What happens when passion, persistence, and curiosity meet the brutal realities of startup life? In this Failing Forward edition of Not Another CEO Podcast, Nick Freund sits down with Anthony Corletti, a seasoned technical founder and former CEO of Casa, to unpack his entrepreneurial journey.
Anthony shares hard-won lessons from building, and ultimately shutting down, his company, discusses frameworks like the "Founder’s Care-o-Meter" and the "Personal Board of Advisors," and reflects on how founding has shaped his broader life perspective.
Takeaways:
The Spark for Entrepreneurship: Anthony shares how working closely with rideshare drivers during his early startup days ignited his passion for solving real-world problems through tech, and how the immediacy of feedback fueled his love for early-stage building.
What Drives a Technical Founder: For Anthony, the excitement lies in scaling impact, solving one user's problem in a way that could eventually benefit thousands. His love of learning and "always day one" mindset continues to push him forward.
The Lightbulb Moment for Casa: A podcast analogy about how context transforms perception inspired Anthony to rethink how engineering workspaces could better integrate product and design teams, leading to the idea behind Casa.
Introducing the Founder’s Care-o-Meter: Anthony explains the framework he created to check his conviction at different stages of building Casa. He tracked whether he still felt a "hell yes" about the mission and scored his emotional connection to the problem versus the solution every six weeks.
Building a Personal Board of Advisors: Anthony stresses the importance of surrounding yourself with trusted confidants, from family to expert mentors, who can offer honest feedback, accountability, and different perspectives throughout the founder journey.
Knowing When to Shut Down: Anthony candidly describes how feedback from pilot customers, competitive insights, and introspection via the Care-o-Meter helped him make the difficult but clear-eyed decision to wind down Casa.
Founding and Life Philosophy: Anthony reflects on how founding has shaped his view of service, resilience, and embracing life's unexpected opportunities. His future focus is simple: prioritize the people you work with and the problems you solve.
Quote of the Show:
" Experience is what you get when maybe you didn't get what you wanted… being able to share that with [future founders] is such a critical point, and it's super important." - Anthony Corletti
Links:
Twitter (X): https://x.com/anthonycorletti
Website: https://www.anthonycorletti.com/
Ways to Tune In:
Spotify:
Apple Podcasts:
Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261
Transistor: https://podcast.notanotherceo.com/
#NotAnotherCEO #BusinessSuccess #Casa
Chapters:
00:00 Intro
04:14 Anthony's Journey and Early Career
09:10 The Inspiration Behind Casa
14:51 The Founder's Care-o-Meter
19:49 Building a Personal Board of Advisors
25:57 Facing Initial Challenges
26:57 Pivoting and Feedback
27:31 Connecting with Industry Leaders
29:28 Emotional Journey of a Founder
31:01 Reflecting on Key Decisions
33:06 The Importance of Co-Founders
33:46 Customer-Centric Product Development
36:16 The Role of Luck in Success
38:46 Balancing Life and Founding
39:42 Founder's Philosophy and Future Plans
45:55 Where To Next?
48:24 Outro
Transcript:
[00:00:00] David: Hello everyone. Welcome to the first Not Another CEO Podcast, Failing Forward Edition. As many of you know, I've partnered up with Nick Freund to take Not Another CEO to the next level. Nick and I have known each other for a long time, and we worked together for many years at BetterCloud.
[00:00:18] Last year, Nick shut down his company Workstream after raising money, building a product, acquiring customers, and generating revenue. He decided that he wanted to share his story with the next generation of founders and CEOs so they could learn from what he went through. Now that we're working together on Not Another CEO, he expanded past his own story and is now focused on finding founders who've shut down their companies and are willing to tell their stories and share their lessons learned.
[00:00:47] So after the intro, you'll be hearing Nick's voice. He'll be the host of these Failing Forward shows going forward.
[00:00:53]
[00:01:18] Nick: Welcome to the first failing forward edition of the not another CEO podcast. And I like to think of this as the version of the show that's for the rest of us, right? It examines the journeys of those like me.
[00:01:33] Who gloriously fought, but maybe lost. We hear the lessons of those of us who had the guts to start something and the outcome was maybe not what they expected. And so with that, I'm just honored to introduce you today to our first guest. You know, he's a software engineer and a seasoned engineering leader.
[00:01:57] He's a two time founding engineer and a [00:02:00] three time technical founder. He has amazing experience bridging startups, enterprise companies, and academia. He graduated from Carnegie Mellon where he later researched and taught cloud computing and distributed systems In the Master's program he's worked at enterprise companies, most notably Capital One on their CreditWise credit monitoring app.
[00:02:24] He was a senior software engineer at Algorithm. He was the founding engineer at GridWise, which was a rideshare analytics platform in Galileo, which is a San Francisco based startup that's focused on improving AI and machine learning workflows. He's a prolific contributor to open source projects and was the founder of the project Astro Base among, I'm sure many others that I'm probably butchering because I'm not a technical founder myself.
[00:02:54] Um, and if all of that. Was not enough. He's also the former founder and [00:03:00] CEO of Casa Dev, which was a startup aimed at improving how engineering and product teams could work together. This person I truly appreciate. He's a truly gutsy founder. He's someone who publicly speaks about and shares his stories of both triumph and failure.
[00:03:19] And so, ladies and gentlemen, I am pleased and humbled to introduce you to Anthony Corti, the former and f the former founder and CEO of Casa. Anthony, welcome.
