How do you align company success with personal growth? In this episode of Not Another CEO Podcast, David Politis sits down with Diego Oppenheimer, the founder and former CEO of Algorithmia, to discuss his journey from engineer to entrepreneur and the lessons he learned scaling, selling, and leading a company.
Diego shares his philosophy on hiring for alignment, navigating the emotional rollercoaster of being a CEO, and how he successfully positioned Algorithmia for acquisition. He also provides insights into enterprise sales, fundraising, and why finding the right investors and employees is key to long-term success.
Takeaways:
The Power of Finding the Win-Win: Diego explains his hiring philosophy of aligning company and employee goals. He prioritized candidates whose personal growth goals matched the company’s mission, ensuring stronger retention and culture.
Managing the CEO Rollercoaster: From reassuring employees to handling crises behind the scenes, Diego reflects on the emotional toll of leadership. He shares how CEOs act as buffers, absorbing stress to keep teams, investors, and customers aligned.
Early Customer Wins & Enterprise Sales Strategy: Algorithmia’s first customers came from a mix of content-driven PLG motion and conference networking. Diego explains how startups must “get on the field” to win enterprise deals.
Scaling Yourself as CEO: As the company grew, Diego transitioned from closing every deal to focusing on high-impact interactions. He shares his approach to using thought leadership, content marketing, and direct customer engagement to scale influence.
The Role of Investors & Board Dynamics: Not all investors provide the same value. Diego breaks down how he leveraged board members effectively, categorized investor types, and ensured expectations were aligned for mutual success.
Positioning for Acquisition: Diego shares how Algorithmia’s strategic focus on machine learning deployment made it an attractive acquisition target for DataRobot. He explains how they navigated the M&A process in just 45 days.
Quote of the Show:
“Sometimes the worst day of your life and the best day of your life are the same day, just different hours.” - Diego Oppenheimer
Links:
Twitter: https://x.com/doppenhe
Ways to Tune In:
Spotify:
Apple Podcasts:
Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261
Transistor: https://podcast.notanotherceo.com/
Chapters:
0:00 Intro
1:21 What You’d Do Again As CEO
09:01 The Importance of Team Dynamics
16:00 First Customers and Go-to-Market Strategy
22:41 Scaling the Business and CEO Involvement
27:23 Customer Obsession and Tactical Initiatives
30:43 Exclusive Roundtable Discussions
32:08 Challenges with Large Customers
37:17 Navigating Investor Relationships
40:53 The Acquisition Journey
47:29 Emotional Rollercoaster of Entrepreneurship
51:10 Family Influence and Entrepreneurial Roots
56:25 Current Ventures and AI Focus
58:12 Advice to Younger Self
1:01:47 Outro
Episode Transcript
[00:00:00] Diego: And people were like horrified. Cause like, what do you like, you know, like, it's like, why are you reset? Why would you say that you're going to spook people off? I'm like, no, like if people are spooked off by that, where's the lie?
David: Today's guest is a true innovator and thought leader in the world of data and AI. He's one of those unique people who started his career as an engineer. He's technical by nature, but has evolved to be great at go to market as well. He's the founder and former CEO of Algorithmia. He founded the company in 2013 and grew it very quickly before it was acquired by DataRobot in 2021.
David: He's keeping himself [00:01:00] very busy now. He's an active angel investor. He's on multiple boards. He's advising a number of companies and venture funds and is working on incubating a couple of companies. Please welcome Diego Oppenheimer.
[00:01:12] Diego: Thanks, David. Uh, awesome to be here. Thanks for having me.
[00:01:16] David: I'm excited for this conversation. Um, let, let's jump right into it. First question. What's the one thing that you did big or small? At algorithmia that had the biggest impact and you'll do again if you're CEO of another company in the future Which my bet is that you will be Hmm
[00:01:36] Diego: overall, I think one of the things that I've, as I reflected over the years that, that, that I was really happy that I did was, um, something I called about kind of like aligning incentives, uh, on, on both sides of the game. So, uh, especially with like employees and kind of team members as they join. One of the things that I thought was the most important was like, what are they getting out of the experience at working at Algorithmia? And what is Algorithmia getting out of [00:02:00] them, you know, of the experience of them working? And so, and, and I thought it was really important to kind of like take some time. To make sure that those things lined up. So everybody talks about kind of culture fit. They talk about kind of like a skill set and these are all very important. Um, but I really, really cared about this like alignment and the people that I had the best alignment with were the people who stayed the longest at the company. Um, and it was kind of like a, a big part of how we. Kind of like grew the culture. Um, we used to, you know, one of the, the, the, the basic, uh, kind of values of the company that, that we always said is like, uh, you know, uh, find the win, win, right. And so like find a win, like, you know, and I've said this multiple times before, probably a lot of people laugh.
[00:02:41] I say, I was like, I think zero sum games are lazy. You know, if I have to expect you to lose for me to win, that's a lazy way of looking at it. Win win situations are actually a lot harder to find, but they're much more rewarding. Either it be with your customers, either it be with your employees, either it be with the other team members, your board, your investors. And so a big part of it was like that kind of like. Always trying [00:03:00] to find alignment, but in particular with employees at the company that, that I thought was like, you know, I would absolutely do that again. And I would be like, just as a pain in the ass. Everybody used to laugh at me for, for, for doing this over and over again.
[00:03:12] And so I do it again and be more pain in the ass doing that.
[00:03:15] David: I look for I literally I love that value finding the win win I'm not sure that I've heard anyone else with that value before and I I think that it's um, it's a really good way Of summarizing successful relationships to your doesn't even matter if it's with the employees, with the investors, with the customers, with the partners.
[00:03:40] Um, I, I, I love that. Can I let, let's go a little bit deeper on this specifically as it relates to the employees and hiring. How did you actually do that? I mean, tactically, how, how did you actually figure out if there was the win win?
[00:03:55] Diego: Yeah. So, you know, we, so I, I was probably the last [00:04:00] interview on, um, you know, For everybody that started the company, kind of like
[00:04:04] David: Every person, Hmm.
[00:04:08] Diego: we were about a hundred people, maybe a little bit over a hundred, um, in, in the company. Uh, but that means that like, you know, 200 people went through the company over its history, maybe, you know, maybe a little bit more. Uh, and I thought it was really important, first of all, that like they met the CEO and they knew like where, you Once you hit this mark, you can't do this. Once you hit this mark, you're not going to be able to do this. And I was like, well, I'm not going to be a blocker, but I do think it's really important, uh, that I get to meet everybody.
[00:04:38] And, and, and I asked the same interview question for years and years and years and years. And I said, know, at this point that they, you know, most of, especially in the end, you know, what people got to me. The decision was kind of already made, right? Like, you know, I, I trusted that my team, that they have, I've added the technical skills and the kind of like, I EQ and the kind of like value [00:05:00] alignment with the company.
[00:05:01] And really what I wanted to do is that final, like, I be able at this company to provide what this person wants, you know, and will this person be able to kind of like, you know, meet that on the other side with the company. And so I always told people the same thing, which is, you know, say, Hey, We're having this conversation.
[00:05:16] You, you, you start tomorrow. That'd be like, David, you start tomorrow. now two years have gone by. Look back. Why is David a better person? What happened in an algorithmia that like made you, you know, for your career, for your, your development, like, why are you a better position than you are right now today? Some people, you know, kind of gave me the BS answer of like, Oh, I just want to make the company successful, blah, blah. And like, that was a bullshit answer because it's like, no, this is about you. It's not about the company. Right. I want to understand why you're going to be better. Right. And because if we can't provide that, then this is not a good fit.
