December 14, 2022

Scaling organizations w/ Jared Fliesler, ex. COO Scribd, VP UA at Square

We’re honored to have Jared Fliesler, growth master, founder and startup advisor who has years and years of experience taking companies through hyper-growth.

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The host

Nima Gardideh

President of Pearmill, ex-Head of Product at Taplytics, ex-Head of Mobile at Frank & Oak. YC fellow.

Our guest(s)

Jared Fliesler

VP UA, Square. Ex-COO, Scribd.

About this episode

Jared Fliesler is a master at organizational design and growing products for Google, Square, Slide, and Scribd. He now advises startup founders how to build better, faster and stronger companies. He’s helped them raise over $60 million in growth capital btw.

He shares tactics to use as a founder to stay connected w/ a growing team, plus how to be a human centered founder.

More episode highlights:

  • His vision for operational and organizational design that scales.
  • Creating effective feedback loops for growth.
  • The cultural forces that impact a career path in tech and how to advise your team on either an IC or management path.
  • What the principle and SWAT team model is.
  • Breaking down tabletop management.
  • Knowing when to be a driver of company culture and when to be a passenger.

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[00:00:00] Jared Fliesler: Can you feel as much impact from being part of something, part of a company, part of a team, part of an organization, even if it's not just your work? I think the answer is yes. Like I think CEOs of really successful companies feel an incredible amount of impact in the world for the company they're building, even though they have hundreds or thousands of employees. But it does require a bit of a psychological shift in us to step back from the, like I am my work into, I am satisfied and fulfilled by being a part of something that's bigger and trusting that your guidance, leadership, whatever it is, helped to make that successful. 


Transcript of the episode

[00:00:43] Nima Gardideh: Welcome to another episode of "The Hypegrowth Experience". I am your host, Nima Gardideh. I speak a lot if you've been listening to these, especially I speak a lot about how organizational design and the way you structure teams and motivate them is a huge part of growing products and companies and marketers alone are maybe not the best folks to talk about this more sort of general concept. And so, I was very happy to find someone that had experience on both sides of this having grown products and then having become more of a c of a couple of different companies to structure teams and create operations and make sure that not only are you grow.

[00:01:31] Your user count, but also the company itself in order to match that pace of growth that's needed. I'm so happy to have Jared Fliesler on this episode. If you don't know him, he's been at Google before, he was a VP of user acquisition at square. He was a COO of Scribd at some point, and now he's coaching founders on how to scale their organizations very well, and the structure of the conversation is a little bit different.

[00:02:01] It's much deeper into the specific topic itself, which is organizational design and how to grow teams and how to think about incentives structures that you can put in place for an organization to make sure that you are managing people well and you're helping them grow within the organization and ultimately grow the organization and the product itself.

[00:02:26] I'm so happy that he was able to do this with me. He's quite of a busy person these days and has a lot of experience in growing these hyper-growth companies. We start with his journey in how he got hooked into the startup ecosystem and marketing and growth early on. Here's Jared. 


[00:02:47] Jared Fliesler: I mean, I wish I could say that there's some magical through line and I had it all figured out from day one from when I was a little kid. You know, when I was really young, I wanted to be an architect, and I went and studied marketing. When I was in college, I got really obsessed with advertising and this idea of storytelling and how companies basically communicate what their product is and what their service is to people and get their message across as succinctly and creatively as possible. 

[00:03:16] And then I found out what it was like to work in advertising and realized that was not something that I actually wanted to do. ANd instead sort of think about how do brands do this? How do people with products or businesses with products do this? How do they communicate to their users what they can bring to market? What problems they're solving, things like that. And that's what I started doing. 

[00:03:40] And so I started working at startups. I just sort of fell into it. I had a friend who worked at a startup and he said, what do you think about working on the internet? And I didn't really know what that meant, and I was totally hooked. Uh, just this idea that all of these people were coming together around some shared purpose and that they were really excited about it and that they were working really hard at it, and that it fell outside the normal kinda nine to five check the box punch in punch out mentality. I just loved that. I loved being part of something that was really meaningful and that there was a strong culture around. 

[00:04:14] And so, that is what startups were for me. And then I got addicted to the impact side of it, which is just this idea that you could come up with a concept and brainstorm it and it, it's on a whiteboard or it's on a notepad on Monday and on Friday it's built, and on the following Tuesday it's live. And on the following Friday, it's a week later after it's been, You have thousands of users that are writing you on Twitter or before Twitter. You know, writing in and letting you know what they think.

[00:04:45] Just this idea that you could have dreams and that those dreams could quickly becomes something tangible that other people could touch and interact with was such a cool and different concept to me. It was this like rapid fire building and so I got really excited about that, both about these ideas, being able to come into the real world and then the scale.

[00:05:10] Just the sheer idea that you could touch hundreds of thousands or millions of people or billions of people with your product and actually have them benefit from it. And so that kept me in the cycle of just getting really excited about startups and what they were doing. I ended up being an executive running growth and operations, and I went to Venture for a while helping other people who are starting their companies to hone their ideas and invest in them.

[00:05:33] And then I went back into operating as a COO and was really across a whole bunch of different areas across product and marketing and business insights and operations and HR. And so I've gotten the taste the rainbow and see lots of different things. And now I've stepped back and work across a number of companies helping their CEOs to scale their companies think about senior hiring, think about their commercial and product strategy, and to practice difficult conversations, especially right now given where the economy is. Lots of tumultuous times that CEOs and founders are having to navigate. And so I work with them and sort of like a coaching slash board member capacity of helping them out, but from a really functional perspective of having been in their shoes and run companies.

[00:06:25] Nima Gardideh: Yeah. And I feel like that's a similar thought process I had when I was younger, thinking about technology. Is there a, and I feel like you probably have a good answer for this impact portion and the way you put it was quite interesting where there was a personal impact to what was about to happen. So you dreamt of something, you worked with someone and a team to build it, and it went out there. And then there's like this other part of impact, which is the people that are then affected by the creation. So there's like the users that come in and use your product and hopefully get some value out of it.

[00:07:01] Do you feel like that level of impact is still palpable as you scale up a company? For you as an individual, do you have to sort of forgo some of that? Like what is like the version of Jared that's still excited to be in these bigger companies, versus these smaller ones that maybe the input that you have as an individual is much more connected to the output, or do you feel like that can always be true so long as the structure of the company's designed in a proper way?

[00:07:30] Jared Fliesler: Yeah, I think it changes, so I think one of the hardest things, Is that the satisfaction that we learn as individuals early on is in our direct work product, right? So if you go back to, you're in school and you get an assignment, and you do that assignment, your satisfaction comes from completing that assignment and then some extent external validation of a teacher saying, Hey, you did a great job.

[00:07:56] And so it's all really within your own sphere of influence. And then at some point to put you on a group project. And now you're in a group project where there's five people that are working on this collective output. And so this question is effectively, okay, well when that collective project comes out and you, there were five people and you only did 20% of it, do you feel more satisfaction, the same satisfaction or less satisfaction than if you had done the project yourself? I think the young version of ourselves, the immature version that had all of our satisfaction connected to our direct work product probably feels less satisfaction because they look at that and for 80% of the time, it's not their work. It's not them speaking. It's not them presenting. It's not what they've covered.

[00:08:48] And so they feel awkward, like, wait, but I only did a fraction of this. It's not all mine. I don't get to take credit for all of it. I don't get to, this isn't my work. And so the maturity comes and sitting with that and going, yeah, but look at the project that we did. I could have never done a project of this scale myself. I could have never covered this many areas. If it were just me, I would've just done maybe a quarter of this work or 20% of this work. I'm sure it would've been a hundred percent me. But it would've been a much smaller project. 

