From Intensity to Empathy: Grammarly's Head of Growth's Turning Point

I was known as the intense guy. Like, oh, Yuriy, he's intense. That wasn't meant as a compliment. I was under a lot of stress and pressure at Grammarly. It was because we had really audacious goals, but I suspect it was largely because of the pressure I put on myself. And I felt like I just couldn't spare any time for anything that I didn't feel was absolutely essential to completing our goals.

Hey, welcome to the show. I am your host, Andrew Kaplan, and this is a show where I chat with people who I look up to, some of my SaaS heroes, people who work in and around growth teams to hear about their journeys, how they even got into this space, and explore some of the toughest moments they've encountered along the way in their stories. My guest today is Yuriy Timen. Yuriy's the real deal. For the past 4 years, Yuriy has been advising a variety of SaaS companies that you know of and probably look up to: Canva, Airtable, Otter, Crisp, and a whole bunch of others that you can see on his website, yuriytimen.com, Or in his LinkedIn profile. And before working as an advisor and as a solopreneur, Yuriy spent 8 and a half years leading growth and marketing at Grammarly. Yuriy shared his story and his upbringing and his family's background in entrepreneurship, how that influenced his career getting started in the finance world and some of the data and financial modeling work that he did. And then eventually getting into his role at Grammarly where he was there for 8 and a half years and made a whole bunch of mistakes along the way. As a high-powered IC transitioning into a leadership role at a fast-growing tech company. Yuriy and I touched on a ton of stuff along the way. We had a lot of fun as well. He is fun and entertaining and charismatic. You're gonna love this episode. Let's go ahead and jump right in. You're 4 years into your solopreneur journey, so I saw that you left Grammarly May of 2020. I know you stayed on as an advisor for a little bit. 4 years of the journey. Do you see yourself ever going back at this point? I know you mostly advise.

Yeah.

Do you see yourself ever going back to in-house?

More likely than not that I will go back, whether I join an existing company or I found something. For me, it comes down to wanting to build again and wanting to be in the trenches again and wanting to have a lot of skin in the game again. Now, Don't get me wrong, if I've been doing what I've been doing now for 4 years, something is working and it's definitely scratching some other itches, right? And I've been erring on the side of continuing in my current rhythm, this sort of like solopreneurship journey, right? Where you have your hand in multiple cookie jars. And it does give me the opportunity to explore and dabble and the variety has been were really, really exciting. But if I think about if there's anything that's missing from my current rhythm of work, I like to say that the lows don't feel as low as they do when you're an operator, but also the highs are not as high. And I miss those highs sometimes. Like if I score a win as an advisor, as a fractional growth person, or the team I'm helping scores a win and everybody's celebrating and I'm celebrating with them, and then I'll catch myself and be like, This doesn't feel the same. I'm happy for them, but I can't take as much pride in this win as I was able to do at Grammarly as an operator. And that feeling, I tell myself, I'm going to want to tap into that again. It may not be tomorrow, it may not be a year from now, but I'm 38. And to think that I will never tap into that feeling again, that's a little bit of a depressing thought. That's what tells me that I will go back to building at some point. But I have no timeline on it.

Still have that itch?

Yeah. Intermittent.

Intermittent itch. Because I was listening to your podcast with Lenny, and in it, I don't know if you're still doing this, but in it you shared, I'm working 3 to 3.5 days per week. I'm working with 4 to 5 clients at a time. I imagine you're probably making more doing this than you were when you were in-house. And I was like, man, if anybody gets to that point, why would you ever go back? And it's because you got the itch, which I get.

First of all, even though I've been I'm extremely fortunate, to your point, to get to where I have the pipeline and I can be selective in who I work with. Maybe this is where the imposter syndrome comes in, which we're all prone to, to some extent. I have no expectation that it'll last. I don't know to what extent I played a role in getting it to this point. It would be a little bit too conceited for me to think that I know how to keep it going indefinitely. So there may come a time where circumstances change. Maybe I fail to keep up. Maybe the market crashes harder than it did before. So there are a number of variables that could tip the scale in favor of me, like, hey, you know what, let's take another swing at it.

It's somewhat refreshing to hear you say that because I think it would be easy for someone to look at your pedigree and your background and all the impressive companies that you've helped as an advisor in addition to your in-house Grammarly experience, And think, geez, he's got it all figured out. He's got the answers. He never needs to worry about the things that I worry about. I'm just little old me. And so I think it's really refreshing to hear you say, hey, I don't think that ever goes away. In fact, that might actually be the thing that helped me to accomplish some of those things is I had that chip on my shoulder.

