How Many CTOs?

Transcript: Introducing Our Hosts: Scott and Brad

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0:00 Brad You're kind of constantly behind and constantly thinking about something that you don't quite yet need.

0:09 Brad To me, that's very exciting.

0:29 Brad We've got this podcast we're doing,

0:31 Brad Scott,

0:31 Brad and people probably want to know who we are.

0:36 Brad So tell me a little bit about yourselves. Tell the listeners about yourself,

0:40 Brad Scott.

0:41 Scott I would love to.

0:43 Scott My name is Scott Porat.

0:45 Scott I was born and raised in Seattle, Washington,

0:48 Scott where I still live, although I lived in a few other places for little bits of time, but most of Seattle my whole life.

0:56 Scott And I have been working doing consumer facing internet my entire career since 1995 is when I got my first job doing it. I got a job building a website for a department at the University of Washington where we both went to school and I didn't really have any plan when I graduated.

1:20 Scott But math and computers always came naturally to me.

1:23 Scott I didn't have any intention of getting into software or technology or anything like that.

1:29 Scott And that came easily to me and it's continued to come easily to me. And at that time, the Internet,

1:34 Scott you know, the Internet as we know it, the sort of commercial Internet,

1:37 Scott the World Wide Web was just coming into being and everybody

1:43 Scott was learning how to do it in real time.

1:46 Scott And it was easy. I took to it naturally and I learned quickly and I just rode the wave as it happened.

1:54 Scott And so I've been doing that with that's almost 30 years. I'm embarrassed to say how long it is. That makes me feel so old.

2:01 Scott And I've been fortunate.

2:03 Scott I've always I've almost always worked in early stage.

2:10 Scott companies that are you know either at the very beginning or just recently started with the exception of what I'm doing now I've joined a company that's actually quite a few years old but other than that mostly it's early it's almost all been consumer internet a little bit of enterprise type internet stuff but mostly consumer facing and I have always gravitated towards

2:36 Scott kind of whatever was newest and hottest and exciting that was going on I like the figuring it out part can we make it work as opposed to the when you get more into the optimization phase I don't find it quite as interesting

2:52 Scott and so as I mentioned I've done a lot of early stage things some have been tremendous success some have been complete flops

3:00 Scott startups that never either started or up I got had lots of ideas along the way if if I had a nickel for every folder where there's a project in there they got started oh this is a great idea we should do this and you start coding away at it but then it just clears out I would have a pile of nickels for sure and

3:22 Scott I've just I've just did a bunch of things I started out early it was just in kind of building websites then I got into you know on online media I worked on

3:34 Scott One of the earliest versions of ESPN.com.

3:37 Scott I

3:37 Brad You

3:37 Scott worked at

3:38 Brad were

3:38 Scott a company

3:38 Brad at Starwave,

3:38 Scott called I

3:38 Brad weren't you?

3:39 Scott was at a company called Starwave. That's right.

3:41 Brad Yeah.

3:42 Scott And at that time, we were doing online media and the piece that I was doing was what we would now call content management systems. At that time, we call it automated publishing.

3:54 Scott But figuring out how to do content management systems.

3:58 Scott And I actually had three different companies did that. And I really enjoyed trying to figure that out.

4:03 Scott I then went, it worked in some e-commerce.

4:06 Scott Well,

4:07 Scott the whole world was figuring that out during the first dot-com boom and then did sort of social media user generated content during the sort of web 2.0 boom and then got into the gig economy,

4:22 Scott the sharing economy space.

4:25 Scott and did that sort of during that boom and then I met you at a company called 98.6 which

4:31 Brad During the online virtual health boom.

4:34 Scott during the online virtual health boom during the 2020 pandemic right the COVID pandemic so did that for just a little bit I worked with you there that's the first time we worked together and as I've said to you before I felt like I found a kindred soul

4:48 Scott amongst a sea of lost souls so it was fantastic to get to work with you and then i uh went and have since then worked two more times in gig economy businesses um so i've done three gig economy businesses i just said that really fast i should say that say gig economy businesses three times slowly so

5:07 Brad Yeah.