[00:03:30] Anthony: Thank you, Nick. That was an incredible intro.
[00:03:32] Nick: Of course. Thank you for so much for joining, and I it's just, it's awesome to have you, you know, I. I've been doing, you know, so I, I've done versions of this show to talk about my, the, the failure of my own company or the shutdown of my own company and the story of what happened.
[00:03:50] And so, and it's always been in, it's always been in my mind and one of my goals to, to start to have others share their stories as well. And so I'm just like so [00:04:00] stoked to, to have you join and to, to do this together. And so there's a lot that I think we can talk about today and. And a million ways or places will, or directions will take the conversation.
[00:04:14] But I think maybe just to start, like you've spent so much of your career in like the earliest stages, starting new projects, starting new companies. Like what, what is it about the early stages that inspires you? Like why do you spend so much time there?
[00:04:29] Anthony: Yeah, Nick, totally. And, and I really love what you're doing with this. I think that a lot of founders should share more about like, things that have gone well, things that haven't gone well, like sharing your experiences, like one of the most valuable things you can do as a founder. And I think getting to the, point of like why I spend, I've been spending so much time in the early stage, early on in my career, I was spending a lot of time just kind of like at Capital One and then teaching, and I was kind of considering do I go back to [00:05:00] school and do like a master's or a PhD or do I kind of go into startup world, like just experience something new. And at my first startup where I was a founding engineer at GridWise, what really connected for me was every time I got into an Uber or a Lyft, it was like a sales pitch. Like my user was the driver and I was trying to understand exactly like how they were trying to optimize their time on the road or not, or like where were they logging their mileage, like where were they logging their expenses?
[00:05:26] And then I could say, okay, cool. I've gotten into the mind of this person, into this like persona. Now I'm gonna go home and like build some stuff and like reach out to 'em and see if they like using it. And since then, like that's just been a flywheel for me.
[00:05:38] Nick: Amazing. I mean, I think one of the, such a, one of the coolest things for like you, I think, or for like any like truly technical founder, which like I'm not, is how. How fast that feedback loop can be, right? Like you can, like you're also a product person. Like you can have that conversation with that Uber or Lyft driver, contextualize it, [00:06:00] get inside that person's like job or day or persona and then like immediately go action.
[00:06:05] That and the speed by which someone with your background can do that is, is. Is so cool to me. It's so cool. But for, for someone like yourself, I also imagine it's just like super re rewarding as well.
[00:06:18] Anthony: there was a moment when like coming back to GridWise where my friends and I were like going out. We were in the car and I was like, guys, sorry, I gotta do, I gotta do a pitch. I gotta see like what this, what this guy, how he thinks about driving on the road. And as we were going out, he was actually using GridWise and he was telling me like.
[00:06:37] Oh, you know, GridWise really helps me identify like how I can go to the airport or whether it's not going, 'cause like that's a very expensive, or could be a very expensive ride out. I burn my time or I could make like a hundred dollars, like really easy if I time it right. And he said how, like this is what he uses to pay for his dollars.
[00:06:54] Ballet lessons. And I was just like, like, this is like incredible. Like I, I need to keep doing this. [00:07:00] Like I need to keep doing this. Um. So that, that kind of stuff really is like such a magnet, like super high reward, I think.
[00:07:06] Nick: Amazing. I mean, you're kind of talking about it, but like, what is it that that drive, like drives you, right? Like, what drives you as a founder, as a, as a technical founder, like why do you do what you do?
[00:07:19] Anthony: Yeah. I, I think like as a, as a technical founder, I find myself more often than not thinking about like. If something scales really well. Then it like that change that you've maybe affected in like that one ride share driver or like this one musical artist you could do for many, many people. And that's kind of like the responsibility that I really feel like good about taking, like that that's the responsibility I wanna take.
[00:07:46] Like making sure that the product is like spot on. It's solving the problem for the people. And I can, I can build that thing. I can build that. I can ship it like I can. There's always something new to learn as well. [00:08:00] Like there's so much to learn about different user personas, like going into different kinds of research.
[00:08:06] And today like software is really becoming like commoditized. Like there's so many great things you can use and try to do things better and faster than before. So I love it because. I also just love learning. I always like try to think like it's always day one, like there's always something new to learn.
[00:08:21] Like how can you take all of your experiences building things from the past and iterate the on those today? So if you grow a team of other engineers, they're like, whoa, this is so cool. I can build stuff so quickly and you can see how fast they accelerate as well into doing something similar. That for me is just like something I absolutely love to do.
[00:08:39] Nick: Yeah, I mean, I think for me and what you said with what the core of what you said is just that, that continuous learning mindset, it just, that resonates with me as well. And I'm, I'm someone who has always embraced that and like what gets me going is always learning something new and, and doing something new.
[00:08:59] [00:09:00] And I mean, there are many attributes of, of founders and technical founders, but that's certainly one that you and I share in common. Um.
[00:09:09] Anthony: Yeah.
[00:09:10] Nick: So I think, I mean, there's, again, there's so much we want, we want to cover today, but let's just look, let's spend a few minutes just like talking about Casa, right?
[00:09:19] Like you, you know, you, you had the confidence, you had the guts to go out and, and start something. Like, what was that light bulb moment for you, right? Like, what was that, that moment that said, Hey, I ha I have to go and do this.