Yeah. As you get more senior or accomplished in your career, it's not that you grow out of the imposter syndrome. But you learn to wrestle with it and probably use it to your advantage at some point, right? It becomes a more familiar feeling and you can use it to your advantage. I'm not a surfer, but for some reason a surfing analogy comes into play. Like when you're starting out, the waves are overwhelming, right? They are engulfing you. The wave here representing imposter syndrome. As you get more practice, as you get more hours under your belt, It's not that the waves get smaller, and it's not that the waves cease to be as potentially dangerous. It's that you learn to ride that wave and you ride it toward your goals. You ride it toward success. But a good surfer never lets their guard down, I would imagine, because you understand that you don't fuck with nature.

I used to surf a little bit, and I still identify as a surfer, so that makes sense to me, right? As a beginner surfer, everything is overwhelming. And as you spend more time in the water, you learn, hey, this is just what it's like when you're in the ocean. It feels this way. It's kind of a normal feeling. You never feel in control. You just get used to feeling out of control and knowing if I do wipe out or I end up getting sucked under, eventually I'm going to pop back up. So that, that resonates with me. I'm curious to know a little bit about how you got here. So can you take us back in time a little bit? Can you tell us where you're from and what your childhood was like?

Yeah, absolutely. So I was born in a country that no longer exists. But still gets talked about quite often. And that country was called the Soviet Union or the USSR. I was born in what's present-day Ukraine, but at the time it was the Soviet Union. And I was born in '85 and the Soviet Union collapsed in '91. And so I was coming of age and I lived there till, well, in the Soviet Union, then in Ukraine till '96. And so I think it's an important piece of background because I was basically coming of age While Soviet Union collapsed, there was private markets flooding the former Soviet republics, and my family took advantage of that and was very enterprising, if you will. And so I definitely come from a family that is entrepreneurial and enterprising in nature. And the way I would categorize my childhood, honestly, and I've been thinking a lot about this, especially since I became a parent, is we hear a lot about privilege nowadays, and I think privilege is very relative. So the way I grew up, I'm sure that there were people who would look at me and consider me to be privileged, but in the same vein, there were a lot of people that I could look up to and see privilege in their upbringing. I feel like the way I grew up and somewhat its objective family means, and some of it is the way my parents architected my upbringing. I felt like there was this perfect balance where I had enough of a foundation, I had enough of a support, including financial, to where it gave me a launching pad that many others did not have to go and compete. But at the same time, I knew from a very young age what it meant to earn a living. Like my parents, I don't know if this was intentional, but when I look back, I would say they always made sure that I was brought up slightly below their means. Conventional wisdom is like parents trying to give their kids everything so that they grow up with more than the parents had. And I still probably had more than my parents had, but I remember all these little anecdotes from my childhood where my parents could afford something, but they made it a point to withhold that from me or Delay that gratification. I have a lot of anecdotes to my childhood that I remember being honestly resenting my parents in the moment, right? Why does so-and-so have that and I don't? And then in retrospect, honestly, I think it was brilliant. I started working like 13. This is already in the United States. I was working 13. I was selling t-shirts at Fisherman's Wharf in San Francisco. I was working at the Rainforest Cafe, which is kind of an iconic cafe, starting at 15. in San Francisco, and I didn't have to. My family didn't need that support. So a lot of other families in my parents' situation may have said, hey, you just go do well at school, take care of that. But that wasn't the case.

I asked this question on purpose because, well, one, I'm curious how someone like you gets to the position that you're at. And two, I think there's a lot of people who probably look up to people like you and the other people who are at your level of experience and your pedigree and think it must have been easy for them. And so I want to share these stories to show everyone comes from a different path, and there are things that make us all similar, and there are things that make us all unique, and to share your story. So you mentioned that your parents were entrepreneurial. What comes to mind as you share that? What's an example so that we can kind of picture the same thing you're picturing?

My dad, the kind of businesses he was spinning up in Ukraine when capitalism flooded the ecosystem there, there was a lot of importing because the Soviet Union was so closed off. Everything was like homemade. So my dad started importing Adidas sportswear from Germany. He was importing Häagen-Dazs ice cream. Then he opened up a beach cafe with water slides. Then he went into an optics business, opened up the equivalent of a Sunglass Hut. A lot of these little hustles, some of them medium-sized hustles, but because this was a country and a people that didn't have access to most Western goods. They were hungry for that. He also opened up like a jeans, like he was making jeans and he was making leather jackets and all this other manufacturing things. Yeah. So he was all over the place.

And you also mentioned that growing up, there were things they could have provided for you, but instead they taught you how to go provide for yourself. What's something in your head that you're picturing that you're like, man, I wish they would have just bought that for me in the moment, but I had to go out and work at the Rainforest Cafe and save up.