5:08 Scott uh that's what i've been doing and i miss the bitcoin boom the

5:14 Scott The cryptocurrency thing was never for me, never resonated with me.

5:20 Scott And at first, I was an AI skeptic, although I have started to turn around on that as I've started to figure out, I mean, not just me, but as I've started to see ways that it's being figured out how it can be used in like meaningful ways.

5:38 Scott And so I don't know if I'll do an AI kind of startup or something like that,

5:42 Scott but it's something that more recently has caught my attention.

5:45 Scott I'm not an AI cheerleader yet. I'm not like all rah-rah AI,

5:50 Scott but you definitely start to see some cool things and you start to realize,

5:54 Scott wow,

5:55 Scott I mean, we're in the first few pitches of the first inning with AI and this is going to be.

6:04 Scott Maybe scary powerful.

6:06 Scott I understand a little bit more now with the ethicists.

6:11 Scott They call them the ethicists and people concerned about the ethics of AI we're thinking about because you can start to see how this stuff is really going to take off.

6:22 Scott So that's been my career.

6:25 Scott I've done some fun things.

6:26 Scott I mentioned, you know, Healthcare 98.6 where we work together.

6:31 Scott which didn't healthcare didn't resonate with me that much in terms of the technology side of it I should say but I've done some fun things the first time we met was a company I was working at called cheeseburger that was sort of during the web 2.0 era which was user generated content all sorts of humor and internet memes kind of things that

6:53 Brad Yeah.

6:53 Scott was a lot of fun

6:56 Scott uh ESPN was a lot of fun we mentioned that earlier um and probably the biggest success I had was with a company called Rover during the gig economy time where we um you know built an online marketplace for pet care services mostly dogs but cats as well and all sorts of other funny animals there were squirrels and horses and snakes and all sorts of things people need uh pet care for but that was a fun

7:23 Scott thing as well and what I think connects a lot of the fun stuff together is how fast they grew in every case you sort of feel like felt like I had the tail of the tiger and I was just holding on for dear life and

7:36 Brad No way.

7:36 Scott that is addictive actually

7:41 Brad Yeah, it is.

7:42 Brad That's one of the reasons startups are so fun.

7:45 Scott Yes. Well,

7:46 Scott it's interesting you say startups are so fun.

7:48 Scott Startups are well suited for masochists, right? People who like to hurt themselves.

7:52 Scott And so

7:55 Scott I guess that's who I am.

7:57 Scott And currently,

7:58 Scott I am not really a startup.

8:00 Scott I am leading the engineering team for a company called TaskRabbit.

8:04 Scott TaskRabbit is a gig marketplace for home services.

8:08 Scott It operates in the United States, Canada,

8:11 Scott and Europe.

8:14 Scott Thousands of tasks and taskers happening.

8:18 Scott every day millions of tasks a year getting done through the platform and it's a little bit more mature of a company it's actually the oldest company I've ever worked for 15 years

8:29 Scott is the age of the company.

8:31 Scott I've never worked for a company more than eight years old before.

8:34 Scott I've worked for two companies that were eight years old.

8:36 Scott And for both of those companies,

8:38 Scott I was there for all eight years that

8:40 Brad Exactly.

8:40 Scott I worked there.

8:41 Scott So this is something new for me to come in a little bit later and help a team that

8:51 Scott It wasn't really doing very well, and there's a lot of reasons for it around the team,

8:55 Scott not just the people on the team, because they might hear these podcasts and I want them to know it wasn't just the team.

9:00 Scott It might have been the team, might have not been the team.

9:03 Scott It takes a family or a village, right?

9:05 Scott And so much of the whole organization has to be lined up right to help engineering thrive.

9:11 Scott Just like for a company to thrive,

9:14 Scott engineering has to thrive.

9:15 Scott So we're trying to help bring that team to another next level right now and grow that business as well.