[00:05:55] We're not aligned. Right. But if we can't
[00:05:57] David: Hmm.
[00:05:58] Diego: is going to be a really successful. [00:06:00] Thing, because I know what I need from you, right? I needed you to be a great engineer or a great marketer or work really hard in like FinOps, like whatever it was, like, I already knew what we needed from you, but now I needed to learn what you were expecting out of this interaction.
[00:06:12] And the two years in a startup is a lifetime. And, and, and, and the most valuable thing we have is time. And so like, if we weren't going to be able to provide. environment for you to grow and fulfill your own things. And this is a terribly aligned relationship, even from day one. So that was kind of like how I did that in, uh, you know, in, in, in, in my interview process,
[00:06:34] David: Wow. And, um, you know, I heard Mark Benioff speak one time and he talked about this concept of an employee value proposition, which I had never really heard before. And it has stuck with me because it's kind of what you're saying, right? It's like, this is what we are saying to you as the employee of what you can expect.
[00:06:54] And it's And if you don't, if that doesn't match to what you want, [00:07:00] then don't come here, basically. Um, I, I, I like that. Uh, do you, do you think that people earlier in the interview process on your team knew how to ask that, those kinds of questions? Or was it really left to you at the end of the process to do that?
[00:07:23] Diego: you know, I think people, you know, everybody had their own style, you know, and I tried not to like metal too much and, and people who like, As a company grows, I'm sure this happened to you. Like there's people who've never hired before. Right. And so you definitely have to do training and you definitely have to kind of like indicate.
[00:07:40] And then, you know, as the company got bigger and, you know, we had more structure around, Hey, you know, you, Peter are going to do the, you know, kind of technical interview. You know,
[00:07:51] David: Mm hmm.
[00:07:52] Diego: like, kind of like Mary, you're going to do like, you know, cultural fit and like blah, blah, blah. And so like that was a little bit more structured, but everybody knew what [00:08:00] I was going to ask because it was so repetitive.
[00:08:02] And I always ask the same question. Uh, and then they're also horrified, uh, especially my, uh, HR team. Um, when, you know, uh, cause I would also ask it and be like, Hey, I just want you to know, like, I want, You know, we're going to have a social contract right now, right? You know, once I've done the alignment, um, and this is not something only the CEO could do, uh,
[00:08:22] David: Yeah, you're right.
[00:08:23] Diego: we're going to agree that you're always going to look out for David, right?
[00:08:28] And the best interests of David, right? Obviously we're all going to be honest and legal and all, but you're always going to be, and I'm always going to look out for the best interests of my company, and this is our social contract. So you, there's never going to be disappointment. always going to make a decision that's best for the company.
[00:08:43] And you should always make a decision that's best for you. And we can still find alignment. Right. And people were like horrified. Cause like, what do you like, you know, like, it's like, why are you reset? Why would you say that you're going to spook people off? I'm like, no, like if people are spooked off by that, where's the lie? Like I will 100 percent every single time make the best decision for the [00:09:00] company. Right.
[00:09:01] David: in terms of prioritization, when you were hiring, uh, you and I ran this session for some CEOs, you know, a couple of weeks ago and, um, some founders, and there were a number of people talking about, you know, wanting to find that top 1%, the top 1 percent engineer, the top 1 percent person to add. If I understand what you're saying to me, yes you wanted great people, but you would actually, if I offered it to you, you would prioritize the person who was that win win fit over trying to find the most talented engineer.
[00:09:36] Diego: Yeah. Every time. I mean, I think like value, the value alignment, like obviously like, like there's a, like, there's a minimum skillset required, not even minimum. Like there's a skillset that you want. And like, there's the great. Um, you know, those, you know, everybody talks about the 10X engineer. We definitely had 10X engineers, but I had 10X engineers, but like, were the best ones were not only like a power themselves, but they actually powered [00:10:00] everybody around them. Right. And so like my definition of a 10X engineer, I got spoiled. The reality is I got spoiled. I, um, my co founder, who's also been like one of my best friends for a very long time was one of those, like, you know, 10 X 15 or whatever, like just absolute cracked person, like developer. And like, you know, so I knew what good looked like, right.
[00:10:23] And, and, and it allowed me to kind of like, understand that, like, Hey, plus people who know how to play in that team environment, the people who kind of like, you know, can themselves with like, you know, the people around them. We'll actually boost everybody up. And so that boost, is actually just as powerful as what one individual could do. So then if I'm looking at it and say, okay, I mean, just to, you know, to play around with numbers, oh, this is an 8X engineer, whatever that means, right? But they are like 8Xing their people around them versus like the 10X that just 10Xs themselves or whatever you want to call it. Like I'll take the 8X all day. [00:11:00] Right.
[00:11:00] David: Hmm.
[00:11:01] Diego: and so, because it's, cause, cause like there's, there's a power in these as, especially as organizations grow, um, you know, you've run really large
[00:11:09] David: Yes. Yeah.
[00:11:10] Diego: like, like that ripple effect that people have around them is so much more powerful than what one individual can do. Uh, and so that alignment to me was insanely important.
[00:11:21] Like, I wanted to see that and, you know, everybody's obsessed with the best of, right? The best of, the best of. It's like, well, of all, like a lot of this stuff is like, best on what? Well, what's, what's the, what's the metric? What's the
[00:11:33] David: Hmm.
[00:11:34] Diego: Like lines of code,
[00:11:35] David: Hmm.
[00:11:36] Diego: you know, deliverable, like, you know, solves hard problems.
[00:11:39] I mean, sure. These are all can be metrics, right? But how about like lifts the organization, right?
[00:11:44] David: Hmm.
[00:11:45] Diego: powers, you know? Um, I'm a little bit like biased in this like I've played rugby my whole life and it's interesting because it's really hard to have like a star on a pitch like on a rugby pitch.
[00:11:55] There's like 15 players and they're all kind of like just as relevant as any other
[00:11:59] David: [00:12:00] Hmm.
[00:12:00] Diego: like it's not like in football you have like oh there's a captain there's a quarterback and the
[00:12:04] David: Yeah.
[00:12:04] Diego: in like there's just a don't hear about that. I mean, of course you have like star players, but it's like impossible to win without the entire team coordinating.
[00:12:12] And like, you know, especially on, like you're saying on defense, like you got to trust the person to your left. You got to trust the person to your right because you can only cover amount.
[00:12:20] David: Right. Right.
[00:12:22] Diego: I, I've just always thought that that team play and that like, kind of like way to work with each other and understand that you're on a mission together was way more important than individual, uh, talent, individual talents, important.
[00:12:35] Don't get me wrong. But like that alignment was like just as important.
[00:12:39] David: I think, I think the lesson that you're saying, which I, I do think the way you put it is great. It's like, you can be the 10X person. It doesn't mean that you're the 10X. On your own productivity. It's it's when you can 10 X the team, as you're saying that what's going through my mind is all those people that I've worked with that are the 10 X.
[00:12:59] [00:13:00] There are very few of them. I would actually say much fewer of the 10 X that can 10 X the team than the 10 X individual contributor. You have the sales rep who's like the best rep by 10 X when they become manager, they don't have that same ability. And I actually think my lesson as you're saying this is like, I probably didn't spend enough.
[00:13:21] time, money, energy, resources to make sure that those 10x people on the team 10x, like that I did everything in my power to keep those people. Like those are the people that it's almost worth any amount of money, right? It's almost worth any amount of money, time, title. It's like, those people are, they can really change the trajectory of a company.
[00:13:46] You know, even a company of a thousand people, you get two, three, four of those. They can change that trajectory.