Jordans. My parents never bought me Jordans.

Hell yeah.

They're like, they're just sneakers. Why do I need to pay $180? Here are Nikes from Ross that are $40. I don't see a difference between them, was what my parents would say.

That's hilarious. As you were telling that story, I was reflecting on my own childhood and my parents did this with me where I remember wanting a Game Boy. I grew up in '85, so I know you grew up with Game Boys too, and everybody in my neighborhood had a Game Boy. And my parents were like, look, if you want a Game Boy, you got to save up and do your chores. And so I did all these chores, you know, I'd get like a couple bucks here, a couple bucks there. And like 16 months later, I bought myself a Game Boy. And so it's cool hearing you tell that story. It's like making me reflect on my own life a little bit. Okay. So you go from working at the Rainforest Cafe, working little jobs here and there. Like what's the first couple steps you took to get into the tech world? PLG, SaaS, marketing. How'd you get from there to there?

Well, certainly not straight from the Rainforest Cafe. I figured. I mean, it's a great platform, but to connect those dots, there is a lot that happens in between. Eventually, along the way, I start getting my shit together. But I guess that implies that I didn't have it at some point, which is true. I definitely had some rough patches growing up. And actually, I get my shit together. I get into a good school, UC Berkeley. I double major in business administration, economics. I have good grades. And as I'm coming out of it, frankly, it was a bit of a feeder school and feeder majors for a few career paths, all of them kind of in finance. So there was like management consulting, investment banking, corporate finance, accounting. This is 2007. So unless you're an engineer, unless you studied computer science, Startup jobs are kind of unknown/unavailable to you. It's important to recognize that because folks graduating even 7, 8 years later after me in a similar situation, they had a completely different additional career track available to them. They could start a marketing career at a startup, but at that time I was completely unaware of that possibility. Companies were not at our job fairs looking for entry-level marketing managers. You know what I mean? So I had to choose between those available career paths, or so I felt. And I ended up landing a job at Merrill Lynch in their investment banking group. And I did that for about a year, a little over a year. I was pretty miserable. I felt like I was just in the back office building models, et cetera. Huge bank. The first year was just go through the training programs and stuff like that. And so I'm like, okay, I'm unhappy, but I'm still clinging to finance. Like, I think that, hey, maybe I just need a smaller environment. Maybe I just need a smaller thing. So I end up swinging the pendulum in the other direction completely and joining like a startup private equity fund where it's just 3 partners and they need someone to do everything. And I became that everything. So 3 partners, all of them come from big banks. They decided to start something on their own. It was a fund called Blue Horizon Equity. It was investing in companies in the health and sustainability space. It wasn't like hypergrowth investments. It was like growth equity investments. Spent about a year there and I realized that, hey, the smaller bank corrected for some things, but there are also just some things that were endemic to finance that I just felt like Didn't sit that well with me. I'll give you a couple of details because I think it'll inform why I made the pivot and where I ended up later. So number one, I felt like finance was an industry that was deeply steeped in tradition. That meant that your career path was in many ways pre-charted for you. Like you could fail and not make it to the next step, But assuming that you did well enough, you were just going to step up on that next rung of the ladder and then meet expectations there and step up again. There was no opportunity to make a leap if, let's say, you were outstanding. And also there was no opportunity to just take a complete, like a more circuitous path.

Were you not motivated by that environment?

I wasn't motivated by that environment.

Especially with the family and your dad with all these businesses, I would imagine that that Seems really boring in retrospect.

Yeah. I like to think of myself that generation on the cusp of like, a job is just a job, or like, wait, I can contend for more. I can actually work on something that I'm passionate about. I consider myself to be on the cusp of that because I feel like the generation that come after me— I have a sister who's 12 years younger, and she also was graduating UC Berkeley just 12 years later. Completely different mindset. Like, I'm going to look for something I can be passionate about, that I can actually marry passion with livelihood, making a living. And I was more of that generation, like, a job is a job. You want to be passionate about things, get a hobby, right? And I started questioning that in the midst of my finance career when the market crashed in '08. At that point, I was about 2 years into my finance career. It felt scary and devastating. I ended up without a job, but I took an offer that was then rescinded. And so I ended up without a job. All I knew how to do was finance. It was scary. Actually, I don't remember how long. It felt like an eternity, but it was probably like 3, 4 months, a period of when I was like completely lost because it was really hard to get a job in finance. You had all these big banks that went under and there were like more experienced finance professionals that were flooding the talent market, willing to take jobs below their career level. And there was me with 2 years of finance experience, kind of like, oh, hire me. So I was like at a huge disadvantage. And it ended up being a blessing in disguise because I said, hey, maybe now's the time to take a look outside of finance. It's not something that I'm passionate about anyway. And so I ended up broadening my job search. I'll be very honest, I broadened my job. I was still applying for finance, business analyst roles. I was like all over the place. And one of the applications I put in was at a digital marketing agency. It was called Leapqual at the time. I was interviewed aggressively and I walk into their office. It was in the East Bay, San Francisco Bay Area. I walk into their office and it's a bunch of people wearing t-shirts. And I came from a place where every Saturday or every Friday afternoon, I would take my dress shirts to the dry cleaners, pick them up Sunday afternoon for the week. You know what I mean?