[00:09:34] Anthony: Yeah, there was a lot of conviction in this moment, and that's how, that's how I knew. That's when I felt it. So Casa didn't quite start out as a home for engineering context. It started out as actually like a, a platform as a service for machine learning teams, like better ways to run code in the cloud.
[00:09:53] Um, how can you do that in a way that's like totally reimagined? It's super fast and performant. And as I [00:10:00] was like experimenting, like looking out on the market, I'd already like landed on like a couple of solutions out there. I was like, this is really, really good already. I'm just gonna use those. Like, I don't wanna compete because if I do, I know I'm gonna have to like 10 x.
[00:10:13] Like, this is like, I, I don't just wanna jump into the pool there. And so then I was kind of thinking about like, all right, what do I do next? And one day I was listening to, like a podcast where. The late founder of Virgil or of LVMH of Virgil Ablo was talking about, this an analogy he uses in design and education, where if you take like a candle that's stented, and if you put that candle in a garage, someone might throw the candle away 'cause it looks like trash.
[00:10:42] But if you take the candle and you put it in a gallery space, then it becomes art. And I was kinda like, oh, like. What's that for software. Like how, because an engineer might do some work in a garage, right? Like I like that's how it says starts like in Silicon Valley, like I'm in my garage
[00:10:58] Nick: Your parents' garage, right?
[00:10:59] Anthony: but [00:11:00] it's, yeah, but it's like, what does it look like when you take that and you actually put in a gallery space?
[00:11:04] And I was like, oh, for spending all this time in GitHub. And then I was kind of connecting dots where it's like. If you think about all the software services you sign up for as a team, right? Like everybody's in Google Workspace, there's people in Figma, in Jira, et cetera. But then in GitHub it's like, poof, there's only the engineers.
[00:11:21] And I was like, where did everybody go? What if we could bring everybody into this space? And that was when it connected with a moment that I was thinking, was super important to me. Originally, I wanted to become a software engineer. When I heard this talk from an early engineered GitHub where he was talking about how GitHub uses GitHub to build GitHub.
[00:11:39] And I was like, yes. Like I love this dogfooding mindset. This is so incredible. And that's kind of when it all clicked like that connected with a moment that was like, like a long time ago. And I was like, I wanna kind re reimagine like where our code sits and how our code interacts with other things. We work with, like all our documents should it interact with Figma.
[00:11:58] And like my brain just started going and [00:12:00] I'm like, this is something I, I can take a stab at. This is something I'm really curious to, to start doing research on. Yeah.
[00:12:06] Nick: I love that concept of, or that framework of just the, the, the context that something resides in, like changes its nature. I. And I, I could totally see why that would be so fascinating and transformational. Like for code, you know, you, you said something else that's really interesting to me about dog fooding, you know, like, and, and for some capacity, like there was a dog fooding nature for you at Casa, like, generalizing is like always a fraud exercise, but like.
[00:12:47] For technical founders. Do you feel like that's where a lot of, like where a lot of these products and projects start is kind of like eating your own dog food and then getting enough passion to start a company around it? Like, do you [00:13:00] think there's anything there?
[00:13:01] Anthony: It's so prevalent in dev tools, it's so prevalent because as an engineer you wanna make the best tools for you, and if you kind of iterate on that really, really well, it could land with other people. Where I think there's a really interesting challenge for dog fooding is when you aren't building for a profile with yourself.
[00:13:20] But I think that's an incredibly valuable challenge because it forces you. Forcing function. I need to get into the mind of this persona. I need to get into the mindset of a rideshare driver. I need to get into the mindset of a a and r person. I need to get into the mindset of a lawyer, right? Like there's just so many different people out there who are like, I'm working in this workflow and I like this workflow, but as an engineer, you're like, oh, let me like just spend some time with you and kind of figure out what's going on, and, oh, I can make this like a lot better with some tools.
[00:13:53] Let me try to make some tools for you. Like that's also like a really powerful workflow when you can't directly [00:14:00] dog food the software that you're making.
[00:14:01] Nick: Totally. Yeah. I mean, I think the, that just, that that ability to quickly like build a dev tool and, and dog food it yourself and like that immediate feedback loop, so powerful. Obviously just a very different muscle to, to exercise than building for, as you pointed out, like building for somebody else and for, for another persona, which.
[00:14:29] Maybe looks more like the traditional, like early stage founder or product, you know, kind of product iteration motion.
[00:14:41] Anthony: Yeah.
[00:14:42] Nick: you know, so one of the things that I, I forgot to call it out at the beginning of the show. I. You know, so you, you wrote for the not on their CEO Substack this week. Thank you so much.
[00:14:51] Um, the, the title of your article, which was amazing, everyone should go check it out, the same as the, the title of the session Founding is an Endurance Sport. [00:15:00] And you, you wrote about this concept the Founder's care-o-meter, which I just, I think is awesome. And could you maybe just share for everyone, like what this concept.
[00:15:13] Is, and, how you think others should use it.
[00:15:17] Anthony: Yeah, so a Founder's care-o-meter is kind of like your it's a mix of like a gut check and like a little like exercise that you wanna do on paper or something. And it's compromised of a couple of questions. And the first one is pretty obvious. It's like, is this a hell yes or a no? Like with Casa, I felt like this, heck yeah, like.
