He thought his startup would fail—then grew to $100M ARR. | Rick Song, Co-founder of Persona

Rick Song (00:00:00):
I think if you're going to do a startup. I think one of the worst mentalities have is, what I often come to call like a min-max mentality. In which everything has to be the most optimal choice. Startups by default is a wildly un-optimal choice and a life career decision. The reality of it is, no. It's really just kind of, a journey and exploration. It's a personal decision at the end of the day. I have seen this a lot. In which I think a lot of founders have a tendency to self delude into believing like, oh, as long as they just keep on doing it, it'll work out. But while they think that, they also aren't actively trying to prove that it's going to fail. They're not really trying to seek out truth. And I think a lot of times for early stage startups. The stress and this pressure of needing to succeed. Almost, you know, it's like self-defeating. It will actually destroy you just because you have so much pressure on yourself.

Previous Guests (00:00:47):
That's product market fit. Product market fit. Product market fit. I called it the product market fit question. Product market fit. Product market fit. Product market fit. Product market fit. I mean, the name of the show is product market fit. 

Pablo Srugo (00:00:59):
Do you think the product market fit show, has product market fit? Because if you do, then there's something you just have to do. You have to take out your phone. You have to leave the show five stars. It lets us reach more founders and it lets us get better guests. Thank you. Rick, welcome to the show, man.

Rick Song (00:01:15):
Hey, thank you so much for having me.

Pablo Srugo (00:01:16):
It's over the last seven years or so. You've grown Persona to like a multi-billion dollar valuation, raised over $400 million, over $100 million in ARR. So it's become a huge success and on its way even bigger. But we'll talk today really about kind of the early days, right? What, how and why? You started Persona in the first place and how you got things off the ground. So anyways, maybe take me back to your background before 2018. What were you doing? And then we can kind of dive into how Persona came to be.

Rick Song (00:01:46):
Yeah, for sure. So prior to all of this, I was an engineer at Square for about five years. My co-founder and I are both engineers. So my co-founder is over at Dropbox, working a lot on the data infrastructure side of things. I'd been at Square working on fraud, risk, identity. You know at that time, what we'd really seen was. I would almost say, a disconnect between what we needed as an entity versus what a lot of the market was offering and what they would say from an identity-solutioning perspective of what would solve our problems. So, you know, at that time. Working on a lot of these problems, you'd talk with various vendors. A lot of these vendors would promise you some sort of silver bullet saying like, this is the one silver bullet to solve all your identity problems. Fraud would disappear, you know, very extreme claims. But the reality for us as a business and how we had to build things. Was we had to incorporate all these various signals and make them kind of tailor it such that really makes sense for exactly our use case. And we have to do this for all these different types of products within Square as well. So my team there, a lot of our work at that time was building out identity solutions that would not only work for a single product, but Square was emerging as this entire conglomerate for all sorts of different kinds of services. Anywhere from, you know, back then what it was best known for. The Square white card reader, into cash app, into business banking, into lending and more. So with us on those ends. That's kind of where we saw an opportunity to build an identity platform that could really service any type of use case out there. So Charles, co-founder, was my roommate at that time. You know, he'd always had more of an entrepreneurial spirit than I did. But he was pushing a lot on like, hey, we should do something together, right? We live together right now. He's one of my best friends. And I've worked a lot on the identity side of things about kind of, that combination of ideas and, an entrepreneurial desire was kind of what birthed Persona. And this is back in 2018.

Pablo Srugo (00:03:38):
What stage was Square at when you joined?

Rick Song (00:03:41):
So I joined, oof, I can barely remember. Maybe, actually funnily enough. Probably to a similar size at exactly what Persona's at now. So I think it was about 300 something people. Either Series C or Series D, I can't exactly recall.

Pablo Srugo (00:03:56):
And you come right out of college? That was kind of your first job?

Rick Song (00:03:59):
First job right out of college. You know, you've done a couple of internships here and there. But yeah, never.

Pablo Srugo (00:04:04):
And walk me through. For people like me, we're not necessarily identity or fraud experts. Maybe just make it tangible. You think about Square, obviously you're dealing with these, you know, with payments and all that stuff. There's going to be those issues. But, what is under that? Like, when you say identity. What is the main problem and how does it surface up?

Rick Song (00:04:21):
The common way, especially for a technologist. When they speak of identity is usually they think of it from the perspective of access. So that would be something like, logging in with your email, things like that, right? And that's one perspective identity, but that's not the perspective identity that Persona really deals with. When we talk about identity. We think of it much more actually from the intuitive sense from a physical perspective. Like, when I ask you, what's your identity? You don't tell me, oh, it's your email. You'll say it's Pablo, right? If you ask me, I'll say it's Rick. We're looking for the identity that is kind of the publicly recognized, the government issued identity, the physical identity of the person. Another way I oftentimes talk about it is, you know, I may have many Reddit accounts. I have many user email addresses, right? I have all sorts of digital identities. I only have one physical identity, right? At least within, you know, the current limitations of technology. Maybe AI will change that, who knows, right? But today I only have one physical identity, and that physical identity is the one that Persona fundamentally helps companies resolve. We're the ones who are trying to help businesses be able to figure out, who is it behind the screen. Who's the physical person that actually is representing this overall interaction. And that entire pursuit, is challenging primarily because it's largely probabilistic. You hear all the time about digital identity theft. You hear about people impersonating others these days. There's deep fakes, all of that, and the reality of how you have to solve that problem is actually that there's not a silver bullet. There's not a single solution. There's not a magical way to just be able to say with absolute certainty, every single thing out there has a bypass. In many ways, actually, the problem becomes more of a security problem than it is just a strict technology problem. So a lot of our work can be anywhere from anti-fraud to compliance, from trust and safety, you know, to ML and AI. Trying to triangulate with sufficient probability for the use case a customer faces. That this person really is who they say they are, and making sure that's hopefully as seamless as possible for us as the end user. We can make sure that the data is treated with absolute sensitivity. These days you hear all the time about businesses having data breaches and otherwise. Our goal is to make sure that the next time you have to be yourself online. It is easy as putting in your credit card information in which you just don't think about it. You don't really, you know, when you're making a purchase on Amazon these days. When you make a purchase on any sort of Shopify store. We don't worry anymore that they're going to leak our credit card information. That this purchase is going to be, all that. It feels like a very safe transaction. I think today identity doesn't feel that way. When you put in your personal information, you feel as if your data, might get stolen, that someone might take it and impersonate you. And ruin your credit score. God knows what kind of, sort of interactions. Our goal is to restore and make a digital identity infrastructure that feels safe. That's seamless, that the next time you do anything here, it doesn't feel like a risk. It feels like a minor inconvenience the same way as making a purchase online.

Pablo Srugo (00:06:58):
And I mean, this is probably another stupid question. But from a layman's perspective, you say there's no silver bullet. But on mobile and Face ID, as an example. Like, is that a silver bullet for the mobile use cases? Or is there some issues even to that? Or is that just a subset of kind of identity the way you're talking about it?