[00:13:51] Diego: Yeah. And it's like the, the, the thing it's so first of all, a hundred percent agree. And it's also like the, the rubric, it matters here. Right. Because I [00:14:00] just saw, you know, people that were just so much better, you know, like, so let's take the sales rep. Like I had a sales rep who. Um, hit the top numbers, like never hit the top numbers.
[00:14:12] Like he wasn't always, he wasn't like, he was never the best at like selling. Right. But he was absolutely the best at talking to marketing and giving the feedback that was necessary from the field and talking to the engineering team and learning what was going on, like with the product and building it out.
[00:14:30] And like, we probably, you know, literally from like the conversations and his interest in like. What we were doing, Like legitimately was like making the entire company better. And like, he was still selling, I'm not, don't get me wrong. Like, you know, made his
[00:14:44] David: Yeah.
[00:14:45] Diego: you know, like, I'm not like, it's not an excuse to like, not make your number.
[00:14:48] No, he's just not the top. And like, he didn't have the
[00:14:51] David: Mm
[00:14:51] Diego: I could just look at the ripple effect of like what this person was doing in terms of like, You know, I mean, I saw this, like engineers wanted [00:15:00] to talk to him. Like, what does the engineers ever want to talk to the sales team?
[00:15:02] David: hmm, mm hmm,
[00:15:04] Diego: Like, Oh yeah, tell us more. What is the customer saying? Like, why do they not like this? Like we create this feature. Why is this a problem with this? And like, there was such a dedication to like really understanding the problem and caring and stuff like that. And you guess what, when stuff like went really bad with an account, who jumped on, like, like the
[00:15:19] David: mm hmm.
[00:15:20] Diego: immediately, right? Yeah. We'll go help out blah. Like, you know, we'll definitely go help him out. Like, are you kidding me? Like, you know, like, so like, it just creates this environment of like incentive alignment where like, you just get so much more. And so this is where I have a, I have a personal reaction to this. Like, I'm going to, I only hire top 1%, top 1 percent of what,
[00:15:39] David: Mm hmm. I like that. Um, one of the things I said in the intro, you know, when I met you, we just recently met and we were talking about stuff and I, I, I thought you actually came from a go to market background, not from an engineering background. Um, and so, Let's as we start [00:16:00] transitioning to go to market. I want to the question I've been asking guests recently, because a lot of people have been asking me to ask it is, where did you get your first five customers?
[00:16:10] Like, how did you find the first five customers?
[00:16:13] Diego: um, the first five customers, let's see. So, so we had like a little bit of a, uh, you know, kind of like a, like a split history in like, in terms of like. started out as a very developer focused product. And so it was kind of like a PLG motion. We found developers, it was all done via content. Uh, you know, we, we put out blog posts and examples and tools.
[00:16:35] And so like, it was very like towards a developer audience that wanted to learn how to use machine learning inside building their apps. over the course of history of the company, we ended up. You know, moving much same product, but much more focused on an enterprise. So kind of like, I'll, I'll give you the story of the first five customers on both sides, very, very
[00:16:57] David: great, great.
[00:16:58] Diego: very, very different ACVs, [00:17:00] you
[00:17:00] David: Hmm.
[00:17:01] Diego: like, um, the first five customers on the kind of developer side were like, Purely via content. You know, we realized early that like the people like us, me and my co founder, like lived in Hacker News and that like, you know, getting a cool post on Hacker News was what people were going to read and they got started and they would want to use these products and so we just spent a lot of time creating great. some things that like look forward that were, you know, could be controversial that would like spark a discussion and high quality, and then show how to use the product, which is, you know, right now, like 3000 guides of how to do that, like every single developer product you see on earth, like focuses on content because that's why, you know, developers don't want to be sold to, they want to read, they want to understand, they want to build, they want to play, and that's how you get them.
[00:17:47] And so we onboarded like, like our first spark was directly through content, you
[00:17:51] David: Wow. And just to be clear, this is content you and your co founder wrote yourselves.
[00:17:56] Diego: We were writing like, you know, we, we knew on day [00:18:00] one that we were going to like live and die. You know, based on the demos we built. Right. And so we went and built cool demos and, you know, that was, that was it.
[00:18:10] And, uh, now, uh, you know, I work with my, my, my, my co founder on, on his company, he's a CEO now, and, uh, and I'm helping him out and it's like, we, we joke around, we say, we, we, we call it GIF driven development, Which is as we develop things for the, for the vote, we actually publish GIFs. and we show, Hey, this is the product working here.
[00:18:29] And this is the product working here, because that's what developers want to see. Right. They want to see the product in action. And so we didn't invent the term by the way, but like, I love it. It is a gift driven development. It's just like snippets of what you're doing and showing it out all the time. On the enterprise side.
[00:18:43] Um, I didn't know anything. Okay. Like my background, I came from Microsoft, uh, but I was like deep in the engineering org, right? So I had no exposure to like real selling while I was at Microsoft. You know, I had been building enterprise products. for, for a long time while I was there, [00:19:00] I, you know, I would argue I knew nothing about enterprise sales, uh, when I started like absolutely nothing.
[00:19:07] And I kind of brute forced my way into it. Um, The first customer we ever got, we closed, uh, which was Merck, uh, which is kind of a
[00:19:20] David: Wow. First,
[00:19:21] Diego: yeah,
[00:19:21] David: a big customer.
[00:19:23] Diego: Um, was an intro via VC. One of our VCs made an intro and they're like, Hey, one of these kind of like CIO, like things that, Hey, like, you know, this is actually even before we had transitioned into pure enterprise, you know, mostly enterprise
[00:19:36] David: Hmm.
[00:19:37] Diego: Um, and, um, we just got a believer. Um, you know, um, and, and, and the head of this, of research group that, that had a problem and we understood the problem and we understood how to solve the problem and I think he just saw in us as like, these guys are going to go and live and die on this mountain, like helping me out and I have to solve this problem [00:20:00] and I haven't found anything on this is interesting and I'm going to give them a shot and we'll be
[00:20:03] David: Hmm.
[00:20:04] Diego: for that shot for ever right in history because it kind of kicked off. You know, once you get one and you kind of generally understand what it takes, you can get the second one, the second customer, which was Nike. Uh, so, uh, yeah, we, we were taking down some, like some injury was actually again, like We got a champion inside a team that thought our cool, our tech was just really cool.
[00:20:26] He's just like, he
[00:20:26] David: How did you get the intro? How did you get the intro to them?
[00:20:29] Diego: were at a, it was Kenny and I were at a booth. we, we, you know, we, we, we, we manned a booth at like a random like AI conference and they came up to us and they were like, He was the first skeptical and then started, you know, trying to like, see, like, if like very typical in the like engineering world where it's like, let me see if I can like make them trip up. And, you know, and, and so he was just kind of like trying to see where he would trip up. And then, you know, did it tell that like my co founder Kenny wasn't tripping up and he wasn't tripping up and he wasn't tripping up and he's like, [00:21:00] I kind of want to try this then. He's like, okay. And so like, we started that conversation and like later on that turned into like a thing. beyond
[00:21:08] David: Was that the first conference you ever went to? Was that the first?
[00:21:11] Diego: so we started going to like conferences pretty early in our, in our, in our history. Um, a lot of them were like, you know, you know, my co founder came from an academic background. Um, I had been in an industry. And so, you know, we, what we, what we knew as a conference was like, you know, he knew about poster sessions and I knew about these like mega Microsoft conferences.