9:22 Scott And the last thing I'll say on that is an interesting thing about TaskRabbit is it's entirely owned by Ikea.

9:29 Scott And before I worked for TaskRabbit, my wife and I have been big Ikea fans and big Ikea shoppers for a long time.

9:36 Brad Yeah

9:38 Scott We've learned how to navigate their stores peacefully and how to make it work for us.

9:43 Scott We've learned a lot about their products and have thought highly of them, you know, for what they are. I mean, they're not the Rolls Royces of furniture,

9:50 Scott but what they are.

9:51 Scott And getting to then come inside IKEA and see that company from the inside has been really fascinating.

9:58 Scott It is.

10:00 Scott The best way I can describe it is a magical place.

10:03 Scott Now, of course, I have, you know, stars in my eyes about it, but IKEA is 80 years old. It has an incredibly strong culture, an incredibly strong set of values, and it is a well-oiled machine.

10:18 Brad My sense as an outsider is that it's super intentional and

10:23 Scott Incredibly

10:24 Brad that intentionality

10:24 Scott intentional.

10:25 Brad probably.

10:28 Brad helps define their culture and everything about them, their values and everything.

10:33 Scott Absolutely. It is so incredibly thoughtful how they do everything.

10:37 Scott That has served them extremely well over the years. There's times it doesn't serve them well when the market is shifting quickly and they need to shift quick.

10:46 Scott That doesn't help them as well.

10:47 Scott So,

10:48 Scott for instance,

10:49 Scott IKEA was a little behind the ball on e-commerce.

10:52 Scott They thought, figuratively speaking, who is going to want to buy furniture online?

10:56 Scott Well, it turns out people buy everything online.

10:58 Scott So they got caught playing a little bit of catch up there.

11:01 Scott But it's really amazing to see a mature company that's developed its culture and values and like you said, thoughtfulness over the years.

11:10 Scott And it's remarkable to see a company where people are lifers and they

11:15 Scott buy into that culture and they create that culture and that's how you create a company like like ikea last thing i'll say about ikea ikea is also similar to patagonia owned by a not-for-profit foundation so the profits it makes goes to charitable causes which is also like very meaningful right you know often we're just working to make money for venture capitalists or investors or something like that and so it's nice to

11:42 Scott do something where you're making something for some good for the world without us and not necessarily doing a thing that's good for the world.

11:48 Scott That's sort of been my story.

11:50 Scott And I'll say one last thing about my story, if I can, I didn't mention this, Brad.

11:54 Scott In my engineering leader now,

11:56 Scott I've done a little bit of everything.

11:58 Scott I started out kind of as a web programmer, learned how to be a programmer.

12:02 Scott I was an engineering manager.

12:04 Scott I worked for three or four years as a product manager.

12:08 Scott I like to say I've sort of done everything except for design and the whole thing because I would be a terrible designer.

12:14 Scott I worked as a manager,

12:15 Scott product manager. I worked in IT for a little bit while and worked in what we would now call DevOps.

12:22 Scott technical operations and it was all those kinds of experiences I had that got me my chance but my sort of first CTO job it sort of felt like I'd done everything and was well-rounded and then I've been in engineering leadership since then with the exception of I had a six-month detour to be work in marketing

12:41 Scott And I was terrible at it. I failed and went back to work in engineering, but I learned, I mean, I learned a lot about how marketing works.

12:49 Scott I'll give you a whole new respect for that discipline.

12:51 Scott And, and so I think part of what got me to where I am in my career is just having done kind of a lot of it, a lot of the different roles.

13:03 Scott And it.

13:06 Scott You know, as I said earlier,

13:08 Scott this is sort of a team sport and being able to have been in a lot of the different shoes as a leader makes it easier to bring people together and bridge gaps just because I can kind of see where people are coming from.

13:21 Brad A hundred percent.

13:22 Brad Yeah.

13:23 Scott That's my story.

13:24 Scott What's your story?

