Episode 22

Ask why it won’t work — Rick Song’s lessons from Square and building from 0 to 1

Today’s episode is with Rick Song, CEO of Persona. Before starting the identity verification company, Rick was an engineer at Square and an early team member at Square Capital. On the heels of raising a Series B round, Rick shares his approach to building from 0 to 1, from why he favors pre-mortems and unusual recruiting moves, to Persona’s go-to-market strategy.

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Rick Song: [00:00:00] I think the one thing that you've consistently found true for building a business. Is that almost anything can work. It's actually a lot more about how all the pieces are put together than trying to find the best piece for everything. I made this analogy to some folks, which is like building a team is not about finding the greatest talent for every single role.

It's actually a lot more about how does every single person work with each other. You're building an NBA team. It's not about finding five. All-stars. It's really about finding five synergistic players who can really play off each other. And I think the same. Really applies to building a business as well, which is it's nationally.

I figured out, oh, what is the perfect thing? Like what did this best company do? It's a lot more about thinking about much more holistically and how all these parts interact.

Brett Berson: [00:00:48] Welcome to in depth, a new show that surfaces tactical advice, founders and startup leaders need to grow their teams. Their companies and themselves. I'm Brett Berson, a partner at first round, and we're a venture capital firm that helps startups, like notion, roadblocks, Uber, and squared tackle company building firsts through over 400 hundred interviews on the review.

We've shared standout company, building advice. The kind that comes from those willing to skip the talking points and go deeper into not just what to do, but how to do it with our new podcast in depth, you can listen into these deeper conversations every single week. Learn more and subscribe today@firstround.com

for today's episode of in-depth. I'm really excited to be joined by Rick song. Rick is the co-founder and CEO of persona. A platform that enables companies to create the ideal identity verification experience for their customers before founding persona in 2018, Rick was an engineer at square for five years and an early team member at square capital.

It was here where Rick had the insight that led to starting a company from fraud prevention and lending. To trust and safety with food delivery for caviar, he saw that there's a wide range of use cases in identity verification. So a one size fits all solution just won't work with low and no code building blocks.

Persona enables customers to craft a more tailored experience. On a personal level. I first got to know Rick after first round invested in personas seed round, and I've come to believe he's one of the most thoughtful founders around what I think is particularly special about this episode is that it comes at an exciting inflection point in Rick's journey of building persona from zero to one.

Just last week persona share that they've raised $50 million. The company is around 50 employees and they're looking to double the team this year to keep up with revenue that surged more than 10 X and a customer base. That's grown to include some big logos, including square Postmates and Gusto in my conversation with Rick today.

There's one theme that stands out. He's somewhat obsessed with the idea of pre-mortems or figuring out why things might not work out from all the ways a candidate might fail to why a customer won't want a product to how a commonly used framework might not be a good fit. Rick brings this mindset to every aspect of running persona, starting with recruiting.

Rick shares his lessons learned from his time at square. I found there was a lot of counterintuitive thinking in his answers here, including why he likes hiring folks who haven't worked at a startup before and why he doesn't try to convince candidates that persona is a company that will change the world.

Next we chatted about why Rick believes it's not about going down to first principles, but rather studying other companies to find unusual moves and experiment with different strategies. He shares what he's learned from studying companies like Google, Microsoft, Atlassian, and Shopify, any dives into why popular frameworks like OKR or jobs to be done might not work for your business.

From the strategy behind personas multiproduct approach, including a candid discussion about the risks, to why his engineer's sell and cold email prospects, rich share some really detailed go to market thinking here. I think there's tons of insights in this conversation for anyone who's a founder or thinking about starting a company one day, but there's also plenty in the year for engineering leaders and hiring managers as well.

I hope you enjoy this episode. And now my conversation with Rick, Rick, thanks so much for doing this with us. We so appreciate 

Rick Song: [00:04:57] it. Thank you so much, Brett. Really appreciate the 

Brett Berson: [00:04:59] time as well. So the place I thought we could start is on interviewing it's something you would be at talked about from time to time over the last couple of years.

And maybe we could start all the way at the top with the way that you think about interview process. What's good and bad. Things that you've relied on both during your time at square. And now of course, building from zero to one at persona, 

Rick Song: [00:05:21] I think interviewing and hiring really evolves from the earlier stages all the way to the later stages.

So for earlier phase companies, I think there's a really big piece of the first 10 people that I hired. Make a huge difference for your company. This is pretty common advice, but the first 10 folks of the company, oftentimes we'll set the entire foundation for the culture. As much as the CEO or founder would like to dictate what a culture looks like.

It really will be the motivation of these first 10 people who really will dictate the things that this company values and to really find that I think first and foremost, referrals makes an enormous difference. Keeping the early conversations, casual, having it, where you're not trying to suss out can this person do their job.

Making sure the relationship there is more so a horizontal like camaraderie type based relationship where you look at the individuals equal because for these first 10 folks, it really will be like that. And in order to really suss out, there's a couple of things that we value a lot here at persona.

Number one is. Conversations with everyone here. And oftentimes how we think about it is this individual has to work well with all the first 10 people. As companies generally tend to scale, you can have more and more pockets of groups, you know, individuals who kind of collaborate here or there, and you can really structure the company in a way that hopefully for any sort of problematic relationships, it's a little bit more hidden away.

But for the earliest set, there is no escaping though. So you really have to think critically about whether this individual will actually interact well with everyone else here. The second piece is references makes. An enormous difference. You'd imagine that every single individual they'd never give references who wouldn't speak positively of them, but how the person speaks positively about them makes a huge difference.

The last piece I always talk about is the best advice actually received from someone at square before, which was oftentimes when you're about to extend someone, an offer, you're thinking to yourself that, oh, this person can solve this problem. They could solve that problem. There's so many problems that they can help solve.

This person will be absolutely amazing. And this almost certainly will be true. But it's actually far more helpful to think about all the ways in which this person may not work out for your organization focused on the team, that they may not interface well with the types of projects they may not succeed in.

And a lot of ways, the first, like three months of any new hire it'll look like kind of a honeymoon type of period as a result, it will really mask a lot of otherwise clear problems they may have, especially if they're here longer. And one big piece of this is really thinking deeply. About all of these kinds of like potential pitfalls can really help set you up for success downstream and make sure that this individual is successful.

And also if it doesn't work out that you can take action far, sooner than you'd otherwise imagine. And this is a mistake that we've made countless times now. So it's really been drilled into us and something we've thought a lot about. 

