if you say. Hey, let's okay, let's get together and let's talk about what we're going to Build. What should we build like asking the consultant company. What to build is is probably very confusing for the consultant company because they're like we showed up, We're ready to go. You know we? yeah.

28:11.70
David
Yeah, that.

28:21.18
David
It's like ah it's like for half yeah like your house like it's asking the contractor to to be the architects.

28:26.28
Rob M
Yeah, we got all the guys here they got all the tools show us the plans. We're ready to do it and then it's like no, we should all sit around and talk about what we're going to build and and that's like all of a sudden The biggest waste of money by the way because then you've got people whose specialties is not. Figuring out what to build trying to figure out what to build.

28:49.00
David
Yeah I mean I think that's that's um, you mentioned superstruct right? and and so I mean I'll say I've definitely had ah you know quite a bit of success working with ah you know you Rob and companies that do. Take product leadership seriously and um, a much harder time with clients that don't and so superstruct really tries to filter out and only work with companies that that do take product seriously and the reason is because. For a company to be successful and things are a lot more stressful when a company isn't successful for a company to be successful. It really has to know and understand what its customers or partners depending whatever its business in ah want and that. Is not something that you want to rely on an engineer for or ah, a consultant that specializes in in software development. That's something that that you as the founder or your head of product or um, somebody else that is that is really core. To your business. Ah, that's something that that only they should be trusted with and I yeah it is. It is amazing. How often I see that and I I actually see it a little less. Um where a company like really tries to rely.

30:20.93
David
On a dev shop I think it's more likely that there's just ah, a vacuum where the like I've seen really crappy heads a product do this where they they they think that they have it clear in their mind and so when then they write tickets. It's just like 3 sentences and they expect to get on the phone and like talk it out. Um.

30:22.99
Rob M
This is.

30:37.50
Rob M
Yeah.

30:40.38
David
Because they they want like in their mind I think a common one is like oh well, you know like you're the engineering expert so you got to tell me what's possible or not so that let's just like riff and um, there's there's issues with that but more common ah than than that I think is when you you. Have an engineering team and you want to rely on those engineers to absorb the culture you expect them to learn about the industry and understand the customers and just kind of do what is right for the situation. And I think what's what's a little bit problematic about that is that sometimes you can get lucky and you can have a very product minded engineer who has more of a business sense has more of a customer development sense and they can save you Um, but I think it's a very dangerous bet to make. That you're going to have engineers that are that are good at that.

31:41.75
Rob M
yeah yeah I um I was thinking about this actually today right? and like what is if it's not the founder right? because traditionally like you know you have like 2 founders and 1 is the the product guy and the other is the engineer right? that's.

31:56.37
David
The what and the how.

31:59.45
Rob M
Probably like yeah it's like okay this is what we're going to build you know I don't can you go build this and manage getting it built and I'll continue to riff and take care of this part if you're not going to do that you know because there's no, there's no exact way to do it then like let's say you have um.

32:03.60
David
Here.

32:19.32
Rob M
You know? ah I don't want to say less hands on but let's say the Ceo is not going to be the head of product. The first hire needs to be the head of product. You can't start hiring people or building anything until you have the right person and the head of product is almost like the backup Ceo.

32:27.12
David
A is.

32:38.99
Rob M
I Believe in a startup environment because their their responsibilities are very closely aligned. You know product person has to have a good gut but also be willing to do some kind of user research because you know yeah.

32:52.21
David
Yeah I mean like if you're not yeah if you're not building something people want you're going to have a really bad time.

32:59.70
Rob M
Yeah, and and so they need to go out and get that information like hey you know we put this in front of 250 people and 60% said it sucked. Um, they would never use it. Maybe we should do something about this here's some ideas. Whatever it is like that person needs to be able to do that. They also need to. Be able to interact with customers right directly especially like in ah in a business to businesss um, sensibility where it's like hey I went and talked to I don't know home depot and this is what they said and and I figured out a way to integrate that and and and if you're doing that type of communications. You. You must have a little bit of salesmanship if you're going to be customer-facing and so this product role is possibly 1 of the hardest roles to hire for and will sink your company if you hire the wrong person I honestly believe that this person holds the keys which is why.

33:41.14
David
He he.

33:50.45
David
E.

33:57.58
Rob M
Again, it's typically held by the Ceo or the founder.

33:59.20
David
Yeah, yeah, it's it's that's one of those things that's really dangerous to outsource because if you get it wrong. It's hard to to recover. So for you as a as a founder I get like what. What has led to the most success there has it just been handling the product yourself or have you been able to to figure out a way to hire those people.