[00:09:17] And the same thing happens when we go into the working world, right? So we started as a junior IC and maybe we're a designer and we're designing things, we're working on that. And then at some point we get promoted to being a senior designer. And generally what that means is just like, Hey, your ideas are really good. Now you should have more independent ideas. And so we're having these independent ideas. Great. We're receiving accolades and praise for them being our ideas and us executing on them.

[00:09:42] And then we become a lead and now we have junior designers that are working on our team and we're directing their work. And when the work gets presented, Really good managers or leaders say like, oh, well that wasn't me by the way. This is Sarah. This is Bob, this is their work. And so we have to shift our satisfaction that comes with being the coach, which with being the lead, being the person that was helping them get there.

[00:10:09] And this grows as you manage a team and then at some point maybe you manage multiple teams and then multiple functions, then maybe entirely different areas of your businesses. I think it becomes this hard thing. But going all the way back to the question, like can you feel as much impact from being part of something, part of a company, part of a team, part of an organization, even if it's not just your work?

[00:10:31] I think the answer is yes. Like I think CEOs of really successful companies feel an incredible amount of impact in the world for the company they're building, even though they have hundreds or thousands of employees. But it does require a bit of a psychological shift in us to Step back from the, like I am my work into, I am satisfied and fulfilled by being a part of something that's bigger and trusting that your guidance, leadership, whatever it is, helped to make that successful.

[00:11:01] Nima Gardideh: Yeah. And that resonates a lot of, and the way I, and by the way, just to, for the listeners, IC stands for individual contributor. There is a part of this that, I think about as that your craft shifts as you go through these stages and you can still get a similar, let's say positive feedback loop of sorts from that craft. It's no longer. necessarily me going into the tool Figma or whatever it is, and designing the, buttons or the user interface or the experience, the craft is leading the team. And so that in itself can be what you put in the work and get feedback loops around.

[00:11:48] I'd love to hear. So you started, I assume, as an individual contributor as well, and then have gone through these different stages of companies and you attributed some of it to maturity, which was interesting to me cuz I also feel, like you immediately triggered a thought in me of like, I remember being younger and wanting everyone to know that the reason this product is out there or the reason this thing was designed or created was me, where I do not at all care about that now as an adult.

[00:12:20] How much of it do you think is just a shift on a perspective? It's maturity of like, maybe I needed my brain to pass 26 and then I have my frontal cortex built out and I can think about people beyond just my immediate consciousness. Like, what is it that you feel like needs to get triggered? Number one. And number two is, do you feel, like everyone should go down this path of changing from an IC to a leader?

[00:12:48] Jared Fliesler: Yeah. Okay. So let's start with the first one. So I do, I think that everyone needs to go through this process and do I think it's just a matter of age? I think that some part of it, when I say maturity and I remember also young Jared being like, oh, but I'm really mature? And other people saying, oh, but you're a really mature version of a 22 year old, whatever it was.

[00:13:15] When I think about it, I actually just mean time. And I think that it's like we grasp at the thing that is right in front of us if we don't have any context for something that's further out. So it is just easier. If you can touch it, if you can hold it, if it's your work product, it's easier and you're trained to do that.You're trained to do that in school. What's your assignment? Put the name at the top of your paper. What grade do you get? 

[00:13:41] And I remember, having employees where it would be their first job out of college. I remember one employee saying to me like, Hey, but I'm used to more feedback. And I thought in my head, well, we meet every week and we're having a one-on-one and I'm giving you feedback.

[00:13:57] What is it that you're expecting? And as I dug into this, they were like, every time I turn in work I get feedback. Normally, when I'm in college, I hand in a paper and I get feedback, I get a grade I get told, not just, here's some feedback, here's how good it is on an absolute scale, and here are the edits and here are the changes, and here's what you need to do.

[00:14:17] And in the workplace, when there's a million things going on, generally you get feedback less frequent. It's less specific, it's not direct edits. You'll often get feedback like, oh, well can you redo that? Like, I think it could be more fun. I think it could be more playful. I think it could be more aligned with our target market. I don't like the language of that. You get feedback like this and you go, what do I do with that? 

[00:14:36] Nima Gardideh: Yeah. Especially at a startup.

[00:14:38] Jared Fliesler: There's a million things going on, and so it's really hard when the feedback you're used to getting is so specific and so pointed and so frequent, and you have to switch to, oh God, now I have to give myself feedback. I have to find satisfaction and fulfillment and confidence and build that in myself. I'm not having somebody else tell me, Hey, pat on the back name a great job. Like you get a gold star today. And so I think that is a process that you go through. When I talk about maturity, that's a process you go through of just in time doing that for yourself, self soothing, believing in yourself, building confidence by doing it over and over and over and over again.

[00:15:18] And so in the early days, When you have this work product, that is the easiest way to know that you've done a good job because you did a thing and that thing people think is good, therefore, you are good. Right? That's pretty direct. It takes a while to build the influence where other people even want to follow you.

[00:15:38] Where you're guiding, you feel confident and have awareness and experience in guiding correctly. And where other people receive that guidance and appreciate it and where you get to sit next to them and their work product and hear the praise they receive for their work product and just know somewhere deep down inside that you had some role in helping that get to that work product, right? I think that just takes time.

[00:16:04] There's two things that stood out for me, that I wanna repeat back to you to see if it makes sense. One, you talked about time, and one, one thing that came up is that I, it felt like you were talking a bit. that the time scale of things matter more to you as you're older because you're willing to sort of have a slower feedback cycle.

[00:16:29] And that's something that definitely stood out. And then I feel like I definitely feel some attachment to that idea. And the other part was this turning of the feedback loop from the outside world to your inner world. And I talk a lot about this wwith my team and a couple of people who've come on the podcast about mastering your craft. And that the underlying process that everybody talks about is similar in that you have found a feedback loop of sorts or you have created your own feedback loop that is independent of the outside world, focused on being better at whatever you're trying to get better at. Does that, those two things felt like they stood out to me from what you just said. Does that make sense?

[00:17:20] Yeah, that it resonates. I think on the first one as I've gotten older, I've just slowed down a little bit in my expectations. The like instant gratification. I need something immediately back in order to feel fulfilled. I become more patient, more relaxed and understanding. And so I think having experiences where I didn't get immediate gratification or feedback and it ended up being okay, like having those positive experiences allows you to govern yourself and your emotions through those lived experiences. Versus I think your default is when you haven't had those experiences, you're hypothesizing about what might happen, and that's a mix of excitement and possibility and fear. 

[00:18:06] And fear is just such a strong emotion. And so I think you can often get in the mode of fear. And what happens, especially for younger employees, is they come in with a bunch of fear and insecurity and not enoughness. And so in the absence of that external validation saying, Hey, you are enough, and here's instant feedback, and here's an A on that paper, they're like, oh, I haven't heard anything it's been four hours. I guess he didn't like my idea. He hasn't responded in my email. I wonder, why he didn't like it. I wonder why it wasn't good enough?

[00:18:41] And so it, it's this really dangerous thing and I just think it takes us a little while to build that steadfastness in ourselves that we understand and know that we are good at what we do, and that we're not seeking that. And that's that internal cycle. That second thing you talked about where, I don't know if we get to say that it's completely divorced from external validation. It may just be that after 20 years of receiving external validation, you no longer question whether or not you're a good CTO that you're like, you know what? I've done enough projects, had enough clients, had enough external validation. That one more piece of external validation does very little for me. It's a drop in the ocean, and therefore I just sit in all of that external validation and feedback and know that I'm good.