[00:15:39] This connected with a moment 13 years ago. It's connecting with me today. I have all the experience to work on this. Hell yeah. And then the next part is to really think about like, how much do I care about the problem? Like is this, like if you were to rank it from 0 to 10, like 0, don't care about it at [00:16:00] all.
[00:16:00] It's a piece of trash on the ground, or 10, like I care about it like my loved ones. That should be really high, that's a good sign on the care-o-meter low. Obviously not like if you don't care about the problem, like as an early stage founder, you really need to just like live with that all the time. And then another part of it is scoring that problem versus the solution. And what I mean by that is if there's a particular solution in the market that you already think is really great, you admire it, you admire the other people doing it. Then that's really high, and if you have a tendency to see like, oh, this thing is really great, then if that score is less than the problem, then you're kind of out of balance.
[00:16:43] You really wanna focus on, the care-o-meter will help you say, I really care about the problem. and The solution is something, whatever it is, like we'll get there, but you don't wanna get too fixated on one solution too early because that kind of locks you into like a, mindset when you really need to be [00:17:00] open to possibility and a lot of information because you also don't know what you don't know about solutions that you just don't know exist yet.
[00:17:07] Nick: So it starts with your personal excitement. Like is it a hell yeah. Or is it a hell no? And I would assume you can like meditate on that, but there's gotta be something, I mean, this resonates with me. Like there's just also something visceral about that. Like you can actually just feel it.
[00:17:24] Anthony: Yeah.
[00:17:25] Nick: Um, and then intuitively, like I think, or academically we all know this, but then it's like are you excited about the problem?
[00:17:37] Right? Like, and the problem first and the solution second. You know, I think. This is just such a good reminder. I mean, when I read what you wrote for me, there were just also times in like in my own journey where if I think back on it, it was like I was more excited about the [00:18:00] solution than I was about the problem at that specific moment in time, which was probably like, I mean, not probably, it was not a good sign, you know, especially within the care-o-meter framework.
[00:18:11] but it's just such a good. Intuitive reminder for any founder as they're kind of navigating that early stage part of the journey.
[00:18:21] Anthony: and you shouldn't do it like every day. Like it's not like every day, let me check my care-o-meter You kinda wanna give yourself some time and
[00:18:28] space because there's so much that happens.
[00:18:30] Nick: yeah, like how often were you checking in with your care-o-meter? That's a great, that's a, that's a great point. Was it every week, every month.
[00:18:38] Anthony: I, did it every like six weeks or so. So every six weeks I kind of had a moment of like, let's just take stock of everything that's going on. How are we with finances? How's the product going? Do I have inbound? Do I have interest? Am I getting design partners? Am I getting good research feedback? Like Six weeks, take stock.
[00:18:58] Look at your, [00:19:00] care-o-meter And if there's warning signs, it's like, whoa, okay, given these signs, am I gonna do another six weeks? Like, that's a really important, a really important point.
[00:19:11] Nick: Did you have, like, was there like something on your calendar to remind you to do that? Did you just kind of remember to do that? Any, advice for forcing mechanism for checking in on your care-o-meter for other founders?
[00:19:24] Anthony: Yeah. Nick, I'm a nerd. I'm a developer. I have a little script that I run that kind of tells me what my six week buckets are, but I think like a Google calendar, just notification. It's like, Hey, it's every six weeks. Just do a, check-in. I think that that's totally fine too. No, no problems with that.
[00:19:44] Nick: when you wrote on the nine another co substack, you also, you know, about the journey. You also spoke about this concept, the, the personal board of advisors which I also just thought was awesome and it was something again that I feel like [00:20:00] I informally leveraged, but I didn't think about in that exact same way.
[00:20:03] So can you maybe just talk to us about that? What is that? How should a founder leverage and, and build a personal board of advisors?
[00:20:11] Anthony: Yeah, so I think starting out, I, I didn't really think about this concept until later when I had this list of like emails that I was just reaching out to people and occasionally there was just like this little group of emails that I just always wanted to send things to, to be like, Hey, what do you think about this?
[00:20:29] Or those were the emails that pop popped up on my calendar, either at. Kind of like regularly scheduled intervals where it was like a coffee catch up. Just like, let's talk about life, let's talk about everything. Let's hold ourselves accountable to like each other and also what we're doing. So at first for me, it was, my, my fiance and wife she was a big part of my personal board of advisors and then also a really, really good friend of mine who had spent a lot of time in the [00:21:00] early stage venture world.
[00:21:01] Who is just fantastic at giving me feedback as like a mentor to a founder. If he's like, look, you're wasting your time doing this. I think this is really great. You should double down here. Those were like my first two. And the cool thing about your personal board of advisors is like sometimes there's a person who just says something to you.
[00:21:21] It can be a sentence that just changes the way you think about stuff. And that that's a part of it as well. So. It's doesn't necessarily mean you have to like continuously bug this person because they might not have time. They might be very, very busy. But recalling that, that feeling and the words that they said to you of like, you know, one for me was like, your persistence will take you a long way.
[00:21:45] It's like, okay, I have to persist. Like I can't just give up on things. Yeah, so I think you can go about building your personal board by. Finding either close family members or very close friends that you really feel comfortable confiding like [00:22:00] almost anything in. Because then they're gonna be able to say, you're connecting with me on a very deep level.
[00:22:05] I care about you. I want the best for you. And I can, I, they might even be able to kind of like, see your carer from like an external perspective. It's like, Anthony, you're getting too tired. Like you don't seem like yourself, like what's going on? Like, they know, like, so if there's that person that can, you wanna feel comfortable sharing that carer with. I think that's a great way to start.