Rick Song (00:07:12):
So it's a subset of it, and the way I often describe that is. That face ID may be able to tell you that it's the same person. But again, our challenge is not about is it the same person? The fundamental question we have is. Who are you within like some sort of registry? Who are you as recognized by the government, right? So even though I could face ID into my phone. It doesn't know, and I can make it so that my name right now is. I mean, any sort of name out there, right? Tim Smith, God knows what, right? Any name, and that isn't, you know, sure. For my own self and test identity, some people may appreciate it, right? People have monikers, people have usernames, all sorts of things. But for a lot of the businesses and the use cases we fundamentally work with and support. The thing they're most interested in is who are you as recognized by somebody else.

Pablo Srugo (00:07:52):
So when you're working in fraud and identity at Square. You know, your co-founder comes to you and says, you've got to do something here. We're very high level, right? Identity fraud is, a big idea. But what's the thing that you see that others don't? Or what's the wedge that you start with?

Rick Song (00:08:07):
So, we had a vision from early on and that actually never changed. And we worked backwards from the vision. We didn't really start it from like, oh, you know, and I think this is one of the aspects of Persona's founding story that is a little bit maybe strange. But one thing I oftentimes tell folks is literally from day one, we've never really pivoted. We've never, like, our long term vision was almost crystallized even before our MVP. That long-term vision is today, and it will sound somewhat obvious. But it's like today, when you verify yourself in one place, right? You've probably put in your, personal information on various sites. You've probably had to submit a government ID, sometimes perform a biometric check. For all sorts of application science, you've probably done that in some way, shape, or form. However, the reality of today's status quo is that, you have to do that over and over again. And every single company does this in isolation. And the way we oftentimes talk about this is that. If you're a fraudster who create a, fake identity at one store, you know, most of the time what they will do is, they'll ban you and say, no more. You can just go right next door and use it again, and there's no sort of defence. And then for us as, good actors, as folks who have genuine intent. We are forced to go through the exact same kind of like process, and what's even worse is that even from the start of Persona. Over the past five years, the amount of friction, the amount of effort to do that has not only decreased, it's actually only increased. We're watching the complication of how to be ourselves online, get progressively worse year by year. So the vision of Persona was the long-term cannot be that every single business is establishing this. Individually, the long-term has to be that there's a way in which we can own our personal information. Make it easier with higher credibility, and be able to operate in a network-based approach in which when you verify one place, it should be easier at the next place. Even easier at the subsequent, and there should be some sort of lines there. So once we had that as this long-term vision that identity can no longer be siloed. But there should be some sort of global backbone and ideally consumer controlled data with. You know, and also for businesses making sure that their data is also managed securely. We work backwards from there of, well, how do we make such a vision come to reality? And the first thing that we had stumbled on, is we have to at least build the universal processor. Oftentimes there are a lot of businesses, you know, I've seen the space for quite some time. There are a lot of businesses who would issue kind of new credentials. They'd be like, Hey, here's this new identity thing. If everyone opts into it, then. You know, I guess the infrastructure could be better. But that's really a chicken and egg thing.

Pablo Srugo (00:10:30):
Yeah, cause that was my first. Everybody kind of becomes a Persona verified and then Persona becomes the thing with everybody else. That was kind of, that was where my mind originally went when you're talking with this.

Rick Song (00:10:38):
It's the common one, right? But the challenge there is twofold. One of which is as end users. We don't opt into anything unless, you know, there's intent. The second is that different types of use cases have different problems. For example, if I was ordering alcohol, I need to verify that I'm over 21. You know, that could be a very seamless kind of process. But on the flip side, if you're applying for a loan for over a million dollars. You can't use the same identity that you just proven with for alcohol. It would just be the level of diligence required for these two use cases are really different. So, our perspective was then what you really need first and foremost is a processor. You need to make it such that all these companies, there's an interoperable kind of processor on the other side for businesses. In which every business, you know, another way to put it is that every business day accepts credit cards, right? Whether swipe or tap, there's a protocol effectively now in which every business can kind of accept. We have to first build effectively that card processor. We have to first build the backbone that all companies kind of have a universal language of how they accept a digital identity. And then that point, you can gradually start layering in various forms of digital IDs that can be interoperable and universally acceptable. So much of our work hasn't really been on the consumer side. It's actually a lot more about working with businesses to create a processor layer with the hope that long-term there's an opportunity such as consumers, right? Like, everyone's speaking the same language now around identity. Another analogy I oftentimes make is, it's very similar to Visa, MasterCard network. In which, if it weren't for Visa or MasterCard. We'd still be, either paying in cash or doing something in which every single company is issuing their own payment credentials, right? That payment method is only accepted within that single entity. But because we have a network payment system, risk is lower, friction is less. Everything's a little bit better, because our payment ecosystem has made it such that we have some sort of transferable risk.

Pablo Srugo (00:12:23):
How do you? The value of a Visa or MasterCard is very clear. The merchant gets a purchase they might not otherwise have gotten. Because that person doesn't have money today and, a bunch of other things that it kind of just facilitates. Lower friction, whatever. What's the original value prop? Once the network is there, whatever, you know, just today it's just so much easier. Everybody, you start selling something, you're obviously going to accept Visa, MasterCard, right? But even in the beginning, it was still useful to be able to accept any form of payment. What is that kind of wedge value prop for you at the beginning? Why does anybody? Why does any business decide to work with you and spend the time building out that protocol?

Rick Song (00:12:59):
Also, actually. I mean, you hit the nail on the head, right? It's the exact same fundamental value prop. Which is greater access, less friction, or less fraud. Making sure that one of those three is always true for any of our customers. So whether that be, we have broader coverage, we're able to process an identity faster than somebody else, or with lower friction with a better user experience. Or we're able to deter more fraud on behalf of the end customer, and ideally all three all at once for our customers. So that was a lot of the early value proposition. Which is how can we build a system that would enable that for our customers? At the time when we had first started, a lot of that evolution was happening in the world of government IDs and biometrics. So already there are a lot of services out there in which you had to upload a government ID, and when you upload government ID. What ended up happening in those sort of situations for a lot of the status quo at that time was, you'd have folks overseas manually looking at these IDs. And this could take anywhere from a couple hours to many hours, right? Sometimes multiple days, even.

Pablo Srugo (00:13:56):
What's an example, by the way, of this use case? I mean, the alcohol one. Could be one alone, things like that.

Rick Song (00:14:02):
Yeah, but I mean even. Let's say in 2018, there were all sorts of, new crypto exchanges. There are all sorts of fintech applications. All of whom who, you know, if you're building a new fintech application in which you're onboarding recent immigrants. They're not gonna have social security numbers, they're not gonna have access to, a lot of these things. So oftentimes, the only way in which they could verify themselves is their government ID. Identity infrastructure, especially from a data perspective. Across the world is incredibly still, I mean, immature. Sometimes we think that the government has this massive database. All these governments have massive databases in which they know everybody. It's just not true, in reality, actually. These, you know, if you think about these legacy infrastructures are incredibly outdated. One of my favorite kind of just fun facts about this. Is that back in the day, social security numbers weren't random. In fact, if you're born I think prior to 1991 or something. Your social security number is, the first five is identified by the location of where which hospital you were born at, and the subsequent four is actually just an incrementing number. So you can actually, if I know how old you are, plus where you were born. I can actually pretty much guess within maybe, let's say 100. Within 100 numbers what your social security number is. That's how insanely accurate it would be.

Pablo Srugo (00:15:14):
Not good security to have at all.