[00:19:28] I think we'd like to say that it's all. But I imagine it's heavily shaped by all of the external feedback you've received over years and years. At some point, it just becomes you knowing that you are good, partially informed because other people have told you you're good, partially informed because you have data of projects that you've done successfully, outcomes that you've driven, and whatnot.

[00:19:48] And so now, instead of it being the subjective third party, defining whether or not you are good and worthy and secure and should be confident, you now have real objective data mixed in with that subjective stuff that you have a strong, grounded opinion on yourself and one brand new idea that's a subjective opinion from somebody doesn't dictate and sort of overwrite that in a way that is earth shattering. And that's what I think you get in time and just in having those data points.

[00:20:21] Nima Gardideh: Yeah. And a lot of this also like, makes me think about how a lot of the best forms of competition I've had has either been with myself or in environments where everyone's collaborate collaboratively, compet competitive, as opposed to maybe negatively competitive in that there is like a zero sum game people are playing.

[00:20:43] And so you're able to improve much better in a sensation of a positive sum competitive game just because of that sort of nature is a very similar process to me. 

[00:20:57] What is this? So let's go through this cycle. You start as an IC, you decide to become a leader. I think we talked about that briefly. Why, and I think this is maybe very unique to the tech industry. I'll preface it by that, but not everyone needs to become a manager of folks, at least in our industries, where you can be the best engineer in the world or the best designer in the world without ever managing people because there are paths for you to become, the master of that craft over a 30, 40 year timeline, without ever having to manage people.

[00:21:32] But do you recommend that path to everyone? What are the things that people should be asking themselves before they decide to go down any of these paths?

[00:21:43] Jared Fliesler: Yeah, so, so I wanna dig into something you just said, which is not everyone needs to become a manager or leader. You can stay an IC. There's lots of room for you to become an expert at your craft. I think that is an objectively true statement. And I think almost every single force in nature and in our ecosystem pushes you away from that.

[00:22:03] And so let's talk about like, what does that mean? Well, for example, I think we teach people that there's this pyramid. In high growth technology companies and for type A people, for people that are overachievers that were pushing around progression, we're constantly pushing them up this pyramid. Like, do more, have more responsibility, have a higher title, make more money, have more control, whatever it might be. Like we are encouraging people to climb that ladder and we're applauding them the whole time, right? When we do promotions, we make a big deal about it. At most companies, like, this is an accomplishment. This is objectively successful, right? And more so I would argue than people that stay in their craft and just get really, really good at it. 

[00:22:50] And so I think that we have a desire to seek growth and change in people environmentally. And so that makes it really hard for people to say, Hey, I love being an engineer. I don't need to change in terms of what I'm doing. I'm gonna be an individual contributor. I'm really good at what I do. I'm gonna keep learning more. I'm gonna continue to be really good at what I do as the environment changes and I'm happy, leave me alone. And having us say, oh, that's fine. 

[00:23:18] And so what I see happen is that we take people that are really good at what they do and we go, well, wait a minute. What if you let a whole team of people and and maybe you can make them as good as you are. Maybe you can train them to be as good as you are. And most people receive that and go, oh, well what does that mean? And you say, well, it means you'd get promoted, you'd get paid more, you'd have more responsibility, you could have more impact.

[00:23:45] And most people hear that message and go, oh, well that sounds good. That sounds like what I should be doing. Right? That sounds like the path to success. And so then they get into this role of managing a team. Which has some similarities to doing the work themselves, but training other people to do that work, recruiting those people, managing those people, coaching those people, firing those people, if they're not good and replacing them. That's all pretty different than when you just were heads down at your station kind of coding away and doing your work. 

[00:24:14] And so I think we, we sort of take that for granted. And the reality is every CEO manages people. Every single one. They have at least one direct report, generally more. And so if you wanna go to the top of that pyramid, the path to the top of that pyramid is leading. It is managing people, it's leading teams, it's doing things that are not just individual contribution work.

[00:24:38] And so it's this hard thing where people feel pushed to keep climbing that ladder. And at some point the, I'm an individual contributor piece gets in the way of that progression in most places. Even at Google where there's like staff level engineers and there's very, very senior individual contributors. Still, their bosses are people managers, right? And so I think there's this tension that people feel in their career to become a leader, to become a manager. And I just think we have to be honest about that, that exists. 

[00:25:12] And it is true that at the top of the pyramid is a manager or a leader of some form, doesn't mean you have to. But it does mean that you're probably gonna be going against external forces that are constantly pushing you in that direction, and to have awareness around that.

[00:25:27] Nima Gardideh: I wanna ask you a meta question, but I do want to, have you go through what are the questions you should ask yourself to choose the other path, which is the managerial path. The meta question is this, do you think and based on what you just said there, is there, there are cultural forces that create this pyramid that tell the story of success and that you should be climbing this pyramid in order to sort of match that story. 

[00:25:58] Do you feel like there are structures out there that have either been tried that or that people or founders should be trying in organizations that mitigate this problem or completely get rid of it? Especially in the world we're in and I think you and I have both hopefully had the pleasure to work with engineers that really are incredible at the craft of engineering itself. And I would far rather have them dedicate their whole lives in maintaining that excellency of that craft. As opposed to spending any time learning how to manage people and set expectations with, than communication and all the different things that come with management.

[00:26:41] Do you feel like there are structural organizational design paradigms that people should explore that maybe enabled us more people becoming just craft experts as opposed to leaders and managers in the way that maybe we're defining here.

[00:26:58] Jared Fliesler: Yeah, so I've seen some of these. So there's, I don't know if I would lump leaders in, cuz I think, as soon as you are a really senior individual contributor, you're generally starting to lead design and thinking, and then that means that those are your design and thinking ideas, and you should probably be leading with them.

[00:27:18] Now, doesn't mean that you're gonna coach people on executing to them or manage people's salaries or have one-on-ones or, talk to them about their feelings or whatever it is that might sit well outside of this. So let's split those a little bit. I do think there are lots of organizations that have, instead of pushing they're senior folks to become managers they push them to become leaders and they've specialized, they've had people that basically become specialist managers that have lots of direct reports, and those people are responsible for reviewing compensation and doing one on ones and project management of workload and things like that.

[00:27:56] And meanwhile, there's a tech lead or a design lead or product lead that is leading the think around that area and the strategy around that area, and that person is still acting as like a senior individual contributor. and leading as in they might have a talk or they might due to the design docs or they might set the direction.

[00:28:18] And so this is maybe the like happy medium of finding that middle ground where that person doesn't get bogged down with administrative management of a large team. They still are leading and they still are doing the individual thinking that comes with them being an expert in their craft. I think that can work well.

[00:28:37] That is basically the rise of the CTO with very few, if any reports versus the VP. This is a pretty good example of this where a CTO may be setting some of that technical strategy. So I definitely think that that happens in different organizations and that people have explored doing that. I do think that you wind up in these places though. Almost without fail, where those people that never wanted to manage anyone end up managing people or getting asked to manage people or feeling like they need to manage people.

[00:29:12] The other thing that I've seen used is these like black ops SWAT teams. So back, like 15 years ago, we would have, like the server engineering. And that team was thought of, this is like before iPhone apps and whatnot, that team was thought of as the Elite Forces engineering team. 