[00:21:32] Right. And it's like the middle was like an unexplored ground for us, but we were just like, you know, we, we, we would just travel and we would just. And like the attitude that we had was you can't win a game if you're not on the field. And so we're going to be on the field and it doesn't matter that, like, you know, you're an engineer or not, like. You're out there and trying to get this, like, you know, the software, you're, you're, you're, you're, you're always evangelizing. And, uh, you know, I used to travel to all these [00:22:00] conferences with a small booth or whatever I could get for free because we had very little money at that point. Um, and like, honestly, I remember it finally because I had, um, you know, these oyster, like, it was like the big, like, like the, like the, uh, the, um, the, the, the, what are called the cases though? They're unbreakable cases. Are they called
[00:22:18] David: Oh yeah, yeah, yeah, yeah. Um,
[00:22:20] Diego: Uh, sized one. And I had a monitor and a laptop in there, which had our like system as a demo. And I literally traveled with that thing. Like, I don't know how many thousands of miles across, like, like the
[00:22:31] David: uh,
[00:22:32] Diego: like in the first couple of days, and it was awesome. Uh, but yeah, I, I think like the first couple of enterprise sales were just like, you gotta be on the field, like, you're not going to do it from home. Like,
[00:22:41] David: and, and as you, as you scaled the business, um, in a lot of ways you became the face of the company and, and you know, that you really were a big driver. I mean, for I sounds like [00:23:00] even for a while, in terms of being a big part of the sales motion. Can you maybe talk about how you scaled yourself? You know, over time as you actually hired a sales team and all of that, how were you involved in the, where did you play in the process?
[00:23:14] Diego: so, so I was lucky that, you know, so, so I, in the beginning, I thought I had to do everything and that's always the wrong answer. Especially like if you're, if you're hiring, right, then it's 100 percent the wrong answer. Uh, you know, and, and if you are doing everything as a founder, then you might need to re look at your hiring practices, right.
[00:23:36] To go figure that out. Um, like, from my perspective, the most important thing was, was to one, which is understanding that you could, you're the CEO of a company in a pretty new space. In this case, like, you know, AI was, you know, it still is, but you know, fairly new. We're talking about, you know, 2013, 2014 to 15, 16, right?
[00:23:57] Like, uh, pretty innovative area [00:24:00] where, you know, I knew quite a bit about. been in the space. I was in the trenches every day. And so being able, like people wanted to talk to me, right. And, uh, and like, that was, that's a good thing, right. Because if people, nobody wanted to talk to me, like it would have been a lot harder, right.
[00:24:15] To open doors. So once we understood that people wanted to talk to me or wanted to listen to what I had to say, or at least the perspective of what I was seeing in the market, um, we could use that to open doors, And, and, and, you know, eventually, you know, I'm, I'm, I'm fast forwarding a lot, right.
[00:24:32] David: Yeah.
[00:24:32] Diego: my, uh, my last CRO before we sold the company, who I learned a ton from, um, you know, it was like, Hey, we need you to like open and we need you to close the deal or do everything in the middle, right?
[00:24:46] And, but people want to talk to the CEO. They want to see that you're still involved. They want to see that you are willing to go talk to the customers and sit down and hear their problems and share your perspective. And like, there's a level of, [00:25:00] no matter how humble you are, like, there's a level of admiration that people are going to have for a CEO in the space that they care about.
[00:25:07] And so like, let's use that. Right. And like, and, and, and kind of. Think about what are the things that you can write. And, you know, I did a ton of content and I had my marketing team help me generate this content, but it was always under, like, most of it was under my name.
[00:25:20] David: Mm hmm. Hmm.
[00:25:22] Diego: about like, there's a persona that you're building because ultimately business, I don't care how deep your software is, like it's still humans. Right. And go back to that alignment thing, which is like, how do we get, you're going to trust me with your company's business, you're going to trust that I'm going to work my ass off to like make you, you know, my software work work for you, bring the value and all that stuff. That relationship needs to be kind of like created.
[00:25:48] So like showing up as a CEO matter, Even as you scaled. And
[00:25:53] David: Hmm.
[00:25:53] Diego: the question on you, like you've scaled many businesses, like it
[00:25:57] David: Yeah, a
[00:25:57] Diego: Right. I mean like that interaction of like
[00:25:59] David: hundred [00:26:00] percent.
[00:26:00] Diego: like, you know, no matter how big the company is, like, like. It always matters.
[00:26:04] David: It always matters. My biggest surprise was how much people would want to meet with me. Because I always, I would always like, who am I? You know, who, why does it matter? And I had, I had someone say something to me one time, one customer who at the end of the call, they said, Dave, I just want to say, thank you for doing this call with us.
[00:26:25] We work with a lot of vendors and I can't think of the last founder That got on a call with me to ask my feedback. They send their sales team, they send this and, and it was, that was a moment that clicked for me of, I think the way you're describing is the right thing is like, I'm the person building this product, dedicating my life, everything, the company to make this product work for them.
[00:26:54] And. Actually showing up and asking them like to talk to me and what that [00:27:00] was that that makes them feel special that makes them feel Heard that makes them feel part of the company. So I Yeah, actually I would say the more time that went on I actually got more and more time to do that because it becomes it's hard.
[00:27:13] It's you know, 100 employees at 200 It's kind of hard and It can be so, so impactful.
[00:27:21] Diego: Yeah. I think like, you know, it's a cliche. Everybody's be like, says be customer obsessed, uh, be customer of that. But it's, it literally, you have to be customer obsessed. Like, like, I don't see a world where this works, where are, you know, like you, you have that like obsession. I remember even like, so we did like free lunches on Wednesdays, right.
[00:27:39] At the office. And like, I had a little sign on the lunch table. It says, remember who pays for lunch. Right. And it's the customers, right. At some point it was the VCs as well, but like, that's not important. Like, like, like, you know, but like, it was like, I think like the message was important thing is like, we have to be like, and I'm not saying the customer's always right or anything like that, but we got to understand that, like, [00:28:00] we are a company, we are a
[00:28:02] David: We exist for the, we exist for the, yes.
[00:28:04] Diego: and that is, you know, to serve our customers and to
[00:28:08] David: Yes.
[00:28:08] Diego: whatever they need.
[00:28:09] That's it. Like, there's no other. Like, you know, like all the other purposes can be true, but they're secondary.
[00:28:15] David: Can you give me a tactical, a tactical way that you, like a campaign or initiative that you, that used you as the centerpiece in
[00:28:30] Diego: and I think actually, uh, our friends over at, at Workbench were the ones that, uh, you know, taught me this, uh, which is, uh, the use of, um, roundtables and, and bringing in people into roundtables and not selling them anything. And so I think this is probably one of the most successful things that we did over the history, which is we could get. You know, I would do a nine person round table, right? I would be like insanely strict, no salespeople, [00:29:00] just me, no marketing, nobody, you know, the team wanted to like, the team didn't really like this. Uh, but you know, know, quiet place, actual
[00:29:09] David: person,
[00:29:10] Diego: yeah.
[00:29:11] David: in person.
[00:29:11] Diego: actual nine round table. an actual round table.
[00:29:16] I, I was important and I would pick a subject and I would invite the top executives that I could get to that meeting. And so, for example, like if there was a conference, uh, about, you know, of a pharma conference, I would go and try to get like, head of machine learning at Merck, the head of machine learning at Pfizer, the head of machine learning at AstraZeneca. And I would invite them and I would say, Hey, Chatham House Rules. Nobody's recording this. There's no notes. There's no sales. There's no marketing. I promise I won't pitch you absolutely anything. We're going to talk. About what machine learning problems pharma is facing right now.
[00:29:57] David: Hmm.