Rick Song (00:15:16):
Right! This is the backbone of all of our identity security at this point, right? So, a lot of our work was trying to secure all three of these, right? Helping modernize it, make it such that, you know. So from a Government ID perspective, our big bet in the early days was, is it possible we could fully automate it? And full automation, first off meant it's a better experience for the end user, it's faster, right? You're not waiting days anymore. You're waiting a couple of minutes, or actually for us, it was a couple of seconds. I think even our first iteration was, I think, 20 something seconds for processing. And then two, you know, we had a big bet that technology will continue to improve such that. And also that fraud will continue to improve in which humans will probably be outperformed by algorithms, right? Already for so many forms of computer vision based stuff. Computers were starting to outperform human review. So we're like, this is probably likely, right? And the third is if we can make this experience better for everybody. It means that every single company have broader access to more end users. So, that was our first wedge, and then after that we continue to expand. Because we knew that government IDs, you know, you can't just say, oh, image based processing would be the end all be all. You know, there's a lot of other use cases out there. So we started platformizing pretty much from the earliest days. Again, I think that was an unorthodox decision for us. A lot of times I think the general advice for startups is, pick a niche and then win your niche, and then expand from there. But we went very aggressively in terms of, not actually like just purely capitalizing on our niche and actually kind of going a little bit wider. Because we thought the core of identity isn't solved by, again, that silver bullet. That single solution, but rather pulling in more and more data points. So we work towards passive signals, like behavioral signals, you know. Behavioral signals being ones in which while you're kind of going through a flow, making sure that you're not a bot, making sure that, you know, your behavior isn't automate things like that. Looking at network risk, looking at a lot of hidden risk signals, then pulling in more data source and just continually padding it out. Because our goal was never to automate government ID or biometric verifications, right? Not making us, you know, our goal is always how do we solve identities? And by keeping that as kind of the North Star. We never really got overly attached to any specific technology and instead always focused on the problem.

Pablo Srugo (00:17:22):
So we'll dive into kind of where you took it and maybe some of the first customers. But just going back in the story. So you maybe just first question, you're working at Square. You said, you joined when there are a few billion. I mean, it was a pretty solid growth story. How would you tell yourself? Walk me through that, right? Like the thinking, it's one thing to talk about starting a startup. It's another thing to actually leave the thing that's really working well and take the big risk. What was that decision making process like? And at what point did you feel comfortable that? Yeah, okay, you know what? Let's leave this thing and let's do this. You know, high risk, high reward journey.

Rick Song (00:17:56):
Well, the first is, I. You know, the joy of being a bit younger is I had. You know, I didn't have too much responsibilities in life. Which helps a lot.  I think the biggest thing that actually made it feel okay was that we had zero assumption of success. I mean, when I had left. I haven't, had messaged my old manager that I'd probably be back in a couple of months, you know.

Pablo Srugo (00:18:19):
He's still waiting.

Rick Song (00:18:21):
No, I mean, you know, he messaged me a little bit later and I'm like. I think I'm actually stuck on this for a little longer. But at that time, I mean, my expectations were unbelievably low. I don't think I had almost any expectation that this would really go anywhere.

Pablo Srugo (00:18:35):
Why is that? That's the opposite of what most founders are like, this is the thing. This is the billion dollar thing. Otherwise, why would I do it? And if I don't believe it, nobody else will. Do you know what I mean? What drove you thinking about it so differently?

Rick Song (00:18:46):
Well, I guess so. You know, the cheeky answer here is because, I saw the statistics. You know, it's like to me, I used to joke with people. It's like folks who are good, you know, believe that they have a preternatural ability to guess the Powerball numbers, you know, like. I guess maybe. But it's unlikely that you have some hidden insight that. And honestly, when I reflect on so much of our journey. It was a lot of luck. That's not to say, I would say it's 80% luck, 20%,,you know, input, right? It's so much luck that just went right, and it's not just luck from like a, oh, we stumbled on the right idea, the right timing. People who like ended up just in the right situations. The right time of their life who joined us. We would never be here without so many of the early team. And even the team today, all of those folks at that time took a huge risk. And the only reason why they could take that risk was, because we were lucky to have met them earlier in our life. And they were also at this interesting juncture in their life in which they were open to taking these risks too. So a lot of luck, but I think going in with this assumption that we were pretty much almost certainly going to die, and this was just more or less a sabbatical. Helped reduce the stress a lot, and I think a lot of times for early stage startups. The stress and this pressure of needing to succeed almost like it's self, you know, it's like self-defeating. It will actually destroy you just because you have so much pressure on yourself. I've seen so many startups now, these days get the opportunity to sometimes help out with some of these earlier founders going through similar stages and, how often I see them almost beat themselves is incredible. I think actually the hardest stage. If you're talking from the zero to one phase. The hardest stage is not so much, you know, something external. Finding your first customers or all of that. I actually think the hardest, like the biggest enemy you have is really yourself and like figuring out how to deal with. You know, the expectations, the stress and making sure that you're able to continue to press forward, even though there's no defined roadmap. There's no expectations of what's to come, so.

Pablo Srugo (00:20:46):
It's funny that you say that. The thing that comes to mind maybe a little morbid but I remember, you know, all the the war documentaries that we all watch at some point and I just remember this line. I don't remember the exact quote but being like, the ones who survived were the ones that went to war thinking they were already dead. And there was just something about that, you know, just it made you. I don't know exactly what it is. But it just puts you in a state of mind that actually, and it's obviously not perfect by any means. But made you at least what he was saying was it made you almost more likely to survive and to ultimately make it. But you had to truly believe it, and this sounds like something that which is the opposite of what most founders would say. Yeah, I know that only one percent of startups become unicorns, but like, I'm the one percent. Do you know what I mean? Otherwise, why would I do it? And it's just it's a different way to think about it.

Rick Song (00:21:33):
I mean, I think, it's funny that, right? Because, you know, by default if you want to be that one percent, you have to think about something differently. But I think it's funny when, you know, 99. As you were kind of rightfully calling out 99 percent of founders end up thinking exactly what the other 99 percent are thinking. So there's by default, no differentiation and the thought process, you know, it's again. It's, you know, you may be falling into a pitfall immediately. So, yeah, I think that definitely helped a lot. I mean, the second thing that helped a lot, though, was also my co-founder. I mean, he was the one who, from a timing perspective, it wasn't for him. I'm not the type to, jump. He's the one I oftentimes credit to actually being the entire impetus of why the startup exists at all. Because I would have never jumped. I think he would've done a startup almost certainly no matter what. Whether with me or otherwise, he would've done one for sure. I probably would not have if it's not for him.

Pablo Srugo (00:22:23):
And when you do decide to kind of take that leap of faith and you're like. Whatever, I'll probably be back, worst case. Which is actually true. The risk you take if you're a branded company. Especially in engineering and especially back then. Now maybe there's some more risk. It's kind of, worst case, it's a year or two sabbatical and you come back. What's kind of your first move? Do you go out and fundraise? Do you start building? Do you start selling? Where's your head at?