[00:29:39] They were led by the CTO, maybe managed by the CTO and they were the best, most elite engineers that we had at the company. There was no expectation that anyone on that team was gonna become a manager or going to become the CTO. They just reported into a very senior person, and they did really exceptional work. They could become the lead on certain areas, but their responsibility grew through ownership of infrastructure and ownership of areas of the code base ownership over technical decisions, not ownership over employees, ownership or management of other people.

[00:30:20] And so I think there are places you can explore that too, where you basically give people more and more responsibility. But as an individual contributor or as a lead. And that's another way to encourage this versus pointing people down a road to management.

[00:30:35] Nima Gardideh: Yeah. The way I had characterized that first version of the thing you talked about, there's a lot of direct reports into sort of single people. I've been in organizations where they call that the principal model, where you have these principal engineers that do a lot of more technical work, but they don't have a lot of direct reports.

[00:30:53] And the SWAT team thing is interesting. It sounds like you have, you're still a given responsibility, but it's infrastructure responsibility in the code, not necessarily people responsibility of how the intricacies of communication and goal setting and things like that work. Yeah, that's, it's an interesting area for companies to, I think, still experiment with it, as we've learned over the last 20 plus years of the internet. Well it's back over 30 years now. We're all getting older, but, over 30 years of the internet, I think there is, there's a lot to still experiment with this general area. 

[00:31:32] I think, let's say you're in one of these normal organizations and my normal, I really mean, what we talked about earlier where there's like some form of a pyramid. It's much more classical in that sense. 

[00:31:46] How do you think about and I want kind of two perspectives on this. One is that if you were the founder or the CEO or one of the folks creating the operations, How would you try to message this to people of like, you should choose this leadership path or management path versus this maybe potential, IC, individual contributor path. And then if you were one of those individual contributors at first, how would you think about that decision

[00:32:15] Jared Fliesler: I think the first thing is to understand people's capability and desire around these different areas. Let's break it into three groups. One is I just love doing the work as an individual contributor. Like, let's stay with engineers. So I love being an engineer. I love coding. That's what I wanna do. 

[00:32:34] The second is leadership. I love setting strategy design, thinking about the architecture, figuring out how we approach this problem. I maybe enjoy doing the work, but it's not a be on end all. I actually really love doing the design element of this and the leadership over it. Maybe I even like speaking to the team or giving direction or doing something else that's in this leadership bucket. 

[00:33:01] And then third is management. I love being responsible for coaching people. I love being responsible for helping people get to the next level. I love being responsible for helping people on their journey, right? And I'm okay with dealing with getting the bad apples out and setting culture and figuring out compensation strategy, and doing recruiting and being really externally facing. Now when I'm externally facing, I'm talking to people about joining our company and joining our team and being part of this thing versus the internal leadership model.

[00:33:32] I'm talking to people about how we handled image compression on the back end and how we're gonna render that on the front end, right? So these are these three different buckets that I might take as an engineer. And so I think as a leader or manager of that person, you wanna understand what is this person most excited about?

[00:33:50] And you have to know that the person who's never. done These other things, right? You're probably talking to a fairly junior new employee. So they've never done leadership and they've never done management, and so they're just hypothesizing about how that might feel, but maybe they've worked on a group project. Maybe. Maybe you give them the opportunity to do little bits of this and to get a taste for it. And then you check in with them and you see. 

[00:34:14] And so it's this idea of experimenting with them in their career and talking to them about what you're doing, but having a lot of awareness around it and then getting feedback from them on what are they like? Like what feels good to them, what's motivating them. think this also helps you long term with how do you retain that employee? How do you structure something towards their success. Do you feel like you're part of their career?

[00:34:35] And it's not just throwing money at them and bonuses and this and that. It's like understanding what gives them fulfillment. Where do they want help and how can you help them in those areas? So I would think about it in this way of like kind of dissecting and helping them understand which of these areas they might be good at and might make sense for them. If you zoom out and you think structurally, okay, well I'm the CEO of this company, how do I set up my teams?

[00:35:01] So that everyone has an opportunity to do the thing that they love and that feels most authentic to them. I really like this idea that you have really senior individuals who are doing their craft. And even though 15 years ago we, we might have called that the server engineering team, it has just taken new forms and still exists today.

[00:35:23] So, Chief Architects are often like this. CTOs are often like this. There's often some team of engineers that is just thought about as the really expensive, really capable, really talented, really elite engineering organization or team. And so I think that continues to exist today and that can exist in different functional areas as well. It doesn't need to be just engineering, but we're using that for our example. 

[00:35:51] So I would think about that as a leader. So you kind of, ideally you get the best of both the worlds that these people who wanna be on an IC path actually have a pathway go down, and that you're identifying who can be a leader, who can be a manager, and helping mentor and coach that person into it.

[00:36:06] So let's flip to the second question you have, which is, if it was me. If I were that person, how would I think about it for. I hopefully would've listened to this podcast or something else and would've gone, oh, maybe that's like a marginally helpful way for me to break down thinking about my future career path. And I dunno, I've never been a leader. I've never been a manager.

[00:36:27] I'd probably be asking proactively to my manager, how can I get experience doing that stuff? I wanna see how it feels, and I would test into that. Well, I know how it feels to be an engineer. I know how it feels to do this work. Like I'm really excited about. This is really fun. Hey, I'd love to work on a group project. Hey, I'm noticing in the group project that I feel really good about like rallying the troops and getting them all around a shared vision of what we do. This feels really good. 

[00:36:55] Hey, I'm noticing over time people are coming to me and asking me for assignments or for work on the group project, and I'm starting to feel a little bit like I'm managing them, like they're coming to me and asking me for feedback. Now they want external validation from. I actually really like the way this feels, or I'm really annoyed by that. I don't like the way that feels. Why are these people asking me these questions? This is a waste of my time.

[00:37:19] So, like these are natural things that you can sit in and you can experiment with in that position, and then you can zoom out and have that conversation with your manager who hopefully has awareness of this stuff as well. And you can just test into it, right? You're testing into what feels good to. And then leaning into those areas that feel really good. Hopefully with your manager helping you to succeed in the areas that are of interest, but maybe where you need a little help or a little guidance to get to be really good at it.

[00:37:46] Nima Gardideh: Yeah, that we, there is like a sentence in there. You mentioned that I couldn't stop smiling after you did because it just feels so Right. And the way I would put it is there is like a sense of, and people talk about this, that there are like, people are natural leaders. And really what they mean by that.

[00:38:05] And I, wish they actually wouldn't say that cuz there's, there is such a thing that you can learn to be a very good manager. No one's born a manager. But what they really mean is that they enjoy that part of the process where people come to them and ask them for feedback and they want to be part of this sort of like, feedback loop you can create with someone and think through their problems and their emotional blockers that might be there to help them become a better x. Right? Engineer, designer, marketer. 

[00:38:34] And I used to think that they, these leaders were sort of naturally emerged and I still believe in that to some extent because they'll just naturally come out of your org because people are like rallying around it and working with them. And so the tough part is I think what we've been talking about this whole time, which is there is like a narrative in everybody's mind. Put there by society, that success really means going up this ladder and becoming the manager. 

[00:39:10] And I want to go through this process again, but with, as a founder, cuz I think you go through like many more versions of this. When you start a company, at least in my experience, you're basically an individual contributor. You're working every day, producing, either code or designs or documents or whatever it is that you're working on. And then later on you have to go through these cycles of hiring someone then you've all of a sudden have to be a manager because it's not part of your new job. And then later on they are managers of people and then there's a whole new job and functions in all these different stages.