Brett Berson: [00:07:54] So on the pre-mortem idea where you sit down and think about all the ways this candidate might fail, when they join you, how do you actually do that?

And how is that operationalized so that you can then take action 

Rick Song: [00:08:07] on it? The first part of it really is I oftentimes think a lot about how this individual. Interact with the top five people expect them to interact with on a daily basis. And in particular, what are core areas that I believe that their working style has made it for?

If one person is particularly process heavy, whereas the other person's much more loose and adaptive to the current situation. If the communication styles are fundamentally different, if what they value differs greatly. And for those top five people to interact with, I think it's absolutely critical.

That, that interaction will be positive. And it's complimentary, you just sort of do a 

Brett Berson: [00:08:41] mental exercise or you open a doc and write it out in some structured way. 

Rick Song: [00:08:45] So in the, the days I used to always write a doc about it, I put something down for myself, whereas as we've gotten larger, I stopped writing it down.

But in the earliest days, I used to try to write something down for myself as to who would this person work with and how would they do. These days, I think a lot more of is we really coach hiring managers here to just think deeply about this and more importantly, to make a really strong pitch themselves, why this person may not work out and just be heavily, heavily aware of it.

So how we oftentimes talk with hiring managers here is externally to the rest of the team. You should be the absolute champion for this individual. If you are thinking about hiring someone, it's critical that the rest of the team knows that you have their back. So that means whether in the hiring part, otherwise you.

Are incredibly supportive of them and frankly, you know, always biasing towards why they'd be successful while internally and possibly, you know, with you're thinking about what may not go so well. So what would 

Brett Berson: [00:09:36] be an example of a pre-mortem one, two, three things that you would think about and then how do you actually.

Act on it. So you don't wind up saying, yeah, I could see the bus hitting the wall. And then 90 days later, the bus hits the 

Rick Song: [00:09:49] wall. The number one thing earlier mentioned is what kind of people, this person to interacting with the number two is what kind of projects do we think this person will be least successful in?

So whether that be particularly complex projects, projects, where there's a lot of nuances, is this person more of a big idea type of thinker? Are they someone more social versus a leading type of role versus do they really. Prefer to be kind of in a supporting type of role and thinking through the type of projects they'd be successful in.

And the third aspect of it would really be who are they as an individual and what will really make them feel excited about being here every single day and making sure that we can really help provide that and making sure that whatever role that they're in, who they work with to project that hours to anything else that this is a place that'd be successful for them.

So thinking through those three key pieces, how do we operationalize that? I'd say number one, If you don't feel strongly about this as a hiring manager, you have the decision. And oftentimes, although saying no may feel harder, it's far better to be a little bit more pessimistic on this side, just because hiring such a big deal when you're only 10 people, 20 people, 30 people.

It's a 10% incremental difference in terms of size of your team at 10 people. That's enormous. So being a little bit more pessimistic on this can really save a lot of heartache in the early days. I think it oftentimes feel so hard to hire folks. We actually had a tendency to rush their own decisions and like hire someone a little bit sooner than we actually needed them.

There was so much difficulty in trying to convince anyone to join us, but I think the aspect of being a little bit more cautious and honestly, again, biasing towards no. Has just paid off so much for us when you were 

Brett Berson: [00:11:20] talking about the pre-mortem a lot of what you were getting at is things tied to a really deep understanding of the candidate.

And so I think it would be great to learn about how do you learn that it's very different if obviously you're recruiting somebody who you worked with before and you know, them intimately. But if you don't know them as well, how do you structure a process? So you can learn enough to have that fidelity that they're strong in this way.

They're weak in this way. These are the types of projects that they will or will not be successful in those types of things. 

Rick Song: [00:11:47] Depends a bit on the role, but especially for a lot of the non-technical roles, it can be really difficult to. Overly emphasized on how a person will actually be able to do in the job.

There's just, aren't exercises out there that can really put up for the individual, unless, you know, it's a particularly kind of operational type of role that you can have a great assessment as to whether this person will do well or not. So. Instead for most of my interviews, I actually speak very, very little about how will you solve this problem?

What was the hardest challenge you've ever faced or anything like that? I think oftentimes a lot of people out there have canned answers for this, or I've thought about it. So for myself, I actually spend a lot more time on focusing on the incentives of the individual. What do they care about? What motivates them?

What drives them? If it's an hour interview spending 40 minutes, actually diving very, very deep into. What does this person want to do? What is their ideal day to day? Like what do they care about? And people that they work with, what do they care about and the product that they work with and trying to nail the motivations and incentives for this person, because I'm a big believer that if you can get to the root of what someone's motivations are, you can kind of like problem solve and theorize exactly how someone would tackle a lot of problems out there.

And I think that key piece there is really kind of how we build up this mental model. Of how this person behave in certain situations. For example, if someone's incredibly motivated by supporting others, by making all their success by elevating others, you can usually have a really good sense of how will they behave when there's a product launch, how will they behave when a customer challenge arises, how would they behave?

If there's. A misunderstanding or a disagreement between two Indians. Are there 

Brett Berson: [00:13:22] specific questions you find most illuminating? You sort of rattled off a bunch of different areas. Are there any specific ways that you phrase things or questions that you find the most signaling? 

Rick Song: [00:13:33] I always ask a couple of them.

One of them being, what do you want to do after your next role? And oftentimes framing it around the idea of most likely you won't be here for the rest of your life, if you are, that'd be absolutely incredible. But. At the end of the day, hopefully this helps you get a little bit closer to whatever that future you envision or, you know, wherever you want to wind up is.

So we put a lot of emphasis on trying to understand how can we make sure that we're setting you up for that right. Future, you know, and in addition to that, I always ask, like, what do you believe in, why do you believe in it? What is the probability that this is right, and really drilling deep into what kind of role view have they established over their career?

And then lastly, a lot about what are the most important things that you're looking for in your next role. And I think oftentimes it's very, very common for individuals to focus a lot more on the size of the market and impact on the world. But for us, I very, very heavily biased towards people and like first startup, especially of our size, I usually really try to set the frame that as much as we'd like to change the world, it's an immensely challenging task.