What were you wearing to the interview? Sorry to interrupt you here. Were you wearing like a suit to the interview? Did you feel overdressed?

I 100% overdressed.

Yeah,

100% overdressed. I don't remember if I was wearing a suit, but I was probably wearing like a shirt and a tie. I was a complete tool. And they're wearing t-shirts. They seem to be my age, give or take. It was a casual setting, open floor plan, right? Open seating floor plan. Shit that was completely foreign to me. At that point, I've seen enough. The fact that I saw that somebody who's maybe 2 years older than me was managing a team. Why? Not because they climbed some predetermined career ladder. No, because they demonstrated some innate talent skills that aligned with the needs of the agency. And so they popped into that role. That together with not wearing a suit to work, I'm like, sign me up. I got that offer. It was probably like half of what I was making in finance, to be very frank, but I was in my element. It was fantastic. Immediately I was able to really leverage my strengths because in finance, it's like when you're early on in finance, you're just cranking out models. And I was quant enough, but I wasn't like in the top 10% of building financial models. When I feel like I was in the top 10% or maybe even 1%, if I'm kind to myself, is marrying the quant with the relationship building, with translating data into insights and then relaying those insights to the client. That was when I felt like I was really hitting my stride and this agency allowed me to do that. That was the beginning of the pivot though.

Yeah. No. So it's really cool. So you started in finance, you cut your teeth in financial modeling, which is super helpful in this second act, right? As you start to get in and probably your skillset that you were okay at in finance, you probably were top 1% in this new arena working at the agency. How long were you at the agency for?

It was also short. It was maybe a year and a half, and then I ended up going in-house and that was like a Thoughtful process. It wasn't random, but yeah, about a year and a half at the agency.

And then did you jump from the agency straight to Grammarly?

No, no. So from the agency, I jumped to another Series A-ish startup in the online driver's ed. So teaching teens, preparing them for their driving test. Did that for another probably year and a half, under 2. So you're seeing a bit of a pattern here, which I can speak to as well, but fairly short stints as I'm trying to figure out where do I belong. Each stint gets me closer to a place of belonging, but not quite there. Yeah. So I go in-house at a place called driverzed.com. That's where I first start managing a team. And that is when I feel like, okay, I'm very close to being where I belong in that I figured out the hard stuff that I like. I like user acquisition. I like growth. I like building funnels, growing user engagement retention. I realized that I'm good at people management and I'm a good player coach. My sweet spot is I have a team that I can direct, but not such a large team to where I just become like an executive sponsor, which, by the way, eventually happened at Grammarly. But we'll get to that. My team was about 40 people by the end of my time there. And that's when I realized that, hey, I'm probably stepping a little bit outside of my sweet spot. So I learned all of that. And then the last missing piece, although I probably couldn't articulate it that well at the time, was I wanted to be at a place that was ambitious enough with the kind of talent where I didn't want to look around and feel like I was the smartest person in the room. I needed the talent bar to be higher. I needed the vision to be bigger, the goals to be more ambitious. more audacious. That was the missing piece of the puzzle, and I ultimately found that at Graham.

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It's probably cliché, but I'm really getting hung up on the undo part. Because if you're generally content with where you are today, you wonder if I had undone something or if I have the opportunity to undo something early on, where does that take me through today? There are mistakes, 100%, and I'll elucidate some of them, but I would stop just short of saying, I wish I could undo it. Maybe the only things that I for sure would undo Is anytime I have made someone feel bad inadvertently or intentionally, frankly, right? Given someone a cold shoulder professionally, didn't lend someone a hand when they needed it, didn't provide the kind of support to a direct report that I should have. Those are the kind of things that 100% I would go and undo. Because those were moments when I didn't live according to my values. And so it's a very easy thing to say I would go ahead and do it. But other things in terms of a mistake I would make on a campaign or take a job that— listen, early on when you're switching jobs, I had 4 jobs in 5 years before I landed at Grammarly and then Grammarly for 8 and a half. That whole 5-year period felt like one big mistake. Yes, hindsight is 20/20, but in the moment, I felt incredibly self-conscious, like, what's wrong with me? Is it the places where I land, or is it my inability to commit, my inability to persevere, my inability to stick it out?