[00:22:26] Nick: So it sounds like it's also about. Who they are and more about your comfort in sharing with them openly and honestly about the journey where you are, the readings of your car meter. And it, does that write to you? Like are there, are there criteria you think we're mi we're missing here around who you should choose or think about for that?
[00:22:56] Anthony: Yeah, I think, for an [00:23:00] early stage technical founder, finding people who have a lot of subject matter expertise as well, people who can help you increase your vision, that's super important. So if someone's able to say, look, I've been doing this for, you know, 10 years in this space, they already like know so many of the pitfalls, like years down the line for you.
[00:23:21] If this person's like willing to engage with you, spend time with them, put them on your board, send them your emails, get their thoughts on like where you think things are headed and if you start to develop that trust when they're like, whoa, you should double think about this. It's like, oh yeah, I should definitely double think about this.
[00:23:38] Nick: yeah, I mean, I, I'm, I'm sure that's true for technical founders, but I would say that's, that's true for any founder. Right. I think, you know, for me, again, I didn't, I didn't. Defined in my brain that I had a personal board of advisors, but my wife was certainly on it.
[00:23:53] Um, I have other friends that are founders and CEOs that were on it Now, my [00:24:00] co-founder had not another co David, right? Like he was definitely a member of my, of my personal board of advisors and. So it was folks that I, I was willing to, to speak openly and candidly about it. And I think there was a, there was a mix of yes, just those folks who really understood me and cared about me.
[00:24:22] And then also those people, like you were just mentioning that have, have deep expertise in, in what you're doing. And, I mean, maybe you could consider putting someone like that on your board, but like. Sometimes that's like a whole exercise too, and there's like politics that can come with that. Just, just having that person on your personal board is probably the most important thing.
[00:24:48] Anthony: and there should be like some variance in there. Like you shouldn't only put, like if you're a startup, CTO, you shouldn't only have CTOs on your board. You should maybe have like even someone who's like [00:25:00] a, a few years younger than you who's maybe a friend and they're starting out as an engineer and they're like, you know what?
[00:25:05] I really wish my CTO could do this or that. It's like, yeah, that's actually a pretty cool idea. Like it's really cool when almost like the mentee kind of becomes the mentor and those kinds of relationships. So I think like the, your personal board advisors can, can grow in all kinds of really cool ways.
[00:25:22] Nick: So you, you alluded to it a little, but like, so these two concepts, the care-o-meter. The, the PBA, like how did these play into your journey, right? Like and your journey at Casa to push through hard moments, to, to pivot into other moments, and then ultimately like to kind of shut things down.
[00:25:44] Anthony: Yeah, the first moment was, obviously at the outset I felt an incredible amount of conviction in the idea. I cared so much about the problem. I cared a lot about, [00:26:00] the. Like the solution as well, but I was ready just to try a bunch of stuff. Like, I was like, what can I just do research on to see what people are using?
[00:26:10] What solutions are other people using in this space? I wanted to learn about that. So really great marks across the board. The first time I started to see a change in that was when, after about six months of building. Things weren't looking so great, like the product didn't get traction. There was a lot of people using it, giving me some like advice and thoughts, but they're like, Nope, would not use this.
[00:26:34] I wanna see this, this, this, and this. This is not like a legitimate platform. I'm like, oh, okay. So it's like when you kind of feel that six month period or six week period, let's see, time to go back to the drawing board. What's the carer say? And it's like. Really still care about this. That's good. Really care about this business.
[00:26:53] Want this to be a business, still really care about the problem solution. I'm like, let's toss this out the [00:27:00] window and let's take this feedback and research and build something new. And so after doing that, the care-o-meter came up for the last time with some serious readings after going through a couple of pilot programs.
[00:27:16] And getting that section of feedback. So feedback is a great thing to feed into your care-o-meter, like external, internal as well. And at that point, some things had kind of become uncovered for me, like stuff I didn't know about. Like my vision was kind of expanded. And once I was able to get insight from a couple of connections who were like, Hey, did you know GitHub has a team that's working on something like this?
[00:27:40] I was like, no, like. I need to talk to those people. And sometimes just being like, alright, I need to reach out to these people and see what's going on. Like this sounds really cool. And just being open about that. Like even if it's like a Hail Mary email to the COO, see if it works, it worked for me. It was super lucky.
[00:27:57] Nick: You emailed the CEO get home.
[00:27:59] Anthony: I [00:28:00] emailed the CO of GitHub and I was like, I just need to figure this out because one of my pilot customers was like. You know, Anthony, we, we like using this new product. It makes sense. We can connect our docs, we can connect our code, we can connect our cloud. We get this really cool turbocharge context space where anybody can ask a question about where the product is at. But here's where we are. We're already in this place that's secure compliant. We have hundreds of developers. We don't wanna move. Can you give us this thing on GitHub? And I'm like, okay, here we go. Like, there we go. And it's, you kinda like, you feel it, like you might just feel it sitting there and it's like, all right, I need to go figure out what's out there.
[00:28:36] I'm like, I don't have that much time. I'm starting to feel some pressure. Let me start to make some of these emails, some calls, do lots of research. And eventually when you see the thing, like if this person was like they opened the door for me for some closed betas and I was like, wow, this looks really great.