And. Startups, especially in the early days, honestly, it's a huge grind. So if I don't hear that, the number one thing that motivates them as people, I usually think that this probably isn't the best fit for the individual, frankly, people 

Brett Berson: [00:14:53] in the sense of the 

Rick Song: [00:14:54] people they work with. Yes, absolutely. Or the people they support or whoever that may be, but people in a very, very general sense and oftentimes I'll drill a lot deeper.

And to who, why people, when, when you say people, like, what does that mean? Does that mean day-to-day, it's someone that you can joke with or after work or go and hang out with? Or is it people from the perspective of this person's motivations are amazing? Is it people that you admire versus people that you respect, people that you can learn from?

What aspect of people and why does it matter so much to you as an individual? How 

Brett Berson: [00:15:21] do you think about hiring for potential versus experience? I 

Rick Song: [00:15:25] think it's incredibly role dependent. Then on the engineering side, I think the best analogy here is if you're trying to hire someone to set up a foundation, regardless of the amount of the potential, the individual has the foundation, you can't really bet on that because everyone else will really be building off the exact same foundation that this person has set up.

So no matter how much potential this person has, if they set up the foundation poorly, the long-term cost of it will just very, very quickly outweighed the short-term benefits that the individual can grow into. So. I think this really applies to kind of any type of roll out there is this person setting up a foundation that impacts others where the exponential effect of the missteps this individual might take, regardless of the potential outweighs the growth potential of that individual versus is this a much more isolated type of role where they can learn without impacting too many other people and then downstream and longterm from all of the learnings that they have there's benefits 

Brett Berson: [00:16:13] there.

So how does that map to, when you think about the first 10 folks you hired a persona, does that mean most of them tended to be more experienced? Or even in those first 10, some of the folks building more foundational things, sort of one way versus two way door type work, it 

Rick Song: [00:16:27] depended on the, for example, the first business hire and currently the individual who leads pretty much all business efforts here.

Christie, we brought in someone who had a lot of experience leading people. Who'd been at a variety of startups and kind of knew what she was doing because she'd be setting kind of the business direction. Of the entire team from sales, marketing, customer success, and much, much more. Whereas on the engineering side, both Charles and myself came from engineering backgrounds.

So we could really tackle a lot of the foundational pieces. And we could actually bring in some folks who may not have been nearly as experienced on that side, on the product side. Oftentimes the mistakes that you make are much less costly. There's a lot of two way door opportunities there. So. We could hire a little bit more junior on the sentence that on the potential individual grow with us, because at the same time, we're still trying to understand what our product is.

So any mistakes that we make at this time, It's really hard to say whether it would have been correct or not. Design was another one where oftentimes, especially in the early days, like the foundation that's built there, it's a lot easier to mold and redesign. So we were able to hire a little bit more junior on this end.

It really depends on the type of product that you're building though. We were a B2B SAS type of business. So. Design, wasn't an absolute pillar around how do we actually go to market over time? I think this is evolved and change. So as a result, we've also started hiring more and more senior folks. 

Brett Berson: [00:17:43] We talked a little bit about pre-mortems.

We talked about some of the ways that you spend time trying to get to somebody's core motivations. We talked a little bit about hiring for potential versus experience. Are there other pillars or building blocks to the way that you've approached? Interviewing folks that you find particularly useful. I'd say 

Rick Song: [00:18:02] one thing, big area for us in terms of thinking about hiring is almost an exercise of segmentation.

I don't think this is something that you can deliberately figure out as you go into the market, but just being cognizant that there is a segmentation that's happening within the market. An example of this is today. Oftentimes if you're every single startup out there, speak about hiring for mission, we're going to become the largest company in the world that you know, you're riding on a rocket ship.

As a result that segment is incredibly crowded and everyone kind of speaks the same message there. So for us, we've actually taken it almost in completely inverse approach towards how we communicate ourselves. And I think it's also been really helpful in terms of how we build out the culture. So things I oftentimes say to candidates is we're not trying to change the world.

We're just hoping to make it slightly better. And hopefully if we succeed. People never think about their personal information being lost or mishandled ever again. It's almost like essentially like just moving a burden for a lot of people out there. We oftentimes speak about how, whether it's a rocket ship or not.

I can't promise that to you. I think it'd be amazing if we could grow in that way. But at the end of the day, we're just trying to take a step by step and frankly, make sure that this is a great place day to day for everyone here. And a lot of this messaging hopefully runs a bit counter to, I think like traditional startup messaging, which has been really helpful for us because for a lot of the folks who end up joining us, we become their top pick.

They oftentimes tell us that this is the only company I was considering, especially after everything that you've told me. And this has helped us a lot from just purely the segmentation piece and also reinforcing aspects of our culture from a culture of humility, a culture of really wanting to work with other folks.

And caring a lot more about the day to day. Not so much about how large this can all be, but really just about doing a good job on every single project. So to kind of like tie all this back together, I would say. Thinking a lot about this segmentation piece and finding out what is uniquely attractive about your company.

And that doesn't have to be, you know, what's traditionally attractive, but rather there will always be a segment of the market that is under-tapped. And once you start isolating more and more on this, and once you start realizing that, yes, this is something that I think. People resonate with, and they don't hear from everyone else.

It can really help you attract a lot of talent that you don't have to compete nearly as hard for. And frankly, hopefully resonates more. So with what makes you uniquely you? I always tell folks, especially that we interview, I don't know where persona will be in 10 years. If we are huge, that'd be absolutely amazing.

Oh, we're still alive, frankly, but that also still be amazing. But all I really try to index for is that 10 years down the line, if we were to suddenly go out and say, Hey, there's going to be a reunion. We all really look forward to seeing each other. Again, it's not because we're all friends, but because we really miss working with each other, we all really respect the working ethic, the quality, just the overall experience of working with each other.

And if that were true, I think I've done a great job in terms of huge success. For myself. When 

Brett Berson: [00:20:47] you think about this topic of hiring and interviewing, what are the things that you learn from square that you're applying? And I'm sure some of it is some of the things we talked about and maybe what are some of the things that you changed or didn't work or approaches that were 

Rick Song: [00:21:00] non-transferrable big mistake around this in the earliest days where we try to create an entire track for interviewing.

So when it was Charles myself, And maybe two other people, we try to prematurely create like an entire interview loop with like phone screens and interview problems and on-site interviews and make it seem a lot more mature than it actually was when you're large, like square. Oftentimes when people apply, there's a very high probability that they'll join you.