In the moments when you moved on from those jobs, did you feel like you were running from something or running to it? If you could just go back in time.

I feel like it was a blend. It was like I was telling myself that I was running towards something, But there was another little voice somewhere in my subconscious saying, are you running away from something?

Let's say there was a 3rd person on the show and they're in the midst of that. So they're at their 3rd job in 3 years. How would you coach that person through continuing on to eventually find the right fit?

I do coach people in the midst of these types of decisions frequently, and I always try to unpack Or help them unpack what it is that motivates them and what it is that they feel is pushing them from where they are or pulling them to a new place and try to get down to first principles. And over time, you learn to listen for certain things that nudge me in one direction or another. The 2 directions being either coaching someone like, hey, maybe you give this another shot. Versus the other direction who's like, hey, it's time to move on. The first thing that I find, which is oftentimes really telling, is when someone is explaining to me all of the things that they find wrong in their current place or all of the justifications for why they think they should move on, I ask them, what of this have you told your manager? Who else in the company is aware of this? And so often the answer is no one, and they've been harboring all of this.

Yeah, just building up resentment, suffering in silence. That's the most common thing.

Right. So when I hear that, I say, no, you have work to do in your current place, even if it's just getting all of this out. And maybe it doesn't change your predicament at this place specifically, but it's going to be character building. It's going to be eye-opening for you, and it's going to help you build a certain muscle So that you can do that in your future roles, address things as they come up, right? Like, it's easy for me to say this because I'm now in more of a position of experience and privilege, but whenever I go into a new working relationship, I like coach them through how direct I am before I even have an opportunity to do it. I'm just like, hey, I believe in radical candor. I believe that the way we build a healthy, longstanding relationship is if we share things early and often. And so you're going to hear that from me a lot. Even if something has even the tiniest chance of polluting or contaminating our relationship, or if you said something that made me feel a certain way, I know I've learned over time that I'd rather just address it right away so we can squash it as a little thing and move on. But I know enough and I'm confident enough in my own skin now to be able to do that. I don't expect that of someone earlier in their career, so it is a little bit harder. It is something I try to coach people through, but at the same time, I have my own experience and I can't ignore it, which is ultimately it was the right thing for me to keep looking until I landed at Grammarly. It's hard to deny that, which has also made me a lot more empathetic as a hiring manager. This was always a struggle at Grammarly. I'll just finish this one last thought. In any kind of hiring engine or culture, you have to use pattern matching, right? Yeah, you can make an argument that everyone is unique, everyone's journey is unique. But when you're dealing, when you're hiring for dozens of roles and you're looking at hundreds of candidates, you have to learn shortcuts. Back in the day, shortcuts may have been around where you went to school, but then over time we got smarter and now we are paying less attention to that. At least most hiring teams, but you have to use shortcuts. And one of the shortcuts was avoiding people with short stints, especially consecutive short stints. And you know what? Probably it is a helpful shortcut net, right? Because you know that with any shortcut that you're using, you're going to have false positives, but you're just hoping that those false positives are fewer than the false negatives if you did not use that shortcut. But I always had that tension when looking at a candidate and there'll be like a hiring panel and it'll be like, look at this, the last 2 stints were sub-2 years each. And I'll be like, yeah, that's concerning. And they'll be like, wait, hold on a second. What about me?

Right? Yeah.

I don't have an answer to that, but just being hyper-aware of that, I think has made me a more thoughtful and deliberate hiring manager.

Yeah. Earlier you said something that I thought was really interesting. I want to double-click on it for a second. You said, when I start a new stint, I try to let my colleagues or peers or whomever know that I'm going to be direct and that I believe in radical candor, and I try to get ahead of it. And I'm curious on the other end if there's been a time where you've received tough feedback on the receiving end and what might come to mind there.

Maybe I'll give an example from my life at Grammarly and from my life post-Grammarly. At Grammarly, a lot of the tough feedback that I received was around being or not being sufficiently empathetic manager who focuses enough on relationship building and caring for the team's wellbeing more holistically. I think that especially early in my management career, I leaned much more heavily into making sure that my team can deliver on all of its goals at the highest velocity and do it at a high ROI. So I was spending a lot of time on how do we have a tight OKR process? How do we have strong roadmaps? How do we have a strong execution culture? And so more of like this puzzle builder, but people are not puzzle pieces. And I would get feedback around just not spending enough time. Oh, I would not go with people for casual coffee or my team would want to go and have an offsite lunch. I was like, go ahead and do it. But I would think it's a ridiculous luxury and I'm not going to go for an hour, leave the office. I'm now being more sarcastic about it, of course, right? Like, I got shit to do and I've gotten feedback eventually. That's one thing that we did really well at Grammarly.