13:26 Brad I love it, Scott.

13:27 Brad You know, it's so interesting.

13:28 Brad You know, you and I met years and years ago back when you were at ICANN as cheeseburger and I was at revenue science. We're both CTOs at that time.

13:37 Brad And like you said, when we worked together in 98.6, really hit it off with you. And it's so interesting to hear,

13:44 Brad you know, you tell your story in more detail,

13:48 Brad you know, than I think we pick up, you know, in our acquaintances and working together because.

13:52 Brad There's so much of your path that feels similar to my path, and maybe that speaks to why we hit it off.

14:03 Brad sort of seem to understand each other I too have basically my entire career spent in Seattle I can't claim to be born and raised in Seattle my dad was in the army so I kind of moved all over the place but I was born in Washington went to the University of Washington just like you did came out of the UW

14:24 Brad In the late 80s and started my career at Asymmetrics, which was Paul Allen's company that he started after Microsoft,

14:35 Brad after he left Microsoft.

14:39 Brad Really hit the, you know, just like you with Starwave,

14:42 Brad the internet was just starting to happen.

14:46 Brad And in 94,

14:48 Brad I went to a little company called Real Networks. I was like employee.

14:56 Brad There was about 12 of us there when I started and I rode that through going public and, you know, and ultimately ended there eight years later as a VP of engineering for our systems division,

15:13 Brad which had like some like 500 engineers in it. And we were building all the audio video codecs for streaming the early days of streaming on the Internet.

15:21 Brad Internet.

15:23 Brad And so I would definitely kind of that probably chalk up to one of my more like obvious successes, you know, helping helping take a company public and

15:31 Scott Mm

15:31 Brad growing

15:31 Scott -hmm.

15:31 Brad my career in that way.

15:35 Brad After that, I kind of got my first CTO gig at Revenue Science.

15:40 Brad That's where I was at when you and I met.

15:42 Brad And that was another kind of example of we were really early on behavioral ad targeting.

15:47 Brad We were one of the earliest behavioral ad targeting companies.

15:50 Brad And we'd actually done some other really interesting stuff.

15:53 Brad We kind of built like our own internal proprietary like no SQL database before no SQL is a thing. But we were processing about a billion transactions a day of.

16:02 Brad of of intent data from AOL and Wall Street Journal and Kelly and we were just like munging all this stuff together into into behavioral ad targeting so that was a pretty exciting like early days of of something that now is you know commonplace in the internet you know targeting people based on the interest that they indicate

16:25 Brad I from there I actually left there as CTO and started my own company that I learned a lot from that process.

16:35 Brad It was one of the it was an early,

16:37 Brad early social network focused on sort of like fitness and wellness.

16:44 Scott I did not know that part of your biography.

16:47 Brad yeah it didn't go anywhere that's why you don't know it because it was a it was a failure but we but we we um you know we bootstrapped up to um we you know we were doing a fair amount of like traffic but we just it was like at the dawn of the social media the web 2.0 and um we couldn't quite keep up with the the other sort of networks that were out there in that niche thing and ultimately we saw that like social networks stopped becoming niche they became like

17:12 Brad you know, all-inclusive, kind of like the metas of the world.

17:15 Brad And so, but it was a great learning experience, kind of wore the founder hat or the CEO hat or the CTO hat as well. And so it was just like, it was a good experience.

17:26 Brad And for a bit after that, then I kind of put my shingle out as like a fractional CTO and worked with a ton of really interesting startups in the space where I would kind of help them build their teams up.

17:38 Brad up um i one of those uh ultimately turned into a full-time gig where i was the cto of a company called coreo this was years after my startup but it was a similar sort of like youth sports social network type product

17:54 Brad And then after that, I became the CTO of a company that was working in the VR space early,

18:02 Brad early days of VR before the before the headsets existed. But the early version of the.

18:11 Brad The DK1,

18:12 Brad the developer kit one by Oculus before Meta bought them was starting to be out in prototype form and we built a software platform that was basically a metaverse software platform.