[00:39:45] I'd love to hear maybe at a high level first, what are the stages that you think people are gonna have founders have to go through that I think you helped them with now in your new So, let's go through that and then we can maybe double click on a couple of them.

[00:39:58] Jared Fliesler: So, The first stage is what I think about as tabletop management. And what this means is literally imagine a room that has a table and that you can manage the company around the table. Everyone fits around the table. Is the first key element of this. So there's a table, hopefully this isn't like, Allison In Wonderland or something where the table's going off into infinity.

[00:40:22] This is like, maybe a boardroom table or something like this. So generally that's sub 20 people are able to fit around this table. They're in a room and we're going around, you just have a good sense of what everyone is doing. Imagine that in that company, everyone works at that table full-time. 

[00:40:42] So this is literally, there's a big table in someone's living room or dining room or whatever it is, and everyone has their computer set up and they're managing. So maybe it's less than 20 people, maybe it's 10 people, and it's a little cramped and maybe somebody's sitting on the couch and, but you're also close to each other. You're shoulder to shoulder, that you just have like a good flow and a sense of what's going on in every department. Department at that point as an individual person. But that you have a good sense of what's going on because you're all in the same room. 

[00:41:11] And now you grow and you need two table. Well, now there's like conversations going on at your table if you've ever been to a dinner party. When the dinner party gets to. I've noticed that at like above eight people, it's really hard to have a single conversation.

[00:41:28] And what happens is two or three people sitting on this side get into their conversation. Two or three people sitting on this side get to theirs. People across the way get to theirs. And there's lots of little conversations going on over time. Sometimes they like blend and you get half the tables talking about one thing, half tables talking about another. But it's really hard to get the whole table because this person and this person, they're sitting five or six feet away from each other. It's kind of hard to hear what they're saying. 

[00:41:53] So at some point, when you get two tables, two conversations are going on in your. This conversation is about what you're doing in marketing and how you're acquiring your users, and this conversation is about your backend. And as the founder who's sitting in the middle, it's hard to pay attention to both of them. And so when you get from one table to two tables, it starts to get a little harder.

[00:42:14] The next phase is there's not enough room in the room for everyone. And so some people start to work in the room next door and the door's closed. Maybe the door is closed metaphorically, maybe the door is actually closed. Maybe there is no door. Who knows? But it's much harder to hear what's going on in that room. And if you think about a world where we're distributed and where people are working from home, they're working in lots of different little rooms and there's virtual rooms we're putting together. And so it becomes really difficult as we shift and move. 

[00:42:46] In a traditional office space, this happens when we go from one room to two, and then when you go to two floors, that's when it really breaks, right? And so typically, the numbers that I'm talking about here are when you go from about 10 people you experience a shift, I'm no longer just around this table with these folks.

[00:43:05] Then when you go around 50 people, you experience another big shift around a hundred, another big shift, and then around a few hundred, another big shift. And then as you get to thousands, bigger shifts happen. And basically everything you did to stay on top of things, break. Everything that used to work where it's like, Hey, yeah, we all just meet up Monday at 10:00 AM and we go around where we're getting coffee, we're all hanging out in the kitchen around the table, and we talk about what we're working on, what problems we're running into. When that's 50 people that doesn't work anymore. 

[00:43:35] And so I think you have to be really mindful of how do you evolve and change as a founder and how do your expectations and the tools you use and the systems you use to stay on top of things and to keep everyone else in loop with each other. How does that evolve as you grow in scale and there's just more things going on with more people at the same time. 

[00:43:56] Nima Gardideh: What I noticed through that was the underlying thing that you based your general model on was kind of information flow. And it felt like, yeah, there was like easy information flow at a table cuz you can just hear each other and everyone's kind of on the same page. And then the moment you're at a second table, it gets more complicated.

[00:44:17] The second room, the second floor, and then maybe second building or the second city, it gets even more and more complicated. How do you think about, so I, what I'm curious about and this is ike a little selfish, is let's talk about this like 52, maybe a hundred range. This about sort of where we're at as a company?

[00:44:38] And I think like a lot of companies we work with are about to sort of go through this first second barrier, here's what I'm noticing about that stage and let me know if that makes sense to, to have the conversation on top of, so at this stage there seems to be at least one management layer. There's maybe like one or two levels of hierarchy, just based on like, okay, well, as a founder I can no longer have 12 direct reports. That's too many. I want like maybe five. And then, so by the nature of that, you end up creating like, let's say one or two layers in the org.

[00:45:09] And then I no longer, and this is the one I think that was the most shocking to me at a personal level, was that I no longer have a sense of connection with everybody. Like, I don't know them and their life stories anymore as much as I used to. And it's actually hard for me to upkeep with their life stories. It's becoming very hard. There's not enough hours in the day. So my relationship also changes with these folks.

[00:45:35] There are two questions I have for you. One is like, how do you emotionally handle that shift? Like, what is it that you have to go through as a founder to think through that and not hurt the people that you started with? And they were like a huge part of creating this organization with you, but you just inherently have less time for them.

[00:45:51] And the second part is like, what is the new train that's coming that you should prep for that maybe even fundamentally changes even this state, which I think, like I've heard that people don't even know the names of some of the people that are working with them and all that sort of stuff. So, I'll leave it there cause that's kind of what I'm experiencing and pondering these days.

[00:46:12] Jared Fliesler: So I wish I could tell you that I have the silver bullet and the perfect answer to scale yourself and personal connection, both at work and also personally. Just how is it possible to meet an increasing number of people and socially stay in it with them and give them the same love and attention that you would to your closest friends?

[00:46:32] I think it's really hard, so I'll tell you sort of how I think about it for myself and for founders that I work with. I think it becomes hard. You're doing what you generally need to do to scale your company, and it's impossible to have the same closeness with these new people. You also don't have the same stories and the same history, and so I think it's hard both for those new people coming in who were not in the trenches with you and they don't remember what happened five years ago. You remember that time when the server went out and we did this, and it was heroic efforts, and we were at the office till two in the morning. Like, they don't, they weren't there, right? They don't have those stories. 

[00:47:12] And so you gotta figure out like, how do you make it a level playing field to the extent that it's possible in your human connections with these folks? So one thing you talked about, which is you make sure that you don't just keep adding direct reports because your ability to have a strong conversation and communication and even memory of what your team's doing is just limited. You can't do that if you've got 20 people to know what's going on in their personal lives and what's happening for them and to just remember all of that stuff and keep it straight.

[00:47:44] So I think keeping a limited number of direct reports so that your relationship with each of your direct reports can maintain and be very strong, I think is really important. I also think the expection of who you are as a founder with your team changes over time. And so when your team was 20 people and you were the founder slash class clown slash person buying rounds of drinks slash person doing this slash person doing that, that changes as you have a hundred, 200, 300 employees.

[00:48:18] And part of that is like the maturity of you as a founder and the maturity and the perception of you as the founder and leader. And I think that's not only okay, it's probably good. And so you have to own that, which is your new employee who comes in. Remember the first engineer you hired when you had no success and when your company was worth almost nothing.

[00:48:40] They thought you were a nice person. They thought you were smart, they thought you were capable, they wanted to follow you. They were interested in the idea of working with you. The person who comes in today and do your 200 person company that's worth half a billion dollars. Goes, oh my God, you're nema.