How did you receive this feedback? Was it written? Who was it from?

It came from direct reports, primarily as part of like a 360 feedback cycle. And there was one feedback cycle within these every 6 months where that team up from 4 different people.

So every 6 months you have a formal review. It's probably with your manager. So is this like the night before you have the sit-down with the manager, you get the pamphlet with all the raw feedback and you have a chance to read it? I'm just trying to understand. what it might have felt like in the moment.

Yeah, I don't remember if it was like the night before I have to sit down with my manager, but I definitely can summon up that feeling now because I've gotten critical feedback many times, but the feeling still doesn't go away. Initially, it stinks. Initially, it stinks. Even though my philosophy is feedback is a gift, and I'm grateful to anyone who had the courage and the care To let me know. There is a saying, you can never control your initial reaction, but you can control your eventual response. And so the initial reaction is, I feel flushed. I feel like the walls are closing in. It feels harsh. It feels unfair. It feels like, don't you know how much I do for the team? You have the luxury to go out to lunch, but I have all of this and this and this, and you don't know what my life is like. That's the initial reaction.

I'm feeling it as you're sharing it, of course. Did you agree with the feedback though, for what it's worth, after you had a chance to react to the blow?

For sure I did. I would say with 95% of it. I think that especially given the expectations that we had at Grammarly for people, we wanted people to work their fucking asses off for us and do it for many years. And we prided ourselves on having people stay for 3, 4, 5, 6, 7, 8 and a half years in my case. And you gotta be able to pair the go, go, go with more lightheartedness, more personal relationship building. Early in my career, I would reserve that for things like formal offsites or something, but I wouldn't really sprinkle it in throughout the week.

Yeah.

I was known as the intense guy, like, oh, Yuriy, he's intense. And that wasn't meant as a compliment.

So you shared it obviously today for a reason. Did this become like one of those moments that like was painful in the moment, but kind of becomes a step change for who you are and how you operate and how you approach things as a manager and as a leader?

Yeah, 100%. I was under a lot of stress and pressure at Grammarly. It was because we had really audacious goals. But I suspect it was largely because of the pressure I put on myself. This is just innate to my nature. I have a to-do list, but the amount of pressure I'm under to complete it, it's as if someone else wrote it for me. It's as if I owe someone else all of these items, and I'm aware of that. I would sometimes be working late into the night so I can cross everything off of my list, and rarely do I pause and say, wait, hold on a second. Yes, you were hoping to get all of these things done, but are these objective deadlines? Who is going to be hurt if you don't complete it today? On the few occasions that I do pause to ask that question, guess what? These were somewhat arbitrary deadlines. Anyway, this is just a little backstory for the pressure that I was under, and I felt like I just couldn't spare any time for anything that I didn't feel was absolutely essential to completing our goals.

And so probably this is a superpower early in your career, right? That kind of horsepower, that kind of dedication, that kind of focus, the hustle. I know we came up probably in the hustle era now. So it also was a kryptonite in addition to it being your superpower is what I'm hearing you saying.

Yeah. But here is the beauty of the last 4 years and maybe tying it together.

Yeah.

Because I didn't know that I was going to embark on this journey of the last 4 years. It started of just me reaching some kind of boiling point. Boiling point is probably too strong of a word. I was very happy at GrammarlyNet. Like, I couldn't think of a better operating job, to be honest. But I think I was burning out without knowing how to label it. I just felt like I needed to change that rhythm, not because the company expected so much from me, but because of what I just told you. And for 8 and a half years, there is that kind of self-imposed urgency and pressure and et cetera. And I just felt like I needed to take a step back from that. But my best guess at the time in 2020 or late 2019 when I made the decision, my best guess would've been I'm going to take 6 months off. I'm going to completely flush everything out of my system. I'm going to detox from what it's like to be at a startup, and then I'm going to get back to building because that's all I knew how to do. We can talk about this separately if you'd like, but I kind of stumbled into advising. Eventually it took off, it took on a life of its own. The flagmill started spinning. I'm 4 years in, and here's an observation that I wanted to highlight. Because in the work that I do, I largely do not have OKRs and I largely do not have direct reports. Why? Because it's not entirely true. Sometimes when I'm really involved with a company, I may sign up for a couple of quarterly key results, but it's nowhere close to the volume or the level of intensity at Grammarly. While I don't have direct reports, I do direct teams, but I'm not accountable for their career growth, for their career progression and stuff. What this has allowed me to do is 2 things. Number one, just practice more strategic thinking, big picture thinking, being able to piece together trends that you're not able to do when you have blinders on and you're just in extreme operating mode. But with respect to managing teams, I have the luxury of being more of a coach and I have the luxury of actually focusing on developing and managing morale because I oftentimes find myself in a situation where, let's say it's an early-stage company, you have a marketing or growth person that's reporting directly to the CEO. The CEO has a million things to do. The CEO cannot be a functional mentor to them. And so I come in and I fill that role and I'm able to Bring a lot more purpose, meaning, and focus to these people's roles, which is exactly the kind of thing that I was criticized for not being great at at Grammarly. And now I'm having the opportunity to really practice it. So I tell myself, okay, I've done extreme building, like extreme operating. Now I'm doing the extreme opposite thing. I'm sort of like this mercenary in many ways. If and when I get back to building, I'm going to be hyper-conscious about what kind of operator I want to be in my next chapter as an operator, as a builder, or maybe as a founder, which is also a builder of a sort, right? Don't throw out the baby with the bathwater, right? So whatever I learned in my 4 or however many years of advising and doing fractional work, including in building relationships and mentoring and coaching a team, Bring that into my next stint as a builder.