18:23 Brad So that was that was a pretty exciting time and that was another company where it was, you know, I got to.

18:29 Brad pivot from just being the cto running large teams to you know writing code again hands-on code um that was a lot of fun that project um i did that for

18:43 Brad I think almost eight years, actually, and then and then left for a bit, did a little sabbatical, kind of went into the mountains, became a ski patroller, spent spent the year of COVID actually in the outdoors and avoiding small spaces and people breathing on me.

19:01 Brad And and then and then I.

19:03 Brad basically ran into you at 98.6 kind of left the left the mountains and joined 98.6 during their massive growth phase and and you and I kind of reacquainted ourselves with each other and got to work together that was a lot of fun I think that you know I I kind of like you I think that health care is a really tough space and I think that

19:27 Brad And I took it on because I kind of love taking on challenges and learning new things, you know, just like going into VR was a thing that I'd always wanted to do computer graphics, but I hadn't really done a lot of computer graphics. So that was kind of I was drawn into that space.

19:44 Brad Um,

19:44 Brad and the being pulled into healthcare kind of was like, oh,

19:48 Brad this seems really important.

19:50 Brad Maybe I should, you know, go jump into that into the fray there.

19:56 Brad But you're right, it was very, I mean, at least for me, it was it was

20:00 Brad a difficult space to work in.

20:05 Brad But I enjoyed the time there.

20:07 Brad And I think that I walked away from that with a lot of really interesting lessons about how cultures impact.

20:23 Brad uh team efficiency and how how easy it is for um good ideas that seem good on paper to sort of actually make things more challenging for a team to be high performance and so there's so I think that's kind of what I felt like I learned a lot from that experience from there after I left that I kind of went back to the fractional CTO work and uh

20:50 Brad About a year and a half ago, got really, really busy again with another company actually,

20:55 Brad interestingly enough,

20:57 Brad is actually high fidelity again,

20:59 Brad but they kind of wound down and stopped doing the VR stuff and they started up a new project in remote work. And we're in the early stages now at pre MVP of a really interesting tool that

21:15 Brad You know, we've done a couple of pilots with customers, but it's a tool that basically encourages collaboration and connection with remote teams. And it's just something that I'm really passionate about because for eight years before the pandemic when I was at.

21:30 Brad High Fidelity, the VR company,

21:32 Brad we were a fully remote team.

21:33 Brad And so I'm a big believer in the power of remote teams and being able to tap into talent,

21:43 Brad no matter where they happen to be,

21:45 Brad so long as you can develop systems, processes and culture that can.

21:52 Brad uh,

21:52 Brad facilitate and really, uh, allow those team members to shine.

21:57 Brad Um,

21:58 Brad yeah,

21:59 Brad so that's kind of my, my career trajectory.

22:01 Brad It's always been in the startup space.

22:03 Brad I love the startup space.

22:04 Brad I love the fact that you get to wear so many hats.

22:07 Brad You get to,

22:08 Brad um,

22:09 Brad You constantly are facing new and unique challenges.

22:14 Brad Those challenges can be anything from technical challenges like how are we going to solve this problem of streaming video over 28.8 modems, you know, those early technical challenges like that to, you know, even simple things like, well, how do you how do you design a culture of quality?

22:36 Brad somebody in a small team in a new team how do you how do you like you know maybe you've got a bunch of junior engineers that haven't don't have a ton of experience and you're trying to help them understand how to shape their their work processes and their style and their culture so that they kind of build quality in and speed in and you know kind of constantly balancing the the golden triangle that we talk about and so

23:01 Brad It's it's it's super fun.

23:02 Brad I can't I mean, the largest company I ever worked for and the oldest company I ever worked for was Real Networks. When when I left there, I'd been there for eight years and they were, you know, like maybe eighteen hundred employees at that point when I left.

23:24 Brad But I'm so I've been in the big company, but I am almost always in the in the, you know, somewhere between the 10 to 100.