You're an established company. They intentionally came in. There's an entire foundation that the company has built that is supporting. Recruiting efforts. And when you're small, it's actually much different. Like it isn't just about assessing whether this person's qualified anymore, but actually every single interview is also a cell.

And that was a really, really key thing that we realized after a couple of conversations where we can't like assess how good this person is, whether there'll be a fit or not. And then after trying to sell the candidate, we actually started doing that simultaneously. And it was a strange thing to tread, but we found that balance where it meant turning the interview a lot less from like, Hey, let me ask you a whole series of questions and afterwards, speak with the team about whether this person would be a fit or not, but rather it became much more of how about this become a conversation, teach us what you do.

Especially given that we were early. We didn't know half these functions the same time. We'd also be able to understand better about how you think about things. And really making that a much more back and forth process. And I think especially maybe less than 20 folks, most interviews will be like this.

You know, if you're trying to attract top talent, it just can't be like, oh, first let me make sure that you're good enough. I think it creates again that weird power dynamic that makes it incredibly hard to hire. You really have to start with a much more kind of like back and forth type of approach where, you know, even show that vulnerability of these are things that I'm not particularly good at.

These are things that, you know, we really, really need help with. And you. Can make an enormous difference here and showing how flat the entire organization is before just trying to assess like, oh, how, what about anything 

Brett Berson: [00:22:58] that jumps to mind that square did exceptionally well? That is something that you've adopted or as part of the way in which you approach hiring 

Rick Song: [00:23:06] and interviewing.

I think pieces that were really, really well done there. So there was actually an entire training process for anyone to become an interviewer. And especially on the engineering side, this was very, very rigorous. You'd start off being on the interview panels, whether that be a technical interview or more so Q and a cultural type of interview, you'd really start there.

And once you got the bearings, there had done a fair number of interviews understood how the process worked and generally found good signal that, you know, you were able to assess whether this individual was a good fit or not. You'd become a phone screener, and that'd be someone who actually is on the initial calls.

Assessing the technical capabilities of this individual. And it would usually be more senior interviewers who would be really good phone screeners. And then for the folks who were incredibly predictive as to whether someone will be successful or not within the organization, they would actually become barometers and barometers are people who would actually be at the very end of the hiring process and determined whether to extend an offer or not.

And typically for any offer that was extended, there were always be two barometers. There there'll be actually a very, very vigorous debate. As to why would this person not work out? And a lot of the things that I've mentioned earlier about potentially the pre-mortem of how someone would not be successful as an organization was done during this hiring bar between the two barometers and assessing everyone's feedback, terming that.

So I'd say one key piece of how square really scaled this was. Setting up an entire ladder of how someone of progress and not putting people from day one on the critical path of whether someone would get an offer or not. And actually even before doing the first interview, it was mandatory to actually attend an interview training where some of the barometers that I actually come in and talk a lot about.

These are ways in which you should conduct the interview, not just from a technical side, if these are questions that we generally ask, but also what is important to experience, how should the candidate feel, how to talk to them, how to ask questions, how to make sure that the. Individual felt respected throughout the entire time.

And even the questions themselves, we. Always the economist and more so a pairing interview where you sit side by side and interview the person together. One big piece of this was it made the candidate not feel as if there was this again, strange power dynamic where interviewer and interviewee, where the interviewer has some questions.

And then the interview is constantly thinking, am I answering it properly? But instead when you're tackling a technical problems, we'd actually sit side by side and solve it together. The interviewer maybe point out like, oh, do you mind if I take over for a little bit type in some code show off how these are certain ways in which I would solve this problem and really make it feel a lot more of a, kind of like a peer relationship, which I think once you kind of establish that you get a much better sense of how this person actually perform on the job.

Did you lead 

Brett Berson: [00:25:42] some of those 

Rick Song: [00:25:43] trainings towards the end? In my time there? Yes, but I think there were a couple folks there who are absolutely incredible at this. Michael lassos is someone who I think. Has truly understood the art of engineering interviewing. He is someone who I think has had one of the biggest impacts on the entire engineering interviewing process at square.

And frankly came up with so much of the foundation of everything that I've spoken about here at square. The pair programming aspect of it was huge. And I think especially in oh nine, when most people are still doing white boarding for a lot of the engineering interviews, that transformation. To actually coding with someone else and sitting at the same computer, having two keyboards.

Side-by-side I still think it's the most successful way to actually interview engineers because I think too many companies focus way, way, way too much on algorithmic questions. I don't think it's actually fair, very useful as a signal for engineering interviews a lot, lot, lot more about. Like, how does this person react when they hit a roadblock on the interview process?

Like when they hit some challenge that they just cannot figure out and how do you help guide them and how do they respond to that type of thing? When you think 

Brett Berson: [00:26:49] back to the folks that you hired, that didn't work out. What are the key insights or lessons that you learned from that? And maybe how does that map back to how you think about assessing talent?

Because you've obviously spent a massive amount of time in your career thinking about this topic and working on getting better and better at hiring, but it's still an imperfect proxy for working together. Are there any specific insights or key foundational ways that you've changed or evolved the way that you interview based on the mistakes that 

Rick Song: [00:27:16] you've made?

I think there's two really big ones. The first one for all the folks that haven't worked out. They usually stem from an aspect of, we didn't understand the role itself nearly well enough. And this was particular prevalent for the first person in a specific role. We usually have a conception of, this is what the role should be like.

But we hadn't done it enough ourselves to have a deep enough understanding of whether this person will run with it or not. And I think this is actually a really good call back to hiring for potential versus hiring for someone who already understands the role. And I think one big piece of this is for those types of roles, we didn't understand it very, very well.

I think we had a tendency to hire much more so for potential. But farms of the company oftentimes are scaled the potential of this individual, which meant that the individual had to grow far faster than they may authorize even be able to. And in a way that frankly may be toxic towards their own growth trajectory.

And I think one big area for us there was really spending a lot more time on understand that role and do it ourselves and figuring out what else in New York city we need to hire for as well as whether we new hire someone who. Understands this role deeply, and, you know, it's there to operate versus hiring someone who can grow into it.

The second one, I think, where we've really learned a lot on goes again, back to this aspect of assessing the motivations of the individual. And sometimes we miss the mark in terms of like, what really motivates this person? What are they interested in? What do they care deeply about? And every single time, I always look back and try to think about what did I miss in terms of like what this person cared about, what this individual wanted to learn.