Rick Song (00:22:49):
So back then, I had no idea what I was doing. I mean, if you're too engineered, you just start building. It's the only thing you know. I don't know anything about fundraising. I don't even know who investors are, half these names. I wasn't someone who was very deep in the startup ecosystem. So, you know, half these names. Which is always some combination of, I don't know. A tree or, you know, whatever, right? It's always something you don't. So we start building, actually, as our first kind of thing. Trying to just demo to friends. Try to reach out to friends of startups to, just try to get users. A lot of our early milestones. We kind of have a perspective of, It's going to just die in six months. So this was like a fun little excursion for us, and we had a lot of really early goals that were just really easy. It was like, can we get one customer? Can we get one person to use it? Could someone pay us more than $50 throughout the entire lifetime? We didn't, like, a million seem unreachable, right? Everyone's always talking about like, an ARR. We're like, I don't know. We were reading various things online and it was your path, your first million, and I was like, holy crud, a million? Yeah, let's start with, you know, a couple. If I get $2, I'd be pretty happy, right? Like, will anyone even pay us? So, our list.

Pablo Srugo (00:24:02):
That alone is worth almost pointing out. Because it ties into what you were saying. What does the mindset lead to? And I think if you're the top one percent, then you better be doing a million real soon and you better be getting to 10, right after that. Otherwise, you're a waste of time, you know, it's just not worth it. Whereas if you start with how you started. All of a sudden you're like, I guess let's just do this little thing. And, you know, hopefully one thing ends up leading to another. As it did in your case. But at the very least, you get those wins and the milestones are realistic.

Rick Song (00:24:32):
And I think the other portion for us too was that. The reality of the kind of startup, I oftentimes tell folks. There are a couple of people in the world, a very, very small handful who can will companies into existence. You know, I'm self-aware enough to know I am not one such person. Hey, you know, but there are. They exist and they're incredible, but I'm not such a person.

Pablo Srugo (00:24:49):
You're talking about like a Jobs, a Musk, these kinds of people?

Rick Song (00:24:52):
Yeah, right? Well, you know, these repeat founders, multiple billions every single time will be a hit, right? It's you know, it's an astonishing ability that they have. But again, that's not one percent. That's a point zero, zero, zero, zero, you know, percent. Most of us end up becoming, a combination of luck and right timing and, right mentality. I think a lot of, again, the earliest risk is the aspect of self-defeating, you know, like doing something in which, you know, you are self-destruct. But as long as you can avoid that. Then it's just really kind of a probability game of did you get lucky? Did you pick the right idea? You know, the markets lined up and then continue to kind of progress from there. 

Pablo Srugo (00:25:31):
Do you remember specifically your first use case and your first customer?

Rick Song (00:25:35):
I do! Yeah, actually very, very well as an e-commerce site. Actually it was a friend's, a friend of a friend's e-commerce site. And they needed to do, you know, age verification. The only thing we were willing to really focused on was, we will do anything around identity. It wasn't even like our later kind of breakthrough product. That one, I think they were paying us, $50 a year. Something like that, right? And we were so happy. I mean, we were so stoked that anyone was going to use anything that we built.

Pablo Srugo (00:26:07):
You love this show. You don't want to miss the next episode. Why would you? So hit that follow button. Trust me, it's in your own best interest. And that was literally just upload an ID, check that it. Check that you said age verification.

Rick Song (00:26:19):
Yeah, yeah. So exactly, upload an ID, make sure that you're, you know, above 21 to buy this online, right? And that was about it.

Pablo Srugo (00:26:26):
And the difference was before, the solutions then used human. Like in 2018, it was humans that would do that?

Rick Song (00:26:31):
Yeah, it was the humans. So you had to create an account, you then have to register the account, verify it. And that was a lot of our early work. So they'd have to keep track of all these various accounts on their system and make sure, they weren't doing that much deal. So a lot of it was actually done, I think, in some sort of like spreadsheet. And they were just email and ask people to email stuff over. So we've built some technology that'll make that a little easier.

Pablo Srugo (00:26:52):
So that works. Where do you go from there?

Rick Song (00:26:54):
Then you try to get the next one, and the next customer didn't have any similar requirements whatsoever. So a lot of our early work was almost like operating a software consultancy, frankly. 

Pablo Srugo (00:27:06):
Right.

Rick Song (00:27:07):
And a lot of our challenges was, you know, our theory at that time was. We will kind of almost build anything as long as it fell within the realm of identity. And, again, physical identity, there's a lot of forms of identity. So we did get a lot of folks who were always like, oh, could you build our authentication system? And we'd be like, no, that's not really what we do, right? We knew the long term goal, and I think it's really important to us at that time, not to deviate too much away from that. It was like, look, we have a vision of what needs to be done. If we start just getting distracted by anything, then, you know, we're just doing detours. There's no, even credible way in which we would say this gets back to our original vision. So that was the only really requirement. The second thing was really on the execution side. Anything that we build had to be somewhat generalizable. So, so much of our work would be, we get one customer afterwards, we'll keep refactoring until we felt as if there was a kernel there that wasn't like overly specific for just that one use case. And then we'd go back to the drawing board and go back into this like iteration cycle. And I think that was one thing that also is rather unique for us was this idea of explicit versioning. You know, we're not a waterfall development company. Where, in the agile way of continuous deployments every single day, constantly releasing. But we definitely had a perspective of still versioning matters and versioning matters. Because the iterative step doesn't necessarily mean that you'll go through intense generalizations. As engineers, a lot of times there's this question of, when do you refactor? And I actually think refactoring fundamentally is a product driven question. Not just a tech debt type question, right? I think this quote unquote tech debt thing sometimes is overly, how do I put it? It's a, I think like, overly abstract of a concept. Really you need to refactor when it feels if the proc requirements are starting to detangle more and more from your original intent of your architecture. So we refactored very frequently, almost after every single first of our first 10 customers. We would almost rewrite things from the ground up to make sure that it didn't feel overly specific for that one use case. So, you know, age is an interesting case. But we're like, you know, they can't just work for age, right? Otherwise, it's a very, very kind of limited product. We need to start rethinking kind of, does this overall abstraction of this setup make sense for the identity. Not just for, one use case and right off the second.

Pablo Srugo (00:29:17):
I'm no engineer, but just to just to clarify. What you're saying is. Because you kind of have, let's say that one customer, right? They come to you for age. I mean, your choice is either you build something hyper specific for them. Which is fast and relatively easy to build, or you build something super generalizable. Takes a long time, but then in theory, you could reuse it or whatever. Or you have this kind of hybrid approach. If I'm getting it right. Which is you build a specific thing and then you kind of figure it out after and you pull out the pieces that could be generalizable. And you kind of get the best of both worlds.

Rick Song (00:29:45):
Exactly, right? But it's like, right after we got that. It's really tempting to go for a second customer and be like, hey, let's just sell this and start making even more money. We were pretty aware that $50 is not enough to pay us.

Pablo Srugo (00:29:55):
It's not going to get there, yeah.

Rick Song (00:29:57):
It's not a salary, right? We're never going to be able to live off that. So it was kind of nice. It's a blessing in disguise, in which. There was no path in which after that we were like, yeah, this is going to build a business, right? But instead we felt as if we learned a lot about the considerations of the problem, and we could go back. And, we took, I think after our first customer. We kind of stopped talking to anyone for almost a month while we were rewriting things. And then after that, you know, we went. Did the exact same thing. Which was find anyone who would use us in any way, shape or form, and the second one was a startup. Which theirs was more of a kind of like, a trust and safety type use case. They want to make sure that folks on the platform were kind of trusted and verified. And who they say they are, right type of thing. So once we did that, that was a very, very different thing. But a lot of our generalizations.