23:34 Brad And that that space is a lot of fun. You still can know everybody.

23:39 Brad You can still, you know, you know, you get to really understand everybody's personalities and you can kind of develop.

23:50 Brad leadership styles that allow you to really um get the most out of everybody by really sort of knowing them and letting and knowing their them how they how their what their authentic self is so that you can really kind of leverage that and tap into that i think i think that's just so much i get a lot of joy out of that you know that process so

24:13 Scott I'm going to ask you a question.

24:15 Brad Absolutely.

24:16 Scott You had mentioned you've done some.

24:19 Scott interim CTO types of things maybe some coaching advising things

24:24 Brad Yeah.

24:24 Scott along the way are you still doing that are you totally focused now on this new project

24:28 Brad It's so funny you asked me that I've got I've gotten recently several people have reached out to me. I literally was driving to the mountain over the weekend and got a call from somebody who's like,

24:37 Brad here's my problem.

24:38 Brad Can you come in and help?

24:39 Brad And so I am pretty busy with my current project, but I.

24:44 Brad But I love helping other folks out. So I definitely do advisory stuff for folks.

24:49 Brad I've there's a handful of different entrepreneurs that know me from my past that when they start kicking up new things, especially like I had when I was when I was really doing that more actively,

24:58 Brad you know, I feel like my specialty was entrepreneurs who weren't necessarily technical themselves,

25:04 Brad like they had, you know, kind of tech, they worked in tech companies, but they were either on the sales product.

25:10 Brad product or marketing side of things and they had this idea and they would come to me because they knew they worked with me in the past and they knew my my skills and they would say like how do I make this happen how do I build this thing you know and in fact the team that I'm working with most recently you know the team I'm working on now like founder reached out to me and he basically had an idea that was going to leverage some of the assets that they had from the early VR days and

25:35 Brad it was basically a kind of a back of the envelope i have this idea how do i how do i get started you know and um that's that's a lot of fun you know like being able to bring your skill as a as a technologist you know like we're we're so i think one of the things that sort of most technologists like you and i are really good at sort of like

25:59 Brad putting the puzzle together right like you've got you've got this idea of what you want to build

26:03 Brad here's how we can build let's let's let's step it this way this way this this this right we can we can step it together and we can make progress pretty quickly on on implementing an idea and that's a lot of a lot of joy so yeah i i still do some advising um a little bit of um uh you know

26:23 Brad I don't have multiple currently. I'm not doing multiple fractional CTO stuff because I'm pretty busy on this project.

26:30 Brad But yeah,

26:31 Brad I'm taking on a love talking to other people and helping helping get their project rolling and then, you know, see where it takes it.

26:39 Scott Yeah, I always feel like I have a little bit of a pay it forward obligation when I was early in my career.

26:48 Scott So many people either just through replying to an email or taking a phone call or meeting for a coffee helped me out.

27:00 Scott I can't always do it because life is busy,

27:02 Scott but as much as I can, I try to help out.

27:05 Scott At the moment,

27:06 Scott you know, I just have one, I've done all these things as well.

27:10 Scott I have one coaching client right now and a CEO is also the CTO of their company.

27:17 Scott That's pretty interesting.

27:19 Scott And I'm actually an advisor to a not-tech company.

27:23 Scott To

27:23 Brad Oh,

27:24 Scott company in the grocery space,

27:26 Scott which is interesting.

27:27 Brad nice.

27:27 Scott Oh,

27:28 Scott it's interesting because you start to learn that a lot of these non-tech companies have a lot of technology in them,

27:34 Scott which

27:35 Brad Yeah.

27:36 Scott is pretty interesting.

27:39 Scott I've been noticing that lately with like in airports and hospitals,

27:44 Scott like just the amount of technology in those facilities is just kind of mind blowing when you start to look at it.

27:53 Scott and airlines.

27:55 Scott So that's been interesting to be involved with.

27:57 Scott It's a startup,

27:57 Scott it's a younger company, a company that's trying to get off the ground.