[00:28:55] And then that was a moment when I didn't even have to do the six week wait. I didn't have to wait for [00:29:00] six weeks. I immediately felt my conviction and the problem kind of go down. It's like, oh, this solves it really well. And then my care in this about the solution went up like I would advocate for this solution.
[00:29:11] And that was when it switched. Like I started to care less about the problem and I started to care more about learning about this one particular solution. And for me that was like, this is a really cool problem. So really cool tool to work on. It's no longer a valuable business. And that's okay.
[00:29:28] Nick: Yeah, I mean, what's so fascinating to me about this is like the ups and downs of, of being a, a founder. It is ul ultimately this very emo it is very emotional and anyone who says it's not doesn't know what they're talking about. I mean, that's my personal opinion. And. What I love about the carer and the way you talk about using it during your journey is it's, it is a f like the F, like the car framework.
[00:29:57] It is kind of an emotional framework, but it's also [00:30:00] like a framework which speaks to the business part of me, right? It's like it's a way to digest your, your emotions about what's happening and. And try to understand them in a more like logical business context. Which I mean, kudos to you. Like that's, it's a much easier said than actually done.
[00:30:22] Anthony: Yeah, so true. It, it's, it's a great way to blend your evidence and your emotion to see like, should I still do, should I keep going with this? Does it make sense? Like, am I just kind of convincing myself with these emotions? Is the data conflicting with how I'm feeling? Is it aligned? But maybe I'm just still trying to convince myself, I'm trying to overthink the problem. Yeah. It, it's, it's, it was super helpful to me to. Take stock of all that stuff and just kind of like, it gave me like a processing framework as well, so I, I didn't just make a gut decision on it like [00:31:00] all the time.
[00:31:01] Nick: You know, so we've been talking a lot about your journey. We've been talking about these, kind of, these frameworks. I think when you, when you think more holistically about the casa journey, you know, are there, are there key moments or forks in the road that you kind of go back to? That determine, you feel like, determine the outcome places where maybe if you had gone down a different path, you, you think you would've ended up in a, in a different place.
[00:31:29] Anthony: Yeah, I think that there were, there are two, and I think one was actually at the outset of casa. If I could have gone back. There was kind of a moment when I was like, I don't have a founder yet. That was a pretty key thing and I really wanted to have a founder, like I wanted to have a a early team because you go faster alone, further together.
[00:31:49] Like that's a real, I think there's a lot of truth to that. And I think if I would've gone back and there was a moment when I'm like, you know what? Do I actually go all in on this thing [00:32:00] called casa? Or do I just maybe start working with teams directly, like doing consulting, doing so trying to learn about their problems very deeply before planting my flag in the sand and saying, this is the product, this is the thing.
[00:32:13] I think that would've been super valuable. So that was a pivot point I think for me and I, I obviously went the route of like, let's go with Casa Casa Dev and then. For the second part, I think it was more of a, just like seeing from another founder who is a dev tools founder. I was asking for some feedback and thoughts on like, how I was going with things.
[00:32:38] Like, look, I'm starting to not feel conviction anymore because of this. Like, I'm thinking about shutting down. And his point was basically like, look. Some founders spend like five years to a decade or more working on something that is a very cool tool, but not at all a viable business. And that was when it was just like, wha like this is that, that's exactly what [00:33:00] I felt.
[00:33:00] And it was just like plain as day. Right. In the email, I'm like, I think it's time to, to shut down and move on.
[00:33:06] Nick: Yeah, I mean, I, the, the, the point you make about co-founders and that early team, I mean, so, right. You know, I mean the, the people you surround yourself with. Is so important. But it's also hard, right? I mean, it's like a lot of that comes to timing, right? A lot to your personal, your personal network, what, whatever it is.
[00:33:29] Um, but just that right combination of founders and then the folks around the founders matters quite a bit. But the other thing that you said, which we haven't talked about before, but which I just, I think about a lot about. In my own journey is like, was it right to have had a concept for the product bef [00:34:00] like first And you know, I feel like that's a really hard one because I feel like what gets most founders excited is you have some light bulb moment about something that like inspires you to go.
[00:34:15] Um, but then you get a, but if that's the world that you're in, you get in this very much in this, this like hypothesis driven testing approach, which is like what everyone tells you around MVP and which is like, oh, we have these hypotheses and we're gonna like test this. Is this product viable or not? But to your point, like if you just consulted with teams, right?
[00:34:39] Or you just gotten really close to teams and just been like obsessive about like, I'm obsessed with this customer and I wanna understand every, everything about their job and what their problems are, and then look to just go solve those problems. It's a very. It's a very different [00:35:00] way starting with the customer before the product, but I just, I wonder if that's actually a better way to build things than the typical way that, that, that, that I did.
[00:35:10] And I think much most founders do. I.
[00:35:12] Anthony: I think it's hard to say if it, if it truly is, is better or worse, but I think there's times when you should be more focused on like the actual specific product or that, that like kind of go to market first. Like, do we wanna test this specific product in the market first or do we just wanna see like what the market looks like?
[00:35:32] Like are we, and I think for that. Some of it's just like you, you really have it. You like have this feeling that you wanna scratch, you really wanna do it. Like you really wanna found something. You already have co-founders, like that's really important. People is like the number one thing, like that early team is critical to to doing things.