[00:29:58] Diego: And the [00:30:00] first couple, and by the way, I ended up doing some of these in zoom during the pandemic and it did work as well, as well.
[00:30:05] I do, I prefer them person, but I did do them during the pandemic and zoom. And I just became this moderator of getting, so first of all, I was shocked at the fact that I got like competitive. people, you know, I did a
[00:30:19] David: In the same room, in the same room,
[00:30:21] Diego: table, like I did a finance one and I had JPMC and Bank of America and Citi and, uh, you know, they were all, you know, they, they, and they were the head and they were First people are a little bit shy, but then you start, I was the moderator.
[00:30:32] I started probing them. It's like, you're not revealing secrets. First of all, nobody's talking about what are the problems here? Hiring, how are we going to get this? We can't get models in production. We can't do this. We can't do that. And they were amazing. Like, it was like some of the coolest like conversations I had in history.
[00:30:48] And then I made them very like exclusive in the sense that like, If you were a good participant, I'd invite you again. And if you were not a good participant, I'd probably like try to get somebody else people [00:31:00] were like begging me to get in. Like, like these executives are to call me like, Hey, when are you doing your next one?
[00:31:04] This, that was, that was the best round table that I've ever been a part of. Like, how do I get into this? I'm like, Hey, you know, it's like nine people only. Like, you're going to
[00:31:13] David: right? And
[00:31:15] Diego: this thing where like, that was by far probably one of the best, uh, you know, things. And the reality is with those executives, I still talk, you know, I've sold the company three years ago. still talk to them. I still catch up with them. I catch up with them in cities. moved around between like, Same industry, but like different companies. So like you can keep on, you know, when these people, you know, you, you, you take the time to listen to their problems, what they're good, what they need, and you're not shoving, you're trying to shove your toy down, you know, your software down their throat. You will learn a lot. And so that was kind of probably like the biggest lesson I learned in the go to market world, which is like, just shut up and listen for a while and then create environments where people want to talk. People want to talk about what they do. [00:32:00] Everybody does. Absolutely
[00:32:01] David: to the win win right there in that roundtable. They're learning, they're advancing their career. It all ties back to that. One of the things, you had crazy low, I mean crazy customers from early on. If you look back at that time, would you have gone day one for such, you know, the Mercs and the Nikes like, because I I have had a hard time with those size customers, you know, and I, and a lot of companies I work with have a hard time with those size customers cause they really, they're used to dictating everything.
[00:32:39] Um, and, and, and could hijack the company, you know? Um, so how, how did you, did you do that on purpose? I guess is question one and two, how did you deal with that?
[00:32:50] Diego: not do it on purpose. Like absolutely not. Like, like I, you know, it's not planned at all. Like that would just be like. A lie. If I said that, like, I was like, Oh [00:33:00] yeah, I like targeted this company. It went to them and like, just not true. Um, they were there and they had the problem that we were solving. And again, it came down to like, where the places where we found the champions that wanted to take a bet on a company like ours and looking back, this, this is a point of debate. That I have incessantly with my, with my, my ex co founder on this. And it's like, should we have done this company or not? Like, there's some companies that like one could have argue, like threw us off. Right. And you know, like, and there's like pivotal moments of like, Hey, what would have been different if we hadn't done this, or we hadn't wasted time on this, right?
[00:33:38] Because that's ultimately like the biggest problem you have with going after these large customers is opportunity costs. Like, like that's really what you're managing, but everything's a butterfly effect, right? Like the fact that I had the Mercs and the Nikes got me the next two. Right. The fact that I had like, you know, these others is the way.
[00:33:55] And so I, you know, I, it's, it's, it's, I keep on going back and forth. [00:34:00] Like, yes, there was moments where by the end of the journey, I was a lot stricter and I had a lot more backbone to push back on these customers. Right. And so like the situation was a lot better, but you know, I can't say I wouldn't go back and do the same companies again, because like, all the Maybe we wouldn't have had a company at that point.
[00:34:21] Maybe we've never had an exit. Like, we wouldn't exist. Uh, and so, um, it's kind of hard to like, Scalpel your way through like a point in time and be like, Oh, we would just change this and everything would have been perfect. Right. It's just not true. Um, I think we got a lot better at, uh, holding, um, the other side accountable and we got a lot less, you know, it's really, really, really scary to fire a customer, like, and you, and like, sometimes you, I'm sure you had to do it.
[00:34:54] David: Yes, yeah, it's the worst, worst experience, yeah.
[00:34:58] Diego: how dare we, [00:35:00] right? Like, we're trying to build something from scratch, like up. And like, we have the gall to like, say no to a customer. Like, like, who do you think you are? Right. And like, that's how I thought. Right. And, but no, you have to develop that backbone. You have to understand the fit. Um, you know, where you're, you know, where your ICP matters and like how to build around that. Because. Um, it's a really difficult thing to do. And it's probably like, you know, again, I go back and forth, you know, I think one thing that I can say, I probably want to, you know, I'll give you a good example, like I think our third largest customer in the big, like, so I gave you two, I'm not going to mention what the third, let's say the third one was a government agency,
[00:35:40] David: Yeah, everyone will know who they are, yes.
[00:35:42] Diego: And, uh, and, uh, your third enterprise customer should never be. A government agency, unless you are an absolute government expert. And I was not, and I am still not today. Uh, and, after going through a nightmare [00:36:00] there, like legit nightmare, would we have ever gotten the JP Morgans?
[00:36:04] David: Right,
[00:36:05] Diego: don't know. Maybe not. Maybe, maybe not, probably not. Right. And so like, that's kind of the, there's this butterfly effect around that, that I don't really know how to. at this act, I know that like individually could be like, that was a bad idea and that was a bad idea. And it costs us a lot of pain and there's a lot of opportunity costs.
[00:36:22] And if I went backwards, know how to, I'd know how to contain it, I think.
[00:36:27] David: mm hmm, mm, mm.
[00:36:29] Diego: feel a little bit more confident. So I probably would have done the same decision making, but with a lot more understanding of what I was getting into. And because of that, I think I would have been able to contain how much opportunity cost we took on, because of doing that. So a little bit of a non answer. Hopefully
[00:36:46] David: No, no, no, that's a good no, no, that's that I think I think that's you know for me I think that the it's it's this challenge of if you can land the big fish, you know, then what do you do with it? but if you can land [00:37:00] it and be successful as Referenceable customers. No one can say like, oh you can't handle my size account You can't what's your security look like you're like I'm working with people who care more about security than you ever So like, you know, um, so let me, let me ask another question.
[00:37:17] You know, you, you raised money from, from a number of investors. Um, as you think about that, was there something that though, like, where was the value that the, that your investors brought, if any, to, to the business? Yeah.
[00:37:36] Diego: different stages, you know, so we raised, you know, a, you know, of traditional path of a pre seed, seed, series A, series B. And then we got acquired right before our series C. And, uh, or like halfway, we were like out raising our series C. I think investors, uh, there was plenty, you know, there was insanely good investors.
[00:37:58] Um, people [00:38:00] like our, our, you know, like our, our seed investor, uh, which was Madrona, Tim Porter. Um, I can call them out directly, like was like with us the entire time. Um, and. trying to be, you know, I always say like, um, best quality is he knows what he knows and he knows what he doesn't know he kind of stays out of what he doesn't know and just tries to be helpful in that case and like was just completely supportive throughout the entire, you know, history of the, of, of, of the company. Um, in other cases, you know, we had investors that came in and gave us like, Great leads, right. And because they had like, you know, a CIO summit and like, they were really well connected. And, you know, if you, you have to learn what the quality of each investor is and what they bring to the table. And in some cases you just have to understand that all an investor does. Is bring cash and cash is green and they're irrelevant and it's okay. Right. Just don't, you know, again, that goes back to like, you know, the, the, [00:39:00] like the social contract of like expectation management, like if I bring in this investor and I think they're going to bring all this value and they don't, our social contract has been broken.