[00:48:58] You're the founder of this big successful company. You've done all these things, all these accolades, all these people wanna talk to you. All these people wanna work here. Wow. You're Nima and there's some distance potentially between you and that new employee. Their expectation is probably not that you're their best friend that's gonna go grab beers with them after a day of work at the office.

[00:49:20] And so you have to figure out like, what is your new relationship with this person? So there are tactics and tools that you can try in this. One is how do you figure out how to be a human and have people let in at scale? So whereas you used to potentially personally connect with people one on one by taking them out to lunch. Now you gotta figure out how do you connect with people personally at an all-hands or in a small event or at your holiday party or whatever it might be.

[00:49:50] You may also do some lower leverage one-on-one things. Maybe you go to coffee every once in a while with team members. Maybe you do what I call one over one-on ones, meaning one-on-ones with people that are a skip level, where there's somebody that works for you between you and them. Those could be 15 minutes, 20 minutes, 30 minutes. They make a huge impact on employees.

[00:50:09] So I used to every week do one or two, one over one on ones with people that were on my team's teams. And it might be just once a year as a touchpoint with me and that employee that actually matters to them. Now I have a sense of who they are, not just their name, but like what are they all about? What are they excited about in life? What's going on for them right now? and then I notice that if I have that context, Then when I'm in meetings and presentations and whatnot and I'm hearing this person, or I'm seeing this person, I have like a moment to check in or, I can see, oh, this is that thing showing up that they mentioned when we chatted.

[00:50:46] So I think it's a mix of just figuring out how to get really efficient with your time. And so you do these kind of bite size, one on one lower leverage, but really meaningful pieces and connections with employees. Then you figure out how to do more of a broadcast method. How do you drop into group meetings offsite, whatever it might be.

[00:51:04] Maybe there's a team of 20 people and maybe you're meeting with all of them. Maybe you're joining a. That one of your functions or team's having, maybe you are at an offsite doing a fireside chat and you make it personal and you talk about your personal life and you really connect with a hundred employees all at once, where they really get to know you.

[00:51:23] So it's all about like finding these mechanisms that scale as your teams and companies get larger, but I think them continuing to understand who you are and how you are is really important. Otherwise, you become this like, nonhuman CEO that they don't necessarily feel connected to. And then you're really banking on the fact that they just love the company, whatever the company is doing. And I, I think generally really good founders, they stand for something and people, some people follow the founder and the company stands for something and some people follow the company or some people follow the company of the two.

[00:51:58] Nima Gardideh: Yeah, that I was gonna ask you about identification a little bit here, where people like, identify with the company's mission or the goal, or sometimes with the founders or sort of with the community of it at large. And that all resonates with me a lot, that the mechanism I use, and 

[00:52:16] I'd love to hear your thoughts about the different form factors is the way, maybe I would put it, of attempting to humanize yourself and like let people know that, hey, you're a person just like everyone else working on this thing with them and trying to grow it and create flourishing potential for everyone.

[00:52:36] I write a weekly essay right now. It's been now three years I've been writing one every week to the whole company. And I find that, and the reason I started is because it was originally a ritual for myself to like look inward and think about the company. And now it's become much more of a tool to think through problems with everyone in the company.

[00:52:58] And they can sort of direct message me afterwards and talk to me about the topic that I've written about. And my co-founders, or even now VPs or directors will come to me and say, Hey, can we write about this in the weekly policies, what I call it? And it's, I found it to be a useful tool. It has its limitation cuz it's text and now I'm recording myself, but it's an interesting problem space. 

[00:53:20] What are the mechanisms you've seen that solve for what you just talked about? Right? What, and I think you, you brought up a few already and there were micro ones, of like a dropping it into a dinner or having a personal anecdote or conversation with a larger group of people.

[00:53:43] Do you feel like there are things that are just standard everyone should do? Is it based on your personality? Is it based on the type of culture you want to build? Like, what are the vectors there and how do you suggest people do it? And how do you personally think about it when you've run teams before?

[00:54:01] Jared Fliesler: So, yeah, I think there are some things that are standard, which are, for example, like the most standard ones are that you're building that personal relationship with your team. So most leaders would have leadership team meetings. They would've one-on-ones and that some portion of that time is spent, sort of connecting outside of just a tactical update or functional update. 

[00:54:24] This is a little bit more nuanced. It's not to say that like, Hey, you should spend 43% of your time in these meetings doing personal round robin updates. It's a hey, if you realize that like what's going on in people's lives is pretty important. Maybe you wanna figure out how to dedicate the first five minutes of your leadership team to going around and checking in, or maybe it's casual chit chat before you get going, or maybe you do a lunch every two weeks as a leadership team meeting. where it's not all tactical and about work. Or maybe you make every third one-on-one you have with your direct report developmental, and part of that is like checking in and seeing what's going on for them.

[00:55:05] And what's funny is like when I talk to people, especially when I talk to clients, I am not a Kumbaya camp counselor. I am not here to try to make sure everyone is super happy and blah, blah, blah. Like it's work. You get paid for a reason. we get paid for a reason, right? And that said, we are humans and we experience emotions.

[00:55:25] If we can completely ignore the fact that people have emotions and are going through things in their lives, they will not be able to do that, right? So like we can ignore it as their leader. We can even say, Hey, there's no place for that in the workplace. Potentially. Some people have decided to do that, but the reality is like they're still living their lives.

[00:55:44] They're still dealing with the fact that they're going through a divorce or that they just had a. or that they're feeling unsettled about the election or whatever it is. And I think it's trying to figure out how do you exist as a human in that space cuz they are human and how do you show up and have awareness of that while not allowing that to take over. Your work, right? That's not why they're at their job. That's not really what the purpose of work is. It's not a therapy session, it's not a counseling session, but they are human and you are human. And so if you want to know what's going on for them, if you need to know that, like, Hey, somebody in their family just died, maybe it's not the best time to give them a bunch of critical feedback.

[00:56:29] Maybe next week is a better time to do that. And if you don't know that, and you give them a bunch of critical feedback, And they quit because they're in an emotional state where they can't handle it and receive it, then that's on you. You gotta deal with the repercussions of it. I by no means am saying that, well then you've gotta coddle your employees and you've gotta care about every single little thing that's going on in their lives. But it helps you to have that information. Then you get to decide how you're gonna behave, how you're gonna behave differently. 

[00:56:55] You may even say, Hey, I'm really sorry that this person just passed away in your family. This is terrible timing for me to. Feedback with you, but I feel like I need to share negative feedback with you. Is there a way that you can be available for that? Like at least you have awareness around it, right? And they feel at least seen and understood and heard and they can receive it. So like I think it's actually really important to figure out how you show up as a human. How you do that is unique to you. It's gotta be authentic, it's gotta be organic for.

[00:57:25] I would generally check in with my direct team members. If I was really rushed and we had a 30 minute one on one that was gonna be highly tactical, I might even say, Hey, I know it's really rushed this week and we only have 30 minutes. This is gonna be tactical and an update.

[00:57:38] Next week, we have an hour. Let's make sure that we spend the first 10, 15 minutes, like checking in and just seeing how things are going overall, right. I would often make about once a month, I would make my one-on-ones when we were in the office, walk-in talks or coffees, that kind of forced them to be more casual and to be like, Hey, what's going on for you?