And I think we've had a couple of cases of this, where. We felt an immense alignment in terms of at least the core things around like people, about culture, about things like this, but didn't highlight nearly enough. Well, what are effectively the base requirements for a startup? And frankly, that means the immense amount of pressure that work-life balance can be very, very hard to achieve, especially in crunch periods.

And really highlighting what that scenario look like. And I think this is particularly came out for individuals who had not had startup experiences before 

Brett Berson: [00:29:23] on that note, have you noticed a pattern or any correlation if somebody hadn't joined a startup before and their ultimate success with you? Or are there big company, people that have been hugely successful, big company, people that have and vice versa.

Rick Song: [00:29:36] It's interesting. The vast majority of folks here at persona actually have no startup experience largely come from big companies. I oftentimes joke actually that we're an entire company of people who have never done startups, but are all trying to learn together at the same time. And I don't know whether that's a disaster or not.

I usually tell folks that this is kind of who we are, which hopefully makes a certain aspect of like, it's a very friendly learning environment for all of us. I think that there is a bit more risk to it, but I also think that there is a huge advantage to people who have worked at larger companies. And I think the two pieces there is number one, you generally have a sense of what is this function look like at scale.

And that's huge because companies grow so unbelievably quickly. Just knowing what the end result looks like. And then being able to plan backwards in terms of how we should get there is really, really impactful. Whereas I think if you've just been a startup, you've seen how it may be a smaller operation, but there's no ideas to whether it'll scale into something larger downstream.

And frankly, the scale portion may be far more challenging, especially given that the pace that startups grow at it's very easy to level out of whatever the last experience may have been. That said, I think the big thing for folks who have not. Experienced kind of a star before is more so the immense scrappiness of it all.

So I think like the best folks who generally succeed here are people from larger companies. We're really kind of like glue type who, you know, filled in all the holes at the company may have been a bit less recognized, but they were the ones who had to constantly like understand. Problems that no one else was really dealing with and like kind of flesh out everything there.

And a lot of ways, I think there's a very, very start-up aspect of that. We've tried to index a lot more heavily on that. Just essentially like these gap fillers that people would bring teams together and make everything kind of work out. 

Brett Berson: [00:31:20] I keep wanting to move on from recruiting, but there's sort of an interesting thread to pull on.

I think this goes against common wisdom. I think if you talk to most founders, they'll tell you all of these issues they had with hiring people from top 20 tech companies. And so you're sort of getting at this, but have you reduced down to the success thus far? Is this very specific type of person that's kind of glue utility kind of player?

Or is there anything else that you've done to get a relatively high hit rate in an area that I think often blows up in founders faces 

Rick Song: [00:31:54] two parts as to why this is the case? I think number one is there are a lot of founders out there who. Generally don't have experiences at a larger company. And as a result, I think there's a certain kind of foundation there where it can kind of be a black box in terms of how do you assess someone who can be so incredibly specialized and will they actually adapt well to a startup?

And I will say, I think a lot of folks who may have been at larger companies, a startup will be quite a culture shock to them. And very, very different from anything they've ever done before. And as a result, the risk of the individual will increase dramatically. That said, I think actually this ties very much so back into this notion of segmentation of the market, and frankly, why in a lot of ways we've been fortunate in terms of how quickly the team has scaled and grown.

We really look for folks who like. To help support others on the team and tackle brand new problem. It's just essentially like really an untapped market in terms of people who would otherwise join startups. And in terms of how do we kind of assess this? I think earlier, like, especially for engineers, it's a lot more about the questions of how do you think about the larger architecture and those people who really worried the utility player type engineers.

They can go so deep on so many different topics of the entire company. And if you ever hear this in a reference, I think it's huge, which is this person like. Seem as if they were omniscient about the entire company, if you asked them anything, they know kind of how it works. And those types of people I think are absolutely amazing at startups because they both know what the future will look like while at the same time be so scrappy in terms of understand how everything works together on the non-engineering side.

I think whenever we hear in reference, this person will literally run through walls to get something done. They will work with anyone. Those people I think are absolutely credible at startups. 

Brett Berson: [00:33:34] Go on an offshoot from what we're talking about and. Go back to the topic of culture, organizational design, the way that companies are run.

We had an interesting conversation recently around some of the incredibly successful companies, the last 30 or 40 years, and some of the work you've done to try to understand them and how that maybe influences the way that you think about running persona. And so I'd be curious to talk a little bit about that.

And some of it is grounded in this idea that ideally cultures are in service of some outcome. And they are not just necessarily good or bad, but they are tools to achieve some thing in the world. And maybe what you've noticed, if you look at square versus Microsoft or Google or Amazon, or all these companies about what makes them different in the way that they operate in the way they behave in the way that they manage.

Rick Song: [00:34:22] oftentimes like to start with this, which is when you look in the bay area, I think. 99% of companies out here we're effectively cultural descendants of Google. And I mean this, in the most literal sense, when I was at square, there were so many discussions, so many things that we did where oftentimes whether implicitly or explicitly defense would be well, this is how they did at Google.

And this didn't just happen at the engineering side, but on the cultural side from falling an OKR based model to even things like free food, how we structure company benefits. There's a very, very core Google us. Mentality here. And I don't think by any means that's bad. I mean, Google is one of the most successful companies of all time, but I think it has enormous ramification in terms of how this company will grow and, you know, the types of products that it's going to build and the types of businesses it will build.

And I think. One core thing about that is that although the Google methodology is incredibly successful, finding a niche and like discovering the nieces far larger than you could ever imagine. I think there's actually an incredible wealth of. Knowledge from other companies that didn't really descend from the Google philosophy.

And I'll, I'll call it a couple of companies that come to mind immediately. I love Shopify. I admire Shopify immensely, and I think it's always amazing to hear Toby talk about how a Shopify they don't think about people there. From the perspective of like two years, they think about investing in someone for 10 years, they're over in Waterloo and people who join oftentimes stay for five years and he speaks about how oftentimes it takes years before someone really develops and they're willing to make that investment because they've.

Create an entire culture about enabling people to be here for much, much longer. And as a result, I think an entire culture of respecting the historical value of individuals and that how valuable historical context can be for a company. You have other companies like Microsoft, who I think has absolutely perfected the aspect of, of what it means to build a platform, what it means to build a company with many different products and everyone, these products having their own go-to market strategy.