That's beautiful. So you said at your last gig, or you said when you were at Grammarly, you got feedback and you were known as the intense guy, but you're recalibrating a little bit. What would you like to be known as whenever that next step happens in that next operator role? If we could fast forward, what would you like them to say about you?

Empathetically intense.

Don't want to deviate too far from the magic.

Yeah, I'm at a different point in my life. In the last 4 years, I've been able to invest in other aspects of my life that I haven't been able to do while at Grail.ly, or at least didn't give myself the permission to. I want to be very careful. At first, as I started doing advising, I started exercising like crazy, eating clean, doing sauna every day, spending time with kids, taking them to extracurriculars, all of this stuff. I'm like, oh my God, this is amazing. It's impossible to do any of this as an operator. That was my conclusion. It was like 1 plus 1, it was 2. At Grammarly, I was eating like crap. I wasn't exercising, I wasn't sleeping. I would barely see my kids or kid at the time. And now I'm not operating and I'm able to do all these things. Eventually I've evolved my thinking and I don't think it's so black and white. And so when I go back to building, I want to be known as someone who knows how to balance things. It doesn't mean that it's a perfect balance. If I go back to building, some things will need to take a little bit of a sacrifice. You cannot be naive about it, right? That kind of flexibility I have in my schedule right now, if you want to build something meaningful and you want to be in the leadership role building it or as a co-founder, you're going to need to dial some things back. But if I can align it with when the kids are a bit older, And just figure out how to be smarter and optimize my time better. To answer your question of how do I want to be, I want to be known as someone who can deliver A+ results but still live a meaningful life all around.

Oh, that's beautiful, man. And you had talked earlier in our conversation about Radical Candor, the concept, but the book, I assume you've read?

I don't think so.

I bring it up because in the book she talks about different chapters of your career and chapters where You might want to be a superstar versus a rock star. Superstar is probably what you did at Grammarly, going above and beyond, working late, taking on more, gunning for promos, et cetera. And then other chapters in your career when you want to be a rock star, it doesn't mean you're going to do less. It just means you might not take on that extra 10%. You might just be satisfied signing off at 5 and going to soccer practice or whatever it might be. And that's kind of what I'm hearing you describe. It is a desire for more of that, still achievement, but maybe without just that last 10%. I think that there's a lot of people who look at you, myself included, and look up to you as a figure in the growth space and someone to grow up and be like. And I'm curious if we could go back in time, who did you look up to? Who were those people for you when you were coming up in the tech and growth space?

First of all, I do want to say that I've always found the biggest inspiration to be outside of the industry, just to be very clear, right? It's family, it's other world figures that I followed or looked up to. But if I think about where I drew inspiration professionally, there were a few figures. So I remember when I first landed at LeadQual, everything in finance, I'll be very honest, there was no one that I encountered in finance that I wanted to be. And I think it just had to do with, it's not that they were bad people, but it was just like, I think they were living professional lives that I wasn't interested in replicating. So it was a little hard to find inspiration there. When I first landed at LeadQual and I found other Cal grads a few years ahead of me, doing meaningful work in their element, those were the first people professionally I started looking up to. Then at Grammarly, I was just spoiled with figures or professional heroes, if you will, right? From the Grammarly co-founders that founded Grammarly Ukraine, that went out on a limb and were willing to tackle a challenge so audacious without having your typical Silicon Valley or Ivy League school upbringing. To the Grammarly CEO who had a nice cushy career as an investor and decided to basically come and become Grammarly CEO virtually for free initially. Brad Hoover, incredible inspiration, and he's become a really good friend over the years. And then when I was at Grammarly, I was looking and I was thinking about what my life beyond Grammarly looked like. And that's when I had a chance to connect with people like Casey Winters and Elena Verna. who were a few years ahead of figuring out what other ways are there to work besides just like a job or another job. Are there other modes out there? And Casey, Alena were generous with their time in terms of helping me figure out what's next. So I looked up to them and continued to look up to them. And today I draw most of my inspiration from founders in the founder community. Those are the people I spend most of my time with. In the last 4 years, I've worked with north of 30 companies, which basically means north of 30 founders. And I would say the vast majority of them are just phenomenal human beings with phenomenal potential. And spending time with them, helping them become even greater when they're already so fucking great, that's been the privilege of a lifetime. But that's where I draw a lot of my inspiration from today.