[00:57:58] And oftentimes what would come up there is somebody would be like, they would've never mentioned to me before, and they'd be like, oh, I just had the worst meeting with this person, or this person's such a pain in my ass and they're so hard to work with and they're this, that, and the other. Like, you know, to be honest, I've been really struggling. My husband is changing roles and he's kind of talked about maybe we need to move and I don't know how I feel about that. Like these little things would come up that were really useful to me as a manager. Oh, shit, I've got this executive team member who has a partner who is kind of pushing them to move to the other coast. Like that's a good thing for me to know and to be factoring in and to be showing up around. So I think it's unique to you and how you do that in your conversations. 

[00:58:41] I think a big one that's also universally available is how you show up in all hands how often. Do you come in and how does your team receive you?Where like, when do they get a glimpse of who you are at your all hands or at your events or whatever it might be? Office hours are another easy way to do this. You just make yourself available. Oftentimes that's just like kind of a casual chat with employees and maybe that's once a quarter, like it doesn't need to be that often, but just being available as a founder or as a CEO and being able to talk about what's going on in your life and what's going in theirs, I think that humanizes you and allows you to connect with more people. 

[00:59:23] And then I would say the in-office one, and I don't know to what extent this has made its way into the virtual world, is that there used to be lots of like after work activities and things that people would do. They might go to drinks or go out to dinner, or there might be a game night or things like this and that You would often see leaders engaging those things. So like poker, poker was big at a bunch of companies and you would see like executive team members playing poker. Entry level employees that are coming in and now there's this new bond form through something totally unrelated to work.

[00:59:56] And I think that's one of the hard things that it's not clear to me that those things have made their way into a virtual environment in a successful format. And I think as a result, we miss out because we don't have this other humanizing, like equal playing field where we can connect and build these points. And instead, we default to this kind of like pyramid or hierarchy.

[01:00:20] Nima Gardideh: Yeah, that part of remote work. And for context, Pearmill, the company I help run is out of like 12 countries or 13 countries or something like that. And we've always been remote. And I used to play ping pong with the CEO of a company I used to work at. And I was like, many levels disconnected from this person, but I felt like I could always go to him and ask questions because literally, because he was playing ping pong with me and I think I was like 22 at the time.

[01:00:54] And so there, there is definitely, I've personally experienced this and I think it is part of remote company building that is very hard to solve for. There's plenty we can talk about there. We have our own versions of it. We do have game time and we have like virtual tees and all this sort of stuff.

[01:01:13] And then we bring people together a couple times a year. But there's definitely some of that. Relationship building that's beyond, Hey, let's have a structured time to have a conversation that just is harder to do when you're remote. But I think I get the general point very well in that a lot of it seems to be personal about how you'd show up as a human, how you

[01:01:42] really experience your yourself, and then project that to others, and able to recognize that they may be also going through a tough time or a hard time whenever you're giving them feedback or going through these moments where you have to both empathize but also recognize that you're part of a community trying to build something or create an experience for the rest of your colleagues.

[01:02:06] Jared Fliesler: I was just to say one thing that I think is like a, at least a guiding light for me in this, especially when you get into the, like, how do I manage emotions versus outcomes and my business overall is if you can align around the outcomes you're trying to achieve, I do think that's the best thing for you to have alignment with on your team.

[01:02:28] And so, when you get into a place where your team goes, oh, well, I'm just having a hard time because all of this stuff is going on, and you go, oh yeah, I totally understand that. Me too, and our numbers are down, and we're the only people that can do something about that. Right? And so this is the place where I think you have to shift the conversation.

[01:02:50] I've always found it, it's really hard when you're the founder, you're on the leadership team, you're running a company, your revenue is down, and Bitcoin is down And you're a Bitcoin investor. Both of those things are true, and maybe you're freaking out that half of your wealth is in Bitcoin and that the price just dropped, and maybe your team is freaking out because half of their wealth is in Bitcoin and the price just dropped.

[01:03:14] But the reality is you still have a company to run and the value of your company, the only people that I can make that go up is you. And so it's almost like banding together and being like, Hey, this thing is happening. I'm aware of. it I, know this is happening. Let me call it. out And that does not give us license to stop caring about this other thing.

[01:03:35] In fact, let's say that goes to zero, we better give a damn about what happens to the value of our company because that's the other side of our wealth, right? And so it's this weird thing where I've noticed sometimes when things are going on and people are like, oh, it's just too much and there's all this stuff going on.

[01:03:49] Let me just, I should get a free day. I should be able to walk away from what's happening at the company and somebody else should take that on. Cause I'm stressed out and other things are happening. It's like sometimes that can happen. And other times it just is an extra weight that we have to collectively carry because we are responsible as owners of these companies to make them successful.

[01:04:13] And so it's this hard reality of sitting in that and like, how do you show up with empathy and awareness and the reality that you have to manage that. And so if you can get everybody towards outcomes and become less dogmatic about the path to get. there Like, Hey, I get it. This is annoying. This is gonna blow up my weekend. This means I have to cancel date night. This means I have to do this other thing. Yep, I've gotta do that. Here's the outcome I want and that's gonna require this thing, this cost, but it gets me this outcome.

[01:04:43] So even though I don't like the way that I'm gonna have to get there, the reality is I've already spent the time and energy thinking about it. This is the way to get there and it is worth the cost. I'm gonna stop complaining about the process of getting there because the outcome we're aligned on. And I think there's not enough of that and, that's something that we have to constantly push to do. 

[01:05:03] And as founders, when you make tough calls killing product lines, laying off employees, hiring new people, raising more money, these are the kinds of calls you have to make where you go like, Hey, I also don't love this thing that we have to do, this hard decision that we have to make. And if you can have the empathy and awareness to communicate about that and to talk about why you're doing it and the outcome you're trying to achieve, if people are then aligned around the outcome, that's where I see a lot of success, where people are like, okay, cool. Yeah, this is shitty and we're doing this thing that none of us want to be doing, but the reason we're doing it is to get to this outcome that we're aligned on. Great. Then let's go do 

[01:05:40] Nima Gardideh: it.

[01:05:41] Yeah, and I really like this perspective of like a more of a nuanced approach of like, hey, there's, this is the outcome that we want. These are the goals, but here's the context behind why we think this is important, plus that the recognition that this sucks right now because all these other stuff are going on.

[01:05:56] I think that part always missed for me in a lot of orgs that I have been a part of as a sort of a younger person not being part of the founding team of things where recognize that it's hard, tell people that it's a very hard week or a hard month, or maybe it's gonna be a hard year because of X, Y, and Z, and some of which are in your control, some which are not.

[01:06:22] And the sort of metaphor I've been using with our team, and you know, for context, this is a year where capital markets have shifted and, we are highly. Indexed on it in some ways cuz we work with venture back companies and so they are, ultimately connected to capital markets. I've been trying to get this metaphor out around that you are the drive you are in the driver driving seat of the car to a large degree.

[01:06:53] As especially in our business the impact of an individual to the outcomes of our business are still very high. And so, I've been talking about that we're all in this car together, but it turns out that we're all to some extent in the driving seat, driver's seat. And, we can make impact and change the direction of the company.

[01:07:12] And fortunately it's worked, but we had a very hard summer and these concepts you talk about are very Close to me right now. Cause we've gone through a similar experience of having to align everyone around these goals. Even though the experience has been hard to go through for both at the individual level of, we, we have folks across the world going through turmoil because we have Ukrainians and Russians and folks in the eastern parts of Europe all the way to just the reality of politics in America.

[01:07:42] So it's been an interesting sort of year to, kind of think about these two sometimes, or like in the past may have been thought of as opposing aspects of human nature, logic, and emotions. But in my opinion, they're pretty much intertwined and sort of have to align them in order to get good work done, both as an individual and as an organization.