And as a result, Look, fundamentally very, very different from Google where Google has a huge amount of revenue. All of their still deriving from search Microsoft has one of the most diversified revenue streams in the world. If you think of it less so from, you know, just like, oh, they do software too. They have Azure and the entire Azure stack, they have office and every single product within office, all of which was, can be used independent each other.

There's both enterprise as well as for individuals. I think it's really, really amazing in terms of like how Microsoft is able to structure this. And again, Completely evolutionarily independent of Google. You have companies in Australia and Boston and many different areas. Folks like Atlassian, like HubSpot, who have all found independent cultural evolutions from the Google ask mentality.

So the reason why I think this is incredibly fascinating is oftentimes if you believe that culture is a huge indicator of the business strategy that you'll take, it's a huge indicator of the growth trajectory that you'll take. I think that the. Google asks type of strategy can be really amazing to build singular motto, product line type of companies.

But as a result, I think actually, if you look at a lot of companies out here, there aren't many who've really been able to succeed beyond that. Monopole kind of line. Like most companies out here are  with some sort of upsell type of motion to other types of products. But if you look outside of the valley, you actually see a lot of companies out there with it.

Many different entry points into their business. And I think one key piece of this is because the culture really is divergent. You look at companies like last year with dozens of products, all of whom can be used independently of each other. And all of them who are immense entry points into an ATAR at last and ecosystems.

Again, companies like Microsoft who have also been able to succeed in this way. A lot of companies over in China, Who have taken very evolutionarily, independent cultural paths. And I think that cultural piece is foundational towards enabling them to find these alternative business models. And I think that there's an enormous amount of value actually in exploring these alternative business models that haven't been treaded so much.

So, and I think in a lot of ways creates the opportunity to build much more innovative, interesting businesses that don't really resemble these hyper mono product line driven companies that we oftentimes see here in the valley. Whereas for persona, we really didn't find some. Singular thing that just clicked and our company just took off after that.

And then, you know, we're like trying our absolute hardest to stay afloat. Instead, we actually took a much more deliberate approach of constantly trying to test theories, testing hypotheses and constantly reevaluating. Are we setting up a foundation for something that could eventually be large and gradually building our way towards finding that growth curve.

And I think a large part of it's because we've. Really try to shoot what the typical playbook is of a company out here. So how 

Brett Berson: [00:38:53] does that influence the way that you approach taking best practice versus inventing in any facet of the company? Because in essence, I think we're talking about taking existing ideas that have been proven and applying them in your own company versus continually going back to first principles or starting with a.

Clean sheet of paper. When you have companies that aren't built in the bay area, one of the reasons they tend to maybe look different or have unique paths to success is there's not that level of cross pollinization that exists to your point about square with tons of people from Google. But as a founder, you can choose whatever you want to do.

And at the same time, if everything everyday was back to first principles, it seems like that's a tough or potentially slow way to build a company. 

Rick Song: [00:39:40] Absolutely. And I'd actually say this, which is we don't go back to first principles for everything that we built. It's very rare that we can go all the way back down to first principles for a lot of things.

Instead, it's a lot more about seeing where the trend is and then finding folks with it succeeded. Despite the trend being there earlier, we were talking quite a bit about hiring. And we have an relatively unorthodox messaging that we have for hiring, and that was rather emergent, but at the same time build off of things that we've seen certain companies say, and that were a little bit more unorthodox compared to what we were seeing in the market.

And I think the same as here, right? Which is we're not trying to reinvent the wheel and like find an entirely brand new is a strategy or a cultural strategy of things. No one else has ever thought of. That's why I think it's so fascinating to look at other companies and seeing things that maybe you don't see as immersion out here.

But really, really successful. And you don't see a lot of companies out there doing it again, like the Shopify example of hiring people for 10 years is wild. I don't know if it's quite applicable just given we're in the bay area and the requirements there, but I think there are really key learnings in terms of how they thought about things there and how they structure things.

I think it's really amazing in terms of how deeply coupled. Product and business are at Microsoft and how there's an incredibly deep level of communication and thought between product strategy and go to market strategy there that I try to study and see are there applicable things that we can apply to our business.

And I think that piece is much more interesting because at the end of the day, I can't figure it out again. I think it's incredibly difficult to figure it out. You know, what all the folks at Microsoft have figured out for the last 40 years, the folks that have lasted for the last decade or so. And instead, I think it's much, much easier to look at them and see.

Things that may be a little bit on Orthodox and then seeing how can we apply similar principles to our business? It's much less about trying to. Find things from first principles were actually much more about finding things that are successful, that isn't done as frequently. And I think oftentimes when people see that they may mistake this as suboptimal, but rather I think the one thing that we've consistently found true for building a business is that almost anything you can work, it's actually a lot more about how all of the pieces are put together.

Than trying to find the best piece for everything. I made this analogy to some folks here, which is building a team is not about like finding the greatest talent for every single role. It's actually a lot more about how does every single person work with each other. If you're building an MBA team, it's not about finding five all-stars, it's really about finding five synergistic players.

You can really play off each other. And I think the same really applies to building a business as well, which is it's a lot about finding different pieces and not trying to figure out, oh, what is the perfect thing? Like what did this best company do a lot more about thinking about much more holistically and how all of these parts interact.

It's a lot about trying to experiment with how this cultural value or how this operational value will play with the company. Seeing whether that works or not. And I think one example of this for us, most recently, a persona would be experimentation around stuff like, okay, ours versus frameworks, like jobs to be done.

And one big thing that I speak with folks here about is that none of these frameworks are perfect. Okay. Ours makes a ton of sense for Google, but that's also because they weren't incredibly. Metrics driven company where you could measure a millisecond or a render time difference or whatever that may be and translate that directly and company valley.

But if you're a startup and you're trying to figure out how to get launched, that may not make a lot of sense. If I had some magical metrics that I could just measure and know that my company is going in the right direction, I think that'd be absolutely incredible. But again, there's some aspects of it where if you understand your customer base, it makes a ton of sense.

But if you don't and you're still trying to figure out who your idealized customer is, it could make your product overly centralized in the demographic that doesn't make a lot of sense for your business. It isn't about just picking jobs to be done off the shelf, or, you know, it isn't about like, just picking off one of the things that are very trendy right now.

It's a lot more about looking outward, finding a lot of different things, figuring out the ones that really resonate with your business, piecing these together and kind of a holistic way. To build something that I think is novel and innovative and much more effective. So 

Brett Berson: [00:43:34] in your work, looking at a company like Microsoft, for example, who has done this brilliant job of being a multi-product company and a hugely.