And if we could go back in time, What's a skill that you wish you had worked on sooner and why that might have been helpful in your journey?

The first one is I always felt that the fact that I didn't come from a technical background was a little bit of a disadvantage. I mean, I made it work, but if I knew how to code or if I spent some time in product development and product management, I feel like it could just make me even more dangerous. So that is a skill that I wish I spent time honing or earlier, and it could have taken a variety of ways. I could have taken a coding bootcamp. I could have spent a couple of years as a PM. There were probably ways I could have done it if I was intentional about it. That's one. The second one I'll say is, this is going to sound a little self-promotional, but I think I've said enough humble things where I can afford to say one, right? I consider myself a pretty prolific networker, an intentional, systematic, deliberate networker. I unlocked this skill towards the end of my time at Grammarly. If I had unlocked it sooner, knowing now how powerful it is, maybe I would've changed my trajectory even further. But again, at Grammarly, I was like, for the first 6 of the 8 years, I was like, if you want to be great at building, just build. Everything else is a luxury. You want to grab coffee to what? I'm sorry. When I started networking and I became intentional about it, it's paid so many dividends. So many dividends.

That's probably the best answer I've got to that question. I would actually answer it the same way. I feel like as I reflect back on my own career, I wasted a lot of these opportunities where I could have picked the brains of people that I had no business being in the room with and develop relationships. And who knows where that leads you, right? And that's what you're saying. Sometimes it's hard to know where networking Pays off because the benefits aren't always obvious and right in front of our eyes, but investing there is a huge benefit, obviously, down the road. Yuriy, thank you for coming on and sharing your story and your background and your childhood and some of the mistakes along the way in your career. For those who are listening that want to learn more, want to work with you, where should we send them? How can they connect with you?

So 2 places, yuriytimen.com. You can learn more about my work there. Once this episode goes live, I'm going to link to it from the website. So some of my content written and otherwise goes on there. And then as well as my LinkedIn, I'm going to try to be a little bit more active on LinkedIn with some short-form content in the near future.

You thinking video content? Is that what we're thinking about?

I don't know. I'm probably going to start with editorial, like short-form editorial, but we'll see. That's something that does not come natural to me, to be honest. Having conversations like this very much comes natural to me, but solo videos or Editorial, that's something that I have to nudge myself into more.

Yeah, I was curious about that. You're like one of the only solopreneurs that isn't hawking a newsletter or a podcast like what I'm doing. And so I was curious if that was intentional or part of the plan or what.

It's been intentional because I've been guided by, like the last 4 years, I've been very much guided by do things that are energy-inducing, don't do things that are energy-draining. And this conversation here is energy-inducing. I'm going to go on and have an amazing rest of my day. If I spent this time sitting down with a blank page trying to write some kind of blog post, that would be energy draining for me just based on how I'm built. Maybe that can change with the advent of AI. Maybe writing can become more enjoyable for me, and I'm eager to look into that. But that's why I do what I do and don't do what I don't do.

No point in working for yourself if you don't love the job.

Yeah.

Hell yeah, man. Thank you again. We appreciate the time.

Cool. Thank you, Andrew. Appreciate it.

Thank you for listening to the pod. I hope that you enjoyed the episode. If you did, the biggest gift that you could give me as a small business owner and as a content creator would be a review. You know the game. You can go onto Apple Podcasts, you can go on Spotify, leave a review. That would help me service this content to other folks who are like you. Obviously, you should subscribe to the content if you really dug it. And if there's feedback that you have for me, folks you think I should chat with, stuff that you wish I would gloss over faster, whatever it is, I'm all ears. I work in growth. You're not going to hurt my feelings. I try to collect feedback and iterate quickly. You can reach out to me on LinkedIn @AndrewCaplan or on Twitter @ACaplan. Otherwise, hope you enjoyed the episode, and I'll see you next show.