[01:08:08] What some of the things that we talked about having to come from founders versus if you are just leading a small team, you can sort of instill some of this culture that we talked about earlier.

[01:08:20] Do you feel like you need to tap into the cultural apparatus of the company and sort of follow it as a, a, a middle manager or a director or vp? Or do you feel like you can make change, um, and lead the team in the way that you see fit, um, in an organization like that?

[01:08:38] Jared Fliesler: uh, I mean, I think company culture can be really valuable and it can go in either direction. So like the culture can really help you as a founder in guiding your company, managing your company, leading it in a consistent way, and getting the kinds of outcomes, retention and whatnot that you want, and it can work against you.

[01:08:57] It's in lots of companies where the culture. Sort of, jumps the tank, and suddenly the people leading the company no longer feel like they can shape the culture. Cultural values are often turned around and used against companies or company or executives, especially in an increasingly robust startup economy.

[01:09:20] Maybe it's better now as we see layoffs and a little bit less entitlement. But in an environment where we had so many people having choice, it really, the power balance shifted from VCs to founders, to employees, where employees are like, well, hey, I think we should be doing X, Y, and Z.

[01:09:41] And then you started to have groups that would rise up and activist groups within private companies saying like, well, we should do this and I believe we should do that, and here's the people we should serve and here's where we should put our money and here's causes we should support. And that becomes really hard if you don't have a consistent culture that's clear that you've continued to keep your hands on the reigns of, then it's really difficult to jump. And not expect that culture has been forming, right?

[01:10:12] Like culture is going to exist. You have human beings with emotions and they are going to feel a certain way. And so I think you need to be part of that conversation and guiding that cause it is your company and you do get to decide what direction you go in.

[01:10:26] If you're silent to that or quiet to that, you're gonna bring people in that silently or not so silently have their own viewpoints. And once those people are in your company for an extended period of time because they've continued in your company and you haven't said No, this isn't what we stand for. Like, sorry, I don't think this is a good fit now their louder voices around your culture than your own are setting company. 

[01:10:54] Now they are saying to the people they hire because culture is important to them, they're recruiting other people that have a shared belief system with what they believe. And they are saying to people at lunch and on Slack and in their groups and at their game nights and wherever it is, they're saying, well, this is what I stand for. This is what we should stand for. This is what's right. 

[01:11:15] And the idea gets introduced that the company should do or feel or be or act or contribute in a certain. And you are not leading that conversation as the founder, you are now subject to that conversation. You are hearing that conversation. You're being told what your company should do, and so I think that's something you have to be really mindful of.

[01:11:38] I actually think it's better for everyone if you're really thoughtful and clear about what you stand for and what the company as an extension of you stands for and the culture and what you will do and what you won't do, and that's not a question that is a statement of, here's who we are, this is what we stand for, this is how we're gonna shop. Then you're going to recruit other people that feel consistent with that.

[01:12:02] And while you may lose some people at the front door who go, well wait a minute, I think we should be doing X, Y, and Z. Why don't you believe that? And you go, I'm sorry you feel that way. We've thought about it. We're not going to do that. If that's a deal breaker for you, please don't join our company. It's not changing. Right. 

[01:12:19] And if you have the strength to do that upfront, I think it saves you a lot down the road and it's honestly just better for them and better for you. They wanna join a company in a culture that behaves in a certain way, and you wanna have a company in a culture that behaves in a certain way. And I think too many people are silent to this or like, oh yeah, but we need to fill this role. Oh, but it doesn't really matter. You're introducing a very, very different mentality and culture underneath the surface into your company that you do not have control over. That you do not know how loud it's going to be, that you do not know what the full impact of it will be.

[01:12:58] And so while I think it's possible to just like jump in as the founder and be like, well, we are going to do X, if you do that without the culture, you have reverberations. So let's use a really good example. Elon just came into Twitter and without really being involved in the culture, said we are gonna do things in a different way. As the founder, he has the power. Well, not founder as the owner he has the power to say, we are going to do X to dictate it. That has cultural ramifications and in his case, maybe he's okay with that. Maybe he is like, Hey, the people that don't agree with me, Maybe they should go, but he's very good at saying, this is what we will do. This is not a discussion, this is not a compromise. I am telling you what we will do.

[01:13:47] So it is possible that you can lead in that way. It is probably less disruptive to be consistent and saying, Hey, this is what we believe in setting that culture. And even if you set the culture and you have to come in and say, Hey, I really believe we should do this thing we're going to do this.

[01:14:04] The closer that your culture is to this, being consistent with that culture, that set of values, the less turmoil you're gonna have, the fewer people you're gonna have quit and whatever it might be. Not cuz it's bad to have people quit, it's fine to have people quit, but just because if you've been sending the culture the whole time and it's consistent with your ideology around how you're gonna make decisions, that's generally going to result in a better, more fruitful company than if aren't setting the culture and you're just coming in and people have no idea how to relate to those ideas. 

[01:14:35] So I think these things are really tightly coupled and ideally you really think about what you stand for or what you and your co-founder or you and your co-founder and your leadership team stand for, and you write it down and you're really clear about it and you have the strength to stand up for it and when people say, Hey, I don't agree with that, either you feel like it's a conversation and you are going to modify it or you say, this isn't a conversation or a discussion where we're gonna modify it. This is what we stand for. Take it or leave it. But you decide that upfront. Kind of like non emotionally, not in a moment where you're reacting to a situation in the world.

[01:15:10] And then people know what to expect when there is something that's heightened, that comes up when the site goes down, when users feel taken advantage of when something's going on in the world and you don't respond or you do respond in a specific way, then people go, well, of course we responded in this way. Of course we did that thing that's consistent with the cultural values that have been set.

[01:15:28] Nima Gardideh: Yeah. And this feels like very familiar in that it, the best cultures feel extremely cohesive because everyone feels aligned and feels like they also represent it. And mostly it's been done through hiring for that, sort of definition or the type of culture or community you wanted to be creating inside of the company.

[01:15:51] We'll, stop here. I feel like we can spend a couple more hours just going through these different topics together. Jared, thank you so much. I feel so grateful for your knowledge and wisdom. And I think it should be on the record that before we had this conversation, Jared was very adamant about knowing that we're going to provide some value to the listeners. So, I hope this was a useful conversation for everyone. And thank you again, Jared. Thanks for coming.

[01:16:18] Jared Fliesler: Yeah. Thanks so much for having me. It's been my pleasure.

[01:16:20] Nima Gardideh: Awesome.

[01:16:21] Jared Fliesler: Good chatting with you.

[01:16:22] Me too. And that's a wrap. Another one with Jared. This time it was a huge learning experience. Experience for me just to listen to him talk about these different topics. These are, I would say skills or theories and things in my head that we're just learning about as we've scaled up her itself and the company that I work on with my co-founders.

[01:16:47] It's been a wonderful experience there, but also, I recognized how hard it is to even have some of these conversations. Grateful for Jared came with all this experience and as, and was able to shed some light on some of the different paths you can take as a founder and as a manager.

[01:17:06] Thank you so much for listening. This is the last episode of the year for us, one of the last episodes of the year for us. We got another one coming next week with Vikas Hebbar who's the growth marketing VP at Tia. And I assume you probably know about that one. That's a big company, is raise a lot of money, so it's gonna be an interesting one.

[01:17:25] And he has a very extensive background and growth and market. In general. And as always, if you could, smash that subscribe button or leave us a review, I would be forever grateful. Thank you so much. Have a good one.