[00:39:10] Right. But if
[00:39:11] David: Yeah. Yeah.
[00:39:12] Diego: doing is bringing cash to the table, is fine. I need cash.
[00:39:16] David: Right. Right.
[00:39:17] Diego: I expect then, you know, no, no, no harm, no foul. And so I just really think it's just like, you know, I, I, I think it's really important, very, very important to pick your board members well, and I think your, your, your, your board members, you know, a good board member, you know, there's three categories of board members in my, there's like the great, right, which like. Increase the value of the company, really coach the CEO and really help out. And sadly, like, I think like that's like 1 percent of board members, like maybe a little bit more, right. And, and they're insanely rare. You know, I, I hope that one day I can become that board member. I'm in a bunch of boards. I hope one day I can become that board member. [00:40:00] Like I really do. I think like the biggest category is the like, Hey, they're sort of helpful, but. Kind of like, uh, you know, like no harm, you know, no harm is done. And like, you know, help you think through things, help you do that. And like, they're, you know, and they're there. And then there's like a category of board members, which are actively detrimental to your company. Uh, and probably every CEO who's been around long enough has had. At least the bottom two categories, the like no op and the, you know, and the, and the bad, the great is a lot, you know, they're, they're, they're a lot less, uh, you know, common. Um, you just got to avoid that bottom, you know, that bottom because they can be so disruptive to the company.
[00:40:38] They can be so problematic. They can be so dysfunctional to, a board. And, it really matters to cross references and be like, understand what you're getting into, right? Because it's the one position you can't really Remove, or it's very, very difficult to remove.
[00:40:53] David: Um, when, so you, you ultimately sold the company, um, in [00:41:00] 21. Was that, you mentioned you were fundraising during that process. Was that you were starting a fundraise process and out of the blue came an acquisition offer, or was that something that was being nurtured? Was there a partnership there? Like, how did that come about?
[00:41:14] Diego: Yeah. So I had, um, every single time I'd gotten into a raise ever since like our seed round, I tried doing a market check on like what our value was.
[00:41:28] David: Hmm.
[00:41:29] Diego: Our exit value was right. And so I actually ran like, like company sales cycles, not quite as much as a sales cycle, but at every round, like, which was like talking to the teams, trying to figure out understanding where we were. Um, it was an insane amount of work and kind of crazy, but I kind of like, you know, I think like my co founder and I were always like, look, we should always know what better way to understand. Like if we should move, you know, every time you take money, you move the goalposts. [00:42:00] And in some cases you move the goalposts by a lot, right?
[00:42:05] And so we always thought, hey, we should better understand, like, we should understand like where we are today, what the value is. And what the other side of the market sees, because like, should we be moving these goalposts so much? Like, you know, we believed in the business, we believed in what we were doing. Uh, some people would suggest, I see this online a lot, it's like, never even think about a sale because you're mentally not prepared and you're not going for the moon. This is business, right? Like we're looking at, we're doing like, you're supposed to be doing risk reward calculations on a daily basis all day, right?
[00:42:36] David: Yeah. Yeah.
[00:42:36] Diego: just another risk rewards like, uh, you know, like calculation. so, um, To go to that, that thing, like we had always run sales processes. We were kind of like in this particular case, we had been talking to a couple of our current customers who weren't going to invest in the company. And we, you know, this is very specific to the company we ended up getting acquired by, which is, um, we [00:43:00] saw from a go to market perspective is, um, in AutoML, which is like, uh, what DataRobot did was bought us, um, they produced a lot of models because it's a tool that literally produces a lot of machine learning models, but they were having a really hard time putting those models into production.
[00:43:15] They're kind of like they, and we, you know, I noticed that like. Anybody who used their product, we could
[00:43:24] David: Oh, wow.
[00:43:28] Diego: you're doing all this and you have a bunch of these models. You know, I used to call it the, uh, models in a drawer problem. You have all these models in a drawer, you're not putting them in production.
[00:43:36] We put models in production. Why don't you buy us? And they had a competing product to ours, but it was like smaller and not as figured out and stuff like that. And we were like, so we just started chasing those customers uh, we started chasing them, chasing and chasing them just from a go to market perspective. And I guess what happened internally, this is the story I was told by, you know, it was like one of their VPs over there was [00:44:00] like, keep being beat by this, little ass company, like in all these deals for like the infrastructure of how to run our shit. Like we should go buy them or figure that out.
[00:44:14] And so we got an inbound, uh, from, for, for the acquisition for, for that acquisition, uh, that was like brokered by one of the, one of our VCs. And, uh, interesting because essentially at that point, I, I essentially, I'm fast forwarding through a lot of like, You know, the typical, uh,
[00:44:32] David: Yeah.
[00:44:33] Diego: flamingo dance between the two parties of like, I like you, I don't like you.
[00:44:37] Like, are we going to talk? Are we going to play together? But like the fast forward is essentially like I told the CEO, um, I was like, look, I'm in the middle of a race. Like, can't pay attention to this. Cause you'll like screw my race. If you want to go do this, like we got to go fast we actually did the entire. Acquisition in 45 days clock time. [00:45:00] Uh, a hundred, 85 people went over.
[00:45:04] David: Wow.
[00:45:06] Diego: so like, it wasn't like, like it was like, I mean, you've done a couple of M& A, so you
[00:45:09] David: Yeah, yeah, yeah, yeah.
[00:45:10] Diego: Every lawyers on both sides called us, the CEOs, absolutely insane. And they like, were like, there's no way, there's no way. And like, we just made a deal that like, this was the timeframe because anything else wouldn't work.
[00:45:23] And so, you know, it was probably like the worst 45 days of my life, I mean, emotionally and like, emotionally. Just exhaustion. And like just the amount of hours that I had to put into this. Um, but you know, um, and run the company and not tell anybody except my
[00:45:37] David: Right. Right.
[00:45:39] Diego: and, and just be a zombie in general.
[00:45:41] And, but yeah, we, we, we, you know, we, from, from, from interest, you know, from, from LOI to close, it was 45 days. And, and that we, that we kind of like sold the company.
[00:45:52] David: And were you running the Series C process in parallel to that? Or you had in
[00:45:57] Diego: Yeah.
[00:45:57] David: kind of
[00:45:58] Diego: we had essentially, I mean, like the, [00:46:00] the reality of it was like, this is 2021, right? Like, um, you had to be growing at 300%. You know, year over year, which is like a fantasy at this point. Nobody does that. Right. Like, uh, uh, at that stage we weren't under that, but like, we were still growing like decent amount above a hundred percent growth year over year. Uh, and, uh, you know, but we were like, kind of like, and so the real, the decision here was like, okay, we were going to raise this, you know, we're confident we're going to raise the series seed. But it wasn't going to be the like 3x multiple on our previous valuation, which is like the typical, like, I don't know, typical, it's like, you know, that, that kind of metric that you
[00:46:34] David: Yeah.
[00:46:35] Diego: like, Hey, you know, double, you know, triple, triple, triple, double, double IPO, kind of like general metric on how you look at things. And, you know, we weren't going to triple, you know, we barely were going to get to a double, uh, on valuation, but we did have like our biggest Customers writing us the largest checks, which was like a very big show of confidence in what we were doing, which I thought was kind of cool. So yeah, halfway through that series [00:47:00] C and then at that point, understanding that, like where we were going to move the dilution, where are we going to move the, you know, the goalposts to. We've been doing this for a number of years already. Um, there was, you know, the outcome could, you know, it's going to be significant for a bunch of team members
[00:47:15] David: Right.