Pablo Srugo (00:30:42):
 So, that's what? But is that not the same thing like, checking in a government ID or what did you have to do?

Rick Song (00:30:47):
So that one was a. At that point, I think we had to do a lot more, like, the government ID ones only. That's when we actually had to introduce some things around biometrics, right? Because a government ID, just because you have one. I could, take my friends, I could do anything. So we started building that. We had to start now linking these two solutions together, right? And that became a whole thing. And, it just gradually evolved from there.

Pablo Srugo (00:31:08):
This was like taking a selfie, this kind of biometric?

Rick Song (00:31:10):
Yeah, exactly. Yeah.

Pablo Srugo (00:31:11):
Okay.

Rick Song (00:31:12):
Like, taking a selfie of yourself and then be like, okay, is this the same photos? Same person.

Pablo Srugo (00:31:16):
Where was the broader tech there? Because, I mean, today we take this for granted. But we're in 2018, when you're starting this, were you. Was that already, that was all there? You just have to use it for this use case or did you have to actually build something new?

Rick Song (00:31:29):
So, there was some tech there already. I mean, biometric technologies, especially like facial recognition type stuff had been around even since the early 2010s. Especially from a, pure software deployment perspective. There was quite a bit that we had to improve on. At that time because the tech was, it was pretty rough, and especially like deploy to mobile devices. But again, Face ID had already existed, right? We couldn't use Face ID, but nonetheless just calling out that there was already a lot of groundwork. But improving it, and deploying it. And then a lot of improvements, that was a lot of work. We never really focused too much on, oh, how can we grow faster? And a lot more was, how do we keep on working with bigger and different use cases to prove out. Are we building the right thing? And we kept a lot of focus on that. Because even in the earliest days, we knew that this was kind of. If you're trying to build something venture scale, there's really two ways at it. One of which is, you bet on an idea and it turns out the idea is way bigger than you could have ever imagined. Or two, I think ours was a little more intentional in which if we wanted it to be large. We have to prove that it's large. And that meant continually finding different types of opportunities, different types of use cases in which it can emerge into. I mean, I know once we hired our first go-to-market slash. I guess at that time we called him a growth lead, but he was like. He effectively was a jack of all trades. Did everything from sales, marketing, post, it was just. He did it all, right? So truly was a growth person. I also, I think I was a bit psychotic then, but I had this whole belief at that time. I had taken this to dogma at this point. Which was, if, once we close one customer of a certain industry. No more customers of that use case or industry. We're not even going to talk to anymore unless it was inbound. 

Pablo Srugo (00:33:07):
Wow.

Rick Song (00:33:08):
Yeah, and we were going to keep on looking for alternative stuff. Cause, I think there was this belief. Again, a bit psychotic at the time. I was also under this belief that, we might as well find our fastest path to prove that this won't work as opposed to wasting our time and being delusional. The thing I have, I had a lot of friends who had done various startups and the thing I absolutely did not want to be stuck in. Is working on something for five years and then waking up one day and realizing, I'm not into it or this isn't going to work. That just felt terrible, and I think a lot of founders. I have seen this a lot in which I think a lot of founders have a tendency to self delude into believing like, oh, as long as I just keep on, doing a workout. But while they think that, they also aren't actively trying to prove that it's going to fail. They're not really trying to seek out truth. They're really just trying to almost delude themselves in this, you know, this nice belief and then continue.

Pablo Srugo (00:34:00):
I mean, I love it. Because what happens is, my perspective of it is most founders go into it with that same attitude. I don't want to waste a bunch of time. I'm going to be objective and I'm going to find something that's truly worth solving. And then at some point in that phase, they find something that may be the thing. And then it flips and all of a sudden it's like, okay, this may be the thing to get enough signals. This is the thing, and now it's like, let's make this work. And once you're in that, let's make this work mindset, you're no longer truth seeking and objective. And being like, oh, maybe this isn't the thing. You're like, this is the thing, and now I got blinders on on purpose. And I got to make this thing work. But if you make that leap too early, then that's when you wake up five years from now and you're doing like half a million, a million, $1.5 million ARR, but barely growing. And all of a sudden, you know, you're like, what am I doing? You know what I mean? This thing's got nowhere to go, but it's because you shifted away from that original mindset a little too early. It sounds like you were purposefully trying to stay in that open mindset for as long as humanly possible. Until it was just, you know, you've proven so many things out, you know.

Rick Song (00:35:06):
Yeah, I mean. A common question I actually get a lot is, have we found product market fit? Or when did you feel as if you found product market fit? And I'll be honest with you, I still don't feel it. I like that mentality of, oh, something will happen or, you know, we still have to figure out the next big thing, or continuing. I mean, I guess that's the trick of the venture game, right? Which is, at any point that you think you've made it and, you'll briefly feel as if you've overcome some hurdle. And then very quickly, either your board or just the news will show with you. All these other companies are doing infinitely better. And you're like, okay.

Pablo Srugo (00:35:43):
Yes, yes, yes.

Rick Song (00:35:44):
I always joke with people, it's like we're both so big and wildly, wildly small. It's like we're both fairly successful and unbelievably unaccomplished, and both can be true all at once. So in a very strange way, I guess I still don't feel it. That sense of, we still need to find out when this whole, you know, journey is, you know, this whole illusion will fade. I still feel that a little bit in which I'm like, oh, we got to keep pushing ourselves and finding that next thing.

Pablo Srugo (00:36:11):
But I mean, humility aside. There's a question of how big this could get for sure, and you always. There's always another level after this level. But you're obviously generating real value for a lot of real businesses at this point. Something that, you know, a year in or two years in. You don't really sometimes know, am I solving a top pain point for enough people? I think that, I mean, we can say we're past that today.

Rick Song (00:36:36):
There's definitely a bit of that, but I will say like. The only point I really felt as a truly major jump on the product market fit question is when I got one customer at 50. That actually felt meaningfully different. 

Pablo Srugo (00:36:48):
No way.

Rick Song (00:36:49):
After that, I wouldn't say it's changed dramatically. I mean, obviously it's like, oh, we're working with larger customers every now and then. I'm like, wow, that's incredible, you know, opportunity for us. I can't believe we're supporting this, but it feels, an expansion. A continued growth of the original thing. Which is we solve someone's problem and we're continuing to find ways to solve other people's. And hopefully with the same core kind of platform and making it a little bit easier, and smoother to continually solve more people's problems. But, you know, it, I think the root of it has continued to remain the same.

Pablo Srugo (00:37:20):
Walk me through, because now I get kind of the the product and go to market history. Maybe walk me through a couple of things. First of all, you start, just the two co-founders. You mentioned bringing that third, I don't know if it was a third person. How do you structure your team over those two years? How many people are you, as you navigate those first use cases?

Rick Song (00:37:40):
Oh, I wouldn't take my advice on this for anything, right? There was no intention or thought put behind this whatsoever. A lot of the early team were just folks that we thought were good, high potential and people we knew. And, again, that's why I say it's so much luck. It was either a referral from somebody or a personal friend. I mean, the first person who joined us, you know, still here, unbelievable. We'd so much of our strategic initiatives right now. He's someone I've known since middle or high school. I met him in high school, right? We'd actually like not spoken for a couple of years. But, we just randomly caught up and he's like, I want to do a startup. I'm like, oh, hey, you know

Pablo Srugo (00:38:15):
And when did you add him? How long into your journey?