[00:35:52] And if you have a really great team and you're committed to each other and you wanna learn some stuff. Try it. Like there's, and you have, if you have the runway, if you're [00:36:00] able to do it, like go work with other customers and then try to explore what's in the market because you might discover something that's outside of your intuition and just gut feel, which is amazing.
[00:36:10] And so I, I think both things can work and yeah, I definitely think both can work.
[00:36:16] Nick: How do you think about the role of luck? Right? Like, and it's something that I feel like we. I think a lot about, hear lots of like very successful founders. The founders that we all talk about talk, you know, they, they discuss the role of luck. Like how do you think about the role of luck in, in personal agency and in in startup life, in either as it reflected itself in your journey or just like in general.
[00:36:43] Anthony: I think a, a lot of it is when preparation meets opportunity. And I think that really shines when you focus on what makes you valuable. So when I think about how luck factored into like Casa, one [00:37:00] really big moment was just like we were doing a lot of traveling for our wedding while Casa was going on.
[00:37:06] Like my wife and I got married and in June last year, and I was like right during like a break point for Casa, like, okay, gonna take some time off. And some of the people that I met during that time actually ended up introducing me to people who had become pilot customers later on. And just embracing that instead of being like, oh, you know, we have to wait.
[00:37:26] Like I can't do this. Like actually embrace it. It makes me unique and special and just like be aware of that. Like always be curious, like always keep that door open to, maybe someone's gonna say, oh yeah, I know someone who's been talking about this all the time at this company. If you wanna talk to 'em.
[00:37:43] You never know when those kinds of conversations are gonna happen, so you have to be open to 'em. And so that's when I think preparation can meet opportunity because, and it's great for technical founders too, because you can iterate really quickly and just build things and get it back into potential users', customers [00:38:00] hands. When you kind of have that product ready to go, to go, you have that idea ready to go, and you're always curious. And someone asks, boom, like, you can like get on a call. Like maybe it's like, you know, in in Europe at like 2:00 AM and you're trying to talk to somebody in like a totally different time zone, but it's like, just do it.
[00:38:19] It's like that's what makes unique and valuable. And someone's gonna see that. Someone's like, oh, this person really cares. They're really trying to learn and like, figure out what they're, what, what's going on here? So I think for me, it, it happened a couple of times for sure. And. I'm really happy that I like leaned into, you know, what was just happening to me.
[00:38:38] Like I can't control everything that's happening around me and I don't wanna say no to really incredible like life moments as well. So it was all about leaning into it.
[00:38:46] Nick: yeah, I mean I, I love that philosophy and I think especially for founders. At any stage of their journey. Like you have a life too. Like life is happening. And there's [00:39:00] a struggle, like how do you fit it all in? How, how do you make it all work? But then the other side of that is like, embrace it all right?
[00:39:09] And like lean into it all because it's, it's a full, it's a full life and one that you can. Live in parallel as you, as you wrote about, you know, this week. And I, I love that perspective of embracing the opportunities that life brings you, within the context of your company and your startup as well.
[00:39:39] Um. Like how, like in general does, you know, founding inform your, your perspective on life or vice versa? Having done it a couple of times now like where do you see that that interact that, that [00:40:00] intersection for yourself?
[00:40:01] Anthony: Yeah, I think like for me, I guess like maybe what it means to like be a founder today, you think? I think like what it means to be a founder today is figuring out, I. How you can really do something in the service of another. I think that's really important. And finding areas where it might be underserved, right?
[00:40:25] Like there's not a lot of people paying attention to something, but you have the skills and you can actually show up and do that. It might not be exciting at first, but again, just kind of like leaning into it, seeing what's there can really make all the difference. Because if you're able to kind of put on like that how like as a founder.
[00:40:42] You're, if you want to take on investors, you're going to serve your investors. You're going to serve your employees, you're going to serve your users. It's very much like servant leadership type of stuff. That for me, like thinking about like you know, I'm married now, I wanna be a dad soon. Like, no, not going to be, want to be, [00:41:00] we're planning, but it's like if you want to, do that, you're doing that in a lot of the service of, of others.
[00:41:07] And so I think that's a very important, like that's how it informs like my life. Like how can I do something in the service of others with the skills that I have? And sometimes you might find it in like really curious places you've never thought of before.
[00:41:19] Nick: Totally. Look, I think that's that service serv, you know, that, that in service of others', mindset is like the, it's the best way to be. And having thought about a lot of this, like in depth myself, having talked to other, like many other founders about it, like. That is like the best core motivation, right? In the end or perspective.
[00:41:43] And I think what's fraught for so many of us is that founding and the journey of founding in a lot of ways is about, can be about more like selfish motivations, right? And. I'll [00:42:00] speak for myself personally, like I have some of that in me, right? I, I try to embrace the servant piece of things, but then there's also these like selfish motivations.
[00:42:08] You want money, you want power, you want fame, you want, you want authority, whatever those things are. And so I, I think that's, there's some element of that is true in, in each of us. But it's gotta be balanced against or by your, your better angels and that. That mindset of service to the people you care about, that gives you perspective on why you do what you do, or that mindset of service to like the customer or the person, you know, the, the person whose problems you're trying to solve.
[00:42:43] Like it's those things that they're gonna probably keep you sane and, probably have you driving your product and business in the right place as well.
[00:42:55] Anthony: So true. I, I'm a student of Seth Godin and he always [00:43:00] like says these two things, like when you're working on a project company or whatever, it's like, who's it for and what's it for? And if you can keep that like always in the back of your mind as you do things. As long as it's like, who's it for? It can always be you.