[00:47:16] Diego: like, you know, that was ultimately kind of what drove us to, to sell the company.
[00:47:20] David: Wow. Um, what is the biggest challenge you've ever faced
[00:47:25] Diego: Honestly,
[00:47:27] David: was the biggest challenge you ever faced at the company?
[00:47:29] Diego: like, you know, I tell people, um, the, you know, the, the, the entrepreneurial lifestyle is sinusoidal, uh, Which is so like, you, you get these like ups and downs and, you know, sometimes the worst day of your life and the best day of your life. are the same day Just like different hours And that rollercoaster was probably the hardest.
[00:47:53] Right. So like in general, like, know, uh, a pretty like, like, like highly wired person. [00:48:00] And so like, I have a lot of energy and I like to like, and like just the emotional rollercoaster and managing the emotional rollercoaster. For home, for the team, for investors, for customers. And like, you know, you're going to the team and being like, Hey, it's all good.
[00:48:15] And everything's fine. And then like, you know, picking up the phone and calling my co founder being like, we're f***ed Like, how are we going to get out of this? Like, you know, like that was probably the hardest part, just kind of like managing the, you know, like the thing, because, you know, and I know you've seen this all the time, like we, you know, there's, there's a near death experience every other week. in running a company, but they never play out. If you shared every single one of those near death experiences, everybody be freaked out. Right? So you are actually the buffer of that. Like, you know, that's what happens. You know, this, the, the, the emotional rollercoaster is like wild. And you as a CEO are the buffer of that to everybody around it, to your investors, to your customers, to your employees so you're [00:49:00] absorbing it. And I think that was always like the hardest part for me, which is like, I was absorbing this like wild rollercoaster and trying to be. Like, you know, zen and calm and like keep mission straight. And it was the right thing to do because. If I had shared every single time I thought the company was going to go under from day one, we would have never achieved what we achieved.
[00:49:20] David: When I was, when I was really early, like 25 years old, really early in my career, I remember we, we had some terrible stuff happen at this company and I was running and, and, uh, and I remember I was in my office, there was like a whole glass wall, everyone could see in it, and I was like my head in my hands and I was, and someone came in my office and they're like, is everything okay?
[00:49:44] I'm like, I mean, it's been one of those days or whatever. And they said, well, just so you know, everyone can see you. And now everyone thinks like the company's shutting down or, you know, everyone just assumes the worst. And it was that moment. I remember it [00:50:00] like today, it clicked for me. I'm like, wow, my, even if it's a personal thing, even if it has nothing to do with work, it actually doesn't matter if I am showing.
[00:50:09] Any emotion, people are going to mirror that emotion and they're going to read into that emotion. And I think that's when you're saying what you're saying, it's like one thing to absorb it. It's another thing to absorb it and be the buffer from everyone else. And, and it's, that is exhausting.
[00:50:27] Diego: Absolutely. I, I joke around. I mean, I loved my role and I love being a CEO. And like, I, you know, I, you know, I think it's one of the most like, you know, uh, It's one of the greatest jobs, but I don't know why I like it kind of thing. Like, and like, you know, and I, and I joke around and I tell people, I was like, the only people who wanna be CEOs are the ones who've never been CEOs before. Uh, and
[00:50:48] David: Yeah, right.
[00:50:49] Diego: because then you learn your lesson. But no, it's this weird kind of like, was the hardest thing and like such a hardcore job. And like it was so crazy [00:51:00] intense for a bunch of reasons. And I wanna do it again,
[00:51:04] David: Yeah.
[00:51:05] Diego: a little crazy, I think.
[00:51:07] David: Um, well, let, let's actually talk about this. So, so if we go to your background, um, did you, have you always wanted to be an entrepreneur, always wanted to be a CEO? Like, is that in, is that in your DNA? Is that in, did something happen early on that drove you to that?
[00:51:25] Diego: Yeah, I, I don't know. I think, I think like if I go back to like, you know, kind of DNA, like my family has been like entrepreneurs, maybe not in the more traditional sense. Like, you know, I come from Jewish immigrants, you know, who like rebuilt, you know, like fled, you know, Germany and Hungary and Bulgaria and rebuilt their lives and I grew up in Uruguay, so they rebuilt their, you know, they rebuilt their lives in Uruguay and they were. You know, had clothing stores and like, uh, you know, electric business, you know, electrician businesses and stuff like that. my parents came to the U S to go to college and [00:52:00] then they ended up starting a company together. I mean, not really like, so they, they brought McDonald's to Uruguay, like as a joint venture, my dad and my mom, uh, put all their savings.
[00:52:09] They, my dad worked
[00:52:10] David: What? Holy
[00:52:11] Diego: and they, you know, they, they put all their savings into this bet of like, we're going to go take like thing, which is like fast food, hamburgers, which didn't exist in the country. And we're going to go build a, you know, we're going to go build this in Uruguay and they did, and they did it successfully.
[00:52:26] And they like grew it to be one of the largest employers in the entire country. So from that perspective, I did see what. Like entrepreneur is going to like, look like,
[00:52:35] David: wait, they came here for, they came to the U S for college
[00:52:38] Diego: Yeah. They did their, yeah, their MBAs. And then they moved back to, they worked here for a while. And then they moved back to Uruguay with us, me and my
[00:52:45] David: to start.
[00:52:45] Diego: to start, yeah, McDonald's in Uruguay.
[00:52:48] David: And do they still run that? Do they still?
[00:52:50] Diego: my dad happily. My dad is like, well, uh, my mom's happily retired. My dad is. Figuring out what retired looks like still. He's like, no, like this is like 20 years ago. I think that, [00:53:00] you know, they, they, they, they left that business. My mom's done other stuff in marketing since now is happily retired, taking care of her brand new grandson. And, uh, and, uh, my dad still does kind of like consulting for entrepreneurs and kind of, uh, you know, boards and stuff like that, he's still kind of like. Working, uh, knows their operations really well. Uh, but, uh, yeah, they're on the
[00:53:21] David: So you grew up, you grew up around, so you grew up around that. And you, do you think that that, did you just want to be them one day? Like, is that,
[00:53:31] Diego: the one, um, the one thing that I appreciate most, so, you know, they worked, you know, my parents worked like 20 hour days the entire time I was growing up, the only thing I saw, right? Like it was this. Very insane. Like, uh, you know, I have grandparents and stuff like that, but like, you know, around, but like, it was really crazy.
[00:53:50] Like the amount of hours I worked to, you know, run like an organization, you know, that big and kind of, and, uh, and stuff like that, I think I appreciated [00:54:00] building, right. Building something from nothing. Right. And I thought that that was always a really cool thing. And I always loved tech and I knew I wanted to start something. Um, I never really, I never thought about being CEO. I just knew I wanted to start something. Right. And, and, you know, one of the things that I thought was like particularly cool and was just takes a lot of inspiration, I think, on the values that I kind of like around alignment and stuff like that was, you know, 20 years later, after like my dad's been done with this, you know, we could be walking around like Uruguay and he'd get stopped on the street by somebody who'd like worked for him and be like, you gave me a chance, you know, I grew from, you know, I, you know, I had just a high school diploma and then I could work here and now I got this job in the management and blah, blah, and like, that was because like. Your company existed. And like, I had that opportunity and I thought that was like, that's what winning looks like, in my opinion. Right? Like, I thought, I looked at that and I was like, okay, that's what winning looks like. If I can get an effect of people coming [00:55:00] years later, right? And saying this opportunity that you gave me the trajectory of my career, like that's, that's it, right?