Diverse revenue stream company. What is your guests or what have you figured out about what they got? Right. And maybe from that insight, is there anything that's being informed in your work at se oftentimes 

Rick Song: [00:43:58] how I think about things on this side is actually a lot more about. Whenever I hear something new, some new frameworks, some new ideas.

The first thing I actually oftentimes think about is when does this not work? What is the situation in which this would not be effective? And I think that question actually oftentimes is far more interesting than why does it work? And I think there's going to be applied to so many different things from engineering to people to hiring to everything else.

Because I think oftentimes the question of why would something not work informs a really big piece of what is the element of it that actually makes this work, right? Like where's the decision point where suddenly something went from not working to working. When you try to look at something where it'll just work.

Like, I think it's really, really easy to just constantly have confirmation bias yourself into believing that this is the optimal decision. So I promise this will tie back into Microsoft, but to go back to the notion of jobs be done, which has been incredibly invoke, I think within the valley these days, The first thing I thought about actually, when someone introduced this framework to me, Was what would have to be the characteristics, a company where you wouldn't want to apply such a framework because whoever creates Jossie, Don, these coaches out there who are teaching people, how to execute such a framework within your own business.

There's very little incentive for anyone to actually tell you, this is not a good idea for you as a business when you're early as a startup, and you don't understand your customer very, very well. It's actually. In my opinion, really important to hedge out and be able to try to target different customer segments and see, where does the market pull you?

Where are you finding market demand? And as a result, I actually think d'Offay done for very early stage. Customers are still trying to figure out what their customer profile looks like. It really doesn't make a lot of sense because, you know, if you tell yourself, oh yeah, I know what the customer looks like.

You're probably lying to yourself. And if you don't that you really can't apply to jobs to be done framework at all. So to tie this back into Microsoft from a face value type of perspective, I think what works really well for them is they've clearly found a way to consistently execute on new product lines and be able to sell into existing customers for them.

And I think that you consistently see this from anywhere from Microsoft teams to all their work on Azure and how they've been able to have me at this pace out scale. GCP growth. But then I think there's a lot of things that you have to ask. Why are other companies not able to replicate what Microsoft has done?

What has not worked for others that has to work for Microsoft? That has to be this idea of product and go to market are actually really in lockstep to make sure the value proposition of what you're building. Has immense potential sell. Why has other companies out there struggle a lot more on the side of building multiple products with really powerful entry points in the market?

I think it's because oftentimes when you're early stages to start a pocket business are literally joined by the hip. But as the company scale, you start seeing these two functions divide more and more. Whereas at Microsoft, it clearly seems to be much more embedded with each other at the same time, again, to go back to this idea of what doesn't work about this, I think there are really key pieces from anywhere.

Prioritization and having your roadmap be overly dictated by maybe sales or by customer success or things like that. And with all of that, you suddenly start seeing like this push and pull of how do I have to modify the entire equation of this company to still make this entire formula workout? What are the trade-offs I'm making?

What would the evolution of this company look like two years down the line where we've really focused on this, but now we've become a bit weaker on this area. And I think oftentimes, I mean, just like engineering, building a company is very, very similar to this whole idea of, there are so many trade offs that you have to make.

And there just isn't a perfect formula for any type of company. And frankly, any trade offs that you make it'll emerge actually two years down the line and the company will evolve again to adapt to these trade-offs from how the business is structured, how the organization structure, how teams operate to adjust the trade offs that were previously made from decisions two years ago.

And right now for us, we've taken a lot of inspiration from how do you build a platform by looking at companies like at Lassie and looking at companies like Microsoft being inspired by how they were able to execute a bottoms up, go to market type of approach for companies like Atlassian or a top-down enterprise sales type of approach, but both of whom with made different product lines with many entry points and thinking very intently about what works about them.

And more importantly, what were the characteristics of company have to look like for those things? Not to work. 

Brett Berson: [00:47:54] If I was watching. Or looking at the way that you're operating today, what is unique about it, or how are you behaving as a team today that will decrease the odds? That you'll be a mono product company with an existential question five 

Rick Song: [00:48:10] years from now.

So one of our core themes right now as a business is decouple. And it's the idea of how can we enable many teams here to operate independently each other. And that means anywhere from how do they go to market? How do they target the first customers? So we have initially, so product line that seems to found some sort of traction, and we're already trying to explore like alternative products that would hopefully can find their entire own entry points into the market.

We have smaller teams, teams about five people, maybe three engineers, one designer, and one product manager. And everyone on here is thinking about, go to market. It isn't just about, oh, how do I upsell existing customers? It's please cold email people and try to figure out whether this product resonates with them without trying to sell them our verification product.

And seeing if people resonate with this and finding their own kind of go to market trajectory with the expectation that very likely they'll fail many times before getting it right to really highlight that key differentiator. Because I know many organizations out there I've already know spot, hopefully a second product, or the second feature sets.

Is that relentless emphasis on go to market and the relentless emphasis on how do you actually sell and spreading that knowledge, not just hiring an a for that team and telling them, Hey, can you figure this out? But really every single person has to embody it. And that means engineers are cold emailing people, having some of the most uncomfortable conversations of their lives.

And the same way that Charles and I did for our first conversations with potential customers, having PMs think every hard about pricing, about what actually resonates. Having designers not have the opportunity to do huge user studies, but instead have to study competitors and have to deeply understand the industry and prior art while they're trying to do, I find that 

Brett Berson: [00:49:45] really interesting, that insight around like it's everyone's job to think about.

Go-to-market. Is it something you just talk a lot about and push people on or are there rituals or practices or things that exist in your company that is unique around that 

Rick Song: [00:50:01] behavior? Now I would imagine that every single person here is incredibly tired of me telling them how important it is. To understand, go to market regardless of your role.

So I think one part of it is definitely that, but the other part I would also say is we put a lot of emphasis on trusting individuals here and making sure that they really feel like owners. And I always tell folks that if you're an owner here, that doesn't mean, oh, you just owned, you know, equity or you own your own project.

It's the same expectation I have for myself, which is you own this business. And that means understanding the business. Much wider than you otherwise. Imagine trying to go deeper at the same time. It's a very, very uncomfortable balance, but you have to do both. And that means thinking about things that may not be in your comfort zone.