[00:43:15] What's it for? Always money. It shouldn't always be that, like it shouldn't always be that. It's great if, if it leads to that, but I think coming back to one of the things I wrote about in the post like experience is what you get when maybe you didn't get what you wanted. Maybe you didn't bring the best product to market.
[00:43:30] Maybe you didn't, you know, do the best kind of returns for your investors. Maybe that was really bad there or maybe something didn't quite connect with your team. The point is you have this super amazing wealth of experience you can share with other future founders, or it doesn't necessarily, it could be younger or older, whoever's gonna start something new next, being able to share that with them is such a critical point, and it's super important.
[00:43:56] Nick: So in, in our la you know, [00:44:00] before we wrap in our last five, 10 minutes I have one final question for you. But before we get there, just tell us all a little bit more about yourself. Like, tell us about who you are your background, and kind of your life leading up to your career and, and being a serial founder.
[00:44:21] Anthony: Yeah. So I am a Pittsburgh native. Let's go Penns. Hopefully you make the playoffs this year. But, yeah, I, I grew up in Pittsburgh. I was never, into entrepreneurship or that kind of thing as a kid, was also never into software. I learned to code actually in university, so I, I went to Carnegie Mellon and I was super intimidated.
[00:44:45] Because there were so many students that were exceedingly brilliant, and I was like, wow, I can do calculus, but I can't do this code stuff. What is happening? What is this? And I think that can be quite daunting for a lot of people. Like, wow, like there's already [00:45:00] so many people who are like, so much better than me.
[00:45:01] I could never do something like that. Don't, you know, don't say that. Just try, like, you never try lean into it. Maybe you lean into that fear a little bit, maybe you realize you're really good at it. That was something that I kind of embrace. And yeah, I, I, I grew up, there, I spent a bit of time at DC at Capital One, which was a great learning experience.
[00:45:23] Um, got to learn so much about cloud computing and that was really where I found something that I just loved to do. I was just really into it, loved learning about it, and, yeah, I, I, I also love teaching. Like it was really great to, 'cause when I think when you teach, you learn twice, like you really have to know your material.
[00:45:39] You really have to get into it in order to be a great teacher. I. And so it was really great to, to spend some time at, at at, at CMU teaching a bit as well. So, and, yeah, it, it's I guess that's, that's a bit about myself.
[00:45:54] Nick: When you. When you think about where you go next, [00:46:00] right? When you think about five years from now, do you, do you envision yourself being a founder again? Are you, are you, is are you want, you know, are you casa and done? Like, where are you? Obviously it's all relatively fresh still, but where, where are you there?
[00:46:20] Anthony: Yeah. I think for me, I, I, I, I wanna, I like my energy is a technical founder, like professionally. Like that's the kind of energy I think I bring to a team and that's not gonna go away, I think anytime soon. And so when I think about like future opportunities. I don't wanna focus on founding or not. I kind of wanna take all the learnings that I have and actually like practice what I'm preaching here.
[00:46:46] And I wanna, I'm focusing on two things, people and the problem. And are these people people I can work with for a long time? That's something that that means a lot to me. And also, is this a problem that I think we can work on for a long time together? [00:47:00] So those are the things that I'm evaluating now. And I think that you know, if, if that, if that works out, who knows what it could lead to.
[00:47:09] But, I'm really excited to at some point found again there. There's, I have a super long list of ideas. I think as a founder you should have just keep like a, a Apple notes, however you like to take your notes, just like list ideas, just all the time. It's like, what would, if you do, like, you know, like what was it, the, the branded water.
[00:47:31] A liquid death. It's like, what if you could do that for oat milk? It's like, write it down
[00:47:36] Nick: not that is not a dev tool, but is a good idea.
[00:47:39] Anthony: But, but I think like that, that's super important. So, maybe I'll, I'll, maybe I'll be back in dev tools as a founder. May, maybe I'll be back in founding something else.
[00:47:49] But, that I'm not totally sure that's gonna be the the next thing. But, I think focusing on people and problem is what I'm gonna do.
[00:47:57] Nick: Well, maybe that, maybe that's the answer [00:48:00] to this question, this final question, but if you had to give yourself your, your future founder yourself, one piece of advice, knowing everything you know now, what would it be?
[00:48:10] Anthony: always be closing. Always be curious. Um. I think it, it, it'll go, that curiosity will go a long way. It'll pick you up when you're feeling down. It'll keep you grounded when you're writing really high.
[00:48:23] Nick: Amazing. Well, I think that's a wrap. That's it for today. Anthony, thank you so much. This was fascinating. Uh, please check out Anthony's full writings on this topic, on the not another CEO of Substack and, and Anthony, I think beyond that, if, if folks want to get in touch with you, what's the, what's the best way for people to reach out?
[00:48:43] Anthony: Yeah, I think the best way to reach out is just go to my website. It is just anthony corti.com. There's some links there. If you wanna connect with me on LinkedIn or wherever, just feel free to reach out.
[00:48:55] Nick: Amazing. Well, Anthony, thank you again. Thanks for everyone who, [00:49:00] who's watched this show and for today. That's a wrap.
[00:49:06] Anthony: Awesome. Thanks Nick.
[00:49:07] Nick: Thank you.
[00:49:09]
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