Rick Song (00:38:19):
Three, four months. 

Pablo Srugo (00:38:20):
Okay.

Rick Song (00:38:21):
Three months, four months in, right? Yeah, and I mean, he was living in Seattle at that time and flew on down. You know, he was living on our couch for a brief bit. So I think for that first, like six, seven months. I mean, I think for the first seven months, everyone was working out of our apartment. The next person who joined us was an engineer and close friend who I'd worked with over at Square as well. And he was already considering leaving, wanted to do a startup, still here too, and he's incredible. And he kind of was just like, yeah, sure. Next person was the sister and the referral from someone I'd worked very, very closely with at Square, and then after that, you know, a co-founder. All of us just brought in folks that we knew. Who were high potential, high caliber and folks that honestly we just wanted to work with again. There wasn't really some intent behind it. I mean, for the longest of times, it really was just like, one, you know, the best part about a startup is there's an infinite amount of work to be done. There's no, you know, like, oh, you have to worry about stepping on anyone's toes. It's just, if you like, we just have a bunch of stuff to do. Just grab something off, anything and go off and do it. And as long as they were willing to, kind of do anything. And we're always thinking about like, oh, how does it play in my career otherwise? One thing that we were really intentional about telling everyone too was, if you're joining us. Just think of it as like a six month, one year kind of sabbatical. Almost certainly we'll die. There's not really a point to this, right? Hopefully we'll have some fun, we'll learn some random things.

Pablo Srugo (00:39:43):
So you instilled that mentality in everybody else. You didn't give them kind of that warmth and confidence of, you know, this is a billion dollar company.

Rick Song (00:39:50):
Oh, that this is gonna be the best thing ever? No, are you kidding me? No, not at all. I think that's wildly disingenuous. No, I mean, I think this went on again, even up until we were 100 people. I was like, look, if you're joining us, it's probably a waste of your time and a terrible choice in your career. But you may like it, right? And I think people used to call that the Rick anti-sell or something.

Pablo Srugo (00:40:06):
Yeah, right. Why did people join then? What do you think they saw that they liked? Especially the early ones, like the first 10 employees, just to make it up.

Rick Song (00:40:14):
I think part of it's the journey, but the other part is like. It's the same reason I think that I ended up doing this with Charles. Which is, above all else, I just want to work with Charles on something. Charles, I think, had the perspective of I want to go and do a company one day, right? Preferably with you, but he was definitely very interested in doing a startup and exploring that world, and I want to work with him. And for a lot of the team. I mean, even today, Persona is 70% referrals. We're like 400 folks, but 70% is someone that knew somebody else.

Pablo Srugo (00:40:42):
Wow.

Rick Song (00:40:43):
Right? And I think that core idea of wanting to work with people is. Above all else, the only thing that really differentiates companies from each other. If you're going to tell folks like, oh, this is like this, you know, there's always an opportunity to cause this type of thing. You're going to tell them this company is the most impactful thing in the world. There's just no way. I mean, right now, there's AI, but I even joke with people as big as AI will get. Maybe it'll solve global warming and cancer, and whatever. But, you could also work on those specific things, and I suppose that's a bigger impact, right? Half the companies out there are really just doing some software layer on top of something else. You can delude yourself into saying, this is the most impactful thing you can spend your entire life on. But again, I think if you just think for a little bit. That's probably not true, right? I think the only thing that really brings people together is wanting to, you know, the only thing in my mind that really differentiates any startup from another is the culture and frankly. The people that you want to be around and just work around. I think if you're going to do a startup. I think one of the worst mentalities have is what I often come to call like a min-max mentality. In which everything has to be the most optimal choice. Startups by default is a wildly un-optimal choice and a life career decision, right? You know, sure, you can go and listen to all sorts of random content out there. And I'm sure they'll tell you like, oh, here's the secret or whatever financial podcast or whatever, you know. The reality of it is like, no, it's really just kind of a journey and exploration. It's a personal decision at the end of the day.

Pablo Srugo (00:42:06):
I like everything you're saying, and I'm trying to put myself in the mind of a founder that is early stage, zero to one, whatever. And they need to hire an engineer, like they need to actually recruit someone for an engineering role. And, the go to thing is I can't pay as much. So I'll, you know, sell the dream, sell the impact, sell the options. Do you know what I mean? Hype something up to get people to quit their job at Square or their job wherever. You know, again, it sounds like you didn't do that. But I guess the question is, then maybe it's just you have to have that network. You have to have those referrals in the first place, or what's the alternative to make people ultimately want to join you when you need them? Also, that's the other thing is I need an engineer in the next three months. Well, I need them now. I got to go do something about it.

Rick Song (00:42:50):
Well, so, I mean. You hear every one of these stories. So first off, I'll say something that might be a little. I don't know, unpopular, a little uncomfortable, which is if you're just out trying to hire some random engineer or technical person that you have zero experience with or otherwise. I've seen some of the statistics around this, your probability of failure is, not just two X higher. It's like a hundred plus X higher. You almost, your probability of success right off the bat is effectively zero. If you are in that sort of situation. My advice, and I have some folks on this. And again, I'll say it. It may or may not be popular, but I think it's probably.

Pablo Srugo (00:43:25):
That's fine, be candid, yeah.

Rick Song (00:43:27):
Right? Is you're better off joining a company and meeting some people. And doing a really, really good job. The reason so many folks here at Persona are folks I've previously worked with. I mean, 50 plus people here I've known and worked directly with at some point in my career. I like to say, you know, I think folks who always have a plan of like, oh, trying to figure out how they'll eventually do a startup. They always are kind of, angling for something. I don't know, it's kind of hard to be a great coworker in that sort of stance, right? I think the most ideal one is you've worked with this person before. You know, they're great. They like working with you. You understand each other's working styles, and the best place to find that is doing a really good job at another place. And while you're there, you're also going to see, at least some operating norms, some things that will help you out, right? Joining another kind of company. I think people are like, oh, I'm just not a company person, I'm more of a startup person, I'm a founder type, like right out of the gate. I don't think that's like, you know. I think the, again, it's like, that's difficult. The only other type in which I see like success out of this is usually it's classmates or something like that, right? And which, again, they've worked together at school or something where they're friends. But it almost always you're probably a success at least working. Maybe not with a friend, but someone you've worked with before or no is so much better. So, my general perspective is, if you're out trying to just hire a technical co-founder or otherwise. Consider working for a couple of years. Honestly, you might, it probably would actually save a lot of time. Because that way you can find someone that you really like working with. Bring them along on the journey with you, right? And, you've already de-risked so much as opposed to spend one to two year. Kind of cycling around, try to figure things out, right? And at the same time having to learn, completely independently.