[00:55:09] Like that, that, that to
[00:55:10] David: hmm,
[00:55:11] Diego: right? And,
[00:55:11] David: hmm,
[00:55:12] Diego: I go back to that alignment thing, you know, it's kind of like full circle. Like, I think I learned that from them, uh, and you know, they cared a lot about that. And like, I think that's like, you know, If you, uh, if you really think about building stuff that's going to have, you know, uh, real, uh, you know, kind of like, uh, you know, kind of like, I don't know what to say, like legacy.
[00:55:30] Legacy sounds kind of like a little pompous, but like, you know, real meaning, right, is like you can create these things as entrepreneurs. It's this beautiful thing where you can create these organizations. that, you know, build cool shit, provide amazing experiences, you know, to people working there.
[00:55:47] And that actually changes lives from, again, from a career perspective. I'm not saying it's like, you know, you're going out there and there's plenty of things that change lives. But like, you know, something I could do. Um, and so that was kind of like where a lot of the inspiration, so I think it's more around that, like, I [00:56:00] love building high performing teams and like, you know, kind of like, uh, these, these opportunities where people can grow and like, I want, like, I love that.
[00:56:09] David: what, um, what are you doing now? I mean, I, I said in the intro, you're definitely very busy. You're one of the busier people, probably, um, you know, who's not a CEO. What, what are you, what are you doing? What are you planning on doing? Hmm. Hmm.
[00:56:25] Diego: I love everything that has to do with like AI and data. I've been working in that, you know, for 25 years and like, I joke around, it's like, we're at the Superbowl. Right. Moment of AI right now. And like, I actually think like, we're like, maybe it's like, I don't like baseball as much, sorry to offend anybody, but like, maybe it's like first game of the world series is a better thing, because I think we're in the first inning of like AI, but we're like at the, you know, kind of like the most critical moment that we've ever seen is kind of like, For some of us who have been in the space for a very long time, this is the best time ever, like, to be alive, And to be in this industry, right? Like, I really, I mean, like, look at everything that's every day. [00:57:00] It's like, oh, my God, something new. Um, and so, you know, I've focused on being involved in that. Um, Part of it has been as a, you know, part time venture partner at, you know, Workbench, which, where we met, uh, part time at, uh, you know, Innovation Endeavors, which is, uh, you know, a different one that focused on that part.
[00:57:17] And a lot of working with different CEOs have been advisor or board member. Uh, as an independent board member in a number of AI companies and what I get, I, you know, I just get a lot of enjoyment out of helping people build their thing. Uh, and, and, and, and kind of helping out and, you know, I joke around, I say, I can't tell you what the future looks like.
[00:57:40] I don't know. I can't tell you what to do, but I can tell you what's not working. And so I can focus a lot of time on that. So I've been working with a bunch of different entrepreneurs. Uh, I, I've been lucky enough that like, they've let me into their companies. They've let me participate in their journeys. And so a bunch of my focus has been on helping others build their thing. Uh, you know, [00:58:00] now, um, while staying at the like absolute, You know, kind of tip of the spear in terms of like AI.
[00:58:07] David: Cool. What, um, what, knowing everything you know today and all the experiences you've had, what is one piece of advice you would go back and give yourself at the very beginning of your career?
[00:58:21] Diego: Very beginning of my career. Um, let's see if the very beginning of my career. So I think like, um, nothing's as fatal as it seems. Like, I think I, I, I, I stressed a lot and I gave myself a lot of anxiety because I didn't understand, like, what You know, um, well, how to think through consequences and like what it could be.
[00:58:44] And so, um, I went through this exercise halfway through, uh, you know, my, my time at Algorithmia like where, um, it was kind of like a CEO exercise of being like, what's the one thing you're doing today that has the biggest effect. On what can [00:59:00] you, on the company three years from now. And it was interesting because when I took that perspective and I kind of zoom out, right.
[00:59:08] Um, a lot of shit because it goes away. Like there's a lot of this, like, you know, your list of problems, suddenly you're like, what's going to have an effect on the company three years from now? And it's like, can cross 92 percent of it out and you end up with that one thing that's important. And so that's probably one of the things, um, you know, that I would, um, you know, do and tell myself that's kind of on the negative side on the positive reinforcement. And this is something I actually like learned from my dad, um, was take every single opportunity and think of it as what skillset you're going to learn in this next opportunity. What is the skillset acquisition that you're putting yourself through that this is going to, so any job, any career move, any, uh, you know, entrepreneurial thing that you go follow, like, what is it for you personally?
[00:59:59] Like, what [01:00:00] skillset are you going to learn and how's that skillset going to make you better? Two years from now, right? That's actually the other interview question that kind of
[01:00:07] David: Yeah, yeah,
[01:00:08] Diego: there, which is like, what, you know, what, why, why is this going to be a step function for you? What are you learning?
[01:00:14] What's the skill set? And do you want that skill set? And if you want a skill set that you don't have, go find the thing that's going to put you In the position to go learn that skillset. So, so I did do that. I feel like every single career move I ever did my life, I did follow that and I would kind of go back and reinforce it and say like, this is probably the best decision you made. Uh, that, and don't worry as much about things. So
[01:00:36] David: I like that.
[01:00:37] Diego: two.
[01:00:38] David: I think, you know, the don't worry is an interesting one because I feel that's been a pretty common theme with a number of multi time kind of entrepreneurs or operators or whatever of the highs are not as high as you think they are. The lows are not as low as you think that they are. And it goes back to what you said [01:01:00] about that, the journey and going through it.
[01:01:03] It takes a long time to learn what you just said. I wish I had that advice. I, I truly wish I had, but even if you had the advice, it's like until you live it, you still think, you know, that this thing is going to kill you and this thing is going to be the biggest deal you've ever done in this. And, um, I think that is such, If there's one thing, especially because people go through that motion, like just to know, like, yeah, you think that's the biggest deal ever?
[01:01:31] You think it's going to close tomorrow? It probably won't. And it probably be a quarter of the price that you think it's going to be. And this thing that you think is going to kill you, probably it's going to either go away or you'll figure out a way to deal with it. That's not as, you know, and, and, um, so I like that.
[01:01:46] Um, if people want to get in touch with you, if they want to get your advice on their company, like what is the best way to, to reach you?
[01:01:56] Diego: Um, email, um, um, diego. [01:02:00] oppenheimer at gmail. com. Real easy. Uh, LinkedIn just, uh, hit me up on LinkedIn. Uh, mention. That you heard the podcast, 'cause I get a lot of LinkedIn messages, so I'll filter through that. I promise I'll respond, uh, uh, on that. Um, but yeah, I mean, if you're working on something interesting in AI and data, uh, and or wanna just chat, I'm, I'm always happy to, to meet with entrepreneurs, uh, all the time.
[01:02:23] I love that.
[01:02:24] David: Great. Diego, thank you for doing this. Um, um, I, I appreciate it. I think in this episode specifically, I think we got pretty actionable and tactile, which I appreciate. Like and you gave people things they can actually go and do so thank you for for sharing and um and for giving back
[01:02:43] Diego: Thanks for having me. Uh, I love doing these with you. So, uh, you know, uh, and looking forward to working on something together over at, uh,
[01:02:50] David: Yeah Awesome. Thank you. And for those listening, I hope you enjoyed please Please share this with your networks like subscribe all of that and uh, we'll see you on the next [01:03:00] episode of not another ceo podcast