34:29.78
Rob M
Um I think now I would say I'm I'm very hyper focused on being able to hire those people or groom those people right? because you know a lot of times someone hasn't had the the opportunity to develop all of those skills.

34:36.73
David
E e.

34:47.15
Rob M
And I do believe that everybody should have like the equivalent of and I don't mean this in ah in a weird way but an apprentice that that they are training to be capable to step in for them because I don't think that anybody should should like no organization should rely on any 1 person including.

35:05.14
David
Yeah, kind of goes back to yeah it goes back to a plane with only one engine. Um, yeah I mean I think for me, that's my way of thinking of that is always where if you want to be promoted. You have to have a replacement.

35:06.72
Rob M
Including the founder. Yeah.

35:22.29
David
And so it's sort of up to you to be able to train replacements so that you are not like forever tied to that role and I think that that in my view I think that matters a lot for founders because you need the company to grow. And so you are almost always looking for a promotion because you need to rise with the company and so you can't you can't have one foot nailed to your previous position because you can't like bring somebody up behind you I mean or I guess you just get really good at hiring. From the outside but that that has its own challenges.

35:57.69
Rob M
Yeah I mean that's you know the the tough part about about hiring from the outside for those types of roles is that people from the outside tend to bring with them and it's It's not always a bad thing but a culture change and can be very disruptive and.

36:09.48
David
E e.

36:14.91
Rob M
It's really easy to bring an outside force and lose like a bunch of people that you didn't want to have leave and and it could be something as stupid as um, this is a real life. So a real life example but hey everyone's used to coming in at 11 a m.

36:18.94
David
He he.

36:33.60
Rob M
Because they code at night. We hired a new Vp of engineering he wants everybody here at Eight o'clock 38 to do a standup and you lose and you lose the whole staff right? or some portion of the staff is just like you know this isn't what I signed up for yeah.

36:49.95
David
Yeah, not not that I've ever left a job for anything like that. Yeah.

36:52.61
Rob M
And and now but you you get my point and then the person coming in doesn't is not really doing anything wrong. They're bringing a formula for success in their mind that works and they're trying to do the best they can and this is how they do it.

36:59.98
David
Right.

37:08.97
David
You hearing.

37:11.74
Rob M
You know, but your culture just got like turned upside down and you have to be ready for that. Um.

37:16.96
David
Yeah, and there's so many so many things like that that that are almost invisible and you just you just don't you don't don't recognize it. Yeah, it's just like a most just imagining like somebody like. Hey guys like I've got this cool thing. It's fire and they just don't know that the room is like full of Hydrogen or Oxygen or something like that And yeah.

37:37.32
Rob M
Um, yeah, yeah, like no yeah, but it's it's and it's hard right? It's hard. Um I've I've seen.

37:52.52
Rob M
I've met and worked with some really really solid product people like really really solid and I've also been around when being a product person became a thing and everybody was a product person.

38:02.56
David
Yeah, what did that change was that was that just something like like Marissa Myers like product manager got super famous or was it before then like.

38:09.69
Rob M
Yeah I I think it was around that time right? and so I I think it was like around you know the mid early the mid um 2000 ah to you know to probably like now even in a way. But.

38:20.70
David
E here.

38:27.25
Rob M
You know I think somebody thought that sounded cool and it seemed like a good role and and and read something about it and then a bunch of people put out some books on how to become a product person or a product manager and then you had all these people who you know five years ago had no interesting computers. Building technology who who were going to be product people and you know and and and companies wanted product people. Everyone you know they listened to a podcast for some clown said you need a product person and they all ran out to try to get 1 and um and I remember having dinner at. Ah, friend's house that I worked with. Yeah yeah, yeah, Dick Clown is me and but I remember having dinner with a friend and his his fiance at the time I was like what were you reading she was like I'm reading this book on how to be a product person and I was like oh what's your job What do you work. She's like oh I do product at.

39:07.45
David
Didn't We just say on this podcast that people need a good product. Ah.

39:24.73
Rob M
Blah Blah Blah It was like oh okay, you didn't strike me as that type of person like I didn't think you liked technology like there's nothing about our conversation that that made me think that you had the least interest in technology so you had all these people I think.

39:28.53
David
And a.

39:43.54
Rob M
Flocking to the field who I don't even know if they enjoyed it because the whole thing is like what what I try to when I ask people um in interviews and stuff right? I don't I don't like to test anybody they'll out tech me probably and I'll just look stupid. So it's more like.