Every single engineer here, isn't a customer channel directly interfaced with customers. Every engineer here has been on a sales call. Most engineers here have had to try to, you know, speak during a sales call and actually sell. And I think hopefully the belief is that as we continue to scale, it isn't so much a ritual anymore.

As much as you're just going to hear it, no matter where you go in this, 

Brett Berson: [00:51:03] one of the ideas that you seem pretty obsessed with is pre-mortems right. Thinking about why things. Might not work in the future. Do you have thoughts pre-mortems as to why this strategy and this desire to be multiproduct relatively early on may not work.

Rick Song: [00:51:19] Absolutely. I mean, one of the greatest fears here is we lose focus and we stretch ourselves too thin. And we're trying too many things, the idea of like, trying to go about and figuring out a multi-product type of approach really came from this idea of we're trying to build a VC backable business for myself.

I didn't feel this immense confidence that, oh, you know, like I know that this will suddenly become absolutely enormous. So. I felt as if, if we could create a culture where we can keep building new businesses, eventually this has to be venture scale. Or like if we've created an entire culture where we can constantly launch new businesses, that'd be possible.

I felt a lot of motivation because it felt like it'd be a culture, which is much larger than myself. It wasn't like Rick, hat's a brilliant idea. And then therefore this company went off and fulfilled it, but rather it became a company where a lot of folks here have amazing ideas. And my joke with people here is my dream.

One day is that every day I walk in and I'm absolutely surprised by the things that we're working on. Feels, if there was no way I could have ever come up with this. And obviously the bonus of it all is it felt like this, if successful would definitely be something that really would be venture scale.

And therefore, I never felt like this looming fear that, oh, what we pitched to investors, isn't truly something. Yeah, we'll be back. So I think those are the core pieces that went into it, but I think there's a lot of reasons. That's why we might fail. If we can't execute the pace that we have to, if this idea of like synergy between our different products.

It isn't necessarily just stick as we once thought if this culture actually is non-scalable and it caps out at like a hundred people, I think all of these are great unknowns for us. And we have a faculty traded market risk for execution risk. And I think at the very least, I feel a little bit more comfortable with that trade because the market risk one just gave me way too much anxiety.

Brett Berson: [00:52:55] I'd love to. Conversation by talking about your thinking and frameworks around decision-making at a startup, and you kind of have this idea of saddle points, and we'd love you to share that and use that as a place to wrap up our 

Rick Song: [00:53:10] combo for a lot of early stage startups. And honestly it starts at any size.

You'll be just bombarded with advice. You'll hear that X company did Y and so successful in a work so unbelievably well, whether that be okay, ours are frameworks for product decisioning, like jobs to be done or otherwise. And I think for us, one of the more interesting things, I think that we really think a lot about Episona.

Is all these advice are correct, given the right context. And I actually think what's much more interesting than figuring out whether this framework is the perfect thing and how to execute this frame perfectly. How do I implement agile at my given organization is actually when does it not work and actually finding that saddle point for the decision discovering what are the characteristics of this framework that makes it effective and not effective.

And I think that's actually true for so many different things anywhere from. Hiring to, how do we make product decisions? How do we prioritize? This is something I think we encourage a lot at persona, this idea of system space, thinking, thinking a lot more about not the execution of a given framework, but rather how does this play in conjunction with all of the other kinds of frameworks or all the other processes?

The other ways in which we make decisions at persona, I've been a very, very big fan of internally. Lately has been this idea of saddle points of decisions. And this concept originally comes from game theory, but I find it unbelievably fascinating, which is oftentimes as individuals, we focus way too much on one decision versus another, but not nearly enough about like this meta question of.

Depending on the context of a scenario, when does that decision change? And I think I touched on it a bit, but I feel as if it's become applicable to almost everything that at least I think about these days, that persona where it's actually becomes less and less about what decision is right right now, but a lot more about systems based thinking what has to be true in which one decision will be right versus one versus wrong.

And like, what does that mechanic? And once you understand that, actually the framework comes far, far more interesting and suddenly it becomes much less about we didn't do this or that, but more about. How do we figure out the context in which this situation would be true of the saddle point borrows from in game theory?

This idea of there is a specific point in which the decision shifts like where you were originally going to be like, I'm going to bet, and now it's like, I'm going to fold and what has to be true for that saddle point or what are all the criteria that have to be true, where your decision will flip? And internally, you know, especially on the product, as well as like the business side and pushing folks a lot on this.

What is the saddle point for this decision from, I earlier mentioned jobs to be done, but on hiring, like what has to change about our business, where we wouldn't hire this person anymore, you know, or we would hire this person or we need, can you give 

Brett Berson: [00:55:40] a couple examples of what this looks like maybe on a day to day, week to week basis?

And I'm curious about how you operationalize. 

Rick Song: [00:55:49] So I think, uh, the core of how to operationalize that, and then I'll give a couple, examples is really about. The question a lot more is not so much. How do we make this work, but rather changing the question to when does this not work? And I think you can apply this to almost anything out there.

For example, why would a customer not want this? Right? Is a far more interesting question oftentimes that why would a customer want this? Even like, beyond that earlier, we talked a lot about hiring. Why will this candidate not work? And suddenly, like once you find both a point in which this will work, oftentimes you're working on a product idea.

There's a thesis for why you believe this is right. But once you can also find the counterpoint, which this is a scenario where a customer would not want this. You can now start teasing out. When does this make sense and really finding out like what the target demographic is and understanding a little bit more and uncovering the entire system of how that works out.

Why do you think 

Brett Berson: [00:56:35] it's so useful or maybe so often overlooked to think about why things might not 

Rick Song: [00:56:43] work just as humans. We're oftentimes much more wired to think about things. Procedurally X causes. Y causal things are just easier for us to, uh, go through. And as a result, we oftentimes think a lot more about the execution of something.

Rather than the concept of it, or how does this entire system work? Toby from a Shopify often talks about how systems based thinking at Shopify is a huge part of everything that they do that it's not so much about, oh, if we do this, then this will happen. But rather if we do this, how has the entire system as a whole impacted?

And I think that's a really hard thing to build in culturally. And frankly like the leap from causal based thinking to assistant space thinking it's a very large awesome, 

Brett Berson: [00:57:19] well, I am hopeful that our conversation and, and you specifically. We'll have that type of impact on some other people that are building companies the day.

So thanks so much for being so generous with what you shared and spending all this time with us. 

Rick Song: [00:57:31] Absolutely. Thank you so much for taking the time.