28:00 Scott So I've been able to bring that experience to help them out and then bring some technology experience,

28:06 Scott but more on the how do you get something started side.

28:09 Brad I was going to say the other thing that happened, I'm curious if you've run into this sort of thing. I know I've got this happens to me often when I have.

28:19 Brad non-tech founders who reach out to me and I start chatting with them one of the things that I feel like I enjoy doing and I think happens often is being that translator between the non-technical product owner non-technical founder and helping them

28:41 Brad understand what if they have a team maybe they're working with some sort of like uh outsource team to build a prototype or something like that you know you and i talk about this that notion of kind of being the the rosetta stone the translator and it's so interesting how common those themes are um the last couple um advisory um

29:05 Brad uh projects that i did was a lot leaning into a lot of that like helping you know kind of vet you're hearing this from your outsource tech team let me translate that for you here's here's what they're trying to say to you you know here's here's here's what you should ask them for clarifying questions for

29:27 Scott That on that second point,

29:28 Scott yeah,

29:28 Scott I think a theme of something I've talked to a lot of people about.

29:32 Scott non-technical folks is here's how you manage your engineering team like this is what you need to be asking for from them so that they're doing the thing that you want them to do

29:45 Scott um because often that non-technical person just has kind of a vision in their head for the app or the website or wherever they want but that actually to say like okay i want a demo every week i want a list i want a road map and a demo whatever the pieces are that you do we don't need to go into it here but uh that is helpful to them yeah so i i don't know i've done more and i've dialed up uh the you know the coaching and advising and

30:10 Scott I've done some fractional stuff along the way has gone up and down over the years.

30:14 Scott In the last two years, it's been on the down slope.

30:19 Scott I think in the next four years, it's going to start to go on the up slope.

30:24 Brad Yeah

30:24 Scott I just got some energy back.

30:26 Scott So I have that, you know, I had to recharge, you have to recharge. And I had some time to do that.

30:32 Scott I've always had this idea that I wanted to do. It's actually part of what spawned this podcast, really.

30:38 Scott I call it CTO school.

30:41 Brad Yeah.

30:41 Scott You mentioned a non-technical co-founder trying to find or work with that engineering leader,

30:48 Scott find an engineering leader is very, very hard.

30:50 Scott The other side of the coin is to go from software engineer or software engineering team manager to startup CTO is a whole different follow axis. And I feel fortunate.

31:05 Scott As I mentioned earlier,

31:07 Scott I had all these different experiences.

31:10 Scott I also went to business school and so like I just had this kind of like mosaic of experiences for lack of a better word.

31:18 Scott that kind of put me in a good spot to be able to do that sort of startup CTO thing and I've always thought man there needs to be a class on this thing like hey I'm a I'm a engineering director somewhere or a software engineering manager or maybe I want to start my own company and like it's about so much more than building the software like that's maybe what do you think

31:44 Scott 40% of it, maybe 60% at the most,

31:49 Scott right?

31:49 Brad It's funny.

31:50 Brad What I was going to say is that it's this really interesting balance where it's probably all it's almost all about building the software until it's very much not all about building the software.

32:02 Brad Right.

32:03 Brad And it's like you have to it's that's one of the things that's so exciting about startups is that.

32:09 Brad It's that you're constantly asking yourself,

32:12 Brad am I ready yet to do dot, dot, dot? And that dot, dot, dot might be grow the team.

32:18 Brad Okay,

32:19 Brad if you're growing the team, then how are you selecting the best candidates?

32:23 Brad How are you measuring their performance?

32:25 Brad Oh, I'm writing this code really fast and am I about ready to dot, dot, dot?

32:31 Brad And it's...

32:33 Brad figure out do you need layers of management do you need engineering managers do you need and if you have engineering managers then how do you select those engineering managers and how do you how do you manage them and what kind of processes start getting put in place around that right and the and the the thing that's so exciting about the zero to one is you're kind of constantly

32:58 Brad behind and constantly thinking about something that you don't quite yet need and

33:05 Scott Mm-hmm.