39:46.77
David
A.

40:02.29
Rob M
What is your passion and you get people talking about their passions and then you try to figure out how the passions are connected to what they're going to come do for you right? and sometimes they're not connected at all like you can't put together the puzzle right? like I remember someone came in and then we talked maybe.

40:08.54
David
He.

40:14.62
David
E.

40:20.84
Rob M
Think I talked to you about this guy once I can't remember his name. He was super nice. We talked about beekeeping for like an hour right? And what I was beginning to understand about him was the organization of bees right? that there were these it was an it was an ecosystem that he managed.

40:24.10
David
Yeah, you see.

40:40.58
Rob M
And and all the intricacies of that and and and the process and how the honey get made and and his little relationship with each bee or you know, whatever it was and he was there to do devops and I was like I totally get it I know why you like bees like.

40:55.65
David
A e.

41:00.52
Rob M
I Totally think that you would be a good devops person right? You're going to manage all of these systems you're going to manage all the instances running you're going to have to update them. You're go yeah like you're responsible. Yeah you you know it, You're the beekeeper got it.

41:02.10
David
Yeah, like systems. Yeah.

41:10.30
David
Keep everything healthy like yeah you oh I Love that? Yeah I totally get what you mean.

41:17.59
Rob M
Totally makes sense. Never talk to about 1 thing technically you know, yeah and it was just like okay the personality matches I get it you know and I get why that you would like this job makes total sense to me.

41:31.40
David
So what? Yeah so what? Okay so let's just say you are evaluating somebody for for a product. What would you want to see.

41:44.00
Rob M
I'd like to know what products they like you know I mean an easy one is like I wouldn't ask it so bluntly but like let's talk about cool products like what are you into you know, like what's the best product out there like I remember I had this friend and he was um.

41:52.29
David
He.

42:00.13
Rob M
You know he was tell I need a job in IT can you know? um I can you give me a reference and I was like okay well what kind of computers. Do you like? do you have at your house I don't I don't really like computers and I don't like using my phone so I have like a flip phone and you just be like wait. What like like you guy. Yeah.

42:15.39
David
Yeah.

42:19.48
Rob M
and and I think with with product people. You know there's they love I think they they have to love the users right? They have to be a user they have to know what it feels like to to be 1 to love a product to have a product that you can't. You can't imagine living without you know I would ah I would assume they have a product of like of the week that they're real excited about that. They're kind of up like they think they live for this shit right? and it doesn't have to be necessarily all software. They just love the fact that we live in a in a time.

42:50.17
David
Eehi ehi.

42:57.92
Rob M
Where innovation happens so quickly that by the time you get your hands on the latest and greatest. It's almost obsolete.

43:03.77
David
I Think the first thing that you said that that like love of users and really for me That's that's what comes to mind like somebody that just really wants to understand the user their problems Like. What they find frustrating what they need to do because in my mind any time that you're making a product. There's literally an infinite number of decisions that you can make you can you can. It's just whether you put this here or over there. Whether you hide it behind a dropdown or you have it on a separate page. You know behind a menu whether you don't allow it at all and you make them email you for that change or whatever it is. There's literally an infinite number of choices and to make any of those choices. Well. You have to understand the user and you have to and and I think where this becomes a very very very Difficult. Position is also having an intuition about the relative tradeoff between okay. User really wants this or this was really going to help the user. How expensive is it on our end to make this real like is this going to make it harder to give them this other thing that they really want or is it going to require a lot of development time.

44:27.85
Rob M
Yeah.

44:39.13
David
To Build This is it going to require a lot of operational complexity to maintain it and I think that combination of really understanding people and. Understanding or at least having an intuition to have the conversations with an engineer um that that technical side that combination is frustratingly rare.

45:05.59
Rob M
Yeah, yeah, one one of the things that um that that I would I would often think about is you know and not just in making products but in anything right? is you're either giving or you're taking and products. Should give it should be not be frustrating to use because that is taking someone is taking energy away from somebody and making them frustrated like.

45:30.34
David
So what's the so. What's an example of taking like a really like long and tedious onboarding sign up flow. Yeah.

45:36.61
Rob M
Um, yeah, like like like where where like you don't have to be ah ah, an experienced person to know that this was not thoughtful like that you just the immediate thing is like Wow you did not have to do this this way. This is way too complicated. Why do you need this right Now. Why are you preventing me from from doing what I need to do yeah like I'm I'm not here to do that I don't want to fill out a survey right now I haven't done anything yet like give me a minute show me what I can do and you know and and the thing about real product people is that they're able to.