Pablo Srugo (00:45:04):
I think it's totally legit. And I think like a lot of the founding, you know, the entrepreneurship thing is really romanticized. And you over focus on like, you look at Steve Jobs or Bill Gates, or whatever. Some of these founders that, you know, Mark. Started, freshman sort of thing, like right out of college, had no network and look at what they build. But they're not that one percent. They are true, like, six events and, you know, also they had a company. That this is the other thing is if you have a company that's absolutely blowing up. Everybody's going to want to join you, including people that you don't know. Most companies, even the ones that do really well, aren't blowing up at that level. And so if you don't have a network, going out to like, you know, be in the real world for a few years is probably not a bad idea and a great idea to increase your odds. If you ultimately do get a good idea that you want to run with and start on your own.

Rick Song (00:45:50):
I also say this, for everyone you just said. I mean, let's go with the founding stories, right? Microsoft, Bill Gates and Paul Allen, right? High school friends, very, very close friends for a very long time. Had done actually work together in high, you know, they're both prodigies. But like, probably a little bit older than Bill. Knew each other very well through all of high school. They'd worked on all sorts of projects, right? You know, what was it? I forgot the exact founding story, but right?

Pablo Srugo (00:46:15):
They did. But I mean, in terms of the first 30 hires that they made. They probably didn't know most of them. Would be my guess, actually, I don't know that for a fact.

Rick Song (00:46:21):
Using a, at least I can say for the Apple one, right? Like, Woz and Steve Jobs.

Pablo Srugo (00:46:25):
Yeah Woz, that's true.

Rick Song (00:46:27):
Worked on Atari together, right? And not to mention, they originally met through the computer club and a bunch of the early hires computer club people. I actually knew one of the first like 10 hires. Because he was at Square, incredible guy. And, I think,  he got introduced to the company through. I think, his parents, who knew like, Jobs' parents.

Pablo Srugo (00:46:44):
Right, yeah even that's reforming. That's interesting, actually. Yeah, that's a good point.

Rick Song (00:46:48):
Right? Google, two people were PhD students together. You know, you go through Facebook. Technically, for Harvard students, I know Social Network portrays that. But again, the first early journey was all that, and a lot of the early hires were all Harvard slash Stanford kind of students that they knew. It's very, very hard. Everyone always says, like, you need to cultivate your network. But if you look through all the networks that are formed. It's very rarely through networking events or otherwise. It's through some alternative, deeper relationship that they build. That forges something that's beyond just a pure business transaction. So whether that be school, whether that be working together. I mean, I oftentimes tell folks if there was one thing I credit to the best thing that made Personas. Increase the Persona success, it was how long I was at Square. And I'd like to say, you know, I was dedicated and did a fairly decent job. But I think above all else, that actually increased the probability of our success more than anything else. By like orders of magnitude.

Pablo Srugo (00:47:41):
Another thing I want to touch on. Because we didn't touch on it yet, is the fundraising history. So you started off, you didn't know anything about fundraising. You said you just started building. When did you look at fundraising as something that you needed to do and kind of start exploring that side of it? Or how did that happen?

Rick Song (00:47:54):
I mean, it was, again. Actually, I got pulled into it because friends that I know. My old boss, Jackie Reese's, right? She was the one who, you know, put in a huge, unbelievably kind word. The person actually who pulled me out to the valley, who hired me for my first internship as part of the Kleiner Perkins Fellows program way back in the day. He reached out and was like, hey, do you want to think about fundraising, all of that. A bunch of people actually just reached out and many of them I'd either interacted with at some point in my career or while at Square. They were like, oh, let me help like support you in any which way. My old manager, when I left Square, I was far too shy to speak with Jack. I suppose I still am, you know, Jack Dorsey is still, this Idol. I don't know, like sagacity figure out there.

Pablo Srugo (00:48:41):
Yes, mythical, mythical figure.

Rick Song (00:48:43):
Yeah, mythical figure, right? And, he's another guy who can will things into existence. I mean, incredible businesses, right? The guy truly has a very, very incredible vision. Ability to have a vision. But I was far too shy to find time with him. But my old manager set up, and when I left. He was like, hey, he was a very, very early Square employee. And he was like, I set up an hour for you to just pepper jack with questions and talk. And just all sorts of things like that, right? And I think that was all because.

Pablo Srugo (00:49:11):
What was that like?

Rick Song (00:49:13):
I mean, honestly, in retrospect. Embarrassing and cringey, right? I was so nervous for it. So, I think I wrote down 100 questions, and all the questions just the worst, right? And I felt like some sort of awful beatnik journalist just asking him all these things. Now that I think back on some of those questions I asked. I don't even know how to respond to them, right? So the questions are too general and not at all. To the question of when to start thinking about fundraising as an example, I asked them the same thing. But the quick answer, all I can give you is it depends on the business you're running and who you are. Which is what he told me, and at that time I was like, oh, what an unsatisfying answer.

Pablo Srugo (00:49:53):
Yeah. It depends, yeah.

Rick Song (00:49:56):
And then I thought back, I was like, fuck, I don't know. That really was the only way he could say it, right? That question's not by any means bad, but I had worse ones too, right? It was just all sorts of random stuff. I asked him about prod, how to think about prod. Oh my gosh, and all the answers are really, it just depends, right? But he was so gracious with his time, and then at the very end. He asked a little bit about what we were doing and imparted some piece of wisdom. And it was nice, it was really nice. I'm very, very grateful to Jack for the time. I'm ever more grateful to my old manager, Ted Mao, who I still think is an incredible person.

Pablo Srugo (00:50:34):
So, what was your first round? And when was it? And how long after you left?

Rick Song (00:50:40):
I think four or five months. I can't exactly remember.

Pablo Srugo (00:50:42):
Sure, more or less.

Rick Song (00:50:44):
It almost pretty much completely manifested from various folks, kind of talking about us and making introductions on my behalf to various people. Gosh, I get always emotional thinking about it. Because so many of those introductions I didn't even ask for. They were just like, you need help. Let me help you out, right? You should talk to this person. Our first round was with First Round Capital. Who continues to be absolutely incredible. Kleiner and Coatue also participated. All of the folks there were either introduced to me by someone in my life or because, there was some involvement, right? Part of the Kleiner Fellows program. All that, everything kind of culminated.

Pablo Srugo (00:51:24):
How big was it around?

Rick Song (00:51:26):
It was about $2 point something million. Like, $2.4 something million. I mean, at that time it was decent.

Pablo Srugo (00:51:34):
Yeah, yeah. For sure, absolutely.

Rick Song (00:51:36):
I mean, again, we couldn't believe it, right? We were like, gosh, I don't even know if we'll make revenue greater than this, right? That's an incredible number.

Pablo Srugo (00:51:43):
Well, that's what I wanted to talk about. It's like, okay, so it comes inbound. You don't have to do that much work to get it. Great you have the money, but does that change your mindset at all? Does it add the pressure that you're kind of so much trying to not really have upon you. Because all of a sudden you know they do need to get a return. It isn't really I mean a lot of their stuff will fail and they know that. But they're not in it for you to come back in six months be like, hey, it didn't work. You know, sorry that's not ideal.

Rick Song (00:52:11):
So we definitely added a ton of pressure initially when we fundraised, and actually I think my co-founder. Our first hire, like there was one really late evening. I remember they both effectively had an intervention with me. It was like, you got to chill, you know? And I think, and it helped a lot. Because it helped restore this level of sanity of, you know, what are we really trying to do this? And, it's a journey. At the end of the day, the only thing they can ask for on us is we tried our best. And, I think we had a lot of fear that we would be disappointing a bunch of people. I think we had a rule that we did not take any funds from any friends or family. Because we just didn't want that additional pressure of any way, shape or form. I didn't want to, look at someone who I knew in my personal life and be like, oh, I lost your money.