33:06 Brad that

33:06 Scott Yeah.

33:06 Brad that inflection point of when you didn't quite need it yet and then all of a sudden you tip over and now you needed it last last month is just this exciting dance of to me that's very exciting

33:24 Scott There's one more piece that you didn't mention.

33:28 Scott My take is that the moment you become the senior most engineering person in your business,

33:38 Scott and it could be a business of one,

33:40 Scott or it could be just you.

33:42 Scott But when you're that person,

33:44 Scott you're actually,

33:46 Scott this is the key thing, I think, you have to recognize.

33:50 Scott You're actually more businessman than engineer,

33:54 Scott business person than engineer.

33:56 Brad Yep.

33:56 Brad Yeah,

33:57 Brad you're more 100%.

33:58 Scott You've become a suit, as they say, right? You're no longer the talent, you're the suits.

34:04 Scott And once I got my own head around that.

34:10 Scott It actually made working with the business people way easier,

34:15 Scott not because I came became one of them, but because I understood what they were trying to accomplish,

34:21 Scott which

34:21 Brad Yep.

34:22 Scott is like whatever it was. Right.

34:24 Scott So it allowed me it made me realize that as an engineering leader,

34:29 Scott you are at the same time like quantum.

34:33 Scott physics whatever you're wearing two hats you're wearing a business hat and an engineer hat and it's not like you toggle between one and the other but you're like both at the same time always I actually sometimes wonder if like marketing people feel that way too right they simultaneously have to like think about the creative that's getting built in the campaign and the concepts and whatever marketing people talk about you

34:58 Scott and its optimization and its spend and its cost and those things and the output of it all at once at the same time.

35:06 Scott I wonder if the marketing folks feel that way also.

35:10 Brad Yeah, I get it. I 100% agree with that. And I think that I have been so fortunate in my career that.

35:21 Brad You know,

35:22 Brad early on, I got to witness that so up close and personal at Real Networks where there was just so few of us and Rob,

35:33 Brad the founder of that company was so, so engaged and so passionate and so he was.

35:48 Brad very strong business person and a very strong technical leader he had a vision for what he wanted he understood what he wanted from a product you know and it was great to watch and to learn in that sort of

36:07 Brad crucible it was so such a intense environment and I have you know my colleagues that I have from those days you know we're still friends and it's so it's like such deep bonds because I think we all were learning so much so quickly in such an intense environment

36:31 Brad And but,

36:33 Brad you know, it's like to your point about like understanding the vision of the business person,

36:38 Brad understanding, having empathy essentially for the business part and not just being the developer.

36:45 Brad I think that's one of the things that is more accessible for developers that are part of startups when they're smaller.

36:57 Brad Because hopefully they're seeing each other,

37:00 Brad they're seeing their business owners,

37:03 Brad you know, in the same room,

37:05 Brad the same virtual room, in the same space,

37:07 Brad in the same meeting.

37:08 Brad And that helps make that pivot for those that want to move into leadership,

37:14 Brad engineering leadership,

37:16 Brad right?

37:17 Brad uh makes that pivot of like you're not just an engineer you've got to be the steward of the business too

37:26 Scott Well, I feel like we have many episodes. We could do a whole series on making the pivot.

37:34 Brad Making

37:34 Scott how

37:34 Brad the pivot.

37:34 Scott to get that whole CTO school concept I sort of talked about.

37:38 Scott I'm going to discuss that some other time. I've got a whole idea about it. Maybe we can make it come to life on this podcast.

37:43 Scott Brad,

37:44 Scott it's been fun.

37:44 Scott We didn't talk about skiing once today in our podcast. We stayed focused.

37:49 Brad Pray for snow.

37:51 Brad This episode of How Many CTOs Does It Take podcast was edited by Saffron Epigal.

37:56 Brad Our theme song was AI generated by Brad.

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38:21 Brad Thanks for listening.