45:55.95
David
Yeah, you're making me do data entry and you're not paying me I don't like this.

46:14.25
Rob M
Go through the experience themselves as a user and as a designer right? because they're there's they tend to have like some natural experience design you know abilities. And so they're they're asking themselves like oh you know like why did they do this like what's the point of this. Why? Why am I here now. Um, you know I I was evaluating like ah these online language apps like Babel or rosetta stone etc and I was trying to reverse engineer like what was The. What was the process to present it to me this way and then you'll be like oh that's clever like oh that's clever the way you did that I get why you? oh that's good, right? and to start to have this other appreciation and you know me being the way I am I'm I'm getting excited about the fact that.

46:52.24
David
A.

47:06.17
Rob M
It it was created by people who clearly care about me and want to give me a good experience. Um, you know I would say the same thing about the majority of things that Apple does you're like oh this was a gift. Oh it given again, it's giving again so much that when they do something wrong like the butterfly keyboard.

47:14.45
David
E.

47:25.44
Rob M
You're just like wait. What like the earth crashes because Apple did not give you a gift you know, like like I can't believe you rolled out this keyboard that hurts my fingers like wait wait this is so on Apple but some companies you know that they're really.

47:30.23
David
Ah, yeah, yeah.

47:38.72
David
E he.

47:44.47
Rob M
Bad at at design and it's and you can blame the product people like you can tell if the company has a good product team by the products they put put out and I'm not saying that the engineers don't have tons of input. Clearly they do. But. That that product person is responsible for what gets out to the public.

48:06.69
David
Yeah I mean I I Yeah going back to what we were talking about before product is the what Engineerings The how and many times there is no how for a given what you do need the engineers to be able to say like no, we can't do that. There is no. There is no how that will. Get us that or it would be something like yeah we could do that. But if we tweak the what a little bit we can do it much faster or much less expensive or with much less pain and I think those conversations are really important and and actually.

48:39.39
Rob M
Yeah.

48:44.90
David
I think a question for you is how how have you seen the relationship between product and engineering ah go wrong and and how have you seen it go? Well I mean what? what leads to good productive. Um. I guess process or or working between between those 2 functions.

49:10.80
Rob M
I Want to be careful because I don't want to stereotype engineers. Um, but there's definitely like there's definitely like an engineer engineer persona right? and and the the typical engineer Persona makes you work. You got to work for it. A little bit. You got to prove yourself.

49:11.92
David
Oh it's okay, this is a safe space.

49:28.50
Rob M
Um, you know I can remember lots of times the the minute somebody figured out that I wasn't a complete moron technically because you you know I think if you talk to me like just hanging out. You wouldn't think I was like a technologist you might just I don't know what you'd think right? But there'd be. There've been,, there's times in my career where I remember that an engineer was like oh wait, you shouldn't know how to do that. You know, yeah, it's like it's like well you know I'm not as useless as you think and and.

49:54.10
David
And then you reveal that you have like an entire server room in your house.

50:05.14
Rob M
I've tried to strategically use that to my advantage to gain respect at the right time so that I can be in the club without asking to be in the club right? because if you think back to like you know Michael Scott or somebody who so badly.

50:21.11
David
Shit.

50:24.84
Rob M
Wants to be loved by the staff that he ends up alienating everybody constantly and and of course himself you know I always thought the best way to to interact with engineers was to naturally.

50:31.56
David
E he.

50:43.95
Rob M
Show them that that I have a deep respect for what they can do and by the way I can I don't claim to be better at it or know a fraction of what you do, but I know enough to have an appreciation right? and I think good solid product. People don't have to be engineers. To to be that to understand like just how incredibly impressive a mastery of technology is when done right? But and I think they need to be able to identify when it is done right? You know.

51:11.89
David
Me.

51:19.74
David
Totally and and I guess I I think the thing for for me I'm I'm wondering is like what? Yeah, what? what is that process right? So like how how do you set up like either I Imagine you know more recently. It would be that you do have a product person. So How do you set up that system so that the product person can be successful and the engineers can be successful like that that the engineers actually are building things that are useful to the business and the product person is. You know, getting what they want done.

52:02.60
Rob M
Um I think it's It's like there's different um buckets of validation that we all want right? and there's like validation from our friends and our family and our partners. There's professional validation which is hey I want this from the owner of the company or my you know my manager or my my peer group at work. Um, and then there's customer validation and I think that there needs to be a very.