Pablo Srugo (00:52:50):
That's smart.

Rick Song (00:52:51):
So we didn't do any of that. Which helped a bit, and then beyond that. I was like, hey, they believe in us. The only thing we can really do is try our absolute best.

Pablo Srugo (00:52:59):
But they were aligned high level with your approach versus trying to get to a million or $10 million. Or whatever as fast as possible in that stage? They were aligned with that kind of idea?

Rick Song (00:53:08):
I mean, and actually a lot of folks had shared this too. Which is actually one of the best. I can't remember who gave me this advice, but it was one of the best that I've ever received. Which was, the faster that your product can get to a million. The faster your product is likely easily replicated.

Pablo Srugo (00:53:21):
Sure. Yeah.

Rick Song (00:53:22):
Right? And I think that also took a ton of pressure off. If you think about some of the, I mean, speaking of, you know, incredible companies. Actually, Charles was lab mates, and actually, I was interns with Dylan Field over at Figma. He's one of our, he is one of our angels. I mean, you know, kind of both a friend, but also, incredible founder. So kind of sat in a different category. He gave us a ton of advice in early days. Was super, super helpful. I remember he hosts us at his office. When it was just the two of us and we kind of just sat around and chatted. And we're like, holy crud, Dylan. 

Pablo Srugo (00:53:55):
That's sick.

Rick Song (00:53:57):
This is insane. And he, you know, I think he, was like, oh yeah. But, I mean, if there's a company I admire tremendously. Figma is an incredible business. I love his story so much, because he founded it. Figma, right after the time in which the two of us interned together. And that's the story of them to what? A million in like seven years. They spent so long on investing on the technology. Making sure the product was great. I think, and today we all see this like meteoric rise or whatever. But I mean, the investment they made is insane to actually continually hone and crystallize a product. Another one that I actually met through first round, who again, I feel tremendous gratitude towards. But Clay, I think is another company which I think like, so highly of. Kareem, I think is an incredible guy. Clay's another one of these businesses in which they took a long time to find the exact product fit.

Pablo Srugo (00:54:43):
Huh, I didn't actually know that. Interesting.

Rick Song (00:54:45):
Yeah. I mean, they were founded. I think, Kareem first started exploring startups. Oh, gosh, if I'm wrong, Kareem, I'm sorry. I think it was 2015, right? And I remember when we first started, I met with him and, we've been in touch even. I think, borderline, like actually after. Since the first year of Persona founding, I've known the guy. You know, just talking with him and hearing about a lot of their early journey. I think was humbling, and it was really cool. I think like similar, they had a early round from Sequoia. But then they spent a long time continually trying to crystallize and figure out exactly what they're trying to build. And they didn't really aim for ARR or growth until they knew they were happy with the product, that they really put together. So those are a couple of stories in which, I think sometimes people chase way too much towards, how fast can I get to something? And one of the best things Kareem ever told me is really take, like, not taking the journey for granted. You did it not for the result. You did it to enjoy the journey. If you're, putting the pressure on yourself with a sole focus on an outcome. It, again, it's almost self-defeating of a mentality.

Pablo Srugo (00:55:54):
And so how long did it take you guys to get to a million ARR?

Rick Song (00:55:56):
I don't even remember. Yeah, I think like maybe a year and a half or something. Yeah, we were relatively fast at it. But there were, you know, we got lucky on a couple of things, right? Crypto, fintech both took off. We've had setbacks, with the decline of that, and then we had to rethink. But the strategy never really changed. The product really never changed, but we got luck. I think some companies get lucky, but it's never like a smooth road for anybody.

Pablo Srugo (00:56:20):
Perfect. Well, listen, let's stop there, and I'll ask the last two questions that we always end on. There's three, but the PMF one you already answered. The other two are, was there ever. I guess this is for you, it's already kind of answered. Frankly, but the question is, was there ever a time that you thought you would fail? Which you basically said was, all the time or at the beginning?

Rick Song (00:56:39):
I mean, I still feel it. Yeah, still feel it very, very all the time. So, yeah.

Pablo Srugo (00:56:47):
And then the last question is, and you mentioned you speak with a lot of founders. What is like? What's some of the most common early stage advice you find yourself giving?

Rick Song (00:56:55):
It's this idea, like hyper-optimization. I think, is the greatest failure for.

Pablo Srugo (00:57:00):
What do you mean by that?

Rick Song (00:57:01):
As in, something I really believe in, and I tell a lot of folks here at Persona is. You know, I think that people can be crippled. Every single company from a value perspective always has something similar. Which is moving fast, you know, like disagree and commit. Something about, how do you just make decisions at a higher pace? I think there's this underlying idea behind it. Which is that it's actually unlikely thinking a long time about a decision will actually dramatically improve outcomes. Especially for very difficult, uncertain decisions. Actually making a decision and then quickly reverting or just learning from it is way more important than the quality of the decision. So pace it, I think an implicit thing is actually pace of decision-making matters more than quality of decision-making. One thing I really believe in, this is actually both from reflections at Square and Persona. Was that what was terrifying for me wasn't even that, we couldn't sometimes tell which decision was right or wrong. We couldn't even tell which decisions mattered. There were situations in which I think some of the most impactful decisions for Persona, were things that we kind of just offhand did and didn't even think twice about it. We didn't think it was an important idea, and later on it was like, holy crap, this is actually really pivotal. And there's other things in which, we thought, oh, this is going to be a huge deal, in which it turns out no one cares. And I often say, it's like terrifying to come. It's humbling, terrifying to realize that not only can you sometimes not predict if you're right or wrong. You can't even tell the magnitude of a decision. So what this implies is a lot more times actually it matters more. Can you just make decisions quickly and try your best? And, you know, obviously you can't be wrong all the time. But if a decision is not immediately obvious. It's better to just disagree and commit or move fast and break things. Wherever, you know, common kind of value. Company value you want to follow, and I think a lot of times one of the scariest things. When you're small, you'll get paralyzed by all these things because again, it's like, oh shoot, you know, I'm scared this will destroy us. And the reality is almost none of them will. But what will kill you is not moving fast enough. So, that's why I kind of say it's like, this mentality of hyper optimization. Where you're like, oh, how could this be a little better? Trying to hyper optimize every single situation is not only a waste of time. I think it's actually really damaging. And a lot of the decisions that really matter, you may not have optimized it perfectly, but like they're huge, right? And your goal is to find as many of these impactful decisions as possible just through almost a quantity search. Not from a, oh, let me get every single decision absolutely perfect. You're going to get just washed away. Because you're going to miss all the major big decisions.

Pablo Srugo (00:59:32):
Perfect. Well, Rick, thanks so much for jumping on the show, man. It's been great to have you.

Rick Song (00:59:36):
Likewise. Hey, thanks so much again.

Pablo Srugo (00:59:38):
85% of people who listen to the show, just started listening to it this year. You're probably one of those people. In fact, the odds are 85%. Guess what? You need to go back because there are over 100 other episodes that you need to check out that are just as good, if not better, than this one. Don't miss out.