52:35.81
Rob M
Blissed way for product people to ensure that the engineers are receiving those last 2 buckets constantly they need to know the appreciation that customers have they need to always understand that hey this thing that I just wrote.

52:42.41
David
E.

52:54.53
Rob M
You know on my computer actually has implications beyond me. You know, pushing it to git like there's someone who's impacted by this and especially if it's positive right? The negative stuff you can manage and it can help like.

52:59.52
David
E.

53:11.77
Rob M
You know hey we got this feedback and no one called you terrible but we should do something about this but the positive stuff is so important and I think if the product person becomes kind of the administrator of positive validation. It actually can can help manage.

53:17.14
David
He he.

53:31.41
Rob M
That relationship and and and make it very very um, positive for everybody and and also it will allow them to better understand the the plight of the engineer and and there are. Times along the way that I think the product person can open up and show that hey in this position I'm in here's all the things that I deal with for everybody but you still get to have your moment like I don't prevent you from when it's great.

53:59.14
David
E e.

54:08.37
Rob M
We point out that it's great and you did it I don't take the credit from you. You know I mean we talked we've talked about this before this idea of credit in in um, in corporate America where everyone's just people aren't it's the currency right? I want to show.

54:08.70
David
Man.

54:23.37
David
A.

54:27.79
Rob M
Ah, that I I did something great because ultimately probably I want a promotion or I want to rave or whatever and that's just the way we're taught and I might I might be so aggressive on how I get that credit I might be cutthroat about it.

54:42.47
David
E He e.

54:44.35
Rob M
Like I don't care who doesn't get credit as long as I do and if you're the product person who's that person the engineers are not going to react well to you. They're going to smell it right away. Oh that person's here and they just want. It's a step This is a stepping stone for them.

54:51.10
David
E.

54:57.31
David
Yeah, yeah, it's a good point.

55:00.10
Rob M
Especially an engineer who's been there for a while and they're like dude I show up every day and and I I do my best and I I maintain this thing that nobody wants to maintain anymore and I deliver new features and I do it all by myself, right? And no one Thanks me like I you know, let's just say I. I manage the ticketing system and the new. Whatever right? You probably wouldn't you'd outsource that but you get my point I'm doing the least sexy thing ever And meanwhile this person is just taking credit for everything and I think that's a way that that ultimately the product people end up.

55:21.41
David
Sure yeah.

55:33.71
Rob M
Doing themselves a diff save a disservice and and alienating themselves from the engineering group. You know I don't think the engineers necessarily want to be product people right? they may they may not but I don't think like every engineer secretly wants to be a product person I think Engineers want to contribute.

55:37.59
David
I think.

55:53.45
Rob M
To the making of exceptional products.

55:57.17
David
Yeah I completely agree I mean I I've definitely seen it Ah, where the most important thing for for an engineer is that people are using and enjoying the the thing that they that they built like it's actually being being used.

56:10.48
Rob M
Yeah, it's its it's like falls into that like you know, have you ever been in a company and you know you make a hundred things and 99 of them nobody see and it's it gets real frustrating because it's like no one ever uses our stuff man you know? yeah.

56:21.84
David
Ah, yeah, right? But that's why yeah yeah I Guess we're going back to the to the value of product is is making sure that you're you're actually building something that that people want.

56:28.47
Rob M
I work I you know I work on the stuff that nobody sees Oh cool.

56:37.75
Rob M
Yeah, yeah, and and and you know whether that's users or or businesses or whomever like being smart enough to know that you're building the right things right? and that is the job of product. That's not the job of engineering you know.

56:50.23
David
Um, yeah, oh Rob this has been great where can people find out more about you online.

57:00.92
Rob M
Um, I'm actually on a social media diet so you cannot you can find me but I'm not really I'm just ah yeah I'm not and I'm not active on social media platforms. But if you hit me up on Linkedin I will get the email or you can email me.

57:07.45
David
Broadcasting. Okay.

57:16.49
Rob M
Direct it's Rob Mcgray at gmail.com you can Google me Rob Mcgray and I'm easy to find. Thank you David it was. It was very very fun to have this conversation and ah you know, just again to um, all the listeners out there. You know, ah hopefully found.

57:20.87
David
Awesome! Thanks for joining me today.

57:36.30
Rob M
Something here valuable and you know I definitely feel I feel your plight and I feel your pain. Yes.

57:43.86
David
You're not alone all right folks. That's it for today I'm David Gutman and I hope you join me again next time for the superstruct show.